Process for producing hydrofluoroethers

Patent metadata

Field	Value
Publication number	US-2025388526-A1
Application number	US-202318879654-A
Country	US
Kind code	A1
Filing date	Jun 22, 2023
Priority date	Jun 29, 2022
Publication date	Dec 25, 2025
Grant date	—

Abstract

A process for making hydrofluoroethers, the process comprising: •A) providing a mixture comprising one more polar aprotic organic solvents having a boiling point measured at 1 atm (1.01 bar) of from 60° C. to 170° C. and one or more chemical compounds carrying at least one —OH group which is part of an alcohol or of a phenol group, and •B): reacting said one or more chemical compounds carrying at least one —OH group with one or more fluorinated olefin in the presence of a basic catalyst thus providing a reacted mixture comprising one or more hydrofluoroethers.

First claim

1 . A process for making hydrofluoroethers, the process comprising:
A) providing a mixture comprising one or more polar aprotic organic solvents having a boiling point measured at 1 atm of from 60° C. to 170° C. and one or more chemical compounds carrying at least one —OH group which is part of an alcohol or of a phenol group, and B) reacting said one or more chemical compounds carrying at least one —OH group with one or more fluorinated olefins in the presence of a basic catalyst thus providing a reacted mixture comprising one or more hydrofluoroethers.

2 . The process according to claim 1 wherein said fluorinated olefin is a fully halogenated olefin.

3 . The process according to claim 2 wherein said fluorinated olefin is selected from the group consisting of perfluoromethyl vinyl ether, perfluoroethyl vinyl ether, perfluoropropyl vinyl ether, tetrafluoroethylene, hexafluoropropylene, and chlorotrifluoroethylene.

4 . The process according to claim 3 wherein said fluorinated olefin is tetrafluoroethylene.

5 . The process according to claim 1 wherein said one or more chemical compounds carrying at least one —OH group are polyfunctional alcohols.

6 . The process according to claim 5 wherein said one or more chemical compounds carrying at least one —OH group is selected from the group consisting of ethylene glycol, di-ethylene glycol, tri-ethylene glycol, propylene glycol, di-propylene glycol, tri-propylene glycol and mixtures thereof.

7 . The process according to claim 5 wherein said one or more chemical compounds carrying at least one —OH group is ethylene glycol.

8 . The process according to claim 1 wherein said one or more chemical compounds carrying at least one —OH group are phenols.

9 . The process according to claim 8 wherein said one or more chemical compounds carrying at least one —OH group is selected from the group consisting of phenol, cresol, methoxyphenol, fluorophenol and chlorophenol.

10 . The process according to claim 1 wherein said one or more polar aprotic organic solvent is acetonitrile,

11 . The process according to claim 1 , comprising an additional step C wherein said hydrofluoroethers are directly extracted from said reacted mixture.

12 . The process according to claim 1 wherein said process further comprises the steps of
D) evaporating completely said reacted mixture and re-condensing it in liquid form as a purified reacted mixture, and
E) separating said hydrofluoroethers in purified form from said purified reacted mixture via distillation.

13 . The process according to claim 1 wherein said process further comprises the steps of
F) mixing said reacted mixture with water, agitating the mixture thereby extracting water soluble impurities from said reacted mixture, and separating the purified reacted mixture as a water immiscible phase, and
G) separating hydrofluoroethers in purified form from said purified reacted mixture via distillation.

14 . The process of claim 11 , wherein the direct extraction is via distillation.

Assignees

• Solvay Specialty Polymers It

Inventors

• Antenucci Emanuela
• Bragante Letanzio
• Gregori Manuel
• Millefanti Stefano

Classifications

• C07C41/42

  by distillation · CPC title

• C07C41/14 Primary

  by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification · CPC title

• C07C43/225

  containing halogen · CPC title

• C07C43/126

  having more than one ether bond · CPC title

• C07C41/38

  by liquid-liquid treatment · CPC title