Preparation of (S)-1-halo-2-octanols using ionic liquids and biocatalysts
2009
Oromí Farrús, Mireia | Eras i Joli, Jordi | Sala i Martí, Núria | Torres i Grifo, Mercè | Canela i Garayoa, Ramon
Preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol was carried out by the enzymatic hydrolysis of halohydrin palmitates using biocatalysts. Halohydrin palmitates were prepared by various methods from palmitic acid and 1,2-octanediol. A tandem hydrolysis was carried out using lipases from Candida antarctica (Novozym® 435), Rhizomucor miehei (Lipozyme IM), and “resting cells” from a Rhizopus oryzae strain that was not mycotoxigenic. The influence of the enzyme and the reaction medium on the selective hydrolysis of isomeric mixtures of halohydrin esters is described. Novozym® 435 allowed preparation of (S)-1-chloro-2-octanol and (S)-1-bromo-2-octanol after 1–3 h ofreaction at 40 °C in [BMIM][PF6].
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