Structure characteristics and association behavior of coal and petroleum C7-asphaltenes

DU Jun-tao; ZHANG Da-kui; ZHANG Min-xin; JIA Hui-na; NIE Yi; SUN Yi-kai; DENG Wen-an; LI Chuan

Volume 48 Issue 6

Jun. 2020

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Article Navigation > Journal of Fuel Chemistry and Technology > 2020 > 48(6): 674-682

DU Jun-tao, ZHANG Da-kui, ZHANG Min-xin, JIA Hui-na, NIE Yi, SUN Yi-kai, DENG Wen-an, LI Chuan. Structure characteristics and association behavior of coal and petroleum C7-asphaltenes[J]. Journal of Fuel Chemistry and Technology, 2020, 48(6): 674-682.

Citation:

DU Jun-tao, ZHANG Da-kui, ZHANG Min-xin, JIA Hui-na, NIE Yi, SUN Yi-kai, DENG Wen-an, LI Chuan. Structure characteristics and association behavior of coal and petroleum C7-asphaltenes[J]. Journal of Fuel Chemistry and Technology, 2020, 48(6): 674-682.

Citation:

DU Jun-tao, ZHANG Da-kui, ZHANG Min-xin, JIA Hui-na, NIE Yi, SUN Yi-kai, DENG Wen-an, LI Chuan. Structure characteristics and association behavior of coal and petroleum C7-asphaltenes[J]. Journal of Fuel Chemistry and Technology, 2020, 48(6): 674-682.

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Structure characteristics and association behavior of coal and petroleum C7-asphaltenes

1.
Department of Green Technology Research, Zhengzhou Institute of Emerging Industrial Technology(Institute of Process Engineering, Chinese Academy of Sciences, Zhengzhou), Zhengzhou 450000, China
2.
Ansteel Chemical Technology Co., Ltd., Anshan 114000, China
3.
State Key Laboratory of Heavy Oil, China University of Petroleum(East China), Qingdao 266580, China

Funds:

the National Natural Science Foundation of China 21908206

More Information

Corresponding author: NIE Yi.E-mail: ynie@ipe.ac.cn
Received Date: 2020-06-01
Rev Recd Date: 2020-06-05

Available Online: 2021-01-23

Publish Date: 2020-06-10

Abstract

Abstract

The structural characteristics and differences of coal tar and petroleum C7-asphaltenes were studied, such as chemical composition, functional groups and molecular structure, using nuclear magnetic resonance (NMR), small angle X-ray scattering (SAXS), X-ray photoelectron spectroscopy (XPS), improved B-L method and other methods. Furthermore, the association behavior and aggregation size of two different types of asphaltenes as well as the hydrogen bonds and acidic-basic interaction were analyzed by asphaltenes solubility parameters in polar solvents. The experiment results showed that the coal tar asphaltenes (CT-asp) was mainly composed of less aromatic rings with more short alkyl branched chains and possessed a high aromaticity degree. The higher content oxygen heteroatoms of CT-asp were mostly presented as aromatic ether bonds and phenolic hydroxyl groups. The aromatic nucleus size and the average relative molecular weight of petroleum asphaltenes (M-asp) were larger than that of CT-asp. The M-asp consisted primarily of more aromatic rings with more long alkyl branched chains and possessed a low aromaticity degree. The association and aggregation degree between CT-asp and M-asp was associated with the amount of substance ratio (n_CT-asp/n_M-asp) and their molecular structure characteristics. The association force of two types mainly was the hydrogen bonds and the acidic-basic interaction from heteroatomic functional groups.
- coal tar,
- petroleum,
- C7-asphaltene,
- molecular structure,
- association behavior

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References(32)

References

[1]	KAN T, SUN X, WANG H, LI C, MUHAMMAD U. Production of gasoline and diesel from coal tar via its catalytic hydrogenation in serial fixed beds[J]. Energy Fuels, 2012, 26(6):3604-3611. doi: 10.1021/ef3004398
[2]	张倩玉, 许志明, 赵锁奇.低温煤焦油常渣C5沥青质的分离与表征[J].燃料化学学报, 2016, 44(11):1318-1325. doi: 10.3969/j.issn.0253-2409.2016.11.006 ZHANG Qian-yu, XU Zhi-ming, ZHAO Suo-qi. Separation and characterization of C5-asphaltene from low temperature coal tar[J]. J Fuel Chem Technol, 2016, 44(11):1318-1325. doi: 10.3969/j.issn.0253-2409.2016.11.006
[3]	ANGELES M J, LEYVA C, ANCHEYTA J, RAMÍREZ S. A review of experimental procedures for heavy oil hydrocracking with dispersed catalyst[J]. Catal Today, 2014, 220-222, 274-294. https://www.sciencedirect.com/science/article/abs/pii/S0920586113003908
[4]	LI C, DU J, YANG T, DENG W. Exploratory investigation on the slurry-phase hydrocracking reaction behavior of coal tar and petroleum-based heavy oil mixed raw material[J]. Energy Fuels, 2019, 33(9):8471-8482. doi: 10.1021/acs.energyfuels.9b02031
[5]	盛强, 王刚, 金楠, 张淇源, 高成地, 高金森.石油沥青质的微观结构分析和轻质化[J].化工进展, 2019, 38(3):1147-1159. http://d.old.wanfangdata.com.cn/Periodical/hgjz201903001 SHENG Qiang, WANG Gang, JIN Nan, ZHANG Qi-yuan, GAO Cheng-di, GAO Jin-sen. Petroleum asphaltene micro-structure analysis and lightening[J]. Chem Ind Eng Prog, 2019, 38(3):1147-1159. http://d.old.wanfangdata.com.cn/Periodical/hgjz201903001
[6]	张文, 龙军, 任强, 蔡新恒.沥青质分子聚集行为研究进展[J].化工进展, 2019, 38(5):2158-2163. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=hgjz201905011 ZHANG Wen, LONG Jun, REN Qiang, CAI Xin-heng. Research progress on aggregation behavior of asphaltene[J]. Chem Ind Eng Prog, 2019, 38(5):2158-2163. http://www.wanfangdata.com.cn/details/detail.do?_type=perio&id=hgjz201905011
[7]	隆建, 沈本贤, 赵基钢, 凌昊, 卢俊财.减压渣油掺炼煤焦油改善常压溶剂脱沥青过程的机理[J].石油学报(石油加工), 2012, 28(1):69-75. doi: 10.3969/j.issn.1001-8719.2012.01.013 LONG Jian, SHEN Ben-xian, ZHAO Ji-gang, LING Hao, LU Jun-cai. Mechanism of improving atmospheric solvent deasphalting process by vacuum residue blending with coal tar[J]. Acta Pet Sin(Pet Process Sect):2012, 28(1):69-75. doi: 10.3969/j.issn.1001-8719.2012.01.013
[8]	孟兆会, 杨圣斌, 杨涛, 郭蓉.减压渣油掺炼煤焦油相容性及加氢处理研究[J].石油炼制与化工, 2014, 45(5):25-28. doi: 10.3969/j.issn.1005-2399.2014.05.005 MENG Zhao-hui, YANG Sheng-bin, YANG Tao, GUO Rong. Study on stability of vacuum residue blending coal tar and hydrocracking of mixture[J]. Chin Pet Process Petrochem Technol, 2014, 45(5):25-28. doi: 10.3969/j.issn.1005-2399.2014.05.005
[9]	胡建宏, 程相林, 李国宁, 武建军, 汲伟, 王永刚, 王柏川.煤沥青可溶组分在甲苯中缔合行为的研究[J].燃料化学学报, 2014, 42(7):774-778. http://manu60.magtech.com.cn/rlhxxb/CN/abstract/abstract18443.shtml HU Jian-hong, CHENG Xiang-lin, LI Guo-ning, WU Jian-jun, JI Wei, WANG Yong-gang, WANG Bai-chuan. Association behavior of coal tar pitch soluble components in toluene[J]. J Fuel Chem Technol, 2014, 42(7):774-778. http://manu60.magtech.com.cn/rlhxxb/CN/abstract/abstract18443.shtml
[10]	YUDIN I K, NIKOLAENKO G L, GORODETSKII E E, KOSOV V I, MELIKYAN V R, MARKHASHOV E L, FROT D, BRIOLANT Y. Mechanisms of asphaltene aggregation in toluene-heptane mixtures[J]. J Pet Sci Eng, 1998, 20(3/4):297-301. https://www.sciencedirect.com/science/article/pii/S0920410598000333
[11]	HAJI-AKBARI N, TEERAPHAPKUL P, FOGLER H S. Effect of asphaltene concentration on the aggregation and precipitation tendency of asphaltenes[J]. Energy Fuels, 2014, 28(2):909-919. doi: 10.1021/ef4021125
[12]	ANISIMOV M A, GANEEVA Y M, GORODETSKII E E, DESHABO V A, KOSOV V I, KURYAKOV V N, YUDIN D I, YUDIN I K. Effects of resins on aggregation and stability of asphaltenes[J]. Energy Fuels, 2014, 28(10):6200-6209. doi: 10.1021/ef501145a
[13]	KRAIWATTANAWONG K, FOGLER H S, GHARFEH S G, SINGH P, THOMASON W H, CHAVADEJ S. Effect of asphaltene dispersants on aggregate size distribution and growth[J]. Energy Fuels, 2009, 23(3):1575-1582. doi: 10.1021/ef800706c
[14]	GRAY M R, TYKWINSKI R R, STRYKER J M, TAN X. Supramolecular assembly model for aggregation of petroleum asphaltenes[J]. Energy Fuels, 2011, 25(7):3125-3134. doi: 10.1021/ef200654p
[15]	GABRIENKO A A, MARTYANOV O N, KAZARIAN S G. Effect of temperature and composition on the stability of crude oil blends studied with chemical imaging[J]. Energy Fuels, 2015, 29(11):7114-7123. doi: 10.1021/acs.energyfuels.5b01880
[16]	AGRAWALA M, YARRANTON H W. An asphaltene association model analogous to linear polymerization[J]. Ind Eng Chem Res, 2001, 40(21):4664-4672. doi: 10.1021/ie0103963
[17]	RAKOTONDRADANY F, FENNIRI H, RAHIMI P, GAWRYS K L, KILPATRICK P K, GRAY M R. Hexabenzocoronene model compounds for asphaltene fractions:Synthesis & characterization[J]. Energy Fuels, 2006, 20(6):2439-2447. doi: 10.1021/ef060130e
[18]	LI P, ZONG Z, LI Z, WANG Y, LIU F, WEI X. Characterization of basic heteroatom-containing organic compounds in liquefaction residue from Shenmu-Fugu subbituminous coal by positive-ion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry[J]. Fuel Process Technol, 2015, 132:91-98. doi: 10.1016/j.fuproc.2014.12.026
[19]	DU J, DENG W, LI C, ZHANG Z, YANG T, GUO R. Reactivity and structure changes of coal tar asphaltene during slurry-phase hydrocracking[J]. Energy Fuels, 2017, 31(2):1858-1865. doi: 10.1021/acs.energyfuels.6b02992
[20]	XIONG G, LI Y, JIN L, HU H. In situ FT-IR spectroscopic studies on thermal decomposition of the weak covalent bonds of brown coal[J]. J Anal Appl Pyroysisl, 2015, 115:262-267. doi: 10.1016/j.jaap.2015.08.002
[21]	FERGOUG T, BOUHADDA Y. Determination of Hassi Messaoud asphaltene aromatic structure from 1H & 13C NMR analysis[J]. Fuel, 2014, 115:521-526. doi: 10.1016/j.fuel.2013.07.055
[22]	DUTTA MAJUMDAR R, BAKE K D, RATNA Y, POMERANTZ A E, MULLINS O C, GERKEN M, HAZENDONK P. Single-core PAHs in petroleum-and coal-derived asphaltenes:Size and distribution from solid-state NMR spectroscopy and optical absorption measurements[J]. Energy Fuels, 2016, 30(9):6892-6906. doi: 10.1021/acs.energyfuels.5b02815
[23]	ALHUMAIDAN F S, HAUSER A, RANA M S, LABABIDI H M S, BEHBEHANI M. Changes in asphaltene structure during thermal cracking of residual oils:XRD study[J]. Fuel, 2015, 150:558-564. doi: 10.1016/j.fuel.2015.02.076
[24]	SCHNEIDER M H, ANDREWS A B, MITRA-KIRTLEY S, MULLINS O C. Asphaltene molecular size by fluorescence correlation spectroscopy[J]. Energy Fuels, 2007, 21(5):2875-2882. doi: 10.1021/ef700216r
[25]	JIN N, WANG G, HAN S, MENG Y, XU C, GAO J. Hydroconversion behavior of asphaltenes under liquid-phase hydrogenation conditions[J]. Energy Fuels, 2016, 30(4):2594-2603. doi: 10.1021/acs.energyfuels.5b02765
[26]	SUN Z, LI D, MA H, TIAN P, LI X, LI W, ZHU Y. Characterization of asphaltene isolated from low-temperature coal tar[J]. Fuel Process Technol, 2015, 138:413-418. doi: 10.1016/j.fuproc.2015.05.008
[27]	XIA W, YANG J. Reverse flotation of Taixi oxidized coal[J]. Energy Fuels, 2013, 27(12):7324-7329. doi: 10.1021/ef4017224
[28]	EYSSAUTIER J, LEVITZ P, ESPINAT D, JESTIN J, GUMMEL J, GRILLO I, BARRE L. Insight into asphaltene nanoaggregate structure inferred by small angle neutron and X-ray scattering[J]. J Phys Chem B, 2011, 115(21):6827-6837. doi: 10.1021/jp111468d
[29]	张庆, 邓文安, 李传, 吴乐乐.稠油沥青质的基本化学组成结构与缔合性研究[J].石油炼制与化工, 2014, 45(6):20-25. doi: 10.3969/j.issn.1005-2399.2014.06.007 ZHANG Qing, DENG WEN-an, LI Chuan, WU Le-le. Study on basic chemical structure and association of asphaltene in heavy oil[J]. Chin Pet Process Petrochem Technol, 2014, 45(6):20-25. doi: 10.3969/j.issn.1005-2399.2014.06.007
[30]	JUYAL P, MERINO-GARCIA D, ANDERSEN S I. Effect on molecular interactions of chemical alteration of petroleum asphaltenes[J]. Energy Fuels, 2005, 19(4):1272-1281. doi: 10.1021/ef050012b
[31]	LIU X, HIRAJIMA T, NONAKA M, SASAKI K. Investigation of the changes in hydrogen bonds during low-temperature pyrolysis of lignite by diffuse reflectance FT-IR combined with forms of water[J]. Ind Eng Chem Res, 2015, 54(36):8971-8978. doi: 10.1021/acs.iecr.5b02474
[32]	张龙力, 王春岚, 赵元生, 杨国华, 杨朝合.塔河常压渣油沥青质含硫官能团形态与其性质的关系研究[J].燃料化学学报, 2012, 40(9):1081-1085. doi: 10.3969/j.issn.0253-2409.2012.09.009 ZHANG Long-li, WANG Chun-lan, ZHAO Yuan-sheng, YANG Guo-hua, YANG Chao-he. Study on the relationship between sulfur functionalities and the characteristics of THAR asphaltene[J]. J Fuel Chem Technol, 2012, 40(9):1081-1085. doi: 10.3969/j.issn.0253-2409.2012.09.009