Method for transforming cisconfiguration of oxane compounds to transconfiguration
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A technology of cis-configuration and trans-configuration, applied in organic chemistry and other fields, can solve the problems of low yield of trans-oxane compounds and environmental pollution, so as to improve the utilization rate of raw materials, reduce environmental pollution, and improve utilization rate effect
Active Publication Date: 2012-08-15
WEINAN HIGH NEW DISTRICT HAIQIN NEW ELECTRONICS MATERIAL
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Therefore, in order to obtain the oxane compound of high-purity target trans configuration, its cis isomer needs to be removed, so that the yield of preparing trans oxane compound is relatively low (about 50%), like this A large amount of cis-trans mixed waste mother liquor is produced, and the extracted mother liquor is discarded, causing environmental pollution
However, there is no literature report on how to recycle and reuse such problems
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Embodiment 1
[0017] Embodiment 1 (preparation of trans 5-n-pentyl-2-(4-cyanophenyl)-1,3-dioxane (I a))
[0018] Add cis-5-n-pentyl-2-(4-cyanophenyl)-1,3-dioxane 20g successively in a 250mL three-necked reaction flask equipped with mechanical stirring, reflux condenser, and addition funnel, and the catalyst is Toluenesulfonic acid 2g, toluene 100mL, start stirring and heating, reflux reaction at 105-110°C for 3-8h, sample analysis, confirm the reaction is terminated according to the gas phase analysis results, cool, then add water 50mL to the reaction liquid, separate liquid, water phase Extract with 20 mL of toluene, combine the organic phases, wash with water until neutral, dry with 5 g of anhydrous magnesium sulfate for 8 h, filter, then rinse the filter cake twice with 10 mL of toluene, and take a sample analysis to determine the crude product quality ω (Ia): 76%, After distilling off the solvent, it was purified to obtain 13.9 g of product (Ia), ω(Ia): 99.5%, yield: 69.5%. Product mas...
Embodiment 2
[0019] Example 2 (preparation of trans 5-p-ethylphenyl-2-(4-cyanophenyl)-1,3-dioxane (I b))
[0020] Add cis-5-p-ethylphenyl-2-(4-cyanophenyl)-1,3-dioxane 20g successively in a 250mL three-necked reaction flask equipped with mechanical stirring, reflux condenser, and addition funnel, Catalyst p-toluenesulfonic acid 0.2g, toluene 100mL, start stirring and heating, reflux at 105-110°C for 3-8h, other conditions are the same as in Example 1, and purify to obtain 14.3g of product (I b), ω(I b): 99.5 %, yield: 71.5%. Product mass spectrometry result: ES-MSm / z: 293[M]+.
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Abstract
The invention relates to a synthetic method of important functional materials liquid crystal monomer oxane compounds, and particularly relates to a method for transforming cisconfiguration of oxane compounds to transconfiguration. The method comprises the following steps: reacting for 2-12 hours at the temperature of 35-200 DEG C by taking cis-oxane compounds as raw materials, para-toluenesulfonic acid as a catalyst and an organic solvent as a reaction medium, thereby transforming the cis-oxane compounds to obtain corresponding trans-oxane compounds; and purifying. After purifying, omega of the trans-oxane compounds is more than 99%, the total yield of reaction is more than 69%, the purpose of recovering useful products is realized, the emission of wastes during the production of oxane transconfiguration products is reduced, and the utilization rate of raw materials during the production of similar transconfiguration oxane compounds is improved. The method is simple to operate, the reaction conditions are easy to control, and the industrial production is easy to realize.
Description
technical field [0001] The invention relates to a synthesis method of a class of important functional material liquid crystal monomer oxane compounds, in particular a method for transforming the cis configuration of the oxane compounds into a trans configuration. technical background [0002] Liquid crystal display technology has been widely used in daily life. The synthesis of liquid crystal monomer, its core material, has always been the focus of chemists. The cost directly affects the cost of liquid crystal displays. It is an important class of liquid crystal monomer, which is widely used in TN, STN, TFT and other types of liquid crystal displays. Its traditional synthesis method is to carry out condensation reaction of 2-substituted propylene glycol and 4-substituted benzaldehyde compounds to synthesize Oxane monomer liquid crystals, but this synthesis is accompanied by the formation of cis-trans isomers, but only pure trans-structure can be used for liquid crystal displ...
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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06
Inventor 董兆恒王小伟王建文刘骞峰高仁孝赵振奇袁江波杨燕冯凯
Owner WEINAN HIGH NEW DISTRICT HAIQIN NEW ELECTRONICS MATERIAL
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