Method for controlling cleavage of hydroperoxides of alkylaromatic hydrocarbons

Patent metadata

Field	Value
Publication number	US-10017440-B2
Application number	US-201515501188-A
Country	US
Kind code	B2
Filing date	Aug 6, 2015
Priority date	Aug 8, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

A method of producing phenol and acetone can include: alkylating benzene with a C2-6 alkyl source in the presence of a zeolite catalyst to produce a C8-12 alkylbenzene; oxidizing the C8-12 alkylbenzene in the presence of an oxygen containing gas to produce a C8-12 alkylbenzene hydroperoxide; cleaving decomposing the C8-12 alkylbenzene hydroperoxide in the presence of an acid catalyst to produce phenol, a C3-6 ketone, and undesirable side products such as, but not limited to acetaldehyde, DMBA, acetophenone, AMS, AMS dimers, unidentified heavies, or a combination including at least one of the foregoing; and monitoring a concentration of the C8-12 alkylbenzene hydroperoxide in a process stream of a reactor in real time at a temperature and a pressure of the process stream; and in real time, controlling a parameter of the reactor and/or the cleaving decomposing in response to the concentration of the C8-12 alkylbenzene hydroperoxide.

First claim

We claim:

1. A method of producing phenol and a C 3-6 ketone, comprising:
alkylating benzene with a C 2-6 alkyl source in the presence of a zeolite catalyst to produce a C 8-12 alkylbenzene;
oxidizing the C 8-12 alkylbenzene in the presence of an oxygen containing gas to produce a C 8-12 alkylbenzene hydroperoxide;
decomposing the C 8-12 alkylbenzene hydroperoxide in the presence of an acid catalyst to produce phenol, a C 3-6 ketone, or a combination comprising at least one of the foregoing;
monitoring a concentration of the C 8-12 alkylbenzene hydroperoxide in a process stream of a reactor in real time at a temperature and a pressure of the process stream; and
in real time, controlling a parameter of the reactor and/or the decomposing in response to the concentration of the C 8-12 alkylbenzene hydroperoxide, wherein the parameter is a flow rate of the process stream, a pressure of the process stream, a pressure of the reactor, the concentration of the C 8-12 alkylbenzene hydroperoxide, a concentration of the cleavage catalyst, a concentration of an oxidation catalyst, a concentration of the C 8-12 alkylbenzene, a concentration of water, a concentration of ammonia, or a combination of at least one of the foregoing.

2. The method of claim 1 , wherein decomposing is ammonia free.

3. The method of claim 1 , wherein the monitoring occurs before decomposing the C 8-12 alkylbenzene hydroperoxide, after decomposing the C 8-12 alkylbenzene hydroperoxide, or both before and after decomposing the C 8-12 alkylbenzene hydroperoxide.

4. The method of any of claim 1 , wherein the monitoring comprises using a near infrared probe located downstream of at least a portion of the decomposing.

5. The method of claim 1 , wherein monitoring further comprises immersing a portion of a probe coupled to a spectrometer into the process stream having a flow direction; and further comprising orienting an optical path of the probe to an angle of 85 degrees to 95 degrees relative to the flow direction.

6. A method of producing phenol and a C 3-6 ketone from a C 8-12 alkylbenzene hydroperoxide in a process stream of a reactor, the method comprising:
immersing a portion of a probe coupled to a spectrometer into the process stream comprising a flow direction, a temperature, and a pressure;
monitoring absorption data with the spectrometer in the range from 900 nm to 2500 nm in real time;
calculating a concentration of the C 8-12 alkylbenzene hydroperoxide in the reaction stream from the absorption data, and
controlling a parameter of the reactor or the reaction stream in response to the calculated concentration, wherein the parameter is a flow rate of the process stream, a pressure of the process stream, a pressure of the reactor, the concentration of the C 8-12 alkylbenzene hydroperoxide, a concentration of the cleavage catalyst, a concentration of an oxidation catalyst, a concentration of the C 8-12 alkylbenzene, a concentration of water, a concentration of ammonia, or a combination of at least one of the foregoing.

7. The method of claim 6 , wherein the monitoring of absorption data is in the range from 1100 to 2200 nm.

8. The method of claim 1 , wherein the monitoring in real time comprises sampling at a sample rate of greater than or equal to 1 sample per minute.

9. The method of claim 1 , further comprising adjusting the catalyst activity in the process stream; wherein adjusting the catalyst activity consists of adjusting an inlet flow rate to the reactor of water, acetone, acid catalyst, or a combination comprising at least one of the foregoing.

10. The method of claim 1 , wherein the parameter is a concentration of water and wherein the concentration of water is controlled such that a temperature of the reaction mixture is maintained from 45° C. and 65° C.

11. The method of claim 1 , wherein the controlling the parameter of the reactor comprises comparing the concentration to a chemometric model, and wherein the chemometric model had been formed by monitoring concentration using ultra-pressure liquid chromatography.

12. The method of claim 1 , further comprising developing a temperature compensating chemometric model; and controlling the parameter of the reactor further comprises comparing the concentration of the C 8-12 alkylbenzene hydroperoxide to the temperature compensating chemometric model.

13. The method of claim 1 , further comprising monitoring the concentration of di(C 8-12 alkylbenzyl) peroxide, water, acetone, phenol, hydroperoxide, dimethylbenzyl alcohol, C 8-12 alkylbenzene, α-methylstyrene or a combination comprising at least one of the foregoing.

14. A method for the manufacture of bisphenol A, comprising reacting the phenol and/or C 3-6 ketone produced by the method of claim 1 in the presence of a catalyst to form bisphenol A.

15. A process for the production of polycarbonate, comprising contacting the bisphenol A of claim 14 with a carbonyl source in the presence of a catalyst and under polycarbonate-forming conditions, to produce the polycarbonate.

16. A reactor comprising:
a reaction vessel comprising an inlet conduit directing an inlet stream, an outlet conduit directing an outlet stream;
a probe inserted into one of the inlet conduit, the reaction vessel, and the outlet conduit, wherein the probe is coupled to a spectrometer and is configured to measure the concentration of a C 8-12 alkylbenzene hydroperoxide, a di(C 8-12 alkylbenzyl) peroxide, water, acetone, phenol, hydroperoxide, dimethylbenzyl alcohol, acetaldehyde, a C 3-6 ketone, a C 8-12 alkylbenzene, α-methylstyrene, or a combination comprising at least one of the foregoing; and
a distributed control system in electrical communication with the probe and a control device, wherein the control device is configured to control a flow rate of the inlet stream, a temperature of the inlet stream, a pressure of the inlet stream, the temperature of the reaction vessel, the pressure of the reaction vessel, or a combination comprising at least one of the foregoing.

17. The reactor of claim 16 , comprising two or more reaction vessels where the reaction vessels are connected in fluid communication in a serial flow arrangement and wherein the probe is located in the outlet conduit downstream of a last reaction vessel.

18. The reactor of claim 16 , wherein the reactor is capable of achieving a conversion of the dimethylbenzyl alcohol to α-methylstyrene of greater than or equal to 80%.

19. The reactor of claim 16 , further comprising a catalyst activity balancing system for adjusting the catalytic activity of a reaction mixture, and wherein the catalyst activity balancing system is free of ammonia.

20. The reactor of claim 16 , wherein the probe is retractable.

Assignees

• Sabic Global Technologies Bv

Inventors

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

Classifications

• C08G64/38

  using other monomers · CPC title

• C07C2529/06

  Crystalline aluminosilicate zeolites; Isomorphous compounds thereof · CPC title

• C07C407/00

  Preparation of peroxy compounds · CPC title

• C07C37/08 Primary

  by decomposition of hydroperoxides, e.g. cumene hydroperoxide · CPC title

• B01J2219/24

  Stationary reactors without moving elements inside · CPC title