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Maleic acid β-cyclodextrin ester and preparation method thereof

A maleic acid and cyclodextrin technology, applied in the chemical field, can solve the problems of unreported preparation methods, difficult product application, high toxicity, etc.

Inactive Publication Date: 2016-11-02
INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the preparation process, highly active and highly toxic organic reagents such as p-benzoic acid sulfonyl chloride are often used, and it is difficult to apply its products to the fields of food and medicine.
At present, there is no report about the preparation method of maleic acid β-cyclodextrin ester

Method used

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  • Maleic acid β-cyclodextrin ester and preparation method thereof
  • Maleic acid β-cyclodextrin ester and preparation method thereof
  • Maleic acid β-cyclodextrin ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] With 0.636g (0.006mol) sodium hypophosphite (NaH 2 PO 2 ) as a catalyst, 1.393g (0.012mol) maleic acid, 6.81g (0.006mol) β-cyclodextrin and 0.0348g (2.8×10- 4 mol) Inhibitor 4-methoxyphenol (4-Methoxyphenol) was mixed in 5.3g of water and carried out esterification reaction at 110°C for 2.5 hours. After the reaction was completed, the crystal was washed three times with 95% ethanol 100ml, and was washed three times at 60 °C oven-dried to obtain maleic acid β-cyclodextrin monoester represented by formula I provided by the present invention.

Embodiment 2

[0057] With 0.624g (0.004mol) sodium dihydrogen phosphate (NaH 2 PO 4 ) as a catalyst, 0.696g (0.006mol) maleic acid, 6.81g (0.006mol) β-cyclodextrin and 0.0174g (1.40×10 -4 mol) methylhydroquinone (Methylhydroquinone) was mixed in 4.9g of water and then esterified at 100°C for 3.5 hours. After the reaction, the crystals were washed three times with 100ml of 95% ethanol, and dried in an oven at 60°C to obtain this product The β-cyclodextrin monoester of maleic acid represented by the formula I provided by the invention.

Embodiment 3

[0059] With 0.636g (0.006mol) sodium hypophosphite (NaH 2 PO 2 ) as a catalyst, 2.786g (0.024mol) maleic acid, 6.81g (0.006mol) β-cyclodextrin and 0.0209g (1.68×10 -4 mol) 4-methoxyphenol (4-Methoxyphenol) was mixed in 6.1g of water and carried out esterification reaction at 120°C for 1.5 hours. After the reaction was completed, the crystal was washed three times with 100ml of 95% ethanol, and the Oven-dried at 60°C, the maleic acid β-cyclodextrin diester represented by the formula I provided by the present invention was obtained.

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Abstract

The invention discloses a maleic acid [beta]-cyclodextrin ester and a preparation method thereof. A structure general formula of maleic acid [beta]-cyclodextrin monoester is represented as the formula I and a structure general formula of maleic acid [beta]-cyclodextrin diester is represented as the formula II. The method includes a following step of mixing maleic acid, [beta]-cyclodextrin and a polymerization inhibitor for carrying out an esterification reaction with a phosphate as a catalyst to obtain the maleic acid [beta]-cyclodextrin monoester represented as the formula I and / or the maleic acid [beta]-cyclodextrin diester represented as the formula II. The invention provides the environmental-friendly preparation method. In the method, the phosphate is employed as a catalyst and the polyunsaturated carboxylic acid and the [beta]-cyclodextrin are esterified so that not only is usage amount of an organic solvent is reduced but also an unsaturated degree of [beta]-cyclodextrin esterification derivatives is increased, thereby providing a new approach for the [beta]-cyclodextrin derivatives in high-molecular polymer molecule construction.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to an ester material, in particular to a maleic acid β-cyclodextrin ester and a preparation method thereof. Background technique [0002] β-cyclodextrin (β-cyclodextrin, β-CD) is a kind of cyclodextrin, which is a cyclic oligosaccharide composed of 7 D-glucopyranose linked by α-1,4 glycosidic bonds. - Cyclodextrin has a hydrophobic inner cavity, which can provide ideal bonding sites, and can include small organic molecules of a certain size and shape to form a new type of inclusion material. Due to the fixed size of the lumen structure of β-cyclodextrin, the stability of the inclusion compound mainly depends on the polarity and size of the guest molecule. At present, the β-cyclodextrin embedding technology is mainly used for the preparation of inclusion compounds and microcapsules of essential oils, water-insoluble drugs, volatile substances, etc., but because β-cyclodextrin forms an intramol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16
Inventor 哈益明李咏富李庆鹏靳静
Owner INST OF AGRO FOOD SCI & TECH CHINESE ACADEMY OF AGRI SCI
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