Catalyst, and method for producing oxidation product

Patent metadata

Field	Value
Publication number	US-10005718-B2
Application number	US-201515116699-A
Country	US
Kind code	B2
Filing date	Feb 4, 2015
Priority date	Feb 7, 2014
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

A novel catalyst is provided which enables efficient production of an oxidation product by using an oxygen-induced oxidation reaction of an organic substrate. A novel method of using the catalyst enables efficient manufacturing of the oxidation product by oxidizing the organic substrate using oxygen. A catalyst used in the oxidation reaction of the organic substrate using oxygen contains compound (A), compounds (A) and (B), compounds (A) and (C), compounds (B) and (C), or compounds (A) and (B) and (C). A method for manufacturing the oxidation product using the catalyst involves bringing the organic substrate into contact with oxygen. Compound (A) is an inorganic peroxo acid, a salt of an inorganic peroxo acid, and/or N-halogenated succinimide, compound (B) is a nitroxide and/or a peroxide, and compound (C) is layered silicate.

First claim

The invention claimed is:

1. A method for producing an oxime having the following formula (II):

wherein each of R 1 and R 2 is independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group, provided that not both R 1 and R 2 are hydrogen atoms, or
R 1 and R 2 , taken together with the carbon atom to which R 1 and R 2 are attached, form an optionally substituted alicyclic hydrocarbon group having 3 to 12 carbon atoms,
the method comprising bringing an organic substrate into contact with oxygen in the presence of a catalyst comprising the following compounds (A) and (C):
Compound (A): at least one compound selected from the group consisting of an inorganic peroxo acid, a salt of an inorganic peroxo acid, and an N-halogenated succinimide; and
Compound (C): a layered silicate;
wherein organic substrate is an amine having the following formula (I):

wherein R 1 and R 2 are each the same as defined above.

2. A method for producing an amide having the following formula (III):

wherein each of R 1 and R 2 is independently a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group, provided that not both R 1 and R 2 are hydrogen atoms, or
R 1 and R 2 , taken together with the nitrogen atom to which R 1 is attached, and the carbon atom to which R 2 is attached, form an optionally substituted alicyclic hydrocarbon group having 3 to 12 carbon atoms, the method comprising subjecting the oxime produced by the method according to claim 1 and having the above formula (II) to a Beckmann rearrangement reaction.

3. The method for producing an oxime according to claim 1 , wherein the layered silicate is smectite.

4. The method for producing an oxime according to claim 1 , wherein the layered silicate contains at least one member selected from the group consisting of hydrogen ion, ammonium ion, quaternary ammonium ions, cations of Group 4 metal elements, cations of Group 5 metal elements, cations of Group 6 metal elements, germanium ions, oxides of positively charged Group 4 metal elements, oxides of positively charged Group 5 metal elements, oxides of positively charged Group 6 metal elements, and positively charged germanium oxides.

5. The method for producing an oxime according to claim 1 , wherein the inorganic peroxo acid is at least one compound selected from the group consisting of a peroxomonosulfuric acid and a peroxodisulfuric acid, and the salt of the inorganic peroxo acid is at least one compound selected from the group consisting of a peroxomonosulfate and a peroxodisulfate.

Assignees

• Sumitomo Chemical Co

Inventors

• Hoshino Masahiro
• Kikuchi Yuta

Classifications

• C07C249/04

  of oximes · CPC title

• B01J31/0247

  Imides, amides or imidates (R-C=NR(OR)) · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• B01J21/16

  Clays or other mineral silicates · CPC title

• B01J23/462

  Ruthenium · CPC title