Ceramide Purification via Hydrocarbon Solvent Crystallization
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Solution Overview
Problem
Current methods for producing ceramide are not industrially advantageous due to low yield, poor crystal separation efficiency, and difficulty in removing solvents like butanol, resulting in ceramide of low purity and high bulk density.
Innovation Solution
A method involving N-acylation reaction of an optically active aminodiol using an aliphatic hydrocarbon solvent, followed by addition of an aliphatic saturated alcohol to precipitate crystals, allowing for high-purity ceramide production with high diastereomeric purity and yield, and simple purification procedures.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If butanol is used as a solvent for ceramide production, then the ceramide can be produced, but the butanol remains in the product and is very difficult to remove, resulting in low purity
Solution Approach 1:
The patent changes the solvent parameter from butanol to a hydrocarbon solvent (hexane, heptane, octane, or cyclohexane). This parameter change fundamentally alters the solubility characteristics, allowing ceramide to crystallize in high purity without retaining the solvent, thereby resolving the contradiction between production and purity
Solution Approach 2:
The patent utilizes phase transition by cooling the reaction mixture to precipitate ceramide crystals. The ceramide transitions from dissolved state to crystalline solid state, while the hydrocarbon solvent remains in liquid phase and can be easily separated, achieving high purity without difficult solvent removal
2Quantity of substance
If ethyl acetate is used as a solvent for ceramide production, then the reaction can proceed, but a cumbersome washing procedure needs to be repeated after the reaction, reducing productivity
Solution Approach 1:
The patent changes the solvent from ethyl acetate to hydrocarbon solvents, which fundamentally alters the crystallization behavior. The ceramide crystallizes directly from the hydrocarbon solvent without requiring additional washing steps, eliminating the cumbersome purification procedure and improving productivity
Solution Approach 2:
The patent extracts the ceramide product directly as pure crystals from the hydrocarbon solvent system. The crystals separate cleanly without adhering solvent or impurities that would require washing, allowing direct filtration and drying to achieve high purity product
3Manufacturing precision
If methanol is used for recrystallization to purify ceramide, then the purity can be improved, but the method is not industrially advantageous due to low yield and complex procedures
Solution Approach 1:
The patent changes the recrystallization solvent from methanol to hydrocarbon solvents. This parameter change enables direct crystallization from the reaction medium, eliminating the need for separate recrystallization steps and achieving both high purity and high yield in a single operation suitable for industrial scale-up
Solution Approach 2:
The patent merges the reaction and purification steps into a single integrated process. The ceramide crystallizes directly from the hydrocarbon solvent reaction mixture, combining synthesis and purification into one operation, thereby improving both yield and industrial scalability
4Quantity of substance
If conventional methods are used for ceramide crystal separation, then the process can proceed, but the crystal separation efficiency is poor, resulting in low purity and high bulk density
Solution Approach 1:
The patent changes the solvent system to hydrocarbons, which fundamentally alters the crystal formation characteristics. The ceramide forms well-defined crystals with low bulk density that separate efficiently by filtration, achieving both high purity and good physical properties without requiring advanced separation techniques
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-purity ceramide production with improved yield and reduced bulk density, suitable for cosmetic applications and industrial scalability, eliminating the need for cumbersome solvent removal processes.
Implementation Method 1
adding an aliphatic, saturated alcohol having 1 to 3 carbon atoms into the reaction mixture in which a crude ceramide represented by the following general formula (1) generated in the preceding process is dissolved
Data Source
AI summary
Provided is a method for producing an optically active ceramide by an N-acylation (amidation) reaction of an optically active aminodiol, wherein a crude ceramide produced therein is purified by an industrially advantageous process. Namely, provided is a method for producing a high-purity ceramide that has high diastereo purity with high yield. A high-purity ceramide is produced by: a step wherein a ceramide represented by general formula (1) is produced by reacting an aminodiol with an alkyl ester having 1-5 carbon atoms of an aliphatic carboxylic acid having 12-24 carbon atoms, said aliphatic carboxylic acid optionally having a hydroxyl group, in a hydrocarbon solvent having 5-10 carbon atoms; and a step wherein an alcohol having 1-3 carbon atoms is added into the reaction mixture obtained in the preceding step, thereby causing crystals to precipitate. (In the formula, R1 represents an alkyl group which has 13-17 carbon atoms and optionally has a carbon-carbon unsaturated bond; R2 represents an alkyl group which has 11-23 carbon atoms and optionally has a hydroxyl group; and * represents an optically active state.)