Catalytic transesterification of cellulose in ionic liquids: Sustainable access to cellulose esters

Schenzel, A., Hufendiek, A., Barner-Kowollik, C., & Meier, M. A. R. (2014) Catalytic transesterification of cellulose in ionic liquids: Sustainable access to cellulose esters. Green Chemistry, 16(6).

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Catalytic transesterifications of cellulose were studied under homogeneous conditions using the ionic liquid 1-butyl-3-methylimidazolium chloride (BMIMCl) as a solvent. Cellulose was thus efficiently converted into cellulose esters employing various methyl esters and 10 mol% of 1,5,7-triazabicyclo[4.4.0]dec-5- ene (TBD) as catalyst. 1H NMR analysis of the products revealed up to 2.3 turnovers of the methyl esters per catalyst molecule, leading to degrees of substitution (DS) of up to 0.69. Although a comparatively low turnover number (TON) is observed, the developed methodology represents the first successful homogeneous catalytic reaction on cellulose. Furthermore, the new method is an important step forward in terms of sustainability, since the BMIMCl-DMSO mixture can be recycled and reused for the reaction, and toxic and corrosive chemicals commonly employed for cellulose esterification (such as anhydrides, acid chlorides and bromides, organic bases, all in overstoichiometric amounts) are avoided. To demonstrate the versatility of this transesterification, an aromatic (cellulose benzoate), an aliphatic (cellulose butyrate), and a fatty acid containing cellulose ester (cellulose 10-undecenoate) were prepared. Additionally, cellulose 10-undecenoate was successfully used for thiol-ene grafting onto reactions employing two thiols for efficient thiol-ene addition reactions. This journal is © the Partner Organisations 2014.

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24 citations in Web of Science®
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ID Code: 99402
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :16
Export Date: 5 September 2016
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131 Karlsruhe, Germany; email:
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DOI: 10.1039/c4gc00312h
ISSN: 14639262
Divisions: Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Jun 2017 17:01

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