Jump to main content
Jump to site search

Issue 4, 2014
Previous Article Next Article

Polyketoesters from oleic acid. Synthesis and functionalization

Author affiliations

Abstract

In this study, we exploited the reactivity of the methyl oleate enone derivative for the conversion of this renewable raw material to ketone-containing hydroxyesters. The radical-mediated thiol–ene addition to the conjugated double bonds has been investigated and low yields were obtained due to secondary reactions. The thiol-Michael addition under acidic and basic/nucleophilic conditions was also examined. While using vanadyl triflate (VO(OTf)2), a slight excess of thiol was necessary to complete the reaction, by using both basic/nucleophilic catalysts 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), quantitative conversion was achieved under stoichiometric conditions in shorter reaction times. The obtained hydroxyester, carrying sulphide and ketone functional groups, was used to obtain polyesters by Novozyme-435 enzymatic polymerization. The coupling between the ketone group of the repeating unit and a model oxyamine has been used to demonstrate the polyketoester functionalization via oxime formation.

Graphical abstract: Polyketoesters from oleic acid. Synthesis and functionalization

Back to tab navigation

Article information


Submitted
09 Jul 2013
Accepted
10 Sep 2013
First published
10 Sep 2013

Green Chem., 2014,16, 1847-1853
Article type
Paper

Polyketoesters from oleic acid. Synthesis and functionalization

M. Moreno, G. Lligadas, J. C. Ronda, M. Galià and V. Cádiz, Green Chem., 2014, 16, 1847
DOI: 10.1039/C3GC41346B

Social activity

Search articles by author

Spotlight

Advertisements