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.
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.
Cai
Shuang-Fei
SF
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, China.
Wang
Li-Sheng
LS
Fan
Chuan-Lei
CL
D002384:Catalysis; D006861:Hydrogen Peroxide / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D008041:Linoleic Acids / Q000737:chemistry*; D008982:Molybdenum / Q000737:chemistry*; D009829:Oleic Acids / Q000737:chemistry*; D010084:Oxidation-Reduction; D010087:Oxides / Q000737:chemistry*; D015125:Oxyquinoline / Q000737:chemistry*; D017693:Sodium Bicarbonate / Q000737:chemistry*
D052578:Ionic Liquids; D008041:Linoleic Acids; D009829:Oleic Acids; D010087:Oxides; C005575:methyl linoleate; C005576:methyl oleate; D015125:Oxyquinoline; D008982:Molybdenum; D017693:Sodium Bicarbonate; D006861:Hydrogen Peroxide
Chem Commun (Camb). 2003 Aug 21;(16):1977-86
12934880
J Org Chem. 2002 Nov 1;67(22):7716-23
12398494
J Am Chem Soc. 2002 Oct 9;124(40):11946-54
12358539
Chemistry. 2000 Jul 3;6(13):2377-81
10939740
Lipids. 1998 Jun;33(6):633-7
9655380