Journal
PURE AND APPLIED CHEMISTRY
Volume 91, Issue 3, Pages 397-408Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2018-1015
Keywords
biobased terpolymer; biocatalysis; dimethyl furan-2,5-dicarboxylate; dimethyl itaconate; lipase; POC-17
Categories
Funding
- Romanian Authority for Scientific Research and Innovation, CNCS/CCCDI - UEFISCDI within PNCDI III [PN-III-P22.1-PED-2016-0168]
Ask authors/readers for more resources
2,5-Furandicarboxylic acid and itaconic acid are both important biobased platform chemicals and their terpolymer with 1,6-hexanediol (HDO) can be the starting point for a new class of reactive polyesters, with important applications. The green synthetic route developed in this study involves a biocatalytic condensation polymerization reaction of dimethyl furan-2,5-dicarboxylate (DMFDC) and dimethyl itaconate (DMI) with HDO in toluene at 80 degrees C, using commercial immobilized lipases from Candida antarctica B. In the best conditions, the formed polymer product was isolated with more than 80 % yield, containing about 85 % terpolymer with average molecular mass of about 1200 (M-n, calculated from MALDI-TOF MS data) and 15 % DMFDC_HDO copolymer. Considering the higher reactivity of DMFDC, the composition of the synthesized polymer can be directed by adjusting the molar ratio of DMFDC and DMI, as well as by extending the reaction time. Structural analysis by NMR demonstrated the regioselective preference for the carbonyl group from DMI adjacent to the methylene group. The biocatalyst was successfully reused in multiple reaction cycles.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available