Characterization of organosulfur compounds in asphalt cement samples by ESI(+)FT-ICR MS and 13C NMR spectroscopy

Porto, Christiane F.C.; Pinto, Fernanda E.; Souza, Lindamara M.; Madeira, Natã C. L.; Neto, Álvaro Cunha; Menezes, Sônia Maria Cabral de; Chinelatto, Luiz S.; Freitas, Carla; Vaz, Boniek G.; Lacerda, Valdemar; Romão, Wanderson

doi:10.1016/j.fuel.2019.115923

Cited by 25 publications

(18 citation statements)

References 41 publications

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“…Previous studies report the abundance of sulfur-containing species in asphalt binder, which is confirmed for this sample (Figure S1); thus, we focus on sulfur-containing photoproducts (O x S 1 ) in the water-soluble extract from irradiated asphalt. The sulfur-containing water-soluble photoproducts from 168 h irradiated asphalt are illustrated in Figure by isoabundance-contoured plots of DBE versus carbon number (top panel) and the corresponding heteroatom compound class distribution (bottom panel) showing the relative abundance (%) for each compound class.…”

Section: Resultssupporting

confidence: 69%

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Characterization of an Asphalt Binder and Photoproducts by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Reveals Abundant Water-Soluble Hydrocarbons

Niles

Chacón-Patiño

Putnam

et al. 2020

Environ. Sci. Technol.

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Road asphalt is comprised of aggregate (rocks) mixed with a binder composed of high-boiling petroleum-derived compounds, which have been thought to be relatively inert (unreactive) and thus leach small amounts of polyaromatic hydrocarbons (PAHs) into water from the built environment. However, recent studies have demonstrated that petroleum readily undergoes photooxidation and generates water-soluble oxygencontaining hydrocarbons. Therefore, here, we investigate the effects of solar irradiation on an asphalt binder. Upon irradiation in a photooxidation microcosm, thin films of the asphalt binder produce abundant oil-and water-soluble oxygenated hydrocarbons, which we hypothesize are also leached from roads and highways through photooxidation reactions. Ultrahigh-resolution Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) enables extensive compositional characterization of the virgin asphalt binder, irradiated asphalt binder, and the water-soluble photoproducts. The results reveal the production of water-soluble species that resemble the molecular composition of petroleum-derived dissolved organic matter, including abundant hydrocarbons and Scontaining species with up to 18 oxygen atoms. The results also confirm photo-induced oxidation, fragmentation, and potentially polymerization as active processes involved in the production of water-soluble organic pollutants from asphalt.

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Section: Resultssupporting

confidence: 69%

“…An asphalt binder has been previously analyzed by positive-ion (+) electrospray (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) to reveal abundant sulfur-containing species, including sulfides, thiophenes, and dibenzothiophenes . The authors also report 19–34 wt % asphaltenes for three asphalt binders.…”

Section: Introductionmentioning

confidence: 99%

Characterization of an Asphalt Binder and Photoproducts by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Reveals Abundant Water-Soluble Hydrocarbons

Niles

Chacón-Patiño

Putnam

et al. 2020

Environ. Sci. Technol.

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“…68 Furthermore, Porto et al (2019) found evidence that asphalt concretes containing a high amount of nonaromatic sulfur compounds are prevalently affected by short-term aging. 72 According to previous studies, 1,9,26,28 sulfoxides are one of the main functional groups formed during oxidative aging in bitumen. For FT-ICR MS data, already the average parameters for core structures in the desorption phase and for both modes in the pyrolysis phase reveal a distinct increase of the S1O1class.…”

Section: ■ Results and Discussionmentioning

confidence: 97%

“…Lobodin et al (2015) already revealed that crude oil is composed of reactive (sulfides, disulfides, and thiols) and nonreactive (thiophenes and diaryl sulfides) sulfur species . Furthermore, Porto et al (2019) found evidence that asphalt concretes containing a high amount of nonaromatic sulfur compounds are prevalently affected by short-term aging …”

Section: Results and Discussionmentioning

confidence: 99%

Investigation of Aging Processes in Bitumen at the Molecular Level with High-Resolution Fourier-Transform Ion Cyclotron Mass Spectrometry and Two-Dimensional Gas Chromatography Mass Spectrometry

et al. 2020

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Bitumen is a highly viscous and chemically complex petroleum-derived material, which is applied as a binder in road construction. However, the asphalt undergoes hardening, cracking, and embrittlement not only due to oxidative short-term aging during the mixing and paving process but also due to long-term aging during the service time of the pavement. In this study, chemical changes occurring during short-term aging, mimicked by a prolonged rotating flask procedure, are investigated for an artificial bitumen model at the molecular level. The model bitumen enables the application of two complementary analytical techniques for obtaining a comprehensive insight into the aging effects: high-resolution Fourier-transform ion cyclotron mass spectrometry (FT-ICR MS) coupled to thermogravimetry was applied to investigate the aging effects on polar to semipolar high-molecular-weight compounds ionized by atmospheric pressure chemical ionization. Aromatic core structures were analyzed by alternating collision-induced dissociation. In order to support structural assignments from FT-ICR MS data in the semivolatile region, comprehensive two-dimensional gas chromatography mass spectrometry (GC × GC–HRTOFMS) with electron ionization at 70 eV was applied for the group-type analysis and the investigation of particular chemical functionalities. Oxidation processes were revealed to be the prevalent reactions caused by short-term aging of the hydrocarbons (CH-class) and sulfur-containing classes. Aromatic species with low steric hindrance or activated carbon positions as well as high aromatic core structures are favorably oxidized, forming carbonyl functionalities. For molecules with one sulfur atom (S1-class), nonaromatic species such as tetrahydrothiophenes decrease, whereas aromatic S1-compounds remain constant. Nonaromatic S1O1-species tend to further oxidize, while higher aromatic species are formed with ongoing aging time. Moreover, this study highlights the aging behavior of nitrogen-containing compounds, such as carbazoles. A significant reduction of the N-classes was observed during aging, indicating thermal-induced condensation reactions as well as favored oxidation of highly aromatic core structures.

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“…In recent years, the number of studies regarding the search for improving the quality and lifespan of petroleum asphalt cement (AC) has increased considerably . To achieve this goal, it is essential to know its chemical composition and the effects of the aging processes.…”

Section: Introductionmentioning

confidence: 99%

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

et al. 2021

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The study of petroleum asphalt cement (AC) aging is essential for the production of good quality pavements with high durability. Because of the complexity of this material, one of the biggest challenges is understanding the chemical variations that occur in the molecules present in the AC during the aging processes. This work proposes to study 15 standards of model compounds present in the AC composition, representing the fractions of saturated compounds (5-α-cholestane and hexatriacontane), aromatics (hexamethylbenzene, coronene, and benzo-[a]anthracene), nitrogenous compounds (acridine, carbazole, indole, and N,N′-Bis(3-pentyl)perylene-3,4,9,10-bis-(dicarboximide)), sulfur compounds (2-naphthalenethiol, 4,6diethyldibenzothiophene, and naphtho[1,2-b:6,5-b′]dithiophene(NDT)), and naphthenic acids (stearic (SA), pentadecanoic (PA), and sinapinic acids (ASN)), which were thermally aged by two methods: (i) they were subjected to a constant temperature of 80 °C, varying the time of analysis over 5, 10, 15, 30, and 60 days; and (ii) temperatures ranging from 80, 100, 120, to 140 °C for 15 days. The analyses of these compounds were performed by GC/MS, 1 H and 13 C NMR, ESI(−)MS (FT-ICR and LTQ), and FTIR. The results obtained showed that at 80 °C, from 15 days, only the indole standard compound showed the presence of thermal products, i.e., compounds detected from thermal aging of the standard model compounds. When the degradation temperature was increased from 100 to 140 °C, we observed the formation of thermal products at 100 °C in 6 out of 15 model compounds. However, at 140 °C, 12 of the 15 model compounds presented some type of degradation. Reactions of oxidation, polymerization, thermal aging, volatilization, and formation of double bonds were observed.

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Characterization of organosulfur compounds in asphalt cement samples by ESI(+)FT-ICR MS and 13C NMR spectroscopy

Cited by 25 publications

References 41 publications

Characterization of an Asphalt Binder and Photoproducts by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Reveals Abundant Water-Soluble Hydrocarbons

Characterization of an Asphalt Binder and Photoproducts by Fourier Transform Ion Cyclotron Resonance Mass Spectrometry Reveals Abundant Water-Soluble Hydrocarbons

Investigation of Aging Processes in Bitumen at the Molecular Level with High-Resolution Fourier-Transform Ion Cyclotron Mass Spectrometry and Two-Dimensional Gas Chromatography Mass Spectrometry

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

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