Crystallizing Alanine N-Acetic Acid Precursors
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Solution Overview
Problem
Existing methods fail to effectively isolate and crystallize acetonitriles containing carboxylate functionality, which are crucial for biodegradable chelating agents, due to their high solubility and lack of disclosure in prior art on their isolation and crystallization processes.
Innovation Solution
The development of alanine N-acetic acid precursors, including alanine N-monoacetonitrile and N,N-diacetonitrile, which are crystallized through an aqueous solution process involving racemization and concentration, allowing for the isolation of crystalline forms that can be hydrolyzed to produce biodegradable chelating agents like MGDA and MGMA.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If acetonitriles containing carboxylate functionality are isolated from aqueous reaction mixtures, then the biodegradable chelating agents can be produced, but the high solubility of these acetonitriles prevents effective isolation and crystallization
Solution Approach 1:
The patent changes the chemical parameters of the acetonitrile molecules by introducing specific structural modifications that reduce their solubility in aqueous solutions. This allows the highly soluble acetonitriles containing carboxylate functionality to be isolated and crystallized effectively, resolving the contradiction between maintaining biodegradability and achieving isolability.
Solution Approach 2:
The patent extracts the acetonitrile products from the aqueous reaction mixture through controlled crystallization processes. By modifying the molecular structure to reduce solubility, the acetonitriles can be separated and isolated from the reaction medium, enabling effective production of biodegradable chelating agents.
2Ease of manufacture
If acetonitriles with carboxylate groups are used as intermediates, then biodegradable chelating agents are obtained, but their high solubility makes storage and transport difficult
Solution Approach 1:
The patent modifies the physical parameters of the acetonitrile intermediates by structural changes that reduce their solubility. This transformation maintains their ability to produce biodegradable chelating agents while improving their storage stability and handling characteristics for industrial applications.
3Device complexity
If prior art methods are used for isolating acetonitriles, then simple processes are available, but no method exists for isolating acetonitriles containing carboxylate functionality in solid form
Solution Approach 1:
The patent introduces specific chemical parameter changes in the acetonitrile structure that enable solid-form isolation. This allows the development of new crystallization processes for acetonitriles containing carboxylate groups, filling the gap in prior art while maintaining process feasibility.
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 enables the stable storage and transport of crystalline precursors, increasing their shelf life and purity, and allows for the production of biodegradable chelating agents in a controlled manner, overcoming the solubility issues of previous methods.
Implementation Method 1
ensuring the alanine is at least partly racemized
Implementation Method 2
a third step crystallizing the aqueous solution to separate the alanine N-acetic acid precursor
Data Source
AI summary
The present invention relates to alanine N-acetic acid precursors of formula (i) COOM-CH(CH3)—NH—(CH2CN), wherein M is hydrogen (alanine N-monoacetonitrile), or (ii) COOM-CH(CH3)—N—(CH2CN)2, wherein 0 to 50% of all M is sodium or potassium and 50 to 100% of all M is hydrogen (alanine N,N-diacetonitrile and its partial sodium or potassium salts) comprising L-alanine to D-alanine in a range of from 75:25 to 50:50 (L:D), or (iii) COOM-CH(CH3)—N—(CH2CONH2)2, wherein M is hydrogen (alanine N,N-diacetamide), in the form of crystals, and relates to a process to prepare these precursors and their use, especially to give MGMA or MGDA.