Amino Acid Methyl Ester Synthesis via Cyclic Reflux

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Solution Overview

Problem

Existing methods for synthesizing amino acid methyl esters face low yields and high alcohol consumption, making them economically unattractive.

Innovation Solution

A process involving refluxing a mixture of free amino acid, methanol, and a strong acid, followed by concentration and repeated cycles of adding methanol, significantly increases the yield of amino acid methyl esters while reducing alcohol consumption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If the process according to EP-A-0544205 is used to increase yield, then the yield of amino acid methyl esters is improved, but the consumption of alcohol increases significantly

Engineering Contradiction:

Improveyield of amino acid methyl estersVSAvoidconsumption of alcohol

Core Design Contradiction:

ProductivityVSLoss of substance

Solution Approach 1:

The process is divided into multiple cycles, each consisting of adding alcohol, refluxing, and concentrating. This segmentation allows the reaction to proceed in stages with controlled alcohol addition, achieving high yield while minimizing overall alcohol consumption compared to continuous addition methods.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The process employs periodic cycles of alcohol addition followed by refluxing and concentrating steps. This periodic action pattern allows the system to build up ester product gradually while removing water and excess alcohol, achieving high conversion without requiring excessive alcohol input.

Inventive Principle:

Principle #19Periodic action

2Productivity

If sulfuric acid is used as catalyst in the esterification process, then the reaction proceeds, but the yields are rather low

Engineering Contradiction:

Improveyield of amino acid methyl estersVSAvoideconomic attractiveness

Core Design Contradiction:

ProductivityVSEase of manufacture

Solution Approach 1:

The process modifies the reaction parameters by using multiple cycles of alcohol addition, refluxing, and concentrating rather than a single continuous process. This changes the temporal and concentration parameters of the reaction, achieving high yield while maintaining economic feasibility through reduced alcohol consumption.

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 process achieves high yields of amino acid methyl esters with minimal alcohol usage, optimizing the synthesis by repeating the reflux and concentration steps to enhance the esterification ratio.

Implementation Method 1

a process for the synthesis of amino acid methyl esters... refluxing a reaction mixture comprising a free amino acid, methanol and a strong acid

Methodology Applied

Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

concentrating the mixture obtained in step (a)

Methodology Applied

Scientific EffectEvaporation: Evaporation

Implementation Method 3

refluxing a reaction mixture comprising a free amino acid, methanol and a strong acid

Methodology Applied

Scientific EffectReflexing: Heating

Data Source

PatentEP2132166B1Process for the preparation of amino acid methyl esters

Publication Date: 2013.01.16 DSM SINOCHEM PHARMA NETHERLANDS

AI summary

The present invention describes a process for the synthesis of an amino acid methyl ester comprising the following steps: (a) refluxing a reaction mixture comprising a free amino acid, methanol and a strong acid; (b) concentrating the mixture; (c) adding methanol; (d) repeating steps a-c one or more times.