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Preparation method of liquid antioxidant 4,6-di(octylsulfanylmethyl) o-cresol

An antioxidant, octylthiomethyl technology, which is applied in the field of preparation of liquid antioxidant 4,6-bis(octylthiomethyl)-o-cresol, can solve the problems of low product purity, difficult preparation, long reaction time and the like, To achieve the effect of simple industrial operation, improve product purity and shorten reaction time

Active Publication Date: 2013-11-27
RIANLON
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The method of the present invention is the same as other methods for preparing liquid antioxidant 4,6-bis(octylthiomethyl) o-cresol, all adopting o-cresol, n-octyl mercaptan and paraformaldehyde as raw materials, and the present invention overcomes It has been pointed out that the use of solid supported catalysts in other preparation methods is not easy to prepare, the recovery efficiency is low, and the catalytic activity is difficult to control; the use of organic catalysts is not environmentally friendly, the toxicity is high, and the catalyst residues are difficult to remove in the product; and the reaction time is long, the product purity is low, A new method established in response to the problems of high by-products of mono-adducts and dark product appearance

Method used

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  • Preparation method of liquid antioxidant 4,6-di(octylsulfanylmethyl) o-cresol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Replace the air in the 2000 liter reactor with nitrogen to pass. Add 400kg of o-cresol (3.699kmol, molar ratio is 1.0), n-octyl mercaptan 1055kg (7.212kmol, molar ratio 1.95) and paraformaldehyde 278kg (9.257kmol, molar ratio 2.50) into the reactor, and then inject 50kg of 95% ethanol, 7.8kg of industrial sodium carbonate solid (0.074kmol, molar ratio 0.02) was put into it. Turn on the stirring and condenser cooling water, and add 50 kg (0.366 kmol, molar ratio 0.10) of 33% dimethylamine aqueous solution at room temperature for 30 minutes. The material was heated up under stirring to the reflux temperature, and reacted at the reflux temperature for 5 hours.

[0031] 100 kg of deionized water was added to the obtained reaction solution, and the temperature of the solution was lowered to 42° C. under stirring, then the stirring was stopped and allowed to stand for 30 minutes, and then the lower aqueous phase 1 was carefully separated to obtain an organic phase 1 . Add 1...

Embodiment 2

[0035] Replace the air in the 2000 liter reactor with nitrogen to pass. Add 400kg of o-cresol (3.699kmol, molar ratio is 1.0), n-octyl mercaptan 1080kg (7.383kmol, molar ratio 2.00) and paraformaldehyde 278kg (9.257kmol, molar ratio 2.50) into the reactor, and then inject Methanol 80kg and deionized water 5kg, input industrial potassium carbonate solid 2.6kg (0.019kmol, molar ratio 0.005). Turn on the stirring and condenser cooling water, and add 222kg (1.477kmol, molar ratio 0.40) of 33% dimethylamine aqueous solution at room temperature for 30 minutes. The material was heated up under stirring to the reflux temperature, and reacted at the reflux temperature for 10 hours.

[0036] 320 kg of deionized water was added to the obtained reaction solution, and the temperature of the solution was lowered to 40° C. under stirring, and then the stirring was stopped and allowed to stand for 60 minutes, and then the lower aqueous phase 1 was carefully separated to obtain an organic pha...

Embodiment 3

[0040] Replace the air in the 2000 liter reactor with nitrogen to pass. Add 400kg o-cresol (3.699kmol, molar ratio is 1.0), n-octyl mercaptan 1110kg (7.588kmol, 2.05) and paraformaldehyde 400kg (13.320kmol, molar ratio 3.60) into the reactor, and then add 95% Add 40kg of ethanol and 4kg of deionized water, and put in 5.1kg of industrial potassium carbonate solid (0.037kmol, molar ratio 0.010). Turn on the stirring and condenser cooling water, and add 100kg (0.665kmol, molar ratio 0.18) of 30% dimethylamine aqueous solution at room temperature for 30 minutes. The material was heated up under stirring to the reflux temperature, and reacted at the reflux temperature for 3 hours.

[0041] Add 80 kg of deionized water to the obtained reaction liquid, cool the liquid to 40° C. under stirring, then stop stirring and let stand for 40 minutes, then carefully separate the lower aqueous phase 1 to obtain the organic phase 1 . Add 12 kg of formic acid to the organic phase 1, then add 80...

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Abstract

The invention relates to a preparation method of a liquid antioxidant 4,6-di(octylsulfanylmethyl) o-cresol. The preparation method comprises the following steps of: casting o-cresol, n-octyl mercaptan and paraformaldehyde in specified amount to a reaction kettle; adding a reaction solvent or then adding into water; casting a solid catalyst strong alkali and weak acid salt; then, starting stirring; continuously introducing or dropping an organic amine catalyst with a certain time; then, heating to reflux and performing reaction; after reaction, treating to obtain a product with high purity, less smell and low content of formaldehyde. The process is simple in industrial operation, low in cost and easy to realize. The yield based on o-cresol is greater than or equal to 98.0%, and the product obtained is approximately colorless. APHA is less than or equal to 10, and the product is transparent and the product purity is greater than or equal to 98.0%.

Description

technical field [0001] The invention relates to a preparation method of liquid antioxidant 4,6-bis(octylthiomethyl)o-cresol. The method adopts o-cresol, n-octyl mercaptan and paraformaldehyde as raw materials, reacts in the presence of the catalyst of the present invention, and obtains a high-purity, almost colorless product with a short reaction time and high yield. Background technique [0002] Liquid antioxidant 4,6-bis(octylthiomethyl)-o-cresol is an intramolecular synergistic antioxidant species containing hindered phenol and thioether in the molecule. It is used in plastics and synthetic rubber. It is easy to be emulsified. The polymerization solvent has good phase solubility and can be used safely, hygienically, efficiently and uniformly. In some application occasions, it can replace the existing antioxidants BHT and TNPP that can cause environmental pollution, and become green and environment-friendly antioxidants. [0003] Chinese invention patent CN102491925A use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/16C07C319/14
Inventor 汤翠祥范小鹏安平
Owner RIANLON
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