Method for producing p-xylene and/or p-tolualdehyde

Patent metadata

Field	Value
Publication number	US-9024074-B2
Application number	US-201314374449-A
Country	US
Kind code	B2
Filing date	Jan 23, 2013
Priority date	Jan 26, 2012
Publication date	May 5, 2015
Grant date	May 5, 2015

Abstract

Disclosed is a method for producing p-xylene and/or p-tolualdehyde with high yield through a short process using biomass resource-derived substances as raw materials. The method for producing p-xylene and/or p-tolualdehyde of the present invention comprises: a cyclization step of producing 4-methyl-3-cyclohexenecarboxaldehyde from isoprene and acrolein; and an aromatization step of producing p-xylene and/or p-tolualdehyde from 4-methyl-3-cyclohexenecarboxaldehyde by gas-phase flow reaction using a catalyst(s).

First claim

The invention claimed is:

1. A method for producing p-xylene and/or p-tolualdehyde, said method comprising:
a cyclization step of producing 4-methyl-3-cyclohexenecarboxaldehyde from isoprene and acrolein; and
an aromatization step of producing p-xylene and/or p-tolualdehyde from 4-methyl-3-cyclohexenecarboxaldehyde by gas-phase flow reaction using a catalyst(s).

2. The production method according to claim 1 , wherein the catalyst used in the aromatization step comprises a carrier which carries a metal(s) and/or metal oxide(s).

3. The production method according to claim 1 , wherein the catalyst used in the aromatization step comprises a carrier which carries at least one metal or metal oxide, said metal or metal oxide being selected from the group consisting of platinum, nickel, palladium, ruthenium, platinum oxide, copper oxide, iron oxide and chromium oxide.

4. The production method according to claim 1 , wherein the catalyst used in the aromatization step comprises a carrier selected from the group consisting of alumina, silica-alumina, silica, zeolite, titania, magnesia and carbon.

5. The production method according to claim 1 , wherein the catalyst used in the aromatization step is chromium oxide on alumina, chromium oxide on silica-alumina or chromium oxide on silica.

6. The production method according to claims 1 , wherein the reaction temperature in the gas-phase flow reaction in the aromatization step is 300° C. to 500° C.

7. The production method according to claim 1 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

8. The production method according to claim 2 , wherein the catalyst used in the aromatization step comprises a carrier which carries at least one metal or metal oxide, said metal or metal oxide being selected from the group consisting of platinum, nickel, palladium, ruthenium, platinum oxide, copper oxide, iron oxide and chromium oxide.

9. The production method according to claim 2 , wherein the catalyst used in the aromatization step comprises a carrier selected from the group consisting of alumina, silica-alumina, silica, zeolite, titania, magnesia and carbon.

10. The production method according to claim 3 , wherein the catalyst used in the aromatization step comprises a carrier selected from the group consisting of alumina, silica-alumina, silica, zeolite, titania, magnesia and carbon.

11. The production method according to claim 2 , wherein the catalyst used in the aromatization step is chromium oxide on alumina, chromium oxide on silica-alumina or chromium oxide on silica.

12. The production method according to claim 3 , wherein the catalyst used in the aromatization step is chromium oxide on alumina, chromium oxide on silica-alumina or chromium oxide on silica.

13. The production method according to claim 4 , wherein the catalyst used in the aromatization step is chromium oxide on alumina, chromium oxide on silica-alumina or chromium oxide on silica.

14. The production method according to claim 2 , wherein the reaction temperature in the gas-phase flow reaction in the aromatization step is 300° C. to 500° C.

15. The production method according to claim 3 , wherein the reaction temperature in the gas-phase flow reaction in the aromatization step is 300° C. to 500° C.

16. The production method according to claim 4 , wherein the reaction temperature in the gas-phase flow reaction in the aromatization step is 300° C. to 500° C.

17. The production method according to claim 5 , wherein the reaction temperature in the gas-phase flow reaction in the aromatization step is 300° C. to 500° C.

18. The production method according to claim 2 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

19. The production method according to claim 3 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

20. The production method according to claim 4 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

21. The production method according to claim 5 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

22. The production method according to claim 6 , wherein the cyclization step is carried out in the presence of a catalyst comprising a Lewis acid.

Assignees

• Toray Industries

Inventors

• Sakami Satoshi
• Tsukamoto Daijiro
• Yamada Katsushige

Classifications

• B01J23/462

  Ruthenium · CPC title

• C07C1/207

  from carbonyl compounds · CPC title

• C07C2523/42

  Platinum · CPC title

• B01J23/72

  Copper · CPC title

• B01J23/44

  Palladium · CPC title