Aliphatic compounds oxidation

Vogel TM, Criddle CS, McCarty PL. (1987). Transformations of halogenated aliphatic compounds Oxidation, reduction, substitution and dehydrohalogenation reactions occur abiotically or in microbial and mammalian systems. Environmental Science Technology 21(8) 722-736. 

Certain aliphatic compounds are oxidised by concentrated nitric acid, the carbon atoms being split off in pairs, with the formation of oxalic acid. This disruptive oxidation is shown by many carbohydrates, e.g., cane sugar, where the chains of secondary alcohol groups, -CH(OH)-CH(OH)-CH(OH)CH(OH)-, present in the molecule break down particularly readily to give oxalic acid. 

Under drinking water plant treatment conditions, humic materials and/ or resorcinol do not produce trihalomethanes with chlorine dioxide even when a slight excess of chlorine (1 percent to 2 percent) is present. Also, saturated aliphatic compounds are not reactive with chlorine dioxide. Alcohols are oxidized to the corresponding acids. 

Vannelli T, M Logan, DM Arciero, AB Hooper (1990) Degradation of halogenated aliphatic compounds by the ammonia-oxidizing bacterium Mfro omowa europaea. Appl Environ Microbiol 56 1169-1171. 

A method for determining the basicities of phosphoryl compounds has been decribed which is based on 31P n.m.r. chemical shift measurement and a two phase system consisting of an organic solvent and 12H sulphuric acid.245 The gas-phase protonation of aliphatic phosphine oxides have been determined by cyclotron resonance. There was a good correlation of pK4 with Kabachnik constants and HO... 

Kinetic Isotope Effect in Oxidation of Aliphatic Compounds by Ozone... 

Fig. 16.32 Alkane degradation under aerobic conditions, showing incorporation of oxygen from molecular oxygen into the aliphatic compound, producing a fatty acid. Fatty acids are oxidized further by p-oxidation [H] indicates reducing equivalents that are either required or formed in the reaction step. (Bouwer and Zender 1993)...

More drastic conditions of temperature, pressure and time gave carbon as the product from both aromatic and aliphatic compounds. This carbon is an activated char with decolorizing properties. Tars, tarry substances, the oxides of carbon, and the usual products of the oxidation of aromatic compounds (dicarboxylic acids) were all conspicuous by their absence. Benzotrifluoride oxidized to benzoyl fluoride. The aliphatic compounds cyclohexane, methycyclohexane, n-heptane, etc., could be oxidized to carbon and water. 

It has been recently described [55d) that aliphatic nitrile oxides can be formed in solution by treating an aliphatic a-nitro-hydrocarbon with phenylisocyanate in the presence of a catalytic amount of tri-ethylamine. Dehydration of the nitro compounds occurs with the con-committant formation of benzoylurea. From nitroethane, the reaction is formulated as follows ... 

Aliphatic hydroxylation. As well as unsaturated aliphatic compounds such as vinyl chloride mentioned above, which are metabolized by epoxidation, saturated aliphatic compounds also undergo oxidation. The initial products will be primary and secondary alcohols. For example, the solvent n-hexane is known to be metabolized to the secondary alcohol hexan-2-ol and then further to hexane-2,5-dione (Fig. 4.9) in occupationally exposed humans. The latter metabolite is believed to be responsible for the neuropathy caused by the solvent. Other toxicologically important examples are the nephrotoxic petrol constituents, 2,2,4- and 2,3,4-trimethylpentane, which are hydroxylated to... 

Vanelli, T., Logan, M., Arciero, D. M. Hooper, A. B. (1990). Degradationofhalogenated aliphatic compounds by the ammonia-oxidizing bacterium Nitrosomonas europeae. Applied and Environmental Microbiology, 56, 1169-71. 

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