Method of producing epoxy compound and catalyst composition for epoxidation reaction

A catalyst composition, comprising:

• a tungsten compound, a molybdenum compound, or both;
• and
• an onium salt selected from the group consisting of formula (8), (9), (10), (12) and (31):
• wherein
• R20 in formulae (8), (10), (12) and (31) represents a hydrogen atom;
• a halogen atom;
• a cyano group;
• a nitro group;
• an alkyl group having a carbon number of 1 to 25, in which one or more of the carbon atoms may be substituted with a heteroatom;
• a phenyl group;
• a phenoxy group;
• a benzyl group;
• an alkoxycarbonyl group;
• an N-alkylcarbamoyl group or an N-alkylsulfamoyl group;
• R20 in formula (9) represents an alkyl group having a carbon number of 1 to 25;
• each of R21, R22 and R23 independently represents an alkyl group having a carbon number of 1 to 25, in which a part of carbon atoms may be substituted with a heteroatom, or a benzyl group;
• R20, R21, R22 and R23 may combine in the same compound to form a ring;
• k represents an integer of 1 to 4;
• each of R31 and R32 independently represents a divalent aliphatic hydrocarbon group having a carbon number of 1 to 25, in which a part of carbon atoms may be substituted with a heteroatom;
• R33 represents an alkyl group having a carbon number of 1 to 16;
• provided that a plurality of k, R20 or R31 present in the same compound may be the same or different and the total number of carbon atoms contained in the cation moiety in the formulae is 20 or more;
• and
• X− represents a monovalent anion selected from the group consisting of a hydrogen sulfate ion, a monomethyl sulfate ion, a halide ion, a nitrate ion, an acetate ion, a hydrogen carbonate ion, a dihydrogen phosphate ion, a sulfonate ion, a carboxylate ion and a hydroxide ion;
• wherein the catalyst composition catalyzes the epoxidation reaction of hydrogen peroxide with a compound having a carbon-carbon double bond to obtain an epoxy compound.