title: Green and selective polycondensation methods toward linear sorbitol-based polyesters: enzymatic versus organic and metal-based catalysis.
abstract: 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 (13) C and (31) P 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.
authors.affiliation: Laboratory of Physical Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, Netherlands.|Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven, Netherlands.
authors.forename: Liliana
authors.initials: L
authors.lastname: Gustini
authors.affiliation: Laboratory of Physical Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, Netherlands. C.LavillaAguilar@tue.nl.
authors.forename: Cristina
authors.identifier: 0000-0002-2946-4146
authors.initials: C
authors.lastname: Lavilla
authors.affiliation: Laboratory of Physical Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, Netherlands.
authors.forename: William W T J
authors.initials: WW
authors.lastname: Janssen
authors.affiliation: Departament d'Enginyeria Química, ETSEIB, Universitat Politècnica de Catalunya, Diagonal 647, 08028, Barcelona, Spain.
authors.forename: Antxon
authors.initials: A
authors.lastname: Martínez de Ilarduya
authors.affiliation: Departament d'Enginyeria Química, ETSEIB, Universitat Politècnica de Catalunya, Diagonal 647, 08028, Barcelona, Spain.
authors.forename: Sebastián
authors.initials: S
authors.lastname: Muñoz-Guerra
authors.affiliation: Laboratory of Physical Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB, Eindhoven, Netherlands.|DSM Coating Resins, Ceintuurbaan 5, Zwolle, Netherlands.
authors.forename: Cor E
authors.initials: CE
authors.lastname: Koning
mesh_terms: D055162:Biocatalysis; D002384:Catalysis; D005656:Fungal Proteins / Q000737:chemistry / Q000378:metabolism*; D055772:Green Chemistry Technology; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry*; D011091:Polyesters / Q000737:chemistry*; D011487:Protein Conformation; D013012:Sorbitol / Q000737:chemistry*; D013696:Temperature
chemical_list: D005656:Fungal Proteins; D009942:Organometallic Compounds; D011091:Polyesters; D013012:Sorbitol; D008049:Lipase; C431349:lipase B, Candida antarctica
keywords: biocatalysis; carbohydrates; polymerization; renewable resources; sustainable chemistry