Mesophase pitch-based high performance carbon fiber production using coal extracts from mild direct coal liquefaction

Thompson, Christina; Frank, George; Edwards, Vivian; Martinelli, Michela; Vego, Asmund; Vautard, Frederic; Cakmak, Ercan; Craddock, John; Meier, Mark; Andrews, Rodney; Weisenberger, Matthew

doi:10.1016/j.carbon.2024.119212

Mesophase pitch-based high performance carbon fiber production using coal extracts from mild direct coal liquefaction

Journal Article · Fri May 03 00:00:00 EDT 2024 · Carbon

DOI:https://doi.org/10.1016/j.carbon.2024.119212· OSTI ID:2351011

^[1]; Frank, George ^[1]; ^[1]; Martinelli, Michela ^[1]; ^[1]; Vautard, Frederic ^[2]; ^[2]; ^[1]; ^[1]; Andrews, Rodney ^[1]; Weisenberger, Matthew ^[1]

University of Kentucky, Lexington, KY (United States)
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Mild direct coal liquefaction (autogenous pressure, no catalyst, no H2 gas) of Springfield coal in fluid catalytic cracking decant oil is shown to effectively produce coal extract precursors to spinnable mesophase pitch. Here this work demonstrates that the coal extract can be thermally treated to obtain mesophase pitch in a facile one-step process, bypassing the production of an intermediate isotropic pitch. Furthermore, the presence of 25 wt.% coal in the initial slurry can increase the yield to mesophase pitch nearly twofold and yield to carbon fiber by approximately 70%. The coal extract-derived mesophase pitch was melt-spun and heat treated to produce carbon fiber with graphitic texture, high modulus (>400 GPa) and tensile strength up to 943 MPa. Overall, this work demonstrates that coal can be effectively utilized to markedly amplify the mesophase pitch and carbon fiber yield from fluid catalytic cracking decant oil by relatively simple processing, while conserving utility as a precursor to high performance carbon fiber and potentially other high value graphitic products.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 2351011

Journal Information:: Carbon, Journal Name: Carbon Journal Issue: N/A Vol. 226; ISSN 0008-6223

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (55)

Carbon Fibers: Precursor Systems, Processing, Structure, and Properties Frank, Erik; Steudle, Lisa M.; Ingildeev, Denis Angewandte Chemie International Edition, Vol. 53, Issue 21 https://doi.org/10.1002/anie.201306129	journal	March 2014
Preparation of anisotropic mesophase pitch by carbonization under vacuum Park, Yang Duk; Korai, Yozo; Mochida, Isao Journal of Materials Science, Vol. 21, Issue 2 https://doi.org/10.1007/BF01145504	journal	February 1986
Optical mesophase texture and X-ray diffraction pattern of the early-stage carbonization of pitches Honda, H.; Kimura, H.; Sanada, Y. Carbon, Vol. 8, Issue 2 https://doi.org/10.1016/0008-6223(70)90112-0	journal	March 1970
Carbonization of aromatic hydrocarbons—VI Mochida, Isao; Inoue, Shin-Ichi; Maeda, Keiko Carbon, Vol. 15, Issue 1 https://doi.org/10.1016/0008-6223(77)90068-9	journal	January 1977
Mesophase formation in coal liquid solvent fractions Weinberg, Victoria A.; Yen, Teh Fu Carbon, Vol. 21, Issue 1 https://doi.org/10.1016/0008-6223(83)90154-9	journal	January 1983
The effect of composition and process variables on the spinnability of mesophase pitch Qing-Fang, Zha; Jing-Li, Shi; Yong, Ji Carbon, Vol. 30, Issue 5 https://doi.org/10.1016/0008-6223(92)90156-Q	journal	January 1992
Properties of coal tar pitch-based mesophase separated by high-temperature centrifugation No authors listed Carbon, Vol. 31, Issue 5 https://doi.org/10.1016/0008-6223(93)90023-4	journal	January 1993
Influence of QI on mesophase structure Taylor, G. H.; Pennock, G. M.; Gerald, J. D. Fitz Carbon, Vol. 31, Issue 2 https://doi.org/10.1016/0008-6223(93)90039-D	journal	January 1993
Kinetics and mechanism of carbonization of qi-free products from gas-coking coal hydrogenation-II. Carbonization of solvent fractions separated from coal hydrogenation pitches Machnikowski, Jacek Carbon, Vol. 31, Issue 2 https://doi.org/10.1016/0008-6223(93)90042-9	journal	January 1993
Carbonization and graphitization processes of pitch from coal liquid and its fractions Świetlik, U.; Jasieńko, S.; Wolski, A. Carbon, Vol. 31, Issue 3 https://doi.org/10.1016/0008-6223(93)90134-V	journal	January 1993
Carboncarbon cleavage during asphaltene formation Collins, Clair J.; Raaen, Vernon F.; Benjamin, Ben M. Fuel, Vol. 56, Issue 1 https://doi.org/10.1016/0016-2361(77)90051-5	journal	January 1977
Coal-derived asphaltenes: effect of phenol content and molecular weight on viscosity of solutions Bockrath, Bradley C.; LaCount, Robert B.; Noceti, Richard P. Fuel, Vol. 59, Issue 9 https://doi.org/10.1016/0016-2361(80)90123-4	journal	September 1980
Carbonization and liquid-crystal (mesophase) development. 16. Carbonizations of soluble and insoluble fractions of coal-extract solution Marsh, Harry; Mochida, Isao; Macefield, Ian Fuel, Vol. 59, Issue 7 https://doi.org/10.1016/0016-2361(80)90180-5	journal	July 1980
Hydrogen bonding of the acid and base fractions separated from SRC II middle distillates Young, L.; Hara, T.; Li, N. Fuel, Vol. 63, Issue 6 https://doi.org/10.1016/0016-2361(84)90073-5	journal	June 1984
Some observations respecting reaction paths in coal liquefaction Berkowitz, Norbert; Calderon, Jaime; Liron, Abraham Fuel, Vol. 67, Issue 5 https://doi.org/10.1016/0016-2361(88)90290-6	journal	May 1988
Liquefaction of coal in a petroleum fraction under mild conditions Yan, T. Y.; Espenscheid, W. F. Fuel Processing Technology, Vol. 7, Issue 2 https://doi.org/10.1016/0378-3820(83)90031-0	journal	March 1983
Structural modification of coal-tar pitch fractions during mild oxidation—relevance to carbonization behavior Machnikowski, J.; Kaczmarska, H.; Gerus-Piasecka, I. Carbon, Vol. 40, Issue 11 https://doi.org/10.1016/S0008-6223(02)00029-5	journal	September 2002
Thermal and catalytic conversion of asphaltenes Zhang, C.; Lee, C. W.; Keogh, R. A. Fuel, Vol. 80, Issue 8 https://doi.org/10.1016/S0016-2361(00)00178-2	journal	June 2001
Size-exclusion chromatography of large molecules from coal liquids, petroleum residues, soots, biomass tars and humic substances Herod, Alan A.; Zhuo, Yuqun; Kandiyoti, Rafael Journal of Biochemical and Biophysical Methods, Vol. 56, Issue 1-3 https://doi.org/10.1016/S0165-022X(03)00070-8	journal	June 2003
Mesophase development in petroleum and coal-tar pitches and their blends Mora, E.; Santamarı́a, R.; Blanco, C. Journal of Analytical and Applied Pyrolysis, Vol. 68-69 https://doi.org/10.1016/S0165-2370(03)00034-2	journal	August 2003
Hydrogen-transfer ability of extrographic fractions of coal-tar pitch Machnikowski, J.; Kaczmarska, H.; Leszczyńska, A. Fuel Processing Technology, Vol. 69, Issue 2 https://doi.org/10.1016/S0378-3820(00)00139-9	journal	February 2001
Polymerization kinetics and control of the components of a mesophase pitch Liang, Zheng-wu; Lu, Yong-gen; Sun, Zhu-lin New Carbon Materials, Vol. 35, Issue 5 https://doi.org/10.1016/S1872-5805(20)60512-1	journal	September 2020
Low shear rheological behaviour of two-phase mesophase pitch Ramjee, Shatish; Rand, Brian; Focke, Walter W. Carbon, Vol. 82 https://doi.org/10.1016/j.carbon.2014.10.082	journal	February 2015
Manufacturing spinnable mesophase pitch using direct coal extracted fraction and its derived mesophase pitch based carbon fiber Shimanoe, Hiroki; Mashio, Takashi; Nakabayashi, Koji Carbon, Vol. 158 https://doi.org/10.1016/j.carbon.2019.11.082	journal	March 2020
Isotropic pitch-derived carbon fiber from waste coal Craddock, John D.; Frank, George; Martinelli, Michela Carbon, Vol. 216 https://doi.org/10.1016/j.carbon.2023.118590	journal	January 2024
Processing, structure, and properties of carbon fibers Newcomb, Bradley A. Composites Part A: Applied Science and Manufacturing, Vol. 91 https://doi.org/10.1016/j.compositesa.2016.10.018	journal	December 2016
Mild coal extraction for the production of anode coke from Blue Gem coal Andrews, Rodney J.; Rantell, Terry; Jacques, David Fuel, Vol. 89, Issue 9 https://doi.org/10.1016/j.fuel.2010.04.027	journal	September 2010
Study on the aggregation of coal liquefied preasphaltene in organic solvents by UV–vis and fluorescence spectrophotometry Wang, Zhicai; Li, Liang; Shui, Hengfu Fuel, Vol. 90, Issue 1 https://doi.org/10.1016/j.fuel.2010.08.009	journal	January 2011
The molecular representations of coal – A review Mathews, Jonathan P.; Chaffee, Alan L. Fuel, Vol. 96 https://doi.org/10.1016/j.fuel.2011.11.025	journal	June 2012
Effects of different extracted components from petroleum pitch on mesophase development Li, Ming; Liu, Dong; Men, Zhuowu Fuel, Vol. 222 https://doi.org/10.1016/j.fuel.2018.03.011	journal	June 2018
Modified effect on properties of mesophase pitch prepared from various two-stage thermotreatments of FCC decant oil Lou, Bin; Liu, Dong; Qiu, Yu Fuel, Vol. 284 https://doi.org/10.1016/j.fuel.2020.119034	journal	January 2021
Microstructural diversity and digestion yields of select bituminous and subbituminous coals as raw material candidates for carbon fiber precursor production Cakmak, Ercan; Hower, James C.; Mathews, Jonathan P. Fuel, Vol. 348 https://doi.org/10.1016/j.fuel.2023.128545	journal	September 2023
Molecular structure and size of asphaltene and preasphaltene from direct coal liquefaction Wang, Zhi-Cai; Ge, Yan; Shui, Heng-Fu Fuel Processing Technology, Vol. 137 https://doi.org/10.1016/j.fuproc.2015.03.015	journal	September 2015
Accelerating the oxidative stabilization of pitch fibers and improving the physical performance of carbon fibers by modifying naphthalene-based mesophase pitch with C9 resin Jin, Zhao; Zuo, Xiaohua; Long, Xiangyi Journal of Analytical and Applied Pyrolysis, Vol. 154 https://doi.org/10.1016/j.jaap.2020.105009	journal	March 2021
Hydrogenation of coal tar pitch for improved mesophase pitch molecular orientation and carbon fiber processing Guo, Jianguang; Li, Zhong; Li, Baoliu Journal of Analytical and Applied Pyrolysis, Vol. 174 https://doi.org/10.1016/j.jaap.2023.106146	journal	September 2023
Molecular Structure Control in Mesophase Pitch via Co-Carbonization of Coal Tar Pitch and Petroleum Pitch for Production of Carbon Fibers with Both High Mechanical Properties and Thermal Conductivity Guo, Jianguang; Li, Xuanke; Xu, Huitao Energy & Fuels, Vol. 34, Issue 5 https://doi.org/10.1021/acs.energyfuels.0c00196	journal	April 2020
Preparation of the Mesophase Pitch by Hydrocracking Tail Oil from a Naphthenic Vacuum Residue Li, Ming; Liu, Dong; Lv, Renqing Energy & Fuels, Vol. 29, Issue 7 https://doi.org/10.1021/acs.energyfuels.5b00537	journal	July 2015
Solvolysis of Bituminous Coal in Coal- and Petroleum-Derived Commercial Solvents Kuznetsov, Peter N.; Kamenskiy, Evgeny S.; Kuznetsova, Ludmila I. ACS Omega, Vol. 5, Issue 24 https://doi.org/10.1021/acsomega.0c00915	journal	June 2020
Constructing the Bridge from Isotropic to Anisotropic Pitches for Preparing Pitch-Based Carbon Fibers with Tunable Structures and Properties Yuan, Guanming; Xue, Zheng; Cui, Zhengwei ACS Omega, Vol. 5, Issue 34 https://doi.org/10.1021/acsomega.0c03226	journal	August 2020
Effect of Liquid Crystalline Texture of Mesophase Pitches on the Structure and Property of Large-Diameter Carbon Fibers Yuan, Guanming; Li, Baoliu; Li, Xuanke ACS Omega, Vol. 4, Issue 1 https://doi.org/10.1021/acsomega.8b03189	journal	January 2019
Chemicals from Direct Coal Liquefaction Mochida, Isao; Okuma, Osamu; Yoon, Seong-Ho Chemical Reviews, Vol. 114, Issue 3 https://doi.org/10.1021/cr4002885	journal	December 2013
The Calibration of Size Exclusion Chromatography Columns: Molecular Mass Distributions of Heavy Hydrocarbon Liquids Karaca, Fatma; Islas, Carlos A.; Millan, Marcos Energy & Fuels, Vol. 18, Issue 3 https://doi.org/10.1021/ef030178h	journal	March 2004
Characterization of Maya Crude Oil Maltenes and Asphaltenes in Terms of Structural Parameters Calculated from Nuclear Magnetic Resonance (NMR) Spectroscopy and Laser Desorption−Mass Spectroscopy (LD−MS) Morgan, T. J.; Alvarez-Rodriguez, P.; George, A. Energy & Fuels, Vol. 24, Issue 7 https://doi.org/10.1021/ef100320t	journal	June 2010
Structural Characterization and Aggregation of the Subfractions of Preasphaltene from Direct Coal Liquefaction Wang, Zhicai; Zhao, Zhijun; Shui, Hengfu Energy & Fuels, Vol. 28, Issue 12 https://doi.org/10.1021/ef501661f	journal	November 2014
Novel Use of Residue from Direct Coal Liquefaction Process^† Yang, Jianli; Wang, Zhaixia; Liu, Zhenyu Energy & Fuels, Vol. 23, Issue 10 https://doi.org/10.1021/ef9000083	journal	October 2009
Classification of Asphaltenes via Fractionation and the Effect of Heteroatom Content on Dissolution Kinetics Kaminski, Thomas J.; Fogler, H. Scott; Wolf, Nick Energy & Fuels, Vol. 14, Issue 1 https://doi.org/10.1021/ef990111n	journal	December 1999
Solvation and Hydrogenation of Coal Orchin, Milton; Storch, H. H. Industrial & Engineering Chemistry, Vol. 40, Issue 8 https://doi.org/10.1021/ie50464a010	journal	August 1948
Studies on Asphaltenes through Analysis of Polar Fractions Nalwaya, Vaibhav; Tantayakom, Veerapat; Piumsomboon, Pornpote Industrial & Engineering Chemistry Research, Vol. 38, Issue 3 https://doi.org/10.1021/ie9804428	journal	February 1999
Review Carbon fibers for composites Chand, S. Journal of Materials Science, Vol. 35, Issue 6, p. 1303-1313 https://doi.org/10.1023/A:1004780301489	journal	January 2000
Hydroalkylation modification of naphthene-based aromatic-rich fraction and its influences on mesophase development Li, Ming; Liu, Dong; Lou, Bin RSC Advances, Vol. 8, Issue 7 https://doi.org/10.1039/C7RA12619K	journal	January 2018
Research progress in the preparation of mesophase pitch from fluid catalytic cracking slurry Wang, Mingzhi; Yang, Bei; Yu, Tao RSC Advances, Vol. 13, Issue 27 https://doi.org/10.1039/D3RA01726E	journal	January 2023
Preparation and characterization of high performance coal tar pitch-based carbon fiber Zhang, Dakui; Mu, Chunfeng; He, Ying Fullerenes, Nanotubes and Carbon Nanostructures, Vol. 32, Issue 2 https://doi.org/10.1080/1536383X.2023.2264417	journal	October 2023
Study on spinning stability and microstructure of mesophase pitch Chen, Shi-Lin; Ma, Zhi-Cheng; Fan, Chang-Ling Materials Express, Vol. 10, Issue 10 https://doi.org/10.1166/mex.2020.1802	journal	October 2020
Direct Preparation of Mesophase Pitch from Naphthalene by the Aid of HF/BF3 Mochida, Isao; Shimizu, Kiyoyuki; Korai, Yozo Chemistry Letters, Vol. 18, Issue 11 https://doi.org/10.1246/cl.1989.1893	journal	November 1989
Asphaltenes and preasphaltenes from coal liquid extracts: feedstocks to obtain carbon mesophase Barraza, Juan; Muñoz, Natalia; Barona, Lina Revista Facultad de Ingeniería Universidad de Antioquia, Issue 70 https://doi.org/10.17533/udea.redin.16169	journal	February 2014