Aerobic ultra-deep desulfurization of diesel oil triggered by porous carbon supported organic molecular N-hydroxyphthalimide catalyst

Gao, Xiang; Jiang, Wei; An, Xin; Zhu, Kun; Zhu, Linhua; Wu, Peiwen; Zhu, Wenshuai; Li, Huaming

doi:10.1016/j.colsurfa.2022.128455

Cited by 2 publications

(1 citation statement)

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“…A possible decomposition route of the reactive intermediate, phthalimide-N-oxyl radical (PINO), is the ring-opening of imide moiety, which was proposed by Masui and coworkers based on mass spectrometric analysis of decomposition products (Figure 1b). [24] While heterogeneous support, [25][26][27][28][29][30][31][32] use of ionic liquid, [33][34][35][36][37] phase-transfer conditions, [38,39] supercritical CO 2 , [40] combination with other redox mediators, [41][42][43] and the combination of these techniques [37] have been suggested to address the lifetime issue, NHPI derivatives with intrinsic long lifetime are highly desirable. For aerobic oxidation of hydrocarbons, one of the examples superior to NHPI is lipophilic NHPI A reported by Ishii and coworkers (Figure 2a).…”

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confidence: 99%

Lipophilic N‐Hydroxyimide Derivatives: Design, Synthesis, and Application to Aerobic Alkane Oxidation Under Neat Conditions

et al. 2022

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This work reports the design and synthesis of a series of 5membered and 6-membered N-hydroxyimides flanked by lipophilic alkyl groups adjacent to carbonyl groups, aiming to endow lipophilicity and tolerance toward ring opening degradation. Their solubility in cyclohexane was 5-20 times higher than those of unsubstituted N-hydroxyphthalimide (NHPI) and even 3-10 times higher than a formerly known lipophilic NHPI analog bearing a long alkyl ester. UV-Vis spectroscopy determined the rate constants of first-order decay of N-oxyls, which revealed enhanced stability of 3,5-di-tert-butyl-NHPI and Nhydroxyglutarimide flanked by spiro-cyclohexanes compared with that of NHPI. Their bond dissociation energies were assessed by EPR spectroscopy and DFT calculation, suggesting these lipophilic N-hydroxyimides catalyzed aerobic cyclohexane oxidation under neat conditions with up to 60 turnovers, which is the highest among hitherto reported reactions under neat conditions.

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