Lipase-Catalyzed Polycondensation in Water: A New Approach for Polyester Synthesis

Abstract

The lipase-catalyzed polycondensation of sebacic aid and 1,4-butanediol can be performed in a biphasic reaction system composed of an aqueous reaction phase and an organic extraction phase. The shift of the equilibrium to higher product yields can be realized by the integrated product removal (IPR). In this biphasic reaction system the product yield, molecular weight and polydispersity is depending on the partitioning of the substrates and the product between the phases. By the biphasic approach substrate inhibition as well as molecular weight and polydispersity can be controlled by medium engineering. The polyester concentration can be increased up to 98% by optimising the reaction conditions. The molecular weight is limited in the biphasic system due to its removal while the polydispersity is independent of the reaction conditions but connected to the biphasic approach. Additional to the conversion the partition coefficients have been investigated either experimentally and via calculation by the quantum chemical program COSMO-RS.

Biosynthesis of myristyl serinate by immobilized Candida antarctica lipase in two-phase system

“…However in the present study, myristyl alcohol is long-chain alcohol and no inhibiting effect of long-chain alcohol was occurred according to our study data. There are similar results showed that long-chain acids had also no inhibiting effect on lipase activity [19,20].…”

“…By increasing the organic phase from 1 to 4, the product concentration raised from 47.8% to 71.6%, with an increase of 23.8%. Duwensee et al mentioned that a higher capacity of the organic phase leads to a higher driving force transfer due to a larger difference of its chemical potential in the two-phase system [19]. In biphasic systems, a high driving force for the product to pass into the organic phase leads to the higher yield for the n-hexan e Dich lorometh ane Aceton e TH F Cyclo hexa ne esterification.…”

“…(2) In case of a higher partition coefficient for the products an integrated product removal occurs, which potentially leads to higher grade of conversion [19].…”

“…The pH value of phosphate buffer affects lipase activity and the phase partitioning of all compounds in the solvent [19]. Myristyl serinate content in the crude reaction product ranged between 18.36% and 72.19% with pH value varied from 5.5 to 8.5.…”

Polymer precursors from catalytic reactions of natural oils

“…[66][67][68] Finally, polyesters from natural oils can be obtained from biologically-based reactions. 69,70 However, these processes are out of the scope of the present introduction.…”