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18 P. T. Anastas and E. S. Beach with properties comparable to polystyrene and poly(methyl methacrylate) (140). . The DNA base thymine is known to undergo 2p 2p photocyclization, so incorporation of thymine into synthetic polymers presents opportunities for reversible crosslinking. Polymers of vinylbenzyl thymine are promising photoresistant materials that allow for water-based processing. Use of thymine crosslinking in biodegradable polymers may enhance durability (141). . Defatted soy flour, an inexpensive commercial product consisting mainly of soy protein and carbohydrates, can be crosslinked and used in biodegradable composite materials with plant fibers such as flax, hemp, or bamboo. The environmen- tally friendly composites show promise as a building material that could replace non-degradable compo- sites such as polypropylene/glass (142). Soy flour has also been chemically modified to mimic adhe- sive proteins found in mussels; the resulting material has been commercialized as a wood adhesive, replacing toxic urea-formaldehyde resins conven- tionally used in plywood and particleboard (143). . Cargill developed a commercial process for con- verting vegetable oils into polyols for manufactur- ing polyurethane foam, replacing petroleum-derived polyols. In addition to reducing dependence on non- renewable feedstocks, the mild process conditions save energy (144). . Biomass-derived g-valerolactone (Figure 12) has properties that make it an ideal sustainable liquid fuel: it has a low melting point, high boiling point and flash point, low vapor pressure, minimal peroxide formation after prolonged storage, and can be blended with gasoline. It is a naturally occurring chemical found in fruits, and has been used as a food additive. It is miscible with water and biodegradable (145,146). Renewable resources are at the heart of efforts to develop biodegradable polymers. Biodegradable plas- tics can be produced from biopolymers such as Figure 12. g-Valerolactone, a biomass-derived liquid fuel (145,146). cellulose and starches. Polyester materials like poly- hydroxylalkanoates (PHAs) and poly(lactic acid) (PLA) have also been successful. Water-soluble biodegradable polymers include chemically modified cellulose and starches, microbially produced poly- saccharides (e.g. xanthan and pullulan), and poly (amino acid)s (147). PHAs have been commercialized by Metabolix and Archer Daniel Midlands Co., with a facility under construction for producing 100 million pounds per year (148). The process relies on geneti- cally engineered microbes, achieving the polymer synthesis through fermentation of the renewable raw materials (149). Large-scale production of PLA was pioneered by NatureWorks, owned by Cargill. The production process has been noted for following all Twelve Principles of Green Chemistry in its avoidance of organic solvent, high yields achieved by efficient catalysis, and waste reduction through recycle streams. The process is estimated to use 2050% less petroleum resources compared to conventional poly- mers (150). Lactic acid is typically derived from corn, but it can be derived from other materials as well, for example waste sugarcane bagasse (151). Composites of PLA have been developed using fillers made from renewable resources. Polymer composites derived from fossil fuels are non-degradable and difficult to recycle. While PLA itself is currently more expensive than conventional polymers, the use of plant-derived fillers makes the costs of composites competitive. Sugar beet pulp and residue from oilseed crops are examples of low-cost fillers. Milkweed showed a plasticizing effect, imparting ductility to PLA (152,153). Utilization of process wastes is another way to reduce dependence on petroleum feedstocks. Restau- rant oil waste can undergo fermentation to produce large quantities of sophorlipids, natural surfactants that also have cosmetic and therapeutic properties (154). Cashew nut shell liquid (CNSL), a waste product of the cashew nut industry, is distilled to give pre- dominantly cardanol, a mixture of long-chain alkyl- phenol oils. Cardanol modified with benzoxazine has been used to prepare biocomposites with jute fibers, resulting in materials with useful mechanical proper- ties (155). Cardanol has also been used as a non- petroleum feedstock for non-covalent synthesis of organic nanotubes (156). Agricultural byproducts such as rice and nut hulls, fruit peels, and olive mill wastewater contain phenolic compounds with high antioxidant activity (157). These natural anti-oxidants are alternatives to the food additives butylated hydro- xyanisole (BHA), butylated hydroxytoluene (BHT), and t-butylhydroquinone (TBHQ), synthetic antiox-PDF Image | Green chemistry: the emergence of a transformative framework
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