Glutamic Acid Benzyl Ester N-Carboxylic Anhydride Crystallization

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Solution Overview

Problem

Conventional methods for producing glutamic acid benzyl ester N-carboxylic anhydride result in crystals with low bulk density and lack storage stability.

Innovation Solution

A method involving dissolving glutamic acid benzyl ester N-carboxylic anhydride in a heated solvent at temperatures above 40°C, followed by adding an anti-solvent like heptane, hexane, or pentane, to precipitate crystals at elevated temperatures, achieving a bulk density of 0.45 g/cm³ or higher and stable crystal polymorphs.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If conventional recrystallization methods are used (dissolving in ethyl acetate and adding anti-solvent like carbon tetrachloride or hexane), then purification is achieved, but the bulk density of crystals remains low (0.23-0.38 g/cm³)

Engineering Contradiction:
Improvebulk densityVSAvoidcrystallization process
Core Design Contradiction:
Manufacturing precisionVSEase of manufacture

Solution Approach 1:

The patent changes the temperature parameter during crystallization, specifically performing crystallization at elevated temperatures (50-80°C) rather than at room temperature or low temperatures. This temperature parameter change results in crystals with bulk density of 0.45 g/cm³ or more, resolving the contradiction between achieving purification and obtaining high bulk density crystals.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If conventional recrystallization methods are used, then purification is achieved, but storage stability of the crystals is insufficient

Engineering Contradiction:
Improvestorage stabilityVSAvoidcrystal polymorph quality
Core Design Contradiction:
ReliabilityVSManufacturing precision

Solution Approach 1:

The patent changes the temperature parameter to 50-80°C during crystallization, which produces a specific crystal polymorph with superior storage stability. This parameter change ensures both the desired crystal quality and long-term storage stability, resolving the contradiction between manufacturing precision and reliability.

Inventive Principle:
Principle #35Parameter changes

3Manufacturing precision

If crystallization is performed at low temperature (0°C) after adding anti-solvent, then crystals precipitate, but the bulk density remains low and storage stability is poor

Engineering Contradiction:
Improvebulk densityVSAvoidcrystallization temperature
Core Design Contradiction:
Manufacturing precisionVSTemperature

Solution Approach 1:

The patent inverts the conventional approach by performing crystallization at high temperature (50-80°C) instead of low temperature (0°C). This inversion of the temperature parameter leads to the formation of crystal polymorphs with high bulk density (0.45 g/cm³ or more) and excellent storage stability, effectively resolving the contradiction between temperature and manufacturing precision.

Inventive Principle:
Principle #13The other way round (Inversion)

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

The method produces crystal polymorphs with enhanced storage stability and bulk density, as demonstrated by powder X-ray diffraction patterns and bulk density measurements.

Implementation Method 1

dissolving glutamic acid benzyl ester N-carboxylic anhydride in a solvent which has been heated at a temperature equal to or higher than 40°C

Methodology Applied
Scientific EffectDissolution: Solvation

Implementation Method 2

adding an anti-solvent... to precipitate crystals at elevated temperatures

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Implementation Method 3

cooling the crystals

Methodology Applied
Scientific EffectCooling: Cooling

Data Source

PatentEP2690097B1Method for crystallizing glutamic acid benzyl ester n-carboxylic anhydride
Publication Date: 2017.05.17 NIPPON SODA CO LTD
  • EP2690097B1 patent drawingFigure 1~2
  • EP2690097B1 patent drawingFigure 3~4
  • EP2690097B1 patent drawingFigure 5

AI summary

An object of the present invention is to provide crystal polymorphs which have a high bulk density and are excellent in storage stability, among crystal polymorphs of a glutamic acid benzyl ester N-carboxylic anhydride. According to the present invention, the crystal polymorphs of glutamic acid benzyl ester N-carboxylic anhydride that have a bulk density of 0.45 g/ cm3 or higher can be obtained by dissolving glutamic acid benzyl ester N-carboxylic anhydride in a solvent which has been heated at a temperature equal to or higher than 40°C and lower than a boiling point thereof and is in an amount of 0.5 L or more per mol of the glutamic acid benzyl ester N-carboxylic anhydride, adding a poor solvent which is in an amount of 1.4 L or more per mol of the glutamic acid benzyl ester N-carboxylic anhydride at a temperature equal to or higher than 40°C and lower than a boiling point thereof, precipitating crystals at a temperature equal to or higher than 40°C and lower than a boiling point thereof, and cooling the crystals.