Michael Cann, Chemistry Department - PowerPoint PPT Presentation

1 / 49
About This Presentation
Title:

Michael Cann, Chemistry Department

Description:

– PowerPoint PPT presentation

Number of Views:112
Avg rating:3.0/5.0
Slides: 50
Provided by: academ7
Category:

less

Transcript and Presenter's Notes

Title: Michael Cann, Chemistry Department


1
GREENING THE CHEMISTRY CURRICULUM
  • Michael Cann, Chemistry Department
  • http//academic.scranton.edu/faculty/CANNM1/greenc
    hemistry.html

2
Sustainability
  • "Meeting the needs of the present without
    compromising the ability of future generations to
    meet their needs."
  • (The U.N. Brundtland Commission 1987)
  • JUSTICE?

3
Sustainability?
Nature
  • Are we exceeding the carrying capacity of the
    earth? Are we using resources and creating waste
    faster that the earth can take our wastes and
    convert them back into resources?

Resources
Consumption
Waste
Humans
Resources
Consumption
Waste
4
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.
5
GREEN CHEMISTRY
  • Green Chemistry, or sustainable/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

6
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.
  •  

7
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.
  •     

8
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
  • 2000 GCI integrated into ACS
  • 2000 Journal of Chemical Education

9
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.

10
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.

11
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.

12
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

13
(No Transcript)
14
(No Transcript)
15
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

16
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)

17
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

18
GREEN CHEMISTRY MODULES FOR SPECIFIC CHEMISTRY
COURSES
  • Polymer Polyaspartic acid
  • Industrial Petretec polyester regeneration
  • Environmental Sea-nine antifoulant
  • Toxicology Confirm,
  • Mach 2, and Intrepid

19
GREEN CHEMISTRY MODULES FOR SPECIFIC CHEMISTRY
COURSES
  • Introduction to Green Chemistry
  • 17,000 hits 500 different universities
  • Module text, questions and bibliography
  • Notes to instructors
  • Power Point presentation
  • http//academic.scranton.edu/faculty/CANNM1/dreyfu
    smodules.html

20
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.

21
ATOM ECONOMY
  • Atom Economy Table
  • Atom Economy (FW of atoms utilized/FW of all
    reactants) X 100 (137/275) X 100 50

22
ATOM ECONOMY IN THE WITTIG REACTION
23
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)

24
(No Transcript)
25
(No Transcript)
26
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)

27
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)

28
GREEN CHEMISTRY
  • Major Focus Replacement of organic solvents
    -VOCs, halogenated, almost 15 billion kilograms
    produced wordwide each year
  • Solvent free
  • Solvent alternatives
  • Ionic liquids
  • Fluorous
  • Carbon dioxide

29
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

30
(No Transcript)
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
Surfactant
33
CO2 Surfactant Joe DeSimone, UNC, NCSU, NSF
Science and Technology Center for
Environmentally Responsible Solvents and
Processes, PGCC Award 1997
34
CO2 Surfactant
35
  • http//www.hangersdrycleaners.com/

36
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.

37
GREEN CHEMISTRY
  • Antifoulants (algae and seaweed
  • barnacles and diatoms)
  • Pesticides, infusing green
  • chemistry into environmental chemistry

38
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?

39
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

40
Green Chemistry Environmental Chemistry
  • Ozone hole and troposheric air pollution carbon
    dioxide as a replacement for CFCs and hydrocarbon
    blowing agents surfactants for carbon dioxide so
    that carbon dioxide can be used to replace VOCs.
  • Pesticides readily biodegradable marine
    antifoulant as replacement for tributyltin oxide
    selective pesticides as replacements for broad
    spectrum pesticides.
  • Toxic organic chemicals (e.g. dioxins)
    activators of hydrogen peroxide to replace
    chlorine bleaching agents.
  • Polluted water and sewage treatment
    biodegradable scale inhibitors and dispersing
    agents as a replacement for polyacrylate polymer.
  • Solid waste, landfills and closed loop recycling
    Petretec process for conversion of PET back into
    its monomers and reformation into virgin PET.

41
(No Transcript)
42
Environmental ChemistryBaird Cann
  • Introduction to Green Chemistry Atom economy
    synthesis of ibuprofen.
  • Ozone CO2 as a blowing agent Harpin as a
    replacement for methyl bromide fumigant.
  • Tropospheric pollutants CO2 surfactants.
  • Greenhouse gases scCO2 in photolithography.
  • Energy/petroleum biodegradable polymers from
    renewable resources.
  • Pesticides selective pesticides termite
    control/ reduced risk pesticides.

43
Environmental ChemistryBaird Cann
  • Toxic organics non-chlorine bleaching agents,
    H2O2 activators
  • Water pollution/purification enzymatic
    preparation of cotton textiles biodegradable
    chelating agents
  • Heavy metals removal of lead from automobile
    paint removal of arsenic and cadmium from
    pressure treated wood
  • Solid waste biodegradable antiscalant recylable
    carpeting

44
Green Chemistry Endeavors at Scranton
  • Greening existing chemistry textbooks.
  • Organic Chemistry, Solomons Fryhle, Wiley
  • Chemistry Foundations and Applications,
    Macmillan
  • Translation of our web-based Green Chemistry
    Modules into Spanish Portuguese.
  • The business side of green chemistry.
  • Infusion into business courses
  • Bringing green chemistry to the high school and
    secondary school level.
  • Integrating sustainability throughout our
  • campus http//matrix.scranton.edu/sustainability/
    default.shtml

45
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, Mary
    Kirchhoff, Janet Boese, Mary Ann Ryan
  • Environmental Protection Agency Tracy Williamson
  • Green Chemistry Institute Paul Anastas
  • Universidad de Las Palmas de Gran Canaria,
  • Maria de la Concepcion, Sebastian Perez
  • Universidade Federal de Pelotas (UFPel)Eder J.
    Lenardãoa Colleagues

46
(No Transcript)
47
(No Transcript)
48
(No Transcript)
49
(No Transcript)
Write a Comment
User Comments (0)
About PowerShow.com