Marv Lang, Don Showalter

1
Green Chemistry
Teacher Enhancement Workshop
Kamehameha High School, Oahu, Hawaii

• Presented by
• Marv Lang, Don Showalter Gary Shulfer
• University of Wisconsin-Stevens Point, USA
• Presentation constructed by Angela Burmeister
• University of Wisconsin Stevens Point, USA

2
What is Green Chemistry?

• Green chemistry is the use of chemistry for
  pollution prevention.
• Pollution prevention is the use of materials,
  processes, or practices that reduce or eliminate
  the creation of pollutants or wastes at the
  source. It includes practices that reduce the
  use of hazardous and nonhazardous materials,
  energy, water, or other resources as well as
  those that protect natural resources through
  efficient use. -U.S. EPA
• The design of chemical products and processes
  that are more environmentally benign.
• Encompasses all aspects and types of processes
  that reduce negative impacts to human health and
  the environment.
• Focuses on processes and products that reduce or
  eliminate the use and generation of hazardous
  substances.
• Became a formal focus of the U.S. EPA in 1991
  with the formation of their Green Chemistry
  Program.
• Promotes research, development and implementation
  of inventive chemical technologies that
  accomplish pollution prevention in both a
  scientifically-sound and cost-effective manner.

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The Twelve Principles

• Prevention - It is better to prevent waste than
  to treat or clean it up after its been created.
• Atom Economy - Synthetic methods should be
  designed to maximize the incorporation of all the
  materials that are used in the process.
• Less Hazardous Chemical Synthesis - Synthetic
  methods should be designed to use and generate
  substances that possess little or no toxicity to
  human health and the environment wherever
  possible.
• Designing Safer Chemicals - Chemical products
  should be designed to effect their desired
  function while minimizing their toxicity.
• Safer Solvents and Auxiliaries - The use of
  solvents, separation agents and other auxiliary
  substances should be made unnecessary wherever
  possible and innocuous when used.
• Design for Energy Efficiency - Energy
  requirements should be minimized, synthetic
  methods should be conducted at ambient
  temperature and pressure.

• 7. Use of Renewable Feedstocks - A raw material
  or feedstock should be renewable rather than
  depleting whenever technically and economically
  practicable.
• 8. Reduce Derivatives - Unnecessary
  derivatization should be minimized or avoided
  because such steps require additional reagents
  and can generate waste.
• 9. Catalysis - Catalytic reagents are superior to
  stoichiometric reagents.
• 10. Design for Degradation - Chemical products
  should be designed so that at the end of their
  function they break down into innocuous
  degradation products that do not persist in the
  environment.
• 11. Real-time Analysis for Pollution Prevention -
  Analytical methodologies need to be further
  developed to allow for real-time, in-process
  monitoring and control prior to the formation of
  hazardous substances.
• 12. Inherently Safer Chemistry for Accident
  Prevention - Substances and their form used in a
  chemical process should be chosen to minimize the
  potential for chemical accidents, including
  releases, explosions and fires.

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Environmental Chemistry versus Green Chemistry

• Environmental chemistry is the study of sources,
  reactions, transport and fate of chemical
  entities in the air, water, and soil environments
  as well as their effects on human health and the
  environment.
• Focuses on the environmental management of
  chemicals.
• Concerned not only with the chemical pollutants
  in the environment but also with the behavior of
  natural chemicals in natural systems.
• When chemical use results in environmental
  contamination, it is necessary to set standards
  for acceptable concentrations in water, air, soil
  and biota.
• Has focused on the effects of what man has put
  into the environment and how to deal with and
  remediate contamination sites.
• Dilution is the solution to pollution
• In contrast, green chemistry focuses on how to
  change what human activity puts into the
  environment in order to eliminate or reduce
  effects and prevent contamination sites.
• An milligram of prevention is worth a kilogram
  of cure.

5
Green Synthesis of Ibuprofen

• The Boots Company PLC developed and patented the
  six step brown synthesis of ibuprofen in the
  1960s.
• The synthesis process results in millions of
  pounds of unwanted, unutilized, and unrecycled
  waste chemical byproducts that have to be treated
  or disposed of each year.
• The percentage atom economy of the brown
  synthesis of ibuprofen is 40 ?60 (by weight) of
  all reagent atoms are incorporated into unwanted
  byproduct or waste.

• The BHC Company developed and patented a greener,
  three step synthesis of ibuprofen in 1991.
• Their goal was to develop and put into practice a
  more efficient and environmentally sensitive
  method of synthesizing ibuprofen to market.
• The green synthesis provides for a far greater
  atom economy at 77 (99 if the acetic acid
  recovered from the first step is considered).
• This method prevents the formation of millions of
  pounds of waste and chemical byproduct as well as
  saves millions of pounds of reactant materials.
• The BHC Company won a Presidential Green
  Chemistry Challenge Award in 1997 for their
  development of this synthesis.

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Green Synthesis of Ibuprofen continued

• There are also other environmental advantages to
  the green synthesis.
• The brown synthesis requires auxiliary reagents
  in stoichiometric amounts. In contrast, the
  green synthesis is catalytic.
• The green synthesis uses reagents which are
  recovered and reused repeatedly (e.g. HF, Raney
  nickel, and Pd).
• The green synthesis offers greater throughput
  which allows larger quantities to be produced in
  less time resulting in less capital expenditure
  and significant economic benefits.

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Benefits to Industry

• Economic Benefits of Pollution Prevention
• 1) Save money in materials
• a) Waste is reduced
• b) More product is produced
• 2) Improve product quality
• 3) Conserve energy and water
• 4) Save money in regulatory and compliance
  costs
• a) No liability for waste produced
• -3M saved 750 million in waste disposal costs
  by 1995 after implementing their Pollution
  Prevention Pays (3P) program in 1975.
• Pollution Prevention can also help a business
• 1) Improve its bottom line
• 2) Make compliance with environmental
  regulations easier
• 3) Demonstrate a proactive commitment to the
  environment

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Green Chemistry atThe Dow Chemical Company

• Believe in the triple bottom line-meeting social,
  economic, and environmental objectives.
• Committed to reducing emissions by improving
  energy efficiency, developing less
  energy-intensive manufacturing processes, and
  producing climate-friendly products.
• Recent efforts and achievements in green
  chemistry at Dow
• Spinosad- Recipient of the 1999 Presidential
  Green Chemistry Challenge Award
• Active ingredient in Tracer Naturalyte insect
  control targeting chewing worm pests
• Derived through the fermentation of a naturally
  occurring organism
• Helps preserve the local environment while
  helping to make farms more productive, generate
  higher yields while still cost-effective to the
  farmer
• Not harmful to beneficial insects, mammals or
  fish and breaks down quickly into organic matter
  after three or four hours of sunlight exposure

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Dow Chemical Co. continued

• Sentricon Termite Colony Elimination System-
  Recipient of the 2000 PGCC Award
• Uses a very small amount of active ingredient and
  less intrusive than traditional methods
• Uses a targeted approach leading to high
  technical performance, environmental
  compatibility, and reduced human risk
• Protects about 500,000 structures across the
  country, including the Statue of Liberty, the
  White House, and Independence Hall, as well as
  structures in Australia, France, Spain and Japan

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Green Chemistry atKodak

• Recently set a series of 5-year environmental
  goals for worldwide operations to be achieved by
  January 1, 2004.
• Address 3 strategic initiatives
• Greater reductions in emissions of 30 priority
  chemicals, methylene chloride, and carbon dioxide
• Preservation of natural resources including
  reduction in the production of manufacturing
  waste, energy, water usage, and virtual
  elimination of heavy metals from Kodak products
  (e.g. Cd, Hg, Pb, Cr (IV))
• Strengthening of the companys environmental
  management

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Kodak continued

• Pollution Prevention and Waste Minimization
• Leader in recycling and reuse of its materials
• Captures and reuses manufacturing solvents and
  silver
• Recycles scrap, PET plastic and paper
• Silver recovery
• Ion exchange technology to recover wastewater
  silver
• T-Grain emulsions use less film and fewer
  chemicals
• EPA 33/50 Program
• EPA set goals of 33 reduction by 1992 and 50
  reduction by 1995
• Kodak participated and reduced emissions of the
  17 targeted chemicals by 71 by the end of 1994

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Green Chemistry andEducation

• The ACS Division of Education and International
  Activities, in partnership with the EPA Office of
  Pollution Prevention and Toxics (OPPT), is
  currently developing educational materials to
  start incorporating green chemistry into the
  general chemistry classroom.
• Teachers and professors should begin
  incorporating green goals into their courses to
  provide students with knowledge and skills to
  practice green chemistry without compromising the
  integrity of the chemical knowledge.
• Available resources
• Annotated Bibliography on Green Chemistry-
  Reference tool for use in chemistry curriculum
  available as a searchable data base to the ACS
  Education Web page at http//center.acs.org/appli
  cations/greenchem
• Real-World Cases in Green Chemistry- Contains ten
  projects that have won or been nominated for the
  PGCC Award designed for a variety of
  undergraduate courses resource of specific
  examples of redesigning chemical products and
  processes.
• Chemistry in Context and ChemCom- ACS courses for
  undergraduate and high school students,
  respectively, include new green chemistry
  materials and concepts.
• Journal of Chemical Education- Several articles
  on green chemistry and incorporating it into
  teaching have been published.

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Education continued

• Resources in development
• Green chemistry labs, demonstrations, teaching
  modules for high school teachers, publication of
  readings, green chemistry video resource for high
  school teachers, short courses, workshops,
  meetings and symposia.
• Also, undergraduate courses in green chemistry
  are being developed by various universities such
  as Carnegie Mellon University, the University of
  Delaware and the University of Scranton.
• The biggest challenge of green chemistry is to
  get people to adopt it. We would like to see it
  incorporated into every course from high school
  onwards. A. Matlack, Green Chemistry, February
  1999

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Resources

• Amato, Ivan. The Slow Birth of Green Chemistry.
  Science,Vol. 259, 12 March 1993, 1538-1541.
• Anastas, P.T. Warner, J.C. Green Chemistry
  Theory and Practice Oxford University Press
  New York, 1998.
• Cann, Michael C. Bringing State of the Art,
  Applied, Novel, Green Chemistry to the Classroom
  by Employing the Presidential Green Chemistry
  Challenge Awards. J. Chem. Ed. 1999, 76 (12),
  1639-1641.
• Cann, M.C. Connelly, M.E. Real World Cases in
  Green Chemistry, American Chemical Society
  Washington, DC, 2000.
• Collins, T.J. Introducing Green Chemistry in
  Teaching and Research. J. Chem. Ed. 1995, 72
  (11), 965-966.
• Connell, Des W. Basic Concepts of Environmental
  Chemistry CRC Press LLC-Lewis Publishers New
  York, 1997.
• Dow Chemical Company Web sites. (accessed Mar
  2001) www.dow.com/dow_news/corporate/co9_6_28.h
  tml www.dow.com/dow_news/prodbus/20000627a_pb.ht
  ml www.dow.com/dow_news/prodbus/20000627b_pb.
  html www.dow.com/dow_news/speeches/spe_lauzon
  _may.html

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Resources continued

• Freeman, Harry F. Industrial Pollution
  Prevention Handbook McGraw-Hill, Inc., 1995.
• Frost, John. Green Chemistry at Work Products
  Can be Made From Glucose Instead of Benzene.
  U.S. Environmental Protection Agency Web site.
  (accessed April 2001) www.epa.gov/docs/epajrnal/f
  all94/09.txt.html
• Kodak Web sites. (accessed Mar 2001)
  www.kodak/com/US/en/corp/environment/commitme
  nt/goals.shtml www.kodak/com/US/en/corp/environ
  ment/operations/prevention/index.shtml
  www.kodak/com/US/en/corp/environment/operations/v
  oluntary/design.shtml www.kodak/com/US/en/corp/e
  nvironment/operations/voluntary/epa.shtml
• Matlack, A. Teaching Green Chemistry. Green
  Chemistry 1999, 1 (1), G19-G20.
• Schulz, William. ACS green Chemistry Initiatives
  Get Boost from EPA Grant. Chemical and
  Engineering News, August 17, 1998, 47, 59.
• U.S. Environmental Protection Agency Web site.
  (accessed Jan 2001) www.epa.gov/greenchemistry.
  htm
• Again, a special thanks to Angie Burmeister for
  constructing this presentation!