Fluorinated carbonates comprising double bond-containing groups, methods for their manufacture and uses thereof

Patent metadata

Field	Value
Publication number	US-2016145190-A1
Application number	US-201414903357-A
Country	US
Kind code	A1
Filing date	Jul 9, 2014
Priority date	Jul 9, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

Fluorinated carbonates comprising double-bond containing groups were prepared and their use as solvent additives or solvents in lithium ion batteries, lithium air batteries, lithium sulphur batteries and supercapacitors is described. Preferred compounds contain at least one alkenyl or at least one (hetero)aryl group.

First claim

1 . A compound of general formula (I),
R 1 R 2 CF—O—C(O)—O—R 3
wherein R 1 and R 2 are independently H, F, alkyl, cycloalkyl, alkylene-aryl, or alkylene-heteroaryl; and wherein R 3 is a double bond-containing group.

2 . The compound according to claim 1 wherein R 3 is an alkenyl.

3 . The compound according to claim 1 wherein R 3 is an aryl group or an alkylene-aryl group.

4 . The compound according to claim 1 wherein R 2 is H.

5 . The compound according to claim 1 wherein R 1 is H or an alkyl group.

6 . The compound according to claim 1 wherein R1 is methyl, R2 is H, R3 is allyl and the compound is (1-fluoroethyl)allyl carbonate.

7 . The compound according to claim 1 wherein R1 is methyl, R2 is H, R3 is phenyl and the compound is (1-fluoroethyl)phenyl carbonate.

8 . A method for the manufacture of a compound of general formula (I),
R 1 R 2 CF—O—C(O)—O—R 3
the method comprising a step of reacting a fluoroformate of general formula (II),
R 1 R 2 CF—O—C(O)F

with an alcohol of general formula (III), R 3 —OH; wherein R 1 is H, F, alkyl, cycloalkyl, alkylene-aryl, or alkylene-heteroaryl; wherein R 2 is H, and wherein R 3 is a double bond-containing group.

9 . A method for the manufacture of a compound of general formula (I),
R 1 R 2 CF—O—C(O)—O—R 3
the method comprising a first step of reacting phosgene or a phosgene analogue with a compound of the general formula (IV) R 1 R 2 CF—OH to form an intermediate of the general formula (V)
R 1 R 2 CF—O—C(O)X

and a second step of reacting the intermediate of the general formula (V) with a compound of the general formula (VI) R 3 —OH; or comprising a first step of reacting phosgene or a phosgene analogue with a compound of the general formula (VI) R 3 —OH to form an intermediate of the general formula (VII)
R 3 —O—C(O)X

and a second step of reacting the intermediate of the general formula (VII) with a compound of the general formula (VIII) R 1 R 2 CF—OH; wherein R 1 and R 2 are independently H, F, alkyl, cycloalkyl, alkylene-aryl, or alkylene-heteroaryl; wherein R 3 is a double bond-containing group; and wherein X − is a leaving group.

10 . (canceled)

11 . (canceled)

12 . A solvent composition for lithium ion batteries, lithium air batteries, lithium sulfur batteries, supercapacitors or hybrid supercapacitors, comprising at least one solvent useful for lithium ion batteries and at least one compound according to claim 1 .

13 . An electrolyte composition for lithium ion batteries, lithium air batteries, lithium sulfur batteries, supercapacitors or hybrid supercapacitors, comprising at least one compound according to claim 1 , at least one solvent useful for lithium ion batteries or supercapacitors and at least one electrolyte salt.

14 . A lithium ion battery, a lithium air battery, a lithium sulfur battery, a supercapacitor or a hybrid supercapacitor containing at least one compound according to claim 1 .

15 . The electrolyte composition according to claim 13 , wherein the concentration of the compound of general formula (I) is from 1 to 15 wt %, relative to the total weight of the electrolyte composition.

16 . The compound according to claim 2 wherein R 3 is allyl.

17 . The compound according to claim 3 wherein R 3 is phenyl or benzyl.

18 . The compound according to claim 17 wherein R 3 is phenyl.

19 . The compound according to claim 5 wherein R 1 is methyl.

20 . The method according to claim 9 , wherein X − is chloride or fluoride.

21 . The electrolyte composition according to claim 15 , wherein the concentration of the compound of general formula (I) is from 3 to 10 wt %, relative to the total weight of the electrolyte composition.

22 . The electrolyte composition according to claim 15 , wherein the concentration of the compound of general formula (I) is between 4 and 6 wt %, relative to the total weight of the electrolyte composition.

Assignees

• Solvay

Inventors

• Bomkamp Martin
• Kim Hag-Soo

Classifications

• Y02E60/10

  Energy storage using batteries · CPC title

• C07C68/02

  from phosgene or haloformates · CPC title

• H01M10/052

  Li-accumulators · CPC title

• C07C69/96 Primary

  Esters of carbonic or haloformic acids · CPC title

• H01M12/02

  Details (of electrodes H01M4/00; of non-active parts H01M50/00) · CPC title