Method for producing fluorinated compounds

Patent metadata

Field	Value
Publication number	US-11247960-B2
Application number	US-201816649805-A
Country	US
Kind code	B2
Filing date	Sep 24, 2018
Priority date	Sep 26, 2017
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

The present invention relates to a process for the preparation of fluorinated compounds, to novel compounds containing fluorinated end groups, to the use thereof and to compositions comprising novel compounds containing fluorinated end groups.

First claim

The invention claimed is:

1. A process for preparing a compound of formula (I)

comprising
first preparing a compound of formula (II)

in a step a) by reacting a compound of formula (III) with glycidol (IV) to give a compound of formula (II)

and
converting said compound of formula (II) into a compound of formula (I), in a step b) by reacting the compound of formula (II) with an alcohol of formula (V) to give a compound of formula (I)

where
Rf is CF 3 —(CF 2 ) 0-3 —O—,
R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, and
Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms.

2. The process according to claim 1 , wherein Rf′ is of the following formula
CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —(CR 1 R 2 ) e —(CR 3 R 4 ) f —O g —,

where
R 1 , R 2 , R 3 and R 4 , independently of one another, are hydrogen or an alkyl group,
a=0, 1, 2 or 3,
b=0 or 1,
c=0, 1, 2 or 3,
d=0 or 1,
e=0, 1, 2, 3 or 4,
f=0, 1, 2, 3 or 4 and
g=0 or 1.

3. The process according to claim 1 , wherein Rf and Rf′ are different.

4. The process according to claim 1 , wherein Rf′ is a fluorinated C 1 -C 6 -alkyl group.

5. The process according to claim 1 , wherein R is a C 1 -C 20 alkyl group.

6. The process according to claim 1 , wherein Rf and/or Rf′ is a perfluorinated C 1 -C 4 -alkyl group.

7. The process according to claim 1 , wherein Rf and/or Rf′ is a perfluorinated C 3 -alkyl group.

8. The process according to claim 1 , wherein R is a C 6 -C 14 alkyl group.

9. The process according to claim 1 , wherein R is a siloxane group.

10. The process according to claim 1 , wherein R is Rf′.

11. The process according to claim 1 , wherein one of the following compounds of formula I is prepared

12. A process for preparing a compound of formula (I)

comprising
first preparing a compound of formula (II)

in a step a) by reacting a compound of formula (III) with glycidol (IV) to give a compound of formula (II)

and
converting said compound of formula (II) into a compound of formula (I), in a step b) by reacting the compound of formula (II) with an alcohol of formula (V) to give a compound of formula (I)

where
Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms,
R is a siloxane group, optionally containing one or more heteroatoms.

13. The process according to claim 12 , wherein Rf is of the following formula
CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —

where
a=0, 1, 2 or 3,
b=0 or 1,
c=0, 1, 2 or 3 and
d=0 or 1.

Assignees

• Merck Patent Gmbh

Inventors

• Friedrich Reiner
• Koch Fabian

Classifications

• C07C41/14 Primary

  by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification · CPC title

• C07C41/03

  by reaction of oxirane rings with hydroxy groups · CPC title

• C09D7/40

  Additives · CPC title

• C07D303/24 Primary

  with polyhydroxy compounds · CPC title

• C07C17/2637

  between a compound containing only oxygen and possibly halogen as hetero-atoms and a halogenated hydrocarbon · CPC title