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Alkyl 2-hydroxy-3-naphthoic acid and its preparation method

A technology of naphthoic acid and alkylsulfonic acid, which is applied in the preparation of carboxylate salts, chemical instruments and methods, and the preparation of organic compounds. It can solve the problems of harsh reaction conditions, high equipment requirements, and inability to recycle, and meet the reaction conditions. Mild, fewer reaction steps, less by-products

Active Publication Date: 2020-02-14
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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
[0016] At present, there are many reports on the alkylation methods of aromatic hydrocarbons and aromatic hydrocarbon derivatives at home and abroad, but most of them use liquid strong acid catalysts, which are highly corrosive, require high equipment, and have harsh reaction conditions, which are not conducive to industrial production; When the catalyst is relatively mild, the reaction conversion rate is often low, and it is not suitable for industrial production
In the prior art, there is no relevant literature report on the preparation method of alkyl 2-hydroxyl-3-naphthoic acid

Method used

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  • Alkyl 2-hydroxy-3-naphthoic acid and its preparation method
  • Alkyl 2-hydroxy-3-naphthoic acid and its preparation method
  • Alkyl 2-hydroxy-3-naphthoic acid and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Add 1-hexene 84.2g (1mol) in a 500mL glass container equipped with a stirrer, thermometer, heating mantle and nitrogen pipeline, then add 2-hydroxy-3-naphthoic acid 94.1g (0.5mol), then add 10.2g Benzenesulfonic acid (0.065 mol, 13% of the moles of 2-hydroxy-3-naphthoic acid). Nitrogen gas was introduced, and a magnetic stirrer was used for stirring. The reaction temperature was 80° C., and the reaction time was 2 h. After reaction finishes, settling down to reclaim catalyst benzenesulfonic acid, carry out distillation and remove unreacted 1-hexene then, obtain product hexyl 2-hydroxyl-3-naphthoic acid, acid value 150.5mgKOH / g (being theoretical value 73.1%).

Embodiment 2

[0062] Add 84.2g (0.5mol) of 1-dodecene into a 500mL glass container equipped with a stirrer, thermometer, heating mantle and nitrogen pipeline, then add 94.1g (0.5mol) of 2-hydroxy-3-naphthoic acid, and then add 0.96 g methanesulfonic acid (0.01 mol, 2% of the moles of 2-hydroxy-3-naphthoic acid). Nitrogen gas was introduced, and a magnetic stirrer was used for stirring. The reaction temperature was 120° C., and the reaction time was 8 h. After reaction finishes, leave standstill to reclaim catalyzer, then filter and remove unreacted 2-hydroxyl-3-naphthoic acid, obtain product dodecyl 2-hydroxyl-3-naphthoic acid, acid number 51.03mgKOH / g ( 32.5% of the theoretical value).

Embodiment 3

[0064] Add 99.2g (0.5mol) of 1-tetradecene into a 500mL glass container equipped with a stirrer, thermometer, heating mantle and nitrogen pipeline, then add 94.1g (0.5mol) of 2-hydroxy-3-naphthoic acid, and then add 7.9g benzenesulfonic acid (0.05mol, 10% of the moles of 2-hydroxy-3-naphthoic acid), then add 4.8g methanesulfonic acid (0.05mol, 10% of the moles of 2-hydroxy-3-naphthoic acid) . Nitrogen gas was introduced, and a magnetic stirrer was used for stirring. The reaction temperature was 120° C., and the reaction time was 8 h. After reaction finishes, leave standstill to reclaim catalyzer, then filter and remove unreacted 2-hydroxyl-3-naphthoic acid, obtain product tetradecyl 2-hydroxyl-3-naphthoic acid, acid value 142.3mgKOH / g ( 98.1% of the theoretical value).

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Abstract

The invention discloses an alkyl 2-hydroxy-3-naphthoic acid and a preparation method thereof. According to the method, 2-hydroxy-3-naphthoic acid and alpha-olefin used as raw materials are subjected to alkylation reaction at certain temperature by using aryl sulfonic acid and the like as catalysts to prepare the alkyl 2-hydroxy-3-naphthoic acid.

Description

technical field [0001] The invention relates to an alkyl 2-hydroxy-3-naphthoic acid and a preparation method thereof. Background technique [0002] 2-Hydroxy-3-naphthoic acid is a very important aromatic carboxylic acid compound. Its carboxyl group is a hydrophilic group, which can form a hydrogen bond with water. Generally, a hydrophobic group is obtained through an alkylation reaction to obtain a surface Active agent, widely used in medicine, pigment and lubricating oil and other fields. However, since the carboxyl group is a strong passivating group, it is very difficult to alkylate it. [0003] CN201080022786.7 reports a method for alkylating aromatic compounds using a shape-selective zeolite catalyst. The process has reactors in series and separates C8+ aromatics from the product stream effluent from each reactor before passing the reactor effluent to the next reactor along with an additional charge of methanol. Separation of C8+ aromatics into p-xylene and other C8+...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/11C07C51/353
CPCC07C51/353C07C65/11
Inventor 梁依经杨鹏伏喜胜管飞
Owner PETROCHINA CO LTD