Separation and analysis of six fractions in low temperature coal tar by column chromatography

doi:10.1016/j.cjche.2022.12.002

Chinese Journal of Chemical Engineering ›› 2023, Vol. 58 ›› Issue (6): 256-265.DOI: 10.1016/j.cjche.2022.12.002

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Separation and analysis of six fractions in low temperature coal tar by column chromatography

Shuangtai Liu¹, Lei He¹, Qiuxiang Yao^1,2, Xi Li¹, Linyang Wang¹, Jing Wang², Ming Sun¹, Xiaoxun Ma¹

1. School of Chemical Engineering, Northwest University, International Science & Technology Cooperation Base of MOST for Clean Utilization of Hydrocarbon Resources, Chemical Engineering Research Center of the Ministry of Education for Advanced Use Technology of Shanbei Energy, Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern, Xi'an 710069, China;
2. School of Electronic Information, Xijing University, Xi'an Key Laboratory of Advanced Photo-electronics Materials and Energy Conversion Device, Xi'an 710123, China

Received:2022-10-07 Revised:2022-12-05 Online:2023-08-31 Published:2023-06-28
Contact: Xiaoxun Ma,E-mail:maxym@nwu.edu.cn
Supported by:
This work was financed by the project supported by the National Natural Science Foundation of China (22078266, 21908180, 22178289, 22278338), the Key Research and Development Program of Shaanxi (2020ZDLGY11-02, 2021GY-136) and the Special Fund for High-level Scholars of China (XJ21B10).

Separation and analysis of six fractions in low temperature coal tar by column chromatography

Shuangtai Liu¹, Lei He¹, Qiuxiang Yao^1,2, Xi Li¹, Linyang Wang¹, Jing Wang², Ming Sun¹, Xiaoxun Ma¹

1. School of Chemical Engineering, Northwest University, International Science & Technology Cooperation Base of MOST for Clean Utilization of Hydrocarbon Resources, Chemical Engineering Research Center of the Ministry of Education for Advanced Use Technology of Shanbei Energy, Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern, Xi'an 710069, China;
2. School of Electronic Information, Xijing University, Xi'an Key Laboratory of Advanced Photo-electronics Materials and Energy Conversion Device, Xi'an 710123, China

通讯作者: Xiaoxun Ma,E-mail:maxym@nwu.edu.cn
基金资助:
This work was financed by the project supported by the National Natural Science Foundation of China (22078266, 21908180, 22178289, 22278338), the Key Research and Development Program of Shaanxi (2020ZDLGY11-02, 2021GY-136) and the Special Fund for High-level Scholars of China (XJ21B10).

Abstract

Abstract: The low temperature coal tar (CT) is taken as the raw material, and the extraction and column chromatography are used for detailed and accurate characterization in this paper. The n-heptane soluble fraction (CT-HS) and insoluble fraction (CT-HI) were obtained by n-heptane Soxhlet extraction. The extraction rate of CT-HS reached 92.79% (mass), which indicated that there are few heavy compounds in it. Further, different solvents (methylbenzene, benzene, ethyl acetate, methylbenzene-ethanol) were used to elute CT-HS by chromatographic column to obtain five fractions (saturates, aromatics, heteroatoms, phenolics and resins, named CT-SA, CT-AR, CT-HE, CT-PH, CT-RE, respectively). The yields of CT-SA, CT-AR, CT-HE, CT-PH, CT-RE are 42.12%, 10.43%, 2.19%, 9.50% and 6.63% (mass), respectively. Gas chromatography-mass spectrometry analysis of eluting components show that alkanes are the main components in CT, followed by polycyclic aromatics, and the corresponding fractions are CT-SA and CT-AR, respectively. The relative content of aliphatics in CT-SA is 76.93%, and the relative content of aromatics in CT-AR is 75.05%. This separation technology effectively separates and enriches different components in CT, and the activation energy required for the pyrolysis process of a single eluting fraction is lower than that of CT, which is expected to provide an important reference for the separation, analysis and conversion of complex oil products such as coal-oil co-processing products, coal tar and other complex heavy carbon oil products.

Key words: Low temperature coal tar, Extractive separation, Column chromatography isolation, Chromatography/mass spectrometry

摘要： The low temperature coal tar (CT) is taken as the raw material, and the extraction and column chromatography are used for detailed and accurate characterization in this paper. The n-heptane soluble fraction (CT-HS) and insoluble fraction (CT-HI) were obtained by n-heptane Soxhlet extraction. The extraction rate of CT-HS reached 92.79% (mass), which indicated that there are few heavy compounds in it. Further, different solvents (methylbenzene, benzene, ethyl acetate, methylbenzene-ethanol) were used to elute CT-HS by chromatographic column to obtain five fractions (saturates, aromatics, heteroatoms, phenolics and resins, named CT-SA, CT-AR, CT-HE, CT-PH, CT-RE, respectively). The yields of CT-SA, CT-AR, CT-HE, CT-PH, CT-RE are 42.12%, 10.43%, 2.19%, 9.50% and 6.63% (mass), respectively. Gas chromatography-mass spectrometry analysis of eluting components show that alkanes are the main components in CT, followed by polycyclic aromatics, and the corresponding fractions are CT-SA and CT-AR, respectively. The relative content of aliphatics in CT-SA is 76.93%, and the relative content of aromatics in CT-AR is 75.05%. This separation technology effectively separates and enriches different components in CT, and the activation energy required for the pyrolysis process of a single eluting fraction is lower than that of CT, which is expected to provide an important reference for the separation, analysis and conversion of complex oil products such as coal-oil co-processing products, coal tar and other complex heavy carbon oil products.

关键词: Low temperature coal tar, Extractive separation, Column chromatography isolation, Chromatography/mass spectrometry

Shuangtai Liu, Lei He, Qiuxiang Yao, Xi Li, Linyang Wang, Jing Wang, Ming Sun, Xiaoxun Ma. Separation and analysis of six fractions in low temperature coal tar by column chromatography[J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 256-265.

References

[1] X.X. Ma, Y.K. Zhao, M. Sun, Y.X. Yao, Technical on utilization technology of high temperature coal tar, Coal Convers. 43 (4) (2020) 1-11. (in Chinese)
[2] M. Sun, J. Chen, X.M. Dai, X.L. Zhao, K. Liu, X.X. Ma, Controlled separation of low temperature coal tar based on solvent extraction-column chromatography, Fuel Process. Technol. 136 (2015) 41-49.
[3] L. He, Q.X. Yao, M. Sun, X.X. Ma, Progress in preparation and catalysis of two-dimensional (2D) and three-dimensional (3D) zeolites, Acta Chimica Sin. 80 (2) (2022) 180-198.
[4] X. Gu, Status and prospect of separation methods and composition characteristics of coal tar, Clean Coal Technol. 24 (4) (2018) 1-6. (in Chinese)
[5] Z.H. Sun, W.H. Zhang, Chemical composition and structure characterization of distillation residues of middle-temperature coal tar, Chin. J. Chem. Eng. 25 (6) (2017) 815-820.
[6] X.F. Mao, J.F. Li, J.L. Zhong, Q. Shi, B.F. Yan, M. Liu, Composition and structure molecular characterizations of medium and low temperature coal tar, J. China Coal Soc. 44 (3) (2019) 957-963. (in Chinese)
[7] Y.H. Zhu, Y.T. Guo, X. Zhang, F. Tian, C. Luo, C.P. Du, T. H. Yang, M.S. Chen, Z.H. Sun, D. Li, Exploration of coal tar asphaltene molecules based on high resolution mass spectrometry and advanced extraction separation method, Fuel Process. Technol. 233 (2022) 107309.
[8] J.F. Yang, Q.X. Yao, Y.Q. Liu, L.Y. Wang, D. Ma, L. He, J.W. Gao, Y.J. Zhang, L. Ma, M. Sun, X.X. Ma, Mechanism of catalytic conversion of kerosene co-refining heavy oil to BTEXN by Py-GC/MS based on “point-line-surface-body” step by step research strategy, Fuel 332 (2023) 125979.
[9] M. Sun, J. Chen, X.M. Dai, X.X. Ma, X.L. Zhao, K. Liu, Vacuum distillates and GC-MS analysis of low temperature coal tar from Northern Shaanxi, Coal Convers. 38 (1) (2015) 58-63. (in Chinese)
[10] C.Y. Liu, S. Zhao, Q.Q. Gai, L.G. Ma, Y. Bai, R. Wang, X.F. Guo, Y.H. Long, Characterization of C₇-asphaltenes from different coal tar, Coal Sci. Technol. 48 (S1) (2020) 194-198. (in Chinese)
[11] Z.H. Ma, X.Y. Wei, G.H. Liu, Z.Q. Liu, F.J. Liu, Z.M. Zong, Insight into the compositions of the soluble/insolube portions from the acid/base extraction of five fractions distilled from a high temperature coal tar, Energy Fuels 33 (10) (2019) 10099-10107.
[12] Z.J. Wang, The chemistry and physics of petroleum asphaltenes part III. The study methods of chemical structure of asphaltenes, Asphalt 10 (1996) 39-50. (in Chinese)
[13] J. Ancheyta, G. Centeno, F. Trejo, G. Marroquín, Changes in asphaltene properties during hydrotreating of heavy crudes, Energy Fuels 17 (5) (2003) 1233-1238.
[14] S.E. Moschopedis, S. Parkash, J.G. Speight, Thermal decomposition of asphaltenes, Fuel 57 (7) (1978) 431-434.
[15] Test method for separation of asphalt into four fractions, Petrochemical Industry Standard of the People's Republic of China, NB/SH/T0509-2010.
[16] M. Sun, X.X. Ma, B. Lv, X.M. Dai, Y. Yao, Y.Y. Liu, M. He, X.L. Zhao, Gradient separation of ≥300 ℃ distillate from low-temperature coal tar based on formaldehyde reactions, Fuel 160 (2015) 16-23.
[17] M.R. Gray, Consistency of asphaltene chemical structures with pyrolysis and coking behavior, Energy Fuels 17 (6) (2003) 1566-1569.
[18] M. Sun, X.X. Ma, Q.X. Yao, R.C. Wang, Y.X. Ma, G. Feng, J.X. Shang, L. Xu, Y.H. Yang, GC-MS and TG-FTIR study of petroleum ether extract and residue from low temperature coal tar, Energy Fuels 25 (3) (2011) 1140-1145.
[19] Y.L. Li, H.A. Luo, Q.H. Ai, K.Y. You, F. Zhao, W.L. Xiao, Efficient separation of phenols from coal tar with aqueous solution of amines by liquid-liquid extraction, Chin. J. Chem. Eng. 35 (2021) 180-188.
[20] Z.H. Ma, X.Y. Wei, H.L. Gao, G.H. Liu, Z.Q. Liu, F.J. Liu, Z.M. Zong, Selective and effective separation of five condensed arenes from a high-temperature coal tar by extraction combined with high pressure preparative chromatography, J. Chromatogr. A 1603 (2019) 160-164.
[21] M. Sun, D. Zhang, Q.X. Yao, Y.Q. Liu, X.P. Su, C.Q. Jia, Q.Q. Hao, X.X. Ma, Separation and composition analysis of GC/MS analyzable and unanalyzable parts from coal tar, Energy Fuels 32 (7) (2018) 7404-7411.
[22] Q.X. Yao, Y.B. Li, X. Tang, J.W. Gao, R.C. Wang, Y.J. Zhang, M. Sun, X.X. Ma, Separation of petroleum ether extracted residue of low temperature coal tar by chromatography column and structural feature of fractions by TG-FTIR and PY-GC/MS, Fuel 245 (2019) 122-130.
[23] M. Sun, Y.B. Li, S. Sha, J.W. Gao, R.C. Wang, Y.J. Zhang, Q.Q. Hao, H.Y. Chen, Q.X. Yao, X.X. Ma, The composition and structure of n-hexane insoluble-hot benzene soluble fraction and hot benzene insoluble fraction from low temperature coal tar, Fuel 262 (2020) 116511.
[24] Q.X. Yao, M.M. Ma, L. Ma, Y.Q. Liu, H.Y Chen, L.Y. Jiao, Q.Q. Hao, M. Sun, X.X. Ma, The structural and pyrolysis characteristics of vitrinite and inertinite from Shendong coal and the gasification performance of chars, J. Anal. Appl. Pyrol. 164 (2022) 105519.
[25] A.W. Coats, J.P. Redfern, Kinetic parameters from thermogravimetric data, Nature 201(4914) (1964) 68-69.
[26] Y.K. Lin, Q.S. Li, X.F. Li, K. Ji, H.P. Zhang, Y.M. Yu, Y.H. Song, Y. Fu, L.Y. Sun, Pyrolysates distribution and kinetics of Shenmu long flame coal, Energy Convers. Manag. 86 (2014) 428-434.
[27] S. Ali, S.A. Hussain, M.Z.M. Tohir, A.A. Nuruddin, Investigation of kinetic decomposition characteristics of Malaysian wood species using Coats and Redfern (CR) method, Mater. Today Proc. 42 (2021) 178-185.
[28] E.M.A. Edreis, G. Luo, A. Li, C. Xu, H. Yao, Synergistic effects and kinetics thermal behaviour of petroleum coke/biomass blends during H₂O co-gasification, Energy Convers. Manag. 79 (2014) 355-366.
[29] R.S. Zhou, R. Cao, Y.Q. Liu, D. Ma, Q.X. Yao, J. Wang, M. Sun, X.X. Ma, Study on the characteristics and mechanism of fast co-pyrolysis of coal tar asphaltene and biomass, J. Anal. Appl. Pyrolysis 161 (2022) 105409.
[30] Q.L. Yang, Q.X. Yao, D. Ma, Y.Q. Liu, L. He, R.S. Zhou, M. Sun, X.X. Ma, Investigation of the (catalytic) co-pyrolysis of Shendong coal and coal tar based on rapid pyrolysis and ANN modelling, J. Anal. Appl. Pyrolysis 163 (2022) 105486.
[31] M. Sun, L.Y. Wang, J.J. Zhog, Q.X. Yao, H.Y. Chen, L.Y. Jiao, Q.Q. Hao, X.X. Ma, Chemical modification with aldehydes on the reduction of toxic PAHs derived from low temperature coal tar pitch, J. Anal. Appl. Pyrolysis 148 (2020) 104822.
[32] T. Xu, X.M. Huang, Study on combustion mechanism of asphalt binder by using TG-FTIR technique, Fuel 89 (9) (2010) 2185-2190.
[33] V. Calemma, P. Iwanski, M. Nali, R. Scotti, L. Montanari, Structural characterization of asphaltenes of different origins, Energy Fuels 9 (2) (1995) 225-230.
[34] A. Arenillas, C. Pevida, F. Rubiera, R. García, J.J. Pis, Characterisation of model compounds and a synthetic coal by TG/MS/FTIR to represent the pyrolysis behaviour of coal, J. Anal. Appl. Pyrolysis 71 (2) (2004) 747-763.
[35] Y.Y. Liu, Z.Z. Song, Y.H. Yang, Y. Huang, M. Sun, X.L. Zhao, X.X. Ma, Asphalt modification with coal tar pitch component based on aldehyde crosslinkers, J. Fuel Chem. Techno. 44 (2016) 792-800. (in Chinese)
[36] Y.Q. Liu, Q.X. Yao, M. Sun, X.X. Ma, Selective preparation of light aromatic hydrocarbons from catalytic fast pyrolysis vapors of coal tar asphaltene over transition metal ion modified zeolites, Chin. J. Chem. Eng. 35 (2021) 275-287.
[37] L.Y. Wang, Q. Wang, Y.Q. Liu, Q.X. Yao, M. Sun, X.X. Ma, Catalytic conversion of asphaltenes to BTXN using metal-loaded modified HZSM-5, Chin. J. Chem. Eng. 49 (2022) 253-264.

Separation and analysis of six fractions in low temperature coal tar by column chromatography

Separation and analysis of six fractions in low temperature coal tar by column chromatography

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