Dry Cumene Oxidation Selectivity

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Solution Overview

Problem

Current cumene oxidation processes face challenges in achieving high selectivity for cumene hydroperoxide due to side reactions and impurities, leading to inefficient product separation and decomposition, with wet oxidation methods requiring additional steps for carbonate removal and neutralization.

Innovation Solution

A dry oxidation process using a series of reactors with reducing liquid levels, operated at specific pressures and temperatures, where only cumene and oxygen-containing gas are fed, with off-gases treated to recycle unreacted cumene and condensates, enhancing selectivity by minimizing heat input and side reactions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If wet oxidation procedure is used with aqueous carbonate solution, then oxidation reaction can proceed, but additional steps for carbonate removal and neutralization are required

Engineering Contradiction:
Improveoxidation reaction efficiencyVSAvoidprocess steps
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The invention extracts and removes the carbonate component from the oxidation system, transitioning from wet oxidation with aqueous carbonate solution to dry oxidation without carbonate. This eliminates the need for subsequent carbonate removal and neutralization steps, directly resolving the technical contradiction by taking out the problematic element while preserving the core oxidation function

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the fundamental parameter of the oxidation system by eliminating the aqueous carbonate medium and operating under dry conditions. This parameter change transforms the process from a multi-step wet oxidation requiring neutralization to a simplified dry oxidation process, resolving the contradiction between reaction efficiency and process complexity

Inventive Principle:
Principle #35Parameter changes

2Productivity

If temperature is increased to compensate for decreased reaction rate, then reaction rate increases, but CHP decomposition increases

Engineering Contradiction:
Improvereaction rateVSAvoidCHP stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention changes the oxidation conditions to dry oxidation without carbonate, which modifies the reaction mechanism and allows for lower operating temperatures. This parameter change enables maintaining high reaction rates while avoiding excessive CHP decomposition, resolving the contradiction between productivity and reliability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention replaces the thermal-mechanical approach of compensating for low reaction rates with high temperature by substituting the oxidation mechanism itself. The dry oxidation without carbonate creates a more selective reaction pathway that achieves high productivity at lower temperatures, thereby preserving CHP stability

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

3Productivity

If impurities such as phenol and AMS are present, then oxidation can proceed, but CHP decomposition is caused

Engineering Contradiction:
Improveoxidation process continuityVSAvoidCHP stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The invention applies preliminary anti-action by using dry oxidation conditions that prevent the formation and accumulation of decomposition-inducing impurities like phenol and AMS. By eliminating carbonate and operating under dry conditions, the process prevents the chemical environment that leads to impurity formation, thereby protecting CHP stability while maintaining continuous oxidation

Inventive Principle:
Principle #9Preliminary anti-action

Solution Approach 2:

The invention converts the potential harm of impurity formation into benefit by using dry oxidation conditions that actually prevent impurity accumulation. The absence of carbonate and aqueous medium creates conditions where CHP is more stable and less prone to decomposition by phenol and AMS, turning what could be a harmful scenario into a beneficial one

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The process achieves a total selectivity of over 94% for cumene hydroperoxide, eliminating the need for carbon beds and reducing energy consumption, while maintaining product quality and minimizing CHP decomposition.

Implementation Method 1

The present invention concerns a process for the oxidation of cumene to cumene hydroperoxide

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

The liquid phase oxidation of cumene is explained in terms of a radical mechanism by Kazua Hattori et al. in Journal of Chemical Engineering of Japan, vol. 3, no. 1, (1970), p. 72-78

Methodology Applied
Scientific EffectRadical mechanism:

Implementation Method 3

the off-gases from the top section of each oxidation reactor are separated and cooled, whereby a condensate containing unreacted cumene is formed

Methodology Applied
Scientific EffectCondensation: Condensation

Data Source

PatentEP2379495B1Improving cumene oxidation
Publication Date: 2017.03.01 BOREALIS AG
  • EP2379495B1 patent drawing
  • EP2379495B1 patent drawing
  • EP2379495B1 patent drawing

AI summary

A process for oxidizing cumene to cumene hydroperoxide using an oxygen containing gas, which process composes - conducting a cumene feed and an oxygen containing gas feed to at least the first oxidation reactor in a series of 3-8 reactors, thereby forming an oxidation mixture, and - conducting the oxidation mixture from one oxidation reactor to at least one subsequent reactor, wherein - the reactors are operated with reducing liquid levels; - the oxidation is operated as a dry oxidation, whereby the only gaseous feeds conducted to the oxidation reactors are the cumene feed and the oxygen containing gas feed; - the oxygen containing gas feed is washed with caustic and then with water to remove all acidic or caustic traces before conducting it into an oxidation reactor; - the pressure within each oxidation reactor is in the range of 0-10 barg; - the off-gases from the top section of each oxidation reactor are separated and cooled, whereby a condensate containing unreacted cumene is formed, and - washing the condensate and recycling at least a part of it to at least the first oxidation reactor; - the non-condensed off-gases are treated in a thermal oxidizer; and - the first reactor in the series of oxidation reactors has a liquid inventory of 30- 300% larger than in the remaining reactors, preferably 50-100%, or the first two reactors in the series of oxidation reactors have a liquid inventory of 30- 300% larger than in the remaining reactors, preferably 50-100%.