Novel essentially distinct from already known (methods of hydrogenation of fullerenes (C60 and
C70) or fullerite) method for the synthesis of highly hydrogenated carbon molecules is developed;
such approach is perspective hydrogen capacity accumulators. First, the reactionary conditions
are created for the realization of the process of fullerenization as direct transformation of molecules
of aromatic hydrocarbons, pyridine and ethanol into carbon molecules, fulleranes
(С60Н8-С60Н60 and С70Н8-С70Н44) and quasi-fulleranes (CnHn-6-CnHn-2 (n = 20 - 46)) containing up to
5.7 wt% hydrogen. X-ray amorphous powders of hydrogenated carbon molecules in gram amounts
are obtained. Appreciable dehydrogenation of such samples of fulleranes and quasi-fulleranes at
~50°C is began, while dehydrogenation of synthesized from fullerene (or fullerite) fulleranes is
observed only at temperatures above 400°C. Methods of NMR, IR spectroscopy, mass spectrometry
MALDI and temperature-programmed desorption mass spectrometry EI are used for the study of
condensed products of fullerenization of precursors molecules.
References
[1]
Haufler, R.E., Conceicao, J., Chibante, L.P.F., et al. (1990) Efficient Production of C60 (Buckminsterfullerene), C60H36, and the Solvated Buckide Ion. Journal of the Chemical Society, 94, 8634-8636.
[2]
Peera, A., Saini, R.K., Alemany, L.B., et al. (2003) Formation, Isolation, and Spectroscopic Properties of Some Isomers of C60H38, C60H40, C60H42 and C60H44. European Journal of Organic Chemistry, 21, 4140-4145. http://dx.doi.org/10.1002/ejoc.200300350
[3]
Shigematsu, K., Abe, K., Mitani, M., et al. (1993) Catalytic Hydrogenation of Fullerenes in the Presence of Metal Catalysts in Toluene Solution. Fullerene Science and Technology, 1, 309-318. http://dx.doi.org/10.1080/15363839308011900
[4]
Talyzin, A.V., Dzwilewski, A., Sundqvist, B. and Tsybin, Y.O. (2006) Hydrogenation of C60 at 2 GPa Pressure and High Temperature. Journal of Physical Chemistry, 325, 445-451.
[5]
Luzan, S.M., Tsybin, Y.O. and Talyzin, A.V. (2011) Reaction of C60 with Hydrogen Gas: In Situ Monitoring and Pathways. Journal of Physical Chemistry C, 115, 11484-11492. http://dx.doi.org/10.1021/jp202715g
[6]
Luzan, S. (2012) Materials for Hydrogen Storage and Synthesis of New Materials by Hydrogenation. Ph.D. Thesis, Umeå University, Sweden.
[7]
Luzan, S., Tsybin, Y.O. and Talyzin, A. (2011) Reaction of C60 with Hydrogen Gas: In Situ Monitoring and Pathways. The Journal of Physical Chemistry C, 115, 11484-11492. http://dx.doi.org/10.1021/jp202715g
[8]
Cataldo, F. and Iglesias-Groth, S. (2010) Fulleranes: The Hydrogenated Fullerenes. Springer, Dordrecht. http://dx.doi.org/10.1007/978-1-4020-9887-1
[9]
Hirsch, A. (2005) Fullerenes: Chemistry and Reactions. Hirsch, A. and Brettreich, M., Eds., Wiley-VCH Verlag Gmbh & Co., Weinheim.
[10]
Goldshleger, N.F. and Moravsky, A.P. (1997) Hydrides of the Fullerenes. Uspekhi Khimii, 66, 353-375. (In Russian)
[11]
Zhang, J.P, Wang, N.X., Yang, Y.X. and Yu, A.G. (2004) Hydrogenation of [60]Fullerene with Lithium in Aliphatic Amine. Carbon, 42, 667-691. http://dx.doi.org/10.1016/j.carbon.2003.12.087
[12]
Kharlamov, A., Bondarenko, M.E. and Kirillova, N.V. (2012) New Method for Synthesis of Fullerenes and Fullerene Hydrides from Benzene. Russian Journal of Applied Chemistry, 85, 244-249. http://dx.doi.org/10.1134/S1070427212020127
[13]
Kharlamov, A., Bondarenko, M.E. and Kirillova, N.V. (2013) Mass Spectrometric Research of Hydrogenated Molecules of Carbon as Products of Pyrolysis of Benzene and Pyridine Vapours. Chemical and Materials Engineering, 1, 122-131.
[14]
Kharlamov, A., Bondarenko, M.E. and Kirillova, N.V. (2013) Hydrogenated Molecules of Carbon as Products of New Pyrolysis Method of Toluene, Xylene and Ethanol. Universal Journal of Chemistry, 1, 102-112.
[15]
Kharlamov, A.I., Bondarenko, M.E. and Kirillova, N.V. (2013) New Products of a New Method for Pyrolysis of Pyridine. Russian Journal of Applied Chemistry, 86, 167-175. http://dx.doi.org/10.1134/S1070427213020079
[16]
Kharlamov, A.I., Bondarenko, M.E. and Kirillova, N.V. (2013) New Low-Temperature Method for Joint Synthesis of C60 Fullerene and New Carbon Molecules in the Form of C3-C15 and Quasi-Fullerenes C48, C42, C40. Russian Journal of Applied Chemistry, 86, 1174-1183. http://dx.doi.org/10.1134/S1070427213080053
[17]
Kharlamov, A., Kharlamova, G., Bondarenko, M. and Fomenko, V. (2013) New Method for Generation of Carbon Mo- lecules and Clusters. Open Journal of Synthesis Theory and Application, 2, 38-45. http://dx.doi.org/10.4236/ojsta.2013.21004
[18]
Kharlamov, A., Kharlamova, G., Bondarenko, M. and Fomenko, V. (2013) Joint Synthesis of Small Carbon Molecules (C3-C11), Quasi-Fullerenes (C40, C48, C52) and Their Hydrides. Chemical Engineering and Science, 1, 32-40. http://dx.doi.org/10.12691/ces-1-3-1
[19]
Kharlamova, G., Kharlamov, O.G., Bondarenko, M., Gubareni, N. and Fomenko, V. (2013) Hetero-Carbon: Heteroatomic Molecules and Nano-Structures of Carbon. In: Vaseashta, A. and Khudaverdyan, S., Eds., Advanced Sensors for Safety and Security, NATO Science for Peace and Security Series B: Physics and Biophysics, Part VII, Springer, Apeldoorn, 339-357.
[20]
Kharlamova, G., Kharlamov, O., Bondarenko, M. and Fomenko, V. (2013) Small Carbon Molecules and Quasi-Fullerenes as Products of New Method of Hydrocarbons Pyrolysis. In: Vaseashta, A. and Khudaverdyan, S., Eds., Advanced Sensors for Safety and Security, NATO Science for Peace and Security Series B: Physics and Biophysics, Part VII, Springer, Apeldoorn, 329-338.
[21]
Kulik, T.V., Barvinchenko, V.N., Palyanitsa, B.B. and Smirnova, O.V. (2007) A Desorption Mass Spectrometry Study of the Interaction of Cinnamic Acid with a Silica Surface. Russian Journal of Physical Chemistry, 81, 83-90. http://dx.doi.org/10.1134/S0036024407010165
[22]
Peera, А.А. (2004) Fullerene Hydrides and Studies toward the Syntheses of Fulvalenes. Ph.D. Thesis, Houston, Texas.
Knight, D.A., Teprovich, J.A., Summers, A., Peters, B. and Ward, P. (2013) Synthesis, Characterization, and Reversible Hydrogen Sorption Study of Sodium-Doped Fullerene. Nanotechnology, 24, Article ID: 455601. http://dx.doi.org/10.1088/0957-4484/24/45/455601
[25]
Gromovoy, T.Y., Palyanytsya, B.B., Pokrovskiy, V.A., Basiuk, E.V. and Basiuk, V.A. (2004) Interaction of Thermally Pretreated Carbon Nanomaterials with Water Vapor. Journal of Nanoscience and Nanotechnology, 4, 77-81. http://dx.doi.org/10.1166/jnn.2004.041
[26]
Stoldt, R., Maboudian, R. and Carraro, C. (2001) Vibrational Spectra of Hydrogenated Buckminsterfullerene: A Candidate for the Unidentified Infrared Emission. The Astrophysical Journal Letters, 548, 225-228. http://dx.doi.org/10.1086/319112
[27]
Dorozhko, P.A., Lobach, A.S., Popov, A.A., Senyavin, V.M. and Korobov, M.V. (2001) Sublimation of Hydrofullerenes C60H36 and C60H18. Chemical Physics Letters, 336, 39-46. http://dx.doi.org/10.1016/S0009-2614(01)00103-8
[28]
Gakh, A.A. and Romanovich, A.Y. (2003) Thermodynamic Rearrangement Synthesis and NMR Structures of C1, C3, and T Isomers of C60H36. Journal of the Chemical Society, 125, 7902-7906. http://dx.doi.org/10.1021/ja035332t
[29]
Kharlamov, A., Bondarenko, M., Kharlamova, G., Gubareni, N. and Fomenko, V. (2013) A New Method of Synthesis Carbon with Onion-Like Structure with High (10-13%) Content of Nitrogen from Pyridine. Universal Journal of Materials Science, 1, 78-86.
[30]
Kharlamov, A.I., Kharlamov, G.A. and Bondarenko, M.E. (2013) Preparation of Onion-Like Carbon with High Nitrogen Content (~15%) from Pyridine. Russian Journal of Applied Chemistry, 86, 1493-1503. http://dx.doi.org/10.1134/S1070427213100054
