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Method for the decomposition of cumene hydroperoxide

a technology of cumene hydroperoxide and cumene hydroperoxide, which is applied in the field of cumene hydroperoxide decomposition, can solve the problems of increasing complexity in both equipment count and control, reducing the yield of cumene hydroperoxide, so as to maximize the yield of dicumyl peroxide and minimize residual dicumyl peroxide , the effect of maximizing the overall di

Active Publication Date: 2012-08-02
ADVANSIX RESINS & CHEM LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This approach significantly increases the yield of alpha-methyl styrene while reducing dicumyl peroxide residuals, improving product quality and simplifying the purification process, as validated in commercial units with improved yield and reduced equipment complexity.

Problems solved by technology

All of these approaches have plusses and minuses, typically requiring recycling of significant amounts of product material back to this part of the process, higher levels of acid catalyst (thus requiring more base to neutralize the reaction product prior to distillation) and / or additional complexity in both equipment count and control, for what in most cases is a marginal gain in selectivity over commonly practiced optimized approaches.
Many approaches do not consider potential detrimental downstream impacts in terms of yield, energy, product quality and equipment count / complexity.
However, since DMBA, water and AMS are in equilibrium in the second stage, it was expected that the DMBA concentrations would be significantly higher at the same optimum DCP range, resulting in a slight yield penalty.

Method used

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  • Method for the decomposition of cumene hydroperoxide

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0013]The results in FIG. 1 were generated using a well stirred glass reactor that was charged with 15 ml of a solution of 1 / 1 molar phenol / acetone spiked with approximately 8.2% DCP, 1.3% DMBA, 1.4% AMS, 12% cumene, and sufficient water added to give either 1.3% or 3.3% water content. The solution was brought to target temperature, and 8 μL of 0.5 molar sulfuric acid added (approximately 25 ppm in the bulk reaction) to start the reaction. Samples were taken at various times, neutralized with a small amount of base, and analyzed for a complete component profile.

example 2

[0014]A CRP-containing stream with 80% CRP, 3.6% DMBA, 0.4% acetophenone (AP), and the residual cumene, was fed to the back mixed first stage of a commercial CRP decomposer operating under conditions of vigorous boiling at 550-600 mm Hg pressure, 78-80° C., a 1.25-1.35 mole ratio of acetone to CRP, 5-6 minute residence time, 300-350 ppm of sulfuric acid, and 1.0-1.3 wt. % water under optimum conditions. With no additional water added ahead of a plug flow second stage with 0.8-1.0 minutes of residence time, an average AMS yield of 80.8% was obtained at 108 C, with 0.09 to 0.12 wt. % DCP, and 0.16 to 0.18% DMBA residuals exiting the second stage.

example 3

[0015]Conditions were as in example 2 with 1.5 wt. % additional water added ahead of the second stage. An optimal average AMS yield of 82.1% was obtained at 122° C. with 0.02 to 0.04% DCP, and 0.16 to 0.18 wt. % DMBA exiting the second stage.

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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.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation of U.S. patent application Ser. No. 12 / 797,321, filed Jun. 9, 2010, which is incorporated by reference in its entirety.FIELD OF THE INVENTION[0002]The present invention relates to an improved method for the production of phenol, acetone and alpha-methyl styrene (AMS) from a cumene hydroperoxide and dimethylbenzyl alcohol (DMBA) mixture.DESCRIPTION OF RELATED ART[0003]The dominant method for producing phenol and acetone is via air oxidation of cumene to cumene hydroperoxide (CHP), followed by acid catalyzed decomposition of the CHP selectively to phenol and acetone. Dimethylbenzyl alcohol (DMBA) is formed as the principal side product in the oxidation step, and is subsequently dehydrated to alpha-methyl styrene (AMS) in the same acid catalyzed decomposition step.[0004]The acid catalyzed decomposition of CHP is well known, most modem processes utilizing a two step, continuous flow approach to optimize over...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C27/00
CPCC07C1/24C07C37/08C07C45/53C07C2527/054C07C39/04C07C49/08C07C15/44Y02P20/52C07C27/00
Inventor KEENAN, SCOTT ROYHAGANS, MICHAEL KEITH
Owner ADVANSIX RESINS & CHEM LLC