Method for preparing α,β-unsaturated aldehyde

Patent metadata

Field	Value
Publication number	US-10981853-B2
Application number	US-201816771409-A
Country	US
Kind code	B2
Filing date	Jun 12, 2018
Priority date	Dec 12, 2017
Publication date	Apr 20, 2021
Grant date	Apr 20, 2021

Abstract

The present invention aims to provide a method for preparing an aldehyde, which can prepare a target aldehyde with high selectivity and can also suppress the production of by-products. The present invention relates to a method for preparing an α,β-unsaturated aldehyde. The method includes a step of reacting a compound of formula (I) with a compound of formula (II) to provide an α,β-unsaturated aldehyde of formula (III). An alkali metal hydroxide and an alkanol having 1 to 4 carbon atoms are used in the step. The amount of the alkali metal hydroxide is 8 mol % or more and 12 mol % or less with respect to the compound of formula (I). The total amount of water contained in materials that are used in the reaction is 10 mol % or more and 50 mol % or less with respect to the compound of formula (I).

First claim

The invention claimed is:

1. A method for preparing an α,β-unsaturated aldehyde, comprising:
reacting a compound of formula (I) with a compound of formula (II) to provide an α,β-unsaturated aldehyde of formula (III)
in the presence of an alkali metal hydroxide and an alkanol having 1 to 4 carbon atoms,
wherein an amount of the alkali metal hydroxide is 8 mol % or more and 12 mol % or less with respect to an amount of the compound of formula (I), and
a total amount of water contained in materials that are used in the reaction is 10 mol % or more and 50 mol % or less with respect to the amount of the compound of formula (I),

where R 1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms,
R 2 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms,
R 3 represents a hydrogen atom, or
R 2 and R 3 form 1,3-dioxolane together with carbon atoms to which R 2 and R 3 are bound, and
R 4 , R 5 , and R 6 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.

2. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein an amount of the compound of formula (II) used in the reaction is 1.5 equivalents or more with respect to the amount of the compound of formula (I).

3. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein the total amount of water contained in the materials that are used in the reaction is 12.5 mol % or more and 30 mol % or less with respect to the amount of the compound of formula (I).

4. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein R 1 represents an alkyl group having 3 to 8 carbon atoms.

5. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein the compound of formula (II) is a compound represented by any one of the following formulas:

6. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein the alkali metal hydroxide is lithium hydroxide, sodium hydroxide, or potassium hydroxide.

7. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein the alkanol having 1 to 4 carbon atoms is methanol or ethanol.

8. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein an amount of the alkanol having 1 to 4 carbon atoms is 300 mol % to 500 mol % with respect to the amount of the compound of formula (I).

9. The method for preparing the α,β-unsaturated aldehyde according to claim 1 , wherein the reaction includes adding the compound of formula (I) dropwise to a mixture of the alkanol, the alkali metal hydroxide, and the compound of formula (II).

10. The method for preparing the α,β-unsaturated aldehyde according to claim 9 , wherein the compound of formula (I) is added dropwise for a drop time of 3 hours or more and 9 hours or less.

11. The method for preparing the α,β-unsaturated aldehyde according to claim 9 , wherein the compound of formula (I) is added dropwise by changing a drop rate in multiple stages.

12. The method for preparing the α,β-unsaturated aldehyde according to claim 9 , wherein the compound of formula (I) is added dropwise by changing a drop rate in two stages.

13. The method for preparing the α,β-unsaturated aldehyde according to claim 12 , wherein the two stages include a stage corresponding to a first half period of a drop time and a stage corresponding to a second half period of the drop time, and
the drop rate during the second half period of the drop time is 0.2 times or more and 0.9 times or less the drop rate during the first half period of the drop time.

Assignees

• Kao Corp

Inventors

• Arai Tsubasa
• MASUMURA Kensuke
• KARASU Kensuke
• Nakagawa Yuki

Classifications

• C07C45/74 Primary

  combined with dehydration · CPC title

• C07C47/232

  having unsaturation outside the aromatic rings · CPC title