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This work focuses on degradation of α‐tocopherol and formation of α‐tocopherol degradation products in sunflower oil heated at frying temperature. We determined the content and measured the kinetics of α‐tocopherol, α‐tocopheryl quinone, α‐tocopheryl fatty acid formation in heated sunflower oil without aeration (So) and in aerated oil (air flow 20 L/h) (SoAir). During 10 h of So oil heating, the α‐tocopherol was depleted and the content of α‐tocopheryl quinone in So grew from 3 to 84 mg/kg, as did the content of tocopherol free fatty acid esters from the initial 5 to 185 mg/kg. In SoAir oil, the rate constants of formation and decomposition of tocopherol degradation products were determined. Accelerated oxidation in SoAir caused depletion of the degradation products of tocopherol after 2 h of heating. The reason for this was significant oxidation and polymerization of fatty acids in SoAir oil. The unique features of this work are the syntheses and spectral analysis of tocopherol oxidation products and the development of a suitable method for quantitative analysis of α‐tocopheryl fatty acids. For the first time, we confirmed formation and degradation of tocopheryl fatty acids during oil heating at frying temperature. Practical applications: All the results presented here, consisting of organic syntheses, qualitative and quantitative analysis of α‐tocopheryl fatty acids as well as oxidation and degradation products of tocopherols and fatty acids, will aid future research focused on the degradation of tocopherols. So far the content of α‐tocopheryl fatty acids has not been determined by GC‐FID or HPLC‐UV. This is why there has been little interest in α‐tocopheryl fatty acids, although they are formed both in culinary treatment of food and in oil refining. Free fatty acids (FFAs), fatty acids (FAs), oxidation [o], products (i) and products (ii) are unspecified products of α‐tocopheryl FAs and α‐TQ degradation. Degradation products of α‐tocopherol were formed in heated sunflower oil and further heating of oil caused decomposition of α‐tocopherol degradation products.

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The paper describes laboratory deodorization of rapeseed oil (Ro), model sunflower (SoM), and model rapeseed (RoM) oils, its effect on the tocopherol content and the kinetics of tocopherol degradation. We now present a novel approach to analysis of alpha‐tocopherol degradation product as well as kinetic study esters of alpha‐tocopherol with fatty acids and alpha‐tocopheryl quinones. Alpha‐tocopherol esters were found to be the principal products of tocopherols degradation in high temperature experiment. A laboratory deodorization, lasting 2 h caused formation of 70–128 mg/kg of alpha‐tocopherol esters in model oils and 25 mg/kg of alpha‐tocopherol esters in rapeseed oil without modification. The commercially available sunflower and rapeseed oils contained 3–12 mg/kg of alpha‐tocopherol esters. The alpha‐tocopherol esters are formed at higher rate than alpha‐tocopheryl quinone, which was unstable at high deodorization temperature. Tocopherols took no part in non‐radical thermal reactions, taking place in second high‐temperature experiments with oxygen‐free atmosphere. We proved by DART TOF‐MS the formation of polymeric fatty acids via Diels–Alder reaction taking place in heated oils. Practical applications: Although an extensive research have been conducted in the area of high‐temperature degradation of tocopherols, this is the first report on formation of fatty acids esters of tocopherols during oil deodorization. The proof of their presence in deodorized oils, deodorization condensates, deep‐fried foods, and oils constitutes a breakthrough. We ingested them as yet unknowingly. Their degradation is not nearly as fast as that of tocopherol itself or its oxidation products. In the course of their hydrolysis in stomach tocopheryls of fatty acids could thus become the source of unoxidized tocopoherols. We found out that during laboratory deodorization of vegetable oils were formed esters of tocopherols with fatty acids. During heating of oils are free fatty acids the acid catalyst of esterification.