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The ACS Green Chemistry Institute® is pleased to announce the opening of the 2018 Green Chemistry Challenge Awards. The U.S. EPA supports the continuation of the awards program for 2018 under the sponsorship of the ACS GCI. To ensure continuity, the awards categories and guidelines are remaining the same, only the timing of the awards cycle is changing, and the ACS GCI will be managing the awards program and making final decisions about award winners.

 

As in past years, an independent scientific panel convened by ACS GCI will be making recommendations for the award winners, with the final decisions for each award category chosen by members of the ACS GCI Advisory Board.

 

Estimated Timeline:

  • Submissions accepted from April 30, 2018 through July 2, 2018
  • Award winners notified no later than August 31, 2018
  • Awards ceremony to be held in Washington, D.C. on October 2018

 

The award guidelines and nomination package will be posted on the ACS GCI website by April 30, 2018, and these will follow the same guidelines as in previous years. Interested parties are encouraged to begin the process for submission as soon as possible.

 

If you have any questions, please email gci@acs.org.

Contributed by Paul D. Thornton, Development Scientist, GreenCentre Canada, and Laura M. Reyes, Career Development Leader, Chemical Institute of Canada

 

We have organized a full-day session at this year’s GC&E conference called "Accelerating Development of Sustainable Products and Processes Through Start-Ups and SMEs," which will bring together entrepreneurs from various sectors and stages of company growth to share their stories, focusing on successes and turning points, expected and unexpected challenges, and lessons learned along the way. We will also hear about existing resources that can be creatively leveraged for maximum impact toward a growing company’s commercialization goals. While there is no easy roadmap for a green chemistry start-up to follow, there are valuable lessons to be learned from these shared experiences, and it is our hope that this session will help enable entrepreneurship in green chemistry and the resulting market adoption of innovative products and processes.

 

This session, which will take place all day on Wednesday, June 20, will greatly benefit anyone who is involved in, or interested in, start-ups and small-to-medium enterprises (SMEs) based in green chemistry. All conference delegates are highly encouraged to attend and join us in learning different perspectives of what is needed to bring a green product or process to market.

 

We will feature presentations from nine entrepreneurs and company founders, from fields as diverse as waste recycling, to safer consumer products, to naturally sourced ingredients. The talks will include two keynote speakers. In the morning, Lauren Zarama, the CEO of InKemia Green Chemicals, will discuss her company’s approach to innovating and commercializing greener and safer chemistry solutions. In the afternoon, Richard Blackburn, the co-founder and director of Keracol and a professor at the University of Leeds, will discuss commercializing natural products for use in the cosmetics industry and how he balances academia and entrepreneurship. The other companies featured are: framergy, Grow Bioplastics, Newreka Green Synth Technologies, RAPID Manufacturing USA Institute, remooble, and Sironix Renewables.

 

Following the start-up presentations, we will shift focus towards available resources, including the Green Chemistry & Commerce Council’s Green & Bio-Based Chemistry Startup Network, and considerations to keep in mind when turning a technology into a business. A series of short talks will cover the importance of market focus (by Diatomix), the most critical intellectual property tips (by Finnegan LLP), and the due diligence process behind investing in new ventures (by Chemical Angel Network). An interactive discussion will close off the day, highlighting the technical and business needs of entrepreneurs and small businesses in green chemistry, and what resources are available to address those gaps. We look forward to continuing these lively conversations shortly after our session at the GC&E’s Green Chemistry on Tap social!

The ACS Green Chemistry Institute® receives input from a variety of stakeholders and last week the GCI Advisory Board met in Washington, DC. Chaired by ACS Past President and former Chair of the Board Bill Carroll, the Advisory Board includes Concepción Jiménez-González, GlaxoSmithKline; Lauren Heine, Northwest Green Chemistry; Audrey Moores, McGill University; Michael Kirschner, Design Chain Associates, LLC; and Tony Noce, Tetra Tech and Chair of the ACS Committee on Environmental Improvement.

 

Advisory Board members provided guidance to GCI staff on a number of topics, including the U.N. Sustainable Development Goals, the International Year of the Periodic Table, and the Green Chemistry Challenge Awards.  The Advisory Board discussed the recent GAO report on "Chemical Innovation: Technologies to Make Processes and Products More Sustainable" and received updates on federal policy related to green chemistry, collaborations between the green chemistry and safety communities, and progress on the environmental genome project.

 

The Advisory Board also received an update and provided feedback on the 2018 Green Chemistry & Engineering Conference, the premier venue for sharing expertise across the green chemistry and engineering community. We are thrilled to be returning to Portland, Oregon on June 18-20 for the 22nd Annual Conference with a theme of “Product Innovation Using Greener Chemistries”. In addition to 30 technical symposia, this year’s conference will feature several interactive sessions along with a product showcase demonstrating green chemistry and engineering applications in the marketplace. The early-bird deadline of April 30 is fast approaching and I encourage you to register at www.gcande.org to take advantage of the best conference rate.

 

At last month’s ACS National Meeting in New Orleans, GCI recognized the ACS Student Chapters that are sharing their green chemistry expertise on their campuses and within their local communities. A total of 56 Student Chapters were honored for their green chemistry activities during the Student Chapters Awards Ceremony on Sunday, March 18. Approximately 1,000 students and their faculty advisors celebrated the accomplishments of all of the Student Chapters during this high-energy ceremony.

 

The ACS National Meeting also provided a venue to reflect upon advances in green chemistry since the principles of green chemistry were introduced by Paul Anastas and John Warner 20 years ago. Speakers in the “State-of-the-Art:  Two Decades Advancing the 12 Principles of Green Chemistry” session highlighted products and processes that address each of the principles, as well as opportunities to further promote the integration of green chemistry across the chemistry enterprise.

 

As we approach Earth Day, it is important to continue sharing our expertise with colleagues, students, family, and friends. Chemistry in service to humanity is a powerful message that reflects our commitment to protecting human health and the environment through the implementation of green and sustainable chemistry and engineering.

 

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Organized by Jennifer Y. Tanir, M. Barclay Satterfield, Robert Giraud, George Cobb, and David Constable (members of ACS Committee on Environmental Improvement)

 

We cordially invite conference attendees to participate in an interactive, 1-day workshop, "Charting the Course to Sustainable Chemistry in the Supply Chain," on Wednesday, June 20. The goal of the workshop is to evaluate successes of integrating green/sustainable chemistry into the supply chain in the formulated personal care and household products sector and distill the learnings into a plan for widespread adoption.

 

One of the barriers to the ubiquitous implementation of sustainable chemistry is strong integration and acceptance throughout the supply chain. Despite many individual single-product or single-company successes, or a few advances in limited sectors’ supply chains, there is still a need for widespread agreement on sustainability goals and cooperation throughout the supply chain.

 

The interactive workshop will be divided in to three sessions: (1) Lessons Learned; (2) Gaps, Challenges, and Needs; and (3) Facilitated Discussion and Roadmapping, with the goal of developing a plan (and ultimately a publication) to improve incorporation of sustainable chemistry in the supply chain for formulated products. The first two sessions are panel discussions with subsequent breakout discussions for the audience to contribute their ideas to key questions. In the final session, the facilitated discussion and roadmapping aims to articulate the vision for success and identify the 4 or 5 major milestones or key recommendations to move the sector from the current status to goal status.

 

We are holding this workshop at the 2018 GC&E Conference in order to bring together diverse thinking: technical experts in the formulated personal care and household products with other sectors, learnings from other sectors that can be applied, new ways of thinking, and students who can develop future solutions. Conference attendees are encouraged to participate as an audience, in the breakout discussions, and in developing the plan forward through the roadmapping discussion.

The symposium "Chemistry in Water – Following Nature’s Lead" honors the winners of the 2018 Peter J. Dunn award by the ACS GCI Pharmaceutical Roundtable: Prof. Sachin Handa, University of Louisville, and Prof. Bruce Lipshutz, University of California, Santa Barbara. The Symposium features the latest developments in new synthetic chemistry from both academic and industrial labs that document not only that waste creation can be minimized, but that by going green, “faster, better, cheaper” processes oftentimes can be anticipated.

 

Prof. Sachin Handa’s award lecture "Non-Traditional Approaches to Chemical Catalysis to Sustainably Achieve Selective Reaction Pathways" will focus on issues with reproducibility, purity and selectivity arising at the multi-gram scale. In addressing these issues, Prof. Handa’s group has sought to develop catalysts, reagents and reaction media which are cheap, sustainable, easily recyclable, safer to use and yet also markedly improve reaction outcomes in terms of activity, selectivity and scalability.

 

Prof. Bruce Lipshutz’s award lecture "Synthetic Organic Chemistry in Water, Environmentally Responsible and Sustainable" will focus on the recent (unpublished) development of new palladacycles that are matched to both a ligand and their use in micellar catalysis, thereby enabling Suzuki-Miyaura (SM) cross-couplings at 300 ppm levels of Pd. A new ligand platform will also be discussed that can be prepared in only two steps, and that also can be applied to ppm level Pd-catalyzed SM reactions in water under mild conditions.

 

Dr. Wilfried Braje, Senior Principle Scientist at AbbVie, will give his presentation "Organic Chemistry in Water: Applications in the Pharmaceutical Industry" that will disclose applications of micellar catalysis for the most important reaction types performed in the pharmaceutical industry (e.g., transition-metal-catalyzed reactions such as Buchwald-Hartwig aminations, Suzuki, and Negishi couplings). In addition, a new additive will be disclosed for the first time. This additive enables chemical reactions to proceed in water with unprecedented short reaction times.

 

Dr. Fabrice Gallou, Principle Fellow at Novartis, will present a talk entitled "Alternative Solvents: From a Compliance-Driven Activity to a Trigger for Innovation" focusing on the application of the surfactant technology developed by professors Lipshutz and Handa. The team at Novartis has identified a variety of straightforward and highly advantageous transformations and their applications on-scale. Implementation of the technology typically resulted in significant benefits across their entire portfolio, not just from an environmental standpoint but also from an economic and productivity perspective (e.g., reduction in organic solvent consumption, water use and cycle time, milder reaction conditions, and improved yields and selectivities, which all contribute to improved process performance and lower manufacturing costs).

 

The Symposium will be held at the Green Chemistry & Engineering Conference in Portland on Monday, June 18, 2018, from 9:45 a.m. to 12:25 p.m.

This Monday afternoon session will highlight industry innovations based on green chemistry and engineering principles, focusing on the development and design process. Case studies will be presented to illustrate how companies in different sectors have successfully implemented green chemistry and engineering principles into their processes. These examples will describe the design and development process, the challenges faced, and how these barriers were overcome. Additionally, this session will discuss the important collaborations along the value chain and with the academic community.

 

From the session, attendees should be able to understand at a high level how industry develops products and processes, and the many factors that contribute to the launch and commercialization of new greener technologies.  Presenters will be from industry and academia in order to share the valuable insights of a diverse group on the challenges and opportunities in bringing sustainable chemistries and processes to market.

 

Symposium organizer:

Ettigounder (Samy) Ponnusamy, Ph.D.

Fellow & Global Manager, Green Chemistry

MilliporeSigma

 

Presentations include:

 

  • Finding nature-inspired alternatives to PFASs in durable water repellency (DWR): an academic/industry approach. T. McKeag
  • "Greener solutions" and "PFCs of environmental concern". B.J. Henry
  • Development of an eco-friendly biotransformation protocol for valorization of food industry waste for commercial application in consumer products. N. Mexia, M. Benohoud, C.M. Rayner, R.S. Blackburn
  • Sustainable dyeing of cotton: Graft-polymerization of AOETMAC to achieve ultra-deep black shades without salt or alkali. M. Abed, S. Salim, S. Mandal, A. El Shafei
  • Assessment of modernized chromatographic methods for a greener tomorrow from a global perspective. M.B. Hicks, L. Lehmann, W.P. Farrell, C.M. Aurigemma, J. Xu, R. Dermenjian
  • Green chemistry innovation in chemiluminescent conjugate manufacturing processes. J. Grote
  • Green chemistry impacts on environmental media. S.D. Gaona, A. Lew
  • Sustainability at an enterprise level: Focusing greening of the value chain. H. Plugge
  • Single-step co-synthesis of methanol, dimethyl ether and dimethyl carbonate from biomass-derived syngas. P. Sripada, A. Parihar, S. Bhattacharya
  • Cl2-free production of ethylene dichloride and propylene oxide. J. Hauck, M. Leclerc
  • Recycling metal swarf by extraction of cutting oils with supercritical CO2. R. Schlake, A. Kaziunas

Effective and inherently safer chemical products and processes are the obvious choice over their hazardous counterparts. The market appears to agree, with one forecasting analysis predicting that alternative chemical products, i.e., those made with inherently safer and more sustainable ingredients, will experience a 19.4% compound annual growth rate (CAGR) between 2016 and 2026 (BCC Research).

 

While many chemists are inspired to use their skills to improve health, safety and environmental impacts, a gap remains between innovation and implementation. Work on basic and/or applied research challenges is very different from bringing products to the marketplace. And products don’t simply have to be safer; they also have to perform as well as or better than existing products, in terms of both cost and functionality. There are also societal, political, and educational hurdles to overcome.

 

In our session, "Real-World Sustainability Challenges: Incentives and Barriers to the Use of Green Chemistry in Products," our speakers and panelists will explore this divide as well as best practices for successfully bridging the gap. We’re thrilled to have four outstanding session chairs: Dr. Lauren Heine, Northwest Green Chemistry (NGC)’s Executive Director; Dr. Amelia Nestler, NGC’s Project Manager; Anthony (Tony) Noce, Vice President, EHS Management Systems at Tetra Tech; and Ray Garant, Director of Public Policy at the American Chemical Society.

 

The diverse drivers for the adoption of green chemistry in products are not necessarily in alignment. Our session speakers will explore how creative initiatives supportive of safer products, like environmentally preferable procurement policies and start-up support,  often contrast with uncompromising obstacles such as lack of funding, limited market awareness or outdated standards and regulations.

 

Our line-up of expert speakers will cover these, and many more, drivers and barriers in depth and from first-hand practical experience:

 

To support scientists in fulfilling the promise of green chemistry to provide practical, sustainable solutions in the marketplace, they will discuss:

  • How to shepherd a great idea into a real and successful product
  • Resources that are available to designers at different stages in development
  • Common pitfalls and best practices for overcoming them
  • Sources of inspiration for solving real-world sustainability problems
  • Systems models and metrics for success

 

Join the conversation with product developers, regulators, investors, and procurement professionals to advance your innovative ideas and bring safe, sustainable products to the market. We look forward to hearing about your green chemistry product development experiences at the 22nd Annual Green Chemistry and Engineering Conference!

The Center for Green Chemistry & Green Engineering at Yale is collaborating with the United Nations Industrial Development Organization (UNIDO) on a three-year project to increase the general global awareness and capacities on deployable green chemistry in developing countries and countries with economies in transition.

 

This project, funded by the Global Environment Facility (GEF), is part of the Yale-UNIDO Global Green Chemistry Initiative and was developed in response to the increasing variety and complexity of chemicals and the need to make the products safer and their manufacturing processes less polluting.

 

The Initiative consists of series of workshops in six countries where green chemistry experts deliver a one-day green chemistry awareness workshop, followed by a five-day training workshop developed for participants from industry, academia, non-profits and government. All workshops provide hands-on tools and materials to assist with the design of products and processes that advance global sustainability. In addition to the workshops—taking place in Brazil, Serbia, Colombia, Sri Lanka, Egypt and South Africa—the Center is also developing a university curriculum for students to teach green chemistry to undergraduates as early as their freshman year. This work is done in collaboration with Beyond Benign and will include lecture materials, laboratory exercises, and videos that are developed by students around the world.

 

“We are thrilled to be leading this project and to be working with the local and international green chemistry communities to develop the most effective way to disseminate green chemistry materials to countries around the world. So far the feedback we received has been fantastic and the workshops have been very well received by participating countries. We are eager to do more.” said Karolina Mellor, Ph.D., one of the Yale-UNIDO project managers.

 

“Thanks to UNIDO and GEF generosity, and the wonderful support from students, faculty and our local partners, we are able to do work that has the potential to impact countries’ sustainable development,” added Dr. Mellor.

 

As the project develops, the Yale-UNIDO Global Green Chemistry Initiative plans to engage the green chemistry community to develop a comprehensive compendium of green chemistry and green engineering technologies that include the broad array of innovations that are commercially available today. The document will provide a comprehensive collection of green technologies within developed and transitioning countries.

 

The Yale-UNIDO Initiative will be highlighted by Professor Paul Anastas, Ph.D., at the 2018 Green Chemistry & Engineering Conference in Portland, Oregon at the session “Providing guidance for a wide distribution and implementation of green chemistry to developing countries and economies in transition,” where student videos will be shown and our strategy of community engagement will be outlined.

 

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Awareness Raising Workshop in Belgrade, Serbia

Contributed by Jennifer MacKellar, Program Manager, ACS Green Chemistry Institute

 

Over the years, there have been many efforts to provide green chemistry resources and support for chemistry educators. We are pleased to announce another outstanding resource developed through a collaborative effort of chemistry educators: a green chemistry supplement to the ACS Guidelines for Bachelor’s Degree Programs. The development of the Green Chemistry in the Curriculum supplement was led by the ACS Committee on Environmental Improvement with the support of many educators in the green chemistry community. This is just one more example of the incredible passion and commitment the green chemistry community demonstrates for enabling the adoption of green chemistry principles and practices in chemistry education.

 

The premise of the supplement is one that many of us in the green chemistry community already stand behind wholeheartedly, that in order for chemists to play a central role in addressing the grand challenges of sustainability, the integration of green chemistry principles and systems thinking is needed throughout the traditional chemistry subdisciplines. The Green Chemistry in the Curriculum supplement provides the context for why green and sustainable chemistry is critical for the next generation of chemists and provides some guidance for approaching chemistry education from a context-rich or systems thinking perspective.  Continuing on, the supplement articulates some illustrative examples of green chemistry for each of the foundational chemistry courses: General Chemistry, Organic, Inorganic, Analytical, Physical and Biochemistry. While this is not an exhaustive list by any means, it is intended to demonstrate how green chemistry concepts are relevant to all areas of chemistry and could, ideally, be scaffolded across the curriculum.

 

The ACS Guidelines for Bachelor Degree programs provide standards that define excellent and rigorous programs for undergraduate chemistry education. There are over 680 approved chemistry programs. The ACS Committee on Professional Training is in charge of this approval procedure. In addition to the guidelines, the Committee publishes supplements that provide advice to institutions that wish to develop specific aspects of their chemistry program.

 

The green chemistry supplement was approved by the Committee on Professional Training during the ACS National Meeting in New Orleans. When this news emerged at the meeting, the initial reception among educators was enthusiastic. We hope that you will also value this resource and share it with colleagues.

 

Successfully integrating green chemistry throughout the chemistry curriculum is a long-term strategic goal of ACS GCI. We will continue to support efforts to this end through our work on a Green Chemistry Education Roadmap, as well as by collaborating with key stakeholders such as Beyond Benign and the IUPAC Systems Thinking in Chemistry Education. Together we can make a difference!

 

We are currently in the process of plans to expand on the information in the supplement to give even more resources and guidance. We’d love to hear from you. How are you bringing green chemistry into your courses? What resources would be helpful?

 

Finally, I would like to give a quick shout-out to the amazing line-up of green chemistry enthusiasts who made this supplement possible. Without your wisdom, experience, and perseverance, we would not be where we are today.

 

Thank you!

 

Tony Noce  ·  Kate Aubrecht  ·  Marie Bourgeois  ·  Ed Brush  ·  Jane Wissinger  ·  Cathy Middlecamp  ·  Julie Haack  ·  Alan Elzerman  ·  Jim Hutchison  ·  David Constable  ·  Dave Finster  ·  Irv Levy  ·  Amy Cannon  ·  Tom Holme

Contributed by Karolina Mellor, Ph.D., Program Manager, Center for Green Chemistry and Green Engineering at Yale University

 

Yale Center for Green Chemistry and Green Engineering recently developed an educational computer game which introduces the concepts of sustainability, chemistry and rational design to undergraduate students using a virtual environment. Safer Chemical Design Game intended for incorporation into any chemistry course for majors or non-majors that teaches sustainability and/or the Principles of Green Chemistry. The game is free of charge and encourages students to think like professional chemical designers and to develop a chemical product with respect to function and improved human and environmental health.

 

Student’s skills in communication and critical thinking can be increased substantially by integrating practical and hands-on experiences into their curriculum. In addition, the use of practical experiences, as well as the bridging of disciplines through projects, can positively influence interest in science and knowledge retention. Integrating these findings into existing lesson plans promotes the development of more integrative courses and allows students to make more connections between the scientific topics of study and the problems that they face in daily life.

 

The Safer Chemical Design Game designed to introduce students to safer chemical design concepts and is focused on the manipulation of physicochemical parameters in order to minimize the undesired biological and environmental interactions of a hypothetical commercial chemical. The game scenarios presented to the student (player) model the decision-making process used by professionals to design a new chemical. Critically, the computer game simulates the real-world constraints that may affect chemical product development. The challenge is for the students to design a safer and more sustainable chemical product using multi-criteria decision analysis. Players can select different combinations of molecular parameters that lead to qualitative outputs related to toxicity, biodegradability, biotransformation and overall performance. In doing so, the player must navigate potential trade-offs that are consequences of their choices. Feedback after each task allows players to redesign the chemical product to improve the design.

 

Game Objectives

  • Produce a scientifically accurate game that provides students an opportunity to solve problems as though they are practicing professionals.
  • Engage and entertain students through a captivating storyline and the relevance to real-world issues (i.e. sustainability).
  • Teach sustainable design principals and life cycle thinking.
  • Educate students about toxicity, biodegradability, and overall performance of a hypothetic chemical product.
  • Incorporate systems thinking and interdisciplinary content at the nexus of chemistry, toxicology, and environmental science.

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The Safer Chemical Design Game is live and can be accessed at http://greenchemistry.yale.edu/education/undergraduate-graduate → Safer Chemical Design Game.

Interested in learning more about green chemistry at New Orleans? You can find symposia on green chemistry and sustainability by searching the online program or mobile app, or by browsing Technical Sessions, click on Filter by Themes, check and apply green chemistry or sustainability.

 

Highlights

 

This year marks the 20th anniversary of “Green Chemistry: Theory and Practice” by Paul Anastas and John Warner. This work identified twelve principles for practicing chemistry in a way that reduces or eliminates hazardous substances and waste. Its publication promoted greater awareness that chemists play a key role in creating a more sustainable future, and this message inspired, and continues to inspire, academic research and industrial application. We invite you to celebrate this anniversary in a full-day session in honor of Anastas and Warner entitled, “State of the Art: Two Decades of the 12 Principles of Green Chemistry.” Monday, March 19, a.m. and p.m. in Blaine Kern E, New Orleans Marriott

 

The ACS GCI Pharmaceutical Roundtable (GCIPR) is offering several opportunities to learn and engage at this Spring National Meeting:

  • Join a GCIPR workshop entitled “Essential Green Chemistry Tools and Techniques for Pharmaceutical Scientists,” that will equip practicing chemists and graduate students with practical tools, methods and metrics. The free workshop is Sunday, March 18, 1:30 -4:30 p.m. in Gallier B, Sheraton New Orleans. Space is limited. Register for the workshop in the meeting registration process, or email gci@acs.org. There is a small deposit required to secure your seat, refunded upon attendance of the workshop.

  • Join the GCIPR for a full day Wednesday to discuss continuous flow, green solvents, biocatalysis, novel high-throughput enabling technologies and more in an I&EC session on “Innovative Green Processing Technology & Chemistry” on Wednesday, March 21, 2018, 8-11:45 a.m. and 1-4:05 p.m. in Louisiana II, Loews New Orleans Hotel.

  • As the market for biopharmaceuticals grow, so does the environmental footprint of their manufacture. The GCIPR Biopharma team has developed a Process Mass Intensity (PMI) tool for biologics and benchmarked environmental impact across companies. Learn more about this study in BIOT 80, “Mining data to improve environmental impact of biomanufacturing,” as well as comparative analysis of different types of manufacturing processes for a monoclonal antibody using PMI at Merck (BIOT 554), and GSK’s analysis of using the Carbon Footprint Calculator as an additional assessment tool at GSK (BIOT 456).

 

Want to learn how to integrated green chemistry into your ACS Student Chapter? Don’t miss the CHED session, “Green Chemistry Student Chapters: Stories of Success” on Sunday, March 18, 1:30 p.m. at Blaine Kern B, New Orleans Marriott Convention Center.

 

Join us to congratulate the 56 ACS Student Chapters who are receiving an award for their green chemistry activities at the Student Awards Ceremony on Sunday night.

 

Learn how you can integrating green chemistry into the curriculum, classroom, lab and student research activities. This CHED day-long session, “Green Chemistry Theory and Practice: Food, Energy, & Water Sustainability,” covers a range of successful examples and initiatives of interest to the community. Drop by Tuesday, March 20, 2018 from 8:30-11:40 a.m. and 1:30-4:45 p.m. in the Blaine Kern B, New Orleans Marriott Convention Center.

 

The fun never ends! Wednesday evening starts the ENVR session “Green Chemistry & the Environment” full of theoretical and experimental green chemistry research in biocatalysis, chemical engineering, toxicology and more. The session is Wednesday, March 21, 6 p.m. and Thursday, March 22 at 8:30 a.m. in Hall D, Ernst N. Morial Convention Center.

 

Don’t miss these special lectures:

  • ORGN: ACS Award for Affordable Green Chemistry: Symposium in honor of B. Frank Gupton & D. Tyler McQuade on Monday, March 19, 1 p.m., La Nouvelle Orleans Ballroom C, Ernest N. Morial Convention Center.

  • There are three 2018 ACS Sustainable Chemistry & Engineering Journal Lectureship Award symposia:
    • I&EC: Symposium in honor of Fengqi You – Monday, March 19, 1 p.m. in Feliciana East, Loews New Orleans Hotel
    • CELL: Symposium in honor of Rafael Luque Monday, March 19, 8 a.m. in St. Landry, Loews New Orleans Hotel
    • CELL: Symposium in honor of Ning Yan – Tuesday, March 20, 8 a.m. in St. Tammany, Loews New Orleans Hotel

 

Last but not least, be sure to visit ACS GCI in the Expo, Booth #646

  • Come by and spin our prize wheel to win green chemistry swag and prizes!
  • Learn about the Design Principles of green chemistry and see how you can apply them to our studies, research and work.
  • Stop by the ACS store and pick up a green chemistry t-shirt, pint glass, endangered elements poster and more!
  • Follow @ACSGCI for live updates. Win prizes! Have fun! Learn more about green chemistry!

Rafael Luque, Professor, Departamento de Quimica Organica, Universidad de Cordoba, Spain

 

Mechanochemistry deals with chemical transformations induced by mechanical means such as compression, shear or friction. In mechanochemical processes, the energy required for the activation of chemical reactions is usually provided by mechanical force as similar to thermochemistry, photochemistry or electrochemistry where energy is provided by heat, light or electrical potential, respectively.

 

Importantly, the solvent often plays a key role in energy dispersion, dissolution/solvation and transportation of chemicals in conventional chemical synthesis. Mass and energy transport may also be hampered in solventless reactions. The efficient mixing process under ball milling or grinding can offer an effective way out of this problem, enabling the reactions between solids/powders or solidified reagents in solvent-free conditions.

 

Solventless, “dry milling” mechanochemical approaches, highly advantageous for certain applications, can also be replaced by “liquid-assisted grinding” (LAG) as bridging alternative to minimize the use of solvents in mechanochemical syntheses. In contrast to “dry milling”, LAG may offer advantages such as greater time efficiency, enhancing molecular mobility and can result in the discovery of new or improved reactivity and (nano)materials.

 

Mechanochemical processes have a number of relevant advantages as compared to conventional syntheses including 1) an inherently “greener” approach to conduct chemical/materials syntheses (solvent-free or solvent-limited); 2) improved energy efficiency and solvent use (up to 1000-fold reduction/improvement); 3) swiftness and remarkably faster than solution synthesis (allowing a rapid screening of synthesis conditions for materials and/or chemical reactions); 4) wider choice of starting materials and possibilities (e.g. cheaper and more environmentally friendly reactants); 5) high yielding and facilitating/avoiding purification/isolation steps.

 

In view of these relevant advantages, the potential of mechanochemistry is significant, not only in the design of advanced and new (nano)materials for applications in multiple fields (adsorption, catalysis, energy storage, sensing, etc.) but also in the promotion of chemical reactions (mechanocatalysis). Some relevant examples are given in the following sections.

 

Design of advanced (nano)materials

 

Mechanochemistry has already paved the way to the design of advanced and new functional (nano)materials which includes (but not limited to) perovskites, spinels, metal-organic frameworks (MOFs), supported nanoparticles on porous materials, bionanoconjugates an electrodes/biosensors (i.e. laccase@TiO2@C) and many more. The possibilities are enormous and mechanochemistry was found to provide access to new structures, enhanced properties and improved activities in certain applications (e.g. catalysis).

 

Organic-inorganic hybrid perovskites are materials that have attracted significant attention due to their extraordinary optoelectronic properties with applications in the fields of solar energy, lighting, photodetectors, and lasers. The rational design of these hybrid materials is a key factor in the optimization of their performance in perovskite-based devices. These could be successfully synthesized using a highly efficient, simple, and reproducible solventless mechanochemical approach. Materials could be synthesized 1) in large amounts (multi-gram scale), 2) as polycrystalline powders with high purity, and 3) in a very short synthesis time (typically 10-30 mins). Three-dimensional (3D) (e.g. MAPbI3 and FAPbI3), bidimensional (2D) (e.g. Gua2PbI4) and one-dimensional (1D) perovskites (e.g. GuaPbI3) were reported, indicating also a unique flexibility of the mechanochemical step to provide access to different types of structures (Figure 1).

 

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    Figure 1: Source http://onlinelibrary.wiley.com/doi/10.1002/anie.201607397/full 

 

Mixed spinel inorganic materials (e.g. MgFe2O4 and MgAl2O4 can be also synthesized in high yields, purity and short times of syntheses (15-30 mins) under solventless mechanochemical conditions. The mechanochemical approach provides a simple and efficient alternative to conventional methods to prepare spinels which typically employ large quantities of solvents (sol-gel, hydrothermal methods) or extremely high temperatures >1200ºC (combustion methods), illustrating the potential of this methodology. In addition to the green credentials of mechanochemistry, spinel materials obtained by this method were reported to be highly crystalline, homogeneous in shape and particle size and could be again obtained in large quantities (multi-gram scale) within a short processing time.

 

Similarly, metal-organic frameworks (MOFs) comprising organic molecules linking transition metals to form a porous material network have been also synthesized using solventless mechanochemical methods, providing access to new structures (e.g. pillared MOFS from their metal oxides, new porous MOFs or quasi-MOFs, etc.). Apart from the different new structures that can be potentially designed by means of the mechanochemical approach, the green chemistry advantages of the mechanochemical methodology are also clear: a 30 min grinding with limited quantities of solvents (via LAG) at room temperature could replace a 24-48 h solvothermal synthesis (100-160ºC) using large quantities of solvents and 10,000 times more energy consuming (http://onlinelibrary.wiley.com/wol1/doi/10.1002/anie.200906583/abstract)

 

Last, but not least importantly, bio(nano)conjugates have been recently developed using mechanochemical syntheses comprising redox proteins (e.g. horse hemoglobin) and magnetic nanoparticles for various relevant applications including the synthesis of carbon-based fluorescent polymers at room temperature (see Figure 2), electrochemistry and energy storage (http://pubs.rsc.org/en/content/articlelanding/2018/nr/c8nr00512e/unauth#!divAbst ract). In some cases, the utilized magnetic (and other non-magnetic systems) can also be effectively synthesized in a ball mill under mild reaction conditions (room temperature, solid-state reactions, solvent-free, typically in minutes).

Figure2.gif

 

Figure 2: Overview of the oxidative catalyzed polymerization of phenylenediamines.
Bottom images correspond to poly-o, m and pPDA (left image) and UV-irradiated poly-o, m and pPDA (365 nm), respectively. Source: http://pubs.rsc.org/-/content/articlehtml/2018/gc/c7gc03295a 
Reproduced by permission of the Royal Society of Chemistry

 

 

Mechanocatalysis

 

In addition to the mechanochemical syntheses, the possibility to conduct chemical reactions using mechanochemistry (mechanocatalysis) also recently emerged as a promising alternative to promote a number of chemistries under mild and environmentally friendly reaction conditions. Stemming from the aforementioned advantages, oxidations, C-C coupling reactions, acid-based catalyzed processes (e.g. esterifications) and related others have been already reported to take place under mechanochemical conditions.

 

Figure3.png

Figure 3: Mechanochemical/catalytic reactions: from reactants to products. Reproduced by permission of the Royal Society of Chemistry

 

 

 

 

Interestingly, biomass conversion was also successfully accomplished using mechanocatalysis, with examples of cellulose depolymerization to sugars and lignin deconstruction to valuable aromatics. This has a significant potential for further studies and its combination with a rational understanding of catalyst/process design will undoubtedly lead to important scientific advances in biomass conversion in future years.

 

Conclusions

 

From the beginning, this contribution has been aimed to provide an overview of the relevance and inherent advantages of mechanochemistry for multiple applications (materials design, catalysis, organic syntheses, biomass deconstruction, etc.). Reported results to date clearly illustrate the present and future potential and possibilities of mechanochemistry despite the relatively poor understanding of the phenomenon as such. Further studies are needed to be able to fully understand chemical, physical and structural changes taking place in mechanochemical syntheses (in-situ methodologies) to rationally design processes and methodologies based on such fundamental understanding. These studies will in any case complement nicely the burgeoning possibilities of mechanochemistry in various fields based on its inherent green credentials.

The Advanced Bioeconomy Leadership Conference on Development & Deployment (ABLC) is next week, February 28-March 2, 2018 in Washington, DC. The ACS Green Chemistry Institute’s Biochemical Technology Leadership Roundtable launched at this event in 2016, and this year they are back to present a two-part symposium on new high performance chemical intermediates and new pathways to current platform chemicals.

 

The first part of the symposium will be on the topic of “New High-Performance Chemical Intermediates”. This symposium will highlight the opportunities and challenges of commercializing new platform chemicals.  Renewable feedstocks can be a rich source of novel molecules that can serve as alternative building blocks in the synthesis of intermediates currently relying on petrochemical supply chains.  Individual speakers and a panel discussion will address the potential benefits of such molecules as well as the technical, economic, and market challenges along the way to commercialization.  Featured speakers are Peter Kneeling, CBIRC; Darcy Prather, Kalion; Kim Raiford, Origin Materials; Stephen Croskrey, Danimer; and  David Constable, ACS GCI.

 

The second part of the symposium will be about “New Pathways to Current Platform Chemicals”. In this symposium, the production of current, high-volume platform chemicals from alternative, low-carbon feedstocks will be discussed. New conversion technologies have opened up a variety of waste resources for making chemical intermediates currently derived from petroleum. Such “drop-in” molecules have the potential to displace fossil resources in chemical manufacturing without impacting current production routes. The speakers will provide examples of new pathways, discussing both the benefits and the challenges of bringing such products to market. Featured speakers are Bryan Tracy, White Dog Labs; Laurel Harmon, LanzaTech; Terry Papoutsakis, University of Delaware; Greg Smith, Croda; and Barbara Bramble, NWF (panel moderator).

 

Find out more: http://biofuelsdigest.com/ablc/

 

 

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Contributed by Abigail Giarrosso, Research Assistant at the Toxics Use Reduction Institute

 

As a sophomore chemistry major at the University of Massachusetts, Lowell (UMass Lowell), it was my time to take the chemistry major-specific organic laboratory course, a difficult and rigorous class. At the same time, I was working as a lab assistant at the Toxics Use Reduction Institute (TURI) where I was learning about green chemistry and working on replacing the solvent methylene chloride in commercial paint strippers. As I learned more about green chemistry through my time at TURI, I became very interested in being involved in the green chemistry community. As a result, I went to the Green Chemistry and Commerce Council (GC3) conference and I joined the nonprofit Beyond Benign. I learned about green chemistry from every source except my own university. I wanted to learn formally in class about green chemistry techniques and sustainable chemistry, but no courses were offered. As I thought back to my organic laboratory experience, I realized it would be a perfect opportunity to learn about waste reduction and using safer chemicals in hands-on lessons. I knew from my experience with the green chemistry community that places such as Gordon College had completely integrated green chemistry into their organic curriculum and so I was confident that finding safer experiments was feasible. I realized that this was an opportunity for awareness of sustainability and green chemistry to be formally taught at my school, making it easier for the next student to be informed and increasing awareness for future chemists.

 

I approached Dr. Jessica Garcia, the director of the undergraduate organic labs at UMass Lowell, and asked how she would feel if I tried to substitute some of the experiments for Organic Lab II with peer-reviewed, safer experiments. She was very enthusiastic about the idea because she was trying to do the same thing. So that is how came to take on helping “green” the organic labs as my senior thesis.

 

The project started in Spring 2016 with an initially straight-forward search to find safer replacements for the more complicated reactions. I found peer-reviewed articles on the Greener Education Materials for Chemists (GEMS) website on Diels-Alder, Wittig, and Michael and Aldol addition reactions. I also proposed that the experiments be conducted in microscale instead of miniscale to reduce the amount of waste generated. The highlight of the project was when I formally introducing green chemistry in class to the sophomore chemistry majors; covering what is green chemistry, why it should be important to them, and comparing and contrasting the previous and the new experiment in terms of safety.

 

Giarrosso.jpg

 

#1: Replacing a Diels-Alder Reaction

 

The first experiment that we replaced was the Diels-Alder reaction from the textbook Gilbert and Martin, which creates the byproduct sulfur dioxide and utilizes the solvents xylenes and petroleum ether.1 The safer experiment that I found in a different textbook was atom economic, created no byproducts, and eliminated the use of harmful solvents by using water.2 Both experiments involved heating under reflux, but the green experiment refluxed for three times as long as the original experiment. The students seemed to understand the safety improvements of the experiment but complained about the experiment being boring due to the long reflux. The substitution was successful and demonstrated the green principles clearly.

 

#2: Replacing a Wittig Experiment

 

Two different Wittig reactions were chosen to replace the original Wittig experiment. The original experiment, again from the Gilbert and Martin textbook, involved a very hazardous Wittig reagent benzyltriphenylphosphonium chloride, used dichloromethane (methylene chloride!), and concentrated sodium hydroxide.3 Two greener experiments were chosen to demonstrate the concepts of stereospecificity and isomerization. Both are considered solvent-less reactions and use safer Wittig reagents, and only took about 15 minutes to complete each one.4 The only issue I had with this experiment was that it needed hexanes to triturate the product. I tried substituting hexanes with undecane (heptane was not available) and successfully removed the product, but the boiling point of undecane was too high to isolate the product with adequate purity. The students struggled to perform two experiments simultaneously and struggled with the small amount of product produced at microscale. Since the minor isomer of the reaction with benzaldehyde was not detectable with a 60 MHz NMR the experiment will be discontinued. The stereospecificity reaction with 9-anthraldehyde will be kept on the curriculum for the next year.

 

#3: Replacing a Michael and Aldol Addition

 

The replacement of the Michael and Aldol addition was not as successful as the previous two experiments. The original experiment was a good candidate for replacement because of its hazardous starting materials and it uses toluene as a solvent.5 The safer experiment was a solvent-less experiment that used safer reactants and eliminated the use of toluene. The experiment involved mixing the reactants together, which made a liquid, and grinding them with a mortar and pestle until a solid formed and then refluxing the solid to get the product. Sadly, as hard as I tried, I couldn’t get my reactants into a solid. It became a very sticky paste, but not as the solid should have looked as described in the journal article. When I refluxed the paste, it did not result in the expected product. The students had a very similar experience to mine and the lab period consisted of 20 people furiously grinding paste. It was a good demonstration of how real research sometimes fails, but it was not a successful example of green chemistry.

 

Creating a New Organic Lab Experiment for Non-Majors

 

The second semester of my senior project Dr. Garcia and I wanted to create a new reaction that could introduce green chemistry in Organic I lab to other majors such as biology and chemical engineering that do not take the Organic II lab for chemistry majors. One experiment that could be replaced was the E1 dehydration of 4-methylcyclohexanol. The issues with this experiment was that the reactant and products had minor health issues and the reaction used concentrated sulfuric and phosphoric acids. The driving force behind replacing this experiment was that the product has a strong, unpleasant odor. Our goal became to create a new E1 reaction that had a more pleasant odor and utilized reusable acid catalysts to replace the use of concentrated acids. Dr. Garcia came across the journal article “Unsaturated Hydrocarbons with Fruity and Floral Odors” whose structures could theoretically be made through an E1 dehydration and were known to have a pleasing smell.7 The simplest molecule in the paper was butylidenecyclohexane which was a possible dehydration product of 1-cyclohexyl-1-butanol or 1-n-butylcyclohexanol. We decided to see if the alcohols could be dehydrated using the standard concentrated acids, reusable K10 montmorillonite clay, and reusable amberlyst catalyst. The products were analyzed by gas chromatography, NMR spectroscopy, and IR spectroscopy.

 

It was found that all three proton sources did dehydrate both alcohols resulting in varying ratios of products since the E1 dehydration results in multiple products due to carbocation rearrangement. The concentrated acids produced two products, including butylidenecyclohexane. While the reusable catalysts had about four different products, including the desired product. Sadly, through the synthesis of standards and dehydration of the alcohols, it was found that the new reaction did not have a strong fruity and floral odor and had more of a gasoline smell. Although one of the product standards created by Wittig reaction had a wonderful fruity smell, it was never the dominant product of the dehydration. Due to the cost of the starting alcohols and the lack of improvement of the smell of the experiment, the new reaction will not be implemented in the Organic I Lab curriculum. It was found that the original dehydration of 4-methylcyclohexanol works with the reusable K10 montmorillonite clay, creating an opportunity to introduce green chemistry earlier in the undergraduate academic career. Other E1 dehydration reactions are still being investigated for a new experiment.

 

Overall, I am very proud to have brought an aspect of green chemistry to my school and I hope it will inspire other faculty members to look at their own teaching lab experiments to reduce waste and hazardous materials. Although I am graduating, Dr. Garcia is looking for other students who are interested in creating new, safer experiments for the UML teaching lab.

 

References

  1. Gilbert and Martin. Experimental Organic Chemistry: a miniscale and microscale approach, 5th edition, 261-268.
  2. Pavia, D.L.; et al. A Small Scale Approach to Organic Laboratory Techniques, 3rd edition, 400-411.
  3. Gilbert and Martin. Experimental Organic Chemistry: a miniscale and microscale approach, 5th edition, 421-426.
  4. Nguyen, K. C.; Weizman, H. Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3-(9-Anthryl)-2-Propenoic Acid Ethyl Ester. J. Chem. Educ., 2007, 84 (1), 119-121.
  5. Gilbert and Martin. Experimental Organic Chemistry: a miniscale and microscale approach, 5th edition, 625-630.
  6. Pavia, D.L.; et al. A Small Scale Approach to Organic Laboratory Techniques, 3rd edition, 324-326.
  7. Anselmi, C.; et al. Unsaturated Hydrocarbons with Fruity and Floral Odors. J. Agric. Food. Chem., 2000, 48, 1285-1289.

 

 

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Ken-picture.jpg

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

 

The green chemistry community lost a friend with the passing of Ken Seddon on January 21.  Ken's stellar science, coupled with his strong opinions and kind heart, made him unforgettable (as did those muttonchops!)

 

I first met Ken in 1999 at the Green Chemistry Gordon Research Conference in Oxford. I knew Ken by reputation but did not meet him until I was waiting for a taxi at the Oxford train station. I noticed Ken's luggage tag, and exclaimed, “You're Ken Seddon!” He acknowledged the veracity of my statement and we agreed to share a ride to campus. When the cab pulled up, the driver began loading passengers from the rear of the line.  In a classic Ken maneuver, he slammed his hands on the bonnet of the car and shouted, "The front of the queue is over here!" The taxi driver quickly realized the error of his ways.

 

Ken could be intimidating; when I told him that I was glad to be on his good side, he replied, "No one wants to be on my bad side!" He was a wonderful listener and provided me (and many others) with comfort, support, and words of wisdom during difficult times. He told me on more than one occasion that he had the soggiest shoulder in Belfast.

 

I had the gift of a five-day visit with Ken in December. Ken continued to direct his research group at the Queen's University Ionic Liquids Laboratories, write manuscripts, and prepare proposals from the nursing home in Cultra. We had lengthy conversations about the future of green chemistry; not surprisingly, Ken assigned me a few tasks to do when I returned home. We talked about books, music, and movies, and Ken introduced me to the brilliant BBC show W1A.

 

Ken will be remembered for his groundbreaking research on ionic liquids, which earned him many accolades, including the Order of the British Empire (OBE) in 2015. What I will remember most about Ken was his warmth and kindness. He was a wonderful son to his lovely Mum Muriel, and a true friend to numerous colleagues around the world.  Ken's science will live on through the work of his many collaborators, and his generosity of spirit will live on in our hearts.

 

 

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