Methods of making halogenated fluorinated ether-containing compounds

Patent metadata

Field	Value
Publication number	US-9828320-B2
Application number	US-201515529104-A
Country	US
Kind code	B2
Filing date	Nov 20, 2015
Priority date	Dec 1, 2014
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

Described herein are three methods for making halogenated fluorinated ether-containing compounds using a fluorinated olefin or hexafluoropropylene oxide.

First claim

What is claimed is:

1. A method of making a halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
(i) halogenating a difluorosulfuryl peroxide followed by reaction with a first fluoroolefin to form a halogenated fluoroorganyl acid fluoride;
(ii) reacting the halogenated fluoroorganyl acid fluoride with first compound selected from at least one of:
(a) a second fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound; and
(b) HFPO to form a corresponding acid fluoride and converting the corresponding acid fluoride into the halogenated fluorinated ether-containing compound.

2. The method of claim 1 , wherein converting the corresponding acid fluoride is selected from:
(i) reacting the corresponding acid fluoride with a third fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound;
(ii) pyrolyzing the corresponding acid fluoride to form a vinyl ether; then reacting the vinyl ether with an interhalogen to form the halogenated fluorinated ether-containing compound;
(iii) reacting the corresponding acid fluoride with CF 2 ═CF—CF 2 —OSO 2 F to form the halogenated fluorinated ether-containing compound; or
(iv) reacting the corresponding acid fluoride with LiI to form the halogenated fluorinated ether-containing compound.

3. The method of claim 1 , further comprising reacting the corresponding acid fluoride with HFPO to form an elongated acid fluoride, which is then converted into the halogenated fluorinated ether-containing compound.

4. The method of claim 1 , wherein the halogenated fluorinated ether-containing compound has the structure selected from at least one of:
X—CFYCF 2 —[OCF(CF 3 )CF 2 ] n —O—R F   (I)

wherein X is selected from Br, Cl and I; Y is F or CF 3 ; n is an integer from 0-3 and R F is CF═CF 2 and CF 2 CF═CF 2 ; and
X—CFYCF 2 —[OCF(CF 3 )CF 2 ] n —O—R f —X 1   (II)

wherein X and X 1 are independently selected from Br, Cl and I; Y is F or CF 3 ; R f is selected from CF 2 CF 2 , CF(CF 3 )CF 2 , CFClCF 2 , or CH 2 CF 2 ; and n is an integer from 1-3.

5. A method of making a halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
(i) forming 2,2,3,3-tetrafluoro-3-halogenopropanenitrile using a cyanide containing compound and TFE wherein the forming is selected from:
a) adding XCN to TFE wherein X is I, Br or Cl; and
b) adding MCN to TFE wherein M is an alkali metal followed by contact with a halogen containing compound;

(ii) converting the 2,2,3,3-tetrafluoro-3-halogenopropanenitrile to 2,2,3,3-tetrafluoro-3-halogenopropanoyl fluoride;
(iii) reacting the 2,2,3,3-tetrafluoro-3-halogenopropanoyl fluoride with a first compound selected from at least one of
(a) a fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound and
(b) HFPO to form the corresponding acid fluoride and converting the corresponding acid fluoride into a halogenated fluorinated ether-containing compound.

6. The method of claim 5 , wherein the converting of the corresponding acid fluoride is selected from:
(a) reacting the corresponding acid fluoride with a second compound selected from at least one of (i) a third fluoroolefin in the presence of a halogen containing compound to form the corresponding halogenated ether-containing compound and (ii) HFPO to form the corresponding acid fluoride;
(b) pyrolizing the corresponding acid fluoride to form a vinyl ether; then reacting the vinyl ether with an interhalogen to form the halogenated fluorinated ether-containing compound;
(c) reacting the corresponding acid fluoride with CF 2 ═CF—CF 2 —OSO 2 F to form the the halogenated fluorinated ether-containing compound; or
(d) reacting the corresponding acid fluoride with LiI to form the halogenated fluorinated ether-containing compound.

7. The method of claim 5 , wherein the halogenated fluorinated ether-containing compound has the structure selected from at least one of:
X—CF 2 CF 2 CF 2 —[OCF(CF 3 )CF 2 ] n —O—R F   (I)

wherein X is selected from I, Br and Cl, n is an integer from 0-3; and R F is CF═CF 2 and CF 2 CF═CF 2 ; and
X—CF 2 CF 2 CF 2 —[OCF(CF 3 )CF 2 ] n —O—R F′ —X 1   (II)

wherein X and X 1 are independently selected from I, Br and Cl; R F′ is selected from CF 2 CF 2 , CFClCF 2 , or CH 2 CF 2 ; and n is an integer from 0-3.

8. A method of making halogenated fluorinated ether-containing compound from a fluoroolefin, the method comprising:
(i) reacting a perfluoroorganyl diacid difluoride with a first compound selected from at least one of
(a) a first fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound; and
(b) HFPO to form the corresponding diacid difluoride and converting the corresponding diacid difluoride into the halogenated fluorinated ether-containing compound.

9. The method of claim 8 , wherein the converting step is selected from:
(i) reacting the corresponding diacid difluoride with a second compound selected from at least one of
(a) a second fluoroolefin in the presence of a halogen containing compound to form the halogenated fluorinated ether-containing compound and
(b) reacting the corresponding acid fluoride with HFPO to form an acid fluoride

(ii) pyrolizing the corresponding acid fluoride to form a vinyl ether; then reacting the vinyl ether with an interhalogen to form the halogenated fluorinated ether-containing compound;
(iii) reacting the corresponding acid fluoride with CF 2 ═CF—CF 2 —OSO 2 F to form the halogenated fluorinated ether-containing compound; or
(iv) reacting the corresponding acid fluoride with LiI to form the halogenated fluorinated ether-containing compound.

10. The method of claim 8 , wherein the halogenated fluorinated ether-containing compound has the structure selected from at least one of:
X—R F —[OCF(CF 3 )CF 2 ] n —O—(CF 2 ) o —[OCF(CF 3 )CF 2 ] n —O—R F′   (III)

wherein X is selected from I, Br and Cl; R F is CF 2 CF 2 or CF 2 CF 2 CF 2 ; n is an integer from 0-3; o is an integer from 2-6, 8, and 10; and R F′ is CF═CF 2 and CF 2 CF═CF 2 ; and
X—R F —[OCF(CF 3 )CF 2 ] n —O—(CF 2 ) o —[OCF(CF 3 )CF 2 ] n —O—R F —X 1   (IV)

wherein X and X 1 are independently selected from I, Br and Cl; R F is independently CF 2 —CF 2 , CF(CF 3 )CF 2 , CFClCF 2 , or CH 2 CF 2 ; n is an integer from 0-3; o is an integer from 2-6, 8, and 10.

11. The method of claim 1 , wherein the first fluoroolefin is selected from at least one of tetrafluoroethylene, hexafluoropropylene, and chlorotrifluoroethylene.

12. The method of claim 1 , wherein the second fluoroolefin is selected from at least one of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, and chlorotrifluoroethylene.

13. The method of claim 2 , wherein the third fluoroolefin is selected from at least one of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, and chlorotrifluoroethylene.

14. The method of claim 6 , wherein the second fluoroolefin is selected from at least one of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, and chlorotrifluoroethylene.

15. The method of claim 6 , wherein the third fluoroolefin is selected from at least one of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, and chlorotrifluoroethylene.

16. The method of claim 5 , further comprising reacting the corresponding acid fluoride with HFPO to form

Assignees

• 3M Innovative Properties Co

Inventors

• Hintzer Klaus
• Hirschberg Markus E
• Lochhaas Kai Helmut
• Schwertfeger Werner
• Shyshkov Oleg
• Thaler Arne

Classifications

• C07C253/10

  to compounds containing carbon-to-carbon double bonds · CPC title

• C07C253/00

  Preparation of carboxylic acid nitriles (of cyanogen or compounds thereof C01C3/00) · CPC title

• C07C51/58 Primary

  Preparation of carboxylic acid halides · CPC title

• C07C45/518

  involving transformation of sulfur-containing compounds to >C = O groups · CPC title

• C07C41/01 Primary

  Preparation of ethers · CPC title