Method for producing oxidation reaction product of hydrocarbon or derivative thereof, and method for producing oxidation reaction product of olefin

Patent metadata

Field	Value
Publication number	US-10947190-B2
Application number	US-201616063103-A
Country	US
Kind code	B2
Filing date	Dec 16, 2016
Priority date	Dec 18, 2015
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

The first aspect of the present invention is intended to provide a method for producing an oxidation reaction product of the hydrocarbon or a derivative thereof efficiently using hydrocarbon or a derivative thereof as a raw material. In order to achieve the above object, the first aspect of the present invention provides a method for producing an oxidation reaction product of a hydrocarbon or a derivative thereof. The method includes the step of irradiating a reaction system with light in the presence of a raw material and a chlorine dioxide radical. The raw material is hydrocarbon or a derivative thereof, the reaction system is a reaction system containing an organic phase, and the organic phase contains the raw material and the chlorine dioxide radical. In the step of irradiating a reaction system with light, the raw material is oxidized by the light irradiation to generate an oxidation reaction product of the raw material.

First claim

The invention claimed is:

1. A method for producing an oxidation reaction product, comprising the step of:
irradiating a reaction system with light in the presence of a raw material and a chlorine dioxide radical, wherein
the raw material is hydrocarbon or a derivative thereof,
the reaction system is a reaction system containing an organic phase,
the organic phase contains the raw material and the chlorine dioxide radical, and
in the step of irradiating a reaction system with light, the raw material is oxidized by the light irradiation to generate an oxidation reaction product of the raw material.

2. The method according to claim 1 , wherein
the reaction system is a biphasic reaction system that further contains an aqueous phase.

3. The method according to claim 2 , further comprising the step of:
recovering the oxidation reaction product after the step of irradiating a reaction system with light, wherein
the step of recovering the oxidation reaction product is a step of recovering the aqueous phase containing the oxidation reaction product from the reaction system.

4. The method according to claim 1 , wherein
the organic phase contains an organic solvent, and the organic solvent is a fluorous solvent.

5. The method according to claim 1 wherein
the raw material is methane.

6. The method according to claim 5 , wherein
the oxidation reaction product includes at least one selected from the group consisting of methanol, formic acid, formaldehyde, and methyl hydroperoxide.

7. The method according to claim 1 , wherein
the raw material is ethane.

8. The method according to claim 7 , wherein
the oxidation reaction product includes at least one selected from the group consisting of ethanol, acetic acid, acetaldehyde, and ethyl hydroperoxide.

9. The method according to claim 1 , wherein
the raw material is cyclohexane.

10. The method according to claim 9 , wherein
the oxidation reaction product includes at least one selected from the group consisting of cyclohexanol, cyclohexanone, cyclohexane hydroperoxide, and ring-opening oxide.

11. The method according to claim 10 , wherein
the ring-opening oxide is adipic acid.

12. A method for producing an oxidation reaction product of an olefin, comprising the steps of:
reacting at least one of a Lewis acid or a Brønsted acid with a radical source to generate a radical; and
oxidizing an olefin using the radical as an oxidizing agent, wherein
the Lewis acid has a Lewis acidity of 0.4 eV or more, and
the Brønsted acid has an acid dissociation constant pK a of 5 or more.

13. The method according to claim 12 , wherein
the Lewis acid includes metal ions.

14. The method according to claim 12 , wherein
the Lewis acid is at least one selected from the group consisting of alkali earth metal ions, rare earth ions, Mg 2+ , Sc 3+ , Li + , Fe 2+ , Fe 3+ , Al 3+ , silicate ions, and borate ions.

15. The method according to claim 12 , wherein
the Lewis acid is at least one selected from the group consisting of AlCl 3 , AlMeCl 2 , AlMe 2 Cl, BF 3 , BPh 3 , BMe 3 , TiCl 4 , SiF 4 , and SiCl 4 .

16. The method according to claim 12 , wherein
the radical source includes oxoacid.

17. The method according to claim 12 , wherein
the oxoacid includes a chlorite ion.

18. The method according to claim 12 , wherein
the olefin is an aromatic olefin.

19. The method according to claim 12 , wherein
the olefin is at least one selected from the group consisting of ethylene, propylene, styrene, and butadiene.

20. The method according to claim 12 , wherein
the oxidation reaction product is at least one of an epoxide or a diol.

Assignees

• Acenet Inc
• Univ Osaka

Inventors

• Takamori Kiyoto
• Shibata Takekatsu
• Ohkubo Kei

Classifications

• C07C2601/14

  The ring being saturated · CPC title

• C07C51/215

  of saturated hydrocarbyl groups · CPC title

• C07C46/04

  of unsubstituted ring carbon atoms in six-membered aromatic rings · CPC title

• C07C45/33

  of CHx-moieties · CPC title

• C07C37/60

  by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen · CPC title