CN106317256A - Method for preparing chitooligosaccharide from neutral chitosan oligosaccharide - Google Patents
Method for preparing chitooligosaccharide from neutral chitosan oligosaccharide Download PDFInfo
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- CN106317256A CN106317256A CN201510396596.6A CN201510396596A CN106317256A CN 106317256 A CN106317256 A CN 106317256A CN 201510396596 A CN201510396596 A CN 201510396596A CN 106317256 A CN106317256 A CN 106317256A
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Abstract
The invention relates to the technical field of chitosan oligosaccharide preparation, and particularly relates to a method for preparing chitooligosaccharide from neutral chitosan oligosaccharide. The method is characterized by comprising the following steps: (1) adding the raw material chitosan oligosaccharide into an alcohol solution in a dispersing manner; (2) adding an acetylated reagent; (3) stirring to react; (4) separating chitooligosaccharide; and (5) drying chitooligosaccharide solid powder. The method has the advantages that no catalyst is added to serve as an acid transferring agent, so that the selectivity of amino acetylation in the reaction can be realized, products in the reaction system can be easily separated, and the reaction solvent can be recycled, so that the production cost can be reduced, the product quality stability can be improved, and a high-quality chitooligosaccharide product can be prepared.
Description
Technical field
The invention belongs to chitinous oligomers preparing technical field, a kind of method being prepared chitinous oligomers by neutral oligochitosan.
Background technology
Chitin is also chitin, is the macromolecule polysaccharide being formed by connecting by β 1-4 glycosidic bond by n-acetylglucosamine.This natural polymers is widely present in the cell wall of aquatic biological shell, land arthropod shell and fungus and some algae, is a kind of second largest organic regenerative resource being only second to plant cellulose.Chitin is the important raw and processed materials of the aspects such as food, medicine, chemical industry, it is also possible to be manured into soil as biological pesticide, chitinase producing strains secretion chitinase in induction plant and soil, thus strengthens crops and resist the ability of pathogen and insect pest.
But chitin does not dissolves in olefin(e) acid, alkali and general organic solvent, seriously limit its application.Chitinous oligomers, as the low molecule product of degradation of chitin, inherits the multiple physiologically active of chitin, and which overcomes the water-fast shortcoming of chitin, has good moisture retention, antibacterial, antitumor, raising plant resist the functions such as power.Can apply to the fields such as medicine, cosmetics, functional food, biological pesticide, plant stress-resistance agent, there is wide market prospect.
The method that current report prepares chitinous oligomers mainly has chemical method and bioanalysis.Chemical method one is to make glycosidic bond rupture by high concentrated acid, chitin of degrading, and the method is polluted big, big energy-consuming, and equipment requirements is high, subsequent treatment difficulty.Another kind of chemical method, with oligochitosan as raw material, adds acetylation reagent, controlled syntheses chitinous oligomers.But the method needs to add the catalyst such as triethylamine as acid transfer agent, the introducing of catalyst, the extreme difficulties to the separating belt of product.Bioanalysis is to prepare chitinous oligomers with chitinase degraded chitin.Biological enzyme is currently in the laboratory research stage, and enzymolysis efficiency is low, it is impossible to large-scale production.
Summary of the invention
For solving above-mentioned the deficiencies in the prior art, the present invention provides a kind of method being prepared chitinous oligomers by neutral oligochitosan, with neutral oligochitosan as raw material, prepares chitinous oligomers by chemical method.Need not add catalyst as acid transfer agent, by control add acetylation reagent quality, reaction temperature and time, make amino highly selective acylation, and hydroxyl do not occur acetylation.Process of the present invention is simple, and product is easily isolated, it is simple to accomplish scale production.
For achieving the above object, the technical solution adopted in the present invention is, a kind of method being prepared chitinous oligomers by neutral oligochitosan, comprises the steps of:
(1) dispersion of raw material neutrality oligochitosan is joined in ethanol solution；
(2) acetylation reagent is added；
(3) the stirring stage of reaction；
(4) separation of chitinous oligomers；
(5) chitinous oligomers pressed powder is dry.
Further, a kind of method being prepared chitinous oligomers by neutral oligochitosan, described neutral oligochitosan molecular weight is 340-4000, ash≤1%, moisture≤8%, pH value 6-8；The mass fraction of described ethanol solution is 0.1%-30%；
Further; a kind of method being prepared chitinous oligomers by neutral oligochitosan; need reaction solution is stirred dispersion when described step (2) adds acetylation reagent; and addition speed needs slowly; described acetylation reagent is acetic anhydride; purity >=90%, oligochitosan and acetic anhydride mass ratio 1:0.6-1:2.4；
Further, a kind of method being prepared chitinous oligomers by neutral oligochitosan, in described step (3), reaction temperature controls at 0 DEG C-30 DEG C, and the response time is 3h-72h, continuously stirred during reaction；
Further, a kind of method being prepared chitinous oligomers by neutral oligochitosan, in described step (4), the method for described separation includes precipitation, the centrifugal and solid-liquid separating method of filtration；
Further, a kind of method being prepared chitinous oligomers by neutral oligochitosan, in described step (5), described drying means has hot air drying, vacuum drying, heat pump drying, cold air drying, microwave drying and infrared drying, or the combination drying of above drying mode, baking temperature is less than≤50 DEG C.
Present invention also offers a kind of chitinous oligomers product, be to prepare according to a kind of above-mentioned method being prepared chitinous oligomers by neutral oligochitosan.
Main advantages of the present invention are as follows:
(1) using neutral oligochitosan replacement oligochitosan as synthesis material, substituted meaning is, in course of reaction, it is not necessary to add catalyst as acid transfer agent；
(2) acetylated selectivity；Amino is active group, by controlling acetylation reagent consumption, reaction temperature and time, can optionally make acetylated, and hydroxyl does not occur acetylization reaction；
(3) in reaction system, product can be obtained by simple solid-liquid separating method, it is not necessary to other operation separation impurity；
(4) alcohol solvent used in preparation process can be reused, and reduces production cost.
Accompanying drawing explanation
Fig. 1 is chitinous oligomers and the infrared spectrum comparison diagram of neutral oligochitosan in the present invention.
Detailed description of the invention
For making the purpose of the present invention, technical scheme and effect clearer, clear and definite, the present invention is described in more detail below.Should be appreciated that and described herein be embodied as example only in order to explain the present invention, be not intended to limit the present invention.
Embodiment 1:
Take 10g neutrality oligochitosan, molecular weight 1125, deacetylation 90%, join in 100mL ethanol, be slowly added dropwise acetic anhydride 2mL, 0 DEG C of reaction 4h.Filter, filter cake washing with alcohol 2-3 time, 40 DEG C of drying filter cakes.Obtain pale yellow powder 9.24g.Surveying chitinous oligomers molecular weight is 1260, and acetyl degree is 56%.
Embodiment 2:
Take 10g neutrality oligochitosan, molecular weight 1125, deacetylation 90%, join in 150mL ethanol, be slowly added dropwise acetic anhydride 3ml, 20 DEG C of reaction 12h, filter, filter cake washing with alcohol 2-3 time, 40 DEG C of drying filter cakes.Obtain pale yellow powder 9.45g.Surveying chitinous oligomers molecular weight is 1330, and acetyl degree is 70%.
Embodiment 3:
Take 10g neutrality oligochitosan, molecular weight 1125, deacetylation 90%, join in 150mL ethanol, be slowly added dropwise acetic anhydride 4ml, 30 DEG C of reaction 24h, filter, filter cake washing with alcohol 2-3 time, 40 DEG C of drying filter cakes.Obtain pale yellow powder 9.50g.Surveying chitinous oligomers molecular weight is 1400, and acetyl degree is 90%.
Embodiment 4:
Taking 10g neutrality oligochitosan, molecular weight is 3115, deacetylation 85%, adds in 200mL ethanol, is slowly added dropwise acetic anhydride 3mL, 30 DEG C of reaction 10h, filters, filter cake washing with alcohol 2-3 time, 40 DEG C of drying filter cakes.Obtain pale yellow powder 9.32g.Surveying chitinous oligomers molecular weight is 3440, and acetyl degree is 79%.
Embodiment 5:
Taking 10g neutrality oligochitosan, molecular weight is 3115, deacetylation 85%, adds in 400mL ethanol, is slowly added dropwise acetic anhydride 5mL, 30 DEG C of reaction 24h, filters, filter cake washing with alcohol 2-3 time, 40 DEG C of drying filter cakes.Obtain pale yellow powder 9.12g.Surveying chitinous oligomers molecular weight is 3570, and acetyl degree is 95%.
Below the present invention is described in detail, the above, only the preferred embodiments of the invention, when not limiting the scope of the present invention, the most all made impartial change according to the application scope and modified, all should still be belonged in covering scope of the present invention.
Claims (7)
1. the method being prepared chitinous oligomers by neutral oligochitosan, it is characterised in that comprise the steps of: the dispersion of raw material neutrality oligochitosan is joined in ethanol solution by (1)；(2) acetylation reagent is added；(3) the stirring stage of reaction；(4) separation of chitinous oligomers；(5) chitinous oligomers pressed powder is dry.
2. as claimed in claim 1, a kind of method being prepared chitinous oligomers by neutral oligochitosan, it is characterised in that: described neutral oligochitosan molecular weight is 340-4000, and ash≤1%, moisture≤8%, pH value 6-8, the mass fraction of described ethanol solution is 0.1%-30%.
The most as claimed in claim 1; a kind of method being prepared chitinous oligomers by neutral oligochitosan; it is characterized in that: when described step (2) adds acetylation reagent, reaction solution is stirred dispersion; and it is slowly added to acetylation reagent; described acetylation reagent is acetic anhydride; purity >=90%, oligochitosan and acetic anhydride mass ratio 1:0.6-1:2.4.
4. as claimed in claim 1, a kind of method being prepared chitinous oligomers by neutral oligochitosan, it is characterised in that: in described step (3), reaction temperature controls at 0 DEG C-30 DEG C, and the response time is 3h-72h, continuously stirred during reaction.
5. as claimed in claim 1, a kind of method being prepared chitinous oligomers by neutral oligochitosan, it is characterised in that: in described step (4), the method for described separation includes precipitation, the centrifugal and solid-liquid separating method of filtration.
The most as claimed in claim 1, a kind of method being prepared chitinous oligomers by neutral oligochitosan, it is characterized in that: in described step (5), described drying means has the combination drying of one or more drying modes in hot air drying, vacuum drying, heat pump drying, cold air drying, microwave drying and infrared drying, and baking temperature is less than≤50 DEG C.
7. a chitinous oligomers product, it is characterised in that: the method being prepared chitinous oligomers by neutral oligochitosan according to any one described in claim 1 to 6 prepares.
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| CN201510396596.6A CN106317256A (en) | 2015-07-08 | 2015-07-08 | Method for preparing chitooligosaccharide from neutral chitosan oligosaccharide |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2000132A1 (en) * | 2007-06-05 | 2008-12-10 | The Jordanian Pharmaceutical Manufacturing Co. | Solid pharmaceutical formulation |
| CN102993332A (en) * | 2011-12-09 | 2013-03-27 | 中国科学院大连化学物理研究所 | Preparation process of chitin oligose |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2000132A1 (en) * | 2007-06-05 | 2008-12-10 | The Jordanian Pharmaceutical Manufacturing Co. | Solid pharmaceutical formulation |
| CN102993332A (en) * | 2011-12-09 | 2013-03-27 | 中国科学院大连化学物理研究所 | Preparation process of chitin oligose |
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Application publication date: 20170111 |
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