CN105399862B - A kind of preparation method of chitosan acetate - Google Patents
A kind of preparation method of chitosan acetate Download PDFInfo
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- CN105399862B CN105399862B CN201510929915.5A CN201510929915A CN105399862B CN 105399862 B CN105399862 B CN 105399862B CN 201510929915 A CN201510929915 A CN 201510929915A CN 105399862 B CN105399862 B CN 105399862B
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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Abstract
The present invention relates to a kind of preparation methods of chitosan acetate, belong to technical field of biological material, method is that chitosan is made fully to be reacted with glacial acetic acid, thionyl chloride first, in the C of chitosan2‑NH2And C6Acetate ion (CH is introduced on OH simultaneously respectively3COO‑) and acetyl group (CH3CO), intermediate product is prepared, ammonium hydroxide reduction C is then added dropwise2‑NH2, chitosan acetate is prepared, protection amino is eliminated and finally sloughs the tedious steps of protecting group, method is simple and effective, and reduces the wasting of resources, reduces the chance for introducing unnecessary group.The present invention has wide applicability to raw material chitosan.The present invention has good application and development prospect in many fields such as medicine, food, agricultural, cosmetics, and therefore, the technology of the present invention has stronger potentiality of economical exploit.
Description
Technical field
The invention belongs to technical field of biological material, are related to a kind of preparation method of chitosan acetate.
Background technology
Chitosan is unique polycation polysaccharide in nature, has non-toxic, good biocompatibility, biology can
Degradability and broad-spectrum antibacterial, therefore all obtained in numerous areas such as pharmaceutics, biotechnology, cosmetics, agricultural and Food Sciences
To being widely applied.However, the compact crystalline structure of chitosan makes its main active group C2-NH2It cannot play well
Effect, limits its application to a certain extent.To the C of chitosan6- OH is modified, and new base is introduced by esterification
Group, while retentive activity C2-NH2Group, and the crystalline structure of chitosan is destroyed, its application range can be expanded.
According to the literature, 2 kinds of methods mainly prepare Chitosan Ester at present：Method one is that chitosan and acid are directly anti-
Should, catalyst is made with sulfuric acid, the disadvantages of this method is reaction temperature height, and degree of substitution is low；Method second is that protect amino, then first
Prepare acyl chlorides and hydroxyl reaction, amino is deprotected after reaction, and the disadvantages of this method is that reaction is complicated, and can use it is a variety of right
The reagent that environment is harmful to.
Invention content
The purpose of the present invention is to provide a kind of preparation method of chitosan acetate, to make up the deficiency of original technology.
The technical solution adopted by the present invention is that：
The preparation method of the chitosan acetate of the present invention is as follows：
(1) using chitosan as raw material, make itself and glacial acetic acid, the abundant mixing of thionyl chloride, seal, ultrasound (35~53kHz,
250~500W) it handles 40-80 minutes, mixture is made fully to react；
(2) reaction system is cooled to room temperature, adds in the intermediate product precipitation that absolute ethyl alcohol generates reaction, filter, receive
Collect intermediate product, intermediate product is dissolved in suitable deionized water, obtains the aqueous solution of intermediate product；
(3) ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitations, it is heavy to be collected by centrifugation
It forms sediment, and precipitation is washed with deionized 4-6 times；
(4) precipitation is dried at 18-24 hours, 30-60 DEG C to get chitosan acetate with absolute ethyl alcohol soxhlet type.
In step (1), chitosan：Glacial acetic acid：Thionyl chloride=1~3：6~10：3~5 (m：v：v)；The purity of glacial acetic acid
＞ 99%.
In step (2), the addition of absolute ethyl alcohol is 5~8 times of reaction system volume, during the addition of deionized water is
Between product 20~25 times of (v：m).
The positive effect of the present invention is as follows：
The present invention uses single step reaction method in the C of chitosan2-NH2And C6Acetate ion is introduced on-OH respectively
(CH3COO-) and acetyl group (CH3CO-), intermediate product is prepared, ammonium hydroxide reduction C is then added dropwise2-NH2, chitosan acetate is prepared,
It eliminates protection amino and finally sloughs the tedious steps of protecting group, method is simple and effective, and reduces the wasting of resources, reduces
Introduce the chance of unnecessary group.The present invention has wide applicability to raw material chitosan.The present invention medicine, food,
Many fields such as agricultural, cosmetics have good application and development prospect, and therefore, there is the technology of the present invention stronger economy to open
Send out potentiality.
Specific embodiment：
(1) using chitosan as raw material, make itself and glacial acetic acid, the abundant mixing of thionyl chloride, seal, ultrasound (35~53kHz,
250~500W) it handles 40-80 minutes, mixture is made fully to react；
(2) reaction system is cooled to room temperature, adds in the intermediate product precipitation that absolute ethyl alcohol generates reaction, filter, receive
Collect intermediate product, intermediate product is dissolved in suitable deionized water, obtains the aqueous solution of intermediate product；
(3) ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitations, it is heavy to be collected by centrifugation
It forms sediment, and precipitation is washed with deionized 4-6 times；
(4) precipitation is dried at 18-24 hours, 30-60 DEG C to get chitosan acetate with absolute ethyl alcohol soxhlet type.
In step (1), chitosan：Glacial acetic acid：Thionyl chloride=1~3：6~10：3~5 (m：v：v)；The purity of glacial acetic acid
＞ 99%.
In step (2), the addition of absolute ethyl alcohol is 5~8 times of reaction system volume, during the addition of deionized water is
Between product 20~25 times of (v：m).
Following specific embodiment further provides the preparation method of the present invention.
Embodiment 1.
By 2g chitosans, 8mL glacial acetic acid (purity ＞ 99%) and the abundant mixing of 3.5mL thionyl chlorides, sealing, ultrasound
(53kHz, 250W) is handled 60 minutes, and mixture is made fully to react；Reaction system is cooled to room temperature, adds in 65mL absolute ethyl alcohols
Make the intermediate product precipitation that reaction generates, filter, collect intermediate product, intermediate product is dissolved in 45mL deionized waters, is obtained
The aqueous solution of intermediate product；The ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitation, centrifugation
Precipitation is collected, and precipitation is washed with deionized 4 times；Precipitation is dried with absolute ethyl alcohol soxhlet type at 20 hours, 40 DEG C, is obtained light
Yellow powder chitosan acetate.
Embodiment 2.
By 5g chitosans, 15mL glacial acetic acid (purity ＞ 99%) and the abundant mixing of 7.2mL thionyl chlorides, sealing, ultrasound
(53kHz, 300W) is handled 50 minutes, and mixture is made fully to react；Reaction system is cooled to room temperature, adds in the anhydrous second of 140mL
Alcohol makes the intermediate product precipitation that reaction generates, and filters, collects intermediate product, intermediate product is dissolved in 115mL deionized waters,
Obtain the aqueous solution of intermediate product；The ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitation, from
The heart collects precipitation, and precipitation is washed with deionized 4 times；Precipitation is dried with absolute ethyl alcohol soxhlet type at 18 hours, 30 DEG C, is obtained
Pale yellow powder shape chitosan acetate.
Embodiment 3.
By 3g chitosans, 12mL glacial acetic acid (purity ＞ 99%) and the abundant mixing of 5.1mL thionyl chlorides, sealing, ultrasound
(35kHz, 350W) is handled 70 minutes, and mixture is made fully to react；Reaction system is cooled to room temperature, adds in the anhydrous second of 100mL
Alcohol makes the intermediate product precipitation that reaction generates, and filters, collects intermediate product, intermediate product is dissolved in 65mL deionized waters,
Obtain the aqueous solution of intermediate product；The ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitation, from
The heart collects precipitation, and precipitation is washed with deionized 4 times；Precipitation is dried with absolute ethyl alcohol soxhlet type at 24 hours, 60 DEG C, is obtained
Pale yellow powder shape chitosan acetate.
Embodiment 4.
By 10g chitosans, 35mL glacial acetic acid (purity ＞ 99%) and the abundant mixing of 15.6mL thionyl chlorides, sealing, ultrasound
(35kHz, 300W) is handled 60 minutes, and mixture is made fully to react；Reaction system is cooled to room temperature, adds in the anhydrous second of 300mL
Alcohol makes the intermediate product precipitation that reaction generates, and filters, collects intermediate product, intermediate product is dissolved in 260mL deionized waters,
Obtain the aqueous solution of intermediate product；The ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitation, from
The heart collects precipitation, and precipitation is washed with deionized 6 times；Precipitation is dried with absolute ethyl alcohol soxhlet type at 20 hours, 50 DEG C, is obtained
Pale yellow powder shape chitosan acetate.
Claims (2)
1. a kind of preparation method of chitosan acetate, it is characterised in that the method is as follows：
Step 1, using chitosan as raw material, make itself and glacial acetic acid, the abundant mixing of thionyl chloride, seal, ultrasound 35~53kHz, 250
~500W is handled 40-80 minutes, and mixture is made fully to react；
Step 2, reaction system is cooled to room temperature, adds in the intermediate product precipitation that absolute ethyl alcohol generates reaction, filter, collect
Intermediate product is dissolved in suitable deionized water by intermediate product, obtains the aqueous solution of intermediate product；
Step 3, the ammonium hydroxide of 1mol/L is added dropwise into the aqueous solution of intermediate product, until there is no Precipitations, it is heavy to be collected by centrifugation
It forms sediment, and precipitation is washed with deionized 4-6 times；
Step 4, precipitation is dried at 18-24 hours, 30-60 DEG C to get chitosan acetate with absolute ethyl alcohol soxhlet type；
In step 1, chitosan：Glacial acetic acid：Thionyl chloride=1~3：6~10：3~5, ratio unit is m：v：v；Glacial acetic acid
Purity ＞ 99%.
2. the preparation method of chitosan acetate as described in claim 1, it is characterised in that in step 2, absolute ethyl alcohol adds
Enter 5~8 times that amount is reaction system volume, the addition of deionized water is 20~25 times of intermediate product.
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| CN114982822B (en) * | 2022-05-17 | 2024-02-23 | 华南理工大学 | Chitosan oligosaccharide cinnamic acid ester and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101649005A (en) * | 2009-09-09 | 2010-02-17 | 中国海洋大学 | Para aminobenzoyl chitosan and preparing method thereof |
| CN102268103A (en) * | 2011-09-02 | 2011-12-07 | 中国海洋大学 | Method for preparing chitosan acetate |
| CN102399304A (en) * | 2011-07-22 | 2012-04-04 | 中国科学院烟台海岸带研究所 | Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof |
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2015
- 2015-12-11 CN CN201510929915.5A patent/CN105399862B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101649005A (en) * | 2009-09-09 | 2010-02-17 | 中国海洋大学 | Para aminobenzoyl chitosan and preparing method thereof |
| CN102399304A (en) * | 2011-07-22 | 2012-04-04 | 中国科学院烟台海岸带研究所 | Chitosan quaternary amine salt gallate, synthetic method thereof and application thereof |
| CN102268103A (en) * | 2011-09-02 | 2011-12-07 | 中国海洋大学 | Method for preparing chitosan acetate |
Non-Patent Citations (1)
| Title |
|---|
| Preparation, characterization and antibacterial activity of O-acetyl-chitosan-N-2-hydroxypropyl trimethyl ammonium chloride;Cai Jinping等;《International Journal of Biological Macromolecules》;20150617;第80卷;第8–15页 * |
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