NMR analysis of the Fischer-Tropsch wastewater: Combination of 1D selective gradient TOCSY, 2D DOSY and qNMR

Analytica Chimica Acta - Tập 1066 - Trang 21-27 - 2019
Hui Ma1,2, Christian Marcus Pedersen3, Qi Zhao1,2, Zexiang Lyu1,2, Hui Chang4, Yan Qiao1,2, Xianglin Hou1,2, Yingxiong Wang1,2
1Shanxi Engineering Research Center of Biorefinery, Institute of Coal Chemistry, University of Chinese Academy of Sciences, 27 South Taoyuan Road, Taiyuan, 030001, China
2Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing, 100049, China
3Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark
4Sinopec Shanghai Petrochemical Co., Ltd, 48 Jinyi Road, Jinshan District, Shanghai, 200540, China

Tài liệu tham khảo

Timko, 2010, Particulate emissions of gas turbine engine combustion of a Fischer−Tropsch synthetic fuel, Energy Fuels, 24, 5883, 10.1021/ef100727t Dry, 2002, High quality diesel via the Fischer-Tropsch process - a review, J. Chem. Technol. Biotechnol., 77, 43, 10.1002/jctb.527 Steynberg, 2004, Introduction to fischer-tropsch technology, 1 Wang, 2017, Enhanced treatment of Fischer-Tropsch (F-T) wastewater using the up-flow anaerobic sludge blanket coupled with bioelectrochemical system: effect of electric field, Bioresour. Technol., 232, 18, 10.1016/j.biortech.2017.02.010 Nel, 2007, Fischer-tropsch aqueous phase refining by catalytic alcohol dehydration, Ind. Eng. Chem. Res., 46, 3558, 10.1021/ie061555r Wang, 2017, Enhanced treatment of Fischer–Tropsch (F-T) wastewater by novel anaerobic biofilm system with scrap zero valent iron (SZVI) assisted, Biochem. Eng. J., 117, 66, 10.1016/j.bej.2016.09.012 Ma, 2018, The interaction between Fischer–Tropsch wastewater and humic acid: a NMR study of butanol isomers, Fuel Process. Technol., 179, 296, 10.1016/j.fuproc.2018.07.019 Chen, 2012, Catalytic degradation of oxygenates in Fischer-Tropsch aqueous phase effluents to fuel gas via hydrodeoxygenation over Ru/AC catalyst, J. Chem. Technol. Biotechnol., 87, 112, 10.1002/jctb.2690 Bottomley, 1982, NMR imaging techniques and applications: a review, Rev. Sci. Instrum., 53, 1319, 10.1063/1.1137180 Zhang, 2014, NMR analysis of by-products in imidacloprid production, Chin. J. Magn. Reson., 31, 364 Kimura, 2013, Solvent effect on pathways and mechanisms for D-fructose conversion to 5-hydroxymethyl-2-furaldehyde: in situ 13C NMR study, J. Phys. Chem. A, 117, 2102, 10.1021/jp312002h Kuroda, 2014, H-1 NMR evaluation of polar and nondeuterated ionic liquids for selective extraction of cellulose and xylan from wheat bran, ACS Sustain. Chem. Eng., 2, 2204, 10.1021/sc500407a Amarasekara, 2014, Mechanism of 1-(1-propylsulfonic)-3-methylimidazolium chloride catalyzed transformation of D-glucose to 5-hydroxymethylfurfural in DMSO: an NMR study, Carbohydr. Res., 386, 86, 10.1016/j.carres.2014.01.009 Hoffman, 2008, High-resolution NMR "chromatography" using a liquids spectrometer, J. Magn. Reson., 194, 295, 10.1016/j.jmr.2008.06.022 J, 1999, Diffusion ordered nuclear magnetic resonance spectroscopy: principles and applications, Nucl. Magn. Reson. Spectrosc., 34, 203, 10.1016/S0079-6565(99)00003-5 Li, 2009, Formula weight prediction by internal reference diffusion-ordered NMR spectroscopy (DOSY), J. Am. Chem. Soc., 131, 5627, 10.1021/ja810154u Einstein, 1905, Über die von der molekularkinetischen Theorie der Wärme geforderte Bewegung von in ruhenden Flüssigkeiten suspendierten Teilchen, Ann. Phys., 322, 549, 10.1002/andp.19053220806 Wang, 2017, Direct analysis of succinic acid fermentation broth by 1H diffusion-ordered NMR spectroscopy and quantitative 1H NMR technique, ACS Sustain. Chem. Eng., 5, 2824, 10.1021/acssuschemeng.6b03184 Ge, 2016, DOSY NMR: a versatile analytical chromatographic tool for lignocellulosic biomass conversion, ACS Sustain. Chem. Eng., 4, 1193, 10.1021/acssuschemeng.5b01259 Ning, 2018, Ca2+-Assisted DOSY NMR: an unexpected tool for anomeric identification for d-glucopyranose, ChemistrySelect, 3, 3943, 10.1002/slct.201800316 Tormena, 2010, Matrix-assisted diffusion-ordered spectroscopy: mixture resolution by NMR using SDS micelles, Magn. Reson. Chem., 48, 550, 10.1002/mrc.2621 Huang, 2014, Polydimethylsiloxane: a general matrix for high-performance chromatographic NMR spectroscopy, Angew. Chem. Int. Ed., 53, 11592, 10.1002/anie.201406967 Facke, 1995, Application of pulsed field gradients in an improved selective TOCSY experiment, J. Magn. Reson., Ser. A, 113, 257, 10.1006/jmra.1995.1090 Howe, 2006, Removal of zero-quantum peaks from 1D selective TOCSY and NOESY spectra, J. Magn. Reson., 179, 217, 10.1016/j.jmr.2005.12.004 Xu, 1996, The application of "excitation sculpting" in the construction of selective one-dimensional homonuclear coherence-transfer experiments, J. Magn. Reson. Ser. B, 111, 183, 10.1006/jmrb.1996.0079 Yue, 2018, NMR studies of stock process water and reaction pathways in hydrothermal carbonization of furfural residue, Green Energy Environ., 3, 163, 10.1016/j.gee.2017.08.006 Lyu, 2018, DOSY plus selective TOCSY: an efficient NMR combination for analyzing hydrogenation/hydrogenolysis mixtures of biomass-derived platform compounds, Energy Fuels, 32, 3551, 10.1021/acs.energyfuels.7b03992 Lyu, 2018, Combination of DOSY and 1D selective gradient TOCSY: versatile NMR tools for identify the mixtures from glycerol hydrogenolysis reaction, Fuel Process. Technol., 171, 117, 10.1016/j.fuproc.2017.11.011 Huang, 2018, Effects of digital resolution on diffusional dimension in DOSY experiments, Chin. J. Magn. Reson., 35, 287 Bernstein, 2013, Optimization and automation of quantitative NMR data extraction, Anal. Chem., 85, 5778, 10.1021/ac400411q Cohen, 2005, Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: an old parameter—new insights, Angew. Chem. Int. Ed., 44, 520, 10.1002/anie.200300637 Laurette, 2010, Subterahertz characterization of ethanol hydration layers by microfluidic system, Appl. Phys. Lett., 97, 10.1063/1.3488832 Cabrita, 2001, DOSY studies of hydrogen bond association: tetramethylsilane as a reference compound for diffusion studies, Magn. Reson. Chem., 39, S142, 10.1002/mrc.917 Novoa-Carballal, 2011, NMR methods for unravelling the spectra of complex mixtures, Nat. Prod. Rep., 28, 78, 10.1039/C005320C Chen, 2012, Catalytic degradation of aqueous Fischer-Tropsch effluents to fuel gas over oxide-supported Ru catalysts and hydrothermal stability of catalysts, J. Chem. Technol. Biotechnol., 87, 1089, 10.1002/jctb.3719 Rundlof, 2010, Survey and qualification of internal standards for quantification by 1H NMR spectroscopy, J. Pharm. Biomed. Anal., 52, 645, 10.1016/j.jpba.2010.02.007