Preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate

A technology of dimethylaminostyrene and p-toluene sulfonate, which is applied in sulfonate preparation, organic chemistry and other directions, can solve the problems of limiting the preparation of high-quality nonlinear crystal materials, complicated purification process and high preparation cost, and achieves a reduction in The effect of experimental cost, high product purity and low preparation cost

Inactive Publication Date: 2013-03-13
QINGDAO UNIV
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Problems solved by technology

4-(4-Dimethylaminostyryl)picoline p-toluenesulfonate crystal is an organic salt crystal formed by strong Coulomb force. Its cation contains a benzene ring and a pyridine ring. It is a conjugated Hyperconjugated ions with large π bonds belong to monoclinic crystals, the point group is m, the space group is Cc, and its unit cell parameters are: α=90°, β=92.24°, γ=90°, Z=4; the preparation process of the existing high-purity 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate has relatively Multiple by-products are generated, the purification process is complicated, the preparation cost is high, and the yield is low, which limits the preparation of high-quality nonlinear crystal materials. Therefore, it is sought to design a 4-(4) with low cost, mild reaction conditions, high yield and simple purification. The preparation method of -dimethylaminostyryl) picoline p-toluenesulfonate has good practical significance and economic value

Method used

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  • Preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate

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Embodiment

[0018] The specific steps for preparing 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate in this example include five steps: synthesis reaction, condensation reaction, preparation of silver p-toluenesulfonate, exchange reaction and filtration purification:

[0019] (1) Synthesis reaction: Dissolve 0.03mol 4-picoline and 0.032mol iodomethane in 4ml and 4ml of absolute ethanol with a purity of 99.7%, respectively, and then mix and stir the two for 20 minutes to form a white needle-like solid. Utilize 99.7% ethanol to wash and filter, obtain 0.023mol 4-picoline iodide salt, yield rate is 76.7%;

[0020] (2) Condensation reaction: Dissolve 0.02mol of 4-picoline iodide and 0.02mol of p-dimethylaminobenzaldehyde in 20ml and 50ml of methanol with a purity of 99.5%, respectively, and then place the two solutions in 250ml of three In a well-boiled flask, heat and stir to 70°C, condense and reflux at the same time, add three drops of piperidine as a catalyst, the solution gradually ...

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Abstract

The invention belongs to the technical field of functional material preparation, and relates to a preparation method of 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate, which comprises the steps of synthetic reaction, condensation reaction, silver p-toluenesulfonate, exchange reaction and purification by filtration. The method specifically comprises the following steps: dissolving 4-methylpyridine and iodomethane in ethanol to carry out reaction, thereby generating 4-methylpyridinium iodide; dissolving 4-methylpyridinium iodide and p-dimethylaminobenzaldehyde in methanol, and adding a catalyst to react, thereby generating 4-(4-dimethylaminostyryl)methylpyridyl iodide; reacting p-toluenesulfonic acid and silver oxide to generate silver p-toluenesulfonate; reacting the silver p-toluenesulfonate and 4-(4-dimethylaminostyryl)methylpyridyl iodide to generate silver iodide and 4-(4-dimethylaminostyryl)methylpyridyl p-toluenesulfonate; and purifying by filtration. The invention has the advantages of simple preparation technique, reliable principle, low preparation cost, high product purity, mild reaction conditions, high yield and environment friendliness.

Description

Technical field: [0001] The invention belongs to the technical field of preparation of functional materials, and relates to a preparation method of nonlinear optical material 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate, which is used for the preparation of high-quality nonlinear crystal materials , to realize the synthesis and purification of high-purity 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate. Background technique: [0002] At present, the commonly used 4-(4-dimethylaminostyryl)picoline p-toluenesulfonate is an ionic crystal material with a high nonlinear coefficient and can be used as a nonlinear optical material with good performance. It can also be used as a terahertz wave THz source in THz radiation, and THz waves are generated by optical rectification; terahertz waves are commonly referred to as THz waves, which refer to electromagnetic waves with a wavelength of 0.1-10THz and a wavelength of 30um-3mm, which belong to the far-infrared band; 4-( 4...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07C309/30C07C303/32
Inventor 滕冰曹丽凤钟德高庄树杰冯珂史永新
Owner QINGDAO UNIV
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