Fluorine-containing unsaturated compound and method for its production

• US 20050113609A1
• Filed: 01/03/2005
• Published: 05/26/2005
• Est. Priority Date: 07/03/2002
• Status: Abandoned Application

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Furukawa, Yutaka
• Application Number:
  US11/026,012
• Publication Number:
  US 20050113609A1
• Time in Patent Office: Days
• US Class Current: 568/685
• CPC Class Codes: C07C 43/17 containing halogen

Abstract

A novel fluorine-containing unsaturated compound and a method for its production.

A fluorine-containing unsaturated compound represented by R¹CY¹HCY²Y³OQ¹CH═CH₂ or CH₂═CHQ²OCZ¹Z²CZ³HR²CZ⁴HCZ⁵Z⁶OQ²CH═CH₂ (wherein R¹ is a monovalent fluorine containing organic group, etc., R² is a bivalent fluorine containing organic group, etc., Y¹ to Y³ and Z¹ to Z⁶ are fluorine atoms, and Q¹ and Q² are alkylene groups, etc.). A method for producing a fluorine-containing unsaturated compound having a group represented by —CX¹HCX²X³OQCH═CH₂ (wherein X¹ to X³ are fluorine atoms, and Q is an alkylene group, etc.), which comprises reacting a compound having —CX¹═CX²X³ with HOQCH═CH₂ in the presence of an alkali metal compound.

Claims

1. A fluorine-containing unsaturated compound represented by the following formula (1) or (2):

R¹CY¹HCY²Y³OQ¹CH═

CH₂  

 

Formula 1
CH₂═

CHQ²OCZ¹Z²CZ³HR²CZ⁴HCZ⁵Z⁶OQ³CH═

CH₂  

 

Formula 2

wherein the symbols in the formulae (1) and (2) have the following meanings;

R¹;

a monovalent organic group, a halogen atom or a hydrogen atom;

R²;

a bivalent organic group;

Y¹, Y² and Y³;

independently hydrogen atoms or fluorine atoms provided that when R¹ is not a fluorine atom, at least one of Y¹, Y² and Y³ is a fluorine atom;

Z¹, Z², Z³, Z⁴, Z⁵ and Z⁶;

independently hydrogen atoms or fluorine atoms provided that at least one of Z¹, Z² and Z³ is a fluorine atom, and at least one of Z⁴, Z⁵ and Z⁶ is a fluorine atom;

Q¹, Q² and Q³;

independently bivalent organic groups.

3. The fluorine-containing unsaturated compound according to claim 1, wherein R¹ in the formula (1) is a monovalent perfluorohydrocarbon group containing an etheric oxygen atom, and R² in the formula (2) is a bivalent perfluorohydrocarbon group containing an etheric oxygen atom.

4. The fluorine-containing unsaturated compound according to claim 1, wherein Q¹ in the formula (1), and Q² and Q³ in the formula (2) are —

(CH₂)_t—

(t is an integer of at least

     1).

5. The fluorine-containing unsaturated compound according to claim 1, wherein the compound represented by the formula (1) is R′

CFHCF₂O(CH₂)_mCH═

CH₂ (wherein R′

is a monovalent fluorine-containing C_1-16 organic group containing an etheric oxygen atom, and m is an integer of from 1 to

     12), and the compound represented by the formula (2) is R″

[CFHCF₂O(CH₂)_qCH═

CH₂]₂ (wherein R″

is a bivalent fluorine-containing C_1-16 organic group containing an etheric oxygen atom, and q is an integer of from 1 to

     12).

2. A method for producing a fluorine-containing unsaturated compound having a group represented by the following formula (5), which comprises reacting a compound having a group represented by the following formula (3) and a compound represented by the following formula (4) in the presence of an alkali metal compound:

—

CX¹═

CX²X³  

 

Formula 3
HOQCH═

CH₂  

 

Formula 4
—

CX¹HCX²X³OQCH═

CH₂  

 

Formula 5

wherein the symbols in the formulae (3), (4) and (5) have the following meanings;

X¹, X² and X³;

independently hydrogen atoms or fluorine atoms provided that at least one of X¹, x² and X³ is a fluorine atom;

Q;

a bivalent organic group.

6. The fluorine-containing unsaturated compound according to claim 2, wherein Q in the formula (4) or (5) is —

(CH₂)_t—

(t is an integer of at least

     1).

7. The method for producing a fluorine-containing unsaturated compound according to claim 2, wherein the compound represented by the formula (3) is a compound represented by the following formula (6).

R[CX¹═ CX²X³]_p  

 

Formula 6

wherein the symbols in the formula (6) have the following meanings;

R;

a p-valent organic group;

p;

an integer of from 1 to 4;

X¹, X² and X³;

independently hydrogen atoms or fluorine atoms provided that at least one of X¹, X² and X³ is a fluorine atom;

8. The method for producing a fluorine-containing unsaturated compound according to claim 2, wherein the reaction is carried out in a two layer system consisting of an organic solvent and an aqueous alkaline solution in the presence of a phase-transfer catalyst.

9. The method for producing a fluorine-containing unsaturated compound according to claim 2, wherein the reaction is carried out in the presence of a polymerization inhibitor.