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Method for synthesizing a variety of thiophenols by one-step method

A technology of thiophenol and synthetic method, which is applied in the field of chemistry/chemical industry, can solve the problems of only 69.3%, high price, high purity, etc., and achieve the effect of easy industrial production, no toxic and side effects, and simple operation

Inactive Publication Date: 2010-06-30
淄博市新材料研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] U.S. Patent 4877902 has reported the reaction of dialkylphenol and sulfur monochloride in the mixed solvent of nitroalkane and acetonitrile, and its main product is dithio and trithiodialkylphenol and precipitates rapidly from reactant as solid The production process, its highest solid yield is 83.8%, but the product in the solvent does not explain how to collect
U.S. Patent 4,898,980 reported a method for reacting 2,4-di-tert-butylphenol with sulfur monochloride when toluene was used as a solvent. After the reaction solution was distilled, acetonitrile was used as a recrystallization solvent for recrystallization, and the dithio product had a high purity , but the yield is only 69.3%
The above two reports use the highly toxic solvent acetonitrile, and toluene and nitromethane are also more toxic and expensive, making them unsuitable for industrialization.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 100 grams of 2,4-di-tert-butylphenol raw material and 400 milliliters of petroleum ether into a 1000 milliliter four-neck glass flask equipped with stirring, a thermometer sleeve and a constant pressure dropping funnel, cool with ice-salt water and keep the temperature at - 5~5 ℃, under the state of stirring, add the mixture of 33.9 grams of sulfur monochloride and 100 milliliters of petroleum ether added in the dropping funnel dropwise in the reaction flask with 2 hours, continue to stir for 3 hours. Filter and dry to obtain 25.4 g of monothiophenol. After the filtrate is vacuum evaporated to remove petroleum ether, add 100 ml of methanol and stir to crystallize and filter, distill a little methanol, add water to adjust the polarity of the solvent, continue to crystallize and filter, and dry to obtain dithiophenol, trithiophenol and other oligomeric thiophenols. A mixture of products, the total yield of the product is 93.9%.

Embodiment 2

[0018] Add 100 grams of 2,4-di-tert-butylphenol raw material and 350 milliliters of petroleum ether into a 1000 milliliter four-necked glass flask equipped with stirring, a thermometer sleeve and a constant pressure dropping funnel, cool with ice-salt water and keep the temperature at 5- 5 ℃, under stirring state, with 2 hours, the mixture of 33.9 grams of sulfur monochloride and 100 milliliters of petroleum ether added in the dropping funnel was added dropwise in the reaction flask, and continued to stir for 3 hours. Filter and dry to obtain 23.5 g of monothiophenol. After the filtrate evaporates petroleum ether in a vacuum, add 100 ml of methanol and stir to crystallize and filter. After distilling a little methanol, slowly add water, gradually adjust the polarity of the solvent, recrystallize, filter, and dry to obtain dithiophenol, trithiophenol and other low-density compounds. Mixture of polythio products. The total product yield is 94.7%.

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PUM

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Abstract

The invention relates to a method for synthesizing a variety of thiophenols by a one-step method, belonging to the technical field of chemistry / chemical engineering. 2,4 - di-tert-butyl phenol acts with sulfur chloride in a solvent to be synthesized to the thiophenols. The method is characterized by comprising the following steps: in a petroleum ether solvent, firstly dissolving out a thiophenol, filtering, evaporating a filter liquor, removing the petroleum ether solvent, and then recrystallizing to obtain the mixture of other thiophenols. With simple operation and low cost, the method adopting the petroleum ether solvent has no toxic and side effect, safety, environment protection and easy industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing various thiophenols in one step, and belongs to the technical field of chemistry / chemical industry. Background technique [0002] Thiophenol products, including monothioalkylphenols and dithioalkylphenols, are widely used in the petroleum industry as a highly efficient hindered phenol anti-aging agent. Because its molecule contains both hindered phenolic units and -S- units, it has dual functions of free radical scavengers and hydroperoxide decomposers. Compared with common antioxidants, thiobisphenol antioxidants have more -S- units in the molecule, so they are intramolecular composite antioxidants with better antioxidant effects. It can also be used together with ultraviolet absorbers, metal passivators, carbon black, etc., and has a good synergistic effect, and has little effect on the electrical properties of the product, so it is used in polyolefin materials, rubber products and synthetic materia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/10C07C321/26
Inventor 王文举郝仲华郭宽陆亚楠黄东华朱永国
Owner 淄博市新材料研究所
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