Preparation method of 5-chloromethyl salicylaldehyde

A technology of chloromethyl salicylaldehyde and salicylaldehyde, which is applied in the field of preparation of 5-chloromethyl salicylaldehyde, can solve the problems of difficult drying, low yield of 5-chloromethyl salicylaldehyde, and difficult Washing and other issues, to achieve the effect of improving the conversion rate of raw materials, increasing the probability of participating in chloromethylation reactions, and reducing production costs

Inactive Publication Date: 2011-09-14
HUAIHAI INST OF TECH
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Problems solved by technology

The main reason is that the 5-chloromethyl salicylaldehyde produced by the chloromethylation reaction of salicylaldehyde is a solid powder insoluble in hydrochloric acid solution, which is fused and bonded with the salicylaldehyde liquid beads dispersed in concentrated hydrochloric acid. and along with the continuous increase of 5-chloromethyl salicylaldehyde product amount, 5-chloromethyl salicylaldehyde gradually bonds into spherical bodies with different diameters with raw material salicylaldehyde, causing salicylaldehyde to not all participate in chlorine Methylation reaction, so the preparation yield of 5-chloromethyl salicylaldehyde in the existing reports is not high, and at the same time, because 5-chloromethyl salicylaldehyde is interspersed, the resulting 5-chloromethyl salicylaldehyde is still viscous , not easy to wash, not easy to dry

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  • Preparation method of 5-chloromethyl salicylaldehyde
  • Preparation method of 5-chloromethyl salicylaldehyde
  • Preparation method of 5-chloromethyl salicylaldehyde

Examples

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Embodiment 1

[0021] In a 500mL reaction flask, put 50g of salicylaldehyde, 55g of formaldehyde solution with a concentration of 37% by mass and 2.5g of triethylbenzyl ammonium chloride, turn on the mixer, control the temperature at 5-15°C, and then add Concentration is 37~38% hydrochloric acid 200mL, after stirring reaction for 12 hours, feed 37g of hydrogen chloride gas into reaction system continuously within 10 hours. Thereafter, the airtight reaction was continued for 24 hours until the end. The crude product of 5-chloromethyl salicylaldehyde was obtained by discharging and filtering, and was put into a washing flask, and 150 g of water was added, and the temperature of the material in the washing flask was controlled at 40-45° C., and stirred and washed for 1 hour. Afterwards, repeat washing with water once; then wash once with aqueous sodium bicarbonate solution with a mass percentage concentration of 8-10% at room temperature, and finally wash once more with water, and vacuum-dry th...

Embodiment 2

[0023] According to the operating method and steps of Example 1, 55 g of formaldehyde solution with a mass percent concentration of 37% was replaced with 23 g of paraformaldehyde, and the reaction time was extended to 96 hours to obtain 67.1 g of 5-chloromethyl salicylaldehyde product, The melting point is 82-85°C, and the yield is 96%.

Embodiment 3

[0025] According to the operation method and steps of Example 1, 55 g of formaldehyde solution and 1 g of triethylbenzyl ammonium chloride with a mass percent concentration of 37% were replaced with 23 g of paraformaldehyde and 3.8 g of tri-n-butyl benzyl ammonium chloride 67.2 g of 5-chloromethyl salicylaldehyde was obtained, with a melting point of 82-86° C. and a yield of 96.1%.

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Abstract

The invention relates to a preparation method of 5-chloromethyl salicylaldehyde. The preparation method is realized in a way that: salicylaldehyde, formaldehyde and concentrated hydrochloric acid are used as raw material, quaternary ammonium salt is used as a catalyst, and the 5-chloromethyl salicylaldehyde is prepared by chloromethylation reaction of salicylaldehyde. The quaternary ammonium salt can effectively prevent the 5-chloromethyl salicylaldehyde product and salicylaldehyde from adhesion and agglomeration, thereby greatly increasing the utilization ratio of the raw material salicylaldehyde and the yield of the 5-chloromethyl salicylaldehyde product; and the filtered 5-chloromethyl salicylaldehyde product powder is dry, and is easy for washing and drying, so that the preparation process of the 5-chloromethyl salicylaldehyde is easy to operate.

Description

technical field [0001] The invention relates to a preparation method of 5-chloromethyl salicylaldehyde. technical background [0002] In recent years, small molecular Salen complexes and their high molecular Salen complexes, which are used as oxidation catalysts or olefin polymerization catalysts, have attracted attention from many aspects. Among them, 5-chloromethyl salicylaldehyde (5-chloromethylsalicylaldehyde, CMSA) is one of the main raw materials for the synthesis of water-soluble, oil-soluble and chiral Salen-type complexes. The existing reported synthesis methods of 5-chloromethyl salicylaldehyde are all to react salicylaldehyde, aqueous formaldehyde or paraformaldehyde in concentrated hydrochloric acid at low temperature for a long time to obtain the product. The present inventor finds in research no matter adopt formaldehyde aqueous solution or paraformaldehyde as raw material, whether pass into hydrogen chloride gas in the reaction system, the product of gained 5...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/565C07C45/63B01J31/02
Inventor 张田林王佳佳倪镜涛
Owner HUAIHAI INST OF TECH
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