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Esterification of carboxylic acids on cellulosic material: solid state reactions
Luleå University of Technology, Department of Engineering Sciences and Mathematics, Wood Science and Engineering.ORCID iD: 0000-0002-7711-9267
2008 (English)In: Holzforschung, ISSN 0018-3830, E-ISSN 1437-434X, Vol. 62, no 2, p. 136-141Article in journal (Refereed) Published
Abstract [en]

In the present work, the formation of ester linkages in cellulosic materials during drying and heating was addressed. The results indicated that direct ester formation, without anhydride intermediate, occurs between carboxylic acids of suitable structure and cellulosic hydroxyls at 180 degrees C, even after reaction times as short as 5 min. The 2(R)-hydroxybutyric acid is most effective in ester formation, followed by 2-ketobutyric acid and 3-hydroxybutyric acid. Hexanoic acid is less effective and veratric acid produces no esters at all. At lower temperatures, 2-ketobutyric acid is the most reactive compound. One conclusion is that a hydroxyl or keto group in alpha position of the carboxylic acids favours ester formation. Another finding is that three pyrrolidine structures are produced after esterification and aminolysis of 2-ketobutyric acid. One of the structures indicates that 2-ketobutyric acid is reactive in two positions and could therefore be a potential cross-linker. A critical parameter for ester formation is pH, and the results indicate that pH < 2 strongly favours esterification, whereas almost no esters are produced at pH > 5-6. All experiments were performed in a solid-state model system (on cellulosic filter paper) with low moisture content. Esterification of five carboxylic acids was studied. Samples were heated constantly at 180 degrees C for 5 min or gradually from 22 degrees C to 180 degrees C over periods ranging from 5 to 45 min. Quantitative analysis of ester formation between the monocarboxylic acids and the hydroxyl groups of cellulose was performed by means of aminolysis and gas chromatography.

Place, publisher, year, edition, pages
2008. Vol. 62, no 2, p. 136-141
National Category
Bio Materials
Research subject
Wood Physics
Identifiers
URN: urn:nbn:se:ltu:diva-12564DOI: 10.1515/HF.2008.027ISI: 000253853200002Scopus ID: 2-s2.0-38849126090Local ID: bb9817f0-0227-11dd-9241-000ea68e967bOAI: oai:DiVA.org:ltu-12564DiVA, id: diva2:985515
Note
Validerad; 2008; 20080404 (pafi)Available from: 2016-09-29 Created: 2016-09-29 Last updated: 2018-07-10Bibliographically approved

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Pantze, AnnaKarlsson, OlovWestermark, Ulla

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