# US 10,246,392 B2 · Optimization of O-sulfonated phenol production for cumene hydroperoxide cleavage

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,246,392 B2
- Document ID: US10246392B2
- Status: Granted
- Kind: B2
- Application number: 15/501,186
- Filed: 2015-08-07
- Published: 2017-08-17
- Granted: 2019-04-02
- Earliest claimed: 2014-08-08
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Mark Erik Nelson; Arkady Samuilovich Dykman; Andrey Vladimirovich Zinenkov; Victor Vladimirovich Pinson; Dmitrij Nikolayevich Zhukov
- Web page: https://patentgrep.com/patent/US10246392B2

## CPC

- C07C 37/08: by decomposition of hydroperoxides, e.g. cumene hydroperoxide
- B01J 31/0225: {comprising sulfonic acid groups or the corresponding salts}
- C07C 37/20: using aldehydes or ketones
- C07C 45/53: of hydroperoxides
- C07C 303/06: by reaction with sulfuric acid or sulfur trioxide
- C07C 309/73: to carbon atoms of non-condensed six-membered aromatic rings
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method for the manufacture of a sulfonated phenol for use as a cumene hydroperoxide decomposition catalyst can comprise: combining phenol and a sulfonating agent at a first temperature that is 1° C. to 15° C. higher than a melting temperature of the phenol, to form a reaction mixture at the first temperature; reducing the first temperature of the reaction mixture to a second temperature that is 10 to 40° C. lower than the first temperature; and forming the sulfonated phenol at the second temperature.

## Claims

### Claim 1

A method for the cleavage of a C8-12 alkylbenzene hydroperoxide into phenol and a C3-6 ketone, comprising:
contacting the C8-12 alkylbenzene hydroperoxide with a catalytically sufficient amount of a sulfonated phenol under conditions effective to cleave the C8-12 alkylbenzene hydroperoxide to form the phenol, the C3-6 ketone, a C2-C6 alkylaldehyde, or a combination comprising at least one of the foregoing,
wherein the sulfonated phenol is manufactured by a method comprising
combining phenol and a sulfonating agent at a first temperature that is 1° C. to 15° C. higher than a melting temperature of the phenol, to form a reaction mixture at the first temperature,
reducing the first temperature of the reaction mixture to a second temperature that is 10 to 40° C. lower than the first temperature, and
forming the sulfonated phenol at the second temperature.

### Claim 2 (depends on 1)

The method of claim 1, wherein the catalytically sufficient amount is 10-500 ppm by weight.

### Claim 3 (depends on 1)

The method of claim 1, further comprising diluting the sulfonated phenol with the corresponding C8-12 alkyl benzene of the C8-12 alkylbenzene hydroperoxide before the contacting.

### Claim 4 (depends on 3)

The method of claim 3, further comprising maintaining a concentration of hydroxyacetone of less than or equal to 400 ppmw.

### Claim 5 (depends on 1)

The method of claim 1, wherein the C8-12 alkylbenzene comprises cumene and the C3-6 ketone comprises acetone.

### Claim 6 (depends on 1)

The method of claim 1, wherein the C8-12 alkylbenzene comprises ethyl benzene, and the alkylaldehyde comprises acetaldehyde.

### Claim 7 (depends on 1)

The method of claim 1, wherein the C8-12 alkylbenzene comprises sec-butyl benzene, and the C3-6 ketone is methyl ethyl ketone.

### Claim 8 (depends on 1)

The method of claim 1, wherein the C8-12 alkyl benzene is cyclohexyl benzene and the C3-6 ketone is cyclohexanone.

### Claim 9 (depends on 4)

The method of claim 4, where the concentration of hydroxyacetone is less than or equal to 300 ppmw.

### Claim 10 (depends on 1)

The method of claim 1, further comprising maintaining the second temperature over a time period of 1 hour to 20 hours.

### Claim 11 (depends on 1)

The method of claim 1, further comprising maintaining the second temperature over a time period of 3 hours to 8 hours.