Method for producing perfluoropolyether acyl fluoride

Patent metadata

Field	Value
Publication number	US-10508171-B2
Application number	US-201615562184-A
Country	US
Kind code	B2
Filing date	Mar 31, 2016
Priority date	Mar 31, 2015
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

A process for producing a perfluoropolyether acyl fluoride which includes reducing a peroxyperfluoropolyether by using a formyl group-containing compound in the presence of a transition metal catalyst.

First claim

The invention claimed is:

1. A process for producing a perfluoropolyether acyl fluoride which comprises reducing a peroxyperfluoropolyether with a formyl group-containing compound in the presence of a transition metal catalyst, wherein the formyl group-containing compound is formic acid or formic acid derivatives.

2. The process according to claim 1 wherein the perfluoropolyether acyl fluoride is a compound of the following formula (I):
X—(C 4 F 8 O) a —(C 3 F 6 O) b —(C 2 F 4 O) c —(CF 2 O) d —Y

wherein:
a, b, c and d are each independently 0 or an integer of 1 or more, the sum of a, b, c and d is at least 1, and the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula,
X is —R 5 ,
R 5 is —F, —COF, —CF 3-m Cl m ,
m is an integer of 1-3,
Y is —(CF 2 ) n —COF, and
n is an integer of 0-3.

3. The process according to claim 1 wherein perfluoropolyether acyl fluoride is a compound of the following formula (I′):
X—(C 4 F 8 O) a —(C 3 F 6 O) b —(C 2 F 4 O) c —(CF 2 O) d —Y

wherein:
a and b are each independently 0 or more and 30 or less,
c and d are each independently 1 or more and 200 or less, and
the occurrence order of the respective repeating units in parentheses with the subscript a, b, c or d is not limited in the formula,
X is —R 5 ,
R 5 is —F, —COF, —CF 3-m Cl m ,
m is an integer of 1-3,
Y is —(CF 2 ) n —COF, and
n is an integer of 0-3.

4. The process according to claim 1 wherein the formyl group-containing compound is formic acid.

5. The process according to claim 1 wherein the peroxyperfluoropolyether compound comprises the following structure (II):
—(C 4 F 8 O) a —(C 3 F 6 O) b —(C 2 F 4 O) c —(CF 2 O) d —(C 4 F 8 —O—O) p —(C 3 F 6 —O—O) q —(C 2 F 4 —O—O) r —(CF 2 —O—O) s —

wherein:
a, b, c, d, p, q, r and s are each independently 0 or an integer of 1 or more, the sum of a, b, c and d is at least 1, and the sum of p, q, r and s is at least 1, and
the occurrence order of the respective repeating units in parentheses with the subscript a, b, c, d, p, q, r or s is not limited in the formula.

6. The process according to claim 1 wherein the transition metal is selected form Pd, Pt, Rh, Ru and a mixture thereof.

7. The process according to claim 1 wherein the used amount of the transition metal catalyst is in the range of 0.1 to 10.0% by mass with respect to peroxyperfluoropolyether.

8. The process according to claim 1 wherein the used amount of the transition metal catalyst is in the range of 1.0 to 10.0% by mass with respect to peroxyperfluoropolyether.

9. The process according to claim 1 wherein the reaction temperature is 50 to 200° C.

10. The process according to claim 1 wherein the reaction temperature is 50 to 150° C.

11. The process according to claim 1 which is performed in a solvent-free condition.

12. The process according to claim 1 which is performed in a non-aqueous solvent.

Assignees

• Daikin Ind Ltd

Inventors

• Takano Shinya
• Nomura Takashi
• Katsukawa Kenichi
• Naitou Masato

Classifications

• C07B31/00

  Reduction in general · CPC title

• C08G65/3322

  acyclic · CPC title

• B01J23/42

  Platinum · CPC title

• C08G65/332

  containing carboxyl groups, or halides, or esters thereof · CPC title

• C08G65/007 Primary

  containing fluorine · CPC title