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Journal articles on the topic 'Alkane oxygenation'

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Author: Grafiati

Published: 9 March 2023

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1

Shul'pin, Georgiy B., Alexander E. Shilov, and Georg Süss-Fink. "Alkane oxygenation catalysed by gold complexes." Tetrahedron Letters 42, no. 41 (October 2001): 7253–56. http://dx.doi.org/10.1016/s0040-4039(01)01517-9.

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2

Shul'pin, Georgiy B. "Alkane Oxygenation with Hydrogen Peroxide Catalysed by Soluble Derivatives of Nickel and Platinum." Journal of Chemical Research 2002, no. 7 (July 2002): 351–53. http://dx.doi.org/10.3184/030823402103172257.

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Various alkanes can be oxidised by hydrogen peroxide in acetonitrile solution at 70°C if Ni(ClO4)2 (in the presence of 1,4,7-trimethyl-1,4,7-triazacyclononane) or H2PtCl6 are used as catalysts; whereas the nickel-catalysed reaction seems to proceed via attack of hydroxyl radicals on an alkane, the oxidation in the presence of platinum occurs possibly with participation of oxo or peroxo derivatives of this metal.

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3

Julsing, Mattijs K., Manfred Schrewe, Sjef Cornelissen, Inna Hermann, Andreas Schmid, and Bruno Bühler. "Outer Membrane Protein AlkL Boosts Biocatalytic Oxyfunctionalization of Hydrophobic Substrates in Escherichia coli." Applied and Environmental Microbiology 78, no. 16 (June 8, 2012): 5724–33. http://dx.doi.org/10.1128/aem.00949-12.

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ABSTRACTThe outer membrane of microbial cells forms an effective barrier for hydrophobic compounds, potentially causing an uptake limitation for hydrophobic substrates. Low bioconversion activities (1.9 U gcdw−1) have been observed for the ω-oxyfunctionalization of dodecanoic acid methyl ester by recombinantEscherichia colicontaining the alkane monooxygenase AlkBGT ofPseudomonas putidaGPo1. Using fatty acid methyl ester oxygenation as the model reaction, this study investigated strategies to improve bacterial uptake of hydrophobic substrates. Admixture of surfactants and cosolvents to improve substrate solubilization did not result in increased oxygenation rates. Addition of EDTA increased the initial dodecanoic acid methyl ester oxygenation activity 2.8-fold. The use of recombinantPseudomonas fluorescensCHA0 instead ofE. coliresulted in a similar activity increase. However, substrate mass transfer into cells was still found to be limiting. Remarkably, the coexpression of thealkLgene ofP. putidaGPo1 encoding an outer membrane protein with so-far-unknown function increased the dodecanoic acid methyl ester oxygenation activity of recombinantE. coli28-fold. In a two-liquid-phase bioreactor setup, a 62-fold increase to a maximal activity of 87 U gcdw−1was achieved, enabling the accumulation of high titers of terminally oxyfunctionalized products. Coexpression ofalkLalso increased oxygenation activities toward the natural AlkBGT substrates octane and nonane, showing for the first time clear evidence for a prominent role of AlkL in alkane degradation. This study demonstrates that AlkL is an efficient tool to boost productivities of whole-cell biotransformations involving hydrophobic aliphatic substrates and thus has potential for broad applicability.

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4

Shul’pin, Georgiy B., Tawan Sooknoi, Vladimir B. Romakh, Georg Süss-Fink, and Lidia S. Shul’pina. "Regioselective alkane oxygenation with H2O2 catalyzed by titanosilicalite TS-1." Tetrahedron Letters 47, no. 18 (May 2006): 3071–75. http://dx.doi.org/10.1016/j.tetlet.2006.03.009.

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5

Shul’pin, Georgiy B., Camilla C. Golfeto, Georg Süss-Fink, Lidia S. Shul’pina, and Dalmo Mandelli. "Alkane oxygenation with H2O2 catalysed by FeCl3 and 2,2′-bipyridine." Tetrahedron Letters 46, no. 27 (July 2005): 4563–67. http://dx.doi.org/10.1016/j.tetlet.2005.05.007.

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6

Company, Anna, Julio Lloret, Laura Gomez, and Miquel Costas. "ChemInform Abstract: Alkane C-H Oxygenation Catalyzed by Transition Metal Complexes." ChemInform 44, no. 11 (March 8, 2013): no. http://dx.doi.org/10.1002/chin.201311257.

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7

Sahoo, Prakash C., Amardeep Singh, Manoj Kumar, R. P. Gupta, D. Bhattacharyya, and S. S. V. Ramakumar. "Photosensitized biohybrid for terminal oxygenation of n-alkane to α, ω-dicarboxylic acids." Molecular Catalysis 535 (January 2023): 112889. http://dx.doi.org/10.1016/j.mcat.2022.112889.

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8

Barloy, Laurent, Pierrette Battioni, and Daniel Mansuy. "Manganese porphyrins supported on montmorillonite as hydrocarbon mono-oxygenation catalysts: particular efficacy for linear alkane hydroxylation." Journal of the Chemical Society, Chemical Communications, no. 19 (1990): 1365. http://dx.doi.org/10.1039/c39900001365.

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9

Guisado-Barrios, Gregorio, Alexandra M. Z. Slawin, and David T. Richens. "Iron complexes of new hydrophobic derivatives of tris(2-pyridylmethyl)amine: synthesis, characterization, and catalysis of alkane oxygenation by H2O2." Journal of Coordination Chemistry 63, no. 14-16 (July 20, 2010): 2642–58. http://dx.doi.org/10.1080/00958972.2010.506216.

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10

Sutradhar, Manas, Nikita V. Shvydkiy, M. Fátima C. Guedes da Silva, Marina V. Kirillova, Yuriy N. Kozlov, Armando J. L. Pombeiro, and Georgiy B. Shul'pin. "A new binuclear oxovanadium(v) complex as a catalyst in combination with pyrazinecarboxylic acid (PCA) for efficient alkane oxygenation by H2O2." Dalton Transactions 42, no. 33 (2013): 11791. http://dx.doi.org/10.1039/c3dt50584g.

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11

González-Núñez, María E., Jorge Royo, Rossella Mello, Minerva Báguena, Jaime Martínez Ferrer, Carmen Ramírez de Arellano, Gregorio Asensio, and G. K. Surya Prakash. "Oxygenation of Alkane C−H Bonds with Methyl(trifluoromethyl)dioxirane: Effect of the Substituents and the Solvent on the Reaction Rate." Journal of Organic Chemistry 70, no. 20 (September 2005): 7919–24. http://dx.doi.org/10.1021/jo0509511.

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12

Yamaguchi, Motowo, Hiroyuki Kousaka, Shinichi Izawa, Yoshiki Ichii, Takashi Kumano, Dai Masui, and Takamichi Yamagishi. "Syntheses, Characterization, and Catalytic Ability in Alkane Oxygenation of Chloro(dimethyl sulfoxide)ruthenium(II) Complexes with Tris(2-pyridylmethyl)amine and Its Derivatives1,2." Inorganic Chemistry 45, no. 20 (October 2006): 8342–54. http://dx.doi.org/10.1021/ic060722c.

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13

Forchetta, Mattia, Francesca Valentini, Valeria Conte, Pierluca Galloni, and Federica Sabuzi. "Photocatalyzed Oxygenation Reactions with Organic Dyes: State of the Art and Future Perspectives." Catalysts 13, no. 2 (January 18, 2023): 220. http://dx.doi.org/10.3390/catal13020220.

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Oxygen atom incorporation into organic molecules is one of the most powerful strategies to increase their pharmacological activity and to obtain valuable intermediates in organic synthesis. Traditional oxidizing agents perform very well, but their environmental impact and their low selectivity constitute significant limitations. On the contrary, visible-light-promoted oxygenations represent a sustainable method for oxidizing organic compounds, since only molecular oxygen and a photocatalyst are required. Therefore, photocatalytic oxygenation reactions exhibit very high atom-economy and eco-compatibility. This mini-review collects and analyzes the most recent literature on organo-photocatalysis applications to promote the selective oxygenation of organic substrates. In particular, acridinium salts, Eosin Y, Rose Bengal, cyano-arenes, flavinium salts, and quinone-based dyes are widely used as photocatalysts in several organic transformations as the oxygenations of alkanes, alkenes, alkynes, aromatic compounds, amines, phosphines, silanes, and thioethers. In this context, organo-photocatalysts proved to be highly efficient in catalytic terms, showing similar or even superior performances with respect to their metal-based counterparts, while maintaining a low environmental impact. In addition, given the mild reaction conditions, visible-light-promoted photo-oxygenation processes often display remarkable selectivity, which is a striking feature for the late-stage functionalization of complex organic molecules.

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14

Giusberti, L., F. Boscolo Galazzo, and E. Thomas. "Variability in climate and productivity during the Paleocene–Eocene Thermal Maximum in the western Tethys (Forada section)." Climate of the Past 12, no. 2 (February 9, 2016): 213–40. http://dx.doi.org/10.5194/cp-12-213-2016.

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Abstract. The Forada section (northeastern Italy) provides a continuous, expanded deep-sea record of the Paleocene–Eocene Thermal Maximum (PETM) in the central-western Tethys. We combine a new, high-resolution, benthic foraminiferal assemblage record with published calcareous plankton, mineralogical and biomarker data to document climatic and environmental changes across the PETM, highlighting the benthic foraminiferal extinction event (BEE). The onset of the PETM, occurring ∼ 30 kyr after a precursor event, is marked by a thin, black, barren clay layer, possibly representing a brief pulse of anoxia and carbonate dissolution. The BEE occurred within the 10 cm interval including this layer. During the first 3.5 kyr of the PETM, several agglutinated recolonizing taxa show rapid species turnover, indicating a highly unstable, CaCO3-corrosive environment. Calcareous taxa reappeared after this interval, and the next ∼9 kyr were characterized by rapid alternation of peaks in abundance of various calcareous and agglutinated recolonizers. These observations suggest that synergistic stressors, including deepwater CaCO3 corrosiveness, low oxygenation, and high environmental instability caused the extinction. Combined faunal and biomarker data (BIT index, higher plant n-alkane average chain length) and the high abundance of the mineral chlorite suggest that erosion and weathering increased strongly at the onset of the PETM, due to an overall wet climate with invigorated hydrological cycle, which led to storm flood events carrying massive sediment discharge into the Belluno Basin. This interval was followed by the core of the PETM, characterized by four precessionally paced cycles in CaCO3 %, hematite %, δ13C, abundant occurrence of opportunistic benthic foraminiferal taxa, and calcareous nannofossil and planktonic foraminiferal taxa typical of high-productivity environments, radiolarians, and lower δDn-alkanes. We interpret these cycles as reflecting alternation between an overall arid climate, characterized by strong winds and intense upwelling, and an overall humid climate, with abundant rains and high sediment delivery (including refractory organic carbon) from land. Precessionally paced marl–limestone couplets occur throughout the recovery interval of the carbon isotope excursion (CIE) and up to 10 m above it, suggesting that these wet–dry cycles persisted, though at declining intensity, after the peak PETM. Enhanced climate extremes at mid-latitudes might have been a direct response to the massive CO2 input in the ocean atmosphere system at the Paleocene–Eocene transition, and may have had a primary role in restoring the Earth system to steady state.

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15

Giusberti, L., F. Boscolo Galazzo, and E. Thomas. "Benthic foraminifera at the Paleocene/Eocene thermal maximum in the western Tethys (Forada section): variability in climate and productivity." Climate of the Past Discussions 11, no. 5 (September 4, 2015): 4205–72. http://dx.doi.org/10.5194/cpd-11-4205-2015.

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Abstract. The Forada section (northeastern Italy) provides a continuous, expanded deep-sea record of the Paleocene/Eocene thermal maximum (PETM) in the central-western Tethys. We combine a new, high resolution, benthic foraminiferal assemblage record with published calcareous plankton, mineralogical and biomarker data to document climatic and environmental changes across the PETM, highlighting the benthic foraminiferal extinction event (BEE). The onset of the PETM, occurring ~ 30 kyr after a precursor event, is marked by a thin, black, barren clay layer, possibly representing a brief pulse of anoxia and carbonate dissolution. The BEE occurred within the 10 cm interval including this layer. During the first 3.5 kyr of the PETM several agglutinated recolonizing taxa show rapid species turnover, indicating a highly unstable, CaCO3-corrosive environment. Calcareous taxa reappeared after this interval, and the next ~ 9 kyr were characterized by rapid alternation of peaks in abundance of various calcareous and agglutinant recolonizers. These observations suggest that synergistic stressors including deep water CaCO3-corrosiveness, low oxygenation, and high environmental instability caused the extinction. Combined faunal and biomarker data (BIT index, higher plant n-alkane average chain length) and the high abundance of the mineral chlorite suggest that erosion and weathering increased strongly at the onset of the PETM, due to an overall wet climate with invigorated hydrological cycle, which led to storm flood-events carrying massive sediment discharge into the Belluno Basin. This interval was followed by the core of the PETM, characterized by four precessionally paced cycles in CaCO3%, hematite%, δ13C, abundant occurrence of opportunistic benthic foraminiferal taxa, as well as calcareous nannofossil and planktonic foraminiferal taxa typical of high productivity environments, radiolarians, and lower δDn-alkanes. We interpret these cycles as reflecting alternation between an overall arid climate, characterized by strong winds and intense upwelling, with an overall humid climate, with abundant rains and high sediment delivery (including refractory organic carbon) from land. Precessionally paced marl-limestone couplets occur throughout the recovery interval of the CIE and up to ten meters above it, suggesting that these wet-dry cycles persisted, though at declining intensity, after the peak PETM. Enhanced climate extremes at mid-latitudes might have been a direct response to the massive CO2 input in the ocean atmosphere system at the Paleocene–Eocene transition, and may have had a primary role in restoring the Earth system to steady state.

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16

Fisher, Evgeniy, Aleksandr Urakov, Milena Svetova, Darya Suntsova, and Ilnur Yagudin. "Covid-19: Intrapulmonary alkaline hydrogen peroxide can immediately increase blood oxygenation." Medicinski casopis 55, no. 4 (2021): 135–38. http://dx.doi.org/10.5937/mckg55-35424.

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It has been shown that the new coronavirus infection is life-threatening for patients not because of the COVID-19 virus, but because of the complications it causes. The most dangerous complication of this disease is the airway obstruction syndrome, which occurs with atypical pneumonia. Blockage of the airways occurs due to the accumulation of excessively large amounts of mucus and pus in them and swelling of the lung tissue, so ventilation of the lungs with air becomes almost impossible. The sad outcome of respiratory obstruction is hypoxia and hypoxic brain damage. Under these conditions, extracorporeal membrane oxygenation remains the only known way to increase blood oxygenation. However, in 2021, it was shown that intra-pulmonary administration of a warm alkaline solution of hydrogen peroxide immediately turns mucus and pus into oxygen foam and increases blood oxygen saturation. The proposed technology is a new variant of emergency blood oxygenation in severe suffocation caused by blockage of the respiratory tract with mucus, pus and blood.

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17

Liu, Zhenghui, Peng Wang, Hualin Ou, Zhenzhong Yan, Suqing Chen, Xingxing Tan, Dongkun Yu, Xinhui Zhao, and Tiancheng Mu. "Preparation of cyclic imides from alkene-tethered amides: application of homogeneous Cu(ii) catalytic systems." RSC Advances 10, no. 13 (2020): 7698–707. http://dx.doi.org/10.1039/c9ra10422d.

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18

Nizova, G. V., and G. B. Shul'pin. "Aerobic photochemical oxygenation of alkanes sensitized by pyrazine derivatives." Russian Chemical Bulletin 44, no. 10 (October 1995): 1982–83. http://dx.doi.org/10.1007/bf00707250.

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19

Ghosh, Ivy, Biswarup Chakraborty, Abhijit Bera, Satadal Paul, and Tapan Kanti Paine. "Selective oxygenation of C–H and CC bonds with H₂O₂ by high-spin cobalt(ii)-carboxylate complexes." Dalton Transactions 51, no. 6 (2022): 2480–92. http://dx.doi.org/10.1039/d1dt02235k.

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Cobalt(ii)–carboxylate complexes of the 6-Me3-TPA ligand in combination with hydrogen peroxide perform the oxygenation of aliphatic C–H bonds of alkanes and epoxidation of alkenes with high chemo- and stereo-selectivity. A metal-based oxidant is proposed as the active oxidant.

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20

Shul’pin, Georgiy B., Georg Süss-Fink, and Lidia S. Shul’pina. "Oxygenation of alkanes with hydrogen peroxide catalysed by osmium complexes." Chemical Communications, no. 13 (2000): 1131–32. http://dx.doi.org/10.1039/b002015j.

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21

Grinstaff, M., M. Hill, J. Labinger, and H. Gray. "Mechanism of catalytic oxygenation of alkanes by halogenated iron porphyrins." Science 264, no. 5163 (May 27, 1994): 1311–13. http://dx.doi.org/10.1126/science.8191283.

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22

Xu, Xiaohe, Jian Sun, Yuyan Lin, Jingya Cheng, Pingping Li, Yiyan Yan, Qi Shuai, and Yuanyuan Xie. "Copper nitrate-catalyzed oxidative coupling of unactivated C(sp3)–H bonds of ethers and alkanes with N-hydroxyphthalimide: synthesis of N-hydroxyimide esters." Organic & Biomolecular Chemistry 15, no. 46 (2017): 9875–79. http://dx.doi.org/10.1039/c7ob02249b.

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23

Olmedo, Andrés, Carmen Aranda, José C. del Río, Jan Kiebist, Katrin Scheibner, Angel T. Martínez, and Ana Gutiérrez. "From Alkanes to Carboxylic Acids: Terminal Oxygenation by a Fungal Peroxygenase." Angewandte Chemie International Edition 55, no. 40 (August 30, 2016): 12248–51. http://dx.doi.org/10.1002/anie.201605430.

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24

Olmedo, Andrés, Carmen Aranda, José C. del Río, Jan Kiebist, Katrin Scheibner, Angel T. Martínez, and Ana Gutiérrez. "From Alkanes to Carboxylic Acids: Terminal Oxygenation by a Fungal Peroxygenase." Angewandte Chemie 128, no. 40 (August 30, 2016): 12436–39. http://dx.doi.org/10.1002/ange.201605430.

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25

Liebov, Nichole S., Jonathan M. Goldberg, Nicholas C. Boaz, Nathan Coutard, Steven E. Kalman, Thompson Zhuang, John T. Groves, and T. Brent Gunnoe. "Selective Photo‐Oxygenation of Light Alkanes Using Iodine Oxides and Chloride." ChemCatChem 11, no. 20 (September 25, 2019): 5045–54. http://dx.doi.org/10.1002/cctc.201901175.

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26

Yamanaka, Ichiro, Takashi Akimoto, and Kiyoshi Otsuka. "Europium-Catalysis for the Mono-Oxygenation of Alkanes in the Liquid Phase." Chemistry Letters 23, no. 8 (August 1994): 1511–14. http://dx.doi.org/10.1246/cl.1994.1511.

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27

Mizuno, Noritaka, Masaki Tateishi, To-oru Hirose, and Masakazu Iwamoto. "Oxygenation of Alkanes by Molecular Oxygen on [PW9O37{Fe2Ni(OAc)3}]10−Heteropolyanion." Chemistry Letters 22, no. 12 (December 1993): 2137–40. http://dx.doi.org/10.1246/cl.1993.2137.

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28

Somekh, Miriam, Alexander M. Khenkin, Adi Herman, and Ronny Neumann. "Selective Visible Light Aerobic Photocatalytic Oxygenation of Alkanes to the Corresponding Carbonyl Compounds." ACS Catalysis 9, no. 9 (August 13, 2019): 8819–24. http://dx.doi.org/10.1021/acscatal.9b02999.

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29

Okamoto, Takanobu, Shinsuke Takagi, Tsutomu Shiragami, and Haruo Inoue. "Efficient Oxygenation of Alkene through Reductive Quenching of Excited Sb(V)tetraphenylporphyrin by Triphenylphosphine." Chemistry Letters 22, no. 4 (April 1993): 687–90. http://dx.doi.org/10.1246/cl.1993.687.

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30

Ohkubo, Kei, Takashi Nanjo, and Shunichi Fukuzumi. "Efficient Photocatalytic Oxygenation of Aromatic Alkene to 1,2-Dioxetane with Oxygen via Electron Transfer." Organic Letters 7, no. 19 (September 2005): 4265–68. http://dx.doi.org/10.1021/ol051696+.

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31

Otsuka, Kiyoshi, and Ichiro Yamanaka. "Oxygenation of alkanes and aromatics by reductively activated oxygen during H2–O2 cell reactions." Catalysis Today 57, no. 1-2 (March 2000): 71–86. http://dx.doi.org/10.1016/s0920-5861(99)00310-7.

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32

Reis, Patrícia M., José Armando, L. Silva, João J. R. Fraústo da Silva, and Armando J. L. Pombeiro. "Amavadine as a catalyst for the peroxidative halogenation, hydroxylation and oxygenation of alkanes and benzene." Chemical Communications, no. 19 (2000): 1845–46. http://dx.doi.org/10.1039/b005513l.

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33

Aukema, Kelly G., Thomas M. Makris, Sebastian A. Stoian, Jack E. Richman, Eckard Münck, John D. Lipscomb, and Lawrence P. Wackett. "Cyanobacterial Aldehyde Deformylase Oxygenation of Aldehydes Yieldsn– 1 Aldehydes and Alcohols in Addition to Alkanes." ACS Catalysis 3, no. 10 (September 11, 2013): 2228–38. http://dx.doi.org/10.1021/cs400484m.

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34

López-Linares, Francisco, Oscar Colmenares, Edgar Catarí, and Arquímedes Karam. "Oxygenation of aromatic substrates over Pd(II) catalysts bearing bis(pyrazol-1-yl)alkanes ligands." Reaction Kinetics and Catalysis Letters 85, no. 1 (May 2005): 139–44. http://dx.doi.org/10.1007/s11144-005-0253-y.

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35

Shul'pin, Georgiy B, Galina V Nizova, Yuriy N Kozlov, Laura Gonzalez Cuervo, and Georg Süss-Fink. "Hydrogen Peroxide Oxygenation of Alkanes Including Methane and Ethane Catalyzed by Iron Complexes in Acetonitrile." Advanced Synthesis & Catalysis 346, no. 23 (February 2004): 317–32. http://dx.doi.org/10.1002/adsc.200303147.

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36

Malek, Belaid, Ashwini A. Ghogare, Rajib Choudhury, and Alexander Greer. "Air–water interface effects on the regioselectivity of singlet oxygenations of a trisubstituted alkene." Tetrahedron Letters 56, no. 30 (July 2015): 4505–8. http://dx.doi.org/10.1016/j.tetlet.2015.05.111.

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37

Poschner, Thomas, Anne-Kristin Schaefer, Doris Hutschala, Georg Goliasch, Julia Riebandt, Klaus Distelmaier, Martin H. Bernardi, et al. "Impact of Venoarterial Extracorporeal Membrane Oxygenation on Alkaline Phosphatase Metabolism after Cardiac Surgery." Biomolecules 11, no. 5 (May 17, 2021): 748. http://dx.doi.org/10.3390/biom11050748.

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(1) Alkaline phosphatase (AP) is consumed during cardiopulmonary bypass (CPB). A high AP depletion leads to an impaired outcome after cardiac surgery. However, data is scarce on the postoperative course of AP under venoarterial ECMO (VA-ECMO) support. (2) A total of 239 patients with VA-ECMO support between 2000 and 2019 at the Department of Cardiac Surgery (Vienna General Hospital, Austria) were included in this retrospective analysis. Blood samples were collected at several timepoints (baseline, postoperative day (POD) 1–7, POD 14 and 30). Patients were categorized according to the relative AP drop (<60% vs. ≥60%) and ECMO duration (<5 days vs. ≥5 days). (3) Overall, 44.4% reached the baseline AP values within 5 days—this was only the case for 28.6% with a higher AP drop (compared to 62.7% with a lower drop; p = 0.000). A greater AP drop was associated with a significantly higher need for renal replacement therapy (40.9% vs. 61.9%; p = 0.002) and an impaired 1-year survival (51.4% vs. 66.0%; p = 0.031). (4) CPB exceeds the negative impact of VA-ECMO; still, ECMO seems to delay alkaline phosphatase recovery. A greater initial AP drop bears the risk of higher morbidity and mortality.

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38

Inoue, Haruo, Shigeaki Funyu, Yutaka Shimada, and Shinsuke Takagi. "Artificial photosynthesis via two-electron conversion: Photochemical oxygenation sensitized by ruthenium porphyrins with water as both electron and oxygen atom donor." Pure and Applied Chemistry 77, no. 6 (January 1, 2005): 1019–33. http://dx.doi.org/10.1351/pac200577061019.

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Recent progress in the field of artificial photosynthesis is reviewed. Among various approaches to oxidizing the water molecule, attention has been focused on the two-electron chemical conversion processes mediated by metallo-porphyrins upon visible light irradiation. Photochemical oxygenation reactions such as the epoxidation of alkenes sensitized by ruthenium(II) porphyrins with water as both electron and oxygen atom donor have been found. Ru porphyrin induces highly efficient two-electron oxidation of water with a quantum yield of 60 % to form an epoxide from the alkene with high selectivity. The water molecule serves as both an efficient electron and oxygen atom donor in the reaction, in which the oxygen atom of water is incorporated in a useful product, i.e., epoxide.

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39

Scheller, Ulrich, Thomas Zimmer, Dörte Becher, Frieder Schauer, and Wolf-Hagen Schunck. "Oxygenation Cascade in Conversion ofn-Alkanes to α,ω-Dioic Acids Catalyzed by Cytochrome P450 52A3." Journal of Biological Chemistry 273, no. 49 (December 4, 1998): 32528–34. http://dx.doi.org/10.1074/jbc.273.49.32528.

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40

Otsuka, K., and I. Yamanaka. "ChemInform Abstract: Oxygenation of Alkanes and Aromatics by Reductively Activated Oxygen During H2-O2 Cell Reactions." ChemInform 31, no. 31 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200031282.

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41

OKAMOTO, T., S. TAKAGI, T. SHIRAGAMI, and H. INOUE. "ChemInform Abstract: Efficient Oxygenation of Alkene Through Reductive Quenching of Excited Sb(V) Tetraphenylporphyrin by Triphenylphosphine." ChemInform 24, no. 52 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199352136.

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42

Wan, Jie-Ping, Yong Gao, and Li Wei. "Recent Advances in Transition-Metal-Free Oxygenation of Alkene C=C Double Bonds for Carbonyl Generation." Chemistry - An Asian Journal 11, no. 15 (June 27, 2016): 2092–102. http://dx.doi.org/10.1002/asia.201600671.

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43

NAM, W., S. J. YANG, and H. KIM. "ChemInform Abstract: Catalytic Oxygenation of Alkenes and Alkanes by Oxygen Donors Catalyzed by Cobalt-Substituted Polyoxotungstate." ChemInform 28, no. 4 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199704075.

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Aleo, M. D., and R. G. Schnellmann. "Regulation of glycolytic metabolism during long-term primary culture of renal proximal tubule cells." American Journal of Physiology-Renal Physiology 262, no. 1 (January 1, 1992): F77—F85. http://dx.doi.org/10.1152/ajprenal.1992.262.1.f77.

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Adequate oxygenation was a major factor regulating the induction of glycolytic metabolism in primary cultures of rabbit renal proximal tubule cells during short-term (less than 1 day) and long-term (1-7 day) culture. As measured by cellular lactate content, glucose consumption, and lactate dehydrogenase activity, less glycolytic metabolism was induced in cultured cells that were constantly aerated than in cells that were held stationary. When oxidative metabolism is supported by providing 2-10 mM heptanoate (HEP) as a metabolic substrate glycolytic metabolism further decreased during short-term, but not long-term culture. Cellular proliferation did not play a major role in regulating the induction of glycolytic metabolism, since glycolytic metabolism increased before cell growth had occurred, did not decline once logarithmic cell growth had ceased, and was stimulated less by cell growth than by inadequate oxygenation. Fructose-1,6-bisphosphatase and alkaline phosphatase, representative markers of gluconeogenic and brush-border membrane enzyme activities, respectively, declined during culture regardless of culture conditions or the presence of HEP. Therefore, glycolytic metabolism can be effectively minimized by constantly aerating cultured proximal tubule cells and can be further reduced by the addition of HEP during short-term culture.

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Sanyal, Indrajit, Narasappa Narasimha Murthy, and Kenneth D. Karlin. "A dicopper(I) complex and its oxygenation chemistry using a dinucleating ligand with a pendant alkene group." Inorganic Chemistry 32, no. 23 (November 1993): 5330–37. http://dx.doi.org/10.1021/ic00075a061.

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Mizuno, Noritaka, Chika Nozaki, Ikuro Kiyoto, and Makoto Misono. "Highly Efficient Utilization of Hydrogen Peroxide for Selective Oxygenation of Alkanes Catalyzed by Diiron-Substituted Polyoxometalate Precursor." Journal of the American Chemical Society 120, no. 36 (September 1998): 9267–72. http://dx.doi.org/10.1021/ja980006c.

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Reis, Patricia M., Jose Armando L. Silva, Joao J. R. Frausto da Silva, and Armando J. L. Pombeiro. "ChemInform Abstract: Amavadine as a Catalyst for the Peroxidative Halogenation, Hydroxylation and Oxygenation of Alkanes and Benzene." ChemInform 32, no. 1 (January 2, 2001): no. http://dx.doi.org/10.1002/chin.200101032.

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Aeppli, Christoph, Robert K. Nelson, Catherine A. Carmichael, David L. Valentine, and Christopher M. Reddy. "BIOTIC AND ABIOTIC OIL DEGRADATION AFTER THE DEEPWATER HORIZON DISASTER LEADS TO FORMATION OF RECALCITRANT OXYGENATED HYDROCARBONS: NEW INSIGHTS USING GC×GC." International Oil Spill Conference Proceedings 2014, no. 1 (May 1, 2014): 1087–98. http://dx.doi.org/10.7901/2169-3358-2014.1.1087.

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ABSTRACT We found that biodegradation, as well as photooxidation, of Macondo well (MW) oil led to rapid formation of recalcitrant oxygenated hydrocarbons (OxHC) after the Deepwater Horizon disaster. These compounds, which appear to be an abundant product of natural oil degradation, are poorly characterized in terms of molecular composition. We used various bulk and molecular techniques to characterize the OxHC fraction of weathered MW oil. Furthermore, we compared the characteristic disappearance of various petroleum hydrocarbons to gain insights into on-going biotic, as well as abiotic, oil oxygenation processes, that ultimately determine the fate of petroleum hydrocarbons in the environment. We found that biodegradation as well as photooxidation was responsible for the observed degradation of alkanes and PAHs in MW oil. Furthermore, we identified labile as well as recalcitrant biomarker compounds; these labile biomarker compounds should be used with caution for oil fingerprinting.

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Lelario, Filomena, Giuliana Bianco, Sabino Aurelio Bufo, and Laura Scrano. "Simulated Ageing of Crude Oil and Advanced Oxidation Processes for Water Remediation since Crude Oil Pollution." Catalysts 11, no. 8 (August 10, 2021): 954. http://dx.doi.org/10.3390/catal11080954.

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Crude oil can undergo biotic and abiotic transformation processes in the environment. This article deals with the fate of an Italian crude oil under simulated solar irradiation to understand (i) the modification induced on its composition by artificial ageing and (ii) the transformations arising from different advanced oxidation processes (AOPs) applied as oil-polluted water remediation methods. The AOPs adopted were photocatalysis, sonolysis and, simultaneously, photocatalysis and sonolysis (sonophotocatalysis). Crude oil and its water-soluble fractions underwent analysis using GC-MS, liquid-state 1H-NMR, Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS), and fluorescence. The crude oil after light irradiation showed (i) significant modifications induced by the artificial ageing on its composition and (ii) the formation of potentially toxic substances. The treatment produced oil oxidation with a particular effect of double bonds oxygenation. Non-polar compounds present in the water-soluble oil fraction showed a strong presence of branched alkanes and a good amount of linear and aromatic alkanes. All remediation methods utilised generated an increase of C5 class and a decrease of C6–C9 types of compounds. The analysis of polar molecules elucidated that oxygenated compounds underwent a slight reduction after photocatalysis and a sharp decline after sonophotocatalytic degradation. Significant modifications did not occur by sonolysis.

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Yamaguchi, Motowo, Takashi Kumano, Dai Masui, and Takamichi Yamagishi. "Photoassisted oxygenation of alkane catalyzed by ruthenium complexes using 2,6-dichloropyridine N-oxide under visible light irradiationElectronic supplementary information (ESI) available: syntheses of the complexes, crystallographic data of complex 4 (Table S-1), 1H NMR spectra before and after irradiation (Fig. S-1, S-2, S-3, S-5), UV-vis spectral change (Fig. S-4, S-6). See http://www.rsc.org/suppdata/cc/b3/b316970g/." Chemical Communications, no. 7 (2004): 798. http://dx.doi.org/10.1039/b316970g.

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