H Photooxidation products of a no. 2 fuel oil were fractionated and examined by gas chromatography-mass spectrometry. Among the compound types identified were hydroperoxides (alkylated derivatives of tetralin hydroperoxide), phenolic compounds (highly alkylated phenols and tetrahydronaphthols), and carboxylic acids (substituted benzoic and naphthoic acids). Oil fractions and pure compounds characteristic of the photooxidation products were tested for toxicity to a yeast and several filamentous algae. 'The species tested varied in their tolerance toward the photoproducts, but hydroperoxides generally showed the highest toxicity: tetralin hydroperoxide, a t 4 X lo-,-' M. significantly reduced yeast growth. Carboxylic acids had less activity and phenolics were still less active. Tetralin hydroperoxide, a t concentrations greater than 8 X l W 5 M. reduced photosynthetic carbon fixation by Vaucht'ria and increased excretion of fixed car hon.It has been suggested that aging or weathering of petroleum surface films might lessen their toxicity to aquatic organisms because of the evaporation of toxic, low-boiling hydrocarbons (1 ) or transformation of hydrocarbons into oxygenated derivatives easily leached from slicks (2). However, thermal treatment or long-wavelength ultra\Violet (UV) irradiation of some petroleum products affords water-soluble fractions with greatly increased toxicity to bacteria (Y), algae ( 4 ) , marine invertebrates, and fish ( 5 ) . A preliminary study of the photooxidation of a no. 2 fuel oil showed that hydroperoxides, carbonyl compounds, phenols, and acids were produced ( 6 ) . Some photoproducts (hydroperoxides in particular) displayed considerable toxicity to a yeast. Succhciromyces cerecisiae. We report additional work on the molecular identification and antimicrobial activity of some constituents of the acidic fraction of the no. 2 fuel oil photoproducts. This fraction includes hydroperoxides (very weak acids having pK, = 12), phenols (weak acids, pK, = lo), and carboxylic acids (pK;, 3.51. MatcJrials arid MethodsSeparation of Acidic Fractions. The characteristics of the no. 2 fuel oil and the conditions for its irradiation with a Pyrex-filtered mercury arc were reported previously ( 6 ) . Irradiated oil (25 mL) was extracted three times with twice its volume of 1 M KOH containing 6% NaCi. T h e combined aqueous layers were washed with hexane, brought to pH 11.0, and reextracted with diethyl ether to afford a n ether-soluble "very weak acid fraction". The p H of the residual water layer was adjusted successively to 7.0 and 4.0 and extracted similarly a t each p H to afford a "weak acid" and a "strong acid" fraction, respectively.The concentrated ether extracts were separated by preparative TLC (the very weak acid fraction was first treated with thiacyclopentane ( 7 ) to convert hydroperoxides to alcohols) and the constituents of the principal bands were examined by GC-MS using a double-focusing instrument (Shrader Laboratories, Detroit, Mich.).Preparation of Water Extracts. The no. 2 fuel oil...
Abstract— β‐Carotene, at concentrations 0.1 mM, inhibits the formation of hydroperoxides and other oxidation products in a refined petroleum oil exposed to Pyrex‐filtered UV. The effect appears to be due to 1O2 quenching. A mechanism incorporating 1O2 and radical processes is proposed as a model for environmental photooxidation of petroleum.
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