Oxirane Production Solvent System for Catalyst Protection

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Solution Overview

Problem

Existing processes for producing oxiranes like epichlorohydrin using peroxides result in high methanol consumption, leading to energy-intensive separation and byproduct formation, catalyst deactivation, and increased wastewater generation, with the need for additional downstream processing steps.

Innovation Solution

A multiphase process using a mixed solvent system with a titanium silicalite-1 (TS-1) catalyst, where the solvent mixture includes a small amount of methanol and a non-reactive co-solvent, allowing the oxirane to partition into the organic phase, reducing contact with water and extending catalyst lifetime without additional downstream components.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If large quantities of methanol are used in the peroxide reaction to obtain high activity, then catalyst activity is improved, but byproduct formation increases and energy consumption for separation increases

Engineering Contradiction:
Improvecatalyst activityVSAvoidbyproduct formation
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the concentration parameter of methanol from large excess to a controlled range (3-40 wt%), and introduces a co-solvent parameter to modify the solvent system composition, thereby reducing byproduct formation while maintaining catalyst activity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a co-solvent as an intermediary substance that mediates between methanol and the oxirane product, reducing the direct harmful interaction between methanol and oxirane that leads to byproduct formation

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If large quantities of methanol are used in the peroxide reaction, then catalyst activity is improved, but energy consumption for separation and purification increases

Engineering Contradiction:
Improvecatalyst activityVSAvoidenergy consumption for separation
Core Design Contradiction:
ReliabilityVSUse of energy by moving object

Solution Approach 1:

The patent changes the methanol concentration parameter to a lower range (3-40 wt%) and adjusts the co-solvent ratio, which reduces the energy required for separation and purification operations while maintaining sufficient catalyst activity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts the harmful function of excessive methanol from the system by removing the requirement for large quantities, keeping only the essential amount needed for catalyst activation while eliminating the need for energy-intensive separation of excess solvent

Inventive Principle:
Principle #2Taking out (Extraction)

3Reliability

If high concentration of methanol is used, then catalyst activity is improved, but catalyst lifetime decreases due to deactivation

Engineering Contradiction:
Improvecatalyst activityVSAvoidcatalyst lifetime
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent optimizes the methanol concentration parameter to a moderate range (3-40 wt%) rather than high concentration, and adjusts the co-solvent composition, which reduces catalyst deactivation and extends catalyst lifetime while maintaining adequate activity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The co-solvent acts as a protective intermediary that reduces the direct contact and harmful interaction between high concentrations of methanol and the catalyst, thereby preventing catalyst deactivation and extending its operational lifetime

Inventive Principle:
Principle #24Intermediary (Mediator)

4Manufacturing precision

If heavy solvent is added following the reaction instead of during the reaction, then oxirane product can be recovered, but byproduct formation increases due to contact with water and alcohol phase

Engineering Contradiction:
Improveoxirane product recoveryVSAvoidbyproduct formation
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The patent applies preliminary action by adding the co-solvent during the reaction phase rather than after, which creates a protective environment that prevents byproduct formation from the outset while still enabling effective oxirane recovery

Inventive Principle:
Principle #10Preliminary action

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

This approach reduces byproduct formation, increases reaction selectivity, and decreases energy consumption by allowing simple phase separation, thereby improving the efficiency and sustainability of the oxirane production process.

Implementation Method 1

allowing the oxirane to partition into the organic phase, reducing contact with water

Methodology Applied
Scientific EffectPartitioning: Liquid-Liquid Extraction

Implementation Method 2

reacting an olefin and a peroxide compound in the presence of a catalyst such as titanium silicalite-1 (TS-1)

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP2462129B1Process for producing an oxirane
Publication Date: 2015.09.16 BLUE CUBE IP LLC
  • EP2462129B1 patent drawingFigure 1
  • EP2462129B1 patent drawingFigure 2
  • EP2462129B1 patent drawingFigure 3

AI summary

A multiple liquid phase composition and process for preparing an oxirane product, such as epichlorohydrin, including a reaction mixture of: (a) at least one olefin, wherein the olefin is selected from one of (i) an aliphatic olefin or substituted aliphatic olefin, with the proviso that the aliphatic olefin is not propylene, (ii) a cycloaliphatic olefin, (iii) an aromatic olefin, (iv) a cycloaromatic olefin, and (v) mixtures thereof; (b) at least one peroxide compound, (c) at least one catalyst, and (d) and a solvent mixture; wherein the solvent mixture comprises at least (i) at least one alcohol or a combination of alcohols, and (ii) at least one non-reactive co-solvent; wherein the solvents are mixed at a predetermined concentration; wherein the non-reactive co- solvent has a different boiling point than the oxirane product; and wherein the oxirane product partitions into a high affinity solvent during the reaction. The process of the present invention advantageously produces a waste stream with no significant amount of sodium chloride (NaCl). In one embodiment, the present invention includes a process for preparing epichlorohydrin from allyl chloride and hydrogen peroxide including reacting (a) an allyl chloride with (b) hydrogen peroxide, in the presence of (c) a titanium silicalite-1 (TS-1) catalyst and (d) in the presence of a predetermined amount of a mixed solvent system; wherein the mixed solvent system includes at least (i) methanol and (ii) at least one non-reactive co-solvent.