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Synthesis method of compound 2,6 -di-tert-butyl-4-nitrosophenol

A technology of di-tert-butylphenol and nitrosophenol, which is applied in the field of synthesis of the compound 2,6-di-tert-butyl-4-nitrosophenol, which can solve the problems of cumbersome and complicated operation process, uncontrollable reaction and high production cost problem, to achieve the effect of simple process steps, avoiding the use of noble metal catalysts, and short reaction time

Inactive Publication Date: 2012-10-03
GANSU RES INSTION OF CHEM IND GRICI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method needs to be reacted at a low temperature of 0°C, and carbon tetrachloride, an expensive, highly toxic, and volatile solvent, is used as a recrystallization solvent to achieve the best yield of 92%. The operation process is cumbersome and complicated, and the reaction is not easy to control. high production cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 2,6-di-tert-butylphenol (5.20g, 25.00mmol) in 95% industrial ethanol (40.00ml), and slowly add concentrated sulfuric acid (1.30ml, 25.00mmol) dropwise at room temperature under stirring After the dropwise addition, sodium nitrite (3.50g, 50.00mmol) dissolved in water (10.00 ml) was slowly added dropwise at 10°C, and the dropwise addition was completed in 1.5h, and the temperature was kept for 2.5h. Chromatography (TLC) or high performance liquid chromatography tracking monitoring, after the complete reaction, the reaction time is 4h; the reaction liquid is directly distilled under reduced pressure, and the reaction solvent ethanol and water are recovered, and then the solid after the reduced pressure distillation is fully washed with water, and the Vacuum negative pressure filter (XEE6-02) was filtered and dried to obtain the crude product; the crude product was recrystallized with toluene to obtain a golden yellow product, namely 2,6-di-tert-butyl-4-nitrosophen...

Embodiment 2

[0032]Dissolve 2,6-di-tert-butylphenol (5.20g, 25.00mmol) in 95% industrial ethanol (40.00ml), under nitrogen protection, under stirring, at room temperature, slowly add concentrated sulfuric acid (1.30ml, 25.00mmol), after the dropwise addition, slowly add sodium nitrite (3.50g, 50.00mmol) dissolved in water (10.00 ml) dropwise at 15°C, dropwise in 1.5h, keep warm for 2.5h, the whole reaction process Use thin-layer chromatography (TLC) or high-performance liquid chromatography to track and monitor. After complete reaction, the reaction time is 4 hours; the reaction solution is fully washed with water, filtered with a vacuum negative pressure machine (XEE6-02), and dried to obtain yellow The solid is 2,6-di-tert-butyl-4-nitrosophenol, the yield is 97.0%, and the product purity is ≥99.0%. The filtrate after negative pressure filtration was distilled under reduced pressure to recover the reaction solvent.

Embodiment 3

[0034] Dissolve 2,6-di-tert-butylphenol (5.20g, 25.00mmol) in ethanol (40.00ml) with a mass percentage of 95%, and slowly add concentrated sulfuric acid (1.30ml, 25.00mmol ), after the dropwise addition, slowly add sodium nitrite (3.50g, 50.00mmol) dissolved in water (10.00 ml) dropwise at 15°C, complete the dropwise addition in 1.5h, keep warm for 2.0h, and use a thin film for the whole reaction process Layer chromatography (TLC) or high performance liquid chromatography tracking and monitoring, after complete reaction, the reaction time is 3.5h; the reaction liquid is directly distilled under reduced pressure, and the reaction solvent ethanol and water are recovered, and then the solid after vacuum distillation is fully washed with water , filter under negative pressure with a vacuum negative pressure filter (XEE6-02), and dry to obtain a crude product; the crude product is recrystallized with toluene to obtain a golden yellow product, which is 2,6-di-tert-butyl-4-nitrosophen...

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Abstract

The invention discloses a synthesis method of a compound 2,6 -di-tert-butyl-4-nitrosophenol, and belongs to the technical field of chemical synthesis. According to the method, ethanol is used as a reaction solvent, 2,6-di-tert-butyl phenol, concentrated sulfuric acid and sodium nitrite are used as raw materials to be subjected to a nitrosation reaction in a normal temperature and atmospheric condition under the protection of nitrogen; and a reaction solution is post-treated to obtain the compound 2,6 -di-tert-butyl-4-nitrosophenol. The raw materials adopted by the invention are low in cost and easy to obtain, and any catalyst is not used in the synthesis process, thereby avoiding the use in a noble metal catalyst in the traditional synthesis method, reducing the cost and being favorable for the environment; the process steps are simple, the reaction conditions are mild, the reaction time is short, the post-treatment is simple, the operation is simple and safe, and the purposes of fastness and efficiency are achieved; the yield of the final product is high (up to 99%), and the purity is high (more than or equal to 99.0%); and in the whole synthesis process, no waste gas, waste liquor and waste residue are generated, and reaction materials are recycled.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a synthesis method of compound 2,6-di-tert-butyl 4-nitrosophenol. Background technique [0002] Compound 2,6-di-tert-butyl-4-nitrosophenol (English name: 2,6-Di-tert-butyl-4-nitrosophenol, CAS number: 955-03-3, molecular formula: C14H21NO2, molecular weight: 235.32. For details, see Chemical Dictionary), which is an important hindered phenolic antioxidant intermediate, which is widely used in the thermal oxidation resistance of rubber, plastics, pharmaceuticals, synthetic fibers, food, petroleum products and cosmetics. The structural formula of 2,6-di-tert-butyl 4-nitrosophenol is as follows: [0003] [0004] At present, the method for synthesizing 2,6-di-tert-butyl 4-nitrosophenol mainly contains the following four processes: [0005] Route 1: In ethanol solvent, the reaction temperature is >90°C, react with hydrogen bromide, acetic acid, and 1,3-di-tert-butyl-2...

Claims

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Application Information

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IPC IPC(8): C07C205/21C07C201/06
Inventor 李卫平张鹏云刘茵霍利春张伟杨明波
Owner GANSU RES INSTION OF CHEM IND GRICI
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