Method for preparing a tetrafluoro-1,2-epoxypropane

Patent metadata

Field	Value
Publication number	US-11718597-B2
Application number	US-202217829598-A
Country	US
Kind code	B2
Filing date	Jun 1, 2022
Priority date	Apr 27, 2017
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

A method for preparing a tetrafluoro-1,2-epoxypropane comprising reacting a 3-acetoxy-2-bromo-tetrafluoropropane with an alkaline or alkaline earth metal hydroxide solution to provide a tetrafluoro-1,2-epoxypropane, and partially fluorinated polyethers of formula [OCRR1CR2R3]n wherein n is from 5 to 100, R is F or H, R1 is CF3, R2 is F or H and R3 is H.

First claim

The invention claimed is:

1. A method for preparing a tetrafluoro-1,2-epoxypropane comprising reacting a 3-acetoxy-2-bromo-tetrafluoropropane with an alkaline or alkaline earth metal hydroxide solution to provide a tetrafluoro-1,2-epoxypropane.

2. The method according to claim 1 , wherein the 3-acetoxy-2-bromo-tetrafluoropropane is 3-acetoxy-2-bromo-1,1,1,2-tetrafluoropropene or 3-acetoxy-2-bromo-1,1,1,2-tetrafluoropropene, which is reacted with sodium or potassium hydroxide to form 2,3,3,3-tetrafluoro-1,2-epoxypropane or 1,3,3,3-tetrafluoro-1,2-epoxypropane.

3. The method of claim 1 , wherein the alkaline metal hydroxide is sodium hydroxide.

4. The method of claim 1 , wherein the alkaline metal hydroxide is potassium hydroxide.

5. A method for preparing a partially fluorinated polyether, comprising polymerising 2,3,3,3-tetrafluoro-1,2-epoxypropane or 1,3,3,3-tetrafluoro-1,2-epoxypropane to provide a partially fluorinated polyether of formula [OCRR 1 CR 2 R 3 ] n , wherein R is H, R 1 is CF 3 , R 2 is H and R 3 is F or R is F, R 1 is CF 3 , R 2 is H and R 3 is H, wherein n is from 5 to 100.

6. The method according to claim 5 , further comprising reacting a 2-bromo-tetrafluoropropan-3-ol with an alkaline or alkaline earth metal hydroxide solution to provide 2,3,3,3-tetrafluoro-1,2-epoxypropane or 1,3,3,3-tetrafluoro-1,2-epoxypropane.

7. The method of claim 6 , further comprising reacting 3-acetoxy-2-bromo-1,1,1,2-tetrafluoropropene or 3-acetoxy-2-bromo-1,1,1,2-tetrafluoropropene with sulphuric acid in an aqueous solution to provide 2-bromo-1,1,1,2-tetrafluoropropan-3-ol or 2-bromo-1,1,1,3-tetrafluoropropan-3-ol.

8. The method according to claim 6 , wherein the reaction to form 2,3,3,3-tetrafluoro-1,2-epoxypropane or 1,3,3,3-tetrafluoro-1,2-epoxypropane and the reaction to form the partially fluorinated polyether take place in the same reaction vessel.

9. The method according to claim 5 , wherein the polymerising is initiated using a cationic initiator, an anionic initiator or an organometallic based initiator.

10. The method according to claim 9 , wherein the initiator is an alkali metal tert-butoxide, sodium or potassium hydroxide, sulphuric acid, metal chloride or metal fluoride.

11. The method according to claim 10 , wherein the metal fluoride is cesium fluoride.

12. The method according to claim 9 , wherein the initiator is an organozinc or organoaluminium compound.

13. The method according to claim 12 , wherein the initiator is selected from the group consisting of Zn(C 2 H 5 ) 2 , (C 2 H 5 ZnOCH 3 ) 4 , Zn(OCH 3 ) 2 (C 2 H 5 ZnOCH 3 ) 6 ], [C 2 H 5 ZnMP] 2 [ZnMP 2 ] 2 , trimethylaluminium, triethylaluminium and triisobutylaluminium, wherein MP is CH3OCH2CH(CH3)O—.

14. A partially fluorinated polyether of formula [OCRR 1 CR 2 R 3 ] n , wherein n is from 5 to 100, wherein R is H, R 1 is CF 3 , R 2 is F and R 3 is H or R is F, R 1 is CF 3 , R 2 is H and R 3 is H.

15. A lubricant composition comprising a partially fluorinated polyether according to claim 14 .

16. A heat transfer composition comprising a partially fluorinated polyether according to claim 14 .

Assignees

• Mexichem Fluor Sa De Cv

Inventors

• Murray James Henry
• Sharratt Andrew Paul

Classifications

• C07D301/26 Primary

  Y being hydrogen · CPC title

• C08G65/226

  containing fluorine · CPC title

• C10M107/38

  containing halogen · CPC title

• C10M2213/043

  used as base material · CPC title

• C10N2040/30

  Refrigerators lubricants {or compressors lubricants} · CPC title