Liquid Phase Synthesis of 1-Acyloxy-2-Methyl-2-Propene

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Solution Overview

Problem

Current methods for producing 1-acyloxy-2-methyl-2-propene either generate inorganic by-products, require high energy consumption, or have low production efficiency due to constraints in oxygen concentration and equipment costs, especially in gas phase reactions, and inefficient substrate conversion.

Innovation Solution

A liquid phase method involving reacting isobutylene with a carboxylic acid and oxygen in the presence of a catalyst, where the amount of isobutylene exceeds 1 mol but is less than 50 mol per mol of carboxylic acid, using a catalyst with noble metals like palladium and transition metals, at optimized reaction temperatures and conditions to suppress overreaction and enhance productivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-generated harmful factors

If gas phase reaction is used to avoid inorganic by-products, then environmental load is reduced, but oxygen concentration must be kept low for safety which constrains substrate conversion and requires recovery devices

Engineering Contradiction:
Improveinorganic by-product generationVSAvoidsubstrate conversion
Core Design Contradiction:
Object-generated harmful factorsVSProductivity

Solution Approach 1:

The invention changes the physical state parameter from gas phase to liquid phase reaction. This allows the use of higher oxygen concentrations without explosive hazards, thereby improving substrate conversion and productivity while avoiding inorganic by-product generation through the use of a solid acid catalyst

Inventive Principle:
Principle #35Parameter changes

2Object-generated harmful factors

If gas phase reaction is used, then inorganic by-products are avoided, but equipment cost increases due to vaporizers and reaction tubes filled with catalyst

Engineering Contradiction:
Improveinorganic by-product generationVSAvoidequipment cost
Core Design Contradiction:
Object-generated harmful factorsVSDevice complexity

Solution Approach 1:

The invention changes the physical state parameter from gas phase to liquid phase reaction. This eliminates the need for vaporizers and complex gas-phase reaction equipment, thereby reducing equipment cost and simplifying the reaction system while still avoiding inorganic by-product generation through solid acid catalysis

Inventive Principle:
Principle #35Parameter changes

3Object-generated harmful factors

If gas phase reaction is used to avoid inorganic by-products, then environmental load is reduced, but energy consumption increases due to vaporization requirements

Engineering Contradiction:
Improveinorganic by-product generationVSAvoidenergy consumption
Core Design Contradiction:
Object-generated harmful factorsVSUse of energy by moving object

Solution Approach 1:

The invention changes the physical state parameter from gas phase to liquid phase reaction. This eliminates the energy-intensive vaporization step while maintaining the environmental benefit of avoiding inorganic by-products through solid acid catalysis, thereby significantly reducing energy consumption

Inventive Principle:
Principle #35Parameter changes

4Productivity

If liquid phase reaction is used with excess carboxylic acid, then substrate conversion is improved, but overreaction occurs which reduces production efficiency

Engineering Contradiction:
Improvesubstrate conversionVSAvoidselectivity
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention changes the catalyst type parameter from homogeneous to solid acid catalyst. This allows the use of excess carboxylic acid to improve substrate conversion while the solid acid catalyst maintains high selectivity by preventing overreaction, thereby resolving the contradiction between conversion and selectivity

Inventive Principle:
Principle #35Parameter changes

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 method eliminates inorganic by-product generation, improves production efficiency, and reduces energy and equipment costs by operating under liquid phase conditions, achieving high conversion and selectivity of 1-acyloxy-2-methyl-2-propene without excessive overreaction.

Implementation Method 1

reacting isobutylene with a carboxylic acid and oxygen in the presence of a catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

reaction of isobutylene, acetic acid, and oxygen in the presence of a solid catalyst

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentUS11643382B2Method for producing 1-acyloxy-2-methyl-2-propene
Publication Date: 2023.05.09 KURARAY CO LTD
  • US11643382B2 patent drawing
  • US11643382B2 patent drawing
  • US11643382B2 patent drawing

AI summary

A method for producing a 1-acyloxy-2-methyl-2-propene represented by the following general formula (II), including reacting a carboxylic acid represented by the following general formula (I), isobutylene, and oxygen, in the presence of a catalyst, in a liquid phase, with an amount of the isobutylene used of more than 1 mol and 50 mol or less per 1 mol of the carboxylic acid.