An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates

Wedde S, Rommelmann P, Scherkus C, Schmidt S, Bornscheuer UT, Liese A, Gröger H (2017)
GREEN CHEMISTRY 19(5): 1286-1290.

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Abstract
A novel synthetic route towards the polymer poly-epsilon-caprolactone based on a chemoenzymatic reaction sequence was developed. Initial hydrogenation of phenol to cyclohexanol gave a crude product, which was directly used without work-up for a subsequent biocatalytic double oxidation towards epsilon-caprolactone by means of an alcohol dehydrogenase and a monooxygenase. In order to overcome product inhibition effects, an in situ-product removal strategy via extraction of epsilon-caprolactone from an aqueous reaction medium with an organic solvent in the presence of a permeable polydimethylsiloxane membrane was applied. Furthermore, this in situ-product removal was combined with lipase-catalyzed polymerization in the organic phase at 25 degrees C. The obtained crude product contained a polymer fraction with a degree of polymerization comparable to commercial poly-epsilon-caprolactone.
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Wedde S, Rommelmann P, Scherkus C, et al. An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates. GREEN CHEMISTRY. 2017;19(5):1286-1290.
Wedde, S., Rommelmann, P., Scherkus, C., Schmidt, S., Bornscheuer, U. T., Liese, A., & Gröger, H. (2017). An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates. GREEN CHEMISTRY, 19(5), 1286-1290. doi:10.1039/c6gc02529c
Wedde, S., Rommelmann, P., Scherkus, C., Schmidt, S., Bornscheuer, U. T., Liese, A., and Gröger, H. (2017). An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates. GREEN CHEMISTRY 19, 1286-1290.
Wedde, S., et al., 2017. An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates. GREEN CHEMISTRY, 19(5), p 1286-1290.
S. Wedde, et al., “An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates”, GREEN CHEMISTRY, vol. 19, 2017, pp. 1286-1290.
Wedde, S., Rommelmann, P., Scherkus, C., Schmidt, S., Bornscheuer, U.T., Liese, A., Gröger, H.: An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates. GREEN CHEMISTRY. 19, 1286-1290 (2017).
Wedde, Severin, Rommelmann, Philipp, Scherkus, Christian, Schmidt, Sandy, Bornscheuer, Uwe T., Liese, Andreas, and Gröger, Harald. “An alternative approach towards poly-epsilon-caprolactone through a chemoenzymatic synthesis: combined hydrogenation, bio-oxidations and polymerization without the isolation of intermediates”. GREEN CHEMISTRY 19.5 (2017): 1286-1290.
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