Method for producing m-dialkylbenzaldehyde

Patent metadata

Field	Value
Publication number	US-12024487-B2
Application number	US-202017634097-A
Country	US
Kind code	B2
Filing date	Jul 27, 2020
Priority date	Aug 23, 2019
Publication date	Jul 2, 2024
Grant date	Jul 2, 2024

Abstract

An object of the present invention is to provide a method for producing m-dialkylbenzaldehyde by using a reaction starting material containing 1,4-dialkylbenzene. The method for producing m-dialkylbenzaldehyde represented by formula (3), comprising a step of allowing carbon monoxide to react on a reaction starting material containing 1,4-dialkylbenzene represented by formula (1) in the presence of a Bronsted acid and a Lewis acid, wherein the reaction starting material is 1,4-dialkylbenzene represented by formula (1), or a mixture of 1,4-dialkylbenzene represented by formula (1) and 1,3-dialkylbenzene represented by formula (2), containing 10 mol % or more of the 1,4-dialkylbenzene represented by formula (1),
wherein in formulae (1) to (3), R 1 represents a methyl group or an ethyl group, and R 2 represents a chain or cyclic alkyl group having 3 or more and 6 or less carbon atoms that has a tertiary carbon at the benzyl position.

First claim

The invention claimed is:

1. A method for producing m-dialkylbenzaldehyde of formula (3), comprising:
contacting a reaction starting material with carbon monoxide in a presence of a Bronsted acid and a Lewis acid such that the carbon monoxide reacts on the reaction starting material which comprises either 1,4-dialkylbenzene of formula (1), or a mixture of 1,4-dialkylbenzene of the formula (1) and 1,3-dialkylbenzene of formula (2), the mixture comprising 10 mol % or more of the 1,4-dialkylbenzene,

wherein R 1 is a methyl group or an ethyl group, and R 2 is a chain or cyclic alkyl group having 3 to 6 carbon atoms and has a tertiary carbon at the benzyl position.

2. The method according to claim 1 , wherein the Bronsted acid is HF, and the Lewis acid is BF 3 or
the Bronsted acid is HCl, and the Lewis acid is AlCl 3 .

3. The method according to claim 1 , wherein the 1,4-dialkylbenzene of the formula (1) is selected from the group consisting of compounds of formulae (1-1) to (1-7),

wherein R 1 is a methyl group or an ethyl group.

4. The method according to claim 1 , wherein the reaction starting material is contacted with the carbon monoxide to react at a temperature in a range of from −30° C. to 30° C.

5. The method according to claim 1 , wherein the Bronsted acid is BF and the Lewis acid is BF 3 , and
wherein a molar ratio of HF to the reaction starting material is from 5.0 to 25.0.

6. The method according to claim 1 , wherein the Bronsted acid is HF, and the Lewis acid is BF 3 , and
wherein a molar ratio of BF 3 to the reaction starting material is from 0.2 to 2.5.

7. The method according to claim 1 , wherein the Bronsted acid is HCl, and the Lewis acid is AlCl 3 , and
wherein a molar ratio of HCl to the reaction starting material is from 0.0001 to 0.3.

8. The method according to claim 1 , wherein the Bronsted acid is HCl, and the Lewis acid is AlCl 3 , and
wherein a molar ratio of AlCl 3 to the reaction starting material is from 0.2 to 2.5.

9. The method according to claim 1 , wherein the reaction starting material is contacted with the carbon monoxide to react at a reaction pressure of from 1.0 MPaG to 3.0 MPaG.

10. The method according to claim 1 , wherein the reaction starting material is the mixture of the 1,4-dialkylbenzene and the 1,3-dialkylbenzene.

11. The method according to claim 10 , wherein the reaction starting material is contacted with the carbon monoxide to react at a temperature in a range of from −30° C. to 30° C.

12. The method according to claim 11 , wherein the reaction starting material is contacted with the carbon monoxide to react at a reaction pressure of from 1.0 MPaG to 3.0 MPaG.

13. The method according to claim 12 , wherein the Bronsted acid is HF, and the Lewis acid is BF 3 , and
wherein a molar ratio of HF to the reaction starting material is from 5.0 to 25.0.

14. The method according to claim 12 , wherein the Bronsted acid is HCl, and the Lewis acid is AlCl 3 , and
wherein a molar ratio of HCl to the reaction starting material is from 0.0001 to 0.3.

15. The method according to claim 1 , wherein the reaction starting material is the 1,4-dialkylbenzene.

16. The method according to claim 15 , wherein the reaction starting material is contacted with the carbon monoxide to react at a temperature in a range of from −30° C. to 30° C.

17. The method according to claim 16 , wherein the reaction starting material is contacted with the carbon monoxide to react at a reaction pressure of from 1.0 MPaG to 3.0 MPaG.

18. The method according to claim 17 , wherein the Bronsted acid is HF, and the Lewis acid is BF 3 , and
wherein a molar ratio of HF to the reaction starting material is from 5.0 to 25.0.

19. The method according to claim 17 , wherein the Bronsted acid is HCl, and the Lewis acid is AlCl 3 , and
wherein a molar ratio of HCl to the reaction starting material is from 0.0001 to 0.3.

20. The method according to claim 17 , wherein the Bronsted acid is HCl, and the Lewis acid is AlCl 3 , and
wherein a molar ratio of AlCl 3 to the reaction starting material is from 0.2 to 2.5.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Shishimi Toru
• Utamura Tatsuya
• Matsuura Yutaka
• Kumano Tatsuyuki

Classifications

• C07C47/542

  Alkylated benzaldehydes · CPC title

• C07C45/50 Primary

  by oxo-reactions · CPC title

• C07C45/49 Primary

  by reaction with carbon monoxide · CPC title