Method for preparing carboxylic esters from aldehydes

Patent metadata

Field	Value
Publication number	US-10640448-B2
Application number	US-201815967463-A
Country	US
Kind code	B2
Filing date	Apr 30, 2018
Priority date	May 17, 2017
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

A method can prepare a carboxylic ester. The method includes reacting an aldehyde in the presence of an aluminium alkoxide applied to a support material.

First claim

The invention claimed is:

1. A method for preparing a carboxylic ester, the method comprising:
reacting (meth)acrolein in the presence of an aluminum alkoxide applied to a support material comprising silicon dioxide.

2. The method according to claim 1 , wherein the aluminum alkoxide is a compound of formula (II):
Al(OR 2 ) 3   (II),

wherein each R 2 radical is independently of one another a —(C 1 -C 12 )-alkyl group or a —(C 2 -C 12 )-alkenyl group and each R 2 radical may independently of one another optionally be substituted by one or more substituents selected from the group consisting of —(C 1 -C 12 )-alkyl, —(C 3 -C 12 )-cycloalkyl, —(C 4 -C 12 )-heterocycloalkyl, —(C 6 -C 20 )-aryl, —(C 4 -C 20 )-heteroaryl, —O—(C 1 -C 12 )-alkyl, —O—(C 3 -C 12 )-cycloalkyl, —S—(C 1 -C 12 )-alkyl, —S—(C 3 -C 12 )-cycloalkyl, —COO—(C 1 -C 12 )-alkyl, —COO—(C 3 -C 12 )-cycloalkyl, —CONH—(C 1 -C 12 )-alkyl, —CONH—(C 3 -C 12 )-cycloalkyl, —N—[(C 1 -C 12 )-alkyl] 2 , —OH, —NH 2 , and a halogen atom.

3. The method according to claim 1 , wherein the aluminum alkoxide is a compound of formula (III)
Al(OCH 2 R 3 ) 3   (III),

wherein each of the R 3 radicals corresponds to C 2 alkenyl or methyl substituted C 2 alkenyl.

4. The method according to claim 2 , wherein each R 2 group is, independently, a group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, allyl, and 2-methylallyl.

5. The method according to claim 1 , wherein said reacting is carried out at a reaction temperature of 10 to 60° C.

6. The method according to claim 1 , wherein said reacting is carried out continuously.

7. The method according to claim 1 , wherein said (meth)acrolein is reacted without addition of solvent.

Assignees

• Evonik Operations Gmbh

Inventors

• Lygin Alexander
• Krill Steffen
• Grömping Matthias
• Tepperis Andreas

Classifications

• B01J23/18

  Arsenic, antimony or bismuth · CPC title

• B01J31/0212

  Alkoxylates · CPC title

• B01J23/04

  Alkali metals · CPC title

• C07C67/44 Primary

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title

• B01J21/14

  Silica and magnesia · CPC title