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Green Chemistry: The Nexus Blog

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Contributed by Phil Dahlin, Sustainability at Janssen

 

The connection between green chemistry and health is one that I am both personally and professionally engaged in. Healthy people depend on a healthy planet. And so I see environmental stewardship as a vital component of our pharmaceutical business. At Janssen, the pharmaceutical companies of Johnson & Johnson, this includes investing in innovative approaches to improve our environmental footprint.

 

Assessing Product Lifecycle

 

Chemical processes have a significant impact on a pharmaceutical product's environmental footprint, so integrating more green chemistry into standard practice has been a business imperative for Janssen over the last decade. Johnson & Johnson utilizes its Earthwards® approach as way of addressing the impacts of our products, throughout their lifecycles. Life cycle assessment (LCA) methodology – looking at both products and their components from cradle through use and end-of-life – has come a long way since the first widely-recognized study performed by Coca-Cola in 1969. Janssen found that performing LCAs has helped us to identify opportunities to better incorporate sustainability into our product development processes and reduce our environmental impact. However, what we’ve learned is that a full-blown LCA is a very intensive exercise, the data acquisition is not always straight-forward, and performing a LCA on every product we manufactured was simply not feasible. We also discovered that there were no existing methodologies at that time to adequately assess the sheer volume of variables associated with pharmaceutical products.

 

Collaboration

 

We decided to partner with the Department of Sustainable Organic Chemistry and Technology at Ghent University, Belgium (UGent) to develop state-of-the-art methodologies in sustainability assessments that would simplify the LCAs we had to perform and identify priority variables. Janssen has a long-time, productive partnership with UGent, so the collaboration was a natural fit to find more efficient ways of understanding where the largest impacts of our processes were.

 

After conducting a full LCA on 40 different chemical manufacturing steps and gathering data on 15 potential predictor variables, we were able to develop a highly-predictive model of the environmental footprint of a product using just three variables. This method showed us where we had the largest opportunities to streamline our development and manufacturing processes, and where we might invest in footprint reduction initiatives. It also earned some of our products Earthwards® recognition1 , an honor recognized by Johnson & Johnson leadership for our most broadly improved products.

 

What Next?

 

Inspired by the success of this collaboration, Janssen is proud to support the ACS GCI roundtable on green chemistry. We believe that by working together to address the ethical, social and environmental aspects of our industry, we can all achieve the best outcomes for our patients and society. We look forward to further collaborations in the future on the path to creating more sustainable medicines in 2015 and beyond.

 

Reference

1e.g. galantamine HBr, active pharmaceutical ingredient of REMINYL®/RAZADYNE® (3 API manufacturing process generations)

 

 

 

“The Nexus Blog” is a sister publication of “The Nexus” newsletter. To sign up for the newsletter, please email gci@acs.org, or if you have an ACS ID, login to your email preferences and select “The Nexus” to subscribe.

 

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As the global population increases (trending towards 9 billion people by 2050), it is anticipated that food production will need to increase by 70 percent to meet global demand. Sustainable agricultural practices will increasingly be needed as the industry seeks to minimize its human and ecological health impacts while scaling and providing for this demand. One of the biggest areas that chemistry influences agriculture is pesticides. Greener pesticide technologies are catching on more and more, and in particular, biopesticides (a market that is projected to grow to $4.5 billion in 2023).

 

Early pesticides were typically highly toxic materials (e.g., Arsenic) or synthetic organic compounds (e.g., DDT). Some of these conventional technologies faced government phase-outs (due to their toxicity, persistence, or insolubility) or pest resistance. Public concern over pesticides had a strong influence in shifting away from some of the more toxic pesticides over the last several decades. In general, since then consumers have been pushing chemical markets towards natural products (though it is important to remember that not all natural products are safe).

 

Biopesticides are a certain type of natural product that are used to control pests, plant diseases, and weeds. The two major categories of biopesticides: biochemical and microbial. Biochemical pesticides control pests with naturally occurring substances such as insect pheromones, plant extracts, and plant or insect growth inhibitors. Microbial pesticides use microorganisms as the active ingredient (bacteria, fungi, viruses, and protozoans). (Transgenic crops (also known as plant incorporated protectants) are also technically considered to be biopesticides, where scientists modify a plant’s genetic material with specific pesticidal proteins, but will not be addressed in this post). The primary advantages of these biochemical and microbial bioproducts are that they are usually less toxic than conventional pesticides, affect only the target pest, can be used in very small quantities, and can decompose quickly. On the flip side, they typically have shorter shelf lives, limited persistence, and can be slower acting.

 

The U.S. EPA’s Presidential Green Chemistry Challenge Award (PGCCA) has been granted 13 times to innovators who have developed greener pesticides. Seven of these technologies are considered biopesticide-related or are processes that support the bioproducts’ pipeline. For example, in 1997 two professors from Michigan State University won the academic award for developing genetically engineered microbes and a process for synthesizing catechol (a building block for many pesticides that is usually derived from petroleum-based benzene). Another notable award is the 2001 Small Business Award to EDEN Bioscience Corporation (since then the technology has been acquired by Plant Health Care, Inc.). The team developed and commercialized harpins, a new class of proteins produced by plant pathogenic bacteria. Without altering the plant’s DNA, harpins can activate the natural defense mechanisms of the plant, fight disease and pests, and trigger the plant growth systems. This technology is not only considered non-toxic, but is produced via an essentially waste-free water-based fermentation process.

 

Another challenge that biopesticides can face is that they can unknowingly affect a broader spectrum of non-target species. One example is spinosad, Dow Agroscience’s 1999 Designing Greener Chemicals PGCCA Award. The product is developed through a particular soil microorganism. It was highly effective on specific species, and had a favorable environmental profile with low tendency to leach, persist, bioaccumulate, or volatize. (In 2008, Dow Agroscience won again for a spinosad development—spinetoram, a more effective equivalent biopesticide for tree fruits and nuts). While spinosad was significantly safer for humans, in the early 2000’s it was discovered that it was intrinsically toxic to pollinators.

 

It is clear that biopesticides are a key tool for more environmentally benign agricultural practices, but not without some issues to always be aware of. Like all greener chemistry innovations, there is a constant thrust for continuous improvement and deeper understanding of what hazard means in this field. In addition to products to be applied directly to plants, there are biopesticide treatments being developed for seeds and soil amendments. Through multidisciplinary collaborations (between chemists, entomologists, toxicologists, etc.) these products can continue to grow in safer, holistically understood ways and support more sustainable agriculture.

 

 

 

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Towards a sustainable model of agriculture in Brazil: Divulging the role of the National Institute of Science and Technology for the Biorational Control of Pest – Insect (INCT-CBIP)CBIP-logo.png


Contributed by Vânia G. Zuin, Maria Fátima G. F. da Silva, João Batista Fernandes, Moacir Rossi Forim, Universidade Federal de São Carlos (SP-Brazil), Department of Chemistry

 

The main objective of this manuscript is to provide a modern overview of the current green approaches for insect pest control, detaching some specific cases in Brazil. As is well known, these alternatives to classical agrochemicals have been attracting the interest of a vast group of people and institutions all over the world: academic, industrial, governmental, and nongovernmental sectors, as well as the society in general. The Natural Products Research Group of Universidade Federal de São Carlos, SP-Brazil (UFSCar) was formed more than 30 years ago. The research interest of the group covered many aspects of general phytochemistry. The State of São Paulo Research Foundation (FAPESP) has been contributing systematically and substantially to these interdisciplinary investigations, allowing the development of new scientific strategies for the study of natural products, for instance, supporting two thematic projects: “Study of the potential of some plant species and natural and synthetic products for the control of leaf-cutter ants”, coordinated by Prof. Fernandes; and, "Phytochemistry and chemical ecology: Search for starter compounds for new insecticidal, fungicidal and bactericidal drugs for control of plant pests”, coordinated by Prof. Silva. In developing these studies the group had strong interactions with a number of other Brazilian research groups. The National Institutes of Science and Technology Program (INCT), launched in 2008 by the Ministry of Science, Technology & Innovation (CNPq) permitted the expansion of the main group. Thus, Profs. Silva, Fernandes, Forim and Zuin aggregate in their networks the best research groups and companies of chemical ecological and education areas from several states in Brazil, including international partners based on Europe and North America more recently, in order to make Brazil a referential country when the control of insects with low impact to the environment is aimed, through the National Institute of Science and Technology for the Biorational Control of Pest-Insect (INCT-CBIP).

 

Mission

 

The efficient control of insects and the search for biologically active compounds that are closely related to human survival are important issues to be studied. Insects are the greatest competitors of mankind with regard to food, besides being vectors of a number of diseases that affect humans, herds and plants. The objective of the INCT-CBIP was to carry out studies to control biorationally pest-insect and their associated microorganisms such as fungi, bacteria and yeasts.

 

CBIP-graph.pngThe assays of pesticide activity and inhibition of fungi and bacteria have been performed with plant extracts and natural products from plants or microorganisms. The toxicity of a number of extracts and natural compounds to insects, fungi and bacteria were determined. The extracts and natural compounds showed moderate activity in comparison with commercial insecticides. Thus these compounds were assayed against other targets. Neem oil from Azadirachta indica showed significant activity as an insecticide. However, if it is assumed that it is possible to modify the chemical structure and/or complexation with metals the compounds to improve activity and selectivity, our results helped in directing the rational design of coumarins, alkaloids and flavonoid derivatives and the last as potent and effective insecticide, fungicide and bactericide.

 

Enzymes that degrade the polysaccharides of the vegetal (pectinases and amylases) in reducing sugars have been detected in symbiotic fungus and also have been found in the fecal liquid of the Atta sexdens rubropilosa or leaf-cutting ant. These sugars constitute the main source of energy for the ants' nest. Therefore, the ants use symbiotic fungi to promote this process of degradation, once they are not capable to degrade the pectin directly.

 

CBIP-Mosquito.pngThe enzyme acetylcholinesterase (AChE) is present in the central nervous system of insects, and hydrolyses the acetylcholine neurotransmitter in acetate and choline, thus finishing the synaptic transmission, playing a fundamental role in the transmission of the cholinergic nervous impulse. Two genes, Ace1 and Ace2, have been characterised in different classes of insects and two mutations in Ace1 have been associated with resistance in mosquitos. Enzymatic bioreactors were prepared using the enzymes acetylcholinesterase, butirilcholinesterase, and pectinase, and were used for studies of mechanism of action of substances, which presented inhibition activity against insects.

 

In addition to promoting the development of national competence in vanguard scientific and technological areas and creating rich environments for researchers, the INCT-CBIP is directly responsible for training students and divulging the results of its investigations at several levels.

 

CBIP-professors.jpg

 

The integration of both techno-scientific and educational aspects related to the role of sustainable agriculture in Brazil allowed Prof. Zuin to be recognised as a researcher who has been contributing significantly in analysing bioactive high-value organic substances extracted from agro-industrial residues and also studying curricula for courses in environmental and green chemistry, the latter also through the IUPAC project “Green Chemistry in Higher Education: Toward a Green Chemistry Curriculum for Latin American and African Universities”. In 2014, Prof. Zuin was awarded the IUPAC CHEMRAWN VII Prize for Atmospheric and Green Chemistry, at the 5th International IUPAC Conference on Green Chemistry, held in Durban, South Africa at the end of August. As can be seen, The INCT-CBIP has a detached role in the Brazilian scenario, developing a number of green approaches for the biorational control of insects of interest in Brazil, bringing together international researchers and companies, and also contributing to the improvement of science teaching and the scientific dissemination to the population taking into account the sustainable agriculture models in Brazil.

 

 

References:

SEVERINO, V. G. P.; FREITAS, S. D. L.; BRAGA, P. A. C.; FORIM, M.R.; SILVA, M. F. G. F.; FERNANDES, J. B.; VIEIRA, P. C.; VENANCIO, T. New limonoids from Hortia oreadica and unexpected coumarin from H. superba using chromatography over cleaning Sephadex with sodium hypochlorite. Molecules, v. 19, n. 8, p. 12031-12047, 2014.

 

PERLATTI, B.; FORIM, M. R.; ZUIN, V. G.  Green chemistry, sustainable agriculture and processing systems. Chemical and Biological Technologies for Agriculture, v. 1, p. 5-14, 2014.

 

Pictures:

1) Diagram of complexes of bioactive natural products with inorganic ions,

2) A. aegypti,

3) Profs. Zuin and Silva.

 

 

 

“The Nexus Blog” is a sister publication of “The Nexus” newsletter. To sign up for the newsletter, please email gci@acs.org, or if you have an ACS ID, login to your email preferences and select “The Nexus” to subscribe.

 

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Contributed by Ranae Jorgenson, Analytical Chemist, Agricultural Utilization Research Institute (with contributions by Liz Morrison, Freelance Writer)

 

At the Agricultural Utilization Research Institute (AURI), we are all about discovering new uses for agricultural resources in order to fuel economic growth in Minnesota. We work in four main areas—biobased products, coproducts, food and renewable energy. Several of our current projects focus on using chemistry to improve the nutrition of animal feed.

 

Specifically, two projects I want to highlight are:

  • Producing nutritious animal feed from corn stover (corn stalks, leaves, and cobs) and,
  • Enhancing soybean meal as a fish meal replacement.

 

Producing nutritious animal feed from corn stover

 

AURI is testing a way to make corn stover and other biomass more nutritious for livestock. Why is this needed? For example, in 2012, we saw many cattle producers losing their herds due to insufficient fodder and yet there was lots of baled corn stover available, if it could be made more nutritious.

 

Lignocellulosic biomass, like corn stover, contains plenty of nourishing carbohydrates, but they are locked up with lignans, making them undigestable. Although the technology isn’t new, researchers at AURI’s coproducts lab in Waseca, Minnesota, are using an alkaline solution to break down the bonds and release the nutrients so they are easier to digest.

 

The process “takes low-quality roughages and improves the available energy for dairy cows, beef cattle, and sheep,” says Al Doering, AURI coproducts scientist, who is leading the trials. The research could add value to crop residues like corn stover and perennial grasses, while cutting livestock feed costs and expanding biomass uses.

 

Calcium hydroxide, or slaked lime, is mixed with water and applied to chopped biomass. The treated material, which is about 50 percent moisture, is then packed into a bunker or bag and ensiled for 30 days. The cured feedstuff can be substituted for a portion of corn and hay in ruminant livestock rations.

 

“This technology has excellent potential to create new sources of high quality animal feed from underused resources,” Doering says.

 

AURI’s preliminary results suggest that calcium hydroxide treatment boosts the energy content of some crop residues — including corn stover and barley straw — by more than half, Doering says. That would make them nutritionally comparable to medium/low-quality alfalfa hay. “We’ll need to see a big jump in nutritional energy availability to offset the processing costs.” AURI will also test the feasibility of pelleting treated biomass to make it easier to ship—but that’s a long shot, Doering says. “I see this primarily as an on-farm application—treating forages like silage.”

 

Soybean meal as a fish meal replacement

 

Soybean meal, while an excellent animal feed, cannot be fed to a whole range of animals as soluble sugars in soybean meal are very disruptive to the digestive tract of baby pigs and carnivorous fish, in particular. And fish meal, which is often used, is increasingly expensive and in limited supply due to the decline in ocean fisheries.

 

That’s where Protein Resources, LLC, saw an opportunity to innovate and provide a feed ingredient that the market has been waiting for. “We felt that the market was looking for a soy-based, high-protein feed supplement that could be used in a variety of applications such as baby pig diets, poultry, aquaculture and possibly several other formulations,” says John Pollock, president of Protein Resources, LLC.

 

Working with AURI scientists, Protein Resources developed a cost-competitive, proprietary process to remove the fiber and sugars from soybean meal, leaving a digestible and high-protein feed. The extracted carbohydrates are used in dairy and beef cattle rations. The branded feed, sold as NutriVance Soybean Meal, will be marketed domestically and internationally to hog, poultry and aquaculture producers.

 

 

 

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Catalysis, the process of reducing a reaction’s energy requirement through use of a catalyzing agent, is a standard design principle of green chemistry. Yet many of the catalysts that chemists use are made out of rare metals like platinum. Figuring out how to do catalysis without using unsustainable catalysts is a priority to green chemists and companies seeking to find better, more efficient, cheaper, and ecological pathways to produce their products. One inspiration for solving such a problem has been nature.

 

Enzymes, a type of protein, are nature’s catalysts, working within cells to speed up reactions of all kinds. For example, enzymes in our digestive tract help break down food so that we can more rapidly benefit from it. But how can enzymes help chemists? Well, what if enzymes could be manipulated to catalyze the industrial reactions industry performs, such as creating a drug molecule or biofuel?

 

Enter Dr. Frances Arnold, professor of chemical engineering, bioengineering and biochemistry at Caltech and director of the Donna and Benjamin M. Rosen Bioengineering Center. Arnold has developed a method of protein engineering called directed evolution. The basic process involves encouraging random mutations in the gene sequence for a protein of interest, such as an enzyme catalyst. The genes are introduced in bacteria or yeast, which produce the mutant enzymes.  As the bacteria express the mutated genes, the resulting proteins are screened for favorable behaviors. Genes responsible for favorable traits are then extracted and reinserted into the next evolutionary round.

 

Directed-evolution-2.jpg

Credit: Joe Lertola, Bryan Christie Design

 

The goal of the process is to produce an enzyme that works in a way not found in nature. “I’m most excited about creating enzymes to catalyze reactions that nature never cared about or discovered,” says Professor Arnold. “I want to evolve chemical novelty, in the form of whole new enzymes.”

 

Over the past two years, Arnold has published 10 papers on this subject, finding enzymatic approaches to reactions that previously only chemists had been able to produce. But finding novelty through evolution is not always easy.

 

It’s clear that nature has the capacity to produce new catalytic activities, for example degrading synthetic pesticides sprayed on crops, but it’s far from clear how nature creates these new catalytic pathways. Cracking this code is a challenge that could open up opportunities to replace many of the reactions chemists do with more favorable, biological reactions. Breaking down the walls between traditional catalysis and biocatalysis will maximize the creative potential of both fields.

 

In Arnold’s research group at Caltech, students of molecular biology, biochemistry, bioengineering and chemistry work together. “I know chemists who feel that biology is the big frontier for them,” says Arnold. “They can apply their more traditional chemical knowledge to identifying new opportunities for biological synthesis.”

 

Young chemists know that the field is changing and more jobs are opening in these cross disciplinary areas. According to a MarketsandMarkets Report released in February, the market for biocatalysts is projected to grow at 5.5% per year and reach 11.94 kilo tons by 2019. Driven by technological advances, biocatalysis is particularly strong in Europe and the United States, where biocatalysts are used in laundry detergent, the food and beverage industry, the specialty chemicals and pharmaceuticals industries, and increasingly in the production of biofuels. Many start-ups are employing these methods, especially in the production of biofuels and specialty chemicals. Arnold herself has founded two companies, Gevo, Inc., which uses her methodology to create the biofuel isobutanol, and Provivi, a start-up that is developing new products for crop protection.

 

Large companies are also embracing the developing capabilities of biochemistry. In 2010 Merck, in partnership with Codexis, developed an enzymatic process for producing the active ingredient in Januvia™, a drug used in the treatment of type 2 diabetes. The new process replaced a rare metal rhodium catalyst, and won the team a Presidential Green Chemistry Challenge Award from the EPA that same year.

 

Professor Arnold will be keynoting at the 19th Annual Green Chemistry & Engineering Conference this July 14-16 in North Bethesda, Maryland where she will talk about chemical novelty and the opportunities for green chemists and engineers in this field.

 

“Doing great science is hard, but doing great science that has an impact is even harder,” says Arnold. “So if you like challenges, try to do that.”

 

 

Arnold has received numerous honors, including induction into the National Inventors Hall of Fame (2014), the ENI Prize in Renewable Energy (2013), the National Medal of Technology and Innovation (2011) and the Draper Prize of the National Academy of Engineering (2011). She has been elected to membership in all three US National Academies, of Science, Medicine, and Engineering. Among other activities, Prof. Arnold chairs the Advisory Panel of the Packard Fellowships in Science and Engineering and serves as a judge for the Queen Elizabeth Prize in Engineering.  Arnold holds more than 40 US patents and has served on the science advisory boards of numerous companies. She co-founded Gevo, Inc. in 2005 to make fuels and chemicals from renewable resources and Provivi in 2013 to develop new products for crop protection.

 

 

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To read other posts, go to Green Chemistry: The Nexus Blog home.

Contributed by Ann Lee-Jeffs, Business Manager, ACS Green Chemistry Institute®

 

Jack Bobo1.jpgJack Bobo holds a special place in the world of food, science, and agriculture. He is a leading edge thinker and speaker working at the intersection of science, law and policy. Jack is responsible for global outreach to foreign audiences and senior foreign officials on global agricultural trends, climate change, food security, and biotechnology. Jack serves as the State Department's ex officio representative to USDA's Federal Advisory Committee on 21st Century Agriculture. As Senior Advisor, Jack travels frequently, speaking on behalf of the Department at international conferences and meetings to present U.S. agricultural trade and development policies to foreign audiences, including journalists, policy makers, students, and scientists. I met Jack over coffee in late February at his office at the U.S. State Department. We had an engaging discussion about the intersection of green or sustainable chemistry, food and agriculture.

 

Ann Lee-Jeffs: Why do you think consumers should care more about food safety and the source of their food?

 

Jack Bobo: Most people spend little time thinking about where their food comes from, how it is produced and how it makes it to their plate. Until something goes wrong, that is. As soon as there is a problem — E. coli in spinach or salmonella in peanut butter — people understandably begin to ask questions about food safety inspections, practices of the agriculture industry, and larger questions about how farming has changed in the past 50 years.

 

The same occurs with respect to hunger. Until 2008, when people in the Middle East and Haiti started rioting because of high food prices, the issue of access and availability of safe and nutritious food had practically disappeared from public discourse. Most of us underestimate the importance of a stable and safe food supply to our society and our standard of living.

 

Ann Lee-Jeffs: With the global population expected to reach nine billion in less than 40 years, what do you think is the role of green/sustainable chemistry in the agriculture space and safe food supply?

 

Jack Bobo: With the global population expected to reach nine billion in less than 40 years, the sustainable production of agriculture will be increasingly on the minds of governments, private industry, and even many consumers. Not only do we have to increase the amount of food available, we have to find ways to minimize its footprint on the planet. There is no activity that humankind engages in that has a bigger impact on the planet than agriculture. This is true in terms of impacts on land and water resources as well as in terms of greenhouse gas emissions.

 

Therefore one of the great challenges that confront all of us in the next 40 years is to figure out how to maximize the production of food while minimizing the negative consequences of agriculture — from polluted waterways to disappearing rainforests.

 

This seems like a daunting task, and yet, science and technology, and especially chemistry, have proven capable of increasing production year after year for decades. Prior to the 1900s, agricultural yields increased at a painfully slow pace. However, at the beginning of the last century a series of agricultural breakthroughs ushered in dramatic growth in food production. The first of these revolutions was the advent of synthetic fertilizer in 1915, followed by mechanization, hybrid seeds, pesticides and, most recently, genetically engineered (GE) crops. Corn is a great example; to produce a bushel of corn we use 50 percent less water, 40 percent less land, 60 percent less soil erosion, 40 percent less energy, and 35 percent less greenhouse gas emissions than we did just three decades ago.

 

Ann Lee-Jeffs: Why is green/sustainable engineering so important to ensure that agriculture saves the planet instead of destroying it?  What do you see happening that makes you think we are going in the right direction?

 

Jack Bobo: In order to feed the 9 billion people on the planet in 2050, global agriculture will need to produce 60 percent more food using less land, less water, less fertilizer and fewer pesticides. In other words, we will need to do everything better than we are doing it today and our rivers and lakes are already running dry. The rapid pace of technological development suggests that scientists may, indeed, be able to sustain the growth of the past. But this will only happen if scientists are able to apply the most advanced technologies to the problems at hand. This is a hardly a certainty at the moment given opposing views of the future as reflected in the slow food movement and liberalized trade in food products. Figuring out how to understand and balance these real and, in some ways, opposing trends, will determine the future health of our planet.

 

We need the best ideas from organic and ecological food systems combined with modern advances in molecular breeding and genetics if we are to address this pressing challenge and sustainably feed a growing planet. I will be the first to admit that science doesn’t always get it right. It’s also true, however, that you can’t get it right without science. The good news is that after 2050 population growth will slow dramatically and everything will get easier. So, if we are able to get to 2050 without cutting down our forests and draining our rivers and lakes, we will be good forever. The next 40 years are going to be the most important 40 years there have ever been in the history of agriculture.

 

We owe it to coming generations to use every tool available, from organic production to biotechnology, to increase the quantity and quality of food while minimizing the footprint of agriculture. This will require the attention and effort of all of us. Our lives and the lives of our children depend on it. And, if we’re successful, agriculture just might save the planet.

 

Ann Lee-Jeffs: What is your advice for the scientists and engineers who are working in the agriculture and food sectors regarding sustainable/green chemistry and engineering?

 

Jack Bobo: There has never been a more exciting time to work at the intersection of green chemistry/engineering and food and agriculture. Agriculture cuts across global challenges related to water, land, air and climate change. These challenges are driving demand for new technologies to promote public and environmental health. But there is also consumer demand for greener products that will accelerate the transition to a greener economy. Not only are new jobs being created every day, there are new companies being created and even entire new sectors of the economy that didn’t exist 10 years ago.

 

 

 

“The Nexus Blog” is a sister publication of “The Nexus” newsletter. To sign up for the newsletter, please email gci@acs.org, or if you have an ACS ID, login to your email preferences and select “The Nexus” to subscribe.

 

To read other posts, go to Green Chemistry: The Nexus Blog home.

ACSGCI

Message from the Director

Posted by ACSGCI Mar 17, 2015

Contributed by David Constable, Director, ACS Green Chemistry Institute®

 

Last week I had the privilege of seeing the work of three National Science Foundations centers. There are a total of eight centers that have received Phase II funding since 2007, and I would like to list them here:

 

Centers for Chemical Innovation – Phase II Awards

 

Center for Enabling New Technologies through Catalysis (Karen Goldberg, University of Washington) FY2007-2016

Award Abstract & Center Website

 

CCI Solar Fuels  (Harry Gray, Caltech) FY2008-2017

Award Abstract & Center Website

 

Center for Chemistry at the Space-Time Limit (V. Ara Apkarian, UC Irvine) FY2009-2018

Award Abstract & Center Website

 

Center for Chemical Evolution (Nicholas Hud, Georgia Institute of Technology) FY 2010-2014

Award Abstract & Center Website

 

Center for Sustainable Materials Chemistry (Douglas Keszler, Oregon State) FY 2011-2015

Award Abstract & Center Website

 

Center for Selective C-H Functionalization (Huw Davies, Emory University) FY 2012-2016

Award Abstract & Center Website

 

Center for Aerosol Implications for Climate and Environment (Kimberly Prather, UC San Diego) FY 2013-2017

Award Abstract & Center Website

 

Center for Sustainable Polymers (Marc Hillmyer, University of Minnesota-Twin Cities) FY 2014-2018

Award Abstract & Center Website

 

A further three centers received Phase I funding in 2012 and these are the ones I saw:

 

FY 2012 Phase I Awards – possible Phase II in FY2015

 

Center for Capture and Conversion of CO2(Tayhas Palmore, Brown University)

Award Abstract & Center Website

 

Center for Sustainable Nanotechnology (Robert Hamers, University of Wisconsin Madison)

Award Abstract & Center Website

 

Center for the Sustainable Use of Renewable Feedstocks (Peter Ford, University of California Santa Barbara)

Award Abstract & Center Website

 

It is great to see all the work these various centers are doing and I hope you take the time to look into them a bit more closely. The work that these centers are doing will be transformative and synergistic, and I heartily endorse and commend the NSF for continuing with this program. Unquestionably there is some great science being done at these centers, and it is very exciting to see the advances they are making.

 

Acknowledging this, the interesting thing to me is that many of the professors, graduate students and students in these centers, for the most part, don’t self-identify as doing green chemistry, despite the fact that many things they are doing, particularly the strategic aim of the center, is clearly embodied or envisioned in principles of green chemistry and engineering. Also, it is my experience that many chemistry researchers don’t pay much attention to things that are easy for them to change like solvent or reagent selection, relying instead on traditional reagents and solvents that shouldn't be used. I also see no real evidence of taking mass or energy efficiency into account, and thinking from a life cycle perspective is not generally thought about. This is an unfortunate state of affairs, but it does reflect the reality of most chemistry research at major universities.

 

As I find myself in discussions with academic researchers at all levels, I consistently hear the same themes in defending their research practices. They include such things as “we’re only doing proof of concept work,” or “it’s important to just see if the hypothesis works before we pay attention to whether or not something is “green” or “sustainable”,” or “we know that using gold is not something we can do commercially, but we want to learn on a well-behaved system before we move to the real world application.”  And so on, and so on. When I ask how well a model system in early chemistry research translates to real world environments, the answer is usually that it doesn't.

 

This in many ways sums up the dilemma that is faced by traditional chemistry researchers when they attempt to do research that is use-inspired or biomimetic. Suddenly there is the problem that surface effects, solvent effects, ionic effects, morphology, and so on, are incredibly important variables and our reductionist way of doing chemistry (i.e., holding one variable constant at a time) is not quite up to the task of understanding complex systems. We generally don’t teach statistical design of experiment and the use of principal components analysis or other related statistical techniques that may help us understand complex systems, so we go back to what we know and remain in two or perhaps three dimensions. The idea that one needs to look at the complex interactions in a system, and that the selection of boundary conditions exerts a critical influence over the chemistry of the system is not something many chemists seem to have a good handle on.

 

I am hopeful, however, that as more of these centers are funded and as more research at the interface of chemistry with biology, materials, engineering and other disciplines and sub-disciplines takes place, that more chemistry researchers will pay greater attention to all the principles of green chemistry and engineering. It is in the consideration of many of these principles, in embracing greater complexity in experimental systems, and by incorporating greater systems-level thinking that we will solve many of the sustainability challenges facing society.There is no lack of fun and interesting research to be done, and I am looking forward to the next generation of chemists to hit their stride and begin to tackle these challenges one-by-one.

 

As always, please do let me know what you think.

 

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Contributed by Sílvio Vaz, Jr., Research scientist at Brazilian Agricultural Research Corporation

 

Brazil is one of the largest agricultural producer around the world. The country has a diversified biomass production from agriculture based on grains and fruits for human and animal food and agri-industrial feedstocks such as soybean, sugarcane, cotton, etc. Furthermore, Brazil presents significant growth in the international trade of agribusiness, consolidating its position as one of the largest producers and exporters of food to more than 200 countries. These agricultural products and their residues can be considered as a raw material source for a renewable chemistry. However, it needs efforts in science and technology.

 

We can consider five objectives for R&D&I in the Brazilian agriculture:

 

  • Ensure competitiveness and sustainability of Brazilian agriculture;
  • Achieve a new competitive technological level in bioproducts, bioenergy and biofuels – here, closely related to green chemistry;
  • Intensify the development of technologies for the sustainable use of biomass and for the productive integration among the Brazilian regions;
  • Biodiversity prospect for the development of differentiated products with high added value for the exploration of new market segments – mainly, by the use of biotechnology;
  • Contribute to the advancement of the frontiers of knowledge and incorporate new technologies, including emerging technologies – e.g., to reduce dependence from agricultural and non-renewable inputs (e.g., fertilizers and pesticides), and to promote the agri-industrial waste usages.

 

Among the technologies with the greatest potential to influence the development of Brazilian agriculture for a horizon of 20 years, stands out those capable to change the genetic heritage (as nanobiotechnology), technologies for the reduction of environmental risk, the rational use of chemical inputs and consequent increase in economic efficiency, precision agriculture, and technologies for value addition and product diversification - green chemistry is a new trend to be considered in the last case.

 

On the other hand, the impacts of climate change will mean new behaviors in relation to the subject and there will be more pressure for conservation and the rational management of environmental resources in the production process, including stricter environmental standards. The frontiers of knowledge are constantly shifting, and new technologies are characterized by higher density in scientific knowledge. Thus, in the coming decades, there will be an increase on the complexity in the Brazilian science, technology and innovation, with the spread of highly relevant technologies for agriculture.

 

Biorefinery and green chemistry are two concepts that focus on sustainable utilization of biomass creating value chains similar to those derived from the oil derivatives, and they can be applied in agriculture and agro-industry promoting a biobased industry. There is a great synergy between them, mainly regarding the minimization of residues and environmental impacts for the creation of a green economy or bioeconomy. Furthermore, they comprise an integrated sustainable system (raw material, process, product and residues) according to technical parameters which take into account, among other aspects, energy and mass balances, life cycle analysis, and the application of practical principles to promote best practices for R&D&I and production processes. In Brazil, efforts have been made to evaluate the economic potential of biomass to support the development of sustainable chemistry. That means agriculture will provide a feedstock for chemistry.

 

 

 

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Contributed by Daniel Teitelbaum, Pollution Prevention Team Lead, Toxics Release Inventory Program, US EPA

 

For more than two decades, EPA’s Toxics Release Inventory (TRI) Program has required industrial facilities to disclose both their environmental releases and the measures they’ve taken to keep toxic chemicals out of our air, water, and land.  It was only recently, however, that the TRI Program began promoting this treasure trove of pollution prevention (P2) data as a resource for identifying demonstrably-effective green practices.

 

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More than 10,000 source reduction activities are reported to TRI each year, but can we tell which ones actually reduce releases? A rigorous statistical analysis of all TRI data shows that the average effect is highest for the reporting categories that include raw material (e.g., feedstock chemical) substitution and switches to aqueous cleaners from solvents. And a separate analysis of the pharmaceutical sector indicates that green chemistry practices contributed to dramatic reductions in the early-to-mid 2000s.

 

But more meaningful insights lie ahead. Beginning with reports due July 1 of this year, facilities will have the opportunity to report the estimated annual reduction associated with each newly implemented P2 activity. This information will shed new light on which types of practices (including six new green chemistry categories added in 2012) are having the biggest impact on companies’ environmental footprints. As always, facilities that implemented green chemistry will also be encouraged to highlight their successes by submitting a more detailed narrative in the optional P2 section of the form (see video).

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As TRI was founded on transparency, EPA has continually sought to increase the accessibility of TRI data on corporate sustainability. To this end, all of the facility-level P2 information and environmental metrics presented in the TRI P2 Search Tool are now available at the parent company-level as well. This means you can now compare toxic chemical management and greenhouse gas emissions data at the corporate level and see what each parent company is doing to prevent the release of pollutants to the environment.  You can also explore differences in P2 and waste management practices at different facilities within the same parent company – it’s your right to know.

 

To access TRI's P2 data and learn about reporting P2 to TRI, visit www.epa.gov/tri/p2.

 

 

 

 

 

 

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Contributed by Tiffany N. Ellison, Joseph R. Fortunak, Frederick E. Nytko III, Howard University, Department of Chemistry

 

Some time ago (December, 2012) we published a story about the work being done by Professor Joseph Fortunak and his research group at Howard University (HU) in Washington, DC. This communication is an update on that story.  Last year (2014) Dr. Fortunak estimates he was in nineteen countries including Equatorial Guinea, Nigeria, Tanzania, South Africa, Nicaragua, Brazil, Switzerland, and China. Before joining HU in 2004, Dr. Fortunak spent over twenty years in the pharmaceutical industry, contributing to the launch of over a dozen new drugs and a similar number of new generic products during that time. Howard University is an HBCU (Historically Black College/University) founded in 1867 to provide higher education for freed slaves. Howard has had a PhD program in Chemistry since 1954 and has trained over 20% of the African-American PhD Chemists in the United States.

 

Picture2.pngThese details are pertinent to this “update report” because the mission of Howard University meshes with Professor Fortunak’s work. Dr. Fortunak and his group members concentrate their efforts on developing new chemistry and technologies for the more efficient, less expensive production of essential medicines of assured quality. The results of this work are shared with pharmaceutical manufacturers in India and China who produce essential medicines for the treatment of HIV/AIDS, malaria, TB, and opportunistic infections. Dr. Fortunak’s work was awarded the ACS Astellas Foundation Award in 2009 for “Chemistry Impact on Human Health.” This research continues in collaboration with the World Health Organization, UNITAID, the William J. Clinton Health Access Initiative, and the Medicines Patent Pool.  An article in the Wall Street Journal (May 13, 2011) by Mark Schoofs described how Mr. Adrian Williams, an MSc student in the group, made a lasting impact on the availability of medicines for HIV/AIDS for low- and middle-income countries by improving the process chemistry for making the drug tenofovir disoproxil fumarate.  This chemistry was published in the Organic Process Research and Development Journal (2010).

 

Mount Kilimanjaro.jpgOne particular interest is the collaboration between HU and the St. Luke Foundation/Kilimanjaro School of Pharmacy (SLF/KSP) in Moshi, Tanzania.  Moshi is the nearest city to Mount Kilimanjaro, African’s tallest mountain. The area is a favorite with adventurous tourists because Kilimanjaro can be climbed in a several day trek without special equipment, while other famous sites including Olduvai Gorge, the Serengeti Desert, and Ngorongoro Crater are in close proximity.

 

Sister Zita Ekeocha is the founder and Director of the IPAT (Industrial Pharmacy Advanced Training) at the KSP, while Mr. Wilson Mlaki is the Principal of the School.  The IPAT is taught by faculty from the United States, including Dr. Fortunak and other individuals whose varied experiences in pharmaceutical R&D and manufacturing complement each other well.  The German organization GiZ (Deutsche Gesellschaft für Internationale Zusammenarbeiten) has provided support to build a pilot plant for pharmaceutical production at the SLF/KSP.  With support from the United Nations Industrial Development Organization (UNIDO) the IPAT has provided advanced training in pharmaceutical manufacturing and Current Good Manufacturing Practice (cGMP) to National Drug Regulators, University faculty, and pharmaceutical professionals since 2008.  With occasional courses being offered in a sequence either two or three times per year, approximately 120 participants have completed the core curriculum of four, two-week, full-time courses in drug discovery, development, GMP, and drug regulation.

 

Dr. Fortunak’s students (notably, Tiffany N. Ellison and Drs. Joseph Williams Jr. and Christopher L. King) have developed new instructional materials and taught at various IPAT courses in Moshi.  Dr. King was awarded an ACS GREET Fellowship (Graduate Research Experiences, Education, and Training) to support part of his work for the KSP. The research work done by these students has so far contributed to five publications and six invited presentations at various research symposia, including at the Gordon Research Conferences “Green Chemistry Conference” in Hong Kong (August, 2014).  Several African participants have also been able to visit Howard University as a result of these collaborations. One recent outcome from these collaborations has been the submission of a book chapter on “The Business Case for Green Chemistry in Drug Discovery” co-authored by Professors Fortunak and Simon Xiang of Howard University, and the African scientists Drs. Harriet Kamendi (Ghana) and Martins Emeje (Nigeria).

 

Tablet press 2.jpgThe IPAT program has recently divided its efforts in two directions. Purdue University (PU) is offering a Master’s degree to individuals who take additional, online courses and continue through a Purdue sequence. The original IPAT program continues, and the SLF/KSP efforts include transfer of the original program to other African Universities including the University of Ibadan in Nigeria.  These efforts are overseen by Dr. Fortunak.  Ibadan is also developing their own Master’s degree curriculum as part of this continuing collaboration with HU, and Howard is also helping the KSP to develop a Bachelor’s degree program in Industrial Pharmacy.

 

Synthesis-of-ACTs-at-KSP.jpgOther, exciting aspects of this collaboration have come into being since our last report.  In 2013 the United Nations ANDI (African Innovation for New Drugs and Diagnostics) Program designated the SLF/KSP as a Center of Excellence for drug training and manufacturing.  In 2013 the US FDA also taught a one-week Course in advanced topics for Abbreviated New Drug Applications (ANDAs, generic drug marketing) at the KSP. Participants from 19 African countries attended this training, overseen by (the late) Dr. Beverly Corey who until recently headed the US FDA/Africa. The SLF/KSP was distinguished with a US FDA Honor Award in 2013 for Excellence and Innovation in Regulatory Sciences for this Course In 2014 the SLF/KSP was also designated a Regulatory Center of Excellence (RCORE) in drug regulation by the African Medicines Harmonization program, an effort funded by the Bill and Melinda Gates Foundation. In 2013 Dr. Fortunak was also part of a Team award from the African Union (AU) for Social Responsibility. The AU represents the entire membership of fifty-four independent African nations.

 

Joe2.jpgAnd so, efforts continue on this fruitful collaboration. As Dr. Fortunak notes,“there is never enough funding” for work such as this.  The importance of this type of an approach to new science and technology is sometimes difficult to qualify for traditional research grant awards. Any readers who are interested in their organization possibly supporting these efforts are urged to contact Dr. Fortunak directly.This work carries both short-term and long-term rewards. Four African companies have used their IPAT training to good effect, and have manufacturing facilities that have been certified as cGMP-compliant by the US FDA and/or the World Health Organization “Pre-Qualification of Medicines Program.” Over the long term, the training of people contributes to economic development, job creation, and national independence and self-determination for creating access to medicines. The most rewarding part of these efforts is the personal interactions that result from international experience in training and in research.

 

Pictures:

1) KSP Pilot Plant, 2) Mount Kilimanjaro, 3) Tablet press at KSP Pilot Plant, 4) Synthesis of ACTs at KSP Pilot Plant, 5) Dr. Joeseph Fortunak with Sister Zita Ekeocha (Director, KSP IPAT Program) and Mr. Wilson Mlaki (Principal of KSP).

 

 

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The ACS Green Chemistry Institute® would like to thank the 43 corporations that worked collaboratively and non-competitively throughout 2014 to catalyze the integration of sustainable and green chemistry and engineering in the global chemical enterprise. Beginning in 2005 with just three companies on one Roundtable, there are now four Roundtables serving 43 members. The ACS GCI Industrial Roundtables are a proven concept, demonstrating that collaboration among peer companies can effectively provide value directly to the company, as well as to the collective industry, in designing more sustainable processes and products, a pursuit that is imperative for a sustainable business and environment.

 

Hydraulic Fracturing Roundtable

 

Building on efforts initiated in 2013 to create a Roundtable to improve the sustainability profile of hydraulic fracturing through green chemistry, in June 2014 the ACS GCI Hydraulic Fracturing Roundtable opened for membership. The group welcomed nine founding members: Apache Corporation, BASF, The Dow Chemical Co., The Lubrizol Corporation, Marathon Oil Company, Nalco Champion (An Ecolab Company), Rockwater Energy Solutions, Solvay USA Inc., and Trican Well Service. The appointed co-chairs are Danny Durham from Apache Corporation and Dave Long of the ACS GCI Board.

 

In partnership with Clean Production Action, members are provided 40 GreenScreen assessments of widely used fracturing chemicals (an $8,700 value). These assessments are able to be used internally by member companies to better determine the sustainability profile of their fracturing chemicals and identify where replacements might be needed. The newly formed Roundtable also organized a session at the 18th Annual Green Chemistry and Engineering Conference titled “Exploring Greener Approaches to Hydraulic Fracturing.” The session was chaired and organized by Danny Durham of Apache Corporation, and featured academic and industrial presentations on progress and improvements to fracturing chemicals. Moving forward in 2015, the Roundtable will establish annual goals supporting the strategic priorities including an analysis of data from hydraulic fracturing well reports.

 

Chemical Manufacturer’s Roundtable

 

Last year the Chemical Manufacturer’s Roundtable conducted a scouting survey to better understand the current implementation of green chemistry in the chemical manufacturing sector. In 2014, they published (in ACS Sustainable Chemistry & Engineering) the findings of a survey on the current implementation of green chemistry in the chemical manufacturing sector and identified actionable projects. Moving forward, the Roundtable seeks to evaluate how members can better highlight the process metrics they use, track green chemistry implementation across the industry, and define research, development, and demonstration needs for industrial application of green chemistry. A major focus area for the Roundtable is reducing the energy required to manufacture products. Building on the work to define opportunities for alternative separation technologies, the ACS GCI Roundtables (led by the Chemical Manufacturers), submitted a proposal for consideration for the NIST Advanced Manufacturing Technology Planning Grant.

 

The Roundtable also organized sessions at ACS GCI’s 18th Annual Green Chemistry and Engineering Conference in Bethesda, MD. “Greening the Supply Chain Using Biobased Chemicals” was organized by Paul Williams (Arizona Chemical) and Bogdan Comanita (Market Chemica on behalf of Penn A Kem). Alan Phillips (Arizona Chemical) chaired the session on-site. A tools and metrics related session was organized and chaired by Robert Giraud of DuPont. Throughout the year the Roundtable also hosted several distinguished guest speakers at their bimonthly meetings, including Ron Buckhalt (U.S. Department of Agriculture), Blandine Trouille (U.S. Department of Commerce), Nancy Jackson (U.S. Department of State), Rich Engler (U.S. EPA), and I.S. Jawahir (Institute for Sustainable Manufacturing at University of Kentucky). In May, a transition in Roundtable leadership occurred when Paul Williams’ (Arizona Chemical) term as co-chair came to a close, and Amit Sehgal of Solvay USA Inc. was voted in as the new co-chair.

 

Formulators’ Roundtable

 

In order to identify key industry needs for formulated consumer products, this year the Formulators’ Roundtable collaborated closely with Dr. Philip Jessop, Professor of Chemistry at Queen’s University and ACS GCI Board Member, on a manuscript defining opportunities for greener alternatives. The group identified 10 classes of components (such as chelants and sequestering agents, corrosion inhibitors, fragrance raw materials, and more) that are in need of replacement as well as the characteristics that ideal replacements should possess. The manuscript has been submitted for publication. Continuing discussions from 2013, the Roundtable acted as an industry voice, engaged the fragrance suppliers and developers, third party reviewers, and the U.S. EPA to enable informed discussions on the interim fragrance criteria and the design of more sustainable alternatives.

 

The Roundtable facilitated regular conversations with the U.S. EPA to learn about the current status of the Design for the Environment program, a hazard-based calculator being developed to assist fragrance houses and to stay abreast of the fragrance deadline, and several other topics. Furthermore, the Roundtable engaged with guest speakers at their bi-monthly meetings including:

  • Suzanne Hartigan (Director, Science Policy and Regulatory Affairs) and Megan Ekstrom (Manager, Government Affairs) of International Fragrance Association-North America to explore opportunities to collaborate in the development of greener products
  • Clive Davies, Joyce Parker, and Aly Lorenz of the U.S. EPA’s Design for the Environment Program Branch, provided an overview of their new criteria and calculator for fragrances. At the GC&E conference the Roundtable organized two sessions on defining greener and more sustainable consumer products. Chaired by Phil Sliva of Amway, the presentations featured industry professionals discussing topics ranging from hazard data transparency to life cycle assessment for greener products.

 

Pharmaceutical Roundtable

 

In its 9th year, the ACS GCI Pharmaceutical Roundtable continued to deliver on their four strategic priorities (inform and influence the research agenda, tools for innovation, education resource, and global collaboration) and welcomed a new member, Cubist Pharmaceuticals. David Leahy of Bristol-Myers Squibb completed his two-year tenure as a co-chair, and the group voted in John Tucker of Amgen as his successor.

 

This year several grants were awarded by the Roundtable to inform and influence the research agenda:

  • $100,000 to  Professor Paul Chirik of Princeton University for base metal-catalyzed cross-coupling in the pharmaceutical industry
  • $100,000 to Professor Neal Mankad of University of Illinois at Chicago for a bimetallic approach to iron-catalyzed coupling reactions
  • $50,000 to Professor Daniel Weix of University of Rochester for the synthesis of alkylated arenes and heteroarenes from the cross-coupling of heteroaromatic halides in non-amide solvents
  • $50,000 to Professors Matthias Beller and Elisabetta Alberico of the Leibniz-Institut für Katalyse for ligand-metal cooperative catalysis for the mild and selective synthesis of amines

 

The Roundtable also continued development on several of their established tools that can assist chemists, engineers, academics, students, and other professionals to incorporate greener chemistry into their research. The Biopharma team initiated a Process Mass Intensity benchmarking activity and collected best engineering practices. There were initial efforts to expand the solvent selection guide and fill data gaps in the existing guide. Furthermore, the reagent selection guide was enhanced, including the development of original reagent guides and the expansion of guides donated by member companies. These guides provide background on important transformations in the pharmaceutical industry, and evaluate potential reagents based on greenness, wide utility, and scalability.

 

Finally, in efforts to build and contribute to education resource, as well as collaborate globally, the Roundtable continued collaborations with the IQ Working Group to create training sessions in green chemistry for industrial chemists. The group also explored collaboration opportunities with IMI CHEM21 on an education and training work plan for students, industrial scientists and engineers, and other stakeholders. Another highlight was continuing a collaboration with a previous grant winner. Professor Neil Garg, as part of an extension of his 2012 Roundtable grant, published a manuscript on greener methodologies for Suzuki couplings in ACS Catalysis and an article highlighting the related undergraduate lab experiment in J. Chem. Ed. The Roundtable organized and chaired six sessions at the 18th Green Chemistry & Engineering Conference. The in-person meetings were held in Paris, France (hosted by Sanofi), Bethesda, MD (hosted by ACS GCI), and Rahway, NJ (hosted by Merck & Co., Inc.). All meetings were also web-based to assure global participation.

 

Roundtables at GC&E

 

Once again, in addition to hosting their in-person meetings and organizing technical sessions, all four roundtables sponsored and organized a poster reception in conjunction with the Annual Green Chemistry and Engineering Conference. In its fourth year, the ACS GCI Roundtable Poster Reception was a highly focused networking event with posters featuring a wide range of industrially relevant green chemistry work presented by industry professionals, professors, and students. Attendees consistently praise the reception as being “an excellent venue for interacting with individuals from all phases of the chemical supply chain” and to meet other professionals doing similar work. In each of the past four years the event has been held, over 72% of attendees have indicated they learned about a greener technology of potential relevance to their organization. Sponsors for the event were Florida Chemical Company, Inc. of Flotek, ILSI Health and Environmental Sciences Institute (HESI), and Launch.

 

 

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In the early 2000s, the director of the ACS Green Chemistry Institute®, Dr. Paul Anastas, initiated a discussion with the Dr. Berkeley “Buzz” Cue, a leader in green chemistry at Pfizer, about the possibility of starting a collaborative group that would work to catalyze the broader adoption of green chemistry and engineering in the pharmaceutical industry. These discussions turned into meetings, and in 2005 the ACS GCI Pharmaceutical Roundtable was established.

 

Ten years later the Roundtable looks back at an impressive set of accomplishments, and the roundtable concept has led to the establishment of three other ACS GCI roundtables—Formulators’ in 2007, Chemical Manufacturer’s in 2009 and Hydraulic Fracturing in 2014.

 

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Click on the infographic to see it in full size

 

"Since its creation in 2005, the ACS GCI Pharmaceutical Roundtable has been driving the development of innovative ‘green’ approaches to address some of the most important sustainability challenges in the manufacturing of pharmaceuticals," says Dr. Juan Colberg, Technology & Innovation, Pharmaceutical Sciences, Worldwide Research and Development, Pfizer and Co-Chair of the ACS GCI Pharmaceutical Roundtable.  "Over the last 10 years and through the Roundtable’s grant program, we have been able to make significant advancements such as greener solvent alternatives, less toxic catalytic conditions and biocatalytic transformations."

 

Some of the key accomplishments of the Roundtable include the development of a common solvent selection guide; a process mass intensity calculator and reagent guide; publication of an article outlining key research areas that has been cited 347 times and helped set the agenda for the Roundtable’s grant program (look for an update article later this year); $1.58 million dollars in grants awarded; and numerous publications, presentations and symposia.

 

"As we look ahead with our collaboration, the Roundtable will continue to sponsor exciting research and development in green alternatives," continues Colberg. "By working together, we can help develop processes that are more sustainable, environmentally sound and cost-effective."

 

 

This year, the Roundtable will be holding three events in honor of its anniversary:

 

Green Chemistry Makes a Difference: Innovations Leading to a More Sustainable Pharmaceutical Industry

The call for posters is open through February 28th for this one-day symposium to be held April 16, 2015, at F. Hoffmann-La Roche in Basel, Switzerland. Registration is free and limited, so if you are interested in attending, please register soon!

 

19th Annual Green Chemistry & Engineering Conference

The Roundtable is putting together a day-long symposium on green chemistry accomplishments in the pharmaceutical industry over the last 10 years and challenges on the horizon in North Bethesda, Maryland, July 14-16, 2015. Additionally, many other sessions of relevance to the industry will be featured. The call for papers remains open for these sessions through March 13, 2015.

 

Green Chemistry Makes a Difference: Pharmaceutical Industry/Academic Collaborations

The Roundtable will organize two sessions covering green chemistry organic chemistry topics at the 250th ACS National Meeting & Exposition in Boston during August 16-20, 2015.

 

Congratulations to the Roundtable! Current members include Amgen; AstraZeneca; Boehringer-Ingelheim Pharmaceuticals, Inc.; Bristol-Myers Squibb; Cubist Pharmaceuticals; Codexis; Dr. Reddy’s Laboratories Ltd.; Eli Lilly and Company; F. Hoffman-La Roche Ltd.; GlaxoSmithKline; Johnson & Johnson; Merck & Co., Inc.; Novartis; Pfizer Inc.; Sanofi and ACS GCI.

 

Find out more athttp://www.acs.org/gcipharmaroundtable

 

 

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This month we have dedicated The Nexus to green chemistry and public health, and at the nexus of these issues is the pharmaceutical industry and their innovation processes. As an industry dedicated to developing products that can save people’s lives, typically the primary priority in the innovation process has been ensuring that the drug works rather than guaranteeing that the synthesis will lead to the most efficient or safest possible manufacturing process. Therefore what often goes unrecognized in the drug discovery phase is that huge amounts of waste can be generated in pharmaceutical production processes, and that waste (including volatile organic solvents) can be toxic or difficult to manage. With nearly 25-100 kg of waste being produced for each kilogram of drug in a pharmaceutical plant’s optimized process (a metric known as process mass intensity), there is much room to reduce the impact of the manufacturing process on public health and the environment.

 

Greener chemistry and engineering is an upstream approach to addressing waste, pollution, and resource issues through toxicity reduction, biodegradability, energy efficiency, and more. For 20 years, the U.S. Environmental Protection Agency (EPA) has sponsored the Presidential Green Chemistry Challenge Awards (PGCCA), in partnership with the American Chemical Society, and it is the premier recognition for sustainable innovation in chemistry. Five awards are given every year to highlight greener groundbreaking science in the chemical enterprise. Winners are chosen if their developments reduce waste, improve efficiency, are commercially viable, and are equally or more cost effective. Over the past two decades the pharmaceutical science has been one of the more active sectors in this sphere, having received 11 awards thus far.

 

At the time of the inception of the award some companies were beginning to green their pharmaceutical processes, but there was no comprehensive strategy across the industry to understand their relative waste footprint or incorporate greener practices. Most improvements were driven by Manufacturing or Environmental Health & Safety departments, rather than Research & Development. While there many instances of more sustainable processes prior to the mid-1990s, one of the most widely cited examples of greener chemistry is the first pharmaceutical PGCCA recipient in 1997—BHC Company (now BASF Corporation) and their virtually waste free synthesis of Ibuprofen (an active ingredient in many over-the-counter pain relievers). The original process required six stoichiometric steps and wasted more than half of the material introduced in the process. The greener innovation generated the same active ingredient but required only three catalytic steps, doubled the utilization of the inputs, and introduced a byproduct recovery step.

 

By 2005, after 10 years of the PGCCA, four more awards had been given in the pharmaceutical industry. Lilly Research Laboratories (1999) eliminated huge amounts of chromium and solvent waste from an epilepsy drug process, and in 2000 Roche Colorado Corporation (now CordenPharma Colorado) removed two hazardous waste streams and 11 materials from their process for an antiviral agent (Cytovene) for immune-compromised patients (including those with AIDS). Pfizer (2002) transformed their process for the active ingredient in Zoloft (a depression treatment) that dramatically reduced waste and solvent use, and doubled their yield, and Bristol-Myers Squibb (2004) created an alternative synthetic approach to Paclitaxel (active ingredient in the cancer drug, Taxol) so that it no longer needed to be harvested from the ecologically sensitive Pacific yew tree.

 

Beyond the awards, green chemistry activity was continuing to build in the industry. Pfizer had developed an in-house and cross-departmental green chemistry program and this model began to be replicated by other major players in the industry. Furthermore, it was at this time that the ACS Green Chemistry Institute founded the Pharmaceutical Roundtable. Eli Lilly, Merck & Co., Inc., and Pfizer were the initial members and the mission of the group was to catalyze the implementation of green chemistry and engineering in the global pharmaceutical industry. They came together to identify critical challenges faced by the industry and created strategic priorities to address them (informing and influencing the research agenda, creating tools for innovation, engaging as an education resource and collaborating globally).

 

Now, after 20 years of PGCCA, most major pharmaceutical companies are adopting green chemistry in some fashion and are incorporating greener practices in their drug discovery stage so that their processes are safer and the final products can be scaled more efficiently.  The ACS GCI Pharmaceutical Roundtable has 15 members (and growing), and these are the companies that are dominating the PGCCA. Three more industrial pharmaceutical awards have been given; two exclusively to Merck & Co., Inc. (in 2005 and 2006), one to Codexis, Inc. (2006), and one to both companies for a collaborative innovation (2010)—both companies are Roundtable members. As academic-industrial partnerships became even more of a goal in the industry, we have started to see notable academic developments with commercial potential. In 2012, Codexis, Inc. collaborated with Professor Yi Tang from University of California, Los Angeles to create a single-step biocatalytic process to synthesize simvastatin (a cholesterol drug). And just last year, Professor Shannon Stahl of the University of Wisconsin-Madison won for his aerobic oxidation developments for pharmaceutical synthesis, which utilize oxygen from air to oxidize through a new catalytic, mild condition, and highly selective method (replacing the need for hazardous inputs such as chlorinated solvents).

 

There has been dramatic growth in green innovation in the pharmaceutical industry, and from discovery to scale, it is clear to see that the chemistry done at every phase of drug development has huge implications for public health and the sustainability of the industry. There have been many successes and increased adoption throughout all aspects of companies’ processes, but there are still huge gains to be made. Improvements to process mass intensity are still needed, the dominance of batch processes over flow chemistry holds strong, and the inclusion of generic companies in this green paradigm has yet to fully blossom. There are some companies who are starting to work with suppliers to integrate green chemistry throughout their supply chain, but it is not yet the norm. Outsourcing of the drug discovery phase is growing in the industry, so increasingly a company strategy focused on green and sustainable innovation is needed, as well as continued partnerships with academia to further the research agenda. With these needs, we can surely expect the continuation of green developments in the pharmaceutical industry and we can count on the PGCCA to keep recognizing the top innovators who can deliver on these needs—keep an eye out this summer, when the 2015 PGCCA awards are announced in July to see the next wave of innovation and learn how their science can change the world.

 

 

 

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ACSGCI

Message from the Director

Posted by ACSGCI Feb 18, 2015

Contributed by David Constable, Director, ACS Green Chemistry Institute®

 

In late January I had the opportunity to attend the LAUNCH forum. In case you are not familiar with LAUNCH, you can find out more about it here.  This year the LAUNCH partners developed a green chemistry challenge and through a well-established process identified 10 innovators to participate in this year’s forum. These 10 innovators started by making a pitch to the LAUNCH council members in attendance and then rotated from group to group to solicit feedback. The purpose of bringing the innovators and the council together was to provide the innovators with connections to people and potential resources that might assist with moving their business forward. It’s really a simple process when you break it down, and it provides a great opportunity for innovators to extend their reach in a short period of time.

 

Being a part of the entire process brought home, once again, the difficulty in moving an innovation from proof of concept to commercialization. It seems to me that many think that when an innovation is “green,” it’s harder to move that kind of innovation forward than it is to move a “normal” innovation into the marketplace. Conversely, there are some who believe that because an innovation is “green,” it should enjoy either a price premium, or it will somehow be more attractive to investors, banks, etc. The reality is that any innovation in the chemical and allied industries is difficult to commercialize, and one should never bank on a price premium for something they think is greener or more sustainable than an existing product. Markets are markets and they’re pretty unforgiving. And while game-changing innovations are more likely to make it, there are no guarantees that they will.

 

I can’t highlight all the innovations that were presented but I thought I would highlight a few that I think are worth watching.  First is Grow Plastics, a relatively simple innovation that lightweights a plastic item such as a cup, bowl, plate, a meat tray, etc., while still providing higher performance at a competitive cost to a plastic such as styrofoam.   The fact that Grow Plastics uses PLA and no plasticizers is a definite “green” advantage, but what will capture the market is price and performance.  Establishing and growing the market in the Northwest U.S. makes a lot of sense given moves to ban styrofoam.

 

Next is Bioamber, a company that is looking to produce succinic acid through sugar fermentation utilizing a modified yeast. Some might argue that yeast is a better platform than what close competitor Myriant uses, but both companies face an uphill battle in getting chemists to begin using succinic acid to create new chemicals and polymers. They also need to demonstrate that they have a reliable supply chain and can supply the volumes at the desired quality. The interesting thing is that despite examples of higher performance or the development of a more desirable property (hardness, durability, softness, etc.) of new molecules utilizing succinic acid both companies still face the uphill battle of displacing an existing product and supply chain that is tried, tested and has customer approval.

 

Next there is Ancatt, a potentially disruptive anti-corrosion technology that doesn’t use Cr or Zn. Ancatt was an ACS GCI Business Competition winner in June of 2012 and their technology has all the appearances of being a winner. The challenge here is for the company to find a trusted partner to help move this from limited concept demonstrations to widespread commercial use. It is challenging for any innovator to move from the laboratory to pilot and full-scale production, and in an entrenched industry like the painting and coatings industry, there isn’t a simple or clear path. Like many other technologies, breaking into a low-margin commodity business is extraordinarily challenging, no matter how disruptive the technology.

 

Finally, there is Mango Materials, a company that is looking to make a biodegradable plastic, PHA, from waste methane at wastewater treatment plants. There are a variety of issues with moving this from demonstration to scale, but it appears that Mango Materials is making good progress. It is exciting to see waste methane that is generally not being well utilized at the moment and converting it into a plastic that is biodegradable without the higher temperature composting requirements of PLA.  PHA still has a number of uphill battles as a plastic, but Mango Materials appears to have identified a commercial use that represents a great starting place for establishing a market and a steady cash stream that they can build on and diversify into other markets. If they manage to sort out the pilot plant funding, I think we can expect great things from them in the future.

 

It is always great to see innovations and innovators who are making inroads towards implementing green chemistry and engineering in business. I remain optimistic that these companies will make great progress and have a very positive impact on the world. I hope to see this trend accelerate.

 

As always, please do let me know what you think.

 

David_Signature.png

 

 

 

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Contributed by Marie Bourgeois PhD, MPH Research Assistant Professor Center for Environmental/Occupational, Risk Analysis and Management Department of Environmental and Occupational Health, University of South Florida College of Public Health

 

For decades, the development of new chemicals has outpaced our ability to adequately assess risks potentially posed by exposure. Permissible Exposure Limits (PELs), set by OSHA to protect the health of America’s workforce, are a great example of the existing backlog. Fewer than 600 PELs have been established for common industrial chemicals. However, the Chemical and Product Categories database (CPCat) has catalogued over 40,000 chemicals currently used in different consumer products. While every effort is made to assure the safety of these chemicals, toxicity information is limited or absent for the majority of these compounds. Traditional testing methods are time consuming, expensive, heavily reliant on laboratory animals and frequently limited in scope. Stakeholders all agreed it was time for a new approach.

 

In 2007, the National Academies published ‘Toxicity Testing in the 21st Century’. This report highlighted the shortcomings of traditional testing methods, advocating a shift from whole animal based testing, to ‘toxicity pathway’ cellular and tissue based testing. It also stressed the utility of dose-response extrapolation of cellular response to toxicants to potential adverse effects in human systems. Report authors recommended continued use of real world data including biomonitoring results from projects such as NHANES. Perhaps most importantly, the report described an adaptive approach to risk assessment that stressed placing risk in context; some risks require rapid testing results from a single environmental agent while others may need a multitude of chemicals screened. Restricting testing to the most hazardous compounds is an economical approach to minimize adverse human health effects. The effort to modernize testing required the development of new tools.

 

ToxCast and similar tools provide methods of predictive toxicology suitable for the 21st century. ToxCast, or Toxicity Forecasting, is part of the US Environmental Protection Agency’s National Center for Computational Toxicology (EPA/NCCT) Research initiative to generate bioactivity profiles for chemicals posing the greatest risk to human health. ToxCast uses multiple in vitro assays to predict in vivo effects. Phase I profiled 320 chemicals as a ‘Proof of Concept’ in 2009. These chemicals were chosen because decades of existing data in the literature permitted validation via one to one comparison. Well correlated experimental results derived from the approximately 500 in vitro assays and 75 in vivo endpoints demonstrated the reliability of the ToxCast methodology. Phase II examined 2000 chemicals from categories including food additives, ‘green alternatives’ to existing industrial chemicals, nanomaterials and consumer products that were never released. The testing utilized 700 high throughput screening (HTS) assays running the gamut of cellular responses and signaling pathways.

 

ToxCast chemical data is publicly available via Interactive Chemical Safety for Sustainability Dashboards (iCSS). Other CompTox tools and resources include ACToR (Aggregated Computational Toxicology Resource), ToxRefDB (Toxicity Reference Database), DSSTox (Distributed Structure- Searchable Toxicity Database), ExpoCast (Exposure Forecaster) and Virtual Tissues. These tools provide searchable toxicity testing results, access to thirty years of animal studies, structural information, exposure predictions and virtual tissue models that map existing research to computer simulations of expected effects using an adverse outcome pathway approach. ToxCast data also becomes part of Tox21.

 

Tox21, as the collaboration between the EPA, National Institute of Environmental Health Sciences (NIEHS)/National Toxicology Program (NTP), National Center for Advancing Translational Sciences (NCATS)/NIH Chemical Genomics Center (NCGC) and the U.S. Food and Drug Administration (FDA) became known, utilizes robotic technology to conduct HTS of chemicals of interest.  HTS shortens test times required for data generation by covering a large range of test concentrations using 1536 well microtiter plates. Tox21 currently screens approximately 10,000 chemicals using biochemical and cellular HTS assays.

 

The overall goals of ToxCast/Tox21 include creating and screening a large library of chemicals, the creation of HTS assays for pathways, linkage of HTS results to adverse human health effects and identification of toxicity pathways. ToxCast/Tox21 runs multiple assays per target and multiple targets per pathway to develop a prioritization index (ToxPi) for each chemical.

 

     ToxPi = f(HTS assays + Chemical properties + Pathways)

 

In the future, additional information on exposure, chemical properties or QSAR models may also be incorporated.

 

     ToxPi = f(Exposure + Chemical properties + In vitro assays + Pathways)

 

The EPA formed partnerships with academic, industrial and governmental agencies to revolutionize toxicity and risk assessment. ToxCast data is currently being used by screening programs in Endocrine Disruption, Toxic Substances Control Act and Safe Drinking Water Act to prioritize chemical testing and set contaminant candidate lists.

 

So what does this mean to the average public health toxicologist? A risk assessment typically proceeds in 4 steps: hazard identification, generation of dose-response data, exposure assessment and risk characterization. Simply put, ToxCast/Tox21 moves the starting line up. A toxicologist looking for information on a priority chemical can begin with any one of these databases. They might check to see if a priority index had been established for their chemical(s) of interest. They could check Tox21, ToxRefDB, ToxExpo and iCSS for previously run in vivo studies and exposure assessments. A toxicologist could even use the virtual tissue models to predict adverse outcomes. This information may not obviate the use of research animals but it should lead to more informed experimental designs. Armed with this data, toxicologists everywhere will be better prepared to design a study that answers their objectives.

 

For more information:

 

ToxCast: http://epa.gov/ncct/toxcast/

ToxCastDB: http://actor.epa.gov/actor/faces/ToxCastDB/Home.jsp

ACToR: http://actor.epa.gov/actor

ToxRefDB: http://actor.epa.gov/toxrefdb

CSS Dashboards: http://actor.epa.gov/actor/faces/CSSDashboardLaunch.jsp

CompTox Tools: www.epa.gov/comptox

Chemical Safety for Sustainability Research Program: www.epa.gov/research/chemicalscience

ExpoCast: http://www.epa.gov/ncct/expocast/

CPCat: http://actor.epa.gov/cpcat/faces/home.xhtml

Virtual Liver: www.epa.gov/ncct/virtual_liver

Virtual Embryo: www.epa.gov/ncct/v-Embryo

ToxCast and Tox21: High Throughput Screening for Hazard & Risk of Environmental Chemicals: http://www.toxicology.org/isot/rc/nlsot/docs/Dix.pdf

 

References:

 

Dix et al (2006) “The ToxCast Program for Prioritizing Toxicity Testing of Environmental Chemicals.” Toxicological Sciences.

 

Judson et al. (2010) “Analysis of Eight Oil Spill Dispersants Using Rapid, In Vitro Tests for Endocrine and Other Biological Activity" Environmental Science and Technology.

 

Reif et al. (2010) “Endocrine Profiling and Prioritization of Environmental Chemicals Using ToxCast Data.” Environmental Health Perspectives.

 

Rotroff et al (2010) “Incorporating Human Dosimetry and Exposure into High Throughput In Vitro Toxicity.” Toxicological Sciences.

 

 

 

“The Nexus Blog” is a sister publication of “The Nexus” newsletter. To sign up for the newsletter, please email gci@acs.org, or if you have an ACS ID, login to your email preferences and select “The Nexus” to subscribe.

 

To read other posts, go to Green Chemistry: The Nexus Blog home.

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