Method for producing fluorine-containing olefin
A production method of producing a fluorine-containing olefin by allowing a first olefin represented by the following Formula (1) and a second olefin to react with each other in the presence of a ruthenium compound represented by the following Formula (X) is provided.
1 . A production method of producing a fluorine-containing olefin comprising:
allowing a first olefin represented by the following Formula (1) and a second olefin different from Formula (1) of the first olefin to react with each other in the presence of a ruthenium compound represented by the following Formula (X):
wherein, in Formula (X),
A represents an atom group necessary for forming a 6- or 7-membered nitrogen-containing heterocyclic ring comprising two nitrogen atoms, an aromatic or aliphatic ring may be condensed to the nitrogen-containing heterocyclic ring, and A and the aromatic or aliphatic ring condensed to the nitrogen-containing heterocyclic ring may comprise a substituent,
each of R 1 and R 2 independently represents an alkyl group, an aryl group, or an aralkyl group,
each of Y 1 and Y 2 independently represents an anionic ligand,
L′ represents a neutral electron-donating ligand,
p represents 0 or 1, and
each of Z 1 and Z 2 independently represents a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom, Z 1 and Z 2 may be bonded to each other to form a ring, and either or both of Z 1 and Z 2 , and L 1 may be chemically bonded to each other,
wherein, in Formula (1), each of A 1 , A 2 , and A 3 independently represents a hydrogen atom, a fluorine atom, a chlorine atom, or a fluorine-containing alkyl group having a carbon number of from 1 to 10.
2 . The production method according to claim 1 , wherein the second olefin is represented by the following Formula (2):
wherein, in Formula (2),
at least one of A 4 to A 7 represents a functional group AA comprising an oxygen atom, a nitrogen atom, a sulfur atom, or a phosphorus atom at a linkage position to vinyl carbon, each of A 4 to A 7 , other than the functional group AA, independently represents a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom, and A 4 and A 5 , A 4 and A 6 , A 5 and A 7 , or A 6 and A 7 may be bonded to each other to form a ring, and
in a case in which one of A 4 or A 5 is a halogen atom, another one of A 4 or A 5 represents a hydrogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom, and in a case in which one of A 6 or A 7 is a halogen atom, another one of A 6 or A 7 represents a hydrogen atom, a monovalent hydrocarbon group having a carbon number of from 1 to 20, or a monovalent hydrocarbon group having a carbon number of from 1 to 20 and comprising one or more atoms selected from the group consisting of a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, and a silicon atom.
3 . The production method according to claim 2 , wherein, in Formula (2), the functional group AA is an alkoxy group having a carbon number of from 1 to 20 or an aryloxy group having a carbon number of from 6 to 20.
4 . The production method according to claim 1 , wherein, in Formula (1), at least two of A 1 , A 2 , or A 3 are fluorine atoms.
5 . The production method according to claim 1 , wherein the second olefin is a monosubstituted olefin or a 1,2-disubstituted olefin.
6 . The production method according to claim 1 , wherein an amount of the ruthenium compound used is from 0.001% by mol to 1.0% by mol with respect to a substance amount of the second olefin.
7 . The production method according to claim 1 , wherein, in Formula (X), each of R 1 and R 2 is independently 2,4,6-trimethylphenyl group, 2,6-diisopropylphenyl group, o-tolyl group, 3,5-di-tert-butylphenyl group, 2,6-dimethyl-4-methoxyphenyl group, or 2,6-difluorophenyl group.
8 . The production method according to claim 1 , wherein A is an atom group that forms a 6-membered nitrogen-containing heterocyclic ring.
9 . The production method according to claim 1 , wherein A is an atom group that forms a 7-membered nitrogen-containing heterocyclic ring.
10 . The production method according to claim 1 , wherein the first olefin and the second olefin react with each other under an olefin back pressure of 1 to 2 atm.
11 . The production method according to claim 1 , wherein the first olefin and the second olefin react with each other in the presence of the ruthenium compound to form the fluorine-containing olefin with a reaction conversion rate of 19.1 to 71.6%.
12 . The production method according to claim 1 , wherein the first olefin and the second olefin react with each other in the presence of the ruthenium compound to form the fluorine-containing olefin with a reaction conversion rate of 58.8 to 98.8%.
13 . The production method according to claim 1 , wherein the first olefin and the second olefin react with each other in the presence of the ruthenium compound to form the fluorine-containing olefin with a selective rate of 3.05 to 10.8.
14 . The production method according to claim 1 , wherein the first olefin and the second olefin react with each other in the presence of the ruthenium compound to form the fluorine-containing olefin with a selective rate of 0.3 to 17.7.
15 . The production method according to claim 1 , wherein the functional group AA is selected from the group consisting of an alkoxy group, an aryloxy group, an acetoxy group, an amino group, an alkythio group, an arylthio group, a dialkyphosphino group and a diarylphosphino group.