Preparation method of N-alkyl m-aminophenol

A technology of m-aminophenol and aminophenol, which is applied in the preparation of amino hydroxy compounds, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problem of low yield of N-alkyl m-aminophenol and primary conversion rate of resorcinol. Not high, not suitable for large-scale production and other problems, to achieve the effect of high selectivity, less impurities, easy industrial production

Active Publication Date: 2010-03-17
山东瑞康精化有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process route of this method is long, and it must go through the steps of reduction, alkylation, alkali fusion, acidification, etc., and the process is complex; and the reduction with iron powder will produce a large amount of waste residue, and the steps of alkali fusion and acidification will produce a large amount of waste water, causing environmental pollution. The cost is also high, not suitable for mass production
[0005] Japanese Patent JP55-105648 and U.S. Patent US5113018 disclose a method of N-alkyl m-aminophenol, firstly use resorcinol to react with organic amine under the action of catalyst and sol

Method used

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  • Preparation method of N-alkyl m-aminophenol
  • Preparation method of N-alkyl m-aminophenol
  • Preparation method of N-alkyl m-aminophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: prepare a kind of N-alkyl m-aminophenol, be main raw material with m-aminophenol and the bromoethane of general formula RX, use water as solvent, make deacidifying agent with NaOH, tin chloride is made selectivity catalyst;

[0026] The chemical formula of the reaction is as follows:

[0027]

[0028] Among them, R is C 2 h 5 , X is Br;

[0029] Add 1.0ml m-aminophenol, 1.25ml bromoethane, 327g water and 1.09g tin chloride in a 1500ml four-necked bottle, the quality of 1.0ml m-aminophenol is 109g, the quality of 1.25ml bromoethane is 136.5g, Heat up to 50°C and start reflux, then slowly add 200g of 30% NaOH solution dropwise to the bottle, wherein the NaOH content is 1.5mol, after adding the NaOH solution, continue to react for 7 hours, and use gas chromatography to detect and track the reaction , when the content of m-aminophenol <0.5%, the reaction solution is obtained, add 240ml toluene to the bottle, carry out standing, sedimentation, extraction...

Embodiment 2

[0035] Embodiment 2: prepare a kind of N-alkyl m-aminophenol, take m-aminophenol and bromoisobutane whose general formula is RX as main raw materials, use isobutanol whose general formula is ROH as solvent, and use KOH as desorbent Acid agent, tin chloride as selective catalyst;

[0036] The chemical formula of the reaction is as follows:

[0037]

[0038] Wherein, R is isobutyl, X is Br;

[0039] Add 1.0ml m-aminophenol, 1.1ml bromoisobutane, 54.5g isobutanol and 7.63g tin chloride to a 1500ml four-necked bottle, the quality of 1.0ml m-aminophenol is 109g, 1.1ml bromoisobutane The quality of the product is 150.7g, and the temperature is raised to 70°C to start reflux, and then 128.3g of KOH solution with a concentration of 48% is slowly added dropwise to the bottle, wherein the content of KOH is 1.1mol. After adding the KOH solution, the reaction is continued for 5 hours. Detect and follow the reaction situation with gas chromatography, when m-aminophenol content<0.5%, o...

Embodiment 3

[0045] Embodiment 3: prepare a kind of N-alkyl m-aminophenol, be main raw material with m-aminophenol and general formula RX bromoisopentane, be the isoamyl alcohol of general formula ROH as solvent, use Na 2 CO 3 As deacidification agent, tin chloride as selective catalyst;

[0046] The chemical formula of the reaction is as follows:

[0047]

[0048] Wherein, R is isopentyl, X is Br;

[0049] Add 1.0ml of m-aminophenol, 1.0ml of bromoisopentane, 218g of isoamyl alcohol and 5.45g of tin chloride in a 1500ml four-necked bottle. Quality is 151g, is warming up to 90 ℃ and begins to reflux, then slowly adds 424g concentration to the bottle and is 20% Na 2 CO 3 solution, where Na 2 CO 3 The content is 0.8mol, after adding Na 2 CO 3 After the solution, continue to react for 2 hours, use gas chromatography to detect and track the reaction situation, when the m-aminophenol content < 0.5%, the reaction solution is obtained, add 300ml toluene to the bottle, let stand, settle...

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PUM

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Abstract

The invention relates to a preparation method of N-alkyl m-aminophenol, which comprises the following steps: placing m-aminophenol and halogenated hydrocarbon in a reaction vessel containing a solvent, adding stannic chloride as a selective catalyst, then stirring while heating, starting reflux when the temperature reaches 30-90 DEG C, then adding an alkaliferous aqueous solution step by step, continuing to react for 1-10 hours to obtain a reaction liquid after the alkaliferous aqueous solution is added, then adding toluene into the reaction liquid, carrying out still standing, sedimentation and then extraction delamination to separate out an upper organic substance and a lower organic substance, filtering or rectifying the upper organic substance separated out through extraction delamination to obtain the high purity N-alkyl m-aminophenol. The reaction using water or corresponding alcohol as the solvent and stannic chloride as the catalyst has high selectivity, the product purity canreach more than 98 percent without refined purification, and the yield is high, the purification process in a traditional production method is saved, and the production cost is lowered.

Description

technical field [0001] The invention relates to a preparation method of materials used for producing heat-sensitive dyes and heat-sensitive paper additives, in particular to a preparation method of N-alkyl m-aminophenol, which belongs to the technical field of fine chemicals. Background technique [0002] N-Alkyl m-aminophenol is an important intermediate for the manufacture of fluoran dyes and heat-sensitive paper additives, and is widely used in chemical production, especially in the production of asymmetric fluoran series heat-sensitive dyes. Thermal recording paper is currently being used more and more widely, such as invoices, schedules, recording materials for ticket roll machines used in banks, taxation, post and telecommunications, hotels, etc., and recording paper for fax machines, computers, and instruments. [0003] Introducing different substituents into the structure of fluoran dyes and heat-sensitive paper additives can not only obtain monochromatic blacks of v...

Claims

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Application Information

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IPC IPC(8): C07C215/76C07C213/08
Inventor 李正元陈建平房玉香宋本玺蔺黎明
Owner 山东瑞康精化有限公司
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