Green and selective polycondensation methods toward linear sorbitol-based polyesters: enzymatic versus organic and metal-based catalysis

Renewable polyesters derived from a sugar alcohol (i.e., sorbitol) were synthesized by solvent-free polycondensation. The aim was to prepare linear polyesters with pendant hydroxyl groups along the polymer backbone. The performance of the sustainable biocatalyst SPRIN liposorb CALB [an immobilized f...

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Bibliographic Details
Published in:ChemSusChem
Main Authors: Gustini, Liliane, Lavilla, Cristina, Janssen, William, Martínez de Ilarduya Sáez de Asteasu, Domingo Antxon, Muñoz Guerra, Sebastián, Koning, Cor
Other Authors: Universitat Politècnica de Catalunya. Departament d'Enginyeria Química, Universitat Politècnica de Catalunya. POL - Polímers Industrials Avançats i Biopolímers Tecnològics
Format: Article in Journal/Newspaper
Language:English
Published: 2016
Subjects:
Àrees temàtiques de la UPC::Enginyeria química
Biotechnology
Biocatalysis
Renewable natural resources
Polymerization
carbohydrates
renewable resources
sustainable chemistry
Biotecnologia
Catàlisi
Polimerització
Recursos naturals renovables
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2117/90682
https://doi.org/10.1002/cssc.201600626
Description
Summary:Renewable polyesters derived from a sugar alcohol (i.e., sorbitol) were synthesized by solvent-free polycondensation. The aim was to prepare linear polyesters with pendant hydroxyl groups along the polymer backbone. The performance of the sustainable biocatalyst SPRIN liposorb CALB [an immobilized form of Candida antarctica lipase B (CALB); SPRIN technologies] and the organo-base catalyst 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) were compared with two metal-based catalysts: dibutyl tin oxide (DBTO) and scandium trifluoromethanesulfonate [also known as scandium triflate, Sc(OTf)3]. For the four catalytic systems, the efficiency and selectivity for the incorporation of sorbitol were studied, mainly using 13C and 31P NMR spectroscopies, whereas side reactions, such as ether formation and dehydration of sorbitol, were evaluated using MALDI-TOF-MS. Especially the biocatalyst SPRIN liposorb CALB succeeded in incorporating sorbitol in a selective way without side reactions, leading to close-to-linear polyesters. By using a renewable hydroxyl-reactive curing agent based on l-lysine, transparent and glossy poly(ester urethane) networks were successfully synthesized offering a tangible example of bio-based coatings. Peer Reviewed Postprint (author's final draft)

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