Publication
Title
Synthesis of levulinic acids from muconic acids in hot water
Author
Abstract
Levulinic acid is a key biorenewable platform molecule. Its current chemical production from sugars is plagued by limited yields, char formation and difficult separations. An alternative and selective route starting from muconic acid via simple heating in water at high temperature (180 degrees C) has been developed. Muconic acid can be obtained from sugars or catechol fermentation. Chemical oxidation of catechol is another possibility which advantageously can also be applied on substituted catechols, hereby providing substituted muconic acids. When applying the disclosed hydrothermal protocol on these substrates hitherto unknown substituted levulinic acids were accessed. In particular, 3-propyllevulinic acid has been synthesized from 4-propylcatechol, prepared from pine wood. This propylated derivative has been used for the synthesis of a 3-propyllevulinate diester, i.e. butane-1,4-diyl bis(4-oxo-3-propylpentanoate), via esterification with 1,4-butanediol. The diester showed superior performance as plasticizer in comparison to the corresponding levulinate diester in both PVC (polyvinyl chloride) and PLA (polylactic acid). It plasticizes equally effective as the notorious commercial phthalate-based benchmark DEHP (di-2-ethylhexyl phthalate) in PVC.
Language
English
Source (journal)
Angewandte Chemie: international edition in English. - Weinheim
Publication
Weinheim : 2023
ISSN
1433-7851
0570-0833
DOI
10.1002/ANIE.202309597
Volume/pages
62 :46 (2023) , p. 1-8
Article Reference
e202309597
ISI
001139366400014
Pubmed ID
37579251
Medium
E-only publicatie
Full text (Publisher's DOI)
Full text (open access)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Research group
Project info
Sustainable Transformations of Biobased Molecules in Water.
Synthesis and transformation of muconic acid into platform molecules starting from biomass (MUCOFORM).
Sustainable reduction reactions in water via in situ hydrogen gas production.
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identifier
Creation 02.10.2023
Last edited 25.04.2024
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