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Preparation method of aralkyl salicylic acid derivative

A technology of aralkyl salicylic acid and its derivatives, which is applied in the field of preparation of aralkyl salicylic acid derivatives, can solve problems such as environmental pollution, easy catalyst residue, slow color development speed, etc., and achieve green synthesis process, effective Good for environmental protection and easy separation

Active Publication Date: 2016-02-03
锦州康泰润滑油添加剂有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japanese Patent Laying-Open 2-94,043, Japanese Patent Laid-Open 3-222,793, and Japanese Patent Laid-Open 4-129,789 use methanesulfonic acid as a catalyst, and also use inorganic strong acids (such as sulfuric acid) as a catalyst, which can significantly reduce the reaction temperature, but the catalyst is easy to remain. The color development speed of the product is slow when the color developer is prepared, and the color density is not enough
U.S. Patent No. 5,075,416 reports the use of methanesulfonic acid as a catalyst and n-hexane as a solvent to prepare aralkyl salicylic acid, which increases the cost of the solvent and the complexity of the post-treatment process
Chinese patent CN1,113,91 reports a method for synthesizing aralkyl salicylic acid using a three-way catalyst of glacial acetic acid-p-toluenesulfonic acid-sulfuric acid. The reaction temperature is 120-150°C, and the catalyst cannot be recycled, which increases the production cost and cause environmental pollution

Method used

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  • Preparation method of aralkyl salicylic acid derivative
  • Preparation method of aralkyl salicylic acid derivative
  • Preparation method of aralkyl salicylic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] In a 500ml three-necked flask equipped with a condenser, a thermometer and a mechanical stirrer, add 1-(3-sulfonic acid) propyl-3-methylimidazolium bisulfate ([C 3 SO 3 Hmim][HSO 4]) ionic liquid 10g, salicylic acid derivative 138.1g (1.0mol) as shown in formula (1), take by weighing 229.2g (2.2mol) of styrene derivative as shown in formula (2), first drop into 20g of styrene derivatives, heat up to 120°C, stir rapidly, then add the remaining part of styrene derivatives dropwise, drop for 8 hours, and react for 1 hour after dropping, stop stirring, static layering, phase separation to remove the lower catalyst, the upper layer The viscous material was distilled off under reduced pressure to remove unreacted olefins to obtain yellow viscous liquid aralkyl salicylic acid with a yield of 96.5%.

[0039] Among the above reaction materials,

[0040] M, X in formula (1) 1 and x 2 Both are H;

[0041] R in formula (2) 1 , R 2 , R 3 、X 3 、X 4 Both are H.

Embodiment 2

[0043] In a 500ml three-necked flask equipped with a condenser, a thermometer and a mechanical stirrer, add 1-(4-sulfonic acid) butyl-3-methylimidazolium bisulfate ([C 4 SO 3 Hmim][HSO 4 ]) ionic liquid 10g, salicylic acid derivative 166.2g (1.0mol) as shown in formula (1), take by weighing 130.0g (1.1mol) of styrene derivative as shown in formula (2), first drop into 20g of styrene derivatives, heat up to 100°C, stir rapidly, then add the remaining part of styrene derivatives dropwise, drop for 6 hours, react for 0.5 hours after dropping, stop stirring, static layering, phase separation to remove the lower catalyst, the upper layer The viscous material was distilled off under reduced pressure to remove unreacted olefins to obtain a yellow viscous liquid aralkyl salicylic acid derivative with a yield of 97.1%.

[0044] Among the above reaction materials,

[0045] In formula (1), M is methyl, X 1 for H, X 2 is 4-methyl;

[0046] R in formula (2) 1 is methyl, R 2 , R 3 ...

Embodiment 3

[0048] In a 500ml three-necked flask equipped with a condenser, a thermometer and a mechanical stirrer, add 1,1,3,3-tetramethyl-2-propanesulfonate guanidine bisulfate ([C 3 SO 3 TMGH][HSO 4 ]) ionic liquid 10g, salicylic acid derivative 182.2g (1.0mol) as shown in formula (1), take by weighing 176.3g (1.1mol) of styrene derivative as shown in formula (2), first drop into 20g of styrene derivatives, heat up to 140°C, stir rapidly, then add the remaining part of styrene derivatives dropwise, drop for 10 hours, react for 2 hours after dropping, stop stirring, static layering, phase separation to remove the lower catalyst, the upper layer The viscous material was distilled off under reduced pressure to remove unreacted olefins to obtain yellow viscous liquid aralkyl salicylic acid with a yield of 96.1%.

[0049] Among the above reaction materials,

[0050] In formula (1), M is n-butyl, X 1 is H, X 2 is 4-methoxy;

[0051] R in formula (2) 1 , R 2 , R 3 、X 3 is H, X 4 Fo...

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Abstract

The invention provides a preparation method of an aralkyl salicylic acid derivative. The method is characterized in that styrene or a derivative thereof reacts with salicylic acid or a derivative thereof in the presence of an ionic liquid catalyst. The method overcomes the disadvantages of present aralkyl salicylic acid synthesis technologies, and is an efficient and green aralkyl salicylic acid synthesis technology. The catalyst adopted in the invention settles to the bottom of a reactor after the reaction ends, is convenient to separate, and also has the advantages of multi-time repeated use, no emission of waste acids, and environment protection benefiting in case of guaranteeing good yield.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of aralkyl salicylic acid derivatives. Background technique [0002] Aralkyl salicylic acid can be used to synthesize pressure-sensitive carbonless copy paper color developer, and can also be used to synthesize aralkyl salicylate lubricating oil additives. Due to the convenience of writing, pressure-sensitive carbonless copy paper has been widely used in various industries. The color developer of the lower layer mainly uses the third-generation zinc salicylate resin instead. Alkyl salicylate compounds are widely used in the field of lubricating oil additives due to their good high-temperature detergency and certain anti-oxidation and anti-corrosion capabilities. [0003] At present, the synthesis of aralkyl salicylic acid is mainly prepared by the reaction of salicylic acid and aryl olefin. high. Patent US4,748,259 has reported the method of using p-toluen...

Claims

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Application Information

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IPC IPC(8): C07C65/105C07C51/353C07C69/84C07C67/347
CPCC07C51/353C07C67/347C07C65/105C07C69/94
Inventor 杨连成禹培根赵岷江郭鹏飞郭松陈冲汤万进袁汉民
Owner 锦州康泰润滑油添加剂有限公司
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