Process for preparing (meth)acrylic esters of functionalized furyl alcohols

Patent metadata

Field	Value
Publication number	US-9938548-B2
Application number	US-201514974267-A
Country	US
Kind code	B2
Filing date	Dec 18, 2015
Priority date	Dec 22, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The invention relates to a process for preparing a compound of the formula (I),

in which R is H or C 1 -C 6 alkyl,
by reaction of at least one compound of the formula (II)

in which R has the same definition as in the formula (I) and
in which R 1 is H, C 1 -C 12 alkyl or C 3 -C 12 cycloalkyl,
with a compound of the formula (III)

in which R 2 is H or C(O)R 3 ,
in which R 3 is H or C 1 -C 12 alkyl,
in the presence of at least one enzyme suitable for transesterification.

First claim

What is claimed is:

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

wherein R is H or C 1 -C 6 alkyl,

the process comprising:
reacting at least one compound of the formula (II)

wherein R is H or C 1 -C 6 alkyl, and R 1 is H, C 1 -C 12 alkyl or C 3 -C 12 cycloalkyl, with a compound of the formula (III)

wherein R 2 is H or C(O)R 3 , and R 3 is H or C 1 -C 12 alkyl,

in the presence of at least one enzyme suitable for transesterification, and
in the presence of at least one stabilizer.

2. The process according to claim 1 , where R is H or CH 3 .

3. The process according to claim 1 , where R is H.

4. The process according to claim 1 , where R is CH 3 .

5. The process according to claim 1 , where R 1 is CH 3 or CH 2 CH 3 .

6. The process according to claim 1 , where R 2 is H.

7. The process according to claim 1 , wherein the at least one enzyme comprises a hydrolase (EC 3.-.-.-).

8. The process according to claim 1 , wherein the at least one enzyme comprises a lipase(EC 3.1.1.-).

9. The process according to claim 1 , wherein the at least one compound of the formula (II) and the compound of the formula (III) are reacted in a molar ratio of 5:1 to 15:1.

10. The process according to claim 1 , wherein the process is carried out at a temperature of from 20 to 60° C.

11. The process according to claim 1 , wherein R 2 is C(O)R 3 and/or R is C 1 -C 6 alkyl.

Assignees

• Basf Se

Inventors

• Fleckenstein Christoph
• Blanchot Mathieu
• Blank Benoit
• Kaller Martin
• Stengel Ulrik
• Misske Andrea
• Fleischhaker Friederike
• Nair Ritesh

Classifications

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C07D307/46

  Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom · CPC title

• C12P17/04 Primary

  containing a five-membered hetero ring, e.g. griseofulvin {, vitamin C} · CPC title

• C08F20/32

  containing epoxy radicals · CPC title

• C08F220/28

  containing no aromatic rings in the alcohol moiety · CPC title