Analysis of mixed plastic pyrolysis oil by comprehensive two-dimensional gas chromatography coupled with low- and high-resolution time-of-flight mass spectrometry with the support of soft ionization.
Central composite design (CCD); Comprehensive 2D-GC (GC×GC)-TOFMS; GC soft Ionization HRMS; PTV optimization; Photoionization interface (PI); Plastic pyrolysis oil; Plastics; Bio-Oil; Plant Oils; Organic Chemicals; Gas Chromatography-Mass Spectrometry/methods; Mass Spectrometry/methods; Plant Oils/chemistry; Pyrolysis; Central composite design; Central composite designs; GC×GC-TOFMS; Optimisations; Photoionization interface; Plastic pyrolyse oil; Plastic pyrolysis; Pyrolysis oil; Soft ionization; Gas Chromatography-Mass Spectrometry; Mass Spectrometry; Analytical Chemistry
Abstract :
[en] According to the annual production of plastics worldwide, in 2020 about 370 million tons of plastic were produced in the world. Chemical recycling, particularly pyrolysis of plastic wastes, could be a valuable solution to resolve these problems and provide an alternative pathway to produce "recycled" chemical products for the petrochemical industry. Nevertheless, the pyrolysis oils need a detailed characterization before the upgrading test to re-use them to generate new recycled products. Multidimensional gas chromatography coupled with both low- and high-resolution time-of-flight mass spectrometers was employed for a detailed investigation among and within different chemical classes present in bio-plastic oil. The presence of several isomeric species as well as homologs series did not allow a reliable molecular identification, except for a few compounds that showed both MS similarity >800/1000 and retention index within ±20. Indeed, the identification of several isomeric species was assessed by high-resolution mass spectrometry equipped with photoionization interface. This soft ionization mode was an additional filter in the identification step allowing unambiguous identification of analytes not identified by the standard electron ionization mode at 70 eV. The injection method was also optimized using a central composite design to successfully introduce a wide range of carbon number compounds without discrimination of low/high boiling points.
Disciplines :
Chemistry
Author, co-author :
Beccaria, Marco ; Université de Liège - ULiège > Molecular Systems (MolSys)
Piparo, Marco; TotalEnergies One Tech, R&D, Downstream Processes & Polymers, Total Research and Technologies, Gonfreville, France, International Joint Laboratory - iC2MC: Complex Matrices Molecular Characterization, TRTG, Harfleur, France
Zou, Yun ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique, organique et biologique
Stefanuto, Pierre-Hugues ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique, organique et biologique
Purcaro, Giorgia ; Université de Liège - ULiège > TERRA Research Centre > Chimie des agro-biosystèmes
Mendes Siqueira, Anna Luiza; TotalEnergies One Tech, R&D, Fuels & Lubricants, Solaize Research Center, Solaize, France
Maniquet, Adrien; TotalEnergies One Tech, R&D, Fuels & Lubricants, Solaize Research Center, Solaize, France
Giusti, Pierre; TotalEnergies One Tech, R&D, Downstream Processes & Polymers, Total Research and Technologies, Gonfreville, France, International Joint Laboratory - iC2MC: Complex Matrices Molecular Characterization, TRTG, Harfleur, France
Focant, Jean-François ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique, organique et biologique
Language :
English
Title :
Analysis of mixed plastic pyrolysis oil by comprehensive two-dimensional gas chromatography coupled with low- and high-resolution time-of-flight mass spectrometry with the support of soft ionization.
Palos, R., Gutiérrez, A., Vela, F.J., Olazar, M., Arandes, J.M., Bilbao, J., Waste refinery: the valorization of waste plastics and end-of-life tires in refinery units. A Review, Energy and Fuels 35 (2021), 3529–3557, 10.1021/acs.energyfuels.0c03918.
Filho, W.L., Salvia, A.L., Bonoli, A., Saari, U.A., Voronova, V., Klõga, M., Kumbhar, S.S., Olszewski, K., de Quevedo, D.M., Barbir, J., An assessment of attitudes towards plastics and bioplastics in Europe. Sci. Total Environ., 2021, 755, 10.1016/j.scitotenv.2020.142732.
PlascticsEurope, Plastics-the Facts 2020 An analysis of European plastics production, demand and waste data, n.d. https://doi.org/https://plasticseurope.org/wp-content/uploads/2021/09/Plastics_the_facts-WEB-2020_versionJun21_final.pdf.
Singh, N., Hui, D., Singh, R., Ahuja, I.P.S., Feo, L., Fraternali, F., Recycling of plastic solid waste: a state of art review and future applications. Compos. B Eng. 115 (2017), 409–422, 10.1016/j.compositesb.2016.09.013.
Solis, M., Silveira, S., Technologies for chemical recycling of household plastics – a technical review and TRL assessment. Waste Manag. 105 (2020), 128–138, 10.1016/j.wasman.2020.01.038.
Geyer, R., Jambeck, J.R., Law, K.L., Production, Use, and Fate of All Plastics Ever Made. 2017.
Toraman, H.E., Dijkmans, T., Djokic, M.R., Van Geem, K.M., Marin, G.B., Detailed compositional characterization of plastic waste pyrolysis oil by comprehensive two-dimensional gas-chromatography coupled to multiple detectors. J. Chromatogr. A 1359 (2014), 237–246, 10.1016/j.chroma.2014.07.017.
Dao Thi, H., Djokic, M.R., van Geem, K.M., Detailed group-type characterization of plastic-waste pyrolysis oils: by comprehensive two-dimensional gas chromatography including linear, branched, and di-olefins. Separations, 8, 2021, 10.3390/separations8070103.
Quesada, L., Calero, M., Martín-Lara, M.A., Pérez, A., Blázquez, G., Characterization of fuel produced by pyrolysis of plastic film obtained of municipal solid waste. Energy, 186, 2019, 10.1016/j.energy.2019.115874.
Kaminsky, W., Kim, J.S., Pyrolysis of mixed plastics into aromatics. J. Anal. Appl. Pyrol. 51 (1999), 127–134, 10.1016/S0165-2370(99)00012-1.
Beccaria, M., Siqueira, A.L.M., Maniquet, A., Giusti, P., Piparo, M., Stefanuto, P.H., Focant, J.F., Advanced mono- and multi-dimensional gas chromatography–mass spectrometry techniques for oxygen-containing compound characterization in biomass and biofuel samples. J. Separ. Sci. 44 (2021), 115–134, 10.1002/jssc.202000907.
Giri, A., Coutriade, M., Racaud, A., Okuda, K., Dane, J., Cody, R.B., Focant, J.F., Molecular characterization of volatiles and petrochemical base oils by photo-ionization GC×GC-TOF-MS. Anal. Chem. 89 (2017), 5395–5403, 10.1021/acs.analchem.7b00124.
Giri, A., Coutriade, M., Racaud, A., Stefanuto, P.H., Okuda, K., Dane, J., Cody, R.B., Focant, J.F., Compositional elucidation of heavy petroleum base oil by GC × GC-EI/PI/CI/FI-TOFMS. J. Mass Spectrom. 54 (2019), 148–157, 10.1002/jms.4319.
Zou, Y., Stefanuto, P., Maimone, M., Janssen, M., Focant, J.-F., Unraveling the complex olefin isomer mixture using two-dimensional gas chromatography-photoionization-time of flight mass spectrometry. J. Chromatogr. A, 1645, 2021, 462103, 10.1016/j.chroma.2021.462103.
Purcaro, G., Barp, L., Beccaria, M., Conte, L.S., Fingerprinting of vegetable oil minor components by multidimensional comprehensive gas chromatography with dual detection. Anal. Bioanal. Chem. 407 (2015), 309–319, 10.1007/s00216-014-8140-x.
Salivo, S., Beccaria, M., Sullini, G., Tranchida, P.Q., Dugo, P., Mondello, L., Analysis of human plasma lipids by using comprehensive two-dimensional gas chromatography with dual detection and with the support of high-resolution time-of-flight mass spectrometry for structural elucidation. J. Separ. Sci. 38:2 (2015), 267–275, 10.1002/jssc.201400844.
Beccaria, M., Zou, Y., Stefanuto, P.H., Siqueira, A.L.M., Maniquet, A., Piparo, M., Giusti, P., Purcaro, G., Focant, J.F., Deeper investigation of oxygen-containing compounds in oleaginous feedstock (animal fat) by preparative column chromatography and comprehensive two-dimensional gas chromatography coupled with high-resolution time-of-flight mass spectrometry. Talanta, 238, 2022, 10.1016/j.talanta.2021.123019.
Ware, R.L., Rowland, S.M., Rodgers, R.P., Marshall, A.G., Advanced chemical characterization of pyrolysis oils from landfill waste, recycled plastics, and forestry residue. Energy Fuel. 31 (2017), 8210–8216, 10.1021/acs.energyfuels.7b00865.
Nunes, V.O., Silva, R.V.S., Romeiro, G.A., Azevedo, D.A., The speciation of the organic compounds of slow pyrolysis bio-oils from Brazilian tropical seed cake fruits using high-resolution techniques: GC × GC-TOFMS and ESI(±)-Orbitrap HRMS. Microchem. J., 153, 2020, 104514, 10.1016/j.microc.2019.104514.
Tessarolo, N.S., Silva, R.C., Vanini, G., Pinho, A., Romão, W., de Castro, E.V.R., Azevedo, D.A., Assessing the chemical composition of bio-oils using FT-ICR mass spectrometry and comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry. Microchem. J. 117 (2014), 68–76, 10.1016/j.microc.2014.06.006.
Staš, M., Auersvald, M., Vozka, P., Two-dimensional gas chromatography characterization of pyrolysis bio-oils: a review. Energy Fuel. 35:10, (2021), 8541–8557, 10.1021/acs.energyfuels.1c00553.
Mase, C., Maillard, J.F., Paupy, B., Farenc, M., Adam, C., Hubert-Roux, M., Afonso, C., Giusti, P., Molecular characterization of a mixed plastic pyrolysis oil from municipal wastes by direct infusion fourier transform ion cyclotron resonance mass spectrometry. Energy Fuel. 35 (2021), 14828–14837, 10.1021/acs.energyfuels.1c01678.
Biedermann, M., Grob, K., Comprehensive two-dimensional gas chromatography for characterizing mineral oils in foods and distinguishing them from synthetic hydrocarbons. J. Chromatogr. A 1375 (2015), 146–153, 10.1016/j.chroma.2014.11.064.
Biedermann-Brem, S., Kasprick, N., Simat, T., Grob, K., Migration of polyolefin oligomeric saturated hydrocarbons (POSH) into food, Food Additives and Contaminants - Part A Chemistry. Analysis, Control, Exposure and Risk Assessment 29 (2012), 449–460, 10.1080/19440049.2011.641164.
Tranchida, P.Q., Aloisi, I., Giocastro, B., Mondello, L., Current state of comprehensive two-dimensional gas chromatography-mass spectrometry with focus on processes of ionization. TrAC, Trends Anal. Chem. 105 (2018), 360–366, 10.1016/j.trac.2018.05.016.
Beccaria, M., Franchina, F.A., Nasir, M., Mellors, T., Hill, J.E., Purcaro, G., Investigation of mycobacteria fatty acid profile using different ionization energies in GC–MS. Anal. Bioanal. Chem. 410 (2018), 7987–7996, 10.1007/s00216-018-1421-z.
Glineur, A., Beccaria, M., Purcaro, G., Exploring 20 eV electron impact ionization in gas chromatography-tandem mass spectrometry for the determination of estrogenic compounds. J. Chromatogr. A, 1652, 2021, 462359, 10.1016/j.chroma.2021.462359.
Piparo, M., Flamant, L., Jousset, G., Cardinael, P., Giusti, P., Careful investigations of PTV injection parameters for the analysis of vacuum gas oil by high-temperature comprehensive GC × GC. Energy Fuel., 34, 2020, 12010, 10.1021/acs.energyfuels.0c01314 12017.
Purcaro, G., Stefanuto, P.H., Franchina, F.A., Beccaria, M., Wieland-Alter, W.F., Wright, P.F., Hill, J.E., SPME-GC×GC-TOF MS fingerprint of virally-infected cell culture: sample preparation optimization and data processing evaluation. Anal. Chim. Acta 1027 (2018), 158–167, 10.1016/j.aca.2018.03.037.
Van Bramer, S.E., Ross, P.L., V Johnston, M., Unimolecular photochemistry of n-alkenes studied by photodissociation-photoionization mass spectrometry. J. Am. Soc. Mass Spectrom. 4 (1993), 65–72.
Armenise, S., SyieLuing, W., Ramírez-Velásquez, J.M., Launay, F., Wuebben, D., Ngadi, N., Rams, J., Muñoz, M., Plastic waste recycling via pyrolysis: a bibliometric survey and literature review. J. Anal. Appl. Pyrol., 158, 2021, 10.1016/j.jaap.2021.105265.
