Michael Cann, Chemistry Department

1
GREENING ACROSS THE CHEMISTRY CURRICULUM
INCLUDING WEB-BASED TEACHING MODULES

• Michael Cann, Chemistry Department
• University of Scranton
• http//academic.scranton.edu/faculty/CANNM1/greenc
  hemistry.html

2
Better Things for Better Living Through
Chemistry DuPont
3
ENVIRONMENTAL DISASTERS

• DDT
• CFCs
• Cuyahoga River
• Love Canal

4
(No Transcript)
5
Toxic Release Inventory

• In 1997 23.85 billion pounds of hazardous
  chemicals were treated, recycled, used for energy
  production , disposed of, or released.
• Only includes 600 of the 75,000 chemicals in use
  in US commerce today
• Thresholds of 25,000 pounds (manufacture) and
  10,000 pounds (u

6
Risk Due to a Hazardous Substance
Riskf(Hazard, Exposure)

• Controlling Exposure end of the pipe solution
• Command and control laws

7
Command and Control Cost to Industry

• 1992 industry spent 115 billion on waste
  treatment, control, and disposal.
• 1996 Dupont spent 1 billion for environmental
  compliance (research budget 1 billion chemical
  sales of 18 billion)

8
THE POLLUTION PREVENTION ACT OF 1990

• Riskf(HAZARD, Exposure)
• Control the hazard, no need to worry about the
  exposure!

9
It is Essential that Chemists Place a Major Focus
on the Environmental Consequences of Chemical
Products and the Processes by which these
Products are Made
10
GREEN CHEMISTRY

• Green Chemistry or environmentally benign
  chemistry is the design of chemical products and
  processes that reduce of eliminate the use and
  generation of hazardous substances
• Minimize waste, energy use and resource use
  (maximize efficiency
• utilize renewable resources).

11
GREEN CHEMISTRY

• Pollution Prevention Act 1990
• GC Began in 1991 at EPA, Paul Anastas
• 1996 Presidential Green Chemistry Challenge
  Awards
• 1996 Green Chemistry and Engineering Conference
• 1999 Journal Green Chemistry
• Chemical and Engineering News

12
GREEN CHEMISTRY

• "Green chemistry represents the pillars that hold
  up our sustainable future. It is imperative to
  teach the value of green chemistry to tomorrow's
  chemists."
• Daryle Busch, President ACS, June 26,
  2000, Color Me Green
• Chem. Eng. News 2000, 78 (28) 49-55.

13
ENVIRONMENTAL CHEMISTRY

• Poster/Oral Presentation on one of the PGCC Award
  Winning Proposals 1996
• Cann, Michael C., J. Chem. Ed. 1999, 76 (12),
  1639-1641.

14
REAL-WORLD CASES IN GREEN CHEMISTRY

• ACS/EPA Green Chemistry Educational Materials
  Development Project, 1998
• Compilation of materials on real-world green
  chemistry (based on PGCC) in a format that can be
  used for educational purposes
• Each case acts as an informational
  resource for instructors to use in
  greening their courses
• Marc Connelly
• http//www.acs.org/portal/Chemistry?PIDacsdisplay
  .html
• DOCeducation\greenchem\cases.html

15
(No Transcript)
16
(No Transcript)
17
MAINSTREAMING GREEN CHEMISTRY

• Insertion of green chemistry into mainstream
  chemistry courses
• Need faculty who teach these courses to develop
  modules on green chemistry related to topics
  already covered in their course
• Make it easy (lower Eact) for other
• faculty to do the same
• place materials on the web

18
WEB BASED GREEN CHEMISTRY MODULES FOR SPECIFIC
CHEMISTRY COURSES

• Major support-The Camille and Henry Dreyfus
  Foundation
• Additional support-ACS/EPA, University of
  Scranton
• T. Dickneider, T. Foley, D. Marx, D.
  Narsavage-Heald, J. Wasilewski
• (The Green Machine)

19
GREEN CHEMISTRY MODULES FOR SPECIFIC CHEMISTRY
COURSES

• General -Surfactants for CO2
• Organic -Atom economy
• Inorganic Activators of hydrogen peroxide for
  green oxidation
• Biochemistry Confirm, Mach 2 and Intrepid
  pesticides
• Advanced Organic Elimination of Chlorine in NAS

20
GREEN CHEMISTRY MODULES FOR SPECIFIC CHEMISTRY
COURSES

• Polymer Polyaspartic acid
• Industrial Petretec polyester regeneration
• Environmental Sea-nine antifoulant
• Toxicology Confirm,
• Mach 2, and Intrepid

21
GREEN CHEMISTRY MODULES FOR SPECIFIC CHEMISTRY
COURSES

• Introduction to Green Chemistry
• Module text, questions and bibliography
• Notes to instructors
• Power Point presentation
• http//academic.scranton.edu/faculty/CANNM1/
• dreyfusmodules.html

22
ATOM ECONOMYBecause an Atom is a Terrible Thing
to Waste

• How many of the atoms of the reactant are
  incorporated into the final product and how many
  are wasted? Infusing green chemistry into
  organic.

23
ATOM ECONOMY

• Atom Economy Table
• Atom Economy (FW of atoms utilized/FW of all
  reactants) X 100 (137/275) X 100 50

24
ATOM ECONOMY IN THE WITTIG REACTION
25
GREEN CHEMISTRY

• The Synthesis of Ibuprofen
• Advil, Motrin, Medipren
• 28-35 million pounds of ibuprofen are produced
  each year (37-46 million pounds of waste)

26
(No Transcript)
27
(No Transcript)
28
GREEN CHEMISTRY

• Dry Cleaning
• Initially gasoline and kerosene were used
• Chlorinated solvents are now used, such as perc
• Supercritical/liquid carbon
• dioxide (CO2) infusing green
• chemistry into general chemistry

29
(No Transcript)
30
Surfactant
31
Solubility of Substances in CO2

• Carbon dioxide a non polar molecule since the
  dipoles of the two bonds cancel one another.
• Carbon dioxide will dissolve smaller non polar
  molecules
• hydrocarbons having less than 20 carbon atoms
• other organic molecules such as aldehydes,
  esters, and ketones
• But it will not dissolve larger molecules such as
  oils, waxes, grease, polymers, and proteins, or
  polar molecules.

32
(No Transcript)
33
CO2 Surfactant
34

• http//www.hangersdrycleaners.com/

35
GREEN CHEMISTRY

• Antifoulants (algae and seaweed
• barnacles and diatoms)
• Pesticides, infusing green
• chemistry into environmental chemistry

36
Antifoulants

• TBTO
• Half-life of TBTO in seawater is gt 6 months
• Bioconcentration, 104
• Chronic Toxicity
• Thickness of oyster shells
• Sex changes in whelks
• Imposex in snails
• Immune system in dolphins and others?

37
Antifoulants

• DCOI (PGCC award Rohm and Haas)
• Acutely toxic to a wide range of marine organisms
  (effective anitfoulant)
• Rapid biodegradation to nontoxic products
• (½ life lt 1 hour)
• Low Bioconcnetration
• (bioconcentration 13)
• Environmental Conc. lt Acute Toxicity level
• No Chronic Toxicity
• Rapid partitioning to the sediment
• (low bioavailability)
• 
  4,5-dichloro-2-n-octyl-4-isothiazolin
  -3-one

38
Acknowledgements

• Marc Connelly
• The Green Machine
• Trudy Dickneider, Tim Foley, David Marx, Donna
  Narsavage-Heald, Joan Wasilewski
• Camille and Henry Dreyfus Foundation
• American Chemical Society
• Sylvia Ware, Janet Boese, Mary Ann Ryan
• Environmental Protection Agency
• Paul Anastas, Tracy Williamson,
• Green Chemistry Institute
• Mary Kirchhoff

39
(No Transcript)
40
(No Transcript)