Carboxylic Acid Anhydride Synthesis Using Aprotic Polar Solvents

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Solution Overview

Problem

Existing methods for producing carboxylic acid anhydrides require high temperatures and acid solvents, leading to energy inefficiency, colored products, and by-product formation, as well as the need for acid-resistant equipment and disposal.

Innovation Solution

A method involving heating compositions containing specific compounds in aprotic polar solvents with boiling points of 50°C or more to produce carboxylic acid anhydrides at lower temperatures without using acid solvents, reducing energy requirements and by-product formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If high temperature heating is used to produce carboxylic acid anhydride, then the reaction proceeds efficiently, but energy consumption increases and colored products are formed

Engineering Contradiction:
Improvereaction efficiencyVSAvoidenergy consumption
Core Design Contradiction:
ProductivityVSUse of energy by moving object

Solution Approach 1:

The patent changes the temperature parameter from conventional high temperature (240-250°C) to low temperature (50-150°C) by introducing a novel solvent system and catalyst combination, achieving efficient anhydride formation without excessive energy input

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces aprotic polar solvents and catalysts as intermediaries to facilitate the dehydration reaction at lower temperatures, replacing the need for direct high-temperature heating while maintaining reaction efficiency

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If acid solvents are used to produce carboxylic acid anhydride, then the reaction proceeds, but colored products and by-products are formed requiring acid-resistant equipment

Engineering Contradiction:
Improvereaction efficiencyVSAvoidcolored products and by-products
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and eliminates acid solvents from the reaction system, replacing them with aprotic polar solvents that do not generate colored by-products or require special acid-resistant equipment

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the harmful effect of acid-catalyzed side reactions into a benefit by using alternative catalysts that promote anhydride formation without generating colored impurities, turning a problematic pathway into a clean synthesis route

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

3Productivity

If conventional high temperature method is used, then carboxylic acid anhydride is produced, but equipment complexity increases due to acid-resistant requirements

Engineering Contradiction:
Improveproduction capabilityVSAvoidequipment requirements
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The patent employs conventional equipment that can be easily disposed of or replaced, eliminating the need for expensive acid-resistant materials and complex equipment designs, making the process more accessible and cost-effective

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 efficiently produces high-quality carboxylic acid anhydrides at lower temperatures, minimizing energy consumption and avoiding the use of acid solvents, thus reducing equipment needs and environmental impact.

Implementation Method 1

the solvent contains an aprotic polar solvent having a boiling point of 50° C. or more

Methodology Applied
Scientific EffectWater absorption: Absorption (physical)

Implementation Method 2

heating a composition containing a compound represented by formula (1) in a first solvent to produce a carboxylic acid anhydride

Methodology Applied
Scientific EffectThermal heating: Heating

Data Source

PatentUS10065969B2Method for producing carboxylic acid anhydride, method for producing carboxylic imide, and method for manufacturing electrophotographic photosensitive member
Publication Date: 2018.09.04 CANON KK
  • US10065969B2 patent drawing
  • US10065969B2 patent drawing
  • US10065969B2 patent drawing

AI summary

A method for producing a carboxylic acid anhydride includes heating a composition containing a specific compound in a solvent to yield the carboxylic acid anhydride. The solvent is an aprotic polar solvent having a boiling point of 50° C. or more.