Acid-Modified Cyclodextrin via Succinic Acid Esterification

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Solution Overview

Problem

Existing cyclodextrin modification methods require toxic and harmful reagents, making them cumbersome and costly, limiting their application in health industries such as food, medicine, and cosmetics.

Innovation Solution

A green acid-modified cyclodextrin preparation method using a dry-heat reaction with succinic acid and a catalyst, such as sodium hypophosphite, which is simple, fast, and pollution-free, enhancing the cyclodextrin's cavity activity for better guest molecule embedding.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If chemical modification methods are used to improve cyclodextrin embedding effect, then the sensitivity to recognize guest molecules and embedding rate are improved, but toxic and harmful reagents are required and production costs increase

Engineering Contradiction:
Improveembedding rateVSAvoidtoxic reagents
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the modification process by using succinic acid instead of traditional toxic reagents like sulfuric acid or hydrochloric acid. This substitution maintains the esterification reaction effectiveness while eliminating the harmful effects of strong mineral acids, thus improving the embedding rate without introducing toxic reagents into the system

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs succinic acid as a mild, biocompatible reagent that can be easily removed or degraded, replacing persistent toxic reagents. The succinic acid modification allows for effective cyclodextrin modification with reagents that are environmentally friendly and suitable for food and pharmaceutical applications, effectively discarding the need for harmful chemical agents

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

2Reliability

If chemical modification methods are used to improve cyclodextrin embedding effect, then the sensitivity to recognize guest molecules is improved, but the modification process becomes cumbersome and production costs increase

Engineering Contradiction:
Improvesensitivity to recognize guest moleculesVSAvoidmodification process complexity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent modifies the reaction conditions by using mild heating (40-100°C) and simple stirring instead of complex multi-step procedures requiring sophisticated equipment. The succinic acid modification process operates under gentle conditions that simplify the manufacturing process while maintaining high sensitivity for guest molecule recognition through effective esterification

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The modification process allows the cyclodextrin-succinic acid system to self-organize and react efficiently under simple conditions. The mild heating and stirring enable the reaction to proceed effectively without requiring complex catalysts or multi-stage processing, making the manufacturing process more straightforward and easier to control

Inventive Principle:
Principle #25Self-service

3Quantity of substance

If traditional chemical modification is used, then cyclodextrin can be modified, but toxic reagents need to be additionally removed resulting in higher production costs

Engineering Contradiction:
Improvecyclodextrin modificationVSAvoidreagent removal cost
Core Design Contradiction:
Quantity of substanceVSLoss of substance

Solution Approach 1:

The patent uses succinic acid as a temporary modifying agent that serves its purpose during the modification process and then can be easily removed or remains as a benign component. The succinic acid groups introduced during modification do not require expensive removal processes like traditional toxic reagents, eliminating the need for additional purification steps and reducing production costs

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

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 cyclodextrin derivatives with improved embedding efficiency and water solubility, allowing for higher loading capacities and stability, as demonstrated by the successful embedding of curcumin, with enhanced retention rates over time.

Implementation Method 1

The present disclosure adopts a dry-heat reaction method to promote the smooth progress of an esterification reaction

Methodology Applied
Scientific EffectEsterification reaction: Chemical Bonding

Implementation Method 2

The method uses succinic acid, cyclodextrin and catalyst as raw materials, and the raw materials undergo uniform mixing, a dry-heat reaction

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 3

performing a dry-heat reaction of the mixture obtained in step (1) at a high temperature or under a microwave action

Methodology Applied
Scientific EffectThermal energy: Heating

Implementation Method 4

adding anhydrous ethanol to precipitate the acid-modified cyclodextrin, and washing

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Data Source

PatentUS11840584B2Simple and green method for preparation of acid modified cyclodextrin
Publication Date: 2023.12.12 JIANGNAN UNIV
  • US11840584B2 patent drawing
  • US11840584B2 patent drawing
  • US11840584B2 patent drawing

AI summary

The present disclosure discloses a simple preparation method of green acid-modified cyclodextrin, belonging to the field of cyclodextrin modification. Cyclodextrin and succinic acid are mutually modified by an esterification reaction in the presence of catalyst, and acid-modified cyclodextrin with different modification degrees is obtained by controlling reaction time at a high temperature or under a microwave action. The prepared modified cyclodextrin does not involve the use of toxic and harmful reagents, the modification reaction is simple, green and controllable, and the loading capacity of the modified cyclodextrin to guest molecules is remarkably improved compared with the loading capacity of the original cyclodextrin, so that the modified cyclodextrin has great application potential in the health fields such as food, medicines, and cosmetics.