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Synthetic method of cellulose derivatives having long alkoxyl side chain

A technology of cellulose and synthesis method, applied in the field of synthesis of cellulose derivatives, can solve the problems of changing secondary structure, weakening chiral recognition ability, chiral recognition ability and other performance influences

Active Publication Date: 2015-12-09
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The introduction of substituents with different structures and properties on the benzene ring has a great influence on the chiral recognition performance of cellulose phenyl carbamate derivatives, and the introduction of strong polar groups often weakens their chiral recognition ability
However, until now, there have been no reports on the mechanism of the effect of this polar group on the chiral recognition ability.
In addition, the chain length of the introduced substituents may change the secondary structure of such derivatives, thereby affecting their chiral recognition ability and other properties (liquid crystallinity)

Method used

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  • Synthetic method of cellulose derivatives having long alkoxyl side chain
  • Synthetic method of cellulose derivatives having long alkoxyl side chain
  • Synthetic method of cellulose derivatives having long alkoxyl side chain

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0030] 1. Dissolve 2.0 g of triphosgene in high-purity N 2Fully dissolved with an appropriate amount of ethyl acetate under protection. Transfer the pre-prepared p-octyloxyaniline solution (60% concentration) to a constant pressure low liquid funnel and wait for dropwise addition. The entire reaction system was transferred to an ice-water bath, and the low temperature environment (0-5° C.) was controlled. Complete the configuration of the triphosgene solution and the p-octyloxyaniline solution, and put them into the reaction bottle.

[0031] 2. After the reaction bottle is stabilized in the ice-water bath, start adding the aniline solution dropwise (control the dropping rate at 1 drop / 1-2s, so as not to cause the aniline concentration to be too high and aggravate the occurrence of side reactions). Stir for 20mins, transfer to a 60°C oil bath to continue the reaction. Finally, after the reaction is completed, cool down to room temperature and use high-purity N 2 Replace the...

specific Embodiment approach 2

[0034] 1. Dissolve 2.0 g of triphosgene in high-purity N 2 Fully dissolved with an appropriate amount of ethyl acetate under protection. Transfer the pre-prepared p-dodecyloxyaniline solution (60% concentration) to a constant pressure low liquid funnel and wait for dropwise addition. The entire reaction system was transferred to an ice-water bath, and the low temperature environment (0-5° C.) was controlled. Complete the configuration of the triphosgene solution and the p-dodecyloxyaniline solution, and put them into the reaction bottle.

[0035] 2. After the reaction bottle is stabilized in the ice-water bath, start adding the aniline solution dropwise (control the dropping rate at 2 drops / 1-2s, so as not to aggravate the occurrence of side reactions caused by excessive aniline concentration), after the addition is completed, continue to Stir for 30mins, transfer to a 60°C oil bath to continue the reaction. Finally, after the reaction is completed, cool down to room temper...

specific Embodiment approach 3

[0038] 1. Dissolve 2.0 g of triphosgene in high-purity N 2 Fully dissolved with an appropriate amount of ethyl acetate under protection. Transfer the pre-prepared p-hexadecyloxyaniline solution (60% concentration) to a constant pressure low liquid funnel and wait for dropwise addition. The entire reaction system was transferred to an ice-water bath, and the low temperature environment (0-5° C.) was controlled. Complete the configuration of the triphosgene solution and the hexadecyloxyaniline solution, and put them into the reaction bottle.

[0039] 2. After the reaction bottle is stabilized in the ice-water bath, start adding the aniline solution dropwise (control the dropping rate at 4 drops / 1-2s, so as not to aggravate the occurrence of side reactions caused by the high concentration of aniline). Stir for 25mins, transfer to a 60°C oil bath to continue the reaction. Finally, after the reaction is completed, cool down to room temperature and use high-purity N 2 Replace th...

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Abstract

The invention provides a synthetic method of cellulose derivatives having a long alkoxyl side chain. The method includes the steps of (1) with a triphosgene method, synthesizing phenyl isocynate having the long alkoxyl side chain on the basis of phenylamine and triphosgene; and (2) with microcrystal cellulose as a substrate, introducing the long alkoxyl side chain into a main chain of cellulose through esterification to synthesize the cellulose phenyl carbamate derivatives having a long alkoxyl side chain. The synthetic method is clear and available in route, is mature in technology, is simple in operation, is less in conditions required to control, is easy to achieve and can be used in large-scale batched production.

Description

technical field [0001] The invention relates to a method for synthesizing cellulose derivatives, in particular to a method for synthesizing cellulose derivatives with long alkoxy side chains. Background technique [0002] In recent decades, polysaccharide derivatives have shown good chiral recognition performance as chiral stationary phases for high performance liquid chromatography, especially cellulose phenyl carbamate derivatives have been favored due to their excellent performance. The introduction of substituents with different structures and properties on the benzene ring has a great influence on the chiral recognition performance of cellulose phenyl carbamate derivatives, and the introduction of strong polar groups often weakens their chiral recognition ability. But until now, no systematic research has been reported on the mechanism of the effect of this polar group on the chiral recognition ability. In addition, the chain segment length of the introduced substituen...

Claims

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Application Information

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IPC IPC(8): C08B15/06
Inventor 沈军赵勇强李庚田溪鹤
Owner HARBIN ENG UNIV
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