Circular economic methods for fragrance ingredients

Patent metadata

Field	Value
Publication number	US-11873277-B2
Application number	US-202017578515-A
Country	US
Kind code	B2
Filing date	Jul 27, 2020
Priority date	Jul 26, 2019
Publication date	Jan 16, 2024
Grant date	Jan 16, 2024

Abstract

Disclosed is a method for converting cymene generated from renewable low value terpene streams into renewable benzene, toluene, xylenes, and cymene isomers (ortho and meta) under flow disproportionation reaction conditions, which compounds are basic building blocks for fragrance materials. This technology has potential to replace high volume petrochemical-based feedstocks with plant-based building blocks that can fill the renewability gap for key fragrance ingredients.

First claim

What is claimed is:

1. A process for producing a renewable aromatic backbone compound or a mixture thereof, comprising the step of contacting a renewable cymene with a suitable catalyst under flow disproportionation reaction conditions effective to convert the cymene to the renewable aromatic backbone compound selected from the group consisting of toluene, benzene, cymene isomers, xylenes and combinations thereof,
wherein the catalyst and flow disproportionation reaction conditions are selected so that the renewable cymene produces a mixture comprising renewable toluene and propylene.

2. The process of claim 1 , wherein the catalyst is an acidic zeolite catalyst.

3. The process of claim 2 , wherein the acidic zeolite is selected from the group consisting of ZSM-5, zeolite Y, beta zeolite, Sn on beta zeolite, lithium on beta zeolite, and combinations of two or more thereof.

4. The process of claim 2 , wherein the flow disproportionation reaction is carried out in the presence of an inert gas.

5. The process of claim 4 , wherein the inert gas is selected from the group consisting of nitrogen, helium and mixtures thereof.

6. The process of claim 2 , wherein the flow disproportionation reaction is carried out in the presence of a hydrogen gas.

7. The process of claim 6 , where the hydrogen gas pressure is about 1 to about 50 atmospheres.

8. The process of claim 6 , wherein the hydrogen-to-cymene molar ratio is about 0.1 to about 10.

9. The process of claim 8 , wherein the hydrogen-to-cymene molar ratio is about 2 to about 6.

10. The process of claim 2 , wherein the flow disproportionation reaction is carried out at a temperature ranging from about 60° C. to about 600° C.

11. The process of claim 10 , wherein the flow disproportionation reaction temperature ranges from about 300° C. to about 600° C.

12. The process of claim 2 , wherein the flow disproportionation reaction is carried out with a Weight Hourly Space Velocity (WHSV) from about 0.5 to about 10 hr −1 .

13. A process for producing a renewable aromatic backbone compound or a mixture thereof, comprising the step of contacting a renewable cymene with a suitable catalyst under flow disproportionation reaction conditions effective to convert the cymene to the renewable aromatic backbone compound selected from the group consisting of toluene, benzene, cymene isomers, xylenes and combinations thereof,
wherein the catalyst is an acidic zeolite catalyst, and the flow disproportionation reaction is carried out in the presence of an inert gas and/or a hydrogen gas.

14. The process of claim 13 , wherein the acidic zeolite is selected from the group consisting of ZSM-5, zeolite Y, beta zeolite, Sn on beta zeolite, lithium on beta zeolite, and combinations of two or more thereof.

15. The process of claim 13 , wherein the inert gas is selected from the group consisting of nitrogen, helium and mixtures thereof.

16. The process of claim 13 , where the hydrogen gas pressure is about 1 to about 50 atmospheres.

17. The process of claim 13 , wherein the hydrogen-to-cymene molar ratio is about 0.1 to about 10.

18. The process of claim 17 , wherein the hydrogen-to-cymene molar ratio is about 2 to about 6.

19. The process of claim 13 , wherein the flow disproportionation reaction is carried out at a temperature ranging from about 60° C. to about 600° C.

20. The process of claim 19 , wherein the flow disproportionation reaction temperature ranges from about 300° C. to about 600° C.

21. The process of claim 13 , wherein the flow disproportionation reaction is carried out with a Weight Hourly Space Velocity (WHSV) from about 0.5 to about 10 hr −1 .

Assignees

• Int Flavors & Fragrances Inc

Inventors

• Tadepalli Sunitha R
• Jones Paul Daniel
• Tampy Geatesh K
• Cherkauskas John P

Classifications

• C07C6/123 Primary

  of only one hydrocarbon · CPC title

• C07C5/2737

  with crystalline alumino-silicates, e.g. molecular sieves · CPC title

• C07C5/41

  Catalytic processes · CPC title

• C07C2521/08

  Silica · CPC title

• C07C2529/08

  of the faujasite type, e.g. type X or Y · CPC title