Intensification and economic and ecological assessment of a biocatalytic oxyfunctionalization processElectronic supplementary information (ESI) available: Supplementary Table A: Criteria for ABC classification; Supplementary Table B: ABC classification of all compounds; Supplementary Table C: Detailed mass-balances for all (S)-styrene oxide production processes; Supplementary Table D: Environmental indices for all (S)-styrene oxide production processes. See DOI: 10.1039/b921896c

Bio-based processes are commonly accepted to be environmentally preferable to chemical alternatives. Reasons include high selectivities, the avoidance of heavy metals, and mild reaction conditions. However, ecological benefits and economic viability have to be verified in each case. Oxygenases are a very attractive enzyme class, allowing selective oxyfunctionalization by introduction of molecular oxygen into hydrocarbons at optical purities unparalleled by traditional chemical methods. Here, styrene monooxygenase from Pseudomonassp. strain VLB120 was used in recombinant Escherichia colifor the production of enantiopure (S)-styrene oxide from styrene. Substrate and product toxicity was attenuated using a two-liquid phase system with bis(2-ethylhexyl)phthalate as organic carrier solvent. By maintaining previously reported productivities for a longer time period, product concentrations were doubled to 36.3 g Ltot−1making it one of the most productive biocatalytic oxyfunctionalization processes. This biotransformation was incorporated along with an appropriate upstream and downstream processing into a complete process scheme and compared with chemical process alternatives. Ecological assessment showed the bioprocess to be superior to two chemical process alternatives and slightly inferior to the third one, with solvent use being the most critical factor. However, the bioprocess performed best in terms of production costs ($10.2 kg−1). This study underlines the importance of a detailed ecological and economic assessment of bioprocesses to verify their sustainability and to identify weak points with respect to environmental and/or economical sustainability. [ABSTRACT FROM AUTHOR]