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Using the TRI to Assess Application of Green Chemistry
Practices by the Pharmaceutical Industry in Achieving Sustainability
Stephen C. DeVito, Ph.D., R.Ph.
U.S. Environmental Protection Agency
Washington, DC
October, 2012
04/13/23 1U.S. Environmental Protection Agency
Sustainable Development: An Ongoing Priority
“Meeting the needs of the present generation without compromising the ability of future generations to meet their own needs.”
( From: C.G. Brundtland. “Our Common Future”. The World Commission on Environmental Development, Oxford Univ. Press, Oxford, 1987.)
04/13/23 2U.S. Environmental Protection Agency
National Academy of Sciences
• 4.1. Key Recommendation: “EPA should develop a “sustainability toolbox” that includes a suite of tools for use in the Sustainability Assessment and Management approach.”
04/13/23 3
Sept. 2011: Report on EPA and Sustainability
Green Chemistry • That sub-discipline in chemistry that strives to develop
environmentally friendly chemical products through synthesis pathways that neither use or generate hazardous chemicals or wastes;
• Evolved in EPA/OPPT’s Industrial Chemistry Branch in the early 1990s following passage of the Pollution Prevention Act (PPA) of 1990;
• The practice of Green Chemistry is a primary means of
achieving sustainable development.
04/13/23 4U.S. Environmental Protection Agency
Example: Commercial Synthesis of Acetophenone
5
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
Time-Honored Synthesis of Acetophenone( a TRI chemical):
Phenethyl alcohol
Example: Commercial Synthesis of Acetophenone
6
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
Time-Honored Synthesis of Acetophenone( a TRI chemical):
Phenethyl alcohol
This synthesis:
Example: Commercial Synthesis of Acetophenone
7
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
Time-Honored Synthesis of Acetophenone( a TRI chemical):
Phenethyl alcohol
This synthesis: - requires the use of two TRI chemicals (one of which is a known human carcinogen);
Example: Commercial Synthesis of Acetophenone
8
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
Time-Honored Synthesis of Acetophenone( a TRI chemical):
Phenethyl alcohol
This synthesis: - requires the use of two TRI chemicals (one of which is a known human carcinogen);
- generates a TRI chemical (also a known human carcinogen) as a waste and in large quantity;
Example: Commercial Synthesis of Acetophenone
9
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
Time-Honored Synthesis of Acetophenone( a TRI chemical):
Phenethyl alcohol
This synthesis: - requires the use of two TRI chemicals (one of which is a known human carcinogen);
- generates a TRI chemical (also a known human carcinogen) as a waste and in large quantity;
- is only 42 % efficient.
Example: Commercial Synthesis of Acetophenone
10
OH
3 + 2 CrO3
+ 3 H2SO4 O
3 + Cr2(SO4)3+ 6 H2O
Acetophenone
overall synthesis efficiency only 42 %
Time-Honored Synthesis of Acetophenone( a TRI chemical):
"Green Chemistry" Synthesis of Acetophenone:
OH
+ 0.5 O2
O
+
Acetophenone
catalystH2O
Phenethyl alcohol
Phenethyl alcohol
overall synthesis efficiency = 87 % !!
The Practice of Green Chemistry has Become Widespread in Some Industry Sectors
• Particularly in the pharmaceutical manufacturing sector;• Examples of drugs made from “green” syntheses:
– Sildenafil citrate (Viagra®) – Sitagliptin phosphate (Januvia®)
• Merck & Company received EPA’s Presidential Green Chemistry Challenge Award
– Pregabalin (Lyrica®)
• See the Green Chemistry Institute’s Pharmaceutical Roundtable website for more information.
04/13/23 11
12U.S. Environmental Protection Agency
The greener synthesis of Viagra® alone uses considerably less solvent (both in quantity and specific solvent)
13
14
Release Reductions are Sector-Wide:
Decline in releases is seen amongst the top ten pharmaceutical companies as well as the rest of the industry
04/13/23 15
Preliminary Conclusions & Next Steps
04/13/23 16
The results of our analyses indicate that the implementation of green chemistry by the pharmaceutical industry is reflected in the TRI data.
The results more broadly suggest a potential for the use of TRI data as a practical tool to track environmental progress (or lack thereof) within all manufacturing sectors.
We are currently identifying those TRI chemicals for which the pharmaceutical industry reports fewer quantities.
Acknowledgements
04/13/23 17
Abt AssociatesDana Lazarus Cheryl KeenanBecca Fink
George Washington University (Dept. of Chemistry)Dr. Adelina Voutchkova-KostalCatherine Munro