IP Library Granted Patent US 8,247,616
Granted Patent B1
US 8,247,616 · App. 13/432,141 · Granted Aug 21, 2012

Method for the decomposition of cumene hydroperoxide

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Quick Facts
Patent No.
US 8,247,616
App. No.
13/432,141
Granted
Aug 21, 2012
Kind
B1
Abstract

A method of producing phenol, acetone and alpha-methyl styrene. A mixture of cumene hydroperoxide and dimethylbenzyl alcohol is provided. The mixture is subjected to a first stage reaction in the presence of about 0.5 to 1.5 wt. % water and about 20 to 400 ppm sulfuric acid at a reactor pressure of about 450 to 760 mm Hg, a temperature of about 60 to 85° C., and a residence time of 4 to 45 minutes to produce a composition having an acetone to phenol mole ratio of about 1 to 1.5. The composition is subjected to a second stage reaction in the presence of about 0.5 to 3 wt. % additional water with a second stage reactor temperature of about 110 to 150° C. and a residence time of 0.5 to 30 minutes.

Claims (13)

1. A method of producing phenol, acetone and alpha-methyl styrene, the method comprising the steps of:

providing a mixture of cumene hydroperoxide and dimethylbenzyl alcohol;

subjecting the mixture to a first stage reaction in the presence of about 0.5 to 1.5 wt. % water and about 20 to 400 ppm sulfuric acid at a reactor pressure of about 450 to 760 mm Hg, a temperature of about 60 to 85° C., and a residence time of 4 to 45 minutes to produce a composition having an acetone to phenol mole ratio of about 1 to 1.5; and

subjecting the composition to a second stage reaction in the presence of about 0.5 to 3 wt. % additional water with a second stage reactor temperature of about 110 to 150° C. and a residence time of 0.5 to 30 minutes.

2. The method of claim 1 , wherein the mixture is subjected to the first stage reaction at about 450 to 500 mm Hg operating pressure, about 78 to 80° C. operating temperature, a 5 to 6 minute residence time and in the presence of about 300 to 350 ppm sulfuric acid.

3. The method of claim 2 , wherein the mixture has a water content of about 1.0 to 1.2 wt. % while subjecting the mixture to the first stage reaction to produce a composition having an acetone to phenol mole ratio of about 1 to 1.2.

4. The method of claim 1 , wherein the composition is subjected to the second stage reaction with a residence time of 0.7 to 1.0 minutes, a temperature of about 120 to 140° C. and with about 1 to 2 wt. % additional water.

5. The method of claim 1 , wherein exit concentrations of dicumyl peroxide after the second stage reaction are maintained at about 0.01 to 0.15 wt. %.

6. The method of claim 1 , wherein exit concentrations of dicumyl peroxide after the second stage reaction are maintained at about 0.02 to 0.03 wt. %.

7. The method of claim 1 , wherein exit concentrations of dicumyl peroxide after the second stage reaction are maintained at about 0.06 to 0.10 wt. %.

8. The method of claim 1 , wherein the mixture is subjected to the first stage reaction at atmospheric to slightly negative pressure, a residence time of 15 to 45 minutes and in the presence of about 20 to 50 ppm sulfuric acid to produce a composition having an acetone to phenol ratio of about 1.0.

9. The method of claim 1 , wherein the composition is subjected to the second stage reaction with a residence time of 5 to 20 minutes, a temperature of about 120 to 140° C. and about 1 to 2 wt. % additional water.

10. The method of claim 1 , wherein the temperature while subjecting the composition to the second stage reaction is about 134 to 138° C.

Assignments (5)
SECURITY INTEREST Recorded Oct 27, 2021
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: TRUIST BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 057940/0794 →
RELEASE OF SECURITY INTEREST Recorded Oct 27, 2021
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 057941/0536 →
SECURITY INTEREST Recorded Oct 17, 2016
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 040382/0909 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 13, 2016
From: HONEYWELL INTERNATIONAL INC.
To: ADVANSIX RESINS & CHEMICALS LLC
Reel/Frame 040337/0820 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2012
From: KEENAN, SCOTT ROY; HAGANS, MICHAEL KEITH
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 029170/0872 →