Improving synthetic hindered phenol antioxidants: learning from vitamin E

• Published in: Polymer degradation and stability Vol. 70; no. 1; pp. 89 - 96
• Main Authors: Breese, K.D., Lamèthe, J.-F., DeArmitt, C.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.01.2000; Elsevier Science
• Subjects: Antioxidant; Applied sciences; Compounding ingredients; Exact sciences and technology; Oxidation; Polymer industry, paints, wood; Stabilizers (antioxydants, antiozonants, etc.); Technology of polymers; Vitamin E; α-Tocopherol; α-Tocopherol; Oxidation; Antioxidant; Vitamin E; Substituent effect; Performance evaluation; Induction period; Additive; Structure activity relation; Model compound; Phenols; Acetylene derivative polymer; E-Vitamins; Experimental study; Tocopherol
• ISSN: 0141-3910; 1873-2321; 1873-2321
• DOI: 10.1016/S0141-3910(00)00094-X

The efficiency of various commercial hindered phenol antioxidants was studied using differential scanning calorimetry (DSC) to determine the oxidation induction time (OIT) of antioxidant solutions in squalane. It was observed that α-tocopherol has an exceptionally high antioxidant activity. In fact, after normalisation for the molecular weight and functionality of each antioxidant, α-tocopherol was twice as efficient as any of the commercial, synthetic, hindered phenols tested. Through measurements on a series of model compounds, it was possible to identify the aspects of α-tocopherol's chemical structure that are responsible for its exceptional antioxidant efficiency. The results showed that the para oxygen in α-tocopherol is largely responsible for its exceptionally high antioxidant activity. Most commercial synthetic hindered phenolic antioxidants are based upon 2, 6-di- tert-butyl-4-methylphenol (BHT). We compared the antioxidant efficiency of BHT with that of 2, 6-di- tert-butyl-4-methoxyphenol (BHA) and found that BHA was 94% more efficient. This implies that it may be advantageous to make new commercial hindered phenolic antioxidants that are based in the more effective BHA structure instead of the conventional BHT structure used today. It is expected that addition of a para oxygen (or other electron donating groups) to the aromatic ring of existing hindered phenolic antioxidants would significantly increase their activity.