Olefin Epoxidation Process Using Hansen Solubility Parameters

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Conventional epoxidation processes of olefins with peroxides face challenges in achieving high conversion rates while maintaining selectivity and minimizing hydrolysis, particularly in batch reactions where temperature control is difficult, leading to safety concerns and reduced production capacity.

Innovation Solution

A process for epoxidation of olefins using a solvent with specific solubility parameters (δT,solvent and δH,solvent) that match or closely align with the epoxide product parameters (δT,product and δH,product), allowing for increased selectivity and reduced hydrolysis, utilizing a reactor such as a micro-reactor or flow reactor with suitable peroxide as the epoxidizing agent.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If peroxide is added dropwise in a batch reactor at lower temperature, then selectivity of epoxidation is improved, but reaction time increases and production capacity decreases

Engineering Contradiction:
Improveselectivity of epoxidationVSAvoidproduction capacity
Core Design Contradiction:
Manufacturing precisionVSProductivity

Solution Approach 1:

The patent transitions from batch reaction to continuous flow reaction, enabling continuous addition of peroxide and continuous removal of product. This maintains optimal reaction conditions throughout the process, achieving high selectivity while increasing production capacity through continuous operation rather than intermittent batch processing.

Inventive Principle:
Principle #20Continuity of useful action

Solution Approach 2:

The patent uses a flow reactor that segments the reaction into small, controlled segments along the flow path. This allows precise control of temperature and residence time in each segment, maintaining high selectivity while enabling continuous high-volume production through parallel processing of multiple reaction segments.

Inventive Principle:
Principle #1Segmentation

2Quantity of substance

If reaction time is extended to improve conversion rate, then more olefin is converted, but temperature control becomes more difficult and safety concerns increase

Engineering Contradiction:
Improveconversion rate of olefinVSAvoidtemperature control and safety
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The continuous flow reactor enables constant removal of reaction heat as product forms, preventing temperature runaway even at high conversion rates. The continuous flow of reactants and products through the reactor maintains thermal equilibrium, allowing high conversion while preserving safety and temperature control.

Inventive Principle:
Principle #20Continuity of useful action

Solution Approach 2:

The patent employs a dynamic flow system where residence time, flow rate, and temperature can be continuously adjusted to optimize conversion while maintaining safety. The system adapts to changing reaction conditions in real-time, enabling high conversion rates without compromising temperature control or safety.

Inventive Principle:
Principle #15Dynamics

3Stability of the object's composition

If peracetic acid with low water content is used to reduce hydrolysis, then epoxide stability is improved, but process complexity increases due to additional purification steps

Engineering Contradiction:
Improveepoxide stabilityVSAvoidprocess complexity
Core Design Contradiction:
Stability of the object's compositionVSDevice complexity

Solution Approach 1:

The continuous flow reactor enables immediate reaction of peracetic acid with olefin upon mixing, completing the epoxidation before significant hydrolysis can occur. This continuous processing eliminates the need for extensive purification to remove water, as the reaction timeframe is too short for hydrolysis to compete, simplifying the overall process while maintaining epoxide stability.

Inventive Principle:
Principle #20Continuity of useful 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 enables high olefin conversion rates with high diepoxide selectivity and low hydrolysis, improving production efficiency and safety by controlling reaction conditions effectively.

Implementation Method 1

reacting peroxide with the olefin in a reactor in the presence a solvent, wherein the solvent has solubility parameters of δT,solvent and δH,solvent, and an epoxide product has solubility parameters of δT,product and δH,product

Methodology Applied
Scientific EffectSolubility: Solvation

Data Source

PatentUS9499505B2Process for the epoxidation of olefins
Publication Date: 2016.11.22 CHANG CHUN PLASTICS CO LTD
  • US9499505B2 patent drawing
  • US9499505B2 patent drawing
  • US9499505B2 patent drawing

AI summary

The subject invention is related to a process for the epoxidation of olefin with peroxide, comprising reacting peroxide with olefin in the presence a solvent, wherein the solvent has Hansen Solubility Parameters (HSPs) of δT,solvent and δH,solvent and the epoxide product has Hansen Solubility Parameters (HSPs) of δT,product and δH,product, and wherein:δT,product−6≦δT,solvent≦δT,product+6, andδH,product−6≦δH,solvent.