Method of producing epoxy compound and catalyst composition for epoxidation reaction
A method of producing an epoxy compound, which comprises reacting hydrogen peroxide with a compound having a carbon-carbon double bond, in the presence of at least one of a tungsten compound and a molybdenum compound; and an onium salt comprising 20 or more carbon atoms and one or more of substituents convertible to a functional group containing an active hydrogen or a salt thereof.
1. 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
R 20 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;
R 20 in formula (9) represents an alkyl group having a carbon number of 1 to 25;
each of R 21 , R 22 and R 23 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;
R 20 , R 21 , R 22 and R 23 may combine in the same compound to form a ring;
k represents an integer of 1 to 4;
each of R 31 and R 32 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;
R 33 represents an alkyl group having a carbon number of 1 to 16;
provided that a plurality of k, R 20 or R 31 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.
2. The catalyst composition according to claim 1 , further comprising a phosphoric acid, a phosphonic acid, or both, which is different from the onium salt.
3. The catalyst composition according to claim 2 , wherein the onium salt is represented by formula (8), formula (9), or formula (10).
4. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (8).
5. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (9).
6. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (9), wherein R 20 is an alkyl group having a carbon number of 1 to 4.
7. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (9), wherein R 20 is an alkyl group having a carbon number of 1 to 4, and each of R 21 and R 22 independently represents an alkyl group having a carbon number of 1 to 8.
8. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (9), wherein R 20 is an alkyl group having a carbon number of 1 to 4, each of R 21 and R 22 independently represents an alkyl group having a carbon number of 1 to 8, and R 31 represents an alkylene group having a carbon number of 1 to 5.
9. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (10).
10. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (12).
11. The catalyst composition according to claim 1 , wherein the onium salt is represented by formula (31).