US 11,718,599 B2
Method for producing cyclic carbonate having unsaturated group, and novel cyclic carbonate
Akiyoshi Yamauchi, Osaka (JP); Kotaro Hayashi, Osaka (JP); Yuuki Suzuki, Osaka (JP); Yoshihiro Yamamoto, Osaka (JP); and Yosuke Kishikawa, Osaka (JP)
Assigned to DAIKIN INDUSTRIES, LTD., Osaka (JP)
Appl. No. 16/754,980
Filed by DAIKIN INDUSTRIES, LTD., Osaka (JP)
PCT Filed Sep. 20, 2018, PCT No. PCT/JP2018/034868
§ 371(c)(1), (2) Date Apr. 9, 2020,
PCT Pub. No. WO2019/073775, PCT Pub. Date Apr. 18, 2019.
Claims priority of application No. 2017-197971 (JP), filed on Oct. 11, 2017; and application No. 2018-040689 (JP), filed on Mar. 7, 2018.
Prior Publication US 2021/0198228 A1, Jul. 1, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 317/40 (2006.01); C07D 317/36 (2006.01)
CPC C07D 317/40 (2013.01) [C07D 317/36 (2013.01)] 11 Claims
 
1. A method for producing a cyclic carbonate represented by the following formula (1a):

OG Complex Work Unit Chemistry
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; Ra has a carbon number of 1 to 10, and Ra is
a group represented by the following formula (C):
—(Rb1)—C≡C-L1  (C)
wherein Rb1 is an alkylene group optionally containing an oxygen atom or a carbon-carbon unsaturated bond between carbon atoms; and L1 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):
—(Rb2)—CL2=CL3L4  (D)
wherein Rb2 is an alkylene group optionally containing an oxygen atom or an unsaturated bond between carbon atoms; L2, L3, and L4 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 L2, L3, and L4 contains a fluorine atom, or
a group represented by the following formula (E′):
(Rb2)-L5a  (E′)
wherein Rb2 is defined as described above; L5a is a group containing an aromatic ring, and L5a contains a fluorine atom,
the method comprising
reacting an unsaturated cyclic carbonate represented by the following formula (A):

OG Complex Work Unit Chemistry
wherein X1 and X2 are defined as described above, and
an alcohol represented by the following formula (B):
Ra—OH  (B)
wherein Ra is defined as described above, or an alkoxide thereof in the presence of a base, or
reacting the unsaturated cyclic carbonate and the alkoxide.