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A highly efficient antioxidant based on boron and a Schiff base bridged phenolic diphenylamine: synthesis,crystal structure and thermal and antioxidant properties
Authors:Shengpei Wang  Shasha Yu  Jianxiang Feng  Shenggao Liu
Abstract:Antioxidants can effectively protect vegetable‐oil‐based lubricants against oxidative degradation and prolong their service life. A novel compound, (E)‐4‐({3,5‐di‐tert‐butyl‐2‐[(diphenylboranyl)oxy]benzylidene}amino)‐N‐phenylaniline (BSPD) or {2‐[(4‐anilinophenyl)iminomethyl‐κN]‐4,6‐di‐tert‐butylphenolato‐κO}diphenylboron, C39H41BN2O, was synthesized by a one‐pot reaction of the Schiff base bridged phenolic diphenylamine 2,4‐di‐tert‐butyl‐6‐{N‐[4‐(phenylamino)phenyl]carboximidoyl}phenol (SPD) with phenylboronic acid. The corresponding single‐crystal X‐ray study revealed that the B atom in BSPD has a typical tetrahedral geometry, and the N,O‐chelated six‐membered ring adopts a chair conformation. According to thermogravimetric analysis, the 5% weight‐loss temperature of BSPD increases to 328 °C and the 95% weight‐loss temperature is up to 414 °C. More importantly, the antioxidant capability of BSPD in vegetable oil is much better than that of commercial antioxidants [diphenylamine (DPA) and 2,6‐di‐tert‐butyl‐4‐methylphenol (BHT)] and unmodified SPD.
Keywords:antioxidant  thermal analysis  boron  Schiff base bridged phenolic diphenylamine  crystal structure
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