Method for preparing p-phenylenediamine rubber aging inhibitor

A technology of rubber anti-aging agent and p-phenylenediamine, which is applied in the field of rubber anti-aging agent preparation, can solve the problems of low quality of 4020 products, reduce the amount of MIBK, and more methyl isobutyl carbinol, and achieve large industrial application value , Reduce the difficulty of reaction, the effect of simple process

Inactive Publication Date: 2011-08-10
JIANGSU YANGNONG CHEM GROUP +2
View PDF6 Cites 31 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Chinese Patent Application Publication No. CN1170711A discloses a method for synthesizing p-phenylenediamine rubber antioxidant in an autoclave. It also uses a one-step method to synthesize rubber antioxidant 4020 by condensation hydrogenation reaction at 2-10MPa and 180-250°C. Reduce the amount of MIBK (the molar ratio of RT times to MIBK is 1:1.05~1.1). Although the yield of the product is relatively good, too little amount of MIBK will cause the viscosity of the reaction solution to be particularly large and the fluidity to be poor, resulting in catalyst failure. very difficult to recycle
In addition, the amount of methyl isobutyl carbinol (MIBC) produced by the reaction is relatively large (alcohol/ketone molar ratio ...

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing p-phenylenediamine rubber aging inhibitor
  • Method for preparing p-phenylenediamine rubber aging inhibitor
  • Method for preparing p-phenylenediamine rubber aging inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] (a) Condensation reaction

[0035] Into a 1L autoclave equipped with a condenser and an oil-water separator, put 150g (0.8mol) RT times and 120g (1.2mol) MIBK, when the temperature of the material in the reactor is raised to 130°C, the pressure is about 0.5MPa, and the heat preservation is started 4h. The temperature is controlled not to exceed 150°C. The oil-water separator brings out MIBK steam and water vapor. After condensation, MIBK and water enter the receiving tank for oil-water separation. Water is in the lower layer, MIBK is in the upper layer, and MIBK returns to high pressure from the overflow port on the upper part of the receiving tank. kettle. After the reaction was completed, the temperature was lowered and the pressure was released, and 13.9 g of water was separated from the receiving tank, and the remaining MIBK was returned to the autoclave, and the autoclave was poured out and weighed. The conversion rate of RT times was 97% according to sampling ana...

Embodiment 2～9

[0042] The experiment was carried out as in Example 1, except that the pressure, temperature and reaction time of the hydrogenation reaction step were different. The results of the conversion rate, selectivity and product purity of the hydrogenation reaction are summarized in Table 1.

[0043] Table 1 Experimental results using different hydrogenation process conditions

[0044]

[0045] The results show that the present invention has a good reaction effect at low temperature (about 100°C) and low pressure (1.0-4.0 MPa), and the product purity can reach more than 98%.

Embodiment 10～16

[0047] The experiment was carried out as in Example 1, except that the catalysts used in the hydrogenation reaction were Raney Ni, amorphous Ni, diatomaceous earth loaded Ni, 0.8%Pd / C, 5%Pd / C, 2%Pt / C, 5%Pt / C. The hydrogenation reaction conditions are the same as in Example 1. The experimental results are summarized in Table 2.

[0048] Table 2 Experimental results using different hydrogenation catalysts

[0049]

[0050] The results show that the conversion rate of the noble metal catalyst is high, while the conversion rate of the Ni catalyst is slightly lower, but the purity of 4020 is relatively high, and the cost of the Ni catalyst is much lower than that of the noble metal catalyst, which can effectively reduce the production cost.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a method for preparing a p-phenylenediamine rubber aging inhibitor, and relates to the technical field of chemical synthesis. The method comprises the following steps of: adding 4-aminodiphenylamine and partial methyl isobutyl ketone into a condensation reaction kettle, performing condensation reaction at a certain temperature under certain pressure, removing water generated by the reaction, and obtaining a condensation solution; adding the condensation solution, a hydrogenation catalyst and replenished methyl isobutyl ketone into the reaction kettle, performing hydrogenation reaction at a certain temperature under certain pressure, and obtaining a hydrogenation solution; and performing post treatment on the hydrogenation solution to obtain the p-phenylenediamine rubber aging inhibitor 4020, wherein the hydrogenation catalyst is a nickel, palladium or platinum catalyst. From the practice of industrial production, the rubber aging inhibitor 4020 is synthesized by adopting two-step reaction of condensation and hydrogenation; the difficulty of the hydrogenation reaction is reduced; and the requirement on the catalyst is reduced. The method has mild reaction conditions, high product quality and simple flow and no pollution, and is easy to realize industrialization.

Description

technical field [0001] The present invention relates to a preparation method of rubber anti-aging agent, more specifically, relates to a method for preparing p-phenylenediamine rubber anti-aging agent 4020 through hydrogenation, reduction and alkylation of 4-aminodiphenylamine and methyl isobutyl ketone. Background technique [0002] P-phenylenediamine antioxidant is currently the most widely used type of antioxidant in the rubber industry. They can inhibit the ozone aging, fatigue aging, thermo-oxidative aging and catalytic oxidation of metal ions of rubber products. Rubber anti-aging agent 4020, the chemical name is N-(1,3-dimethylbutyl)-N'-phenylenediamine, which belongs to the anti-aging agent of p-phenylenediamine with anti-aging agent 4010NA. Solvent rubber antioxidant. In natural and synthetic rubber, it has good protective effect against ozone and flex aging; it also has good protective effect against general aging such as oxygen and heat and harmful metals such as...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C211/55C07C209/70C08K5/18
Inventor 程晓曦徐林丁克鸿顾志强孙诚茅爱梅曹美荣袁源戚键楠马庆炎
Owner JIANGSU YANGNONG CHEM GROUP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap