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URN: urn:nbn:de:kobv:517-opus-42652
URL: http://opus.kobv.de/ubp/texte_eingeschraenkt_verlag/2010/4265/


Tsukamoto, Junko ; Heabel, Sophie ; Valenca, Gustavo P. ; Peter, Martin ; Franco, Telma

Enzymatic direct synthesis of acrylic acid esters of mono- and disaccharides

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Zugriffsbeschränkung: Universitätsverlag - eingeschränkter Zugriff


Kurzfassung auf Englisch

BACKGROUND: There is an increased need to replace materials derived from fossil sources by renewables. Sugar-cane derived carbohydrates are very abundant in Brazil and are the cheapest sugars available in the market, with more than 400 million tons of sugarcane processed in the year 2007. The objective of this work was to study the preparation of sugar acrylates from free sugars and free acrylic acid, thus avoiding the previous preparation of protected sugar derivatives, such as glycosides, or activated acrylates, such as vinyl acrylate.

RESULTS: Lipase catalyzed esterification of three mono- and two disaccharides with acrylic acid, in the presence or absence of molecular sieves was investigated. The reactions were monitored by high-performance liquid chromatography (HPLC) and the products were analyzed by matrix-assisted laser desorption ionization–time of flight (MALDI-TOF) mass spectrometry. The main products are mono- and diacrylates, while higher esters are formed as minor products. The highest conversion to sugar acrylates was observed for the D-glucose and D-fructose, followed by D-xylose and D-maltose. Molecular sieves had no pronounced effect on the conversion

CONCLUSIONS: A feasible method is described to produce and to characterize sugar acrylates, including those containing more than two acrylate groups. The process for production of these higher esters could potentially be optimized further to produce molecules for cross-linking in acrylate polymerization and other applications. The direct enzymatic esterification of free carbohydrates with acrylic acid is unprecedented.

Freie Schlagwörter (englisch): carbohydrate esters , enzymatic esterification , acrylic acid esters , MALDI-TOF mass spectrometry
Institut: Institut für Chemie
DDC-Sachgruppe: Chemie
Dokumentart: c Postprint
Schriftenreihe: Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe, ISSN 1866-8372
Band Nummer: paper 106
Quelle: Journal of Chemical Technology & Biotechnology 83 (2008) 11, S. 1486 - 1492, DOI 10.1002/jctb.1983
Sprache: Englisch
Erstellungsjahr: 2008
Publikationsdatum: 12.05.2010
Bemerkung:
The original publication is available at www3.interscience.wiley.com:
Journal of Chemical Technology & Biotechnology. - 83 (2008) Issue 11, p. 1486-1492
ISSN 1526-498X, 0142-0356, 0268-2575
DOI 10.1002/jctb.1983
Lizenz: Diese Nutzungsbedingung gilt nicht, wenn in den Metadaten eine modifizierende Lizenz genannt ist. Keine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht


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