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Pollution Prevention: A Paradigm Addressed Through GREEN CHEMISTRY Michael Cann, Chemistry Department http://academic.scranton.edu/faculty/CANNM1/ – PowerPoint PPT presentation

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Title: Pollution Prevention: A Paradigm Addressed Through GREEN


1
Pollution Prevention A Paradigm Addressed
Through GREEN CHEMISTRY
  • Michael Cann, Chemistry Department
  • http//academic.scranton.edu/faculty/CANNM1/
  • greenchemistry.html

2
Better Things for Better Living Through
Chemistry DuPont
  • Ibuprophen
  • Lipitor
  • Celebrex
  • Vioxx
  • Rogaine
  • Prozac
  • Viagra
  • Prilosec
  • Nylon
  • Dacron
  • PET
  • Polystyrene
  • Acrylics
  • Teflon
  • Rayon
  • Polyaniline
  • DNA
  • Recombinant
  • Technology
  • PCR

3
ENVIRONMENTAL DISASTERS
  • DDT
  • CFCs
  • Cuyahoga River
  • Love Canal

4
ENVIRONMENTAL DISASTERS
  • Became rallying points for environmental laws
  • Cuyahoga River- 1972 Clean Water Act
  • Love Canal- 1980 Comprehensive Environmental
    Response, Compensation Liability Act, better
    known as Superfund. Emergency Planning
    Community Right-to-Know Act, requires that
    industries
  • report toxic releases.

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6
Toxic Release Inventory
  • In 2000 7.1 billion pounds of hazardous chemicals
    were released to the air water and soil.
  • Only includes 650 of the 75,000 chemicals in use
    in US commerce today
  • Thresholds of 25,000 pounds (manufacture) and
    10,000 pounds (use)

7
Risk Due to a Hazardous Substance
Riskf(Hazard, Exposure) environmental laws
attempt to control exposure
  • Controlling Exposure end of the
  • pipe solution
  • Command and control laws

8
Command and Control Cost to Industry
  • Industries in the US spend over 100 billion/year
    on waste treatment, control, and disposal.
  • 1996 Dupont spent 1 billion for environmental
    compliance (research budget 1 billion chemical
    sales of 18 billion)

9
THE POLLUTION PREVENTION ACT OF 1990
  • Riskf(HAZARD, Exposure)
  • Eliminate the hazard, no need to worry about the
    exposure!

10
Chemists Must Place a Major Focus on the
Environmental Consequences of Chemical Products
and the Processes by which these Products are
Made. We must consider our chemical
ecological footprint.
11
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
  • resource use (maximize efficiency)
  • utilize renewable resources

12
The Twelve Principles of GREEN CHEMISTRY
(Anastas and Warner 1998)
  • 1. It is better to prevent waste than to treat or
    clean up waste after it is formed.
  •  
  • 2. Synthetic methods should be designed to
    maximize the incorporation of all materials used
    in the process into the final product.
  •  
  • 3. Wherever practicable, synthetic methodologies
    should be designed to use and generate substances
    that possess little or no toxicity to human
    health and the environment.
  •  
  • 4. Chemical products should be designed to
    preserve efficacy of function while reducing
    toxicity.
  •  
  • 5. The use of auxiliary substances (e.g.
    solvents, separation agents, etc.) should be made
    unnecessary whenever possible and, innocuous when
    used.
  •  
  • 6. Energy requirements should recognized for
    their environmental and economic impacts and
    should be minimized. Synthetic methods should be
    conducted at ambient temperature and pressure.
  •  

13
The Twelve Principles of GREEN CHEMISTRY (Anastas
and Warner 1998)
  • 7.A raw material feedstock should be renewable
    rather than depleting whenever technically and
    economically practical.
  •  
  • 8. Unnecessary derivatization (blocking group,
    protection/deprotection, temporary modification
    of physical/chemical processes) should be avoided
    whenever possible.
  •  
  • 9. Catalytic reagents (as selective as possible)
    are superior to stoichiometric reagents.
  •  
  • 10. Chemical products should be designed so that
    at the end of their function they do not persist
    in the environment and break down into innocuous
    degradation products.
  •  
  • 11. 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. Substances and the form of a substance used
    in a chemical process should chosen so as to
    minimize the potential for chemical accidents,
    including releases, explosions, and fires.
  •     

14
GREEN CHEMISTRY
  • Pollution Prevention Act 1990
  • GC Began in 1991 at EPA, Paul Anastas
  • 1996 Presidential Green Chemistry Challenge
    Awards
  • 1997 Green Chemistry and Engineering Conference
  • 1999 Journal Green Chemistry
  • Chemical Engineering News
  • 2001 Journal of Chemical Education

15
Examples of Green Chemistry
Presidential Green Chemistry Challenge Award
Winners For more informational on Presidential
Green Chemistry Challenge Award Winners
http//www.epa.gov/greenchemistry/presgcc.html
  • New syntheses of Ibuprofen and Zoloft.
  • Integrated circuit production.
  • Removing Arsenic and Chromate from pressure
    treated wood.
  • Many new pesticides.
  • New oxidants for bleaching paper and disinfecting
    water.
  • Getting the lead out of automobile paints.
  • Recyclable carpeting.
  • Replacing VOCs and chlorinated solvents.
  • Biodegradable polymers from renewable resources.

16
ATOM ECONOMYBarry Trost, Stanford
UniversityBecause 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.

17
ATOM ECONOMY
  • Atom Economy Table
  • Atom Economy (FW of atoms utilized/FW of all
    reactants) X 100 (137/275) X 100 50

18
GREEN CHEMISTRYThe BHC Company
  • The Synthesis of Ibuprofen (analgesic,
    anti-inflammatory)
  • Advil, Motrin, Medipren
  • 28-35 million pounds of ibuprofen are produced
    each year (37-46 million pounds of waste)

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Environmental Advantages of BHC Synthesis of
Ibuprofen
  • Less waste
  • greater atom economy
  • catalytic versus stoichiometric reagents
  • recycling, reuse, recovery of byproducts and
    reagents (acetic acid gt99 HF gt99.9)
  • greater throughput (three steps versus five
    steps) and overall yield (virtually quantitative)
  • Fewer auxiliary substances (solvents separation
    agents)

22
Economic Advantages of BHC Synthesis of Ibuprofen
  • Greater throughput and overall yield
  • (three steps versus five steps)
  • Greater atom economy (uses less feedstocks)
  • Fewer auxiliary substances (solvents separation
    agents)
  • Less waste (lower disposal costs)

23
Other improved syntheses
  • that are winners of Presidential Green Chemistry
    Awards include the pesticide Roundup (Rohm
    Haas), the antiviral agent Cytovene (Roche
    Colorado), and the active ingredient in the
    antidepressant Zoloft (Pfizer).

24
Confirm, Mach 2 and Intrepid Selective Insect
Control
  • Rohm and Haas Company

25
DDT
Neurotransmitter and receptor ion channel
26
ORGANOPHOSPHOROUS AND CARBAMATE INSECTICIDES
ACETYLCHOLINESTERASE INHIBITORS
  • Less persistent than organochlorine insecticides
    no bioconcentration
  • More toxic to mammals

Carbamate
X S, O R CH3, CH2CH3 Organophosphate
27
Organophosphates
Hydrolysis of Acetylcholine
28
GREEN CHEMISTRY Confirm, Mach 2 and Intrepid
  • Selective toxicity achieved by targeting the
    unique physiology of insect growth
  • The growth of certain insects is accompanied by
    the periodic shedding of their outer cuticle
    layers, a process called molting
  • Molting is initiated by an increase in the levels
    of the steroid hormone 20-hydroxyecdysone (20E)
  • A decline of 20E concentrations
  • to basal levels ends molting
  • Confirm, Mach 2 and Intrepid
  • mimic 20E

29
GREEN CHEMISTRY Confirm, Mach 2 and Intrepid
  • Confirm, Mach 2 and Intrepid mimic 20E but the
    concentration of active ingredient does not
    decline insect never sheds its cuticle and thus
    never resume feeding
  • Tebufenozide kills caterpillars while
  • halofenozide kills beetle larvae,
  • cutworms, and webworms
  • No harm to beneficial insects
  • Acute toxicity to
  • higher organisms
  • is very low

30
GREEN CHEMISTRY
  • Dry Cleaning
  • Initially gasoline and kerosene were used.
  • Chlorinated solvents are now used, such as perc.
  • Infusing green chemistry into general chemistry
  • Supercritical/liquid carbon dioxide (CO2)
  • (also used for cleaning metal surfaces,
    integrated circuits,
  • micro-electromechanical devices, flat panel
    displays)

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  • 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.

33
Surfactants for H2O(soaps and detergents)
34
CO2 Surfactant Joe DeSimone, UNC, NCSU, NSF
Science and Technology Center for
Environmentally Responsible Solvents and
Processes, PGCC Award 1997
35
CO2 Surfactant
36
  • http//www.hangersdrycleaners.com/

37
Environmental/Economic Advantages of Liquid CO2
  • Using CO2 eliminates hazardous waste generation
    of perc.
  • CO2 does not pose the environmental and human
    health risks associated with perc (used by 34,000
    dry cleaners in US).
  • Using CO2 reduces environmental regulatory
    burdens for Hangers operators.
  • Uses waste CO2 from other processes.

38
Triple Bottom Line
  • GREEN CHEMISTRYOffers the potential for
    Environmental, Economic and Social benefits
  • John Tucker, of Pfizer Inc., said the green in
    green chemistry is also the color of money
    during a discussion of Pfizers new greener
    synthesis of sertraline.

39
Green Chemistry Endeavors at Scranton
  • Real-World Cases in Green Chemistry.
  • Web based Green Chemistry Teaching Modules
    (Spanish, Portuguese).
  • Greening existing chemistry textbooks.
  • Environmental Chemistry, Colin Baird, W.H.
    Freeman
  • Chemistry Foundations and Applications,
    Macmillan
  • The business side of green chemistry.
  • Survey of PGCC applicant
  • Infusion into business courses
  • Bringing green chemistry to the high school and
    secondary school level.
  • Integrating sustainability throughout our
  • campus.

40
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 Tracy Williamson
  • White House Office of Science and Technology
    Policy Paul Anastas
  • Green Chemistry Institute Mary Kirchhoff
  • Universidad de Las Palmas de Gran Canaria,
  • Maria de la Concepcion, Sebastian Perez

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