Synthetic method for cellulose derivative with large volume liquid crystal unit side group

A technology of liquid crystal unit and cellulose, which is applied in the field of synthesis of cellulose derivatives with side groups of large-volume liquid crystal units, can solve the problems of small substituents, and achieve the effects of easy control, mature synthesis process and high yield

Active Publication Date: 2015-12-16
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional cellulose derivatives generally introduce small substituents, and there are relatively few studies on cellulose derivatives that introduce large-volume function

Method used

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  • Synthetic method for cellulose derivative with large volume liquid crystal unit side group
  • Synthetic method for cellulose derivative with large volume liquid crystal unit side group
  • Synthetic method for cellulose derivative with large volume liquid crystal unit side group

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment approach 1

[0029] 1. Take 15mmol 2,5-dibromoaniline, 36mmol p-methoxyphenylboronic acid, 0.09mmol sodium carbonate and 0.6mmol tetrakistriphenylphosphine palladium and vacuum dry for 0.5h, then mix in 75ml dioxane and 37.5ml water Stir and reflux at 80°C for 30 hours to stop the reaction; cool to room temperature, remove the solvent by rotary evaporation, add n-hexane to filter and wash; purify the crude product by column chromatography to obtain pure 2,5-bis(4'-methoxy phenyl) aniline with a yield of 80%.

[0030] 2. Take 1.6mmol of the above-mentioned intermediate product and put it into reaction bottle 1, add 14.0ml of water and 0.26ml of 98% concentrated sulfuric acid mixture, stir and reflux at 60°C for 1.5h; then add 1ml of 1.76mol / L sodium nitrite at 0°C Solution, stirred and refluxed for 1h; vacuum-dried 2.40mmol cuprous bromide in reaction flask 2 for 0.5h, stirred and refluxed in 4ml of water and 4mL40wt% hydrobromic acid mixture for 2h; reacted in reaction flask 1 at 50°C The...

specific Embodiment approach 2

[0035] 1. Take 15mmol 2,5-dibromoaniline, 36mmol p-ethoxyphenylboronic acid, 0.09mmol sodium carbonate and 0.6mmol tetrakistriphenylphosphine palladium and vacuum-dry for 0.5h, then mix in 75ml dioxane and 37.5ml water Stir and reflux at 80°C for 30 hours to stop the reaction; cool to room temperature, remove the solvent by rotary evaporation, add n-hexane to filter and wash; purify the crude product by column chromatography to obtain pure 2,5-bis(4'-ethoxy phenyl) aniline with a yield of 80%.

[0036] 2. Take 1.6mmol of the above-mentioned intermediate product and put it into reaction bottle 1, add 14.0ml of water and 0.26ml of 98% concentrated sulfuric acid mixture, stir and reflux at 60°C for 1.5h; then add 1ml of 1.76mol / L sodium nitrite at 0°C Solution, stirred and refluxed for 1h; vacuum-dried 2.40mmol cuprous bromide in reaction flask 2 for 0.5h, stirred and refluxed in 4ml of water and 4mL40wt% hydrobromic acid mixture for 2h; reacted in reaction flask 1 at 50°C The m...

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Abstract

The invention provides a synthetic method for cellulose derivative with a large volume liquid crystal unit side group. The synthetic method comprises: by taking 2,5-dibromoaniline and 4-alkoxyl phenylboronic acid as raw materials, synthesizing 2,5-bi(4'-alkoxyl phenyl) phenylboronic acid through Suzuki coupling reaction, Sandmeyer reaction, Grignard and the like; then by taking microcrystal cellulose as a reaction medium, synthesizing cellulose-tri(4-bromophenyl amino formate); and carrying out Suzuki coupling reaction on the synthesized 2,5-bi(4'-alkoxyl phenyl) phenylboronic acid and cellulose-tri(4-bromophenyl amino formate) to finally synthesize the novel cellulose phenyl amino formate derivative with large volume liquid crystal unit side group, wherein a benzene ring replaces p-terphenyl in a p-position. The molecular structure of a product is represented in detail and analyzed by applying Fourier transform infrared spectrometer, a nuclear magnetic resonance hydrogen spectrum and a nuclear magnetic resonance carbon spectrum, and the liquid crystal performance of the synthesized novel cellulose derivative is further inspected by applying a differential scanning calorimeter and a polarizing microscope.

Description

technical field [0001] The invention relates to a method for synthesizing cellulose derivatives, in particular to a method for synthesizing cellulose derivatives with large-volume liquid crystal unit side groups. Background technique [0002] Cellulose phenyl carbamate derivatives have excellent chiral recognition ability and are one of the best materials for preparing chiral stationary phases for high performance liquid chromatography. Up to now, there have been relatively systematic researches on such derivatives. The previous results show that the structure, properties and positions of the substituents introduced on the benzene ring have a significant impact on the chiral recognition performance of such derivatives, and the chiral recognition ability of para-substituted derivatives is significantly better than that of ortho or meta-substituted derivatives. However, traditional cellulose derivatives generally introduce small substituents, and there are relatively few stu...

Claims

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Application Information

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IPC IPC(8): C08B15/06C08B3/14
Inventor 沈军迟克一李磊田溪鹤
Owner HARBIN ENG UNIV
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