Carbon dioxide, supercritical, enzymatic

Nakamura, K. Hoshino, T. Novel Utilization of Supercritical Carbon Dioxide for Enzymatic Reaction in Food Processing. In Advances in Food Engineering Singh, R. P., Wirakartakusumah, M. A., Eds. CRC Press Boca Raton, FL, 1992 pp. 257-262. 

The use of supercritical carbon dioxide for enzymatic reactions is limited by the difficulty of dissolving relatively polar substrates. To increase the solubility of polar compounds, Castillo et al. [84] complexed the substrate with phenylboronic acid or immobilized polar reactants on silica gel. As model reaction the esterification of oleic acid with... 

M Taniguchi, M Kamihara, T Kobayashi. Effect of treatment with supercritical carbon dioxide on enzymatic activity. Agric Biol Chem 51 593-594, 1987. 

Details are given of the enzymatic transformation of polycaprolactone into repolymerisable oligomers in supercritical carbon dioxide. The object was to establish a sustainable chemical recycling system for polycaprolactone. 14 refs. 

Another environmental issue is the use of organic solvents. The use of chlorinated hydrocarbons, for example, has been severely curtailed. In fact, so many of the solvents favored by organic chemists are now on the black list that the whole question of solvents requires rethinking. The best solvent is no solvent, and if a solvent (diluent) is needed, then water has a lot to recommend it. This provides a golden opportunity for biocatalysis, since the replacement of classic chemical methods in organic solvents by enzymatic procedures in water at ambient temperature and pressure can provide substantial environmental and economic benefits. Similarly, there is a marked trend toward the application of organometal-lic catalysis in aqueous biphasic systems and other nonconventional media, such as fluorous biphasic, supercritical carbon dioxide and ionic liquids. ... 

The study of enzymatic esterification by an immobilized lipase in supercritical carbon dioxide (SCCO2) and in n-hexane (Marty et al., 1994). 

Among potentially interesting solvents for enzymatic catalysis, carbon dioxide is the most widely nsed snpercritical fluid. However, there is a growing interest in using other supercritical fluids (e.g., ethylene, fluoroform, ethane, sulfur hexafluoride, and near-critical propane) (Kamat et al., 1995b). 

Bernard, P. Barth, D. Internal Mass Transfer Limitation During Enzymatic Esterification in Supercritical Carbon Dioxide and Hexane. Biocatal. Biotransform. 1995, 12, 299-308. 

Bernard, P. Barth, D. Perrut, M. Internal Mass Transfer Limitation on Enzymatic Esterification in Supercritical Carbon Dioxide. In High Pressure and Biotechnology, Balny, C., Hayashi, R., Heremans, K., Masson, P., Eds. John Libbey U.K., 1992 pp. 451 155. 

Chi, Y. M. Nakamura, K. Yano, T. Enzymatic Interestification in Supercritical Carbon Dioxide. Agric. Biol. Chem. 1988, 52, 1541-1550. 

Dumont, T. Barth, D. Corbier, C. Branlant, G. Perrut, M. Enzymatic Reaction Kinetic Comparison in an Organic Solvent and in Supercritical Carbon Dioxide. Biotechnol. Bioeng. 1992, 39, 329-333. 

Kamat, S. Critchley, G. Beckman, E. J. Russell, A. J. Biocatalytic Synthesis of Acrylates in Organic Solvents and Supercritical Fluids HI. Does Carbon Dioxide Covalently Modify Enzymes Biotechnol. Bioeng. 1995, 46, 610-620. Kamihira, M. Taniguchi, M. Kobayashi, T. Synthesis of Aspartame Precursors by Enzymatic Reaction in Supercritical Carbon Dioxide. Agric. Biol. Chem. 1987, 51, 3427-3428. 

Michor, H. Marr, R. Gamse, T. Enzymatic Catalysis in Supercritical Carbon Dioxide Effect of Water Activity. High Pressure Chem. Eng. 1996a, 12, 115-120. 

Michor, H. Marr, R. Gamse, T. Schilling, T. Klingsbichel, E. Schwab, H. Enzymatic Catalysis in Supercritical Carbon Dioxide Comparison of Different Lipases and a Novel Esterase. Biotechnol. Lett. 1996b, 18, 79-84. Miller, D. A. Blanch, H. W. Prausnitz, J. M. Enzyme-Catalyzed Interesterification of Triglycerides in Supercritical Carbon Dioxide. Ind. Eng. Chem. Res. 1991, 30, 939-946. 

Van Eijs, A. M. M. de Jong, J. P. L. Doddema, H. J. Lindeboom, D. R. Enzymatic Transesterification in Supercritical Carbon Dioxide. In Proceedings of the International Symposium on Supercritical Fluids Nice, France, 1988 pp. 933-942. 

Yoon, S. H. Nakaya, H. Ito, O. Miyawaki, O. Park, K. H. Nakamura, K. Effects of Substrate Solubility in Interesterification with Riolein by Immobilized Lipase in Supercritical Carbon Dioxide. Biosci. Biotechnol. Biochem. 1998, 62, 170-172. Yu, Z. R. Rizvi, S. S. H. Zollweg, J. A. Enzymatic Esterification of Fatty Acid Mixtures from Milk Fat and Anhydrous Milk Fat with Canola Oil in Supercritical Carbon Dioxide. Biotechnol. Prog. 1992, 8, 508-513. 

Kumar, R., G. Madras and J. Modak, Enzymatic Synthesis of Ethyl Palmitate in Supercritical Carbon Dioxide, Industrial Engineering Chemistry Research, 43, 1568-1573 (2004). 

Matsumura, S., H. Ebata, R. Kondo and K. Toshima, Organic Solvent-Free Enzymatic Transformation of Poly(Epsilon-Caprolactone) into Repolymerizable Oligomers in Supercritical Carbon Dioxide, Macromolecular Rapid Communications, 22, 1326-1329 (2001). 

Reetz, M.T., W. Wiesenhofer, G. Francio and W. Leitner, Continuous Flow Enzymatic Kinetic Resolution and Enantiomer Separation Using Ionic Liquid/Supercritical Carbon Dioxide Media, Advanced Synthesis Catalysis, 345, 1221-1228 (2003). 

In biphasic reactors or two-phase partitioning bioreactors (TPPB), the substrate is located mostly in the immiscible phase and diffuses to the aqueous phase. The enzyme catalyzes conversion of the substrate at the interface and/or in the aqueous phase. The product/s of the reaction then may partition to the organic phase. The system is self-regulated, as the substrate delivery to the aqueous phase is only directed by the partitioning ratio between the two phases and the enzymatic reaction rate [53]. The use of ionic liquid/supercritical carbon dioxide for enzyme-catalyzed transformation is gaining attention [69]. 

H.J. Doddema, et al. Enzymatic reactions in supercritical carbon dioxide and integrated product-recovery. 5th European Congress on Biotechnology, Christiansen et al. (eds.), Copenhagen, 1990. 

Supercritical Carbon Dioxide as a Medium for Enzymatically Catalyzed Reaction... 

The present work reports results and observations on the enzymatic synthesis of oleyl oleate (which is a synthetic analogue of jojoba oil) in supercritical carbon dioxide. Special stress was laid on the comparison between batch and continuous systems for the above mentioned synthesis. Influence of different reaction parameters on the reaction yield and initial reaction rates was studied. 

Reaction performance. Supercritical carbon dioxide was used as a reaction media for the enzymatic synthesis of oleyl oleate directly from oleic acid and oleyl alcohol. Reaction was catalyzed by immobilized lipase from Rhizomucor miehei-Ltpozyme IM. Reactions were carried out in the high pressure batch and continuous reactor. 

Enzymatic Reaction in Supercritical Carbon Dioxide Internal Mass Transfer Limitation... 

Enzymatic reactions in non-aqueous solvents are subjected to a wide interest. A particular class of these solvents is the supercritical fluid (1) such as carbon dioxide that has many advantages over classical organic solvents or water no toxicity, no flammability, critical pressure 7.38 Mpa and temperature 31°C, and allowing high mass transfer and diffusion rates. 

Enzymatic Catalysis in Supercritical Carbon Dioxide Effect of Water... 

Many enzymatic processes can be of practical value, if they are carried out in anhydrous media instead of water. While biocatalysis in organic solvents is well established, the use of supercritical fluids, in particular supercritical carbon dioxide (SC-CO2), is still restricted to research on laboratory scale. 

The employment of catalytic methodologies - homogeneous, heterogeneous and enzymatic - in water or supercritical carbon dioxide as the reaction medium holds much promise for the development of a sustainable chemical manufacturing industry. Water is cheap, abundantly available, non-toxic and non-inflammable and the use of aqueous biphasic catalysis provides an ideal basis for recovery... 

Habulin, M., Sabeder, S., Sampedro, M.A., and Knez, Z. 2008. Enzymatic synthesis of citronellol laurate in organic media and in supercritical carbon dioxide. Biochemical Engineering Journal, 42 6-12. 

Romero, M.D. Calvo, L. Alba, C. Habulin, M. Primozic, M. Knez, Z. Enzymatic synthesis of isoamyl acetate with immobilized Candida ant-arc tica lipase in supercritical carbon dioxide. J. Supercritic. Fluids 2005, 33 (1), 77-84. 

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