# US 2017/0282172 A1 · Oxidation reactor and process for producing oxide

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- Number: US 2017/0282172 A1
- Document ID: US20170282172A1
- Status: Published application
- Kind: A1
- Application number: 15/507,147
- Filed: 2015-08-07
- Published: 2017-10-05
- Earliest claimed: 2014-08-29
- Assignees: Osaka Prefecture University Public Corporation; Daicel Corporation
- Applicants: Osaka Prefecture University Public Corporation; Daicel Corporation
- Inventors: Akinori MUTO; Yoshiyuki MURAI; Takamasa SUZUKI; Ichiro TAKASE
- Web page: https://patentgrep.com/patent/US20170282172A1

## CPC

- B01J 23/75: Cobalt
- B01J 8/001: {Controlling catalytic processes (B01J8/1809 takes precedence)}
- B01J 8/0085: {promoting uninterrupted fluid flow, e.g. by filtering out particles in front of the catalyst layer}
- B01J 8/1827: {the fluidising gas being a reactant}
- B01J 8/22: gas being introduced into the liquid
- B01J 19/0053: {Details of the reactor}
- B01J 35/00: Catalysts, in general, characterised by their form or physical properties
- B01J 37/0207: {Pretreatment of the support}
- C07C 27/16: with other oxidising agents
- C07C 29/48: by oxidation reactions with formation of hydroxy groups
- C07C 31/125: containing five to twenty-two carbon atoms
- C07C 45/40: by oxidation with ozone; by ozonolysis
- C07C 49/04: Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C 51/34: by oxidation with ozone; by hydrolysis of ozonides
- C07C 53/126: Acids containing more than four carbon atoms
- B01F 23/20: Mixing gases with liquids
- B01F 33/00: Other mixers; Mixing plants; Combinations of mixers
- C07B 61/00: Other general methods
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01F: MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING (mixing paints B44D3/06)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

Provided is an oxidation reactor capable of oxidizing hydrocarbons with both reaction efficiency and energy efficiency. The oxidation reactor according to the present invention includes a liquid inlet channel, a gas inlet channel, a gas-liquid mixing unit, and a flow reactor. Through the liquid inlet channel, a liquid containing a reaction substrate hydrocarbon is introduced. Through the gas inlet channel, a gas containing oxygen and ozone is introduced. The gas-liquid mixing unit mixes the liquid introduced from the liquid inlet channel with the gas introduced from the gas inlet channel. In the flow reactor, an oxidation catalyst is immobilized or packed. The gas-liquid mixing unit houses, in its channel, a mobile particle which is capable of rotating and/or moving to mix the liquid with the gas to thereby form a gas-liquid slug flow. The gas-liquid slug flow is introduced into the flow reactor.

## Claims

### Claim 1

An oxidation reactor comprising:
a liquid inlet channel through which a liquid containing a reaction substrate hydrocarbon is introduced;
a gas inlet channel through which a gas containing oxygen and ozone is introduced;
a gas-liquid mixing unit that mixes the liquid introduced from the liquid inlet channel with the gas introduced from the gas inlet channel;
a flow reactor to or in which an oxidation catalyst is immobilized or packed; and
a mobile particle disposed in a channel of the gas-liquid mixing unit, the mobile particle capable of rotating and/or moving to mix the liquid with the gas to thereby form a gas-liquid slug flow, the gas-liquid slug flow being introduced into the flow reactor.

### Claim 2 (depends on 1)

The oxidation reactor according to claim 1, further comprising
a gas-liquid separator downstream from the flow reactor.

### Claim 3 (depends on 2)

The oxidation reactor according to claim 2, further comprising
a circulation channel through which at least part of a liquid separated in the gas-liquid separator is recycled to the gas-liquid mixing unit or to an upstream portion from the gas-liquid separator.

### Claim 4 (depends on 2)

The oxidation reactor according to claim 2, further comprising
a circulation channel through which at least part of a gas separated in the gas-liquid separator is recycled to the gas-liquid mixing unit or to an upstream portion from the gas-liquid mixing unit.

### Claim 5 (depends on 1)

The oxidation reactor according to claim 1,
wherein the oxidation catalyst is a catalyst comprising
a transition metal in an form of an elementary substance, a compound, or an ion; and
an inorganic support onto which the transition metal is supported or immobilized.

### Claim 6 (depends on 1)

The oxidation reactor according to claim 1,
wherein the oxidation catalyst is selected from:
a catalyst comprising:
a transition metal compound; and
a support having a Hammett acidity function (H0) of −9 or less and supporting the transition metal compound; and
a catalyst comprising:
a transition metal ion; and
a support having a Hammett acidity function (H0) of −9 or less and being ion-exchanged with the transition metal ion.

### Claim 7 (depends on 6)

The oxidation reactor according to claim 6,
wherein the support comprises a strongly acidic or super acidic ion exchange resin.

### Claim 8 (depends on 1)

The oxidation reactor according to claim 1,
wherein the flow reactor comprises
a coating disposed on an inner wall of the flow reactor, the coating comprising:
a transition metal ion; and
a strongly acidic or super acidic ion exchange resin being ion-exchanged with the transition metal ion.

### Claim 9 (depends on 1)

The oxidation reactor according to claim 1, further comprising
an imide compound inlet channel upstream from the flow reactor, where an imide compound having a cyclic imide skeleton is introduced from the imide compound inlet channel.

### Claim 10 (depends on 1)

A method for producing an oxide, the method comprising
oxidizing a hydrocarbon in coexistence of oxygen and ozone using the oxidation reactor according to claim 1, to yield a corresponding oxide or oxides.

### Claim 11 (depends on 3)

The oxidation reactor according to claim 3, further comprising
a circulation channel through which at least part of a gas separated in the gas-liquid separator is recycled to the gas-liquid mixing unit or to an upstream portion from the gas-liquid mixing unit.

### Claim 12 (depends on 2)

The oxidation reactor according to claim 2,
wherein the oxidation catalyst is a catalyst comprising
a transition metal in an form of an elementary substance, a compound, or an ion; and
an inorganic support onto which the transition metal is supported or immobilized.

### Claim 13 (depends on 3)

The oxidation reactor according to claim 3,
wherein the oxidation catalyst is a catalyst comprising
a transition metal in an form of an elementary substance, a compound, or an ion; and
an inorganic support onto which the transition metal is supported or immobilized.

### Claim 14 (depends on 4)

The oxidation reactor according to claim 4,
wherein the oxidation catalyst is a catalyst comprising
a transition metal in an form of an elementary substance, a compound, or an ion; and
an inorganic support onto which the transition metal is supported or immobilized.

### Claim 15 (depends on 2)

The oxidation reactor according to claim 2,
wherein the oxidation catalyst is selected from:
a catalyst comprising:
a transition metal compound; and
a support having a Hammett acidity function (H0) of −9 or less and supporting the transition metal compound; and
a catalyst comprising:
a transition metal ion; and
a support having a Hammett acidity function (H0) of −9 or less and being ion-exchanged with the transition metal ion.

### Claim 16 (depends on 3)

The oxidation reactor according to claim 3,
wherein the oxidation catalyst is selected from:
a catalyst comprising:
a transition metal compound; and
a support having a Hammett acidity function (H0) of −9 or less and supporting the transition metal compound; and
a catalyst comprising:
a transition metal ion; and
a support having a Hammett acidity function (H0) of −9 or less and being ion-exchanged with the transition metal ion.

### Claim 17 (depends on 4)

The oxidation reactor according to claim 4,
wherein the oxidation catalyst is selected from:
a catalyst comprising:
a transition metal compound; and
a support having a Hammett acidity function (H0) of −9 or less and supporting the transition metal compound; and
a catalyst comprising:
a transition metal ion; and
a support having a Hammett acidity function (H0) of −9 or less and being ion-exchanged with the transition metal ion.

### Claim 18 (depends on 2)

The oxidation reactor according to claim 2,
wherein the flow reactor comprises
a coating disposed on an inner wall of the flow reactor, the coating comprising:
a transition metal ion; and
a strongly acidic or super acidic ion exchange resin being ion-exchanged with the transition metal ion.

### Claim 19 (depends on 3)

The oxidation reactor according to claim 3,
wherein the flow reactor comprises
a coating disposed on an inner wall of the flow reactor, the coating comprising:
a transition metal ion; and
a strongly acidic or super acidic ion exchange resin being ion-exchanged with the transition metal ion.

### Claim 20 (depends on 4)

The oxidation reactor according to claim 4,
wherein the flow reactor comprises
a coating disposed on an inner wall of the flow reactor, the coating comprising:
a transition metal ion; and
a strongly acidic or super acidic ion exchange resin being ion-exchanged with the transition metal ion.
