Preparation of N,N’,N”-triphenyl-1,3,5-phenyltriamine_Kain Industrial Additive

Background and overview^[1]

During the use of lubricating oil, oxidation reactions will occur under the influence of air, water, metal, etc., especially in high-temperature working environments, it will quickly oxidize and deteriorate, and lose its own functions. Therefore, antioxidants must be added to prevent the rapid oxidation of the lubricating oil and extend the working life of the lubricating oil. Antioxidants are important additives that can effectively extend the service life of lubricating oil and ensure the oxidation stability of lubricating oil at high temperatures. By substituting and modifying N, N’-diphenyl-p-phenylenediamine, the substituents are mainly alkyl or alkoxy groups such as methyl, ethyl, and methoxy. This type of antioxidant exhibits high thermal stability and strong sludge control capabilities in lubricating oils. However, the above-mentioned antioxidants all have defects to varying degrees. For example, amine polymers have dispersion problems in lubricating oils and serious sludge. The high-temperature effects of alkylated diphenylamines and substituted p-phenylenediamines still need to be further improved. N,N’,N”-triphenyl-1,3,5-phenyltriamine is an antioxidant with high thermal stability, strong sludge control ability, and can effectively extend the working life of lubricating oil. It is suitable for various lubrication applications. Oil. It has good solubility in various lubricating oils and good antioxidant effect at high temperatures, which can greatly extend the service life of lubricating oil. It has excellent antioxidant performance in high-temperature lubricating oil oxidation tests and has broad application prospects.

Preparation^[1]

The preparation of N,N’,N”-triphenyl-1,3,5-phenyltriamine is as follows:

（R=H）

Specific steps are: Take 0.5g of phloroglucinol (3.96mmol) and 1.44ml of aniline (15.86mmol) into a 10ml sealed reaction bottle, replace with nitrogen 3 times, add 0.2ml of concentrated HCl (mass concentration 37.5%, the same below) ) and 3 ml of toluene, seal the tube, and react at 120°C for 2 hours. After the reaction is completed, cool to room temperature, and the obtained product is suction filtered, washed three times with 10 ml of methanol, and dried to obtain 1.17 grams of milky white needle-like crystals of N, N’, N”-triphenyl-1,3,5-phenyltriamine. . The obtained product was subjected to a series of characterization tests and the results are as follows. The hydrogen nuclear magnetic spectrum shows: 1HNMR (400MHz, DMSO): δ=798 (s, 3H, 3 secondary amine hydrogens), 6.33-7.23 (m, 18H, Ar-H), 3.36 water peak, 2.50 deuterium band dimethyl oxide Sulfone standard peak.

Main reference materials

[1] CN201510426390.3 Phenyltriamine high-temperature antioxidant for lubricating oil and its preparation method