Effect of Temperature on the Reaction of 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic Acid with Oxygen in an Alkaline Condition

DOI: 10.4236/aces.2015.53026   PDF   HTML   XML   2,421 Downloads   2,764 Views  

Abstract

Results of oxidation 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid oxygen depend on temperature. At 55 - 60, 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa is formed. The constitution is based on dates of spectrums 1Н and 13С NMR. At 95 - 97, mixtures of 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa and of 6,8-di-tert-butyl-3-(N-acetylamine)spiro(4,5)deca-1-oxa-5,8-dien-2,7-dione are produced. Structures are calculated by the method of Hartrii-Foka. Values of enthalpies and of entropies allow to assume dynamic isomerism.

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Volodkin, A. , Zaikov, G. , Kurkovskaja, L. , Lomakin, S. , Levina, I. and Koverzanova, E. (2015) Effect of Temperature on the Reaction of 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic Acid with Oxygen in an Alkaline Condition. Advances in Chemical Engineering and Science, 5, 262-269. doi: 10.4236/aces.2015.53026.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] Volodkin, A.A., Erohin, V.N., Burlakova, E.B., Zaikov, G.E. and Lomakin, S.M. (2013) Structure and Biological Properties of Sodium and Potassium 2-(Carboxy)-2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionates, The Journal of Chemical Physics, 32, 66-72. [In Russian]
[2] Volodkin, A.A. and Zaikov, G.E. (2014) Mechanism of Myocardial Infarction: Pathological Changes in Rats after Application of Anphen Sodium. Herald of Kazan Technological University, 17, 138-141. [In Russian]
[3] Volodkin, А.А., Zaikov, G.E., Kurkovskaja, L.N., Evteeva, N.M., Lomakin, S.M., Parshina, E.J., Gendel, L.J. and Rahbanova, Z.M. (2012) Synthesis of Biological Antioxidant in Reaction Etherification 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic Acid. Herald of Kazan Technological University, 15, 177. [In Russian]
[4] Volodkin, A.A., Kurkovskaja, L.N., Zaikov, G.E. and Lomakin, S.M. (2013) Formation 3,3’,5,5’-Tetra-tert-butyldi-phenoquinone and 3,3’,5,5’-tetra-tert-butyl-4’,4-di-hydroxydi-phenylе in Reaction 2-(N-acetylamine)-3-(3’, 5'-di-tert-butyl-4'-hydroxyphenyl)-propionic Acid with Thionyl Chloride. Herald of Russian Academy of Sciences, Series Chemistry, 2265. [In Russian]
[5] Volodkin, А.А., Zaikov, G.E., Kurkovskaja, L.N., Lomakin, S.M. and Sofina, S.J. (2013) Synthesis New Antioxidants into Reaction 2-(N-acetylamine)-3-(3’,5’-di-tert-butyl-4’-hydroxy-phenyl)-propionic acid with Hydrogen Chloride. Herald of Kazan Technological University, 16, 18-21. [In Russian]
[6] Volodkin, A.A., Malysheva, R.D. and Ershov, V.V. (1982) Oxidation Methyl Ether (3,5-di-tert-butyl-4-hydroxy-phenyl)-propionic Acid by Oxygen. Herald of Russian Academy of Sciences, Series Chemistry, 1594. [In Russian]
[7] Volodkin, AA., Lomakin, S.M., Zaikov, G.E. and Evteeva, N.M. (2009) Alkaline Hydrolysis of Diethyl N-Acetylamine-(3,5-di-tert-butyl-4-hydroxybenzyl)malonate. Herald of Russian Academy of Sciences, Series Chemistry, 900. [In Russian]
[8] Teuder, H.J., Rause, H. and Berariu, V. (1978) 3,5-Di-tert-butyltyrosin. Lieb. Ann, 1978, 757.
[9] Vystorop, I.V., Konovalova, N.P., Neljubina, J.V., Varfolomeev, V.N., Fedorov, B.S., . Sashenkova, T.E., Berseneva, E.N., Lysenko, K.A. and Kostjanovsky, R.G. (2010) Cycle Hydroxamoving Acids from α-Aminoacids. Herald of Russian Academy of Sciences, Series Chemistry, 127-134. [In Russian]

  
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