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A kind of method for synthesizing o-sulfonic acid benzaldehyde under normal pressure

A technology of o-sulfonic acid benzaldehyde and a synthesis method, applied in the directions of sulfonic acid preparation, sulfonate preparation, organic chemistry, etc., can solve problems such as restricting the industrial production of sodium o-sulfonic acid benzaldehyde, and achieve easy control of industrial production and high yield. The effect of high rate and few by-products

Active Publication Date: 2022-07-15
WUHAN DONGHU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These factors have restricted the industrialized production of o-sodium sulfonate benzaldehyde

Method used

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  • A kind of method for synthesizing o-sulfonic acid benzaldehyde under normal pressure
  • A kind of method for synthesizing o-sulfonic acid benzaldehyde under normal pressure
  • A kind of method for synthesizing o-sulfonic acid benzaldehyde under normal pressure

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 7g of o-chlorobenzaldehyde (0.05mol) was added to the three-necked flask, 15mL of water and 0.3g of tetrabutylammonium bromide were added successively, the temperature was raised to 60° C., and stirred for 10min. Another 11.67 g of potassium bisulfite (0.0525 mol) was dissolved in 20 mL of water, and the potassium bisulfite solution was added dropwise to the reaction mixture for about 30 minutes. The reaction was carried out at about 70°C for 8h, and the reaction was completed to obtain a pale yellow liquid. The reaction solution was transferred to a beaker, a small amount of dilute hydrochloric acid was added, and the pH was adjusted to 1.0. Let stand, cool, and crystallize. Suction filtration and drying to obtain crude product. Then recrystallize with absolute ethanol to obtain 7.32 g of the finished product of o-sulfonic acid benzaldehyde, needle-like crystals, the measured melting point is 114.0 ° C ~ 115.7 ° C (the literature value is 114.1 ° C ~ 115.4 ° C), the ...

Embodiment 2

[0028] 7g of o-chlorobenzaldehyde (0.05mol) was added to the three-necked flask, 17.5mL of water and 0.5g of tert-butylamine sulfate were added successively, the temperature was raised to 60° C., and stirred for 10min. Another 11.78 g of potassium bisulfite (0.053 mol) was dissolved in 20 mL of water, and the potassium bisulfite solution was added dropwise to the reaction mixture for about 30 minutes. The reaction was carried out at about 70°C for 10h, and the reaction was completed to obtain a pale yellow liquid. The reaction solution was transferred to a beaker, a small amount of dilute hydrochloric acid was added, and the pH was adjusted to 1.0. Let stand, cool, and crystallize. Suction filtration and drying to obtain crude product. Then recrystallize with absolute ethanol to obtain 7.98 g of o-sulfonic acid benzaldehyde finished product, needle-like crystals, the measured melting point is 114.1 ° C ~ 115.0 ° C (the literature value is 114.1 ° C ~ 115.4 ° C), the purity i...

Embodiment 3

[0030] 7g of o-chlorobenzaldehyde (0.05mol) was added to the three-necked flask, 20mL of water and 0.5g of tert-butylamine hydrochloride were added successively, the temperature was raised to 60° C., and stirred for 10min. Another 12.00 g of potassium bisulfite (0.054 mol) was dissolved in 20 mL of water, and the potassium bisulfite solution was added dropwise to the reaction mixture for about 30 minutes. The reaction was carried out at about 70°C for 12h, and the reaction was completed to obtain a pale yellow liquid. The reaction solution was transferred to a beaker, a small amount of dilute hydrochloric acid was added, and the pH was adjusted to 1.0. Let stand, cool, and crystallize. Suction filtration and drying to obtain crude product. Then recrystallize with absolute ethanol to obtain 7.11 g of finished product of o-sulfonic acid benzaldehyde, needle-like crystals, the measured melting point is 113.8 ° C ~ 115.1 ° C (the literature value is 114.1 ° C ~ 115.4 ° C), the p...

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Abstract

The invention relates to a method for synthesizing o-sulfonic acid benzaldehyde under normal pressure. The method comprises the following steps: taking o-chlorobenzaldehyde as a raw material, and using a partial weight sulfite as a sulfonating agent; under the catalysis of tert-butylamine salt or quaternary ammonium salt, benzaldehyde-2-sulfonate is generated through a sulfonation reaction, and then acidified , the preparation of o-sulfonic acid benzaldehyde. The preparation method has mild conditions, can prepare the o-sulfonic acid benzaldehyde under normal pressure and low temperature, has few side reactions, high yield, simple post-processing, high safety, low cost, simple operation and easy control of industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing o-sulfonic acid benzaldehyde under normal pressure. Background technique [0002] Orthosulfonic acid benzaldehyde, also known as benzaldehyde-2-sulfonic acid, the molecular formula is C 7 H 6 O 4 S, is an important dye and pharmaceutical intermediate. Its sodium salt, namely sodium o-sulfonate benzaldehyde, also known as sodium o-formylbenzenesulfonate, is an important chemical raw material. It is mainly used as an intermediate for the synthesis of fluorescent whitening agents CBS and triphenylmethane dyes, as an intermediate for the preparation of antifungal, anticancer, anti-HIV and moth repellent N and other drugs, and can also be used for the preparation of ultraviolet absorbers in cosmetics. It plays an integral role in industries such as dyes, medical and cosmetics. [0003] In traditional industry, sodium o-sulfonate benzaldehyde us...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/32C07C303/22C07C309/44
CPCC07C303/32C07C303/22C07C309/44
Inventor 杨洁刘波刘晓霞程时劲吴喆石一郎
Owner WUHAN DONGHU UNIV
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