Cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate and preparation method of cellulose derivative

A technology of cyclohexyl carbamate and phenyl carbamate, applied in the field of preparation of cellulose derivatives, can solve problems such as poor chiral recognition ability, and achieve the effects of simple operation, mature technology and high yield

Inactive Publication Date: 2013-06-26
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, polysaccharide derivatives with aromatic ring substituents mainly have good chiral recognition and resolution performance for aromatic chiral compounds, while the chiral recognition ability for non-aromatic compounds without phenyl poor

Method used

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  • Cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate and preparation method of cellulose derivative
  • Cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate and preparation method of cellulose derivative
  • Cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate and preparation method of cellulose derivative

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Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0029] 1. Take 0.2g of microcrystalline cellulose and vacuum-dry at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 12h; add 0.4g of lithium chloride after cooling to room temperature; continue to stir for 2h Afterwards, heat up to 70°C again, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 4h, stop the reaction after continuing to stir and reflux for 24h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C To constant weight, the yield was 85%.

[0030] 2. Continue vacuum drying the above intermediate product at 80°C for 4h, then reflux in anhydrous pyridine for 2h, add excess 3,5-dimethylphenylisocyanate, continue to reflux at 80°C for 16h, then stop the reaction , washed well with methanol and dried in vacuo.

[0031] 3. The intermediate product obtained in the previous step was dissolved in a tetrahydrofuran solution containing a small amount of hydrochloric acid (1.8% by volume of t...

specific Embodiment approach 2

[0035]1. Take 0.2g microcrystalline cellulose and dry it in vacuum at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 10h; add 0.4g lithium chloride after cooling to room temperature; continue stirring for 4h Afterwards, heat up to 70°C again, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 4h, stop the reaction after continuing to stir and reflux for 24h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C To constant weight, the yield was 87%.

[0036] 2. Continue vacuum drying the above intermediate product at 80°C for 4h, then add excess 3,5-dichlorophenylisocyanate after reflux in anhydrous pyridine for 2h, stop the reaction after continuing to reflux at 80°C for 12h, Wash well with methanol and dry under vacuum.

[0037] 3. Dissolve the intermediate product obtained in the previous step in a tetrahydrofuran solution containing a small amount of hydrochloric acid (2% by volume of te...

specific Embodiment approach 3

[0042] 1. Take 0.3g of microcrystalline cellulose and vacuum-dry at 80°C for 4h, then stir and reflux in anhydrous N,N-dimethylacetamide for 14h; add 0.6g of lithium chloride after cooling to room temperature; continue to stir for 5h Afterwards, heat up to 70°C again, add anhydrous pyridine, add excess triphenylchloromethane after reflux for 4h, stop the reaction after continuing to stir and reflux for 24h; cool to room temperature, add methanol to settle, filter and wash, and vacuum dry at 60°C To constant weight, the yield was 89%.

[0043] 2. Continue vacuum drying the above intermediate product at 80°C for 2h, then reflux in anhydrous pyridine for 4h, add excess 4-chlorophenyl isocyanate, continue to reflux at 80°C for 14h, stop the reaction, and fully Wash and vacuum dry.

[0044] 3. The intermediate product obtained in the previous step was dissolved in a tetrahydrofuran solution containing a small amount of hydrochloric acid (1.9% by volume of tetrahydrofuran) for hydr...

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Abstract

The invention provides a cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate and a preparation method of the cellulose derivative. The method comprises the following steps of: carrying out vacuum drying on cellulose, carrying out stirring reflux in anhydrous N,N-dimethyl acetamide, cooling to room temperature, then, adding lithium chloride, reheating, adding anhydrous pyridine, refluxing, then, adding superfluous triphenylchloromethane, and carrying out continuous stirring reflux; after vacuum drying, carrying out refluxing in anhydrous pyridine, then, adding superfluous phenyl isocyanate, stopping reaction, completely washing by using methanol, and carrying out vacuum drying; dissolving into tetrahydrofuran solution containing hydrochloric acid so as to carry out hydrolysis; and fully dissolving into anhydrous pyridine, adding superfluous cyclohexyl isocyanate, stopping reaction, adding methanol, and carrying out vacuum drying, thereby obtaining the cellulose derivative simultaneously containing cyclohexyl carbamate and phenyl carbamate. According to the method, the adopted cellulose is wide in source, is cheap and is easily available, and a synthesis process is simple, mature, easy to control and high in yield. The method can be applied to large-scale batch production.

Description

technical field [0001] The invention relates to a preparation method of cellulose derivatives. Background technique [0002] At present, there are more than ten kinds of commercial polysaccharide chiral stationary phases (including cellulose and amylose), but all commercial chiral stationary phases are based on single-substituted polysaccharides Derivatives, that is, these derivatives have a single substituent at all three positions of the sugar unit. In order to develop new chiral stationary phases with high-efficiency broad-spectrum chiral recognition capabilities and expand the application range of chiral stationary phases, some attempts have been made to selectively substitute polysaccharide polymers. In 1993, the Okamoto research group first applied the regioselective substitution method to synthesize cellulose and starch derivatives with two phenyl carbamate groups at the 2-, 3- and 6-positions of the sugar unit (Bull Chem Soc Jpn, 1993, 66, 2225). Since then, this ...

Claims

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Application Information

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IPC IPC(8): C08B15/06B01J20/29B01J20/30
Inventor 沈军刘双燕赵勇强沈越
Owner HARBIN ENG UNIV
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