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					Pollution Prevention: A Model
 Addressed Through GREEN
        CHEMISTRY



        Michael Cann, Chemistry Department
   http://academic.scranton.edu/faculty/CANNM1/
                greenchemistry.html
      “Better Things for Better
     Living Through Chemistry”
                         DuPont

•   Ibuprophen   •   Nylon
•   Lipitor      •   Dacron        •DNA
                                   •Recombinant
•   Celebrex     •   PET
                                   Technology
•   Vioxx        •   Polystyrene   •PCR
•   Rogaine      •   Acrylics
•   Prozac       •   Teflon
•   Viagra       •   Rayon
•   Prilosec     •   Composites
    ENVIRONMENTAL
       DISASTERS
•   DDT
•   CFCs
•   Cuyahoga River
•   Love Canal
               Growth i n Environmental Regul ati on
                                                                                                                                      EPACT
                                                                                                                                      FFCA
                                                                                                                                      CERFA
                                                                                                                                      CRAA
                                                                                                                                      PPA
                                                                                           AMFA                                       PPVA
                                                                                          ARPAA                                       IEREA
                                                                                            AJA                           AQ          ANTPA
            120                                                                         ASBCAA                            A           GLCPA
                                                                                     ESAA-AECA                                        ABA
                                                                                          FFRAA                                       CZARA
                                                                                         FEAPRA                                       WRDA
            110                                                                              IRA                                      EDP
                                                                                         NWPAA                          NAWCA         OPA
                                                                                 CODRA /NM SPAA                                       RECA
                                                                                          FCRPA                                       CAAA
                                                                                         MM PAA                                       GCRA
            100                                                                                                                       GLFWRA
                                                                                              APA        RCRAA         WQA            HMTUSA
                                                                                            SWDA          WLDI                        NEEA
                                                                                          CERCLA
             90                                                                             CZMIA                NWPA
                                                                                         COWLDA                                       SDWAA
                                                                                           FWLCA                                      SARA
                                                                                         M PRSAA
             80                                                                                                                       BLRA
                                                                                             CAAA             ARPA                    ERDDAA
                                                                                              CWA                         M PRSAA     EAWA
                                                                                           SM CRA                                     NOPPA
                                                                                           SWRCA                                      PTSA
             70                                                                            SDWAA                                      UM TRCA
                                                                                                                                      ESAA
                                                                                            BLBA                                      QGA
                                                                                          FWPCA       HMTA                            NCPA
Number of




             60                                                                           M PRSA
                                                                                           CZMA ESA                                   TSCA
                                                                                             NCA TAPA                                 FLPMA
                                                                                          FEPCA                                       RCRA
            Laws




             50                                                                            PWSA                                       NFMA
                                                                                           MM PA                       FRRRPA         CZMAA
                                                                                                                       SOWA
                                                                                                                       DPA            NEPA
             40                                                                       AQA                                             EQIA
                                                                                      FOIA           FCMHSA                           CAA
                                                                                                                                      EPA
                                                                                      WRPA                                            EEA
                                                                                      AFCA                                            OSHA
             30                                                                                                                       FAWRAA
                                                                                       FHSA                                           NPAA
                                                                                     NFM UA                          WSRA
                                                                 TA                                                  EA
                                                               FWCA      AEPA   FIFRA PAA              NH PA         RCFHSA
             20                                                 BPA
                                                                                                    WLDA
                                                 WA                                              FWCAA
                                             NBRA      NPS      M BCA         FAWRA
                                                 IA                                            FWA
             10                       RHA   AA                             NLRA          AEA
                     YA                                                    WPA

                   0
                   1870 1880   1890     1900    1910    1920      1930   1940     1950        1960     1970     1980     1990       2000
     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)
  Risk Due to a Hazardous
        Substance

 Risk=f(Hazard, Exposure)
Controlling Exposure = “end of the pipe
 solution”
“Command and control” laws
“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)
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.
    THE POLLUTION
 PREVENTION ACT OF 1990

Risk=f(HAZARD, Exposure)

Control the hazard, no need to worry
 about the exposure!
  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).
  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 and Engineering News
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.
  GREEN CHEMISTRY
            The 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)
                                      SYNTHESIS OF IBUPROFEN
                                                        GREEN VS. BROWN
                                                                             H
       THE BHC COMPANY                             CH3                          THE BOOTS COMPANY
       PROCESS                                                                  PROCESS
                                                                                        O
                                          H3C
                                  O
                                                                1                H 3C            Step 1
         Step 1    H 3C                                                                  O
                                  O                                              H 3C
                                      2                                AlCl 3                2                O
                   H 3C
                                                                                        O
                                                  HF
                                  O


                                              O                                 CH3                                 CH3
                                                                                                              3
         CH3                                       CH3                 H3C
                                                                                        Cl       CH   COOC2H5
                                                                                                      4             Step 2
                                                                                            H
 H3C                                  3                                                 NaOC2H5
                                                                                         5    H3C                   O
                   H2     4
Step 2                                                                                                                  H
                                              OH                                CH3

                                                                                                                    CO 2C2H5
         CH3                                       CH2
                                                        +
                                                                       H3C                                6


 H3C                                      5                                                  +                      Step 3
                                                                                        H3O                   CH3
                                                                                             7
                   CO                                                                                                     O
                              6                                                 CH3
Step 3             Pd

                                                                       H3C                                8
                                               CH3
                                                                                                                    Step 4
                                                                                        NH2OH 9               CH3
          CH3                                          COOH
                                                                                                                          N
                                                                                CH3                                             OH
  H3C
       Ibuprofen              13                                                                              10
                                                                       H3C


                                                                                                              CH3
                                                                                                                    Step 5
                                                                       12
                                                                    2H2O
                                                                                CH3                                 C       N
                                                       Step 6
                                                                                                          11
                                                                       H3C
  Advantages of the BHC
  Synthesis of Ibuprofen
• Less waste
• More economical
  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)
Surfactants for H2O
(soaps and detergents)
CO2 Surfactant:        Joe DeSimone, UNC, NCSU, NSF Science
and Technology Center for Environmentally Responsible Solvents
and Processes, PGCC Award 1997
CO2 Surfactant
• http://www.hangersdrycleaners.com/
    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.
     NatureWorks Polylactic Acid
 A Biodegradable Polymer Produced from
          Renewable Resources

       O


H       OH
               Cargill Dow
HO      H

H       OH
               Minnetonka, MN
H       OH   2002 PGCC Award
       OH
                Polymers
                    •   PET
•   Nylon
                    •   Polycarbonate
•   Dacron
                    •   Polyacrylamides
•   Kevlar
                    •   Polypropylene
•   Rayon
                    •   Polystyrene
•   Teflon
                    •   Polyethylene
•   Styrofoam
                    •   Polyaniline
                 Polymers
• The polymer industry produces over 60 billion
  pounds of polymers per year
• The production of polymers consumes about 130
  billion pounds of chemical feedstocks per year
• 2.7% of all crude oil is used for chemical
  feedstocks
• 4 billion pounds of PET produced in
  1998, only 745 million pounds were
  recycled, 81%, landfilled or
  incinerated.
NatureWorks PLA
Green Chemistry
  polymers from corn
 Environmental Advantages of
     Nature Works PLA
• Made from annually renewable resources
  (corn, sugar beets, eventually waste
  biomass)
• Consumes 20-50% less fossil fuel resources
  than petroleum based polymers
• Uses natural fermentation to produce lactic
  acid
 Environmental Advantages of
     Nature Works PLA
• PLA can be recycled (converted back to
  monomer via hydrolysis, then
  repolymerized to produce virgin polymer)
  i.e. closed lop recycling
• PLA can be composted (biodegradable),
  complete degradation occurs in a few weeks
  under normal composting conditions
     Products Made From PLA
•   Fibers for clothing, pillows, diapers
•   Cups
•   Rigid food containers, food wrappers/bags
•   Bags for refuse
•   Furnishings for home and office (carpet tile,
    upholstery, awnings, industrial
    wall panels)