Mixed-alkene-participating preparation method of nonyl diphenylamine

A technology of nonyl diphenylamine and diphenylamine, which is applied in the field of nonyl diphenylamine preparation, and can solve the problem that the catalyst cannot be recycled.

Active Publication Date: 2015-05-20
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The purpose of the present invention is to provide a preparation method of nonylated diphenylamine with the participation of mixed olefins. Compared with the current preparation method, the method adopts a new catalyst system and adds mixed olefins, which can effectively improve the diphenylamine in the alkylation reaction. The conversion rate of aniline reduces the residual amount of diphenylamine, improves the color of the product, increases the alkali value of the product, greatly reduces the discharge of waste gas and wastewater, and successfully solves the problem that traditional catalysts cannot be recycled

Method used

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  • Mixed-alkene-participating preparation method of nonyl diphenylamine
  • Mixed-alkene-participating preparation method of nonyl diphenylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0037] Add 50.0 g of diphenylamine and 12.5 g of aluminum trichloride into a 500 ml glass container equipped with a stirrer, a thermometer, a heating mantle, a reflux condenser, a water separator, and a nitrogen pipeline, feed nitrogen, and melt at 80° C. Add 140g of C9 olefin to gradually increase the temperature to 148°C, stir with a magnetic stirrer, control the reflux speed and heating temperature, so that the temperature of the reactant is not lower than 130°C, and the reaction time is 14 hours. According to the TLC tracking reaction until the DPA content does not change, start vacuum distillation. After proper cooling, acid wash at 60°C, 5% NaOH alkali wash, water wash, silica gel decolorization, and vacuum distillation to obtain the final product and recover olefins. The content of diphenylamine in the product measured by chromatography is 6%, and the base number is 76.5.

Embodiment 2

[0039] Add 50.0 g of diphenylamine and 5.0 g of montmorillonite and active Al in a 500 ml glass container equipped with a stirrer, thermometer, heating mantle, reflux condenser, water separator, and nitrogen pipeline 2 o 3Catalyst, feed nitrogen, after melting completely at 80°C, add 32.6g C9 olefins and gradually increase the temperature to 155°C, after the temperature stabilizes, continue to add 70.0g olefins within 5 hours, the amount of polymerization inhibitor added is 40ppm, controlled The reaction temperature cannot be lower than 145°C, and the reaction time is 16 hours. According to TLC follow-up reaction when DPA content no longer changes, continue to add 20g styrene to react for 4 hours, start vacuum distillation, after proper cooling. Then carry out vacuum distillation, and finally filter at 60°C to obtain the final product, recover olefins and catalysts to continue the reaction. According to chromatographic analysis, the remaining amount of diphenylamine is not m...

Embodiment 3

[0041] Add 50.0 g of diphenylamine and 5.0 g of montmorillonite and active Al in a 500 ml glass container equipped with a stirrer, thermometer, heating mantle, reflux condenser, water separator, and nitrogen pipeline 2 o 3 The catalyst is fed with nitrogen, and after it is completely melted at 80°C, add 32.6g of C9 olefins and gradually raise the temperature to 155°C. After the temperature stabilizes, continue to add 70.0g of olefins within 5 hours, and control the reaction temperature not lower than 145°C. The reaction time was 16 hours. According to the TLC tracking reaction until the DPA content does not change, continue to add 24g of α-methylstyrene to react for 4 hours (this active olefin needs to be added carefully, the product is easy to form a solid), start vacuum distillation, after cooling properly. Then carry out vacuum distillation, and finally filter at 60°C to obtain the final product, recover olefins and catalysts to continue the reaction. According to the chr...

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Abstract

The invention relates to a mixed-alkene-participating preparation method of nonyl diphenylamine. The preparation method comprises the following steps: mixing diphenylamine with C9 alkene, adding a mixed catalyst of activated montmorillonite and active Al2O3 to carry out alkylation reactions at a temperature of 75 to 170 DEG C; then adding mixed alkenes and a polymerization inhibitor, filtering the reaction products, then subjecting the reactions products to reduced pressure distillation so as to obtain the nonyl diphenylamine, collecting the solid catalyst for cycle use, and collecting and recovering the alkenes for subsequence reactions. The provided preparation method can effectively improve the product appearance, increase the base number, and reduce the content of residual diphenylamine. The yield of the preparation method can reach 65-85%. The catalyst can be repeatedly used. Furthermore, no wastewater or waste gas is generated and the preparation method is environment-friendly therefore.

Description

technical field [0001] The invention relates to a preparation method of nonyl diphenylamine with the participation of mixed olefins. Background technique [0002] Nonylated diphenylamine is an important class of amine-type antioxidants. It has good high-temperature oxidation resistance, ash-free and phosphorus-free characteristics, and good oil solubility. It can enhance the synergistic effect between various additives and improve oil quality. grade. It is widely used in internal combustion engine oil. As lubricating oil has higher and higher performance requirements for additives, how to continuously improve the performance of nonyl diphenylamine on the basis of the original technology is the main direction of research on amine antioxidants. [0003] The conventional preparation method of nonylated diphenylamine is as follows: using diphenylamine as a raw material, under the catalysis of common Lewis acids such as aluminum trichloride, the primary product of nonylated dip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/55C07C209/68B01J21/16
CPCY02P20/584
Inventor 火鹏飞徐小红蒋虎王林春周旭光李建明薛卫国
Owner PETROCHINA CO LTD
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