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Alkyl salicylic acid synthesis method

A technology for the synthesis of alkyl salicylic acid and its method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylate, etc., which can solve problems such as inability to recycle, high equipment requirements, and reduced utilization rate of raw material olefins, etc. To achieve the effect of environmental protection and low price

Active Publication Date: 2015-05-27
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem in this process is that in the alkylphenol obtained after phenol alkylation, there are two cases where the long-chain alkyl group is located in the ortho-position and in the para-position, usually in a ratio of about 1:1, while the ortho-position alkylphenol The activity is low, and it is difficult to be carboxylated in the Kolbe-Schmitt reaction, so only about 70% of the total amount of alkylphenols is usually converted into alkyl salicylic acid, which will directly lead to a decrease in the utilization rate of raw material olefins, thus making Production costs remain high; alkylphenols cannot be completely converted into alkylsalicylic acids, so about 30% of free alkylphenols exist in the final product, which will make the product too dark, seriously affecting its application and sales
But the defect of this method is: catalyst alkylsulfonic acid is liquid acid mostly, has strong corrosiveness, has higher requirement to equipment, and the catalyst recovered after reaction will be deactivated in addition, can't recycle, because catalyst price is high, thus very difficult Difficult to achieve mass production

Method used

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  • Alkyl salicylic acid synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 112.2 g of 1-hexadecene was added to a 500 ml four-necked round-bottom flask, stirred with a magnetic stirrer, 69.0 g of salicylic acid was slowly added, and then 13.8 g of benzenesulfonic acid was added. Nitrogen gas was introduced, the reaction temperature was 120° C., and the reaction time was 7 hours. After the reaction is finished, water is added to wash to remove the catalyst, and after standing to separate layers to remove water, the product alkyl salicylic acid is obtained. The conversion rate of olefin reaction was 89.6%.

Embodiment 2

[0025] 126.2 g of 1-octadecene was added to a 500 ml four-neck round-bottom flask, stirred with a magnetic stirrer, 69.0 g of salicylic acid was slowly added, and then 13.8 g of benzenesulfonic acid was added. Nitrogen gas was introduced, the reaction temperature was 130° C., and the reaction time was 7 hours. After the reaction is finished, water is added to wash to remove the catalyst, and after standing to separate layers to remove water, the product alkyl salicylic acid is obtained. The conversion rate of olefin reaction was 76.2%.

Embodiment 3

[0027] Add 117.6 g of C16C18 alkenes to a 500 ml four-neck round bottom flask, stir with a magnetic stirrer, slowly add 69.0 g of salicylic acid, and then add 13.8 g of benzenesulfonic acid. Nitrogen gas was introduced, the reaction temperature was 130° C., and the reaction time was 7 hours. After the reaction is finished, water is added to wash to remove the catalyst, and after standing to separate layers to remove water, the product alkyl salicylic acid is obtained. The conversion rate of olefin reaction was 83.7%.

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Abstract

The present invention discloses an alkyl salicylic acid synthesis method, which comprises: mixing olefin with a carbon number of 4-50 and salicylic acid, and carrying out an alkylation reaction under a catalysis effect of aryl sulfonic acid at a temperature of 50-160 DEG C. According to the present invention, aryl sulfonic acid is adopted as a catalyst, a conversion rate can achieve 60-95%, the catalyst does not cause corrosion on the equipment, price is relatively low, the catalyst can be recycled, no three-waste emission problem exists, and environmental protection is easily achieved.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing alkyl salicylic acid. (2) Background technology [0002] The conventional preparation method of alkyl salicylic acid is as follows: phenol and olefins are used as raw materials to prepare alkyl phenol by alkylation reaction, and then the alkyl phenol is carboxylated by Kolbe-Schmitt reaction to provide alkyl salicylic acid. Both patents EP370555 and UK586461 report the preparation of alkyl salicylic acid through the Kolbe-Schmitt process. The problem in this process is that in the alkylphenol obtained after phenol alkylation, there are two cases where the long-chain alkyl group is located in the ortho-position and in the para-position, usually in a ratio of about 1:1, while the ortho-position alkylphenol The activity is low, and it is difficult to be carboxylated in the Kolbe-Schmitt reaction, so only about 70% of the total amount of alkylphenols is usually converted into alkyl salicylic acid, whi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/05C07C51/353
CPCY02P20/584
Inventor 梁依经管飞伏喜胜
Owner PETROCHINA CO LTD
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