Process for producing fluorinated electrolyte solvent

Patent metadata

Field	Value
Publication number	US-2018079708-A1
Application number	US-201615270256-A
Country	US
Kind code	A1
Filing date	Sep 20, 2016
Priority date	Sep 20, 2016
Publication date	Mar 22, 2018
Grant date	—

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

1 . A method for producing halogenated carbonates, the method comprising: reacting a fluorinated hydroxyl moiety 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.

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 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.

4 . The method as recited in claim 1 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.

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

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

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

8 . The method as recited in claim 1 wherein the halogenated carbonate is a fluorinated carbonate selected from the group consisting of bis(trifluoroethyl) carbonate, trifluoropropylene carbonate, bis(pentafluoropropyl) carbonate, 4,5-bis(trifluoromethyl)-1,3-dioxolan-2-one, and combinations thereof.

9 . 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.

10 . (canceled)

11 . The method as recited in claim 1 wherein the halogenated moiety is a fluorinated compound selected from the group consisting of trifluoroethanol, pentafluoro-1-propanol, and hexafluoroisopropanol.

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

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

14 . A method for producing fluorinated carbonates, the method comprising reacting a liquid halogenated hydroxyl moiety with a solid carbonyl source in an ether 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.

15 . The method as recited in claim 14 wherein the fluorinated carbonate is represented by Formula I:

wherein R1 and R2 are individually an alkyl or C n H x F y group, an H, F, and combinations thereof;
wherein each x is individually from 0 to 2n;
wherein each y is individually from 1 to 2n+1; and
wherein each n is individually an integer from 1 to 5.

16 . The method as recited in claim 14 wherein the fluorinated carbonate is represented by Formula II:

wherein R2 is a C n H x F y group, an F, F 2 , F 3 , and combinations thereof;
wherein each x is individually from 0 to 2n;
wherein each y is individually from 1 to 2n+1; and
wherein each n is individually an integer from 1 to 5.

17 . The method as recited in claim 16 wherein the halogenated hydroxyl moiety contains fluorine, chlorine, and combinations thereof.

18 . The method as recited in claim 16 wherein the halogenated hydroxyl moiety is a fluorine containing compound selected from the group consisting of 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.

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

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

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

22 . 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.

23 . The method as recited in claim 22 wherein the halogenated 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