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Method for preparing liquid alkylated diphenylamine compound by ionic liquid catalyst

A technology of alkylating diphenylamine and ionic liquid, which is applied in the direction of condensation/addition reaction to prepare amino compounds, chemical recovery, organic chemistry, etc. It can solve the problems of high trioctyl diphenylamine and high residual diphenylamine, and achieve catalytic High efficiency, easy handling, color and stable effect

Inactive Publication Date: 2010-10-20
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to solve the problems in the prior art that the residual amount of diphenylamine is relatively high and the amount of trioctyldiphenylamine is relatively high, the present invention provides a method for preparing a liquid alkylated diphenylamine mixture. Ionic liquid catalyst, high catalytic efficiency, residual diphenylamine content <1%wt, and the product is light and stable

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0027] a. Preparation of ionic liquid catalyst

[0028] According to the molar ratio metal halide: quaternary cation = 0.8 ~ 10: 1, preferably 1 ~ 4: 1, at a temperature of 80 ~ 90 ° C, under the protection of nitrogen, slowly add the accurately weighed metal halide to the weighed In a good amount of molten quaternary cations, stir until the metal halide is completely melted to obtain a transparent ionic liquid catalyst.

[0029] Wherein the metal halide can be any one of iron trichloride, aluminum trichloride, indium trichloride, aluminum tribromide, boron trifluoride, boron tetrafluoride and the like. The quaternary cation may be selected from any one of quaternary ammonium ions, alkylimidazolium cations, and alkylphosphine cations. The quaternary ammonium cation is tetrabutylammonium chloride, butyltrimethylammonium, methyltriethylammonium, tetrabutylammonium bromide, benzyltrimethylammonium, n-hexyltrimethylammonium, n-hexyltrimethylammonium, Any one of n-octyltriethylam...

Embodiment 1

[0040] Add 0.1 mol of 1-butyl-3-methylimidazolium chloride salt into a 100ml three-necked flask equipped with a nitrogen conduit, magnetic stirring, and heating device, heat until melting, and control the temperature of the material at 80-85°C under nitrogen protection Add 0.20 mol of aluminum trichloride in batches, and after the aluminum trichloride is completely melted, a colorless or light yellow transparent ionic liquid catalyst which is liquid at room temperature is obtained.

[0041] Add 42.34g of diphenylamine (0.25mol) to a 250mL four-neck flask equipped with magnetic stirring, constant pressure dropping funnel, oil bath heating device, reflux condenser, temperature controller, and nitrogen conduit, heat to melt and pass nitrogen for 5-10 Minutes, then add 1.27g of the above-mentioned ionic liquid catalyst and stir, if the stirring stops, the ionic liquid catalyst will be deposited at the bottom of the flask. Weigh 39.2g (0.35mol) of diisobutene and place it in the dr...

Embodiment 2

[0043] Add 0.1 mol of 1-butyl-3-methylimidazolium chloride salt into a 100ml three-necked flask equipped with a nitrogen conduit, magnetic stirring, and heating device, heat to melt, and control the temperature of the material at 80-85°C under nitrogen protection Add 0.15 mol of aluminum trichloride in batches, and after the aluminum trichloride is completely melted, a colorless or light yellow transparent ionic liquid catalyst which is liquid at room temperature is obtained.

[0044] Add 42.34g of diphenylamine (0.25mol) to a 250mL four-neck flask equipped with magnetic stirring, constant pressure dropping funnel, oil bath heating device, reflux condenser, temperature controller, and nitrogen conduit, heat to melt and pass nitrogen for 5-10 Minutes, then add 1.06g of the above-mentioned ionic liquid catalyst, if the stirring stops, the ionic liquid catalyst will be deposited at the bottom of the flask. Weigh 42g (0.375mol) of diisobutene and place it in the dropping funnel. ...

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Abstract

The invention discloses a method for preparing liquid alkylated diphenylamine compound by an ionic liquid catalyst. Alkylate reaction is carried out on diphenylamine and alkene under the action of the catalyst; the catalyst is separated and recovered after the reaction finishes; steps of washing, pressure distillation for removing excessive alkene and water post treatment are carried out on the product; and then light yellow liquid alkylated diphenylamine compound is obtained. Pressure of the alkylated reaction is 1 atmospheric pressure and temperature thereof is 80-150 DEG C. The catalyst is ironic liquid catalyst, which is composed of metal halogenide anions and quaternary cations. Dioctyl diphenylamine content in liquid alkylated diphenylamine compound is less than 25% wt and diphenylamine content therein is less than 1%wt. Residual diphenylamine content in the obtained product is less than 1%wt and the ioctyl diphenylamine in the product is less than 25%wt; color and luster of the product is light and stable. The invention has simple and easy post-processing, does not generate a large amount of aluminiferous waste water and is easy to carry out industrialized promotion; in addition, the invention has high catalyst efficiency, repeatable use and easy separation from the product.

Description

technical field [0001] The invention belongs to the technical field of antioxidant organic synthesis, in particular to a preparation method of a liquid alkylated diphenylamine mixture. technical background [0002] Antioxidants are organic compounds that can inhibit or delay the thermal oxidation of polymers and other organic compounds in air. Amine antioxidants are one of the earliest antioxidants. Among them, hindered amine light stabilizers are a kind of organic amine compounds with steric hindrance effect. Transforming into the ground state, intervening in the photooxidation reaction before the photoaging chain is initiated, it is a highly efficient antioxidant. Alkylated diphenylamine belongs to this kind of antioxidant, which can be widely used in lubricating oil, engine oil, aircraft and various oil products applied under high operating temperature, polymer synthesis, rubber industry, etc. [0003] The synthesis of alkylated diphenylamine is usually prepared by the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/60C07C211/55
CPCY02P20/584
Inventor 郭伟杰
Owner JIANGSU UNIV OF SCI & TECH
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