Solid Acid Catalyst for Aliphatic Glycoside Synthesis

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Solution Overview

Problem

Current methods for producing aliphatic glycoside and sugar fatty acid ester compounds suffer from side reactions, such as condensation and decomposition, leading to reduced purity and increased by-production, requiring complex purification steps and resulting in color deterioration.

Innovation Solution

The method involves using an intramolecularly dehydrated sugar in an addition reaction with an alcohol or carboxylic acid compound in the presence of a solid acid catalyst, specifically a cation exchanger, to suppress side reactions and achieve high-purity compounds with a high conversion ratio.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If a homogeneous phase acid catalyst is used to increase reaction ratio, then the reaction temperature is increased to 100°C or higher and reduced pressure is applied to remove water or lower alcohol, but side reactions such as polymerization of sugar and decomposition reactions occur, causing color deterioration and decreased purity

Engineering Contradiction:
Improvereaction ratioVSAvoidpurity of reaction product
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention changes the reaction parameters by using a solid acid catalyst instead of a homogeneous phase acid catalyst, and by conducting the reaction at lower temperature (below 100°C) and atmospheric pressure. This parameter change suppresses side reactions such as polymerization and decomposition of sugar, thereby improving the purity of the reaction product while maintaining acceptable reaction ratio

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces a solid acid catalyst as an intermediary substance that mediates the reaction between sugar and alcohol. The solid acid catalyst provides acidic sites for catalysis while being easily separable from the reaction mixture, thus enabling the reaction to proceed at lower temperature and pressure without causing color deterioration or generating harmful by-products

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If high temperature and reduced pressure are applied to remove water or lower alcohol, then the reaction ratio is increased, but the load of purification step to remove unreacted substances and by-products increases

Engineering Contradiction:
Improvereaction ratioVSAvoidpurification step
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The solid acid catalyst serves as an intermediary that enables the reaction to proceed under milder conditions (lower temperature and atmospheric pressure), which in turn reduces the formation of by-products and simplifies the purification process. The catalyst can be easily separated from the reaction mixture, eliminating the need for complex purification steps

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention converts the harmful effect of requiring high temperature and pressure to achieve good reaction ratio into a benefit by using a solid acid catalyst that enables the reaction to proceed under mild conditions. This approach not only simplifies the purification process but also eliminates color deterioration and reduces by-product formation

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Productivity

If homogeneous phase acid catalyst is used, then reaction ratio is increased, but by-products with different glycoside bond positions are produced, decreasing product purity

Engineering Contradiction:
Improvereaction ratioVSAvoidpurity of reaction product
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The invention changes the catalytic system from homogeneous phase acid to solid acid catalyst, which fundamentally alters the reaction conditions to lower temperature and atmospheric pressure. This parameter change provides better control over the reaction process, preventing the formation of by-products with different glycoside bond positions and thereby improving product purity

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 approach effectively reduces side reactions, enhances purity, and simplifies the production process by minimizing by-production and coloration, resulting in high-purity aliphatic glycoside and sugar fatty acid ester compounds with improved yield.

Implementation Method 1

subjecting an intramolecularly dehydrated sugar and an alcohol or carboxylic acid compound of an aliphatic hydrocarbon to an addition reaction in the presence of an acid catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the acid catalyst is a solid acid catalyst, specifically a cation exchanger

Methodology Applied
Scientific EffectIon Exchange: Ion Exchange

Data Source

PatentUS20230167147A1Method of producing aliphatic glycoside compound or sugar fatty acid ester compound
Publication Date: 2023.06.01 TOHOKU UNIV
  • US20230167147A1 patent drawing
  • US20230167147A1 patent drawing

AI summary

Provided is a method of producing an aliphatic glycoside compound or a sugar fatty acid ester compound by subjecting an intramolecularly dehydrated sugar and an alcohol or carboxylic acid compound of an aliphatic hydrocarbon to an addition reaction in the presence of an acid catalyst.