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Green Chemistry a Synthetic Chemist's Perspective

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Green Chemistry a Synthetic Chemist's Perspective Green Chemistry Hermenegildo Garcia Department of Chemistry D2Q-9 96 387 7807 (ext 73441 y 78572) [email protected] www.upv.es/herme How to pass the course? • Attendance to class is mandatory •You can miss one class max. • To perform exercises and homework •Assignment 4 •Correct exercises •Present in due time •Public presentation (30 min) •Written exam 7 • Volonteers 10 Assignment List • History • Examples of novel green chemistry processes • Presidential Green Chemistry Challenge award winners • Propose practical demonstrations • Renewable feedstocks • EPA grants • Search for reviews and literature reports • Search for web pages and electronic addresses • Assistance to prepare new class material Actions aiming at Green Chemistry Goverment Academia •Laws and regulations • Courses and training •Control • Research in new processes •Funding and promotion Industry General public • Development of new processes • Information • Development of new products • Good practices • New renewables feedstocks • Support extra costs • Safe operation The ACS/EPA Cooperative Agreement • What is the EPA? • What is ACS? • EPA/ACS collaboration Propose nominations to the Presidential Green Chemistry Challenge Awards Program Highlights the concerns with current products and processes Presents a green chemistry solution Real-World Cases in Green Chemistry ACS Activities Earth Day Program Green chemistry in the curriculum (books) Green chemistry summer school National Chemistry Week Interactive Teaching Units Europe and Japan • Royal Society of Chemistry • Venice (7th Summer school in green chemistry) • Barcelona (Green Chemistry PhD course) • European Commission (Cost Actions) • York and other European Universities • Japan is developing very strong initiatives Can the Chemistry be Dirty? Atmospheric pollution • Green house effect and energy consumption • Ozone layer depletion • Photochemical smog • Smoke (NOx and SOx) Aqueous pollution • Fertilizers, pesticides, insecticides Solid pollution • Industrial waste waters • Industrial soils • Solvents • Nuclear and radiactive wastes • Deter gents and urban waste waters • Chemical residues Examples of Chemical Products of the 20th Century Thalidomide. DDT. CFCs. Endocrine disruptors. Bioaccumulating substances. Persistent/non-biodegradable materials. Why the chemistry is dirty? • Provides energy • Provides materials (plastics, paper, etc) • Provides commodities (sprays, detergents, paints, dyes) • Provides fertilizers, insecticides, pesticides • Provides drugs and pharmaceuticals • Social demand • Social com plain Growth of Legal Regulation EPACT FFCA CERFA CRAA PPA AMFA PPVA ARPAA IEREA AJA AQ ANTPA 120 AS BCAA A GLCPA ES AA-AECA ABA FFRAA CZARA FEAPRA WRDA 110 IRA EDP NWPAA NAWCA OPA CODRA/NMS PAA RECA 100 FCRPA CAAA MMPAA GCRA GLFWRA HMTUS A APA RCRAA WQA 90 S WDA WLDI NEEA CERCLA CZMIA 80 COWLDA NWPA S DWAA FWLCA S ARA MPRS AA BLRA 70 CAAA ARPA ERDDAA CWA MPRS AA EAWA S MCRA NOPPA S WRCA PTS A 60 S DWAA UMTRCA ES AA BLB A QGA FWPCA HMTA NCPA f 50 MPRS A o CZMA ES A TS CA r TAPA e 40 NCA FLPMA b FEPCA RCRA s PWS A NFMA m w MMPA FRRRPA CZMAA u a S OWA N L 30 DPA NEPA AQA EQIA FOIA FCMHS A CAA 20 EPA WRPA EEA AFCA OS HA 10 FAWRAA FHS A NPAA NFMUA WS RA TA EA 0 FWCA AEPA FIFRA PAA NHPA RCFHS A B PA WLDA WA FWCAA NBRA NPS MB CA FAWRA IA FWA RHA AA NLRA AEA YA WPA 1870 1880 1890 1900 1910 1920 19 30 1940 1950 1960 1970 1980 1990 2000 What is Green Chemistry? •Environmentally friendly processes Benign Disposal •Sustainability Recycle/Re-use Chemical usage Reduce - Energy usage Hazardous materials, processes Replace - Inefficient processes Non-sustainable components Green Chemistry Technologies and Solutions • What is Green Chemistry? •Chemistry to provide commodities being environmentally friendly and sustainable • How do we know what is Green? • A dip into the Clean/Green technology Pool with some examples. How do we know what is Green? Metrics in Green Chemistry “When you can measure what you are speaking about, and express it in numbers, you know something about it; but when you cannot measure it, when you cannot express it in numbers, your knowledge is of a meagre and unsatisfactory kind; it may be the beginning of knowledge, but you have scarcely, in your thoughts, advanced to the stage of science” William Thompson, Lord Kelvin, (1891) “If you don’t keep score then you are only practising” Metrics in Green Chemistry How do we know what progress we are making? ⇒ E - Factor Amount of waste/kg product: Product tonnage E Factor Bulk Chemicals 104-106 <1 - 5 Fine chemical Industry 102-104 5 - >50 Pharmaceutical Industry 10-103 25 - >100 R.A. Sheldon, Chem & Ind, 1997,12 Metrics in Green Chemistry Preparation of 2-methoxypropane-1,3-diol from glycerol OH OH 2TrCl 2Et N HO OH + + 3 TrO OTr + 2Et3N.HCl [92] [278.5] [101] [137.5] OH OMe MeI Et N Et N.HI TrO OTr + + 3 TrO OTr + 3 [142] [229] OMe OMe TrO OTr + 2AcOH HO OH + 2TrOAc [60] [106] [302] Assuming 100% yields, no reaction or work-up solvents and no reagent excesses 1 kg glycerol produces 1.15 kg 2-methyl ether and 12.04 kg of waste! Atom Economy MW of desired product Atom economy = Σ MWs of all substances produced •Diels-Alder Reaction O O + 100% Atom economy •Wittig Reaction •O _ + C H•2 + Ph3P CH2 + Ph3 P=O 35% Atom economy Safer reactions and reagents- Renewable New Chemistry Feedstocks Catalysis Alternative Solvents Chemical Innovative recycling Membrane Engineering reactors 12 Principles of Green Chemistry • Prevent waste: Design chemical syntheses to prevent waste, leaving no waste to treat or clean up. • Design safer chemicals and products: Design chemical products to be fully effective, yet have little or no toxicity. • Design less hazardous chemical syntheses: Design syntheses to use and generate substances with little or no toxicity to humans and the environment. • Use renewable feedstocks: Use raw materials and feedstocks that are renewable rather than depleting. Renewable feedstocks are often made from agricultural products or are the wastes of other processes; depleting feedstocks are made from fossil fuels (petroleum, natural gas, or coal) or are mined. 12 Principles of Green Chemistry • Use catalysts, not stoichiometric reagents: Minimize waste by using catalytic reactions. Catalysts are used in small amounts and can carry out a single reaction many times. They are preferable to stoichiometric reagents, which are used in excess and work only once. • Avoid chemical derivatives: Avoid using blocking or protecting groups or any temporary modifications if possible. Derivatives use additional reagents and generate waste. • Maximize atom economy: Design syntheses so that the final product contains the maximum proportion of the starting materials. There should be few, if any, wasted atoms. • Use safer solvents and reaction conditions: Avoid using solvents, separation agents, or other auxiliary chemicals. If these chemicals are necessary, use innocuous chemicals. 12 Principles of Green Chemistry • Increase energy efficiency: Run chemical reactions at ambient temperature and pressure whenever possible. • Design chemicals and products to degrade after use: Design chemical products to break down to innocuous substances after use so that they do not accumulate in the environment. • Analyze in real time to prevent pollution: Include in- process real-time monitoring and control during syntheses to minimize or eliminate the formation of byproducts. • Minimize the potential for accidents: Design chemicals and their forms (solid, liquid, or gas) to minimize the potential for chemical accidents including explosions, fires, and releases to the environment. Pharmaceutical Applications Traditional synthesis of ibuprofen O O CHCO2C2H5 ClCH CO C H (CH3CO)2O 2 2 2 5 NaOC H AlCl3 2 5 CHO HC NOH + H H2NOH H2O CN CO2H Ibuprofen Pharmaceutical Applications Alternative synthesis of ibuprofen O (CH3CO2)O H2 HF catalyst OH CO2H CO, Pd Ibuprofen B HC Company Redesign of the Sertraline Process NMe NMe NMe NMe TiCl / MeNH Pd/C, H2 (D)-mandelic acid EtOAc 4 2 EtOH HCl toluene/hexanes THF Cl Cl O Cl Cl Cl Cl Cl Cl + TiO 2 Sertraline Mandelate Sertraline + MeNH4Cl racemis mixture isolated "imine" cis and trans isomers isolated isolated final product Cl Cl NMe NMe NMe NMe MeNH2 PdC/CaCO3 (D)-mandelic EtOAc EtOH + H2O acid H2/EtOH HCl EtOH MeOH rex Cl Cl Cl Cl Cl Cl Cl Cl Sertraline "imine" racemic mixture Sertraline Mandelate isolated not isolated not isolated isolated final product Alternative Synthetic Pathways Sodium iminodisuccinate Biodegradable, environmentally friendly chelating agent Synthesized in a waste-free process Eliminates use of hydrogen cyanide Bayer Corporation and Bayer AG 2001 Alternative Synthetic Pathways Award Winner O O O NaOH NaO ONa O NH3 NaO ONa N O O H O New Chemistry: Synthesis of 4-ADPA Monsanto’s new route: rubber antidegradant 130,000 M tonnes/annum Starting Material: Aniline NH2 Green Chemistry Traditional Chemistry Safer. Organo-halogens used. No Organo-halogens. Waste Minimised -74% less Hazardous Solvent used. organic, 99% less water. High Waste levels. Reusable catalyst employed. Reduced Cost. N NH H 2 Product : 4-ADPA Catalysis Zeolites as Alternatives to Classical Routes • Alumino-silicates • 3D crystalline structure • Uniform pore size • Green applications in > Catalysis > Water treatment > Remediation > Odour control Zeolites: Chemical Composition PRIMARY STRUCTURE Organic or inorganic Exchangeable Acid Zeolites H+ Control: x+ x- • during synthesis M [Al Si O ] z H O • after synthesis x/n x y 2 (x + y ) 2 y/x between 1 and ∞ number
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