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By Evan Riley, Communication Associate, ACS Green Chemistry Institute

 

Dan Bailey of Takeda Pharmaceuticals wins Peter Dunn Award.The recipient of this year’s Peter J. Dunn Award for Green Chemistry & Engineering Impact in the Pharmaceutical Industry is Dan Bailey of Takeda Pharmaceuticals. Bailey is based at Takeda’s R&D facility in Cambridge, Mass.

 

Established in 2016 by the ACS GCI Pharmaceutical Roundtable, the Peter J. Dunn Award recognizes excellence in the research, development and execution of green chemistry that demonstrates improvements in environmental, safety and efficiency over current technologies in the pharmaceutical industry and its allied industrial partners. The award was established in honor of Peter J. Dunn of Pfizer.

 

Bailey’s technology, titled “Beyond Organic Solvents: Synthesis of a 5-HT Receptor Agonist in Water”, uses Takeda’s pre-existing TAK-954 process as a test case to demonstrate the feasibility of implementing reactions in water. The technology simultaneously comprises all three focus areas of the award, 1) greener more sustainable synthetic routes and their associated processes to Active Pharmaceutical Ingredients (API) or intermediates, 2) reaction conditions, and 3) chemical or manufacturing process technologies as applied at meaningful scale. Bailey’s technology achieves this by developing greener reaction conditions while reducing a six-step synthesis (all reactions and isolations from water) to four.

 

Bailey developed a potential alternative to Takeda’s TAK-954 six-step current manufacturing sequence to be run almost entirely in water. Doing this replaces five separate organic solvents and simultaneously implements five direct isolations from aqueous media. Key transformations carried out in aqueous media include a benzimidazole cyclization, amidation, reductive amination, and a selective oxidation of an aliphatic alcohol. Because the reductive amination and aliphatic alcohol oxidation using the new surfactant technology were not previously described in the literature, new methodologies were invented specifically for this application. In addition to shortening the synthetic route by two steps and removing the vast majority of organic solvents from the process, Bailey and his team were able to reduce the overall PMI (Process Mass Intensity) from 350 to 111. The team noticed that shifting the reaction and isolation media from organic solvents to water had additional benefits. These include reducing the portion of the PMI attributable to solvents from 223 to 19, and surprisingly, reducing the portion of the PMI attributable to water from 106 to 76.

 

Along with receiving the Peter J. Dunn Award for Green Chemistry & Engineering Impact in the Pharmaceutical Industry, Dan Bailey will be presenting his technology at the 2020 Green Chemistry & Engineering Conference. Nominations for the 2021 award will open in the fall. To find out more, visit: https://www.acsgcipr.org/educating-leaders/#awards

By Jenny MacKellar, Program Manager, ACS Green Chemistry Institute

 

Supporting the next generation of green chemists is a strategic priority for the ACS Green Chemistry Institute (GCI). Luckily, the chemistry community is full of accomplished chemists who share a passion for scientific research and understand the value of supporting young researchers in their efforts to advance the best science. To this end, ACS GCI recently launched the Heh-Won Chang PhD Fellowship in Green Chemistry to support graduate students conducting innovative and high-quality green chemistry research. Recipients of this $5,000 award are invited to present their research at ACS GCI’s annual Green Chemistry & Engineering Conference.

 

The award’s namesake, Dr. Heh-Won Chang, was a celebrated chemist who dedicated his life to composites research. Dr. Chang earned a B.S. in chemistry at Yonsei University in Seoul, South Korea in 1961 before moving to the United States to study physical chemistry at Kansas State University where he received his M.S. in 1969 and Ph.D. in 1971. Dr. Chang’s research career included investigating carbon-carbon composites for aircraft brakes at Bendix Research Laboratories in Southfield, Michigan; researching the physical properties of polymers and continuous fiber composites at Bendix Advanced Technology Center in Columbia, Maryland; and managing the Allied-Signal’s Spectra composite business. Dr. Chang is credited with numerous papers in publications including the Journal of the American Chemical Society and the Journal of Chemical Physics. Dr. Heh-Won Chang passed away in 1994, but his memory lives on in this green chemistry fellowship established by his wife, Cecilia P. Chang in 2019.

 

2020 Winners of the Heh-Won Chang, PhD Fellowship in Green Chemistry

 

Nakisha

Nakisha Mark is a doctoral candidate in the department of chemistry at the University of the West Indies in Trinidad. Her work focuses on using greener catalysts to improve the conversion of biomass into renewable fuels. Mark is exploring the conversion of furfural, which is readily available in agricultural waste, into biofuels using nanocatalysts comprised of earth-abundant metals. Mark hopes her work will improve the sustainability of agricultural practices, particularly in the Caribbean region, by closing the loop on agricultural waste and improving the production of renewable fuels. She will present her work at the annual Green Chemistry & Engineering Conference in the “Earth Abundant Metal Catalysis” technical session.

 

 

heatherHeather LeClerc is a second-year doctoral candidate at Worcester Polytechnic Institute in Worcester, Massachusetts. Her research explores the use of a novel technology—hydrothermal liquefaction—to produce bio-crude from municipal food waste. This unique approach valorizes a waste stream while producing a more sustainable fuel source, thus addressing two unique sustainability challenges. LeClerc’s work aims to elucidate the underlying mechanisms of this process in hopes of developing more sustainable, bio-based products. Heather will present her work at the annual Green Chemistry & Engineering Conference in the “International Opportunities for the Production of Chemicals/Fuels from Waste” technical session.

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