Fullerene C60 Derivatives as High-Temperature Inbibitors of Oxidative Degradation of Saturated Hydrocarbons

Fullerenes and their derivatives are promising compounds for future applications in science, industry, and medicines.

Thermally stable C60 molecule can trap several radicals and can potentially be used as protective substance against reactive oxygen species at high temperature. Czochara etal.[1]described the antioxidant behavior of C60 during the autoxidation of stearic acid (STA) over a wide range of temperatures, as a noncorrosive agent for effectively increasing the oxidative stability of lubricants. There are also some experimental evidence that fullerene derivatives can be active antioxidants. C60 with attached amine group exhibits higher efficiency than conventional antioxidants during autoxidation of cumene[2]. Enes et al.[3,4] found that [60]fullerene-flavonoid or [60]fullerene-BHT conjugates exhibit moderate antioxidant activity during autoxidation of cumene in homogeneous system at 30℃.

Czochara et al.[5]conjugated of C60 with four simple phenols(Figure 1), and studied their ability to inhibit the high temperature oxidation of saturated and unsaturated fatty acids.

Figure 1. Structures of Fullerene C60 derivatives.[5]

The overall kinetic parameters calculated by the Ozawa-Flynn-Wall method for nonisothermal oxidation of model hydarcarbons：saturated stearic acid (STA) and polyunsaturated linolenic acid (LNA). The results indicated that C60 and its derivatives are effective antioxidants during oxidation of pure STA, but not during oxidation of LNA. These findings indicate that conjugates of C60 and phenols are candidates for potential use in base oils or lubricants as new hybrid antioxidants able to work at temperatures above 100 ℃.

Reference
1. R. Czochara, P. Ziaja, P. Piotrowski, R. Pokrop, G. Litwinienko. C60 as an inhibitor of high temperature lipid oxidation. Carbon 2012,50, 3943-3946.
2. N. S. Allen, E. B. Zeynalov, K. Taylor, P. Birkett. Antioxidant capacity of novel amine derivatives of buckminsterfullerene: determination of inhibition rate constants in a model oxidation system. Polym. Degrad. Stab. 2009, 94, 1932-1940.
3. R. F. Enes, A. C. Tome, J. A. S. Cavaleiro, R. Amorati, M. G. Fumo, G. F. Pedulli, L. Valgimigli. Synthesis and antioxidant activity of [60]fullerene-BHT conjugates. Chem. -Eur. J. 2006, 12, 4646-4653.
4. R. F. Enes, A. S. F. Farinha, A. C. Tome, J. A. S. Cavaleiro, R. Amorati,S. Petrucci, G. F. Pedulli. Synthesis and antioxidant activity of [60]fullerene-flavonoid conjugates. Tetrahedron, 2009, 65, 253-262.
5. R. Czochara, J. Kusio, M. Symonowicz, and G. Litwinienko. Fullerene C60 derivatives as high-temperature inhibitors of oxidative degradation of saturated hydrocarbons. Ind. Eng. Chem. Res. 2016,55,9887-9894.

Last article：A9 series lubricants Next item：Essential oil compounds used to eliminate odors