Directional synthetic method of 2, 5-di tertiary butyl hydroquinone

A di-tert-butyl hydroquinone, directional synthesis technology, applied in the field of fine chemicals and chemical synthesis, can solve the problems of low purity, high production cost, waste of raw materials, etc., achieve high selectivity and atom economy, reaction The effect of low equipment requirements and reduced production costs

Active Publication Date: 2014-08-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (1) Using a large amount of organic solvents, the environmental pollution is more serious
Post-treatment of solvent residues increases process complexity
[0006] (2) The use of relatively expensive catalysts, such as p-toluenesulfonic acid, ionic liquids, modified solid catalysts, et

Method used

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  • Directional synthetic method of 2, 5-di tertiary butyl hydroquinone
  • Directional synthetic method of 2, 5-di tertiary butyl hydroquinone
  • Directional synthetic method of 2, 5-di tertiary butyl hydroquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Mix 2.757g of hydroquinone with 0.142g of oxalic acid, add into a three-neck flask equipped with a thermometer, a stirrer, a condenser, and a constant pressure dropping funnel, add 2ml of water into the three-necked flask, stir, and heat to 82°C; Add 3.100 g of butanol from a constant pressure dropping funnel until the solid in the three-necked flask is completely dissolved, mix 8.030 g of tert-butanol with 2.457 g of concentrated sulfuric acid, slowly add it to the three-necked flask, and keep it at 82°C for 2 hours; stop the reaction and wait for the system to After cooling, filter, and wash the solid filter residue with 5 mL of water, repeat the washing 4 times, and dry to obtain 4.694 g of crude product 2,5-di-tert-butylhydroquinone, yield: 84.32%.

[0038] 3.898 g of the product 2,5-di-tert-butylhydroquinone was obtained by recrystallization, with a purity of over 99% and a comprehensive yield of 70.03%.

[0039] The product after recrystallization was taken, and a...

Embodiment 2

[0041]Take 2.732g of hydroquinone, put it into a three-necked flask equipped with a thermometer, a stirrer, a condenser, and a constant pressure dropping funnel, add 2ml of water into the three-necked flask, stir, and heat to 83°C; Add in a constant pressure dropping funnel until the solids in the three-necked flask are completely dissolved. Mix 8.152g of tert-butanol with 1.966g of concentrated sulfuric acid and 0.491g of phosphoric acid to make a mixed acid solution, slowly add it into the three-necked flask, and keep it at 83°C for 2 hours; stop the reaction , after the system was cooled, filtered, and the solid filter residue was washed with 5 mL of water, repeated washing 4 times, and dried to obtain 4.637 g of crude product 2,5-di-tert-butylhydroquinone, yield: 84.06%.

[0042] Recrystallization obtained 3.887 g of 2,5-di-tert-butylhydroquinone with a purity of over 99% and a comprehensive yield of 70.47%.

[0043] Get the product after recrystallization, carry out with ...

Embodiment 3

[0045] Mix 5.505g of hydroquinone with 0.228g of oxalic acid, add to a three-neck flask equipped with a thermometer, agitator, condenser, and constant pressure dropping funnel, add 4ml of water, stir, and heat to 86°C; 6.044g of tert-butanol Add from the dropping funnel until the solid in the three-necked flask is completely dissolved, mix 10.704g of tert-butanol with 4.971g of concentrated sulfuric acid, slowly add to the three-necked flask, and keep at 86°C for 2h; stop the reaction, and filter the solid after the system is cooled. The filter residue was washed with 10 mL of water, repeated washing 4 times, and dried to obtain 9.277 g of crude product 2,5-di-tert-butylhydroquinone, yield: 83.46%.

[0046] 7.894 g of the product 2,5-di-tert-butylhydroquinone was obtained by recrystallization, with a comprehensive yield of 71.32% and a purity of over 99%.

[0047] The product after recrystallization was taken, and it was detected by FT-IR by KBr tablet method. The detection in...

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Abstract

The invention belongs to the fields of fine chemicals and chemical synthesis, and discloses a directional one-step synthetic method of 2, 5-di tertiary butyl hydroquinone. According to the method, tertiary butyl alcohol and hydroquinone are used as raw materials for directional synthesis of the 2, 5-di tertiary butyl hydroquinone in the presence of a catalyst and water as a solvent. The directional one-step synthetic method of the 2, 5-di tertiary butyl hydroquinone is simple and convenient in operation and low in requirement on equipment; the yield of the 2, 5-di tertiary butyl hydroquinone can reach 90%, the purity reaches more than 99%, almost all the raw materials are converted into the target product, the selectivity and high atom economy are high; the directional one-step synthetic method is less in catalyst attrition, and avoids the use of aromatic hydrocarbons and ketones and other organic solvents, and the reaction mother liquor can be used repeatedly, the pollution of the environment can be minimized.

Description

technical field [0001] The invention belongs to the field of fine chemicals and chemical synthesis, and in particular relates to a directional synthesis method of 2,5-di-tert-butylhydroquinone. Background technique [0002] 2,5-Di-tert-butylhydroquinone (DTBHQ) is an antioxidant widely used in resin, plastic, rubber and other chemical industries. It is suitable for the production and production of natural rubber, latex, synthetic rubber, oil and rubber. It is also a non-toxic, no bad smell, no pollution plastic anti-aging agent. [0003] Compared with other chemical products, there are not many studies on the synthesis process of DTBHQ, and the preparation methods are mostly: using hydroquinone and tert-butanol as raw materials, dehydration in organic solvents to generate DTBHQ. The prepared DTBHQ has disadvantages and deficiencies such as low yield, low purity, and poor physical appearance, and needs to undergo relatively complicated post-treatment processes, such as decol...

Claims

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Application Information

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IPC IPC(8): C07C39/08C07C37/16
CPCC07C37/16C07C39/08
Inventor 刘美凤刘坚
Owner SOUTH CHINA UNIV OF TECH
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