IP Library Granted Patent US 8,030,525
Granted Patent B2
US 8,030,525 · App. 12/578,307 · Granted Oct 4, 2011

Method for producing phenol and acetone

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Quick Facts
Patent No.
US 8,030,525
App. No.
12/578,307
Granted
Oct 4, 2011
Kind
B2
Abstract

A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, the method comprising the steps of a) reacting the cumene hydroperoxide mixture with a 2-hydroxybenzenesulfonic acid catalyst having a concentration of 0.1 to 1 mmol/L acid catalyst to form a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage and decomposing the second mixture in a second stage to produce a third mixture comprising phenol and acetone.

Claims (21)

1. A method for producing phenol and acetone in a multi-state process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, the method comprising the steps of:

(a) reacting the cumene hydroperoxide mixture with a 2-hydroxybenzenesulfonic acid catalyst having a concentration of 0.1 to 1 mmol/L acid catalyst to form a second mixture comprising phenol, acetone and dicumyl peroxide in a first state, wherein the 2-hydroxybenzenesulfonic acid catalyst is selected from the group consisting of 2-hydroxy-5-cumyl-benzenesulfonic acid, 3,3′-propane-2,2-diyl-bis-(6-hydroxybenzenesulfonic) acid, 2-hydroxy-5-chlorobenzenesulfonic acid, 2-hydroxy-5-methoxybenzenesulfonic acid, 2-hydroxy-5-methylbenzenesulfonic acid, 2-hydroxy-4-t-butyl-benzenesulfonic acid and 2-hydroxybenzenesulfonic acid, and

(b) decomposing the second mixture in a second stage to produce a third mixture comprising phenol and acetone.

2. The method of claim 1 , wherein the reacting in the first stage is at a temperature of from 40 to 75° C., and the decomposing in the second state is at a temperature of from 110 to 140° C.

3. The method of claim 1 , wherein the step of reacting the cumene hydroperoxide is in at least two serially connected reactors.

4. The method of claim 1 , wherein the cumene hydroperoxide concentration is from about 50 to 92 mass %.

5. The method of claim 1 , wherein the cumene hydroperoxide concentration is from about 80 to 84 mass %.

6. The method of claim 1 , wherein the second mixture is not quenched with an alkaline material prior to step b).

7. The method of claim 1 , wherein the third mixture has a hydroxyacetone concentration of less than 0.10 mass %, based on the total mass % of the third mixture.

8. The method of claim 1 , wherein the third mixture has a hydroxyacetone concentration of less than 0.05 mass %, based on the total mass % of the third mixture.

9. A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, the method comprising the steps of:

(a) reacting the cumene hydroperoxide mixture with a 2-hydroxybenzenesulfonic acid catalyst having a concentration of 0.1 to 1 mmol/L acid catalyst to form a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage, wherein the 2-hydroxybenzenesulfonic acid catalyst is selected from the group consisting of 2-hydroxy-5-cumyl-benzenesulfonic acid, 3,3′-propane-2,2-diyl-bis-(6-hydroxybenzenesulfonic) acid, 2-hydroxy-5-chlorobenzenesulfonic acid, 2-hydroxy-5-methoxybenzenesulfonic acid, 2-hydroxy-5-methylbenzenesulfonic acid and 2-hydroxybenzenesulfonic acid, and

(b) decomposing the second mixture in a second stage to produce a third mixture comprising phenol and acetone.

10. The method of claim 9 , wherein the third mixture has a hydroxyacetone concentration of less than 0.10 mass %, based on the total mass % of the third mixture.

11. The method of claim 9 , wherein the second mixture is not quenched with an alkaline material prior to step b).

12. A method for producing phenol and acetone in a multi-stage process at an elevated temperature from a cumene hydroperoxide mixture comprising cumene, the method comprising the steps of:

(a) reacting the cumene hydroperoxide mixture with a 2-hydroxybenzenesulfonic acid catalyst having a concentration of 0.1 to 1 mmol/L acid catalyst to form a second mixture comprising phenol, acetone and dicumyl peroxide in a first stage, wherein the 2-hydroxybenzenesulfonic acid catalyst is selected from the group consisting of 2-hydroxy-5-cumyl-benzenesulfonic acid, 3,3′-propane-2,2-diyl-bis-(6-hydroxybenzenesulfonic) acid, 2-hydroxy-5-chlorobenzenesulfonic acid, 2-hydroxy-5-methoxybenzenesulfonic acid and 2-hydroxy-5-methylbenzenesulfonic acid, and

(b) decomposing the second mixture in a second stage to produce a third mixture comprising phenol and acetone.

13. The method of claim 12 , wherein the third mixture has a hydroxyacetone concentration of less than 0.10 mass %, based on the total mass % of the third mixture.

14. The method of claim 12 , wherein the third mixture has a hydroxyacetone concentration of less than 0.05 mass %, based on the total mass % of the third mixture.

15. The method of claim 12 , wherein the second mixture is not quenched with an alkaline material prior to step b).

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Mar 17, 2014
From: CITIBANK, N.A.
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 032459/0798 →
SECURITY AGREEMENT Recorded Mar 1, 2010
From: SABIC INNOVATIVE PLASTICS IP B.V.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 024005/0462 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 13, 2009
From: NELSON, MARK E.; DYKMAN, ARKADY SAMUILOVICH; ZINENKOV, ANDREY VLADIMIROVICH; PINSON, VICTOR VLADIMIROVICH; GREBENSHCHIKOV, ILJA NIKOLAYEVICH; ZHUKOV, DMITRIJ NIKOLAYEVICH
To: SABIC INNOVATIVE PLASTICS IP B.V.
Reel/Frame 023365/0642 →