Abstract
This work is concerned with the conversion of anthracene into products with potential applications in carbon technology. The anthracene was obtained from industrial anthracene by crystallization in raw pyridine and was subjected to thermal polycondensation under pressure with various time exposures at the final temperature at 420 °C. The proposed thermal treatment induces polymerization/polycondensation reactions, and the extent of conversion was monitored from the carbon residue by thermogravimetric analysis, heptane and toluene insolubles and Raman spectroscopy. The ability of mesophase formation from obtained polycondensates was also studied. Besides thermogravimetric analysis and Raman spectroscopy, the optical microscopy was also used to determine the presence of optically anisotropic texture. The thermal polycondensation under pressure and time exposure of 48 and 72 h at 420 °C is suggested to be the most promising method for preparing the mesophase pitches of good optical texture. The results indicate that thermal polycondensation of anthracene obtained from industrial anthracene oil could be suitable process for the conversion of anthracene into carbon precursors with potential industrial utilization.
Similar content being viewed by others
References
Rao PS. Anthracene, reference module in biomedical sciences: encyclopedia of toxicology. Amsterdam: Elsevier; 2014. p. 260–1.
Berrueco C, et al. Characterisation and feasibility as carbon fibre precursors of isotropic pitches derived from anthracene oil. Fuel. 2012;101:9–15.
Diez N, et al. Optimising of melt-spinning of anthracene oil-based pitch for isotropic carbon fibre preparation. Fuel Process Technol. 2012;93(1):99–104.
Zhong L, Zhang Y, Ji Y, Norris P, Pan W. Synthesis of activated carbon from coal pitch for mercury removal in coal-fired power plants. J Therm Anal Calorim. 2015;. doi:10.1007/s10973-015-4966-5.
Fernandez AL, Granda M, Bermejo J, Menendez R. Air-blowing of anthracene oil for carbon precursors. Carbon. 2000;38(9):1315–22.
Fernandez AL, Granda M, Bermejo J, Menendez R, Bernad P. Carbon precursors from anthracene oil. Insight into the reactions of anthracene oil with sulfur. Energy Fuel. 1998;12(5):949–57.
** ML, Cheng JL, Wang LX, ** SL, Zhang R. Rheological properties of mesophase pitch investigated by the Giseeler fluidity method. N Carbon Mater. 2015;30(2):176–80.
Li P, et al. Preparation of pitch-based general purpose carbon fibers from catalytic slurry oil. Fuel Process Technol. 2015;140:231–5.
Min G, Zengmin S, Weidong C, Hui L. Anisotropy of mesophase pitch-derived carbon foams. Carbon. 2007;45:141–5.
Mochida I, Korai Y, Ku CH, Watanabe F, Sakai Y. Chemistry of synthesis, structure, preparation and application of aromatic-derived mesophase pitch. Carbon. 2000;38:305–28.
Dias JM, et al. Waste materials for activated carbon preparation and its use in aqueous-phase treatment: a review. J Environ Manag. 2007;85:833–46.
Alvarez P, et al. An insight into the polymerization of anthracene oil to produce pitch using nuclear magnetic resonance. Fuel. 2011;92:421–7.
Bermejo J, et al. A comparative study of the composition of anthracene oil polymerized by different treatments. Fuel. 2001;80:2155–62.
Golounin AV, Marakushina EN, Khramenko SA. Polycondensation of polyaromatic hydrocarbons. Coke Chem. 2009;52(11):501–3.
Mochida I, et al. Preparation of mesophase pitch from aromatic hydrocarbons by the aid of HF/BF3. Carbon. 1990;28(2–3):311–9.
Fathollahi B, Jones B, Chau PC, White JL. Injection and stabilization of mesophase pitch in the fabrication of carbon–carbon composites. Part III: Mesophase stabilization at low temperatures and elevated oxidation pressures. Carbon. 2005;43(1):143–51.
Alvarez P, et al. A unified process for preparing mesophase and isotropic material from anthracene oil based pitch. Fuel Process Technol. 2011;92:421–7.
Oh S, Yoon SH, Dong G, Park YD. Effects of pressurized pretreatment on the preparation of mesophase pitch. Carbon. 1991;29(7):1009–14.
Montes-Moran MA, et al. Mesophase from a coal tar pitch: Raman spectroscopy study. Fuel Process Technol. 2002;77–78:207–12.
Hirose H, et al. Raman study of the effect of intense laser irradiation on graphitized mesophase spherules. Solid State Commun. 2011;101:225–30.
Shinohara H, Yamakita Y, Ohno K. Raman spectra of polycyclic aromatic hydrocarbons. Comparison of calculated Raman intensity distributions with observed spectra for naphthalene, anthracene, pyrene and perylene. J Mol Struct. 1998;442:221–34.
Maddams WF, Royaud IA. The characterization of polycyclic aromatic hydrocarbons by Raman spectroscopy. Spectrochim Acta Part A Mol Spectrosc. 1990;46(2):309–14.
Chakraborty D, Ambashta R, Manogaran S. Force-field and assignment of the vibrational-spectrum of anthracene—theoretical prediction. J Phys Chem. 1996;100(33):13963–70.
Zhang B, et al. Transformation of Lewis acid during the carbonization and graphitization of mesophase pitches. J Anal Appl Pyrolysis. 2013;104:433–40.
Acknowledgements
The article has been done in connection with Project Institute of Clean Technologies for Mining and Utilization of Raw Materials for Energy Use—Sustainability Program. Identification code: LO1406—Project is supported by National Programme for Sustainability I (2013–2020), financed by the means of state budget of the Czech Republic. And it also has been done in connection with Project No. LO1203 “Regional Materials Science and Technology Centre—Feasibility Program” funded by Ministry of Education, Youth and Sports of the Czech Republic. The authors would like to thank George Laynr for linguistic correction of the text.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Valovicova, V., Plevova, E., Vaculikova, L. et al. Thermal polycondensation of anthracene for carbon precursors. J Therm Anal Calorim 124, 261–267 (2016). https://doi.org/10.1007/s10973-015-5124-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-015-5124-9