Fluorinated carbonate derivative production method

Patent metadata

Field	Value
Publication number	US-11167259-B2
Application number	US-201816605635-A
Country	US
Kind code	B2
Filing date	Apr 27, 2018
Priority date	May 16, 2017
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

The objective of the present invention is to provide a method for producing a fluorinated carbonate derivative in a safe and efficient manner. The method for producing a fluorinated carbonate derivative according to the present invention is characterized in comprising irradiating light on a composition containing a C1-4 halogenated hydrocarbon having one or more kinds of halogen atoms selected from the group consisting of a chlorine atom, a bromine atom and an iodine atom, a fluorine-containing compound having a nucleophilic functional group and a base in the presence of oxygen.

First claim

The invention claimed is:

1. A method for producing a fluorinated carbonate derivative, the method comprising
irradiating light on a composition containing a C 1-4 halogenated hydrocarbon having one or more kinds of halogen atoms selected from the group consisting of a chlorine atom, a bromine atom and an iodine atom, a fluorine-containing compound having a nucleophilic functional group and a base in the presence of oxygen,
wherein the fluorine-containing compound is a compound represented by formula (i) and the fluorinated carbonate derivative is a fluorinated carbonate derivative represented by formula (I), or
the fluorine-containing compound is a compound represented by formula (ii) and the fluorinated carbonate derivative is a fluorinated polycarbonate derivative containing a unit represented by formula (II-1) or a fluorinated cyclic carbonate derivative represented by formula (II-2):
R F1 -A-H  (i)

H-A-R F2 -A-H  (ii)

R F1 -A-C(═O)-A-R F1   (I)

[-A-R F2 -A-C(═O)—]  (II-1)

wherein
A is O, S or NH,
R F1 is an unreactive fluorine atom-containing monovalent organic group, and
R F2 is an unreactive fluorine atom-containing divalent organic group.

2. The method according to claim 1 , wherein the fluorine-containing compound is a compound represented by formula (i-1) and the fluorinated carbonate derivative is a fluorinated carbonate derivative represented by formula (I-1), the fluorine-containing compound is a compound represented by formula (i-2) and the fluorinated carbonate derivative is a fluorinated carbonate derivative represented by formula (I-2), or the fluorine-containing compound is a compound represented by formula (i-3) and the fluorinated carbonate derivative is a fluorinated carbonate derivative represented by formula (I-3):
R F11 CH 2 -A-H  (i-1)

(R F12 ) 2 CH-A-H  (i-2)

(R F13 ) 3 C-A-H  (i-3)

R F11 CH 2 -A-C(═O)-A-CH 2 —R F11   (I-1)

(R F12 ) 2 CH-A-C(═O)-A-CH(R F12 ) 2   (I-2)

(R F13 ) 3 C-A-C(═O)-A-C(R F13 ) 3   (I-3)

wherein
A is O, S or NH,
R F11 is a C 1-10 fluoroalkyl group, a C 6-14 fluoroaryl group, a C 4-14 fluoroheteroaryl group or a C 2-24 fluoro(alkylpolyoxyalkylene) group,
two R F12 are independently a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 6-14 aryl group, a C 6-14 fluoroaryl group, a C 4-14 heteroaryl group, a C 4-14 fluoroheteroaryl group, a C 2-24 alkylpolyoxyalkylene group or a C 2-24 fluoro(alkylpolyoxyalkylene) group, and one or two R F12 are a C 1-10 fluoroalkyl group, a C 6-14 fluoroaryl group, a C 4-14 fluoroheteroaryl group or a C 2-24 fluoro(alkylpolyoxyalkylene) group, or two R F12 cooperatively form a C 2-6 fluoroalkylene group or a 1,2-fluoroarylene group, and
three R F13 are independently a C 1-10 alkyl group, a C 1-10 fluoroalkyl group, a C 6-14 aryl group, a C 6-14 fluoroaryl group, a C 4-14 heteroaryl group, a C 4-14 fluoroheteroaryl group, a C2-24 alkylpolyoxyalkylene group or a C 2-24 fluoro(alkylpolyoxyalkylene) group, and one, two or three R F13 are a C 1-10 fluoroalkyl group, a C 6-14 fluoroaryl group, a C 4-14 fluoroheteroaryl group or a C 2-24 fluoro(alkylpolyoxyalkylene) group.

3. The method according to claim 1 , wherein the fluorine-containing compound is a compound represented by formula (ii-1) and the fluorinated carbonate derivative is a fluorinated polycarbonate derivative represented by formula (II-11), or the fluorine-containing compound is a compound represented by formula (ii-2) and the fluorinated carbonate derivative is a fluorinated cyclic carbonate derivative represented by formula (II-21) or a fluorinated linear carbonate derivative represented by formula (II-22):

wherein
A is O, S or NH, and
R F21 is a C 3-10 fluoroalkylene group or a poly(C 1-4 fluoroalkyleneoxy) group.

4. The method according to claim 1 , wherein the C 1-4 halogenated hydrocarbon is a C 1-4 polyhalogenated hydrocarbon.

5. The method according to claim 1 , wherein the C 1-4 halogenated hydrocarbon is chloroform.

6. The method according to claim 1 , wherein the base is one or more bases selected from the group consisting of a heterocyclic aromatic amine, a non-nucleophilic strong base and an inorganic base.

7. The method according to claim 6 , wherein the base comprises a heterocyclic aromatic amine, which is pyridine, picoline or lutidine.

8. The method according to claim 6 , wherein the base comprises a non-nucleophilic strong base, which is 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene or 1,1,3,3-tetramethylguanidine.

9. The method according to claim 6 , wherein the base comprises an inorganic base, which is an alkali metal hydroxide, an alkali metal hydrogen carbonate or an alkali metal carbonate.

10. The method according to claim 1 , wherein a molar ratio of the fluorine-containing compound to the C 1-4 halogenated hydrocarbon ranges from 0.001 to 1.

11. The method according to claim 1 , wherein a molar ratio of the base to the fluorine-containing compound ranges from 1.5 to 10.

12. The method according to claim 1 wherein a wavelength of the light irradiated on the composition is 180 nm or more and 500 nm or less.

Assignees

• Univ Kobe Nat Univ Corp
• Agc Inc

Inventors

• Tsuda Akihiko

Classifications

• B01J2219/0884

  Gas-liquid · CPC title

• C08G64/307

  and phenols · CPC title

• C08G64/0208 Primary

  saturated · CPC title

• C08G64/04

  Aromatic polycarbonates · CPC title

• C07C273/1809

  with formation of the N-C(O)-N moiety · CPC title