Ruthenium Ion-Catalyzed Oxidation for Petroleum Molecule Structural Features: A Review

Shi, Quan; Wang, Jiawei; Zhou, Xibin; Chen, Xu; Zhao, Suoqi; Chung, Keng H.

doi:10.1007/430_2015_180

Cited by 9 publications

(9 citation statements)

References 81 publications

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“…Ruthenium-ion-catalyzed oxidation (RICO) and subsequent analyses proved to be an effective method for characterizing alkyl side chains on aromatic rings, alkylene bridges connecting aromatic rings, and condensed aromatic rings in coals − and other heavy carbon resources. − It is usually accepted that arylalkanes, α,ω-diarylalkanes, triarylalkanes, and condensed aromatics could be selectively oxidized into alkanoic acids (AAs), alkanedioic acids (ADAs), alkanetricarboxylic acids (ATCAs), and benzenecarboxylic acids (BCAs), respectively, by RICO (Scheme S1 of the Supporting Information).…”

Section: Introductionmentioning

confidence: 99%

Effect of Ethanolysis on the Structure and Pyrolytic Reactivity of Zhaotong Lignite

Wei

Yan

et al. 2017

Energy Fuels

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Lignite ethanolysis is one of the efficient conversion processes. In our previous study, Zhaotong lignite (ZL) from Southwest China was subjected to ethanolysis to afford an ethanol-soluble portion and ethanolyzed residue (ER). The structural features of ZL and ER were investigated by ruthenium-ion-catalyzed oxidation (RICO) and Fourier transform infrared spectrometry. The pyrolytic reactivities of ZL and ER were examined with a thermogravimetric analyzer and Curie-point pyrolyzer–gas chromatograph/mass spectrometer. The results show that both ZL and ER are rich in −CH2CH2– and −CH2CH2CH2– bridged linkages connecting aromatic rings. In comparison to the RICO of ZL, the RICO of ER produced much less long-chain alkanoic and alkanedioic acids, suggesting that long alkylene bridges and alkyl side chains in ZL were largely cleaved via ethanolysis. Interestingly, ZL has a higher condensation degree than ER, which was confirmed by RICO and solid-state 13C nuclear magnetic resonance analysis. The result was explained by ethanolysis simulation of lignite-related model compounds using density functional theory. Thermogravimetric analysis of ZL and ER exhibits their different pyrolytic reactivities. According to analysis with a Curie-point pyrolyzer–gas chromatograph/mass spectrometer, significant differences in the distributions of the volatile species from the pyrolyses of ZL and ER were observed. Guaiacols and carbazoles are the most abundant group components from the pyrolyses of ZL and ER, respectively. ZL pyrolysis released much more alkanes and phenolic compounds than ER pyrolysis. The cleavage of Car–O bonds significantly proceeded during ZL ethanolysis.

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Section: Introductionmentioning

confidence: 99%

Effect of Ethanolysis on the Structure and Pyrolytic Reactivity of Zhaotong Lignite

Wei

Yan

et al. 2017

Energy Fuels

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“…The debate of asphaltene structure is one of the topics often discussed in the academic community, which goes through an understanding from an archipelago to an isolated island, and then to both. − The CID function of the FT-ICR MS provided critical information for this issue, but the important experiments were carried out with APPI. The ESI FT-ICR MS analysis on the composition of the RICO products had provided important information of the question of existing bridge structures in asphaltenes and how many they are . Zhou et al oxidized asphaltenes as well as aromatics and resins from various heavy oils into acids and found the diacids presented a very low concentration, which indicates that archipelago molecules cannot contribute a large portion of the studied asphaltenes.…”

Section: Characterization For Crude Oil and Its Fractionsmentioning

confidence: 99%

“…The ESI FT-ICR MS analysis on the composition of the RICO products had provided important information of the question of existing bridge structures in asphaltenes and how many they are. 211 Zhou et al 212 oxidized asphaltenes as well as aromatics and resins from various heavy oils into acids and found the diacids presented a very low concentration, which indicates that archipelago molecules cannot contribute a large portion of the studied asphaltenes.…”

Section: Characterization For Crude Oil and Its Fractionsmentioning

confidence: 99%

Molecular Characterization of Fossil and Alternative Fuels Using Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: Recent Advances and Perspectives

et al. 2021

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Molecular composition analysis of petroleum and alternative fuels has been considered as one of the greatest challenges in analytical chemistry. The rapid development of Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) has provided an opportunity to solve this problem. High mass resolution power and mass accuracy enable the separation of isobaric compounds in a complex mixture and assignment of their molecular composition. The combination of electrospray ionization (ESI) with FT-ICR MS achieves direct analysis of polar compounds in petroleum even if they are in trace amounts in the complex matrix. FT-ICR MS has made a great contribution to the chemical understanding of petroleum and alternative fuels; the relevant application is sometimes called “petroleomic analysis”. Hundreds of journal articles have been published over the past two decades using FT-ICR MS instruments to study the molecular composition of petroleum and alternative fuels, in which most of them used ESI as the ionization source. This review will present an overview of the studies regarding the petroleomic characterization of fossil and alternative fuels by FT-ICR MS coupled with ESI and a critical review of their main findings relevant to the chemical composition. Special features of this review are (1) covering the entire historical period; (2) focusing on ESI ionization; (3) a systematic review of the composition of almost all the components and compound classes, including but not limited to petroleum, coal-derived liquids, biofuels, and their distillates; asphaltenes, heavy residues, interfacial active substances; hydrocarbons and heteroatoms; and polar and nonpolar compounds. In addition, the challenges and further research directions will be proposed. This review focuses on the advances enabled by ultrahigh resolving power FT-ICR MS in a tribute to Professor Alan G. Marshall.

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“…This fact powerfully indicates that lignite could be oxidized to obtain BCAs. There are many oxidants such as O 2 [14], H 2 O 2 [15,16], RuO 4 [17,18] and NaOCl [19,20], among which NaOCl is widely adopted in the oxidative depolymerization of LRCs to prepare carboxylic acids due to its low cost, good reactivity and reusable electrolysis [21,22]. Shengli lignite [23] and Shenfu Subbituminous [24] were oxidized by NaOCl, respectively, and BCAs were detected in their resulting oxidation products.…”

Section: Introductionmentioning

confidence: 99%

Insight into Relationship between Thermal Dissolution of Low-Rank Coals and Their Subsequent Oxidative Depolymerization

et al. 2021

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Oxidative depolymerization of low-rank coals is promising for obtaining benzene carboxylic acids (BCAs). However, it is hindered by the low yield of BCAs along with a large number of alphatic acids. Thermal dissolution could modify the physico-chemical structural features of low-rank coals, which is expected to improve the oxidation of LRCs. In this paper, lignite and subbituminous coal were firstly subjected to thermal dissolution with cyclohexane at 250 °C for 2 h. Then, the raw coal and the corresponding thermal insoluble portion (TIP) were oxidized by NaOCl under the same conditions. The residual yields of TIPs oxidation were both lower than those of raw coals oxidation, indicating that TIPs were more easily oxidized than the raw coals. The yield of BCAs obtained by TIPs oxidation was above 19% higher than that from the oxidation of raw coals. Meanwhile, the selectivity of BCAs was improved in the resulting oxidation products from TIPs compared with that from the raw coals. The relationship between BCAs generation and thermal dissolution of low rank coals was investigated by ultimate analysis, Fourier transform infrared spectroscopy, and nitrogen adsorption-desorption analysis. The results suggested that thermal dissolution could enrich aromatic portion in the remaining TIPs, resulting in an increasing of the yield and selectivity of BCAs. Simultaneously, thermal dissolution raised the specific surface area and expanded the looser space structure of TIPS, which were beneficial for the sufficient collision between aromatic structures and oxidant, facilitating the oxidative depolymerization of TIPs. This investigation would provide a novel route for promoting BCAs production by mild oxidative depolymerization of low-rank coals.

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Ruthenium Ion-Catalyzed Oxidation for Petroleum Molecule Structural Features: A Review

Cited by 9 publications

References 81 publications

Effect of Ethanolysis on the Structure and Pyrolytic Reactivity of Zhaotong Lignite

Effect of Ethanolysis on the Structure and Pyrolytic Reactivity of Zhaotong Lignite

Molecular Characterization of Fossil and Alternative Fuels Using Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometry: Recent Advances and Perspectives

Insight into Relationship between Thermal Dissolution of Low-Rank Coals and Their Subsequent Oxidative Depolymerization

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