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

Inactive Publication Date: 2011-12-15
HONEYWELL INT INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0008]The present invention relates to a method for the production of phenol, acetone, and alpha-methyl styrene from a mixture of cumene hydroperoxide and dimethylbenzyl alcohol wherein the first stage is carried out with an acetone to phenol mole ratio of 1.0-1.5, water content of 0.5 to 1.5 wt. %, sulfuric acid concentration of 20-400 ppm, a reactor pressure of 500-760 mmHg, and a temperature of 60-85° C., being optimized to maximize the yield of dicumyl peroxide from

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 co

Method used

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  • Method for the decomposition of cumene hydroperoxide

Examples

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example 1

[0012]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

[0013]A CHP-containing stream with 80% CHP, 3.6% DMBA, 0.4% acetophenone (AP), and the residual cumene, was fed to the back mixed first stage of a commercial CHP 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 CHP, 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

[0014]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

An improved method for the production of phenol, acetone and alpha-methyl styrene (AMS) from a cumene hydroperoxide and dimethylbenzyl alcohol (DMBA) mixture is described, wherein 0.5-5% additional water by weight is added prior to the final DMBA dehydration step, carried out in the presence of about 20-400 ppm mineral acid catalyst at 110-150° C. for 0.5 to 40 minutes residence time. The use of additional water allows greater flexibility in maintaining optimum temperature in the second stage over a much broader turndown range with fixed equipment, decreases the residual dicumyl peroxide (DCP) at the yield optimum for a given temperature, and increases the overall yield of AMS at optimum conditions at a given temperature.

Description

FIELD OF THE INVENTION[0001]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.BACKGROUND OF THE INVENTION[0002]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.[0003]The acid catalyzed decomposition of CHP is well known, most modern processes utilizing a two step, continuous flow approach to optimize overall yield in this step, especially of DMBA to AMS. Examples of such prior art are U.S. Pat. Nos. 7,482,493, 7,109,385, 6,307,112, 6,225,513, 6,201,157, 6,057,483, 5,998,677, 5,463,136, 5,430,200, 5...

Claims

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Application Information

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IPC IPC(8): C07C45/53C07C2/86C07C37/08
CPCC07C1/24C07C37/08C07C45/53C07C2527/054C07C39/04C07C49/08C07C15/44Y02P20/52C07C27/00
Inventor KEENAN, SCOTT ROYHAGANS, MICHAEL KEITH
Owner HONEYWELL INT INC
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