Alkylation method for salicylic acid

A salicylic acid and alkylation technology, applied in chemical instruments and methods, organic chemistry, carboxylate preparation, etc., can solve problems such as excessive by-product content, achieve low by-product content, reduce self-polymerization, and light color Effect

Active Publication Date: 2016-07-20
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The purpose of the present invention is to provide a kind of alkylation method of salicylic acid, aim to solve the problem that by-produ

Method used

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  • Alkylation method for salicylic acid

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Experimental program
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Effect test

Embodiment 1

[0030]Add 201.6g of 1-octadecene, 125.0g of salicylic acid, 0.03g of hydroquinone, and 21.2g of benzenesulfonic acid in a 500ml glass container equipped with a stirrer, thermometer, heating mantle and nitrogen pipeline . Introduce nitrogen, stir with a magnetic stirrer, react at 125°C for 8h, then raise the temperature to 150°C, and add 80.0g of styrene within 1h, and keep it for 1.0h after the addition. After the reaction is over, let it settle to recover the catalyst benzenesulfonic acid to obtain the product alkyl salicylic acid.

Embodiment 2

[0032] 112.2 g of 1-decene, 123.0 g of salicylic acid, 0.03 g of hydroquinone, and 18.5 g of benzenesulfonic acid were added to a 500 ml glass vessel equipped with a stirrer, a thermometer, a heating mantle, and a nitrogen pipeline. Introduce nitrogen, stir with a magnetic stirrer, react at 90°C for 2h, then raise the temperature to 152°C, and add 70.0g of styrene within 1h, and keep it for 1.0h after the addition. After the reaction is over, let it stand and settle to recover the catalyst benzenesulfonic acid to obtain the product alkyl salicylic acid. The purity of the product analyzed by liquid chromatography was 94.14%.

Embodiment 3

[0034] In a 500ml glass container equipped with a stirrer, thermometer, heating mantle and nitrogen pipeline, add 1-tetracocene 134.4g, then add salicylic acid 64.0g, add hydroquinone 0.02g, then add 12.3g benzenesulfonate acid. Introduce nitrogen, stir with a magnetic stirrer, react at 135°C for 12h, then raise the temperature to 155°C, and add 56.0g of styrene within 1h, and keep it for 1.0h after the addition. After the reaction is over, let it stand and settle to recover the catalyst benzenesulfonic acid to obtain the product alkyl salicylic acid. The purity of the product analyzed by liquid chromatography was 91.39%.

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Abstract

The invention discloses an alkylation method for salicylic acid. The method comprises the following steps: with long-chain olefin and excess salicylic acid as raw materials, adding a certain amount of a polymerization inhibitor into the raw materials and carrying out an alkylation reaction under the catalysis of aryl sulfonic acid so as to prepare long-chain alkyl salicylic acid; and after completion of the alkylation reaction, adding active alkene and carrying out a secondary alkylation reaction to allow salicylic acid which has not participated in the primary alkylation reaction to be completely converted into the target product, i.e., alkyl salicylic acid. The method provided by the invention can effectively reduce the contents of by-products like free salicylic acid, bialkyl products and olefin oligomer in products obtained in the prior art, increases the purity of the target product, and is simple to operate and beneficial for industrial production.

Description

technical field [0001] The invention relates to a method for alkylating salicylic acid. Background technique [0002] Long-chain alkyl salicylic acid is usually used to prepare a lubricating oil detergent with excellent performance - calcium alkyl salicylate. [0003] The traditional preparation method of long-chain alkyl salicylic acid is to use phenol and long-chain α-olefins as starting materials, and prepare through the Kolbe-Schmitt process, which has long reaction steps and low conversion rate, and about 30% of the final product The presence of free alkylphenols seriously affects product quality. Currently, a method for preparing alkyl salicylic acid by alkylation reaction using salicylic acid and olefins as starting materials has been reported. This preparation method not only greatly shortens the traditional preparation process, thereby shortening the production cycle and reducing the production cost, but also the prepared product hardly contains by-product alkylph...

Claims

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Application Information

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IPC IPC(8): C07C65/05C07C51/353
Inventor 梁依经伏喜胜杨鹏管飞
Owner PETROCHINA CO LTD
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