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

作者：Wedde Severin; Rommelmann Philipp; Scherkus Christian; Schmidt Sandy; Bornscheuer Uwe T; Liese Andreas^*; Groeger Harald

来源：Green Chemistry, 2017, 19(5): 1286-1290.

DOI：10.1039/c6gc02529c

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.

• 出版日期2017-3-7