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Preparation method for hindered bisphenol type antioxidant

A technology of antioxidant and phenolic type, which is applied in the field of preparation of lubricating oil antioxidant, can solve the problems of increasing solvent recovery cost and consuming large solvent, and achieve better product color, simple production process and saving raw materials

Active Publication Date: 2016-05-18
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method uses strong base NaOH, KOH solid as catalyst and industrial alcohol as solvent to prepare hindered bisphenol compound, i.e. 4,4'-methylene bis(2,6-di-tert-butylphenol). A large amount of solvent needs to be consumed in the process, and its consumption is 5-10 times (molar ratio) of 2,6-di-tert-butylphenol. At the same time, excessive use of solvent will increase the recovery cost of solvent

Method used

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  • Preparation method for hindered bisphenol type antioxidant
  • Preparation method for hindered bisphenol type antioxidant
  • Preparation method for hindered bisphenol type antioxidant

Examples

Experimental program
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Effect test

Embodiment 1

[0061] Add 422g (2.05mol) of 2,6-di-tert-butylphenol and 10mL of mixed acid solution (5mL of acetic acid and 5mL of phosphoric acid) into a 1L reactor equipped with mechanical stirring, a thermometer and a reflux condenser, and heat in a water bath at 60°C , when 2,6-di-tert-butylphenol was fully melted, 99.48mL formaldehyde solution (37wt%) (1mol) was added dropwise, after the dropwise addition was completed, stirred in a constant temperature water bath at 70°C for 3 hours. Wash with deionized water at 50°C for 4 times, using 400 mL of deionized water each time, until the washing liquid is neutral, vacuum-dry for 24 hours after suction filtration under reduced pressure. Recrystallize with 800mL of toluene and isooctane mixed solvent, each of toluene and isooctane is 400mL, after suction filtration and vacuum drying, 360g of yellow needle-like crystals are obtained. The yield is 85% and the purity is 99.7%.

[0062] And characterize the obtained product, the characterization r...

Embodiment 2

[0068] Add 226.6g (1.1mol) of 2,6-di-tert-butylphenol and 8.8mL of mixed acid solution (4.4mL of acetic acid and 4.4mL of formic acid) into a 500mL three-necked flask equipped with mechanical stirring, a thermometer and a reflux condenser. Stir in a water bath at 40°C. After 2,6-di-tert-butylphenol is fully melted, add 46mL of formaldehyde solution (40wt%) (0.5mol) dropwise. After the addition is complete, stir in a constant temperature water bath at 80°C for 4 hours. Wash with deionized water at 40°C for 5 times, using 200 mL of deionized water each time, until the washing solution is neutral, vacuum-dry for 24 hours after suction filtration under reduced pressure. Recrystallize with 300mL toluene and isooctane mixed solvent, 150mL each of toluene and isooctane, filter with suction, and vacuum dry to obtain 191g of yellow needle-like crystals, the yield is 90% and the purity is 99.6%.

Embodiment 3

[0070] Add 422g (2.05mol) of 2,6-di-tert-butylphenol, 6.15mL of mixed acid solution (3.075mL of carbonic acid and 3.075mL of formic acid) into a 1L reactor equipped with mechanical stirring, a thermometer and a reflux condenser, at 50°C Stir in a water bath. After the 2,6-di-tert-butylphenol is fully melted, add 97.11 mL of formaldehyde solution (37 wt%) (0.976 mol) dropwise. After the dropwise addition, stir in a constant temperature water bath at 60°C for 3 hours. Wash with deionized water at 45°C for 3 times, each time using 400 mL of deionized water, and vacuum-dry the filter cake for 24 hours after suction filtration under reduced pressure. Recrystallize with a mixed solvent of 600 mL of toluene and isooctane, 300 mL of toluene and 300 mL of isooctane, filter with suction, and dry in vacuum to obtain 368 g of yellow needle-like crystals. The detected yield was 87%, and the purity was 99.8%.

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Abstract

The invention relates to a preparation method for a hindered bisphenol type antioxidant. The preparation method comprises the following process steps: adding 2,6-ditert-butyl phenol and a catalyst into a reaction vessel, wherein per 1 mol of 2,6-ditert-butyl phenol is added with 3 to 8 mL of the catalyst; carrying out stirring under the temperature condition of 40 to 60 DEG C until the mixture is melted; adding a formaldehyde solution, wherein a mol ratio of formaldehyde and 2,6-ditert-butyl phenol is 1: (2.0-2.2); after the completion of addition, carrying out heating to 60 to 80 DEG C, carrying out reaction for 2 to 5 hours, then carrying out pumping filtration, and carrying out washing by using warm water with a temperature of 40 to 50 DEG C; subjecting an obtained filter cake to vacuum drying, and recrystallizing an obtained crude product, wherein per 1 g of the crude product is added with 0.5 to 5 mL of a recrystallization solvent; and carrying out vacuum drying so as to obtain a yellow needle-like crystal. The method provided by the invention does not need adding alcohol organic solvents in the preparation process, has the advantages of simple production process, low cost, few by-products in a preparation process, and high antioxidant purity and yield, and is beneficial for environmental protection.

Description

technical field [0001] The invention relates to a preparation method of a lubricating oil antioxidant, in particular to a preparation method of a hindered bisphenol antioxidant. Background technique [0002] Antioxidants can significantly improve the oxidation stability of lubricating oil and prevent oil from spoilage. Among different types of antioxidants, phenolic antioxidants represented by shielded phenols are very effective chain terminators. Hindered bisphenol antioxidants refer to phenolic antioxidants that directly link two hindered phenolic units with alkylene or sulfur bonds. Compared with the monophenol type, the bisphenol type has less volatilization and extraction loss, higher thermal stability, and better anti-aging effect. At present, there are few reports on the preparation process of the hindered bisphenol antioxidant, 4,4'-methylene bis(2,6-di-tert-butylphenol), and the existing domestic preparation process has many by-products. The products vary greatly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/20C07C39/16
Inventor 刘中国王辉孙大新
Owner PETROCHINA CO LTD
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