Methods of making halogenated fluorinated ether-containing compounds

Patent metadata

Field	Value
Publication number	US-2017260116-A1
Application number	US-201515529104-A
Country	US
Kind code	A1
Filing date	Nov 20, 2015
Priority date	Dec 1, 2014
Publication date	Sep 14, 2017
Grant date	—

Abstract

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

First claim

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 RF 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; RF 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 wit

Assignees

• 3M Innovative Properties Co

Inventors

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

Classifications

• C07C303/30

  by reactions not involving the formation of esterified sulfo groups · CPC title

• C07C41/01 Primary

  Preparation of ethers · CPC title

• C07C51/58 Primary

  Preparation of carboxylic acid halides · CPC title

• C07C303/24

  of esters of sulfuric acids · CPC title

• C07C253/10

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