University of Oulu

ACSOmega2019, 4, 15702−15710

Carbamation of starch with amine using dimethyl carbonate as coupling agent

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Author: Sirviö, Juho Antti1; Heiskanen, Juha P.2
Organizations: 1Fibre and Particle Engineering Research Unit, University of Oulu, P.O. Box 4300,FI-90014 Oulu, Finland
2Research Unit of Sustainable Chemistry, University of Oulu, P.O. Box 4300,FI-90014 Oulu, Finland
Format: article
Version: published version
Access: open
Online Access: PDF Full Text (PDF, 2.5 MB)
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Language: English
Published: American Chemical Society, 2019
Publish Date: 2019-12-03


A one-pot coupling of starch with alkyl amine was studied using dimethyl carbonate (DMC) as the coupling agent. Although reaction occurred without a catalyst (24 h, 70 °C), different catalysts, namely, imidazole, tetramethylguanidine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and combinations thereof were investigated to improve the reaction efficiency. When 20 mol % DBU was used as a catalyst, the degree of substitution (DS) could be improved from 0.05 to 0.15 compared to the noncatalyzed reaction. When the amount of DBU was decreased to 5 mol %, catalytical activity remained, albeit with a slightly lower DS (0.09). Temperature did not have a significant effect on the DS but it could be used to alter the solubility of the product. Based on chemical analysis, the alkyl group was attached to starch by the formation of a carbamate group. As the carbonyl carbon in the carbamate originated from DMC, which, in turn, can be produced from carbon dioxide on an industrial scale, the current study provides a conventional way to utilize carbon dioxide-based chemicals in the functionalization of a natural polymer. DMC is also biodegradable and classified as a nonvolatile organic component, making it an environmentally desirable coupling agent.

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Series: ACS omega
ISSN: 2470-1343
ISSN-E: 2470-1343
ISSN-L: 2470-1343
Volume: 4
Issue: 13
Pages: 15702 - 15710
DOI: 10.1021/acsomega.9b02350
Type of Publication: A1 Journal article – refereed
Field of Science: 116 Chemical sciences
Funding: J.A.S. would like to thank the Kone Foundation for its financial support.
Copyright information: © 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium,provided the author and source are cited.