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For the purpose of developing onboard gasoline reforming technology for higher octane number fuel on demand, octane number enhancement of gasoline surrogate by aerobic oxidation using N-hydroxyphthalimide catalyst was investigated. At first, octane numbers of the oxygen-containing products from alkane and aromatic compound were estimated using a fuel ignition analyzer. As a result, not only alcohol but also ketones and aldehydes have higher octane numbers than the original alkanes and aromatic compound. Next, gasoline surrogate was oxidized aerobically with N-hydroxyphthalimide derivative catalyst and cobalt catalyst at conditions below 100 °C. As a result, fuel molecules were oxidized to produce alcohols, ketones, aldehydes, and carboxylic acids. N-hydroxyphthalimide derivative catalyst with higher solubility in gasoline surrogate has higher oxidation ability. Furthermore, the estimated octane number of the oxidized gasoline surrogate improves 17 RON.