Method for producing cyclic carbonate having unsaturated group, and novel cyclic carbonate

Patent metadata

Field	Value
Publication number	US-11718599-B2
Application number	US-201816754980-A
Country	US
Kind code	B2
Filing date	Sep 20, 2018
Priority date	Oct 11, 2017
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

A method for producing a cyclic carbonate represented by the following formula (1):wherein X1 and X2 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, or a monovalent organic group; and R is an organic group containing one or more carbon-carbon unsaturated bonds. The method includes reacting an unsaturated cyclic carbonate represented by the following formula (A):wherein X1 and X2 are defined as described above, and an alcohol represented by the formula (B): R—OH, wherein R is defined as described above, or an alkoxide thereof in the presence of a base, or reacting the unsaturated cyclic carbonate and the alkoxide. Also disclosed is a method for producing a cyclic carbonate.

First claim

The invention claimed is:

1. A method for producing a cyclic carbonate represented by the following formula (1a):

wherein X 1 and X 2 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, or a monovalent organic group; R a has a carbon number of 1 to 10, and R a is
a group represented by the following formula (C):
—(R b1 )—C≡C-L 1   (C)

wherein R b1 is an alkylene group optionally containing an oxygen atom or a carbon-carbon unsaturated bond between carbon atoms; and L 1 is a hydrogen atom, a fluorine atom, a C1-C7 silyl or aryl group optionally containing a fluorine atom, or a C1-C7 alkyl group optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom;
a group represented by the following formula (D):
—(R b2 )—CL 2 =CL 3 L 4   (D)

wherein R b2 is an alkylene group optionally containing an oxygen atom or an unsaturated bond between carbon atoms; L 2 , L 3 , and L 4 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, a C1-C8 silyl group optionally containing a fluorine atom, or a C1-C8 alkyl or aryl group optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom; at least one selected from L 2 , L 3 , and L 4 contains a fluorine atom, or
a group represented by the following formula (E′):
(R b2 )-L 5a   (E′)

wherein R b2 is defined as described above; L 5a is a group containing an aromatic ring, and L 5a contains a fluorine atom,
the method comprising
reacting an unsaturated cyclic carbonate represented by the following formula (A):

wherein X 1 and X 2 are defined as described above, and
an alcohol represented by the following formula (B):
R a —OH  (B)

wherein R a is defined as described above, or an alkoxide thereof in the presence of a base, or
reacting the unsaturated cyclic carbonate and the alkoxide.

2. The method for producing a cyclic carbonate according to claim 1 ,
wherein X 1 and X 2 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, or an alkyl, aryl, alkoxyalkyl, or aryloxyalkyl group optionally containing a fluorine atom.

3. The method for producing a cyclic carbonate according to claim 1 ,
wherein R a is a C1-C10 organic group containing one or more carbon-carbon unsaturated bonds and optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom.

4. The method for producing a cyclic carbonate according to claim 1 ,
wherein R a is a C1-C10 organic group containing a divalent or higher heteroatom and one or more carbon-carbon unsaturated bonds.

5. The method for producing a cyclic carbonate according to claim 4 ,
wherein the divalent or higher heteroatom is an oxygen atom or a silicon atom.

6. The method for producing a cyclic carbonate according to claim 1 ,
wherein the base includes at least one selected from the group consisting of a hydride of an alkali metal or an alkaline earth metal, a hydroxide of an alkali metal or an alkaline earth metal, a carbonate compound of an alkali metal or an alkaline earth metal, a hydrogencarbonate compound of an alkali metal, an alkoxide of an alkali metal or an alkaline earth metal, an amide of an alkali metal or an alkaline earth metal, guanidine, and an amine.

7. A cyclic carbonate represented by the following formula (1a):

wherein X 1 and X 2 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, or a monovalent organic group;
R a has a carbon number of 1 to 10, and R a is
a group represented by the following formula (C):
—(R b1 )—C≡C-L 1   (C)

wherein R b1 is an alkylene group optionally containing an oxygen atom or a carbon-carbon unsaturated bond between carbon atoms; and L 1 is a hydrogen atom, a fluorine atom, a C1-C7 silyl or aryl group optionally containing a fluorine atom, or a C1-C7 alkyl group optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom;
a group represented by the following formula (D):
—(R b2 )—CL 2 =CL 3 L 4   (D)

wherein R b2 is an alkylene group optionally containing an oxygen atom or an unsaturated bond between carbon atoms; L 2 , L 3 , and L 4 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, a C1-C8 silyl group optionally containing a fluorine atom, or a C1-C8 alkyl or aryl group optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom; at least one selected from L 2 , L 3 , and L 4 contains a fluorine atom, or
a group represented by the following formula (E′):
—(R b2 )-L 5a   (E′)

wherein R b2 is defined as described above; L 5a is a group containing an aromatic ring, and L 5a contains a fluorine atom.

8. The cyclic carbonate according to claim 7 ,
wherein X 1 and X 2 are the same as or different from each other, and are each a hydrogen atom, a fluorine atom, or an alkyl, aryl, alkoxyalkyl, or aryloxyalkyl group optionally containing a fluorine atom.

9. The cyclic carbonate according to claim 7 ,
wherein R a is a C1-C10 organic group optionally containing one or both selected from a divalent or higher heteroatom and a fluorine atom.

10. The cyclic carbonate according to claim 7 ,
wherein R a is a C10 or lower organic group containing a divalent or higher heteroatom and one or more carbon-carbon unsaturated bonds.

11. The cyclic carbonate according to claim 10 , wherein the divalent or higher heteroatom is an oxygen atom or a silicon atom.

Assignees

• Daikin Ind Ltd

Inventors

• Yamauchi Akiyoshi
• Hayashi Kotaro
• Suzuki Yuuki
• Yamamoto Yoshihiro
• Kishikawa Yosuke

Classifications

• C07D317/40 Primary

  Vinylene carbonate; Substituted vinylene carbonates · CPC title

• C07D317/36 Primary

  Alkylene carbonates; Substituted alkylene carbonates · CPC title