Methods for preparing partially fluorinated esters

Patent metadata

Field	Value
Publication number	US-11999690-B2
Application number	US-201917277193-A
Country	US
Kind code	B2
Filing date	Sep 20, 2019
Priority date	Sep 21, 2018
Publication date	Jun 4, 2024
Grant date	Jun 4, 2024

Abstract

A method for preparing a partially fluorinated ester comprising acyl and alkoxy groups wherein the acyl group comprises a branched or linear fluorine containing C 3 -C 8 group with one of the structures: (Formulae (I), (II)) wherein X and Y are independently selected from: —H, —CH 3 , —F, —Cl, —CH 2 F, —CF 3 —OCF 3 , —OCH 2 CF 3 , OCH 2 CF 2 CHF 2 and —CH 2 CF 3 (wherein both X and Y cannot be H) comprising reacting an unsaturated halocarbon: (Formula (III)) wherein A and B are independently selected from the group comprising —H, —CH 3 , —F, —Cl, —CH 2 F, —CF 3 , —OCF 3 , —OCH 2 CF 3 , OCH 2 CF 2 CHF 2 and —CH 2 CF 3 (wherein both A and B cannot be H) with carbon monoxide and an alcohol, in the presence of a catalyst methods.

First claim

The invention claimed is:

1. A method for preparing a partially fluorinated ester comprising acyl and alkoxy groups wherein the acyl group comprises a branched or linear fluorine containing C 4 -C 8 group with one of the structures:

wherein X and Y are independently selected from:
H, —CH 3 , —F, —Cl, —CH 2 F, —CF 3 , —OCF 3 , —OCH 2 CF 3 , OCH 2 CF 2 CHF 2 and —CH 2 CF 3 , wherein both X and Y cannot be H, comprising (wherein both X and Y cannot be H)
comprising reacting an unsaturated halocarbon:

wherein A and B are independently selected from the group comprising —H, —CH 3 , —F, —Cl, —CH 2 F, —CF 3 , —OCF 3 , —OCH 2 CF 3 , OCH 2 CF 2 CHF 2 and —CH 2 CF 3 , wherein both X and Y cannot be H, with with carbon monoxide and an alcohol, in the presence of a catalyst.

2. A method according to claim 1 , where the acyl group has 3 to 7 carbon atoms.

3. A method according to claim 1 , wherein the acyl group comprises CF 3 —C 2 H 3 FCO, CF 3 CH 2 CH(F)CO, CF 3 CH(CH 2 F)CO, CF 3 CF(CH 3 )CO, CF 3 —C 3 H 3 F 3 CO, or CF 3 CH 2 CH(CF 3 )CO.

4. A method according to claim 1 , comprising reacting 2,3,3,3-Tetrafluoropropene (1234yf) with carbon monoxide and an alcohol of formula ROH to form CF 3 CF(CH 3 )CO 2 R and/or CF 3 CHFCH 2 CO 2 R; or reacting 2-chloro-3,3,3-trifluoropropene (1233xf) with carbon monoxide and an alcohol to form CF 3 CCl(CH 3 )CO 2 R and/or CF 3 CHClCH 2 CO 2 R.

5. A method according to claim 1 , comprising reacting 1,3,3,3-Tetrafluoropropene (1234ze) with carbon monoxide and an alcohol of formula ROH to form to form CF 3 CH(CH 2 F)CO 2 R and/or CF 3 CH 2 CHFCO 2 R.

6. A method according to claim 1 , comprising reacting 1,1,1,4,4,4-hexafluoro-2-butene (1336mzz) with carbon monoxide and an alcohol of formula ROH to form CF 3 CH 2 CH(CF 3 )CO 2 R.

7. A method according to claim 1 , wherein the alkoxy group is derived from a branched or linear monohydric alcohol with the formula HOC n H 2n+1−x F x , wherein n is from 1 to 10 and x has a value from 0 to 2n+1.

8. A method according to claim 1 , wherein the catalyst comprises a group 8-12 metallic compound, and comprising a halogen ligand and a phosphorous-containing ligand or comprising a carbonyl ligand.

9. A method according to claim 8 , wherein the group 8-12 metallic compound is selected from the group consisting of iron, ruthenium, osmium, cobalt rhodium, iridium, nickel, palladium, platinum, copper, silver, gold, zinc, cadmium, and mercury.

10. A method according to claim 8 , wherein when the catalyst comprises the halogen ligand and the phosphorous-containing ligand, the halogen ligand is selected from the group consisting of fluorine, chlorine, bromine and iodine, and the phosphorous-containing ligand is selected from the group consisting of PH 3 and PPh 3 .

11. A method according to claim 8 , wherein when the catalyst comprises the carbonyl ligand, the catalyst comprises another ligand selected from the group consisting of halogen, alkyl, and phosphorous-containing compounds.

Assignees

• Mexichem Fluor Sa De Cv

Inventors

• Sharratt Andrew P
• Mccarthy John Charles

Classifications

• H01M2300/0034

  Fluorinated solvents · CPC title

• H01M10/0569

  characterised by the solvents · CPC title

• C10M2211/0445

  used as base material · CPC title

• C10M105/54

  containing carbon, hydrogen, halogen and oxygen · CPC title

• C09K5/08

  Materials not undergoing a change of physical state when used (C09K5/16, C09K5/20 take precedence) · CPC title