Abstract
Solutions of 5-vinyl-2-norbornene (VNB, 5-vinylbicyclo[2.2.1]hept-2-ene) and the related compounds 5-ethylidene-2-norbornene (ENB, 5-ethylidenbicyclo[2.2.1]hept-2-ene) and 2-vinyl-2-norbornane (VNN, 2-vinylbicyclo[2.2.1]heptane) in cyclohexane have been irradiated with γ-rays at 40°C. The initial radiation-chemical yields G 0 for the consumption of the solutes and the formation of final products of γ-radiolysis of the solvent cyclohexane have been determined. It has been shown that solute consumption and molecular hydrogen formation yields G 0(−RH) and G 0(H2), respectively, are linearly related to the first vertical ionization potential of the solute. The G 0 values of molecular hydrogen, cyclopentadiene (CPD), butadiene, and methylallene, minor products of γ-radiolysis (40°C) of liquid VNB, ENB, and dicyclopentadiene (tricyclo[5.2.1.02.6]decadiene-3.8), have been determined. It has been shown that the G 0 values of CPD formation linearly depend on the first vertical ionization potentials of γ-irradiated bicyclic dienes. It is concluded that the γ-irradiation of cyclohexane generates two kinds of radical cations, which differ in mobility and reactivity.
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References
G. B. Shul’pin, Catalysts 6 (4), 50 (2016).
A. Rahman, M. Mupa, and C. Mahamadi, Catal. Lett. 146, 788 (2016).
M. Kim, J. M. Ha, K. Y. Lee, and J. Jae, Catal. Commun. 86, 113 (2016).
O. V. Potapenko, V. P. Doronin, T. P. Sorokina, et al., Appl. Catal., A 516, 153 (2016).
D. V. Zlenko and S. V. Stovbun, Comput. Res. Model. 5, 813 (2013).
A. Phukon, S. Ray, and K. Sahu, Langmuir 32, 6656 (2016).
A. Bashir, S. Ahad, and A. H. Pandith, Ind. Eng. Chem. Res. 55, 4820 (2016).
M. O. Sergeev, A. A. Revina, S. A. Busev, et al., Nanotechnol. Rev. 3, 515 (2014).
I. Yu. Shchapin, O. V. Makhnach, V. L. Klochikhin, et al., Pet. Chem. 46, 415 (2006).
I. Yu. Shchapin, O. V. Makhnach, V. L. Klochikhin, et al., Pet. Chem. 50, 476 (2010).
Yu. G. Osokin, Pet. Chem. 47, 1 (2007).
K. Cao, X. Liu, Y. Zhang, et al., Ind. Eng. Chem. Res. 54, 7565.
M. V. Bermeshev, B. A. Bulgakov, A. M. Genaev, et al., Macromolecules 47, 5470 (2014).
K. Naskar, U. Gohs, and G. Heinrich, Polymer 91, 203 (2016).
Radiation Chemistry of Hydrocarbons, G. Földiak, Ed. (Akadémiai Kiadó, Budapest}, 1981}
Pikaev, A.K., Modern Radiation Chemistry: Radiolysis of Gases and Liquids (Nauka, Moscow, 1986) [in Russian].
Saraeva, V.V., Radiolysis of Hydrocarbons in Liquid Phase (Izd. Moskovskogo Univ., Moscow, 1986) [in Russian].
V. V. Voronenkov, Yu. G. Osokin, V. N. Baidin, and A. I. Rusakov, Teor. Eksp. Khim., No. 4, 472 (1985).
Gurvich, L.V., Karachentsev, G.V., Kondrat’ev, V.N., et al., Chemical Bond Energies, Ionization Potentials and Electron Affinity (Nauka, Moscow, 1974) [in Russian].
I. A. Shkrob, A. D. Liu, M. C. Sauer, et al., J. Phys. Chem. B 102, 3363 (1998).
T. Momose, T. Shida, and T. Kobayashi, Tetrahedron 42, 6337 (1986).
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Original Russian Text © I.Yu. Shchapin, O.V. Makhnach, V.L. Klochikhin, A.I. Nekhaev, 2017, published in Neftekhimiya, 2017, Vol. 57, No. 5, pp. 573–581.
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Shchapin, I.Y., Makhnach, O.V., Klochikhin, V.L. et al. Radiolysis products of the cyclohexane–bicyclic diene binary system. Pet. Chem. 57, 897–903 (2017). https://doi.org/10.1134/S0965544117100139
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DOI: https://doi.org/10.1134/S0965544117100139