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Journal articles on the topic 'Alkane Oxidation'

Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

van Beilen, Jan B., Martin Neuenschwander, Theo H. M. Smits, Christian Roth, Stefanie B. Balada, and Bernard Witholt. "Rubredoxins Involved in Alkane Oxidation." Journal of Bacteriology 184, no. 6 (March 15, 2002): 1722–32. http://dx.doi.org/10.1128/jb.184.6.1722-1732.2002.

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ABSTRACT Rubredoxins (Rds) are essential electron transfer components of bacterial membrane-bound alkane hydroxylase systems. Several Rd genes associated with alkane hydroxylase or Rd reductase genes were cloned from gram-positive and gram-negative organisms able to grow on n-alkanes (Alk-Rds). Complementation tests in an Escherichia coli recombinant containing all Pseudomonas putida GPo1 genes necessary for growth on alkanes except Rd 2 (AlkG) and sequence comparisons showed that the Alk-Rds can be divided in AlkG1- and AlkG2-type Rds. All alkane-degrading strains contain AlkG2-type Rds, which are able to replace the GPo1 Rd 2 in n-octane hydroxylation. Most strains also contain AlkG1-type Rds, which do not complement the deletion mutant but are highly conserved among gram-positive and gram-negative bacteria. Common to most Rds are the two iron-binding CXXCG motifs. All Alk-Rds possess four negatively charged residues that are not conserved in other Rds. The AlkG1-type Rds can be distinguished from the AlkG2-type Rds by the insertion of an arginine downstream of the second CXXCG motif. In addition, the glycines in the two CXXCG motifs are usually replaced by other amino acids. Mutagenesis of residues conserved in either the AlkG1- or the AlkG2-type Rds, but not between both types, shows that AlkG1 is unable to transfer electrons to the alkane hydroxylase mainly due to the insertion of the arginine, whereas the exchange of the glycines in the two CXXCG motifs only has a limited effect.

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2

HAGGIN, JOSEPH. "ALKANE PARTIAL OXIDATION." Chemical & Engineering News 74, no. 12 (March 18, 1996): 6–7. http://dx.doi.org/10.1021/cen-v074n012.p006.

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3

Du, Wenzhou, Yue Wang, Xuelin Liu, and Lulu Sun. "Study on Low Temperature Oxidation Characteristics of Oil Shale Based on Temperature Programmed System." Energies 11, no. 10 (September 29, 2018): 2594. http://dx.doi.org/10.3390/en11102594.

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Oil shale is a kind of high-combustion heat mineral, and its oxidation in mining and storage are worth studying. To investigate the low-temperature oxidation characteristics of oil shale, the temperature, CO, alkane and alkene gases were analyzed using a temperature-programmed device. The results showed that the temperature of oil shale underwent three oxidation stages, namely a slow low-temperature oxidation stage, a rapid temperature-increasing oxidation stage, and a steady temperature-increasing stage. The higher the air supply rate is, the higher the crossing point temperature is. Similar to coal, CO also underwent three stages, namely a slow low-temperature oxidation stage, a rapid oxidation stage, and a steady increase stage. However, unlike coal, alkane and alkene gases produced by oil shale underwent four stages. They all had a concentration reduction stage with the maximum drop of 24.20%. Statistical classification of inflection temperature of various gases as their concentrations change showed that the temperature of 140 °C is the key temperature for group reactions, and above the temperature of 140 °C, all alkane and alkene gases underwent the rapid concentration increase stage.

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4

Centi, G. "Selective heterogeneous oxidation of light alkanes. What differentiates alkane from alkene feedstocks?" Catalysis Letters 22, no. 1-2 (March 1993): 53–66. http://dx.doi.org/10.1007/bf00811769.

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5

Nagababu, Penumaka, Steve S. F. Yu, Suman Maji, Ravirala Ramu, and Sunney I. Chan. "Developing an efficient catalyst for controlled oxidation of small alkanes under ambient conditions." Catal. Sci. Technol. 4, no. 4 (2014): 930–35. http://dx.doi.org/10.1039/c3cy00884c.

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Catalysis of alkane oxidation by a tricopper complex. The tricopper complex can mediate efficient conversion of small alkanes to their corresponding alcohols without over oxidation under ambient conditions.

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6

Marı́n, Mercedes M., Theo H. M. Smits, Jan B. van Beilen, and Fernando Rojo. "The Alkane Hydroxylase Gene of Burkholderia cepacia RR10 Is under Catabolite Repression Control." Journal of Bacteriology 183, no. 14 (July 15, 2001): 4202–9. http://dx.doi.org/10.1128/jb.183.14.4202-4209.2001.

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ABSTRACT In many microorganisms the first step for alkane degradation is the terminal oxidation of the molecule by an alkane hydroxylase. We report the characterization of a gene coding for an alkane hydroxylase in aBurkholderia cepacia strain isolated from an oil-contaminated site. The protein encoded showed similarity to other known or predicted bacterial alkane hydroxylases, although it clustered on a separate branch together with the predicted alkane hydroxylase of a Mycobacterium tuberculosis strain. Introduction of the cloned B. cepacia gene into an alkane hydroxylase knockout mutant of Pseudomonas fluorescens CHAO restored its ability to grow on alkanes, which confirms that the gene analyzed encodes a functional alkane hydroxylase. The gene, which was namedalkB, is not linked to other genes of the alkane oxidation pathway. Its promoter was identified, and its expression was analyzed under different growth conditions. Transcription was induced by alkanes of chain lengths containing 12 to at least 30 carbon atoms as well as by alkanols. Although the gene was efficiently expressed during exponential growth, transcription increased about fivefold when cells approached stationary phase, a characteristic not shared by the few alkane degraders whose regulation has been studied. Expression of the alkB gene was under carbon catabolite repression when cells were cultured in the presence of several organic acids and sugars or in a complex (rich) medium. The catabolic repression process showed several characteristics that are clearly different from what has been observed in other alkane degradation pathways.

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7

Hamamura, Natsuko, Chris M. Yeager, and Daniel J. Arp. "Two Distinct Monooxygenases for Alkane Oxidation inNocardioides sp. Strain CF8." Applied and Environmental Microbiology 67, no. 11 (November 1, 2001): 4992–98. http://dx.doi.org/10.1128/aem.67.11.4992-4998.2001.

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ABSTRACT Alkane monooxygenases in Nocardioides sp. strain CF8 were examined at the physiological and genetic levels. Strain CF8 can utilize alkanes ranging in chain length from C2 to C16. Butane degradation by butane-grown cells was strongly inhibited by allylthiourea, a copper-selective chelator, while hexane-, octane-, and decane-grown cells showed detectable butane degradation activity in the presence of allylthiourea. Growth on butane and hexane was strongly inhibited by 1-hexyne, while 1-hexyne did not affect growth on octane or decane. A specific 30-kDa acetylene-binding polypeptide was observed for butane-, hexane-, octane-, and decane-grown cells but was absent from cells grown with octane or decane in the presence of 1-hexyne. These results suggest the presence of two monooxygenases in strain CF8. Degenerate primers designed for PCR amplification of genes related to the binuclear-iron-containing alkane hydroxylase fromPseudomonas oleovorans were used to clone a related gene from strain CF8. Reverse transcription-PCR and Northern blot analysis showed that this gene encoding a binuclear-iron-containing alkane hydroxylase was expressed in cells grown on alkanes above C6. These results indicate the presence of two distinct monooxygenases for alkane oxidation in Nocardioides sp. strain CF8.

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8

Bruheim, Per, Harald Bredholt, and Kjell Eimhjellen. "Effects of Surfactant Mixtures, Including Corexit 9527, on Bacterial Oxidation of Acetate and Alkanes in Crude Oil." Applied and Environmental Microbiology 65, no. 4 (April 1, 1999): 1658–61. http://dx.doi.org/10.1128/aem.65.4.1658-1661.1999.

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ABSTRACT Mixtures of nonionic and anionic surfactants, including Corexit 9527, were tested to determine their effects on bacterial oxidation of acetate and alkanes in crude oil by cells pregrown on these substrates. Corexit 9527 inhibited oxidation of the alkanes in crude oil byAcinetobacter calcoaceticus ATCC 31012, while Span 80, a Corexit 9527 constituent, markedly increased the oil oxidation rate. Another Corexit 9527 constituent, the negatively charged dioctyl sulfosuccinate (AOT), strongly reduced the oxidation rate. The combination of Span 80 and AOT increased the rate, but not as much as Span 80 alone increased it, which tentatively explained the negative effect of Corexit 9527. The results of acetate uptake and oxidation experiments indicated that the nonionic surfactants interacted with the acetate uptake system while the anionic surfactant interacted with the oxidation system of the bacteria. The overall effect of Corexit 9527 on alkane oxidation by A. calcoaceticus ATCC 31012 thus seems to be the sum of the independent effects of the individual surfactants in the surfactant mixture. When Rhodococcus sp. strain 094 was used, the alkane oxidation rate decreased to almost zero in the presence of a mixture of Tergitol 15-S-7 and AOT even though the Tergitol 15-S-7 surfactant increased the alkane oxidation rate and AOT did not affect it. This indicated that there was synergism between the two surfactants rather than an additive effect like that observed forA. calcoaceticus ATCC 31012.

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9

Shul’pin, Georgiy B., Yuriy N. Kozlov, and Lidia S. Shul’pina. "Metal Complexes Containing Redox-Active Ligands in Oxidation of Hydrocarbons and Alcohols: A Review." Catalysts 9, no. 12 (December 9, 2019): 1046. http://dx.doi.org/10.3390/catal9121046.

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Ligands are innocent when they allow oxidation states of the central atoms to be defined. A noninnocent (or redox) ligand is a ligand in a metal complex where the oxidation state is not clear. Dioxygen can be a noninnocent species, since it exists in two oxidation states, i.e., superoxide (O2−) and peroxide (O22−). This review is devoted to oxidations of C–H compounds (saturated and aromatic hydrocarbons) and alcohols with peroxides (hydrogen peroxide, tert-butyl hydroperoxide) catalyzed by complexes of transition and nontransition metals containing innocent and noninnocent ligands. In many cases, the oxidation is induced by hydroxyl radicals. The mechanisms of the formation of hydroxyl radicals from H2O2 under the action of transition (iron, copper, vanadium, rhenium, etc.) and nontransition (aluminum, gallium, bismuth, etc.) metal ions are discussed. It has been demonstrated that the participation of the second hydrogen peroxide molecule leads to the rapture of O–O bond, and, as a result, to the facilitation of hydroxyl radical generation. The oxidation of alkanes induced by hydroxyl radicals leads to the formation of relatively unstable alkyl hydroperoxides. The data on regioselectivity in alkane oxidation allowed us to identify an oxidizing species generated in the decomposition of hydrogen peroxide: (hydroxyl radical or another species). The values of the ratio-of-rate constants of the interaction between an oxidizing species and solvent acetonitrile or alkane gives either the kinetic support for the nature of the oxidizing species or establishes the mechanism of the induction of oxidation catalyzed by a concrete compound. In the case of a bulky catalyst molecule, the ratio of hydroxyl radical attack rates upon the acetonitrile molecule and alkane becomes higher. This can be expanded if we assume that the reactions of hydroxyl radicals occur in a cavity inside a voluminous catalyst molecule, where the ratio of the local concentrations of acetonitrile and alkane is higher than in the whole reaction volume. The works of the authors of this review in this field are described in more detail herein.

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10

Cooley, Richard B., Bradley L. Dubbels, Luis A. Sayavedra-Soto, Peter J. Bottomley, and Daniel J. Arp. "Kinetic characterization of the soluble butane monooxygenase from Thauera butanivorans, formerly ‘Pseudomonas butanovora’." Microbiology 155, no. 6 (June 1, 2009): 2086–96. http://dx.doi.org/10.1099/mic.0.028175-0.

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Soluble butane monooxygenase (sBMO), a three-component di-iron monooxygenase complex expressed by the C2–C9 alkane-utilizing bacterium Thauera butanivorans, was kinetically characterized by measuring substrate specificities for C1–C5 alkanes and product inhibition profiles. sBMO has high sequence homology with soluble methane monooxygenase (sMMO) and shares a similar substrate range, including gaseous and liquid alkanes, aromatics, alkenes and halogenated xenobiotics. Results indicated that butane was the preferred substrate (defined by k cat : K m ratios). Relative rates of oxidation for C1–C5 alkanes differed minimally, implying that substrate specificity is heavily influenced by differences in substrate K m values. The low micromolar K m for linear C2–C5 alkanes and the millimolar K m for methane demonstrate that sBMO is two to three orders of magnitude more specific for physiologically relevant substrates of T. butanivorans. Methanol, the product of methane oxidation and also a substrate itself, was found to have similar K m and k cat values to those of methane. This inability to kinetically discriminate between the C1 alkane and C1 alcohol is observed as a steady-state concentration of methanol during the two-step oxidation of methane to formaldehyde by sBMO. Unlike methanol, alcohols with chain length C2–C5 do not compete effectively with their respective alkane substrates. Results from product inhibition experiments suggest that the geometry of the active site is optimized for linear molecules four to five carbons in length and is influenced by the regulatory protein component B (butane monooxygenase regulatory component; BMOB). The data suggest that alkane oxidation by sBMO is highly specialized for the turnover of C3–C5 alkanes and the release of their respective alcohol products. Additionally, sBMO is particularly efficient at preventing methane oxidation during growth on linear alkanes ≥C2, despite its high sequence homology with sMMO. These results represent, to the best of our knowledge, the first kinetic in vitro characterization of the closest known homologue of sMMO.

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11

Morikawa, Masaaki, Mitsuhide Kanemoto, and Tadayuki Imanaka. "Biological oxidation of alkane to alkene under anaerobic conditions." Journal of Fermentation and Bioengineering 82, no. 3 (1996): 309–11. http://dx.doi.org/10.1016/0922-338x(96)88825-8.

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12

Smith, Christy A., and Michael R. Hyman. "Oxidation of Methyl tert-Butyl Ether by Alkane Hydroxylase in Dicyclopropylketone-Induced and n-Octane-Grown Pseudomonas putida GPo1." Applied and Environmental Microbiology 70, no. 8 (August 2004): 4544–50. http://dx.doi.org/10.1128/aem.70.8.4544-4550.2004.

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ABSTRACT The alkane hydroxylase enzyme system in Pseudomonas putida GPo1 has previously been reported to be unreactive toward the gasoline oxygenate methyl tert-butyl ether (MTBE). We have reexamined this finding by using cells of strain GPo1 grown in rich medium containing dicyclopropylketone (DCPK), a potent gratuitous inducer of alkane hydroxylase activity. Cells grown with DCPK oxidized MTBE and generated stoichiometric quantities of tert-butyl alcohol (TBA). Cells grown in the presence of DCPK also oxidized tert-amyl methyl ether but did not appear to oxidize either TBA, ethyl tert-butyl ether, or tert-amyl alcohol. Evidence linking MTBE oxidation to alkane hydroxylase activity was obtained through several approaches. First, no TBA production from MTBE was observed with cells of strain GPo1 grown on rich medium without DCPK. Second, no TBA production from MTBE was observed in DCPK-treated cells of P. putida GPo12, a strain that lacks the alkane-hydroxylase-encoding OCT plasmid. Third, all n-alkanes that support the growth of strain GPo1 inhibited MTBE oxidation by DCPK-treated cells. Fourth, two non-growth-supporting n-alkanes (propane and n-butane) inhibited MTBE oxidation in a saturable, concentration-dependent process. Fifth, 1,7-octadiyne, a putative mechanism-based inactivator of alkane hydroxylase, fully inhibited TBA production from MTBE. Sixth, MTBE-oxidizing activity was also observed in n-octane-grown cells. Kinetic studies with strain GPo1 grown on n-octane or rich medium with DCPK suggest that MTBE-oxidizing activity may have previously gone undetected in n-octane-grown cells because of the unusually high Ks value (20 to 40 mM) for MTBE.

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13

Koch, Daniel J., Mike M. Chen, Jan B. van Beilen, and Frances H. Arnold. "In Vivo Evolution of Butane Oxidation by Terminal Alkane Hydroxylases AlkB and CYP153A6." Applied and Environmental Microbiology 75, no. 2 (November 14, 2008): 337–44. http://dx.doi.org/10.1128/aem.01758-08.

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ABSTRACT Enzymes of the AlkB and CYP153 families catalyze the first step in the catabolism of medium-chain-length alkanes, selective oxidation of the alkane to the 1-alkanol, and enable their host organisms to utilize alkanes as carbon sources. Small, gaseous alkanes, however, are converted to alkanols by evolutionarily unrelated methane monooxygenases. Propane and butane can be oxidized by CYP enzymes engineered in the laboratory, but these produce predominantly the 2-alkanols. Here we report the in vivo-directed evolution of two medium-chain-length terminal alkane hydroxylases, the integral membrane di-iron enzyme AlkB from Pseudomonas putida GPo1 and the class II-type soluble CYP153A6 from Mycobacterium sp. strain HXN-1500, to enhance their activity on small alkanes. We established a P. putida evolution system that enables selection for terminal alkane hydroxylase activity and used it to select propane- and butane-oxidizing enzymes based on enhanced growth complementation of an adapted P. putida GPo12(pGEc47ΔB) strain. The resulting enzymes exhibited higher rates of 1-butanol production from butane and maintained their preference for terminal hydroxylation. This in vivo evolution system could be useful for directed evolution of enzymes that function efficiently to hydroxylate small alkanes in engineered hosts.

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14

Bales, Brian C., Peter Brown, Ahmad Dehestani, and James M. Mayer. "Alkane Oxidation by Osmium Tetroxide." Journal of the American Chemical Society 127, no. 9 (March 2005): 2832–33. http://dx.doi.org/10.1021/ja044273w.

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15

Neumann, Ronny, and Chalil Abu-Gnim. "A ruthenium heteropolyanion as catalyst for alkane and alkene oxidation." Journal of the Chemical Society, Chemical Communications, no. 18 (1989): 1324. http://dx.doi.org/10.1039/c39890001324.

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16

Doughty, D. M., L. A. Sayavedra-Soto, D. J. Arp, and P. J. Bottomley. "Product Repression of Alkane Monooxygenase Expression in Pseudomonas butanovora." Journal of Bacteriology 188, no. 7 (April 1, 2006): 2586–92. http://dx.doi.org/10.1128/jb.188.7.2586-2592.2006.

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ABSTRACT Physiological and regulatory mechanisms that allow the alkane-oxidizing bacterium Pseudomonas butanovora to consume C2 to C8 alkane substrates via butane monooxygenase (BMO) were examined. Striking differences were observed in response to even- versus odd-chain-length alkanes. Propionate, the downstream product of propane oxidation and of the oxidation of other odd-chain-length alkanes following β-oxidation, was a potent repressor of BMO expression. The transcriptional activity of the BMO promoter was reduced with as little as 10 μM propionate, even in the presence of appropriate inducers. Propionate accumulated stoichiometrically when 1-propanol and propionaldehyde were added to butane- and ethane-grown cells, indicating that propionate catabolism was inactive during growth on even-chain-length alkanes. In contrast, propionate consumption was induced (about 80 nmol propionate consumed · min−1 · mg protein−1) following growth on the odd-chain-length alkanes, propane and pentane. The induction of propionate consumption could be brought on by the addition of propionate or pentanoate to the growth medium. In a reporter strain of P. butanovora in which the BMO promoter controls β-galactosidase expression, only even-chain-length alcohols (C2 to C8) induced β-galactosidase following growth on acetate or butyrate. In contrast, both even- and odd-chain-length alcohols (C3 to C7) were able to induce β-galactosidase following the induction of propionate consumption by propionate or pentanoate.

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17

Habets-Crützen, A. Q. H., and J. A. M. de Bont. "Inactivation of alkene oxidation by epoxides in alkene-and alkane-grown bacteria." Applied Microbiology and Biotechnology 22, no. 6 (October 1985): 428–33. http://dx.doi.org/10.1007/bf00252785.

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18

Marín, Mercedes M., Luis Yuste, and Fernando Rojo. "Differential Expression of the Components of the Two Alkane Hydroxylases from Pseudomonas aeruginosa." Journal of Bacteriology 185, no. 10 (May 15, 2003): 3232–37. http://dx.doi.org/10.1128/jb.185.10.3232-3237.2003.

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ABSTRACT Oxidation of n-alkanes in bacteria is normally initiated by an enzyme system formed by a membrane-bound alkane hydroxylase and two soluble proteins, rubredoxin and rubredoxin reductase. Pseudomonas aeruginosa strains PAO1 and RR1 contain genes encoding two alkane hydroxylases (alkB1 and alkB2), two rubredoxins (alkG1 and alkG2), and a rubredoxin reductase (alkT). We have localized the promoters for these genes and analyzed their expression under different conditions. The alkB1 and alkB2 genes were preferentially expressed at different moments of the growth phase; expression of alkB2 was highest during the early exponential phase, while alkB1 was induced at the late exponential phase, when the growth rate decreased. Both genes were induced by C10 to C22/C24 alkanes but not by their oxidation derivatives. However, the alkG1, alkG2, and alkT genes were expressed at constant levels in both the absence and presence of alkanes.

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19

Sabirova, Julia S., Manuel Ferrer, Daniela Regenhardt, Kenneth N. Timmis, and Peter N. Golyshin. "Proteomic Insights into Metabolic Adaptations in Alcanivorax borkumensis Induced by Alkane Utilization." Journal of Bacteriology 188, no. 11 (June 1, 2006): 3763–73. http://dx.doi.org/10.1128/jb.00072-06.

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ABSTRACT Alcanivorax borkumensis is a ubiquitous marine petroleum oil-degrading bacterium with an unusual physiology specialized for alkane metabolism. This “hydrocarbonoclastic” bacterium degrades an exceptionally broad range of alkane hydrocarbons but few other substrates. The proteomic analysis presented here reveals metabolic features of the hydrocarbonoclastic lifestyle. Specifically, hexadecane-grown and pyruvate-grown cells differed in the expression of 97 cytoplasmic and membrane-associated proteins whose genes appeared to be components of 46 putative operon structures. Membrane proteins up-regulated in alkane-grown cells included three enzyme systems able to convert alkanes via terminal oxidation to fatty acids, namely, enzymes encoded by the well-known alkB1 gene cluster and two new alkane hydroxylating systems, a P450 cytochrome monooxygenase and a putative flavin-binding monooxygenase, and enzymes mediating β-oxidation of fatty acids. Cytoplasmic proteins up-regulated in hexadecane-grown cells reflect a central metabolism based on a fatty acid diet, namely, enzymes of the glyoxylate bypass and of the gluconeogenesis pathway, able to provide key metabolic intermediates, like phosphoenolpyruvate, from fatty acids. They also include enzymes for synthesis of riboflavin and of unsaturated fatty acids and cardiolipin, which presumably reflect membrane restructuring required for membranes to adapt to perturbations induced by the massive influx of alkane oxidation enzymes. Ancillary functions up-regulated included the lipoprotein releasing system (Lol), presumably associated with biosurfactant release, and polyhydroxyalkanoate synthesis enzymes associated with carbon storage under conditions of carbon surfeit. The existence of three different alkane-oxidizing systems is consistent with the broad range of oil hydrocarbons degraded by A. borkumensis and its ecological success in oil-contaminated marine habitats.

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20

Khaligh, Nader Ghaffari. "Recent Advances and Applications of tert-Butyl Nitrite (TBN) in Organic Synthesis." Mini-Reviews in Organic Chemistry 17, no. 1 (January 27, 2020): 3–25. http://dx.doi.org/10.2174/1570193x15666181029141019.

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This mini-review will present the recent applications of Tert-Butyl Nitrite (TBN) in organic synthesis. Due to its unique structural feature and wide application, TBN holds a prominent and great potential in organic synthesis. The applications of TBN in three areas viz. aerobic oxidation, annulation, and diazotization were reviewed recently; now, the current mini-review will describe the studies carried out to date in areas such as nitration of alkane, alkene, alkyne, and aromatic compounds, nitrosylation and sequential nitrosylation reactions, using TBN as source of oxygen and nitrogen. The mechanisms of these transformations will be briefly described in this mini-review.

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21

Karasevich, Elena I., Vera S. Kulikova, Aleksandr E. Shilov, and Al'bert A. Shteinman. "Biomimetic alkane oxidation involving metal complexes." Russian Chemical Reviews 67, no. 4 (April 30, 1998): 335–55. http://dx.doi.org/10.1070/rc1998v067n04abeh000315.

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22

Hutchings, G. J. "Alkane oxidation using iron oxo centres." Applied Catalysis A: General 84, no. 2 (May 1992): N17. http://dx.doi.org/10.1016/0926-860x(92)80118-v.

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23

Shteinman, A. A. "Biomimetic alkane oxidation: Modelling methane monooxygenase." Journal of Inorganic Biochemistry 59, no. 2-3 (August 1995): 408. http://dx.doi.org/10.1016/0162-0134(95)97506-l.

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24

Rappe, Anthony K., and Maria Jaworska. "Mechanism of Chromyl Chloride Alkane Oxidation." Journal of the American Chemical Society 125, no. 46 (November 2003): 13956–57. http://dx.doi.org/10.1021/ja036362z.

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25

van Beilen, Jan B., Marcel G. Wubbolts, and Bernard Witholt. "Genetics of alkane oxidation byPseudomonas oleovorans." Biodegradation 5, no. 3-4 (December 1994): 161–74. http://dx.doi.org/10.1007/bf00696457.

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26

Lo Piccolo, Luca, Claudio De Pasquale, Roberta Fodale, Anna Maria Puglia, and Paola Quatrini. "Involvement of an Alkane Hydroxylase System ofGordoniasp. Strain SoCg in Degradation of Solidn-Alkanes." Applied and Environmental Microbiology 77, no. 4 (December 23, 2010): 1204–13. http://dx.doi.org/10.1128/aem.02180-10.

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ABSTRACTEnzymes involved in oxidation of long-chainn-alkanes are still not well known, especially those in Gram-positive bacteria. This work describes the alkane degradation system of then-alkane degrader actinobacteriumGordoniasp. strain SoCg, which is able to grow onn-alkanes from dodecane (C12) to hexatriacontane (C36) as the sole C source. SoCg harbors in its chromosome a singlealklocus carrying six open reading frames (ORFs), which shows 78 to 79% identity with the alkane hydroxylase (AH)-encoding systems of other alkane-degrading actinobacteria. Quantitative reverse transcription-PCR showed that the genes encoding AlkB (alkane 1-monooxygenase), RubA3 (rubredoxin), RubA4 (rubredoxin), and RubB (rubredoxin reductase) were induced by bothn-hexadecane andn-triacontane, which were chosen as representative long-chain liquid and solidn-alkane molecules, respectively. Biotransformation ofn-hexadecane into the corresponding 1-hexadecanol was detected by solid-phase microextraction coupled with gas chromatography-mass spectrometry (SPME/GC-MS) analysis. TheGordoniaSoCgalkBwas heterologously expressed inEscherichia coliBL21 and inStreptomyces coelicolorM145, and both hosts acquired the ability to transformn-hexadecane into 1-hexadecanol, but the corresponding long-chain alcohol was never detected onn-triacontane. However, the recombinantS. coelicolorM145-AH, expressing theGordonia alkBgene, was able to grow onn-triacontane as the sole C source. A SoCgalkBdisruption mutant that is completely unable to grow onn-triacontane was obtained, demonstrating the role of an AlkB-type AH system in degradation of solidn-alkanes.

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Endoh-Yamagami, Setsu, Kiyoshi Hirakawa, Daisuke Morioka, Ryouichi Fukuda, and Akinori Ohta. "Basic Helix-Loop-Helix Transcription Factor Heterocomplex of Yas1p and Yas2p Regulates Cytochrome P450 Expression in Response to Alkanes in the Yeast Yarrowia lipolytica." Eukaryotic Cell 6, no. 4 (February 23, 2007): 734–43. http://dx.doi.org/10.1128/ec.00412-06.

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ABSTRACT The expression of the ALK1 gene, which encodes cytochrome P450, catalyzing the first step of alkane oxidation in the alkane-assimilating yeast Yarrowia lipolytica, is highly regulated and can be induced by alkanes. Previously, we identified a cis-acting element (alkane-responsive element 1 [ARE1]) in the ALK1 promoter. We showed that a basic helix-loop-helix (bHLH) protein, Yas1p, binds to ARE1 in vivo and mediates alkane-dependent transcription induction. Yas1p, however, does not bind to ARE1 by itself in vitro, suggesting that Yas1p requires another bHLH protein partner for its DNA binding, as many bHLH transcription factors function by forming heterodimers. To identify such a binding partner of Yas1p, here we screened open reading frames encoding proteins with the bHLH motif from the Y. lipolytica genome database and identified the YAS2 gene. The deletion of the YAS2 gene abolished the alkane-responsive induction of ALK1 transcription and the growth of the yeast on alkanes. We revealed that Yas2p has transactivation activity. Furthermore, Yas1p and Yas2p formed a protein complex that was required for the binding of these proteins to ARE1. These findings allow us to postulate a model in which bHLH transcription factors Yas1p and Yas2p form a heterocomplex and mediate the transcription induction in response to alkanes.

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Nason, Abigail K., Austin Jerad Reese, and Jin Suntivich. "Intermediate-Temperature Alkane Electrochemical Activation." ECS Meeting Abstracts MA2022-02, no. 49 (October 9, 2022): 1917. http://dx.doi.org/10.1149/ma2022-02491917mtgabs.

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Electrochemical activation of alkanes plays an enabling role for applications ranging from fuel cells to electro-production of materials and chemicals. Intermediate-temperature (>200 oC) electrochemical devices have improved diffusions, reaction kinetics, and feedstock flexibility. In this contribution, we present the electrochemical activation of alkanes using intermediate-temperature electrochemical devices. Our work is inspired by Duan et al. whose work showed that alkanes can be oxidized as fuel in protonic ceramic fuel cells1. We extend this concept and evaluate whether this electrochemical activation can activate longer-chain hydrocarbons to form industrial gases. We present a comparison of the electrochemical approach to pyrolysis, and in particular, its selectivity. Different electrocatalysts will be evaluated to test both electrochemical and thermal oxidation. Finally, we use small-molecule oxidation experiments to probe how the thermochemical reactions occur in parallel with the electrochemical conversion. We identify the products from these processes and propose the alkane activation mechanism. Duan, C.; Kee, R. J.; Zhu, H.; Karakaya, C.; Chen, Y.; Ricote, S.; Jarry, A.; Crumlin, E. J.; Hook, D.; Braun, R.; Sullivan, N. P.; O’Hayre, R., Highly durable, coking and sulfur tolerant, fuel-flexible protonic ceramic fuel cells. Nature 2018, 557 (7704), 217-222.

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Li, Xuan, Detre Teschner, Verena Streibel, Thomas Lunkenbein, Liudmyla Masliuk, Teng Fu, Yuanqing Wang, et al. "How to control selectivity in alkane oxidation?" Chemical Science 10, no. 8 (2019): 2429–43. http://dx.doi.org/10.1039/c8sc04641g.

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30

Jacobs, Cheri Louise, Rodolpho do Aido-Machado, Carmien Tolmie, Martha Sophia Smit, and Diederik Johannes Opperman. "CYP153A71 from Alcanivorax dieselolei: Oxidation beyond Monoterminal Hydroxylation of n-Alkanes." Catalysts 12, no. 10 (October 11, 2022): 1213. http://dx.doi.org/10.3390/catal12101213.

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Selective oxyfunctionalization of non-activated C–H bonds remains a major challenge in synthetic chemistry. The biocatalytic hydroxylation of non-activated C–H bonds by cytochrome P450 monooxygenases (CYPs), however, offers catalysis with high regio- and stereoselectivity using molecular oxygen. CYP153s are a class of CYPs known for their selective terminal hydroxylation of n-alkanes and microorganisms, such as the bacterium Alcanivorax dieselolei, have evolved extensive enzymatic pathways for the oxyfunctionalization of various lengths of n-alkanes, including a CYP153 to yield medium-chain 1-alkanols. In this study, we report the characterization of the terminal alkane hydroxylase from A. dieselolei (CYP153A71) for the oxyfunctionalization of medium-chain n-alkanes in comparison to the well-known CYP153A6 and CYP153A13. Although the expected 1-alkanols are produced, CYP153A71 readily converts the 1-alkanols to the corresponding aldehydes, fatty acids, as well as α,ω-diols. CYP153A71 is also shown to readily hydroxylate medium-chain fatty acids. The X-ray crystal structure of CYP153A71 bound to octanoic acid is solved, yielding an insight into not only the regioselectivity, but also the binding orientation of the substrate, which can be used in future studies to evolve CYP153A71 for improved oxidations beyond terminal n-alkane hydroxylation.

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31

Zhang, X., R. H. Schwantes, M. M. Coggon, C. L. Loza, K. A. Schilling, R. C. Flagan, and J. H. Seinfeld. "Role of ozone in SOA formation from alkane photooxidation." Atmospheric Chemistry and Physics Discussions 13, no. 9 (September 24, 2013): 24713–54. http://dx.doi.org/10.5194/acpd-13-24713-2013.

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Abstract. Long-chain alkanes, which can be categorized as intermediate volatile organic compounds (IVOCs), are an important source of secondary organic aerosol (SOA). Mechanisms for the gas-phase OH-initiated oxidation of long-chain alkanes have been well documented; particle-phase chemistry, however, has received less attention. The δ-hydroxycarbonyl, which is generated from the isomerization of alkoxy radicals, can undergo heterogeneous cyclization to form substituted dihydrofuran. Due to the presence of C=C bonds, the substituted dihydrofuran is predicted to be highly reactive with OH, and even more so with O3 and NO3, thus opening a reaction pathway that is not usually accessible to alkanes. This work focuses on the role of substituted dihydrofuran formation and its subsequent reaction with OH, and more importantly ozone, in SOA formation from the photooxidation of long-chain alkanes. Experiments were carried out in the Caltech Environmental Chamber using dodecane as a representative alkane to investigate the difference in aerosol composition generated from "OH-oxidation dominating" vs. "ozonolysis dominating" environments. A detailed mechanism incorporating the specific gas-phase photochemistry, together with the heterogeneous formation of substituted dihydrofuran and its subsequent gas-phase OH/O3 oxidation, is presented to evaluate the importance of this reaction channel in the dodecane SOA formation. We conclude that: (1) the formation of δ-hydroxycarbonyl and its subsequent heterogeneous conversion to substituted dihydrofuran is significant in the presence of NOx; (2) the ozonolysis of substituted dihydrofuran dominates over the OH-initiated oxidation under conditions prevalent in urban and rural air; and (3) a spectrum of highly-oxygenated products with carboxylic acid, ester, and ether functional groups are produced from the substituted dihydrofuran chemistry, thereby affecting the average oxidation state of the SOA.

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32

Zhang, X., R. H. Schwantes, M. M. Coggon, C. L. Loza, K. A. Schilling, R. C. Flagan, and J. H. Seinfeld. "Role of ozone in SOA formation from alkane photooxidation." Atmospheric Chemistry and Physics 14, no. 3 (February 14, 2014): 1733–53. http://dx.doi.org/10.5194/acp-14-1733-2014.

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Abstract. Long-chain alkanes, which can be categorized as intermediate volatility organic compounds, are an important source of secondary organic aerosol (SOA). Mechanisms for the gas-phase OH-initiated oxidation of long-chain alkanes have been well documented; particle-phase chemistry, however, has received less attention. The δ-hydroxycarbonyl, which is generated from the isomerization of alkoxy radicals, can undergo heterogeneous cyclization and dehydration to form substituted dihydrofuran. Due to the presence of C=C bonds, the substituted dihydrofuran is predicted to be highly reactive with OH, and even more so with O3 and NO3, thereby opening a reaction pathway that is not usually accessible to alkanes. This work focuses on the role of substituted dihydrofuran formation and its subsequent reaction with OH, and more importantly ozone, in SOA formation from the photooxidation of long-chain alkanes. Experiments were carried out in the Caltech Environmental Chamber using dodecane as a representative alkane to investigate the difference in aerosol composition generated from "OH-oxidation-dominating" vs. "ozonolysis-dominating" environments. A detailed mechanism incorporating the specific gas-phase photochemistry, together with the heterogeneous formation of substituted dihydrofuran and its subsequent gas-phase OH/O3 oxidation, is used to evaluate the importance of this reaction channel in dodecane SOA formation. We conclude that (1) the formation of δ-hydroxycarbonyl and its subsequent heterogeneous conversion to substituted dihydrofuran is significant in the presence of NOx; (2) the ozonolysis of substituted dihydrofuran dominates over the OH-initiated oxidation under conditions prevalent in urban and rural air; and (3) a spectrum of highly oxygenated products with carboxylic acid, ester, and ether functional groups are produced from the substituted dihydrofuran chemistry, thereby affecting the average oxidation state of the SOA.

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33

Johnson, Erika L., and Michael R. Hyman. "Propane and n-Butane Oxidation by Pseudomonas putida GPo1." Applied and Environmental Microbiology 72, no. 1 (January 2006): 950–52. http://dx.doi.org/10.1128/aem.72.1.950-952.2006.

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ABSTRACT Propane and n-butane inhibit methyl tertiary butyl ether oxidation by n-alkane-grown Pseudomonas putida GPo1. Here we demonstrate that these gases are oxidized by this strain and support cell growth. Both gases induced alkane hydroxylase activity and appear to be oxidized by the same enzyme system used for the oxidation of n-octane.

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34

Tian, Dan, Lei Xu, and Dong Liu. "Effects of Carbon Chain Length on N-Alkane Counterflow Cool Flames: A Kinetic Analysis." Fire 5, no. 5 (October 18, 2022): 170. http://dx.doi.org/10.3390/fire5050170.

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An in-depth understanding of the low-temperature reactivity of hydrocarbon fuels is of practical relevance to developing advanced low-temperature combustion techniques. The present study aims to study the low-temperature chemistry of several large n-alkanes with different carbon chain lengths in counterflow cool diffusion flames by kinetic analysis. The large n-alkanes that were chosen are n-heptane (NC7H16), n-decane (NC10H22) and n-dodecane (NC12H26), which are important components of practical fuels. Firstly, the thermochemical structure of a typical cool diffusion flame is understood through its comparison with that of a hot diffusion flame. The boundary conditions, including the ozone concentration, fuel concentration and flow velocity—where cool flames can be established—are identified with a detailed chemical mechanism that evaluates the low-temperature reactivity of the investigated n-alkanes. The results show that the n-alkane with a longer carbon chain length is more reactive than the smaller one, thereby indicating the order of NC12H26 > NC10H22 > NC7H16. This trend is qualitatively similar to the findings from non-flame reactors. The reaction pathway and sensitivity analysis are performed to understand the effects of carbon chain length on the low-temperature reactivity. The contribution of an n-alkane with a longer carbon chain to the dehydrogenation reaction, oxidation reaction and isomerization reaction is greater than that of a smaller n-alkane, and abundant O and OH radicals are generated to promote the fuel low-temperature oxidation process, thereby resulting in an enhanced low-temperature reactivity. The effects of ozone addition on the low-temperature reactivity of n-alkanes are also highlighted. It is found that the addition of ozone could provide a large number of active O radicals, which dehydrogenate with the fuels to generate OH radicals and then promote fuel low-temperature oxidation. The present results are expected to enrich the understanding of the low-temperature characteristics of large n-alkanes.

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35

Ueda, Wataru. "Challenges in alkane activation and selective oxidation." Catalysis Today 71, no. 1-2 (November 2001): 1. http://dx.doi.org/10.1016/s0920-5861(01)00447-3.

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36

Riaz, Sara, Muhammad Nasir, Jibran Iqbal, and Mian Hasnain Nawaz. "Polystyrenic porphyrins as catalysts for alkane oxidation." Research on Chemical Intermediates 41, no. 9 (June 18, 2014): 6283–87. http://dx.doi.org/10.1007/s11164-014-1739-x.

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37

Eichelbaum, Maik, Michael Hävecker, Christian Heine, Anna Maria Wernbacher, Frank Rosowski, Annette Trunschke, and Robert Schlögl. "The Electronic Factor in Alkane Oxidation Catalysis." Angewandte Chemie International Edition 54, no. 10 (January 28, 2015): 2922–26. http://dx.doi.org/10.1002/anie.201410632.

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38

Davidson, D. F., J. T. Herbon, D. C. Horning, and R. K. Hanson. "OH concentration time histories inn-alkane oxidation." International Journal of Chemical Kinetics 33, no. 12 (2001): 775–83. http://dx.doi.org/10.1002/kin.10000.

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39

Wang, Zhandong, Denisia M. Popolan-Vaida, Bingjie Chen, Kai Moshammer, Samah Y. Mohamed, Heng Wang, Salim Sioud, et al. "Unraveling the structure and chemical mechanisms of highly oxygenated intermediates in oxidation of organic compounds." Proceedings of the National Academy of Sciences 114, no. 50 (November 28, 2017): 13102–7. http://dx.doi.org/10.1073/pnas.1707564114.

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Decades of research on the autooxidation of organic compounds have provided fundamental and practical insights into these processes; however, the structure of many key autooxidation intermediates and the reactions leading to their formation still remain unclear. This work provides additional experimental evidence that highly oxygenated intermediates with one or more hydroperoxy groups are prevalent in the autooxidation of various oxygenated (e.g., alcohol, aldehyde, keto compounds, ether, and ester) and nonoxygenated (e.g., normal alkane, branched alkane, and cycloalkane) organic compounds. These findings improve our understanding of autooxidation reaction mechanisms that are routinely used to predict fuel ignition and oxidative stability of liquid hydrocarbons, while also providing insights relevant to the formation mechanisms of tropospheric aerosol building blocks. The direct observation of highly oxygenated intermediates for the autooxidation of alkanes at 500–600 K builds upon prior observations made in atmospheric conditions for the autooxidation of terpenes and other unsaturated hydrocarbons; it shows that highly oxygenated intermediates are stable at conditions above room temperature. These results further reveal that highly oxygenated intermediates are not only accessible by chemical activation but also by thermal activation. Theoretical calculations on H-atom migration reactions are presented to rationalize the relationship between the organic compound’s molecular structure (n-alkane, branched alkane, and cycloalkane) and its propensity to produce highly oxygenated intermediates via extensive autooxidation of hydroperoxyalkylperoxy radicals. Finally, detailed chemical kinetic simulations demonstrate the influence of these additional reaction pathways on the ignition of practical fuels.

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40

Lyu, Ruihe, Mohammed S. Alam, Christopher Stark, Ruixin Xu, Zongbo Shi, Yinchang Feng, and Roy M. Harrison. "Aliphatic carbonyl compounds (C<sub>8</sub>–C<sub>26</sub>) in wintertime atmospheric aerosol in London, UK." Atmospheric Chemistry and Physics 19, no. 4 (February 20, 2019): 2233–46. http://dx.doi.org/10.5194/acp-19-2233-2019.

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Abstract. Three groups of aliphatic carbonyl compounds, the n-alkanals (C8–C20), n-alkan-2-ones (C8–C26), and n-alkan-3-ones (C8–C19), were measured in both particulate and vapour phases in air samples collected in London from January to April 2017. Four sites were sampled including two rooftop background sites, one ground-level urban background site, and a street canyon location on Marylebone Road in central London. The n-alkanals showed the highest concentrations, followed by the n-alkan-2-ones and the n-alkan-3-ones, the latter having appreciably lower concentrations. It seems likely that all compound groups have both primary and secondary sources and these are considered in light of published laboratory work on the oxidation products of high-molecular-weight n-alkanes. All compound groups show a relatively low correlation with black carbon and NOx in the background air of London, but in street canyon air heavily impacted by vehicle emissions, stronger correlations emerge, especially for the n-alkanals. It appears that vehicle exhaust is likely to be a major contributor for concentrations of the n-alkanals, whereas it is a much smaller contributor to the n-alkan-2-ones and n-alkan-3-ones. Other primary sources such as cooking or wood burning may be contributors for the ketones but were not directly evaluated. It seems likely that there is also a significant contribution from the photo-oxidation of n-alkanes and this would be consistent with the much higher abundance of n-alkan-2-ones relative to n-alkan-3-ones if the formation mechanism were through the oxidation of condensed-phase alkanes. Vapour–particle partitioning fitted the Pankow model well for the n-alkan-2-ones but less well for the other compound groups, although somewhat stronger relationships were seen at the Marylebone Road site than at the background sites. The former observation gives support to the n-alkane-2-ones being a predominantly secondary product, whereas primary sources of the other groups are more prominent.

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41

Whyte, Lyle G., Jalal Hawari, Edward Zhou, Luc Bourbonnière, William E. Inniss, and Charles W. Greer. "Biodegradation of Variable-Chain-Length Alkanes at Low Temperatures by a Psychrotrophic Rhodococcussp." Applied and Environmental Microbiology 64, no. 7 (July 1, 1998): 2578–84. http://dx.doi.org/10.1128/aem.64.7.2578-2584.1998.

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ABSTRACT The psychrotroph Rhodococcus sp. strain Q15 was examined for its ability to degrade individual n-alkanes and diesel fuel at low temperatures, and its alkane catabolic pathway was investigated by biochemical and genetic techniques. At 0 and 5°C, Q15 mineralized the short-chain alkanes dodecane and hexadecane to a greater extent than that observed for the long-chain alkanes octacosane and dotriacontane. Q15 utilized a broad range of aliphatics (C10 to C21 alkanes, branched alkanes, and a substituted cyclohexane) present in diesel fuel at 5°C. Mineralization of hexadecane at 5°C was significantly greater in both hydrocarbon-contaminated and pristine soil microcosms seeded with Q15 cells than in uninoculated control soil microcosms. The detection of hexadecane and dodecane metabolic intermediates (1-hexadecanol and 2-hexadecanol and 1-dodecanol and 2-dodecanone, respectively) by solid-phase microextraction–gas chromatography-mass spectrometry and the utilization of potential metabolic intermediates indicated that Q15 oxidizes alkanes by both the terminal oxidation pathway and the subterminal oxidation pathway. Genetic characterization by PCR and nucleotide sequence analysis indicated that Q15 possesses an aliphatic aldehyde dehydrogenase gene highly homologous to the Rhodococcus erythropolis thcA gene. Rhodococcus sp. strain Q15 possessed two large plasmids of approximately 90 and 115 kb (shown to mediate Cd resistance) which were not required for alkane mineralization, although the 90-kb plasmid enhanced mineralization of some alkanes and growth on diesel oil at both 5 and 25°C.

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42

Grau, Michaela, Andrew Kyriacou, Fernando Cabedo Martinez, Irene M. de Wispelaere, Andrew J. P. White, and George J. P. Britovsek. "Unraveling the origins of catalyst degradation in non-heme iron-based alkane oxidation." Dalton Trans. 43, no. 45 (2014): 17108–19. http://dx.doi.org/10.1039/c4dt02067g.

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A series of iron(ii) complexes with tetradentate and pentadentate pyridyl amine ligands has been used for the oxidation of cyclohexane with hydrogen peroxide. Ligand degradation is observed under oxidising conditions via oxidative N-dealkylation.

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43

Liu, Ruyin, Yingxin Gao, Yifeng Ji, Yu Zhang, and Min Yang. "Characteristics of hydrocarbon hydroxylase genes in a thermophilic aerobic biological system treating oily produced wastewater." Water Science and Technology 71, no. 1 (November 22, 2014): 75–82. http://dx.doi.org/10.2166/wst.2014.470.

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Alkane and aromatic hydroxylase genes in a full-scale aerobic system treating oily produced wastewater under thermophilic condition (45–50 °C) in the Jidong oilfield, China, were investigated using clone library and quantitative polymerase chain reaction methods. Rather than the normally encountered integral-membrane non-haem iron monooxygenase (alkB) genes, only CYP153-type P450 hydroxylase genes were detected for the alkane activation, indicating that the terminal oxidation of alkanes might be mainly mediated by the CYP153-type alkane hydroxylases in the thermophilic aerobic process. Most of the obtained CYP153 gene clones showed distant homology with the reference sequences, which might represent novel alkane hydroxylases. For the aromatic activation, the polycyclic aromatic hydrocarbon-ring hydroxylating dioxygenase (PAH-RHD) gene was derived from Gram-negative PAH-degraders belonging to the Burkholderiales order, with a 0.72% relative abundance of PAH-RHD gene to 16S rRNA gene. This was consistent with the result of 16S rRNA gene analysis, indicating that Burkholderiales bacteria might play a key role in the full-scale process of thermophilic hydrocarbon degradation.

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44

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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45

Devynck, Jacques, Abderaouf Ben-Hadid, Paul-Louis Fabre, Bernard Tremillon, and Bernard Carré. "Alkane and alkene oxidation in fluorinated superacid media: Role of the acidity level." Journal of Fluorine Chemistry 35, no. 1 (February 1987): 214. http://dx.doi.org/10.1016/0022-1139(87)95168-2.

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46

Koch, Gregor, Michael Hävecker, Detre Teschner, Spencer J. Carey, Yuanqing Wang, Pierre Kube, Walid Hetaba, et al. "Surface Conditions That Constrain Alkane Oxidation on Perovskites." ACS Catalysis 10, no. 13 (May 29, 2020): 7007–20. http://dx.doi.org/10.1021/acscatal.0c01289.

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47

Veser, Götz, Murtaza Ziauddin, and Lanny D. Schmidt. "Ignition in alkane oxidation on noble-metal catalysts." Catalysis Today 47, no. 1-4 (January 1999): 219–28. http://dx.doi.org/10.1016/s0920-5861(98)00302-2.

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48

Kube, Pierre, Benjamin Frank, Sabine Wrabetz, Jutta Kröhnert, Michael Hävecker, Juan Velasco-Vélez, Johannes Noack, Robert Schlögl, and Annette Trunschke. "Functional Analysis of Catalysts for Lower Alkane Oxidation." ChemCatChem 9, no. 4 (January 9, 2017): 573–85. http://dx.doi.org/10.1002/cctc.201601194.

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49

KARASEVICH, E. I., V. S. KULIKOVA, A. E. SHILOV, and A. A. SHTEINMAN. "ChemInform Abstract: Biomimetic Alkane Oxidation Involving Metal Complexes." ChemInform 29, no. 36 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199836342.

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50

Sluyter, G., B. Grund, J. J. Müller, O. Thum, P. Bubenheim, and A. Liese. "Prozessentwicklung und Charakterisierung einer fermentativen Oxidation kurzkettiger Alkane." Chemie Ingenieur Technik 88, no. 9 (August 29, 2016): 1250. http://dx.doi.org/10.1002/cite.201650283.

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