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Highly selective alkylated diphenylamine, its preparation method and application

An alkylated diphenylamine, high selectivity technology, applied in the preparation of amino compounds from amines, organic chemistry, additives, etc., can solve the high content of dialkylated diphenylamine, which is difficult to meet the production and application, and the residual amount of diphenylamine Many problems, to achieve the effect of simplified process, excellent anti-oxidation performance, and scientific and reasonable process route design

Active Publication Date: 2018-05-22
JIANGSU FEIYA CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] US5,269,961A, US5,308,884A etc. disclose to make α-methylstyrene and diphenylamine react with Filtrol 20X as catalyst, prepare the diphenylamine antioxidant of α-methylstyrene alkylation, its main deficiency The difference is that the product contains α-methylstyrene dimer and by-products of ortho-alkylation
[0015] In summary, although the prior art has all synthesized alkylated diphenylamines, they all have certain deficiencies, for example, the reaction temperature of some processes is too high, and the operation process is loaded down with trivial details; Incomplete; the content of dialkylated diphenylamine in the reaction products prepared by some processes is relatively high, so it is difficult to meet the requirements of production and application

Method used

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  • Highly selective alkylated diphenylamine, its preparation method and application
  • Highly selective alkylated diphenylamine, its preparation method and application
  • Highly selective alkylated diphenylamine, its preparation method and application

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preparation example Construction

[0031] In a more specific embodiment of the present invention, a method for preparing highly selective alkylated diphenylamine may comprise: reacting α-olefins and diphenylamine under the action of a solid acid catalyst in a reactor until the reaction The reaction is stopped when the content of diphenylamine in the product is less than 1 wt%, and the target product is obtained through post-treatment.

[0032] Wherein, the solid acid catalyst is selected from acid-treated porous structure materials, and its porous structure materials include any one or two or more of activated clay, activated carbon, silica gel, alumina, molecular sieves, zeolites, and ion exchange resins. combination, but not limited to this.

[0033] Wherein, the acid includes inorganic acid and / or organic acid.

[0034] Further, the inorganic acid includes sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, polyphosphoric acid, phosphotungstic acid, hydrofluoric acid, perchloric acid, boric acid...

Embodiment 1

[0053] Example 1 Add 60g (0.355mol) of diphenylamine and 9g of solid acid catalyst (15% of the weight of diphenylamine) into the reaction flask, heat up to the complete melting of diphenylamine, then add 61.50g (0.549mol) of diisobutylene, and heat up to 150 °C for 4 hours. The solid catalyst was removed by hot filtration, and the filtrate was distilled under reduced pressure to remove unreacted olefin and diphenylamine, and 97.38 g of light yellow liquid was collected. refer to figure 1 , based on high-performance liquid chromatography (HPLC) analysis, the pale yellow liquid contains 0.83wt% (% shown below, if not specified, it is all wt%) unreacted diphenylamine, 4.88% tert-butyldiphenylamine, 74.34 % monoisooctyl diphenylamine, 7.34% diisooctyl diphenylamine. The specific analysis results of the HPLC chromatogram are shown in the table below.

[0054]

Embodiment 2

[0055] Example 2 Add 60g (0.355mol) of diphenylamine and 30g of solid catalyst (50% of the weight of diphenylamine) into the reaction flask, raise the temperature to 60°C until all of the diphenylamine melts, then add 79.50g (0.710mol) of diisobutylene, and heat up React at 100°C for 12 hours. The solid catalyst was removed by hot filtration, and the filtrate was distilled under reduced pressure to remove unreacted olefin and diphenylamine, and 101.82 g of light yellow liquid was collected. Based on HPLC analysis, the light yellow liquid contained 0.70% unreacted diphenylamine, 4.45% t-butyldiphenylamine, 71.97% monoisooctyldiphenylamine, 9.34% diisooctyldiphenylamine.

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Abstract

The invention discloses high-selectivity alkylated diphenylamine and its preparation method and use. The preparation method comprises that alpha-olefin and diphenylamine undergo a reaction in the presence of a solid acid catalyst in a reactor until diphenylamine content of the reaction product is less than 1wt% and the reaction product is after-treated to form a desired product. The cheap and easily available solid acid catalyst is used and has good stability. In the reaction, the solid acid catalyst can effectively improve a raw material conversion ratio so that alkylated diphenylamine product selectivity is high and after the reaction, the reaction product and the catalyst can be separated easily. The preparation method has small equipment corrosivity, a short production period and simple processes, can be controlled easily and can prevent environment pollution caused by discharge of a lot of industrial waste water. The high-selectivity alkylated diphenylamine can be used as an additive in oil, plastic or rubber composition and can effectively improve antioxidant performances of the composition.

Description

technical field [0001] The invention relates to an antioxidant and its preparation method and application, in particular to a highly selective alkylated diphenylamine antioxidant, its preparation method and application, and belongs to the field of fine petrochemical industry. Background technique [0002] During the use of oil, plastic, and rubber, these materials will generate peroxides, alcohols, aldehydes, acids, esters, hydroxy acids and other compounds under high temperature or oxidative conditions, and these compounds can be further condensed to form macromolecular compounds , such macromolecular compounds seriously affect the quality of oil products, plastics, and rubbers. Therefore, in the process of oil blending and plastic rubber preparation, a certain amount of antioxidant additives need to be added to slow down the oxidation of these products and prolong their service life. . [0003] Alkylated diphenylamine has become the main antioxidant of various lubricating...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/68C07C211/55C10M133/12C10N30/10
Inventor 刘升高王立敏王声培刘烨曾红玲马玉杰贺军令
Owner JIANGSU FEIYA CHEM IND