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Preparation method for antioxidant 2,4-bi(n-octyl sulfur methylene)-6-methylphenol

An antioxidant, o-cresol technology, applied in the field of preparation of phenolic antioxidant 1520, can solve the problems of reducing product purity, limited application range, decolorization, etc., and achieves the effects of easy industrial production, simple process and simple operation

Inactive Publication Date: 2016-03-23
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purification method has complicated steps and is not suitable for industrial production
[0015] As can be seen from the above analysis, the existing methods, whether it is a "step-by-step method" or a "one-pot method", either have a reaction to generate the crude product 2,4-bis(n-octylsulfamethylene)-6- The color of methyl phenol product is deep, and the scope of application is limited, and needs further decolorization problem; Either there is unremoved n-octyl mercaptan in the product after distillation, and the method of raising temperature and increasing vacuum can not obtain ideal The problem of the effect, which will inevitably reduce the purity of the product, and the shortcomings of the odor of the product due to the residue of mercaptan

Method used

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  • Preparation method for antioxidant 2,4-bi(n-octyl sulfur methylene)-6-methylphenol

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add paraformaldehyde (18.86g, 0.63mol), o-cresol (15.51g, 0.14mol), n-octyl mercaptan (45.64g, 0.31 mol), piperidine (3.11 g, 0.037 mol), solvent DMF (28.0 mL). Nitrogen protection gas was passed, and the oil bath was heated. First, the temperature was slowly raised to 80°C, and the reaction was performed for about 1 hour. After the reaction was completed, the solvent, water, catalyst and excess raw materials were removed by distillation under reduced pressure to obtain 59.78 g of crude product. Add a mixed solution of 60.0 mL of anhydrous methanol and 10 mL of toluene to the crude product, shake well, and carry out low-temperature stirring and crystallization. Suction filtration after the product is precipitated, the filter cake is washed with anhydrous methanol, and the solid product is collected, the filtrate continues to be crystallized at low temperature, and suction filtration is repeated 3 times, and most of the product is precipitated. The crystalline products...

Embodiment 2

[0033] Add paraformaldehyde (36.54g, 1.22mol), o-cresol (31.32g, 0.29mol), n-octyl mercaptan (87.98g, 0.63mol), piperidine (2.68g, 0.071mol), solvent DMF (60.0mL). Nitrogen protective gas was passed through, and the oil bath was heated. First slowly raise the temperature to about 90°C, react for about 0.5h, the solution becomes transparent, then raise the temperature to about 100°C, and react for 7h. The solvent, water, catalyst and excess raw materials were removed by distillation under reduced pressure, and 122.14 g of crude product was obtained by cooling. Add a mixed solution of 110mL of anhydrous methanol and 20mL of toluene to the crude product, shake well, stir and crystallize at low temperature. After the product was precipitated, it was suction filtered, and the filter cake was washed with anhydrous methanol to collect the solid product. The filtrate continued to crystallize at low temperature, and was filtered by suction, and so circulated 3 times, and most of the...

Embodiment 3

[0035]Add paraformaldehyde (54.60g, 1.82mol), o-cresol (48.56g, 0.45mol), n-octyl mercaptan (141.62g, 0.97mol), piperidine (8.03g, 0.09mol), solvent DMF (90.0mL). Nitrogen protection gas was passed, and the oil bath was heated. First, the temperature was slowly raised to 85°C, and the reaction was performed for about 1 hour. The solvent, water, catalyst and excess raw materials were removed by distillation under reduced pressure, and 192.10 g of crude product was obtained by cooling. Add a mixed solution of 170mL of anhydrous methanol and 30mL of toluene to the crude product, shake well, stir and crystallize at low temperature. After the product was precipitated, it was suction filtered, and the filter cake was washed with anhydrous methanol to collect the solid product. The filtrate continued to crystallize at low temperature, and was filtered by suction, and so circulated 3 times, and most of the products were precipitated. The crystalline products obtained three times we...

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Abstract

The invention relates to a novel preparation method for antioxidant 2,4-bi(n-octyl sulfur methylene)-6-methylphenol. Under piperidine catalysis, raw materials, namely, o-methylphenol, paraformaldehyde and octyl mercaptan react to generate antioxidant 2,4-bi(n-octyl sulfur methylene)-6-methylphenol; after the reaction, a solvent, water generated through the reaction, a catalyst and excessive unreacted raw materials are removed, and a crude product is obtained; the crude product is refined through a crystallization or cooling washing method. The product obtained through the method is colorless and is free of the disgusting smell of octyl mercaptan.

Description

technical field [0001] The present invention relates to a preparation method of phenolic antioxidant 1520, specifically, under the catalysis of piperidine, the raw materials o-cresol, n-octyl mercaptan and paraformaldehyde are reacted and purified to obtain odorless , The preparation method of colorless antioxidant 1520 product. Background technique [0002] The antioxidant 2,4-bis(n-octylthiomethylene)-6-methylphenol, also known as antioxidant 1520, has the molecular formula C 25 h 44 OS 2 , the structural formula is as follows: [0003] [0004] 2,4-bis(n-octylthiomethylene)-6-methylphenol is a hindered phenolic antioxidant containing a thiol alkyl group, which has two functional groups of thioether and hindered phenol in its structure. Two types of groups with synergistic effect together provide antioxidant effect. 2,4-bis(n-octylthiomethylene)-6-methylphenol has the advantages of low toxicity, little color pollution and strong compatibility; Extremely low volati...

Claims

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Application Information

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IPC IPC(8): C07C323/16C07C319/14
Inventor 林富荣秦亮胡云静
Owner CHANGZHOU UNIV
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