Synthesis method of sulfobutyl ether-beta-cyclodextrin with specific average substitution degree

A technology of sulfobutyl ether and cyclodextrin, which is applied in the field of synthesis of sulfobutyl ether-β-cyclodextrin, can solve the problems of low yield, harsh reaction conditions, environmental pollution, etc., and improve the reaction yield , mild reaction conditions, simple post-treatment effect

Active Publication Date: 2015-09-09
TIANJIN UNIV
View PDF7 Cites 20 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method of sulfobutyl ether-β-cyclodextrin has been reported at present: U.S. Patent US5134127 adopts the method for synthesizing sulfobutyl ether-β-cyclodextrin in water solvent for the first time, utilizes the glucose unit of β-cyclodextrin The hydroxyl groups on the 2, 3, and 6 carbons undergo substitution reactions with 1,4-butane sultone in alkaline solutions to obtain products with a single degree of substitution and multiple degrees of substitution. The disadvantage lies in the degree of substitution of products with multiple substitutions The scope is wide; U.S. Patent US6153746 improves this method, obtains the product that the degree of substitution is 6.6-7.1, and the yield is 50-80%, and its disadvantage is that the yield of the product is low and unstable; Chinese patent CN1858071A uses Metal sodium captures the hydrogen on the hydroxyl group of β-cyclodextrin in the organic solvent 1,4-dioxane to produce more

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of sulfobutyl ether-beta-cyclodextrin with specific average substitution degree
  • Synthesis method of sulfobutyl ether-beta-cyclodextrin with specific average substitution degree
  • Synthesis method of sulfobutyl ether-beta-cyclodextrin with specific average substitution degree

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027] Example 1

[0028] The method for synthesizing sulfobutyl ether-β-cyclodextrin with an average degree of substitution of 1 includes the following steps:

[0029] (1) In a 100mL three-neck flask, under stirring conditions, dissolve 10g β-cyclodextrin in 3.8mL 15%wt NaOH aqueous solution, NaOH is 1.6 times the molar amount of β-cyclodextrin, and the reaction temperature is controlled to 65℃ , Stir for 30min;

[0030] (2) Add 1.8mL 1,4-butane sultone dropwise to a 100mL three-necked flask, the amount of 1,4-butane sultone is twice the molar amount of β-cyclodextrin, and reflux at 65°C for ether When the pH drops to 8.8, adjust the pH of the solution by adding a 15% wt NaOH aqueous solution in the sampler to keep the pH of the reaction system between 8.80-9.70. When the pH of the reaction system is 8.80-9.70 There is no change between the time, add all the remaining NaOH aqueous solution in the sampler and continue the reaction for 6h; the NaOH in the sampler is 0.6 times the mo...

Example Embodiment

[0032] Example 2

[0033] The specific synthetic method of sulfobutyl ether-β-cyclodextrin with an average degree of substitution of 3.4-4.2 includes the following steps:

[0034] (1) In a 100mL three-necked flask, under stirring conditions, dissolve 10g of β-cyclodextrin in 11.5mL of 12.5%wt NaOH aqueous solution. The amount of NaOH added is 4 times the molar amount of β-cyclodextrin, and the reaction temperature is controlled. 75°C, stirring time 30min;

[0035] (2) Add 4.5 mL of 1,4-butane sultone dropwise to a 100 mL three-necked flask. The amount of 1,4-butane sultone added is 5 times the molar amount of β-cyclodextrin, and it is refluxed at 75°C In the etherification reaction, when the pH drops to 8.8, adjust the pH of the solution by using a 12.5% ​​wt NaOH aqueous solution in the sampler to maintain the pH of the reaction system between 8.80 and 9.70. When the pH of the reaction system is 8.80- No change occurs between 9.70, add all the remaining NaOH aqueous solution in th...

Example Embodiment

[0037] Example 3

[0038] The specific synthesis method of sulfobutyl ether-β-cyclodextrin with an average degree of substitution of 6.2-6.9 includes the following steps:

[0039] (1) In a 100mL three-necked flask, under stirring conditions, dissolve 10g of β-cyclodextrin in 18.3mL of 12.5%wt NaOH aqueous solution. The amount of NaOH added is 6.5 times the molar amount of β-cyclodextrin, and the reaction temperature is controlled to 70 ℃, stirring time 30min;

[0040] (2) Add 7.2mL 1,4-butane sultone dropwise to a 100mL three-necked flask, the addition amount of 1,4-butane sultone is 8 times the molar amount of β-cyclodextrin, and perform reflux at 70°C Etherification reaction, when the pH drops to 8.8, adjust the pH of the solution through the 12.5%wt NaOH aqueous solution installed in the pH automatic balancer to keep the pH of the reaction system between 8.80-9.70, when the pH of the reaction system is 8.80 No change occurs between -9.70, add all the remaining NaOH aqueous solut...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a synthesis method of sulfobutyl ether-beta-cyclodextrin with a specific average substitution degree. The synthesis method comprises the following steps: (1) dissolving beta-cyclodextrin into NaOH solution while stirring, wherein the use amount of NaOH solution is 1.6-6.5 times as much as the molar quantity of beta-cyclodextrin; (2) dropwise adding 1,4-butyl sultone and performing reflux etherification; when pH value drops to 8.8, adding NaOH solution to adjust the pH value to be between 8.80-9.70 until the pH value does not change; and then adding all residual NaOH aqueous solution into a reaction container from a sample injector; and (3) when detecting that the mass of residual beta-cyclodextrin in the reaction container is 1% or below, adding NaOH solution, wherein the use amount of NaOH solution is 0.4-1.5 times as much as the molar quantity of beta-cyclodextrin. By the synthesis method, a sulfobutyl ether-beta-cyclodextrin product with a specific average substitution degree can be obtained and the yield is high; in addition, the specific average substitution degree range of the synthesis product is concentrated and the composition of the product is in strict normal distribution; the reaction conditions are mild and post-treatment is simple.

Description

technical field [0001] The invention relates to a synthesis method of sulfobutyl ether-beta-cyclodextrin, and belongs to the fields of synthesis of cyclodextrin derivatives, molecular recognition, chiral resolution and pharmaceutical auxiliary materials. Background technique [0002] Cyclodextrin (CD for short) is a cyclic oligosaccharide formed by the action of cyclodextrin glycosyltransferase on starch. It has a hydrophilic appearance and a hydrophobic inner cavity. The shape is wide at the top and narrow at the bottom. The spatial structure of the three-dimensional configuration of the ring-shaped hollow cone barrel with two ends open. This unique molecular structure enables cyclodextrin to form supramolecular inclusion complexes with guest molecules and change the physical and chemical properties of guest molecules. Therefore, cyclodextrin has become a cheap, easy-to-obtain and biocompatible compound in supramolecular chemistry. It is an important host molecule and is w...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C08B37/16
Inventor 张毅民马冬雅徐景娜李夏阳
Owner TIANJIN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap