CN103833541A

CN103833541A - Novel synthesis method of 2-methyl-1,4-naphthoquinone

Info

Publication number: CN103833541A
Application number: CN201410091125.XA
Authority: CN
Inventors: 黑晓明; 刘金华; 魏明志; 张术栋; 赵超
Original assignee: Qilu University of Technology
Current assignee: Qilu University of Technology
Priority date: 2014-03-13
Filing date: 2014-03-13
Publication date: 2014-06-04

Abstract

The invention relates to a novel synthesis method of 2-methyl-1,4-naphthoquinone. The novel synthesis method comprises the steps: respectively dissolving a defined amount of 2-methylnaphthalene and metachloroperbenzoic acid in moderate glacial acetic acid to prepare solutions (1) and (2), dropwise adding the solution (2) in the solution (1) under the stirring, after reacting for a period of time at a certain temperature, extracting a reaction solution by using chloroform, washing an extraction solution with a saturated NaHCO3 solution and water, after anhydrous Na2SO4 is dried, performing reduced pressure distillation to prepare a crude product of the 2-methyl-1,4-naphthoquinone, and recrystalizing by using alcohol as a solvent to obtain a pure product of the 2-methyl-1,4-naphthoquinone. According to the novel synthesis method, the conversion rate of the 2-methylnaphthalene can reach 80 percent, and the yield of the 2-methyl-1,4-naphthoquinone can reach 31 percent. The method disclosed by the invention has the characteristics of short reaction time, mild conditions, and the like, and products are easily separated; and no any catalyst is used in the reaction, thus the energy consumption and the environment pollution can be reduced.

Description

A kind of novel synthesis of 2-MNQ

Technical field

The novel synthesis that the present invention relates to a kind of 2-MNQ, belongs to the field of chemical synthesis.

Background technology

2-MNQ is vitamin K ₃activeconstituents, K is deficient in vitamin ₃animal, its can significant prolongation in clotting time, when famine, slight scratch will cause haemophilia and cause death.In aquatic products, livestock-raising, in order to promote growth of animal and preventing disease, usually in feed, add hormone and antibiotic, cause animal vitamin K ₃shortage.Therefore, in feed, add vitamin K ₃, supplement vitamin K in animal body ₃content, can effectively prevent and treat livestock and poultry hemorrhagic diseases.In addition, 2-MNQ can produce active O through yellow enzyme catalysis induction ^2-, H ₂o ₂and OH ^-thereby, destroy the catalase in tumour cell, produce cytotoxicity, suppress or tumoricidal growth, therefore, can be used for clinically the assisting therapy of some cancer.2-MNQ is also that synthetic other K is raw material and the important intermediate of VITAMIN simultaneously.

The prior synthesizing method of 2-MNQ is take 2-methylnaphthalene as raw material, uses chromic acid in acetic acid or sulphuric acid soln, to be oxidized preparation.The 2-MNQ yield obtaining is in this way lower; Reaction is made medium with strong acid, and corrodibility is strong, higher to equipment requirements; And can produce a large amount of chromate waste waters, environmental pollution is serious.Therefore, recent domestic scholar is making great efforts the synthesis technique of high, the environmental protection of exploitation productive rate always.

Summary of the invention

The novel synthesis that the object of this invention is to provide a kind of 2-MNQ, it is short that the inventive method has the reaction times, mild condition, product is easy to the features such as separation, and does not use any catalyzer in reaction, can reduce energy consumption and environmental pollution.

The synthetic method that the present invention takes, its step is as follows:

1) a certain amount of 2-methylnaphthalene and metachloroperbenzoic acid are dissolved in respectively in appropriate Glacial acetic acid and are mixed with solution (1) and (2), under stirring, solution (2) is dropwise splashed in solution (1), react for some time at a certain temperature;

2) reaction solution chloroform extraction, saturated NaHCO ₃solution, water washing, anhydrous Na ₂sO ₄after dry, underpressure distillation can obtain the thick product of 2-MNQ;

3) 2-MNQ crude product adds ethanol, activated carbon, heating for dissolving, and filtered while hot, filtrate cooling crystallization, suction filtration is dry, obtains 2-MNQ sterling.

Described oxygenant is metachloroperbenzoic acid.

Described 2-methylnaphthalene and the molecule mol ratio of metachloroperbenzoic acid are preferably 1:2.2.

Described temperature of reaction is preferably 25 ℃, and the reaction times is preferably 45min.

Beneficial effect of the present invention:

1, in the inventive method, reaction at room temperature can be carried out, and the reaction times is only 45min, can reduce energy consumption, and in reaction, excessive oxygenant metachloroperbenzoic acid can be used saturated NaHCO ₃solution washing is removed, and product separation is simple;

2, in the inventive method, do not use any catalyzer, can reduce environmental pollution.

Embodiment

Embodiment 1

Take 1.42g2-methylnaphthalene and 3.80g metachloroperbenzoic acid, be dissolved in respectively wiring solution-forming (1) and (2) in 10mL and 22mL Glacial acetic acid, under stirring, solution (2) is dropwise splashed in solution (1), under room temperature, react 45min; Reaction solution chloroform extraction, saturated NaHCO ₃solution, water washing, anhydrous Na ₂sO ₄dry, underpressure distillation can obtain the thick product of 2-MNQ, and crude product adds ethanol, activated carbon, heating for dissolving, and filtered while hot, filtrate cooling crystallization, suction filtration is dry, obtains light yellow crystal, i.e. 2-MNQ sterling, productive rate 30.49%.

Embodiment 2

Take 1.42g2-methylnaphthalene and 3.80g metachloroperbenzoic acid, be dissolved in respectively wiring solution-forming (1) and (2) in 10mL and 22mL Glacial acetic acid, under stirring, solution (2) is dropwise splashed in solution (1), 50 ℃ of reaction 45min; Reaction solution chloroform extraction, saturated NaHCO ₃solution, water washing, anhydrous Na ₂sO ₄dry, underpressure distillation can obtain the thick product of 2-MNQ, and crude product adds ethanol, activated carbon, heating for dissolving, and filtered while hot, filtrate cooling crystallization, suction filtration is dry, obtains light yellow crystal, i.e. 2-MNQ sterling, productive rate 14.85%.

Embodiment 3

Take 1.42g2-methylnaphthalene and 3.80g metachloroperbenzoic acid, be dissolved in respectively wiring solution-forming (1) and (2) in 10mL and 22mL Glacial acetic acid, under stirring, solution (2) is dropwise splashed in solution (1), under room temperature, react 1h; Reaction solution chloroform extraction, saturated NaHCO ₃solution, water washing, anhydrous Na ₂sO ₄dry, underpressure distillation can obtain the thick product of 2-MNQ, and crude product adds ethanol, activated carbon, heating for dissolving, and filtered while hot, filtrate cooling crystallization, suction filtration is dry, obtains light yellow crystal, i.e. 2-MNQ sterling, productive rate 21.78%.

Claims

1. the novel synthesis that the present invention relates to a kind of 2-MNQ, is characterized in that: the method comprises following steps:

2. the novel synthesis of 2-MNQ according to claim 1, is characterized in that: described oxygenant is metachloroperbenzoic acid.

3. the novel synthesis of 2-MNQ according to claim 1, is characterized in that: the molecule mol ratio of 2-methylnaphthalene and metachloroperbenzoic acid is preferably 1:2.2.

4. the novel synthesis of 2-MNQ according to claim 1, is characterized in that: temperature of reaction is preferably 25 ℃, and the reaction times is preferably 45min.