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Molecules 2015, 20(12), 21840-21853; doi:10.3390/molecules201219805

Alkylation of Methyl Linoleate with Propene in Ionic Liquids in the Presence of Metal Salts

1
Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, Pisa 56126, Italy
2
ENI Downstream R & D, Development Operations and Technology, S. Donato Milanese (Mi) 20097, Italy
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Jason P. Hallett
Received: 5 November 2015 / Revised: 20 November 2015 / Accepted: 27 November 2015 / Published: 7 December 2015
(This article belongs to the Special Issue Ionic Liquids in Organic Synthesis)
View Full-Text   |   Download PDF [3586 KB, uploaded 7 December 2015]   |  

Abstract

Vegetable oils and fatty acid esters are suitable precursor molecules for the production of a variety of bio-based products and materials, such as paints and coatings, plastics, soaps, lubricants, cosmetics, pharmaceuticals, printing inks, surfactants, and biofuels. Here, we report the possibility of using Lewis acidic ionic liquids (ILs) to obtain polyunsaturated ester dimerization-oligomerization and/or, in the presence of another terminal alkene (propene), co-polymerization. In particular, we have tested the Lewis acidic mixtures arising from the addition of a proper amount of GaCl3 (Χ > 0.5) to two chloride-based (1-butyl-3-methylimidazolium chloride, [bmim]Cl, and 1-butylisoquinolium chloride, [BuIsoq]Cl) or by dissolution of a smaller amount of Al(Tf2N)3 (Χ = 0.1) in 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [bmim][Tf2N]. On the basis of product distribution studies, [bmim][Tf2N]/Al(Tf2N)3 appears the most suitable medium in which methyl linoleate alkylation with propene can compete with methyl linoleate or propene oligomerization. View Full-Text
Keywords: ionic liquid; metal salt; methyl linoleate alkylation ionic liquid; metal salt; methyl linoleate alkylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Pomelli, C.S.; Ghilardi, T.; Chiappe, C.; de Angelis, A.R.; Calemma, V. Alkylation of Methyl Linoleate with Propene in Ionic Liquids in the Presence of Metal Salts. Molecules 2015, 20, 21840-21853.

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