Alkylbenzene hydroperoxide production using dispersed bubbles of oxygen containing gas

Patent metadata

Field	Value
Publication number	US-10017467-B2
Application number	US-201515501187-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Aug 8, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

An apparatus for oxidation of a C 8 -C 12 alkylbenzene reactant to a C 8 -C 12 alkylbenzene hydroperoxide product, the re-actor can comprise: a flow reactor comprising a reactant inlet, an oxidate product outlet, wherein the reactor is configured to provide a liquid flow from the reactant inlet to the product outlet, a gas inlet configured to introduce an oxygen-containing gas into the reactor, and an inlet sparger configured to flow gas bubbles comprising the oxygen-containing gas within the liquid flow, and wherein: the inlet sparger is configured to flow the gas bubbles having a diameter of 1.0 mm to 5.0 mm over a gas bubble residence time from 1 to 200 seconds, and/or the inlet sparger configured to flow the gas bubbles such that greater than or equal to 80% of the gas bubbles do not coalesce into larger bubbles over a gas bubble residence time of 1 to 200 seconds.

First claim

We claim:

1. A reactor for oxidation of a C 8 -C 12 alkylbenzene reactant to a C 8 -C 12 alkylbenzene hydroperoxide product, the apparatus comprising:
a flow reactor comprising
a reactant inlet,
an oxidate product outlet, wherein the flow reactor is configured to provide a liquid flow from the reactant inlet to the oxidate product outlet,
a gas inlet configured to introduce an oxygen-containing gas into the flow reactor,
an inlet sparger configured to flow gas bubbles comprising the oxygen-containing gas within the liquid flow, and
a reaction channel, wherein, in use, the liquid flow from the reactant inlet to the oxidate product outlet is through a reaction channel, and

wherein the inlet sparger has a single aperture configured to flow gas bubbles one at a time, serially, into the reaction channel.

2. The reactor of claim 1 wherein:
the inlet sparger is configured to flow the gas bubbles having a diameter of 1.0 mm to 5.0 mm over a gas bubble residence time from 1 to 200 seconds, and/or
the inlet sparger configured to flow the gas bubbles such that greater than or equal to 80% of the gas bubbles do not coalesce into larger bubbles over a gas bubble residence time of 1 to 200 seconds.

3. The reactor of claim 2 , wherein the inlet sparger is configured to flow the gas bubbles having a diameter of 1 to 5.0 mm over a gas bubble residence time of 1 to 150 seconds.

4. The reactor of claim 2 , wherein the inlet sparger configured to distribute gas bubbles such that greater than or equal to 90% of the gas bubbles do not coalesce into larger bubbles over the gas bubble residence time.

5. The reactor of claim 2 , further comprising an enricher configured to increase the oxygen levels in the oxygen-containing gas to greater than or equal to 30 volume % on a dry basis.

6. The reactor of claim 2 , further comprising a pH control medium supply in fluid communication with the reactant inlet, and wherein the pH control medium supply comprises at least one of sodium carbonate, ammonia, and ammonium carbonate.

7. The reactor of claim 2 , wherein the gas inlet is located to provide a flow of the gas bubbles to the flow reactor, wherein the gas bubbles are introduced into the flow reactor in a direction across a liquid flow direction and wherein the gas bubbles flow through the flow reactor in a direction coaxial with the liquid flow.

8. The reactor of claim 2 , wherein the reaction channel has a diameter of greater than or equal to 6 mm.

9. The reactor of claim 2 , wherein the inlet sparger comprises an array of sparger channels, wherein each sparger channel has a diameter of 0.01 to 0.9 mm.

10. The reactor of claim 2 , wherein the flow reactor further comprises a gas outlet comprising an oxygen sensor and/or a temperature sensor, and wherein the flow reactor further comprises a control system, wherein input signals to the control system comprise signals from the oxygen sensor and the temperature sensor, and wherein the control system is configured to control an air compressor.

11. A process for the continuous production of a C 8 -C 12 alkylbenzene hydroperoxide, comprising:
introducing a liquid flow comprising C 8 -C 12 alkylbenzene through a reactant inlet to a reaction channel in the reactor of claim 2 ;
introducing gas bubbles to the reaction channel, wherein the gas bubbles have a diameter of 1.0 mm to 5.0 mm over a gas bubble residence time from 1 to 200 seconds, and/or wherein greater than or equal to 80% of the gas bubbles do not coalesce into larger bubbles over the gas bubble residence time of 1 to 200 seconds; and
oxidizing the C 8 -C 12 alkylbenzene to produce a liquid oxidate product comprising the C 8 -C 12 alkylbenzene hydroperoxide.

12. A process for the continuous production of a C 8 -C 12 alkylbenzene hydroperoxide, comprising:
introducing a liquid flow comprising C 8 -C 12 alkylbenzene through a reactant inlet to a reaction channel in the reactor of claim 1 ;
introducing gas bubbles, one at a time, serially, to the reaction channel through a single aperture in an inlet sparger; and
oxidizing the C 8 -C 12 alkylbenzene to produce a liquid oxidate product comprising the C 8 -C 12 alkylbenzene hydroperoxide.

13. The process of claim 11 , wherein the C 8 -C 12 alkylbenzene is cumene and the C 8 -C 12 alkylbenzene hydroperoxide is cumene hydroperoxide, and/or wherein the liquid oxidate product further comprises dimethylbenzyl alcohol and acetophenone.

14. The process of claim 11 , further comprising controlling a pH value of the reaction mixture from 4 to 10 by adding at least one of sodium carbonate or ammonia, or ammonium carbonate.

15. The process of claim 11 ,
wherein the oxidizing is at a reactor pressure of 0 kPa(g) to 1,400 kPa(g), and/or
wherein the oxidizing is at a temperature of 70° C. to 130° C.

16. The process of claim 11 , wherein the C 8-12 alkylbenzene is sec-butyl benzene and the C 8-12 alkylbenzene hydroperoxide is sec-butyl benzene hydroperoxide.

17. The process of claim 11 , comprising maintaining a gas outlet oxygen concentration of greater than or equal to 2 vol. % wet.

18. The process of claim 11 , comprising maintaining a temperature of the flow reactor of 175° C. to 225° C., and wherein the temperature comprises a gas outlet temperature of the flow reactor, an oxidate product outlet temperature of the flow reactor, or a combination comprising at least one of the foregoing.

19. The process of claim 11 , adjusting a temperature of the flow reactor in response to a gas outlet oxygen concentration, wherein the temperature comprises a gas outlet temperature of the flow reactor, an oxidate product outlet temperature of the flow reactor, or a combination comprising at least one of the foregoing.

20. A process for producing phenol and acetone, comprising
oxidizing the C 8-12 alkylbenzene of claim 11 in the presence of an oxygen-containing gas to produce a C 8-12 alkylbenzene hydroperoxide; and
cleaving the C 8-12 alkylbenzene hydroperoxide in the presence of an acid catalyst to produce phenol and a acetaldehyde, a C 2-6 ketone, or a combination comprising at least one of the foregoing.

21. The process of claim 19 , wherein adjusting comprises decreasing the temperature if the gas outlet oxygen concentration is less than or equal to 3.5vol. % wet; increasing the temperature if the gas outlet oxygen concentration is greater than or equal to 3.5 vol. % wet, or a combination comprising at least one of the forgoing.

Assignees

• Sabic Global Technologies Bv

Inventors

• Nelson Mark Erik
• Zinenkov Andrey Vladimirovich
• Dykman Arkady Samuilovich

Classifications

• B01J10/002

  carried out in foam, aerosol or bubbles · CPC title

• B01J19/248

  Reactors comprising multiple separated flow channels · CPC title

• B01J19/0006

  Controlling or regulating processes (controlling or regulating in general G05) · CPC title

• C07C407/00 Primary

  Preparation of peroxy compounds · CPC title

• B01J2219/00177

  controlling the pH · CPC title