Chitosan-bi(aryl-carbamate)-(amide) and preparation method thereof

A technology of aromatic carbamate and chitosan, which is applied in the field of chitosan-di- and its preparation, can solve the problem that the stationary phase is not long in service life, and the organic solvent cannot be used as a flow equalization, and is beneficial to hand Character recognition, strong chiral separation performance, and structural regularity

Inactive Publication Date: 2015-01-28
WUHAN INSTITUTE OF TECHNOLOGY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of stationary phase also has the following problems: ①The polysaccharide derivatives on some coated stationary phases are soluble in the organic mobile phase, or highly swellable in the mobile phase, so the service life of the stationary phase is not long, and some organic Solvents cannot be used as mobile phase components[⑹.Ikai T.,Yamamoto C.,Kamigaito M.,Okamoto Y.,Immobilization of polysaccharide derivatives onto silica gel-Facile synthesis of chiral packing materials by means of intermolecular polycondensation of triethoxysilyl groups , Journal of Chromatography A, 1157, 151–158, 2007]
[0005] In conclusion, so far, the coated polysaccharide derivative chiral stationary phase still faces the problem of ensuring superior separation performance and being able to be used in a wide range of organic solvent mobile phases

Method used

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  • Chitosan-bi(aryl-carbamate)-(amide) and preparation method thereof
  • Chitosan-bi(aryl-carbamate)-(amide) and preparation method thereof
  • Chitosan-bi(aryl-carbamate)-(amide) and preparation method thereof

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preparation example Construction

[0060] Preparation of chitosan:

[0061] Grind the purchased flake chitin (shrimp shell) with a pulverizer, sieve (355 μm), collect the chitin under the sieve as raw material, and use two methods to deacetylate chitin (document 14-16); and use Chitosan can be degraded by hydrogen peroxide (References 17 and 18), and chitosan with different molecular weights can be obtained by adjusting the concentration of hydrogen peroxide and the reaction temperature. After degradation, the degree of deacetylation of chitosan remained basically unchanged.

[0062] Preparation of chitosan with n-pentanol as solvent:

[0063] Weigh 20g of dried chitin into a three-necked flask, add NaOH and n-pentanol according to chitosan / NaOH / n-pentanol=1 / 5 / 11 (mass ratio), heat to reflux for 3h, filter, and wash with water until medium properties, drying to obtain 13.64g white solid, yield 86%; its 1 H NMR diagram is attached figure 1 As shown in (I), 1 H NMR (CF 3 COOD, δ / ppm): 5.78-3.24 (H on the gl...

Embodiment 1

[0070] Synthesis of Chitosan-bis(3-methylphenylcarbamate)-(isobutyramide)

[0071] Preparation of N-isobutyrylated chitosan: 1.50g (9.32mol repeating unit) chitosan (number average molecular weight 60,000, deacetylation degree 98.2%) was added in a 250mL three-necked flask, and 0.75g isobutyric acid was added Butyric acid and 30g distilled water, stir to make chitosan dissolve until clear and transparent. Then add 70mL of methanol, after mechanical stirring, quickly add 8.84g (55.92mmol) of isobutyric anhydride (the molar ratio of anhydride to chitosan repeating unit is 6:1) and 80mL of methanol, and react at 16°C for 7h. After the reaction is complete, pour the reaction solution into 240mL 0.5mol / L KOH-ethanol solution, stir for two hours, let stand overnight, filter, wash the product with ethanol and water until neutral, and dry to obtain 2.01g of N-isobutyl Acylated chitosan, yield: 93%; infrared spectrogram as attached figure 2 (I) shown: IR (KBr, cm -1 )υ: 3523-3254(-...

Embodiment 2

[0075] Synthesis of Chitosan-bis(3-chloro-4-methylphenylcarbamate)-(cyclobutylformamide)

[0076] The preparation of N-cyclobutylformyl chitosan: 1.0g (6.21mmol repeat unit) chitosan (number average molecular weight 32,000, deacetylation degree 98.0%) is added in the 250mL three-necked flask, adds 0.60g cyclobutyl formic acid, 20g of distilled water, stirred to dissolve the chitosan until clear and transparent. Add 30mL of methanol, stir mechanically, then quickly add 7.92g (43.47mmol) cyclobutyl formic anhydride (the molar ratio of anhydride to chitosan repeating unit is 7:1) and 70mL of methanol, and react at 25°C for 7h. After the reaction was completed, the reaction solution was poured into 185 mL of 0.5 mol / L KOH-ethanol solution, stirred for two hours, and left to stand overnight. Filter, wash the product to neutrality with ethanol and water, dry, obtain 1.37g N-cyclobutylated chitosan, productive rate: 91%; Its infrared spectrogram is as attached figure 2 Shown in (I...

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Abstract

The invention relates to a material chitosan-bi(aryl-carbamate)-(amide) for preparing a chiral stationary phase and a preparation method of the chitosan-bi(aryl-carbamate)-(amide). The preparation method comprises the following steps: 1) acylating chitosan amino, namely enabling chitosan with the deacetylation degree of over 98 percent to be reacted with excessive anhydride, thereby obtaining acylated N-chitosan; and 2) performing carbamic acid esterification on acylated N-chitosan, namely dissolving the acylated N-chitosan in N,N-dimethylacetamide solution of lithium chloride, adding excessive isocyanate containing different substituent groups on the benzene ring, and reacting at the temperature of 80-95 DEG C for 24-36 hours, thereby generating a chitosan derivative, namely the chitosan-bi(aryl-carbamate)-(amide). The structural formula is as shown in the specification.

Description

technical field [0001] The invention relates to a functional material for chiral separation, in particular to chitosan-bis(aryl carbamate)-(amide) and a preparation method thereof. Background technique [0002] Many natural phenomena are related to the chirality of molecules. For example, chiral polymers have special optical and electrical properties, and some chiral small molecule enantiomers used as medicines have great differences in physiological activities. One enantiomer can effectively Therefore, the preparation, separation and detection of chiral molecules have become a hot research field. In addition to asymmetric synthesis and biocatalytic chiral synthesis, liquid chromatography based on the use of chiral stationary phase (Chiral Stationary Phase, CSP) is an effective method for batch separation of enantiomers [⑴.Hsu L.C., Kim H ., Yang X., et al, Large scale chiral chromatography for the separation of an enantiomer to accelerate drug development, Chirality, 23, 3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
Inventor 柏正武王晓晨黄少华陈伟张娟宾琴罗迎彬王昭群刘建德付克勤吴瑞刘涛冯子维
Owner WUHAN INSTITUTE OF TECHNOLOGY
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