Method of producing N,N-disubstituted amide and catalyst for producing N,N-disubstituted amide
A method of producing an N,N-disubstituted amide of the present invention is a method of reacting a nitrile with an alcohol in the presence of a catalyst, wherein the nitrile is a compound represented by R 1 CN (R 1 represents an alkyl group having 10 or less carbon atoms or an aryl group having 10 or less carbon atoms), wherein the alcohol is a compound represented by R 2 OH (R 2 represents an alkyl group having 10 or less carbon atoms), wherein the catalyst is a metal salt represented by MXn (M represents a metal cation having an oxidation number of n, X represents a monovalent anion including a substituted sulfonyl group represented by —S(═O) 2 —R 3 (R 3 represents a hydrocarbon group having 10 or less carbon atoms or a group in which some or all of hydrogen atoms in the hydrocarbon group are substituted with fluorine atoms), and n represents an integer of 1 to 4), a substituent bonded to a carbon atom in a carbonyl group of the N,N-disubstituted amide is R 1 , and two substituents bonded to nitrogen atoms in an amide group are both R 2 .
1. A method of producing an N,N-disubstituted amide by reacting a nitrile with an alcohol in the presence of a catalyst,
wherein the nitrile is a compound represented by
R 1 CN
wherein in the formula, R 1 represents an alkyl group having 10 or less carbon atoms or an aryl group having 10 or less carbon atoms,
wherein the alcohol is a compound represented by
R 2 OH
wherein in the formula, R 2 represents an alkyl group having 10 or less carbon atoms,
wherein the catalyst includes a metal salt represented by
MXn
wherein in the formula, M represents a metal cation having an oxidation number of n, X represents a monovalent anion including at least one substituted sulfonyl group represented by —S(═O) 2 —R 3 , wherein in the formula R 3 represents a hydrocarbon group having 10 or less carbon atoms or a group in which some or all of the hydrogen atoms in the hydrocarbon group are substituted with fluorine atoms, and n represents an integer of 1 to 4, and
wherein a substituent bonded to a carbon atom in a carbonyl group of the N,N-disubstituted amide is R 1 , and two substituents bonded to nitrogen atoms in an amide group are both R 2 .
2. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein R 3 is an alkyl group or a perfluoroalkyl group.
3. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the catalyst is a metal methanesulfonate.
4. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the catalyst is a metal trifluoromethanesulfonate.
5. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein X is any one selected from among anions represented by the following Formulae (2) to (9):
6. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein M is any one selected from the group consisting of Zn, Cu, Sn, Al, Sc, and elements classified as lanthanoids.
7. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the catalyst is used in an amount of 0.1 to 3.0 mol % with respect to a molar amount of the nitrile.
8. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the nitrile is acetonitrile.
9. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the alcohol is methanol.
10. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the reaction is caused in an autoclave reactor under a sealed condition.
11. The method of producing an N,N-disubstituted amide according to claim 1 ,
wherein the reaction temperature is lower than 300° C.