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Issue 6, 2008
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Synthesis of cyclic acetals (ketals) from oleochemicals using a solvent free method

Kenneth M. Doll*a  and  Sevim Z. Erhana  
Author affiliations

* Corresponding authors

a Food and Industrial Oil Research Unit, National Center for Agricultural Utilization Research, United States Department of Agriculture, Agricultural Research Service, 1815 N. University St., Peoria, IL, USA
E-mail: Kenneth.Doll@ars.usda.gov
Fax: 309-681-6340
Tel: 309-618-6103

Abstract

The reaction selectivities of acid catalyzed ring opening reactions of epoxidized methyl oleate (methyl 9,10-epoxy stearate; EMO), to form either ketal (acetal) or branched ester products have been studied. We have produced methyl 9-(2-butyl-2-methyl-5-octyl-1,3-dioxolan-4-yl) nonanoate (hexanone methyl stearate acetal, HMSA), an oleochemically based ketal (acetal), in 83% isolated yield; from epoxidized methyl oleate and 2-hexanone. Utilizing our reaction chemistry, we have also been able to demonstrate the relative selectivities, in competitive experiments, by reacting EMO with 2-pentanone and octanoic acid. Finally, by controlling temperature and acid concentration, we were able to control the product distribution of the reaction of EMO with the bi-functional levulinic acid. Either the ketal (acetal), or the branched ester product could be favored. This research may help lead to the formation of new hydrophobic molecules for the synthesis of new surfactants from oleochemicals.

Graphical abstract: Synthesis of cyclic acetals (ketals) from oleochemicals using a solvent free method

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Publication details

The article was received on 28 Feb 2008, accepted on 09 Apr 2008 and first published on 12 May 2008


Article type: Paper
DOI: 10.1039/B803513J
Green Chem., 2008,10, 712-717

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    Synthesis of cyclic acetals (ketals) from oleochemicals using a solvent free method

    K. M. Doll and S. Z. Erhan, Green Chem., 2008, 10, 712
    DOI: 10.1039/B803513J

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