Method for producing hydrogen peroxide

Patent metadata

Field	Value
Publication number	US-9919923-B2
Application number	US-201314413251-A
Country	US
Kind code	B2
Filing date	Jun 17, 2013
Priority date	Jul 10, 2012
Publication date	Mar 20, 2018
Grant date	Mar 20, 2018

Abstract

An object of the present invention is to provide a method by which hydrogen peroxide can be produced at a satisfactory level from an industrial and economical viewpoint without causing the load of purification to be large and without needing too large facilities for production. The present invention is directed to a method for producing hydrogen peroxide, which comprises reacting hydrogen and oxygen in a reaction medium in the presence of a noble metal catalyst and a radical scavenger.

First claim

The invention claimed is:

1. A method for producing hydrogen peroxide, comprising reacting hydrogen and oxygen in a reaction medium in the presence of a noble metal catalyst and a radical scavenger to produce hydrogen peroxide,
wherein the reaction medium is free of halogen ions, and
wherein the radical scavenger is capable of capturing OH radicals generated from decomposition of the hydrogen peroxide and forming a radical scavenger-OH adduct and is a nitrone compound of formula (1), (2), or (3), a nitroso compound of formula (4), a dithiocarbamate derivative of formula (5), or a compound of formula (6):

wherein, in formula (1), R 1 and R 2 are each independently an alkyl group having 1 to 10 carbon atoms and optionally having a branch, a phosphoric acid group, or a phosphate group, and
R 3 and R 4 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms and optionally having a branch, an alkyl group having 1 to 10 carbon atoms optionally having a branch and optionally being substituted with a hydroxyl group or an amino group, a 2-oxo-1-pyridylmethyl group, or an amino group,
in formula (2), R 5 is an alkyl group having 1 to 10 carbon atoms and optionally having a branch, and
R 6 to R 10 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms and optionally having a branch,
in formula (3), R 11 is an alkyl group having 1 to 10 carbon atoms and optionally having a branch, and
R 12 to R 15 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms and optionally having a branch,
in formula (4), R 16 is an alkyl group having 1 to 10 carbon atoms and optionally having a branch, or an aryl group having 6 to 20 carbon atoms and optionally being substituted with an alkyl group having 1 to 10 carbon atoms and optionally having a halogen, a sulfonic acid group, or a branch, and
in formula (5), R 17 and R 18 are each independently an alkyl group having 1 to 10 carbon atoms optionally having a branch and optionally being substituted with a hydroxyl group, or a carboxyalkyl group having 1 to 10 carbon atoms and optionally having a branch, and
X + is a cation.

2. The method according to claim 1 , wherein the radical scavenger is a nitrone compound of formula (1).

3. The method according to claim 1 , wherein, in formula (1), R 1 and R 2 are methyl groups, and R 3 and R 4 are each independently a methyl group, hydrogen, a 2-oxo-1-pyridylmethyl group, or an amino group,
in formula (2), R 5 is a methyl group, an ethyl group, an isopropyl group, a n-propyl group, a cyclopropyl group, a n-butyl group, a sec-butyl group, a tert-butyl group, or a cyclobutyl group, and R 6 to R 10 are hydrogen,
in formula (3), R 11 is a tert-butyl group, and R 12 to R 15 are hydrogen,
in formula (4), R 16 is a tert-butyl group, a 3,5-dibromo-1-sulfophenyl group, or a 2,3,5,6-tetramethylphenyl group; and
in formula (5), each of R 17 and R 18 is independently a methyl group, an ethyl group, or a carboxymethyl group, and X + is a sodium ion.

4. The method according to claim 1 , wherein the radical scavenger is 5,5-dimethyl-1-pyrroline N-oxide or N-tert-butyl-α-phenylnitrone.

5. The method according to claim 1 , wherein an amount of the radical scavenger is from 0.01 to 0.05 part by weight, relative to 100 parts by weight of the reaction medium.

6. The method according to claim 1 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

7. The method according to claim 3 , wherein an amount of the radical scavenger is from 0.01 to 0.05 part by weight, relative to 100 parts by weight of the reaction medium.

8. The method according to claim 4 , wherein an amount of the radical scavenger is from 0.01 to 0.05 part by weight, relative to 100 parts by weight of the reaction medium.

9. The method according to claim 3 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

10. The method according to claim 4 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

11. The method according to claim 5 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

12. The method according to claim 7 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

13. The method according to claim 8 , wherein the noble metal catalyst is a catalyst comprising silica, alumina, silica-alumina, titanium oxide, or zirconia oxide having supported thereon at least one metal selected from the group consisting of platinum, palladium, silver, and gold.

14. The method according to claim 1 , wherein the radical scavenger is a nitrone compound of formula (2).

15. The method according to claim 1 , wherein the radical scavenger is a nitrone compound of formula (3).

16. The method according to claim 1 , wherein the radical scavenger is a nitroso compound of formula (4).

17. The method according to claim 1 , wherein the radical scavenger is a dithiocarbamate derivative of formula (5).

18. The method according to claim 1 , wherein the radical scavenger is a compound of formula (6).

Assignees

• Mitsubishi Gas Chemical Co
• Univ Kyushu Nat Univ Corp

Inventors

• Ishihara Tatsumi
• Shigeta Kohei
• Iura Katsuhiro
• Kato Kenji
• Okuda Norikazu

Classifications

• C01B15/029 Primary

  Preparation from hydrogen and oxygen · CPC title

• B01J23/38

  of noble metals · CPC title

• B01J37/0203

  the impregnation liquid containing organic compounds · CPC title

• B01J21/063

  Titanium; Oxides or hydroxides thereof · CPC title

• B01J23/66

  Silver or gold · CPC title