Process for producing fluorinated electrolyte solvent

Patent metadata

Field	Value
Publication number	US-10294189-B2
Application number	US-201615270256-A
Country	US
Kind code	B2
Filing date	Sep 20, 2016
Priority date	Sep 20, 2016
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

The invention provides a method for producing halogenated carbonates, the method comprising reacting a halogenated alcohol or diol with a solid source of carbonyl moiety as a base in an ether.

First claim

The embodiment of the invention in which an exclusive property or privilege is claimed is defined as follows:

1. A method for producing a halogenated carbonate selected from the group consisting of bis(2,2,2-trifluoroethyl) carbonate, trifluoropropylene carbonate, bis(pentafluoropropyl) carbonate, 4,5-bis(trifluoromethyl)-1,3-dioxolan-2-one, and combinations thereof, the method comprising:
reacting a fluorinated hydroxyl moiety selected from the group consisting of trifluoroethanol, 1,1,3,3,3-hexafluoro-2-propanol, 2,2,3,3,3pentafluoropropanol, 2,2,3,3,4,4,4-heptafluoro-1-butanol, 2,2-difluoroethanol, 2,2,3,3-tetrafluoro-1,4-butanediol, and combinations thereof, with a solid carbonyl source in an ether to create a reaction mixture, wherein the reaction mixture of the fluorinated hydroxyl moiety and the solid carbonyl source comprises a heterogeneous reaction liquor, and wherein no chlorinated compounds are utilized;
wherein the ether is a below 75 C boiling point compound selected from the group consisting of methyl tert-butyl ether, diethyl ether, tetrahydrofuran, and combinations thereof;
wherein the solid carbonyl source is a nitrogen-containing compound selected from the group consisting of carbonyldiimidazole, disuccinimidyl carbonate, 1,1′-Carbonyl-di(1, 2,4-triazole), and combinations thereof.

2. The method as recited in claim 1 wherein a boiling point of the ether determines a boiling point of the reaction liquor.

3. The method as recited in claim 1 wherein the method occurs in ambient pressure.

4. The method as recited in claim 1 wherein halogenated carbonates are produced in about 1 to about 4 hours.

5. The method as recited in claim 1 wherein the halogenated carbonates are produced at temperatures between about 30° C. and about 70° C.

6. The method as recited in claim 1 wherein purity of the halogenated carbonates is greater than about 99.5 percent after a single distillation step.

7. The method as recited in claim 1 wherein the product is purified without an aqueous extraction step.

8. The method as recited in claim 1 wherein reaction byproducts are isolated with a single filtration step.

9. A method for producing fluorinated carbonates having the following Formula I

or Formula II

wherein R 1 and R 2 are a fluorine-containing CnHxFy group and wherein each x is individually from 0 to 2n, each y is individually from 1 to 2n+1, and each n is individually an integer from 1 to 5, the method comprising reacting a liquid fluorinated hydroxyl moiety of five carbons or less with a nitrogen containing solid carbonyl source in an ether having a boiling point below 75° C. to create a reaction mixture, wherein the reaction mixture of the halogenated hydroxyl moiety and the solid carbonyl source comprises a heterogeneous reaction liquor, and wherein no chlorinated compounds are utilized;
wherein the fluorinated hydroxyl moiety is a fluorinated hydroxyl compound selected from the group consisting of trifluoroethanol, 1,1,3,3,3-hexafluoro-2-propanol, 2,2,3,3,3-pentafluoropropanol, 2,2,3,3,4,4,4-heptafluoro-1-butanol, 2,2-difluoroethanol, 2,2,3,3-tetrafluoro-1,4-butanediol and combinations thereof;
and wherein the nitrogen containing solid carbonyl source is a nitrogen containing solid carbonyl source selected from the group consisting of carbonyldiimidazole, disuccinimidyl carbonate, 1,1′-Carbonyl-di-(1,2,4-triazole), and combinations thereof.

10. The method as recited in claim 1 wherein the ether is methyl tert-butyl ether.

11. The method as recited in claim 1 wherein the solid carbonyl source is carbonyldiimidazole.

12. The method as recited in claim 1 wherein the halogenated carbonate is bis(2,2,2-trifluoroethyl) carbonate.

13. A method for producing fluorinated carbonates, the method comprising: reacting trifluoroethanol with carbonyldiimidazole in methyl tert-butyl ether to create a reaction mixture, wherein the reaction mixture comprises a heterogeneous reaction liquor.

14. The method as recited in claim 13 wherein the fluorinated carbonate is bis-(2,2,2-trifluoroethyl) carbonate.

Assignees

• Dzwiniel Trevor L
• Pupek Krzysztof
• Krumdick Gregory K
• Uchicago Argonne Llc

Inventors

• Dzwiniel Trevor L
• Pupek Krzysztof
• Krumdick Gregory K

Classifications

• C07C67/20 Primary

  from amides or lactams · CPC title

• C07D317/34 Primary

  Oxygen atoms · CPC title

• C07C68/00

  Preparation of esters of carbonic or haloformic acids · CPC title

• C07D317/36

  Alkylene carbonates; Substituted alkylene carbonates · CPC title