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Preparation method of 2, 6-dihydroxytoluene in laboratory

A dihydroxytoluene, laboratory technology, applied in 2 fields, can solve the problems of product impurity, high production cost, great human injury, etc., and achieve the effect of stable product quality, low production cost and simple operation

Active Publication Date: 2013-03-27
ZAOZHUANG TAIRUI FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The disadvantage is: the main disadvantage of this synthetic route is that intermediates and products are difficult to purify, and the reaction process is not easy to control, resulting in high production costs and low overall yield
[0012] The disadvantage is: hydrogenation and dehydrogenation reactions will be carried out in the reaction process, both of which need to use a large amount of palladium carbon catalyst, and the reaction yield is low
[0015] Weaknesses are: this route uses 2,6-dinitrotoluene as starting raw material, obtains 2,6-diaminotoluene through high-pressure hydrogenation under palladium charcoal catalysis, then catalyzes with palladium charcoal under acid system, through high temperature (240°C) high-pressure hydrolysis to obtain 2,6-dihydroxytoluene product
[0019] Disadvantages: This method is a one-step reaction of resorcinol in ammonium chloride methanol system at 530°C under high temperature and high pressure to obtain the product
[0022] Disadvantages: This method is to introduce tert-butyl at the 4-position and 6-position of resorcinol first, then undergo an alkylation reaction under the action of methyl iodide, and then remove the tert-butyl group under the action of aluminum trichloride base get product
[0026] The disadvantages are: First, the raw material resorcinol is highly toxic and harmful to the human body, so the residual amount of resorcinol in the product must be very low
Second, the price of the raw material itself is relatively high, reaching 40,000 / ton
The third is that the reaction conditions are relatively harsh, and it is easy to introduce multiple carbon chains on the benzene ring, resulting in impure products and difficulties in subsequent product purification.
So far, this route is more in line with industrial production, but the price is still high, which limits the marketization of products
[0027] Some of the above synthesis methods are too expensive, some are not easy to operate, and some produce a large amount of waste acid and waste water, which are not conducive to industrial production
But as an important intermediate, 2-methylresorcinol has great application potential in many fields, especially in the fields of cosmetics and skin care products, and the price of 2-methylresorcinol is too high limit its application

Method used

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  • Preparation method of 2, 6-dihydroxytoluene in laboratory
  • Preparation method of 2, 6-dihydroxytoluene in laboratory
  • Preparation method of 2, 6-dihydroxytoluene in laboratory

Examples

Experimental program
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Effect test

Embodiment 1

[0047] Add 667g of 30% fuming sulfuric acid to the reaction flask, add 136g of p-toluic acid under stirring, raise the temperature to 180°C-195°C, keep the temperature for 5 hours, cool the reaction solution to below 100°C, add it to ice water, and cool Add sodium sulfate 1.8 times the mass of the raw material at 42°C-50°C; keep stirring at 42°C-50°C for 4 hours, cool to 25°C-30°C and centrifuge to obtain 388g of wet product;

[0048] Add 65g of water, 130g of sodium hydroxide and 130g of potassium hydroxide to an alkali fusion kettle, heat to 230°C and start stirring, slowly add 388g of sulfonated product when the temperature rises to 270°C; keep warm for 2.5 hours at 270°C-275°C Afterwards, hydrolyze with 600g of water, cool to 50°C and acidify with sulfuric acid until the pH value is 6-7, and filter the alkali fusion product when the temperature is lowered to 35°C, refine the alkali fusion product with water to adjust the crystallinity to 50°C, decolorize and filter the filt...

Embodiment 2

[0051] Add 667g of 30% fuming sulfuric acid to the reaction bottle, add 136g of p-toluic acid under stirring, raise the temperature to 185°C-198°C, keep it warm for 5 hours, cool the reaction solution to below 100°C, add it to ice water, and cool Add 245g of sodium sulfate to 42°C-50°C; keep stirring at 42°C-50°C for 4 hours, cool to 25°C-30°C and centrifuge. A small amount of sodium sulfate aqueous solution was rinsed to obtain 390 g of wet product;

[0052]Add 60g of water, 130g of sodium hydroxide and 130g of potassium hydroxide to the alkali fusion kettle, heat to 230°C and start stirring, add 390g of sulfonated product when the temperature rises to 270°C, keep it at 270°C-275°C for 2.5 hours before use Hydrolyze 600g of water, cool to 50°C with water, then acidify with sulfuric acid to pH 6-7, and filter to obtain alkali fusion product when the temperature is lowered to 35°C, adjust the crystallinity of the refined alkali fusion product to 50°C, decolorize and filter the ...

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Abstract

The invention discloses a preparation method of 2,6-dihydroxytoluene in a laboratory. The preparation method is characterized by comprising the following steps: 1, carrying out a sulfonation reaction; 2, carrying out an alkali fusion reaction; and 3, carrying out a decarboxylic reaction to obtain the 2, 6-dihydroxytoluene with the content of more than 92 percent. The preparation method disclosed by the invention has the advantages of being simple in production cost, easy and simple to operate and reliable in product quality.

Description

technical field [0001] The invention belongs to the field of chemical industry, in particular to a laboratory preparation method of 2,6-dihydroxytoluene. Background technique [0002] 2,6-dihydroxytoluene, also known as 2-methylresorcinol, is a white or off-white crystalline powder, easily soluble in water, the English name is: 2,6-dihyroxytoluene, the molecular formula is: C7H8O2, and the molecular weight is : 124, melting point: 118°C, boiling point: 264°C, structural formula: [0003] [0004] 2,6-Dihydroxytoluene is a very important fine chemical product, widely used in many fields such as medicine, pesticides, pigments, synthetic resins, photosensitive materials, hair dyes, etc., and because of its good disinfection and sterilization functions, in recent years It is also widely used in shampoos, skin care products and other products. And because the development and application of its downstream products are gradually increasing, the application field of this produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/08C07C37/00C07C37/04C07C37/84
Inventor 杨玉栋周志辉
Owner ZAOZHUANG TAIRUI FINE CHEM
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