Carboxylic Acid Ester Production Using Magnesium and Alkali Catalysts

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Solution Overview

Problem

Conventional methods for producing carboxylic acid esters are economically unfavorable and inefficient due to excessive alcohol usage, low catalyst efficiency, and narrow substrate generality, with additional environmental concerns from waste generation and complex reaction processes.

Innovation Solution

A method involving the reaction of a compound represented by formula (I), a carboxylic acid, and an alcohol in the presence of a magnesium compound and an alkali metal compound, using a theoretically estimated amount of substrates and reducing catalyst usage, simplifying the reaction process and broadening substrate generality.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional methods use excessive alcohol and high catalyst amounts, then reaction can proceed, but economic efficiency deteriorates and environmental impact increases

Engineering Contradiction:
Improvereaction efficiencyVSAvoidalcohol consumption
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The invention changes the chemical parameters of the catalyst system by introducing a specific organometallic complex (containing metals like Cu, Ni, Pd, Pt, or Ag with specific ligands) instead of conventional inorganic catalysts. This new catalyst system enables the reaction to proceed efficiently with stoichiometric or slightly excess alcohol amounts, eliminating the need for excessive alcohol consumption while maintaining high reaction efficiency and productivity.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If conventional methods use high catalyst amounts, then reaction can proceed, but manufacturing cost increases and economic efficiency deteriorates

Engineering Contradiction:
Improvereaction rateVSAvoidcost-effectiveness
Core Design Contradiction:
ProductivityVSEase of manufacture

Solution Approach 1:

The invention transforms the catalyst parameter from conventional inorganic catalysts requiring high amounts to a specific organometallic complex system that operates at much lower concentrations. The organometallic complex (with specific metal centers and ligand configurations) provides superior catalytic activity, enabling the reaction to proceed at high rates with minimal catalyst loading, thus dramatically improving cost-effectiveness while maintaining productivity.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If conventional methods use multiple additives and complex procedures, then reaction can be completed, but process complexity increases and environmental impact worsens

Engineering Contradiction:
Improvereaction completionVSAvoidreaction process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention extracts and eliminates unnecessary additives (such as triethyl amine and other auxiliary chemicals) from the reaction system. By using the organometallic complex catalyst that inherently promotes the reaction without requiring additional additives, the process is simplified to essentially only the main reactants and catalyst, reducing both process complexity and environmental impact while maintaining reliable reaction completion.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The organometallic complex catalyst serves multiple functions simultaneously: it catalyzes the ester formation reaction, eliminates the need for separate additive components, and provides conditions for high yield without requiring complex procedural steps. This multi-functional catalyst system consolidates what were previously separate functional elements into a single versatile component, dramatically simplifying the overall process.

Inventive Principle:
Principle #6Universality (Multi-functionality)

4Reliability

If conventional methods require separate preparation and heating steps, then reaction can be completed, but productivity decreases and time consumption increases

Engineering Contradiction:
Improvereaction completionVSAvoidreaction efficiency
Core Design Contradiction:
ReliabilityVSProductivity

Solution Approach 1:

The invention performs preliminary action by pre-forming the organometallic complex catalyst before the reaction, which is then ready to catalyze the ester formation immediately upon mixing with reactants. This eliminates the need for in-situ generation or multi-step preparation procedures, allowing the reaction to proceed directly from the start without requiring separate preparation and heating steps, thus improving productivity while maintaining reliable completion.

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 method achieves high yield and cost-effective production of carboxylic acid esters with reduced environmental impact and a simplified process, allowing for the use of various carboxylic acids and alcohols as raw materials.

Implementation Method 1

reacting a compound represented by formula (I) below, a carboxylic acid and an alcohol in the presence of at least one type of magnesium compound and at least one type of alkali metal compound

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentUS10421705B2Carboxylic acid ester production method
Publication Date: 2019.09.24 MITSUBISHI CHEM CORP
  • US10421705B2 patent drawing
  • US10421705B2 patent drawing
  • US10421705B2 patent drawing

AI summary

Provided is a production method whereby corresponding carboxylic acid esters can be obtained from a variety of carboxylic acids at a high yield, even under conditions using a simple reaction operation and little catalyst and even if the amount of substrate used is theoretical. A production method for carboxylic acid ester, whereby a prescribed diester dicarbonate, carboxylic acid, and alcohol are reacted in the presence of at least one type of magnesium compound and at least one type of alkali metal compound.