Method for producing carbonate compound
View Patent ↗The present invention relates to a production process capable of selectively producing various kinds of carbonate compounds without restraint in high yields without using toxic compounds such as phosgene and crown ethers, without producing corrosive gases such as hydrogen chloride as a by-product, and without necessity of removing the chloroform as a by-product by distillation, and to a method for producing a carbonate compound, containing reacting compound (1) with a compound having an OH group in the presence of a metal salt and 0.2 to 4.0 mol of compound (2) per mol of the metal salt to obtain a carbonate compound, in which m is an integer of 1-10, Q is an alkylene group having 1 to 4 carbon atoms, etc, and R 10 and R 11 are alkyl groups having 1 to 5 carbon atoms, etc.
1. A method for producing a carbonate compound, comprising reacting a compound represented by the following formula (1) with a compound having an OH group in the presence of a metal salt and 0.2 to 4.0 mol of a compound represented by the following formula (2) per mol of the metal salt to obtain a compound having a carbonate bond,
wherein
m is an integer of from 1 to 10,
Q is an alkylene group having 1 to 4 carbon atoms or a group in which one or more hydrogen atoms of the alkylene group are replaced by an alkyl group having 1 to 5 carbon atoms or by an alkyl group having 2 to 5 carbon atoms and having an ethereal oxygen atom between carbon atom-carbon atom, and Q in the case where m is 2 or more may be the same group or a different group, and
R 10 and R 11 are each independently an alkyl group having 1 to 5 carbon atoms,
wherein, during the reaction of the compound represented by the formula (1) with the compound having an OH group, chloroform produced by the reaction is not removed by distillation.
2. The method for producing a carbonate compound according to claim 1 , wherein the metal salt is at least one kind selected from the group consisting of salts of alkali metals and salts of alkaline earth metals.
3. The method for producing a carbonate compound according to claim 1 , wherein the compound represented by the above formula (2) is a compound represented by the following formula (21):
wherein
m is an integer from 2 to 6 and
R 10 and R 11 are each independently an alkyl group having 1 to 5 carbon atoms.
4. The method for producing a carbonate compound according to claim 1 , wherein the compound having a carbonate bond is a compound represented by the following formula (31) or a compound represented by the following formula (32):
wherein
R 1 and R 2 represent each a monovalent aliphatic hydrocarbon group and R 1 and R 2 are not the same group.
5. The method for producing a carbonate compound according to claim 1 , wherein the compound having a carbonate bond is a cyclic carbonate compound represented by the following formula (3a):
wherein
R 3 represents a divalent aliphatic hydrocarbon group.
6. The method for producing a carbonate compound according to claim 1 , wherein the compound having a carbonate bond is a chainlike carbonate compound represented by the following formula (3b):
wherein
R 3 represents a divalent aliphatic hydrocarbon group and n represents an integer of from 1 to 1,000.
7. The method for producing a carbonate compound according to claim 1 , wherein the compound having an OH group is at least one selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, tert-butyl alcohol, 3-oxa-1-butanol, 2,2,2-trifluoroethanol, 2,2,3,3,3-pentafluoropropanol, 2,2,3,3-tetrafluoropropanol, 1-trifluoromethyl-2,2,2-trifluoro-l-ethanol, 2,2,3,4,4,4-hexafluorobutanol, 2,2,3,3,4,4,5,5-octafluoropentanol, 2,2-difluoro-2-(1,1,2,2-tetrafluoro-2-(pentafluoroethoxy)ethoxy)ethanol, 2,2-difluoro-2-tetrafluoro-2-(tetrafluoro-2-(pentafluoroethoxy)ethoxy)ethoxy)ethanol, 2,3,3,3-tetrafluoro-2-(1,1,2,3,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propoxy)-1-propanol, and 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-1-propanol.
8. The method for producing a carbonate compound according to claim 7 , wherein the compound having an OH group is at least one kind selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 2,2,2-trifluoroethanol, 2,2,3,3,3-pentafluoropropanol, 2,2,3,3-tetrafluoropropanol, and 1-trifluoromethyl-2,2,2-trifluoro-1-ethanol.
9. The method for producing a carbonate compound according to claim 1 , wherein the compound having an OH group is at least one kind selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 3-methyl-1,5-pentanediol, 3-oxa-1,5-pentanediol, 1,6-hexanediol, 1,3-propanediol, 1,2-butanediol, and 1,4-butanediol.