Process of preparing 4-methyl-3-decen-5-one

Patent metadata

Field	Value
Publication number	US-9815758-B2
Application number	US-201615375252-A
Country	US
Kind code	B2
Filing date	Dec 12, 2016
Priority date	Dec 14, 2015
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

A method of preparing 4-methyl-3-decen-5-one. The method includes the step of oxidizing 4-methyl-3-decen-5-ol in the presence of (i) oxygen and (ii) a metal catalyst, wherein the metal catalyst contains a catalytic metal deposited on nanoparticle support.

First claim

What is claimed is:

1. A method of preparing 4-methyl-3-decen-5-one, the method comprising oxidizing 4-methyl-3-decen-5-ol in the presence of (i) an oxygen-containing gas and (ii) a metal catalyst, wherein the metal catalyst is a sodium-doped gold catalyst containing gold (Au) and sodium (Na) deposited on a nanoparticle support.

2. The method of claim 1 , wherein the nanoparticle support is iron oxide, titanium oxide, cerium oxide, zirconium oxide, alumina, charcoal, hydroxyapatite, or any combination thereof.

3. The method of claim 2 , wherein the nanoparticle support is cerium oxide.

4. The method of claim 3 , wherein the metal catalyst is doped with Na in an amount of 10 to 40,000 ppm by weight of the metal catalyst.

5. The method of claim 1 , wherein Au is present in an amount of 0.2 to 10% by weight of the metal catalyst.

6. The method of claim 1 , wherein the oxygen-containing gas is provided in the form of an oxygen gas, air, stripped air, enriched air, or any combination thereof.

7. The method of claim 1 , wherein the reaction is performed at a temperature of 20 to 240° C., and at a pressure of 0.1 to 20 bars.

8. The method of claim 1 , wherein the reaction is performed in the presence or absence of a solvent, when a solvent is used, the solvent is selected from the group consisting of a nitrile, a halogen- or non-halogen-containing alkyl and/or aromatic solvent, a carboxylic acid solvent, and any combination thereof.

9. The method of claim 1 , wherein the reaction is performed in a batch reactor or a continuous reactor.

10. The method of claim 9 , wherein the continuous reactor is a single CSTR, multiple CSTRs in series, or a microreactor.

11. The method of claim 9 , wherein the continuous reactor is a packed bed reactor packed with a glass bead, metal catalyst, or a combination thereof.

12. The process of claim 11 , wherein the catalyst has a volume in the reactor ranging from 20 to 90%.

13. The process of claim 10 , wherein the continuous reactor is a microreactor containing channels each having an internal diameter ranging from 0.1 to 200 mm.

14. The process of claim 4 , wherein the metal catalyst is doped with Na in an amount of 100 to 20,000 ppm by weight of the metal catalyst.

15. The process of claim 14 , wherein the oxygen-containing gas is provided in the form of an oxygen gas, and the reaction is performed in the absence of a solvent at a temperature of 60 to 140° C. and a pressure of 1 to 15 bars.

16. The process of claim 1 , wherein the catalyst is present in the amount of 6 to 50% by weight of 4-methyl-3-decen-5-ol.

17. The process of claim 16 , wherein the metal catalyst is a sodium-doped gold catalyst containing gold and sodium deposited on a cerium dioxide nanoparticle support.

18. The process of claim 17 , wherein the sodium content is between 200 and 10,000 ppm by weight of the metal catalyst.

19. The method of claim 18 , wherein the oxygen-containing gas is provided in the form of an oxygen gas, air, stripped air, enriched air, or any combination thereof.

20. The method of claim 19 , wherein the reaction is performed at a temperature of 20 to 240° C., and at a pressure of 0.1 to 20 bars.

Assignees

• Int Flavors & Fragrances Inc

Inventors

• Canós Avelino Corma
• Chornet Sara Iborra
• Velty Alexandra
• Sans Manuel Querol
• Miranda Amadeo Fernández
• Gomez Jaime Renovell

Classifications

• B01J23/52

  Gold · CPC title

• B01J23/688

  with manganese, technetium or rhenium · CPC title

• B01J37/04

  Mixing {(B01J37/0009, B01J37/0018 take precedence)} · CPC title

• B01J23/66

  Silver or gold · CPC title

• B01J23/8906

  Iron and noble metals · CPC title