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A kind of preparation method of dinonyl substituted diphenylamine antioxidant

A technology of nonylated diphenylamine and diphenylamine, applied in chemical instruments and methods, preparation of amino compounds from amines, physical/chemical process catalysts, etc., can solve the problem of reducing the antioxidant efficiency of alkylated diphenylamine, nano-mesoporous materials There are very few applied researches, cumbersome post-treatment process, etc., to achieve excellent oxidation resistance, improved reaction efficiency, and improved reaction selectivity.

Active Publication Date: 2020-07-14
JIANGSU FEIYA CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this process, a relatively large amount of starting material, usually 6-12% of the diphenylamine is unreacted, which reduces the antioxidant efficiency of the alkylated diphenylamine, leads to the precipitation of sludge, and makes the product have undesirable toxicity
US3496230 discloses to AlCl 3 As a catalyst, nonene and diphenylamine are catalyzed to prepare a mixture of nonylated diphenylamines. This invention embodies the AlCl 3 High activity and high selectivity of the catalyst, containing about 8% AlCl at 120-130°C 3 The catalyst is reacted for 6h to obtain 80% dinonylated diphenylamine and 15% monononylated diphenylamine. The disadvantage is that a large amount of sewage will be produced in the process of removing the aluminum chloride catalyst, and the aftertreatment process Complicated, the product color is darker
At present, there are very few studies on the application of nano-mesoporous materials in the preparation of alkylated anilines

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of Catalytic Component A - Bonded Support [HMIM]Cl / AlCl 3 mesoporous silica catalyst

[0054] (1) Preparation of acidic 1-hexyl-3-methylimidazolium chloride / aluminum trichloride ([HMIM]Cl / AlCl 3 ) chloroaluminate ionic liquid:

[0055] Add 0.1 mol of 1-hexyl-3-methylimidazolium chloride salt into a 100ml three-neck flask equipped with a nitrogen conduit, magnetic stirring, and heating device, heat to melt, control the temperature of the material at 80-90°C, and divide under the protection of nitrogen. Add 0.2 mol of aluminum trichloride in batches until the aluminum trichloride is completely melted to obtain the above-mentioned acidic alkylimidazolium salt / aluminum trichloride ionic liquid catalyst which is light yellow and transparent.

[0056] (2) [HMIM]Cl / AlCl obtained by the above steps 3 0.2 mol of ionic liquid and 0.2 mol of mercaptopropyltrimethoxysilane were placed in the reactor, 150 ml of acetonitrile solvent and 10 mmol of azobisisobutyronitril...

Embodiment 2

[0058] Preparation of cocatalyst flake nano-alumina:

[0059] Dissolve 4.2g of aluminum sulfate in 40mL of water, add 15mL of triethanolamine, stir at room temperature for 1h, then slowly add 6mL of 2M ethylenediamine and 6g of tetrabutylammonium hydroxide swelling agent dropwise, continue to stir at room temperature for 30min, then transfer to 100mL of water In a hot kettle, conduct hydrothermal treatment at 170°C for 8 hours, take it out and cool to room temperature, filter with suction, wash with water, dry, and bake in a muffle furnace at 500°C to obtain flaky nano-alumina. The sheet thickness of the obtained flaky nano-alumina is 23nm, the length is 1.8μm, and the specific surface area is 302cm 2 g -1 , the pore volume is 1.3cm 3 g -1 , with an average pore size of 33nm.

Embodiment 3

[0061] Preparation of nonylated diphenylamine

[0062] Carry out raw material proportioning according to following ratio: diphenylamine 84.7g (0.5 mole), 1-nonene 213.2g, the mesoporous silica catalyst 10g that embodiment 1 prepares, the phosphotungstic acid catalyst (loading capacity) of ZSM-5 molecular sieve load 10wt%) 4g, the flaky nano-alumina 5g that embodiment 2 prepares;

[0063] Concrete preparation steps are as follows:

[0064] (1) Take the weighed 84.7g diphenylamine and place it in a heatable 1000ml reactor with a stirrer, a thermometer and a reflux condenser and a water separator, and heat the mixed material in the reactor under nitrogen protection After the diphenylamine melts completely, start stirring, add the above composite catalyst and 108.2g of nonene, heat and reflux at normal pressure for 1h; slowly raise the temperature to 165°C at a heating rate of 2°C / min, keep the reaction for 3h, keep warm During the reaction period, a metering pump was used to gr...

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Abstract

The invention provides a method for catalytically preparing nonylated diphenylamine. The nonylated diphenylamine product is prepared through carrying out an alkylation reaction on diphenylamine and excessive nonylene in the presence of a composite catalyst system. A composite catalyst is prepared from the following catalyzing components: a catalyzing component A, a catalyzing component B and a flaky nano-alumina cocatalyst, wherein the catalyzing component A is selected from mesoporous silicon dioxide loaded alkyl imidazolium salt and aluminum chloride ionic liquid, the catalyzing component Bis selected from molecular sieve loaded heteropolyacid catalyst, and the content of dinonyl diphenylamine in the nonylated diphenylamine product is higher than 85%. According to the method provided bythe invention, the yield of dinonylated diphenylamine can be effectively increased, a chlorine element is hardly remained, and the quality of the antioxidant product is improved.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a preparation method of dinonylated diphenylamine as an antioxidant, and belongs to the fields of organic synthesis and antioxidant synthesis. Background technique [0002] During use, lubricating oils such as mineral oil and synthetic oil will react with oxygen in the air and metal surfaces to cause oxidative deterioration, acidic substances, and corrosion. In order to delay the oxidation process of the oil and improve the performance, the most effective way is to add antioxidants to the oil. At the same time, as the quality of lubricating oil is upgraded, lubricating oil is required to have lower phosphorus content, which means that phosphorus-containing antioxidant zinc dialkyldithiophosphate (ZDDP) will be used less, so non-phosphorus antioxidant Drugs are gradually gaining popularity. However, diphenylamine is directly used as an antioxidant, which has the disadvantages of ea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C211/55B01J31/26C10M133/12C10N30/10
CPCB01J31/26C07C209/68C10M133/12C10M2215/064C10N2030/10C07C211/55Y02P20/584
Inventor 李新君周元锋
Owner JIANGSU FEIYA CHEM IND
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