title: Alkylation of Methyl Linoleate with Propene in Ionic Liquids in the Presence of Metal Salts.
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.
authors.affiliation: Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, Pisa 56126, Italy. christian.pomelli@unipi.it.
authors.forename: Christian Silvio
authors.initials: CS
authors.lastname: Pomelli
authors.affiliation: Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, Pisa 56126, Italy. tiz.ghilardi@gmail.com.
authors.forename: Tiziana
authors.initials: T
authors.lastname: Ghilardi
authors.affiliation: Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, Pisa 56126, Italy. cinzia.chiappe@farm.unipi.it.
authors.forename: Cinzia
authors.initials: C
authors.lastname: Chiappe
authors.affiliation: ENI Downstream R &amp; D, Development Operations and Technology, S. Donato Milanese (Mi) 20097, Italy. alberto.de.angelis@eni.com.
authors.forename: Alberto Renato
authors.initials: AR
authors.lastname: de Angelis
authors.affiliation: ENI Downstream R &amp; D, Development Operations and Technology, S. Donato Milanese (Mi) 20097, Italy. vincenzo.calemma@eni.com.
authors.forename: Vincenzo
authors.initials: V
authors.lastname: Calemma
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D005708:Gallium / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry; D058116:Lewis Acids; D008041:Linoleic Acids / Q000737:chemistry*
chemical_list: D000475:Alkenes; D052578:Ionic Liquids; D058116:Lewis Acids; D008041:Linoleic Acids; C005575:methyl linoleate; C034163:gallium chloride; C013658:propylene; D005708:Gallium
keywords: ionic liquid; metal salt; methyl linoleate alkylation