Chiral polyesters by dynamic kinetic resolution polymerization

POLY 395

Iris Hilker, iris.hilker@dsm.com1, Gerard K. M. Verzijl, gerard.verzijl@dsm.com2, Anja R. A. Palmans, a.palmans@tue.nl3, and Andreas Heise, andreas.heise@dsm.com1. (1) DSM Performance Materials, P.O. Box 18, Geleen, 6160 MD, Netherlands, (2) DSM Pharma Chemicals, P.O. Box 18, Geleen, 6160 MD, Netherlands, (3) Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P.O. Box 513, Eindhoven, 5600 MB, Netherlands
Chiral polyesters are synthesized combining dynamic kinetic resolution (DKR) with enzymatic polymerization. The reaction mixture comprises a racemic mixture of a chiral diol (α,α′-dimethyl-1,4-benzenedimethanol) and dimethyl adipate as acyl donor. Due to the high stereoselectivity of Candida antarctica lipase B (CALB) the (S)-hydroxy groups of the diol are practically non-reactive in an enzymatic reaction. The system of CALB and a ruthenium catalyst for the racemisation of hydroxy groups was already shown to be successful in DKR of small molecules. Polymerization was achieved in a one-pot process by combination of the enzymatic reaction with an in-situ racemization process. Results from chiral gas chromatography and optical rotation measurements confirm the success of the concurrent reaction.

Biocatalysis in Polymer Science
1:30 PM-4:45 PM, Tuesday, 12 September 2006 San Francisco Marriott -- Salon 12/13, Oral

Division of Polymer Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006