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Preparation method of alpha-naphthylacetic acid

A technology of naphthalene acetic acid and naphthalene ethyl ketone ester, which is applied in the direction of carboxylate preparation, carboxylate preparation, carboxylate preparation, etc., can solve the problems of high environmental protection costs, expensive α-naphthylacetone, etc., and achieve production costs Low, easy to purify, high yield effect

Pending Publication Date: 2020-08-07
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, its raw material α-naphthyl ethyl ketone is relatively expensive; highly toxic and extremely smelly hydrogen sulfide gas and a large amount of waste water are inevitably produced during the reaction process and post-treatment, and the environmental protection cost is high

Method used

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  • Preparation method of alpha-naphthylacetic acid
  • Preparation method of alpha-naphthylacetic acid
  • Preparation method of alpha-naphthylacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In the reaction flask, add 120 mL (1.5 mol) of 1,2-dichloroethane, 14.8 g (0.111 mol) of anhydrous aluminum trichloride and 12.8 g (0.1 mol) of naphthalene; stir well and heat to 45 °C , add 12.3 mL (0.115 mol) monoethyl oxalyl chloride; react for 4 hours, after the reaction, pour the reaction mixture into 100 mL cold water, stir well and let it stand, separate the organic layer; wash the organic layer with 30 mL 5% hydrochloric acid After pickling, washing with water, and drying with anhydrous sodium sulfate, it was concentrated to obtain an oily product (product 1); product 1 was directly used in the next reaction without purification.

[0038] Add the above product 1 into the reaction flask, add 110 mL (1.98 mol) of ethylene glycol and 12 mL (0.32 mol) of hydrazine hydrate (85%); slowly raise the temperature to 130 °C under stirring, and react for 2 hours; then cool the reaction solution to Below 80 °C, add 26.9 g (0.48 mol) of potassium hydroxide, then heat the reac...

Embodiment 2

[0040]In the reaction flask, add 120 mL (1.24 mol) of carbon tetrachloride, 20.4 g (0.15 mol) of anhydrous zinc chloride and 12.8 g (0.1 mol) of naphthalene; after stirring evenly, heat to 55 °C, add 11.0 mL ( 0.12 mol) monomethyl oxalyl chloride; react for 4 hours, after the reaction, pour the reaction mixture into 100 mL of cold water, stir well and let stand, and separate several layers; the organic layer is pickled with 30 mL of 5% hydrochloric acid, washed with water, After drying over sodium sulfate, it was concentrated to obtain an oil (product 1); the product 1 was directly used in the next reaction without purification.

[0041] Add the above product 1 into the reaction flask, add 110 mL (1.36 mol) of 1,2-propanediol and 6.5 mL (0.21 mol) of anhydrous hydrazine; slowly raise the temperature to 130 °C under stirring, and react for 2 hours; then cool the reaction liquid to 80 Below ℃, add 12g (0.3 mol) sodium hydroxide, then heat the reaction mixture to 180 ℃ for 4 hour...

Embodiment 3

[0043] In the reaction flask, add 95 mL (1.48 mol) of dichloromethane, 35 g (0.134 mol) of anhydrous tin chloride and 12.8 g (0.1 mol) of naphthalene; mol) ethyl oxalyl chloride; reacted for 4.5 hours, poured the reaction mixture into 100 mL of cold water after the reaction was completed, stirred thoroughly and allowed to stand, separated into several layers; the organic layer was pickled with 30 mL of 5% hydrochloric acid, washed with water, After drying over sodium sulfate, it was concentrated to obtain an oil (product 1); the product 1 was directly used in the next reaction without purification.

[0044] Add the above product 1 into the reaction flask, add 135 mL (1.5 mol) of 1,4-butanediol and 18 mL (0.48 mol) of hydrazine hydrate (85%); slowly raise the temperature to 140 °C under stirring, and react for 2 hours; then Cool the reaction liquid to below 80°C, add 26.9 g (0.48 mol) of potassium hydroxide, then raise the temperature of the reaction mixture to 190°C for 4 hour...

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Abstract

The invention relates to the technical field of organic synthesis, and provides a preparation method of alpha-naphthylacetic acid. The invention aims to solve the problem that preparation of alpha-naphthylacetic acid is not economical and environmentally friendly in the prior art. The preparation method comprises the following steps: (1) dissolving naphthalene and Lewis acid in a solvent, carryingout heating, adding oxalyl chloride monoester, and carrying out a reaction to generate alpha-acetonaphthone acid ester; and (2) adding the alpha-acetonaphthone acid ester obtained in the step (1) andhydrazine hydrate into a high-boiling-point alcohol solvent, carrying out a heating reaction, adding a strong base, continuing the heating reaction, and adjusting a pH value to an acidic state afterthe reaction is finished so as to obtain alpha-naphthylacetic acid. According to the method, naphthalene and oxalyl chloride monoester which are cheap and easy to obtain are used as raw materials, alpha-acetonaphthone acid ester is prepared under the action of Lewis acid, and then a series of reactions are performed under the action of hydrazine hydrate to generate alpha-naphthylacetic acid, so the use of highly toxic cyanide is avoided, highly toxic or foul gas is not generated in the reaction process, only one product is produced, reaction conditions are mild, yield is high and cost is low.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of alpha-naphthaleneacetic acid. Background technique [0002] α-Naphthaleneacetic acid (α-Naphthalenelactic acid, molecular formula C 12 h 10 o 2 , CAS: 86-87-3), insoluble in water, safe and non-toxic to humans and animals, is a widely used plant growth regulator. α-naphthaleneacetic acid can promote the growth, flower preservation, fruit preservation and rooting of crops. Its main pharmacological functions are to promote plant cell division, enlargement, induce the formation of restless roots, increase fruit setting, promote metabolism and photosynthesis, and accelerate growth and development. [0003] The existing main synthesis methods of α-naphthaleneacetic acid are: ①Cyanide method. Naphthalene reacts with formaldehyde in hydrochloric acid system under the action of hydrogen chloride gas to generate chloromethylnaphthalene, which reacts ...

Claims

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Application Information

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IPC IPC(8): C07C51/02C07C57/40C07C51/00
CPCC07C51/02C07C51/00C07C249/16C07C67/343C07C57/40C07C251/86C07C69/738
Inventor 朱锦桃洪小平
Owner ZHEJIANG SCI-TECH UNIV
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