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Contributed by Malka Doshi, Green Relations Officer, Green ChemisTree Foundation

 

The ACS Green Chemistry Institute is once again partnering with the Green ChemisTree Foundation, India for the 5th Industrial Green Chemistry World (IGCW-2017) Convention and Ecosystem, scheduled on October 5-6, 2017 in Mumbai, India.

 

The IGCW Convention series is uniquely designed around the central theme of Profitability from Industrial Green Chemistry and Engineering. Since 2009, four biennial IGCW Conventions have seen a growing number of industry stakeholders of both national and international repute converge in Mumbai.

 

The IGCW ecosystem brings together key stakeholders in the Indian chemical industry – including senior government officials, chief decision-makers from industry, green chemistry and engineering experts, solution-providers, and research organizations – on a common platform with a single agenda to accelerate the implementation of green chemistry and engineering practices in India.

 

The 5th IGCW-2017 marks the completion of the “GC&E Awareness phase” in India and propels the start of the “GC&E Implementation phase.” In this broader context, IGCW-2017 has expanded its scope and structure to incorporate subject-specific themes across the two-day convention that will be explored during the nine following concurrent events:

 

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  • The IGCW Symposium showcases the IGCW Convention & Ecosystem’s mission by bringing together the world’s best industrial practices and success stories on green chemistry and engineering.

  • The SERB-IGCW Awards collaborate with the Department of Science & Technology of the Government of India to highlight outstanding initiatives in green chemistry and engineering  launched by industry, start–ups, and the knowledge community.

  • The IGCW-EXPO will bring together 40+ technology providers from all over the globe that offer green chemistry and engineering solutions needs of  the Indian chemical industry.

  • The IGCW-PCB Conference will feature talks by senior representatives of the State and Central Pollution Control Boards to explore their roles in the implementation of green chemistry and engineering practices to facilitate pollution prevention.

  • The IGCW-FSC Flow Chemistry Workshop seeks to expand awareness and understanding of flow chemistry technologies and their applications.

  • IGCW-GC&E Emerging Tools & Technologies is integrated into the IGCW ecosystem with the objective to provide a platform for participating companies to gain a first-hand understanding of emerging tools and technologies with respect to their  green chemistry and engineering applications.

  • The ACS GCI Pharmaceutical Roundtable (GCIPR) Workshop on Solvent & Reagent Selection Guide will be conducted by experts from the ACS GCI Pharmaceutical Roundtable (GCIPR), focused on accessing the solvent and reagent selection guide and other green chemistry and engineering tools as developed and used by GCIPR member companies.

  • The IGCW 1800 seminars are subject-specific seminars on relevant topics related to the industrialization of green chemistry and engineering applications. The selected topics are: Green Processes, Green Catalysts, Green Solvents & Green Engineering.

  • The IGCW CSIR Industry Workshops  will connect the Council of Scientific & Industrial Research (CSIR) Lab’s green-chemistry-and-engineering-related projects to senior representatives in the chemical industry. CSIR scientists will share success stories, present potential collaborative models, and showcase subject-specific competencies.

 

For more details on IGCW-2017, or to learn how you can get involved, please email connect@industrialgreenchem.com.

 

 

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Despite the wide variety of chemistry conducted as part of drug discovery and development and the undoubted ingenuity of the chemists conducting the research, the majority of reactions still fall into a relatively small number of categories.

 

With this in mind, chemists in the industry have previously sought[i],[ii] to offer guidance that both encourages chemists to use greener reagents by first intent and provides a simple, easy-to-use reference for greener alternatives to be considered when reactions are repeated and/or scaled up.

 

More recently, the ACS GCI Pharmaceutical Roundtable has brought together contributions from multiple pharmaceutical companies to provide a more comprehensive set of reagent guides that you can find at http://www.reagentguides.com/.

 

Guides are freely available for 11 transformations: oxidation to aldehyde and ketones, nitro reduction, N-alkylation, O-dealkylation, ester deprotection, epoxidation, Boc deprotection, amide reduction, bromination, reductive amination, and metals removal.

 

Additional guides on Buchwald-Hartwig amination, iodination and chlorination are currently only available to members of the Pharmaceutical Roundtable, but are scheduled to be rolled out to a wider audience soon. The Roundtable will be developing and releasing additional guides over time.

 

A tutorial on the guides is available here: https://youtu.be/w05iq4VcPts

 

venn-large.pngEach circle of the Venn diagram represents a different criterion –  those being ‘scalability,’ ‘greenness’ and ‘wide utility.’

 

The ideal reagent will have all three characteristics and appear in the middle (green area) of the Venn diagram, whereas some reagents have one of the traits but none of the others or a mix of two but not the third.

 

Placement within the Venn diagram can change with many variables, including solvent, catalyst, treatment of wastes, etc.

 

Good green chemistry requires the chemist to look across a range of factors before making the best choice. With the inclusion of information like atom efficiency, ecotoxicology/toxicology profiles, safety issues, waste products, sustainable feedstocks and more, we hope these guides give promotion to some reagents as compared to others. A  holistic approach is encouraged, however. For example, if a ‘greener’ reagent gives a much lower yield or requires multiple steps, the overall benefit may be outweighed (i.e., it may give rise to a higher footprint in the wider context) compared to an initially less ‘green’ reagent.

 

DISCLAIMER

The American Chemical Society Green Chemistry Institute’s Pharmaceutical Roundtable (“the Roundtable”) has created this Reagent Guide to inform and guide users toward greener reagents for various chemical transformations. The Roundtable has used reasonable efforts in collecting, preparing and providing quality information and material, but does not warrant or guarantee the accuracy, completeness, adequacy or currency of the information contained in the Reagent Guide. By downloading, viewing and utilizing information from the Reagent Guide, visitors assume full responsibility for their own actions and any damages or liabilities that may result from the utilization of information obtained from the Reagent Guide. Should you have any questions or comments about the Reagent Guide or this disclaimer, please send an e-mail to gcipr@acs.org.

 


[i] Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation

K. Alfonsi, J. Colberg, P. J. Dunn,* T. Fevig, S. Jennings, T. A. Johnson, H. P. Kleine, C. Knight, M. A. Nagy, D. A. Perry*, M. Stefaniak. Green Chem. 2008, 10, 31–36.

 

[ii] Development of GSK’s Reagent Guides – Embedding Sustainability into Reagent Selection

J. P. Adams, C. M. Alder, I. Andrews, A. M. Bullion, M. Campbell-Crawford, M. G. Darcy, J. D. Hayler, R. K. Henderson, C. A. Oare, I. Pendrak, A. M. Redman, L. E. Shuster, H. F. Sneddon,* M. D. Walker. Green Chem. 2013, 15, 1542-1549.

 

 

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Contributed by Mary M. Kirchhoff, Ph.D., Director, ACS Green Chemistry Institute®; Executive Vice President of Scientific Advancement, ACS

 

Summer is always a busy season for the ACS Green Chemistry Institute® (GCI), and this year was no exception. My colleagues and I enjoyed seeing so many of you in June at the 21st Annual Green Chemistry & Engineering Conference. Your feedback on the technical symposia, networking events and poster sessions in Reston are already helping to shape next year’s conference, which is being chaired by Julie Haack from the University of Oregon and Richard Blackburn from the University of Leeds. The 22nd Annual Green Chemistry & Engineering Conference will be returning to Portland, Oregon from June 18-20, 2018.

 

The Summer School on Green Chemistry and Sustainable Energy was held the week following the conference at the Colorado School of Mines. Fifty-three graduate students and postdoctoral scholars from the U.S., Canada and Latin America participated in the week-long program. Participants presented their research during poster sessions, engaged in lectures on specific topics in green chemistry and sustainable energy, and conducted a modified Life Cycle Analysis to determine the “greenest” pathway toward a target molecule. Presentations on careers, publishing, and proposal writing rounded out the week – along with a white water rafting trip.  The program is supported by a generous grant from the ACS Petroleum Research Fund.

 

I was thrilled to attend last month’s Green & Sustainable Chemistry (GSC-8) Conference in Melbourne, Australia. The conference was part of the Royal Australian Chemical Institute’s Centenary Congress, an event that encompassed nine conferences and engaged approximately 3,500 attendees, making it the largest chemistry conference ever held in Australia! The GSC-8 Conference was highly international, with plenary talks delivered by scientists from Australia, Canada, China, Israel, Japan, the UK and the US. I am delighted that the next Green and Sustainable Chemistry Conference (GSC-9) will be held in 2019 in conjunction with the 23rd Annual Green Chemistry & Engineering Conference in Reston, Virginia.

 

We are now finalizing preparations for the ACS National Meeting, which begins in Washington, D.C., this week. Numerous symposia feature green chemistry talks, and I encourage you search the program by topic (green chemistry) to identify symposia of interest to you. We look forward to seeing you in Washington over the coming week!

 

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Contributed by Samy Ponnusamy, Ph.D., Fellow, Green Chemistry, MilliporeSigma; and Jeffrey Whitford, Head of Corporate Responsibility and Branding, MilliporeSigma

 

Picture1.pngSummary: MilliporeSigma created a unique, web-based greener alternative scoring matrix, also known as DOZN: a quantitative green chemistry evaluator based on the 12 principles of green chemistry. The 12 principles of green chemistry provide a framework for learning about green chemistry and designing or improving materials, products, processes and systems. DOZN scores products based on metrics for each principle and aggregates the principle scores to derive a final aggregate score. The system calculates scores based on manufacturing inputs, Globally Harmonized System (GHS) and Safety Data Sheet (SDS) information, which provide a green score for each substance. DOZN is flexible enough to encompass the diverse portfolio of products, ranging from chemistry to biology-based products. The DOZN system has also been verified and validated by a third party to ensure best practices are applied, and a peer reviewed paper has been published on it recently. This new greener chemistry initiative offers customers an increased breadth of greener alternative products with confirmatory documentation to validate greener characteristics.

 

Introduction: Green chemistry is the concept of developing chemical products and processes that minimize the use and generation of hazardous substances, reduce waste, and reduce demand on diminishing resources. Paul Anastas and John Warner developed the foundation that has served as the global framework of green chemistry. That framework proposes 12 complementary principles around resource efficiency and risk (human health and environmental) minimization and targeting a life-cycle perspective (e.g., raw materials extraction, chemical production, and end-of-life bioaccumulation and biodegradation). Ultimately, these 12 principles were adopted by American Chemical Society (ACS) Green Chemistry Institute (GCI).

 

The 12 principles are only conceptual and do not provide a quantitative framework. While various approaches to quantifying greener processes and products have been proposed, there is no unifying set of metrics in place. After a review of the current state of green chemistry methods, MilliporeSigma developed DOZN, a quantitative green chemistry evaluator, and leveraged generally accepted industry practices.

 

Quantitative Green Chemistry Evaluator:

 

The design objectives developed by MilliporeSigma industrial chemists included the following:

 

  1. Allow for direct comparison between alternative chemicals considered for the same application as well as direct comparison between alternative synthesis manufacturing processes considered for the same chemical product.
  2. Allow transparent comparison against each of the 12 principles and for each of the three major stewardship categories: resource efficiency, human health and environmental hazard, and energy use.
  3. Provide sufficient flexibility to apply to the diverse product portfolio.
  4. Be inexpensive to implement by utilizing readily available data.
  5. Be based on generally accepted industry practices when available.
  6. Be easy to communicate the method and results to customers.

 

Considering these guiding elements, we investigated and designed an approach to evaluate and score chemical products and processes on each of the 12 principles.

 

Categories: DOZN groups the 12 principles into like categories, allowing for a focus on overarching green chemistry categories of hazard, resource use and energy efficiency. These category groupings and scores are shown in Table 1:

  • Improved resource use
  • Increased energy efficiency
  • Reduced human and environmental hazards

 

Greener Alternatives Example Results:

 

Table 1

Category and Related Principles

Old

1-Aminobenzotriazole Process

Re-engineered –

1-Aminobenzotriazole Process

Principle Score

Principle Score

Improved Resource Use

Principle 1: Prevention

2701

1042

Principle 2: Atom Economy

933

345

Principle 7: Use of Renewable Feedstock

933

345

Principle 8: Reduce Derivatives

0.0

0.0

Principle 9: Catalysis

0.5

1.0

Principle 11: Real-Time Analysis for Pollution Prevention

1.0

1.0

Increased Energy Efficiency

Principle 6: Design for Energy Efficiency

3282

1322

Reduced Human and Environmental Hazards

Principle 3: Less Hazardous Chemical Synthesis

3358

1455

Principle 4: Designing Safer Chemicals

5.0

5.0

Principle 5: Safer Solvents and Auxiliaries

2245

1252

Principle 10: Design for Degradation

0.0

0.0

Principle 12: Inherently Safer Chemistry for Accident Prevention

2516

220

Aggregate Score*

100

44

*Aggregate Score is calculated by averaging each category’s scores and summing three category scores to get the single score. Then this will be further normalized (divided by 50) to get an aggregate score from zero to 100 scales (zero being the most desired).

 

The GCM is advantageous over existing approaches because it provides metrics that are (1) inexpensive to implement with readily available data, (2) based on generally accepted industry practices when available, and (3) easy to communicate, both method and results, to customers. Sustainability programs that implement the proposed approach should anticipate the following benefits:

  • Measurement: Ability to use on-hand data sources or establish straightforward data collection programs
  • Calculations: Ability to utilize well-defined metrics to calculate the benefits of the 12 principles of green chemistry
  • Communication: Ability to transparently communicate greener alternatives to customers

 

Based on the feedback from customers, MilliporeSigma is currently working on expanding DOZNsystem (DOZN2.0) so customers can screen their products/processes to get DOZN scores. This would help our customers select the greener products for their research/manufacturing to promote sustainability.

 

 

“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 Juan Colberg, Green Chemistry Leader/Senior Director of Chemical Technology, Pfizer; Javier Magano, Principal Scientist, Pfizer; and John Wong, Research Fellow, Pfizer

 

2012 marked the 10-year anniversary of Pfizer’s Green Chemistry Program, a program that focuses on education, innovation, solvent and waste reductions, the use of safer chemistry, greener processes, cost savings, and colleague engagement. Now, five years on from the 10-year anniversary, our Green Chemistry Program continues to promote, internally and externally, the selection and use of environmentally preferable chemicals, eliminating waste and conserving energy in our chemical processes.

 

As Pfizer’s portfolio evolves, so does its Green Chemistry Program. Efforts are not narrowly focused on small molecules for the Pfizer Innovative Health portfolio, but broadly include Biopharma and the Essential Health portfolios as well. An important part of the program’s success has been the commitment from Pfizer to provide and support the creation of ways to share knowledge, best practices and techniques across the organization, as well as educating future chemists and engineers in colleges and universities.

 

As part of these efforts, we have engaged our internal and external communities with a series of educational workshops to promote the application of green chemistry principles and the use of more environmentally sustainable technologies and approaches.

 

Green Chemistry Workshops at Pfizer

 

Education is one of the key elements of Pfizer’s Green Chemistry Program. Recognizing the importance of green chemistry education, Pfizer has hosted or participated in at least one workshop annually beginning in 2003.

 

From 2003 to 2006, workshops were held at the Pfizer R&D site in Groton, Connecticut. These workshops, titled “Sustainable Chemistry in the Pharmaceutical Industry,” began with a reception and dinner on the first day and featured a keynote address. The second day was a full day featuring presentations and interactive breakout sessions.

 

John Warner was an important participant in these workshops and presented “The 12 Principles of Green Chemistry: From Philosophy to the Flask.” Pfizer colleagues gave presentations on various topics involving the application of green chemistry in the development of Pfizer drugs. The breakout sessions gave students the opportunity to apply their knowledge of green chemistry to case studies based on Pfizer drugs. For instance, the case studies presented during the breakout sessions in 2004 were based on sertraline and sildenafil, the active pharmaceutical ingredients in Zoloft® and Viagra® respectively.

 

Participants in the workshops were selected from colleges and universities in the Northeast. Participation in 2004 was similar to the other years in which this workshop was conducted and included 28 students from 13 institutions in six states (Connecticut: Connecticut College, UCONN, University of St. Joseph; Massachusetts: Bridgewater State, UMASS Amherst, UMASS Boston, Gordon College, Simmons College, Suffolk University, Worcester Polytechnic Institute; New Hampshire: University of New Hampshire; Rhode Island: University of Rhode Island; Vermont: University of Vermont). Overall, these workshops hosted at the Pfizer R&D site in Groton were well received based on feedback from students. Notably, two participants from the 2004 workshop became Pfizer colleagues.

 

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Pfizer has also promoted green chemistry education outreach activities in other sites across the U.S. and Europe.

 

Workshop on Wheels (WOW)

 

With the great success of the Pfizer green chemistry workshops hosted in Groton, we decided to expand the program by engaging faculty members and reaching students from a broader range of disciplines. In 2007, the Groton Green Chemistry Team conceived the “Workshop on Wheels (WOW),”in which the workshop was set to be conducted at a college or university with a small team of Pfizer colleagues. An important element of “WOW” was the active engagement of faculty and students in organizing and conducting these workshops.

 

The first “WOW” was held at the University of Puerto Rico in 2007, hosted by Professor Ingrid Montes (currently Director-at-Large, ACS Board of Directors), followed by one in UCONN hosted by Professor Amy Howell. Since 2007, Pfizer has partnered with nine institutions (Boston University, Harvard University, Northeastern University, UMASS Boston, University of Rhode Island, Wesleyan Univeristy, Worcester Polytechnic, and Yale University) to bring “WOW” to their campuses. The “WOW” held at UMASS Boston in 2016 is the subject of a previous Nexus article.

 

Pfizer remains committed to green chemistry education and is planning a return trip to University of Rhode Island for its 2017 “WOW,” hosted by Professor Brenton DeBoef.

 

Workshop Focus Shifting to New, Greener Technologies

 

While the format of Pfizer’s green chemistry workshops has remained consistent, with presentations by Pfizer colleagues and invited speakers as well as an interactive breakout session, the focus of the topics has shifted from a basic application of the 12 Principles to applications of novel, greener technologies.

 

Thus, the last few years have seen the development of a number of talks by green chemistry team colleagues that cover diverse and increasingly important areas of chemistry, leading to more environmentally benign processes that have become some of the workshop attendees’ favorite topics.

 

  • Biocatalysis: The use of enzymes in drug manufacturing has seen a resurgence in recent years thanks to enzyme engineering, resulting in highly-active and versatile biocatalysts that enable highly efficient processes. In addition, due to the chiral nature of enzymes, these catalysts are particularly well-suited for the generation of chiral centers in the products, which is of special interest in the pharmaceutical industry. A great example that is analyzed by the attendees of the “WOW”breakout sessions is a route to pregabalin (LyricaTM), in which the enzyme is used to resolve a diester. This then allows for the separation of the compound with the desired chirality leading to pregabalin, whereas the compound with undesired stereochemistry undergoes racemization and can be recycled and fed back into the process with the consequent improvements in yield and waste reduction. Another outstanding example of biocatalysis application that is presented is the synthesis of the side chain of statins, such as Lipitor, which replaced the original reduction to generate a stereocenter using toxic and pyrophoric chemicals.

  • Flow chemistry: Most of the current processes under development or at the commercial stage in the pharmaceutical industry are run in batch mode. One reason for this is familiarity – process chemists are more familiar with batch processing and the large investment made over years in the existing batch process infrastructure at pharmaceutical plants. However, it is becoming increasingly evident that processes on flow have many advantages over batch mode, including improved safety when dealing with unstable reagents, smaller investments in equipment, lower solvent consumption, and efficient heat removal from exothermic reactions. Pfizer, as well as other pharmaceutical companies and academic institutions, is investing heavily in this technology as a way to manufacture drugs “on-demand” to reduce cost and improve carbon footprint.

  • Catalysis using non-precious metals: Catalysis is one of the 12 Principles of Green Chemistry and is frequently used in the synthesis of drug candidates. Unfortunately, most of the metals currently used in catalysis are precious metals, such as palladium, iridium, rhodium, platinum and ruthenium. Besides cost, a concern related to the use of these metals is their toxicity, which requires extensive purification protocol to bring levels down to acceptable values with the concomitant increase in waste, as well as their long-term supply due to their scarcity in the Earth’s crust.

    Pfizer, as part of an alliance with other pharmaceutical companies, has embarked in an ambitious program to replace those precious metals with more sustainable alternatives, such as iron, nickel and copper. These three metals are abundant, inexpensive, and display lower toxicity than precious metal catalysts, which contribute to turning catalysis into an even more attractive technology for the synthesis of drug candidates.

    Pfizer colleagues have discussed this topic during their presentations at “WOW” by showing examples from literature and comparing advantages and drawbacks for the use of these metals. Though there is still a long way to go in replacing precious metals altogether with greener alternatives, progress is being made almost daily in both academia and industry, and theses presentations intend to inform the audience about the rewards of employing iron, nickel and copper in catalytic processes and the long-term risks of not further investing now in those technologies.

 

Passion for green chemistry continues to be the driver for so many Pfizer colleagues around the world to support these types of activities – passion that has continued growing across all these years since the program’s creation.

 

 

“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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