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  • Catalytic epoxidation of a technical mixture of methyl oleate and methyl linoleate in ionic liquids using MoO(O2)2.2QOH (QOH = 8-quinilinol) as catalyst and NaHCO3 as co-catalyst.

Catalytic epoxidation of a technical mixture of methyl oleate and methyl linoleate in ionic liquids using MoO(O2)2.2QOH (QOH = 8-quinilinol) as catalyst and NaHCO3 as co-catalyst.

Molecules (Basel, Switzerland) (2009-08-25)
Shuang-Fei Cai, Li-Sheng Wang, Chuan-Lei Fan
ABSTRACT

The oxo-diperoxo molybdenum(VI) complex MoO(O(2))(2).2QOH (QOH = 8-quinilinol) was prepared and characterized by elemental analysis, IR and UV-Vis spectra. The ionic liquids (ILs) [bmim][BF(4)], [hydemim][BF(4)], and [bmim][PF(6)] were characterized by (1)H-NMR and UV-Vis spectra. The epoxidation of a technical mixture of methyl oleate and methyl linoleate with H(2)O(2), in [bmim][BF(4)], [hydemim][BF(4)] and [bmim][PF(6)], catalyzed by MoO(O(2))(2).2QOH (QOH = 8-quinilinol) and with NaHCO(3) as co-catalyst has been studied for the first time. It was found that high conversions of methyl oleate and methyl linoleate to their respective oxidation products, as well as the total selectivity of their oxidation products to oxirane in [hydemim][BF(4)] were obtained. Also, the IL phases containing the Mo(VI) catalyst can be readily recycled by washing with diethyl ether and drying, and the Mo(VI) catalyst can be reused at least five times.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl oleate, 99%
Sigma-Aldrich
Methyl linoleate, ≥98% (GC)
Supelco
Methyl oleate, analytical standard
Supelco
Methyl linoleate, analytical standard
Sigma-Aldrich
Methyl oleate, technical grade, 70%
Sigma-Aldrich
Methyl elaidate, ≥99% (capillary GC)
Supelco
cis-9-Octadecenoic acid methyl ester, certified reference material, 10 mg/mL in heptane
Supelco
trans-9,12-Octadecadienoic acid methyl ester, certified reference material, 10 mg/mL in heptane
Sigma-Aldrich
Methyl linolelaidate, ≥99% (GC), liquid
Supelco
Methyl elaidate, analytical standard
Supelco
Methyl linolelaidate, analytical standard
Supelco
cis-9,cis-12-Octadecadienoic acid methyl ester, certified reference material, 10 mg/mL in heptane