Optimization of O-sulfonated phenol production for cumene hydroperoxide cleavage

Patent metadata

Field	Value
Publication number	US-10745333-B2
Application number	US-201916268042-A
Country	US
Kind code	B2
Filing date	Feb 5, 2019
Priority date	Aug 8, 2014
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

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.

First claim

The invention claimed is:

1. A method for the manufacture of a sulfonated phenol for use as a cumene hydroperoxide decomposition catalyst, 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.

2. The method of claim 1 , wherein the phenol and the sulfonating agent are combined in a molar ratio of 50:1 to 1:3.

3. The method of claim 1 , wherein the sulfonating agent comprises sulfuric acid, acetyl sulfate, sulfur trioxide, fuming sulfuric acid, or a combination comprising at least one of the foregoing.

4. The method of claim 1 , wherein the combining comprises adding the sulfonating agent to the phenol.

5. The method of claim 1 , comprising forming o-sulfonated phenol and p-sulfonated phenol in a weight ratio of o-sulfonated phenol to p-sulfonated phenol greater than or equal to 1.

6. The method of claim 1 , further comprising maintaining the second temperature over a time period of 0.5 hours to 100 hours.

7. The method of claim 1 , wherein the combining is in a first reactor zone, the reducing the first temperature is in a second reactor zone, and the forming is in a third reactor zone.

8. The method of claim 7 , where the second reactor zone is smaller in volume than the third reactor zone and imparts a residence time of approximately 0.01-0.2 hours, and wherein the residence time is less than or equal to 1% of a total reaction time.

9. The method of claim 1 , wherein the method is conducted in a plug-flow reactor.

10. A sulfonated phenol formed by the method of claim 1 , comprising o-sulfonated phenol and p-sulfonated phenol in a weight ratio of o-sulfonated phenol to p-sulfonated phenol greater than or equal to 1.

Assignees

• Sabic Global Technologies Bv

Inventors

• Nelson Mark Erik
• Dykman Arkady Samuilovich
• Zinenkov Andrey Vladimirovich
• Pinson Victor Vladimirovich
• Zhukov Dmitrij Nikolayevich

Classifications

• C07C309/42

  having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings · CPC title

• C07C303/06 Primary

  by reaction with sulfuric acid or sulfur trioxide · CPC title

• C07C49/08

  Acetone · CPC title

• C07C45/86

  Use of additives, e.g. for stabilisation · CPC title

• C07C45/53

  of hydroperoxides · CPC title