1-Aminocyclopropanecarboxylic Acid Non-Hydrate Production via Selective Crystallization

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Solution Overview

Problem

Current methods for producing 1-aminocyclopropanecarboxylic acid are not suitable for industrial production due to inefficiencies in converting 1-aminocyclopropanecarboxylic acid hydrochloride into its free form, particularly in achieving high purity and yield.

Innovation Solution

Treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C3-C4 alcohol and water facilitates the crystallization of 1-aminocyclopropanecarboxylic acid 0.5 hydrate, which is then heated to obtain 1-aminocyclopropanecarboxylic acid non-hydrate, optimizing filtration properties and purity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional methods are used to convert 1-aminocyclopropanecarboxylic acid hydrochloride into free form, then the conversion can be achieved, but the purity and yield are insufficient for industrial production

Engineering Contradiction:
ImprovepurityVSAvoidprocess simplicity
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the pH parameter by adding tertiary amine to convert the hydrochloride salt form to free form, enabling selective crystallization. This parameter change resolves the contradiction by achieving high purity through controlled pH adjustment while maintaining process simplicity

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes phase transition through selective crystallization where the free form of 1-aminocyclopropanecarboxylic acid crystallizes from the solution while the tertiary amine hydrochloride remains dissolved. This phase transition enables separation of the desired product with high purity without complex processing steps

Inventive Principle:
Principle #36Phase transitions

2Manufacturing precision

If the reaction mixture is heated to convert 0.5 hydrate to non-hydrate form, then the desired non-hydrate product is obtained, but energy consumption increases

Engineering Contradiction:
Improveproduct form purityVSAvoidheating energy
Core Design Contradiction:
Manufacturing precisionVSUse of energy by moving object

Solution Approach 1:

The patent exploits the phase transition of water molecules of crystallization that occurs upon heating. By controlling the heating temperature and duration, the 0.5 hydrate form transitions to the non-hydrate form, achieving the desired product form purity while managing energy consumption through optimized heating parameters

Inventive Principle:
Principle #36Phase transitions

Data Source

PatentEP3636630B1Production method for 1 amino cyclopropane carboxylic acid nonhydrate
Publication Date: 2021.12.15 SUMITOMO CHEM CO LTD
  • EP3636630B1 patent drawingFigure 1~2
  • EP3636630B1 patent drawingFigure 3
  • EP3636630B1 patent drawing

AI summary

1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C3-C4 alcohol and water, keeping the reaction mixture at 50°C or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and heating the obtained crystal to 80 to 245°C.