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16 P. T. Anastas and E. S. Beach Figure 10. Peroxotungstanate immobilized on ionic liquid- modified silica, an example of supported ionic liquid phase catalysis (107). (102,103). The wide range of IL materials reported highlights the ‘‘designer’’ nature of the new solvents; it is hoped that the growing body of information related to IL toxicity (104) will be used in designing the next generation of ILs. Improved biodegradabil- ity and recyclability are also suggested research goals for the IL field (105). Supported ionic liquid phase (SILP) catalysis is one area of IL research that has achieved additional green chemistry goals such as reduced solvent use and catalyst recyclability and reusability. The SILP catalyst materials are stable and heterogeneous-like but can achieve high activity and selectivity more typical of heterogeneous catalysts. These catalyst systems have been applied to effect a wide variety of synthetic transformations (106). Design of safer chemicals The publication of Silent Spring by Rachel Carson in 1962 was one of the early alerts to chemists about the toxicity of the products they design. Besides DDT, alarms have been sounded for many chemicals and classes of chemicals, for example vinyl chloride (108) and organochlorine compounds in general (109), perfluorooctanoic acid (110), polybrominated diphe- nyl ethers (111), phthalate plasticizers (112), and bisphenol A (113). The phenomenon of endocrine disruption by manmade chemicals has emerged as a leading threat to sustainable civilization (114,115). Compared to 1962, chemists now have more informa- tion available to design chemicals that are less likely to result in toxicity ‘‘surprises.’’ Considerations for design of safer chemicals have been outlined, includ- ing: environmental mobility and fate; uptake, meta- bolism, and excretion by organisms; and avoiding toxic functional groups (116). Many compendia of chemical toxicity informa- tion have been published (117), such as A Compre- hensive Guide to the Hazardous Properties of Chemical Substances (Wiley: Hoboken, NJ, 2007) and Hand- book of Green Chemicals (Synapse Information Re- sources, Inc.: Endicott, NY, 2004). Systems for benchmarking chemicals according to green proper- ties have been developed such as GreenScreen (118), and CleanGredients (for product formulations) (119). Some industries are adopting similar metrics, notably SC Johnson & Son, Inc., which employs a proprietary ‘Greenlist’ methodology to develop safer chemical formulations for its commercial products (120). Some examples of design for reduced toxicity by green chemists in the last two decades: . Dimethyl carbonate has been developed as an alternative to phosgene for carbonylation and alkyl halides for alkylation reactions. Dimethyl carbonate is non-toxic and biodegradable (121). Phosgene can also be eliminated from isocyanate production by generating isocyanates from CO2, amines, and o-sulfobenzoic acid anhydride (122) (Figure 11). . Polymers of N-vinylformamide have been applied as alternatives to polyacrylamides. Acrylamide mono- mer is a potential carcinogen and neurotoxin (123). . Atom transfer radical polymerization, a widely used technique for living radical polymerization, can be performed using significantly reduced amounts of Figure 11. Phosgene-free synthesis of isocyanates. The o-sulfobenzoic acid salt is recyclable (122).PDF Image | Green chemistry: the emergence of a transformative framework
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