Cobalt/N-Hydroxyphthalimide(NHPI)-Catalyzed Aerobic Oxidation of Hydrocarbons with Ionic Liquid Additive

Mahmood, Sajid; Xu, Bao‐Hua; Ren, Tian Lu; Zhang, Zhibo; Liu, Xiaomin; Zhang, Suojiang

doi:10.1016/j.mcat.2018.01.006

Cited by 33 publications

(15 citation statements)

References 99 publications

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“…In this context, very recently, Mahmood et al . reported the beneficial effect of catalytic amounts of different imidazolium‐based ILs (5 % mol) on the aerobic oxidation of toluene to the corresponding benzoic acid, in the presence of NHPI (10 % mol) and Co(OAc) 2 (0.5 % mol) . In this case, the authors observed a behavior quite similar to that reported by Sasson and co‐workers with lipophilic ammonium salts, that is, the formation of a biphasic water/organic medium with the ILs acting as surfactant and/or phase transfer catalysts.…”

Section: Introductionsupporting

confidence: 70%

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

et al. 2019

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The synergistic action between imidazolium based ionic liquid (IL) [bmim][OcOSO3] and Co(II)/N‐hydroxyphthalimide (NHPI) systems in the catalytic aerobic oxidation of ethylbenzene under solvent‐free conditions have been here demonstrated by reaching a 35 % conversion with 83 % of selectivity in acetophenone at 80 °C. This highly performing catalytic system have been selected after screening several different IL and Co(II) salt combinations, and making sure that the complete solubilization of the polar NHPI in the lipophilic medium, without thus requiring any chemical modification of the organic catalyst, could be attained. This solubilizing effect can be ascribed to a direct interaction between [bmim][OcOSO3] IL and NHPI as revealed by a detailed NMR investigation which also allowed to exclude the formation of higher IL aggregates in the form of micelles or vesicles.

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Section: Introductionsupporting

confidence: 70%

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

et al. 2019

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“…This trend is consistent with the literature reports. 23 The acidity of the ILs used depends on the anion present [pK a HBr (−9), 31 HCl (−8), 32 HBF 4 (−4.9), 33 HNTf 2 (1.7), 34 and HCOOH (3.8). 35 Our studies showed the high activity of the selected alkyl ammonium bromide salts in the Co(OAc) 2 system (entries 11−16).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…19−22 ILs have also been used as catalysts for these processes. 23 ILs attract a lot of attention due to their unique properties, such as the good solubility of polar and nonpolar compounds in them, their high thermal stability, high chemical activity, and resistance to oxygen oxidation. 24 Due to the low volatility of ILs, they do not form explosive mixtures with oxygen and air and therefore they are increasingly used as solvents in oxidation reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

Selective Aerobic Oxidation of Toluene in the Presence of Co²⁺ and Task-Specific Organic Salts, Including Ionic Liquids

Lisicki

Maciej

Orlińska

2021

Ind. Eng. Chem. Res.

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This paper presents research on the catalytic activity of systems composed of transition-metal compounds and organic bromide salts, [X][Br] or [X][Br 3 ], in the oxidation of toluene and its derivatives with oxygen using acetic acid as a solvent. Salts containing imidazolium, tetraalkylammonium, bromoalkylammonium, phenylalkylammonium, or benzylalkylammonium cations in combination with Co 2+ compounds were used. It was found that the [X][Br] and [X][Br 3 ] systems with Co 2+ compounds enabled the oxidation of toluene and its derivatives to the corresponding carboxylic acids with high selectivities and reaction rates. Moreover, long-term corrosion studies on three selected stainless steels showed that the organic salts that contained nitrogen atoms had an inhibitory effect on the corrosion caused by the Br − ions present in the reaction system. For the first time, the possibility of replacing inorganic bromides, used on an industrial scale in the Amoco process, by organic bromide salts, including ionic liquids, with corrosion-inhibiting properties was demonstrated.

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“…Imidazolium-based ILs were used as additives to a Co/NHPIcatalyzed system for the solvent-free aerobic oxidation of toluene under mild conditions in a study by Mahmood et al. [28] The partial oxidation of toluene with oxygen is a significant reaction for the production of benzaldehyde and benzoic acid. [29] This reaction is typically catalyzed by cobalt or manganese naphthenates being carried out in gas or liquid phase.…”

Section: Homogeneous N-hydroxyimides-based Systems With the Use Of Initiators/mediatorsmentioning

confidence: 99%

“…Adapted with permission from ref. [28]. Copyright (2018) Elsevier B.V. naphthoquinone (NQ), 2-methyl-1,4-naphthoquinone (MNQ), anthraquinone (AQ), and 2-ethyl-anthraquinone (EAQ) towards ethylbenzene oxidation reaction were assessed (Figure 1).…”

Section: Homogeneous N-hydroxyimides-based Systems With the Use Of Initiators/mediatorsmentioning

confidence: 99%

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

Andrade

Martins

2021

Eur J Org Chem

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The merging of organocatalysis and CÀ H bond oxyfunctionalization has demonstrated to be a powerful approach towards the development of new efficient and selective synthetic protocols. Both research areas have witnessed a tremendous growth over the past two decades, with a high number of studies mainly reporting the use of N-hydroxyphthalimide (NHPI) and related compounds in the selective oxyfunctionaliza-tion of hydrocarbons. Additionally, heterogeneous NHPI-based systems can provide a green and sustainable perspective for oxidation reactions. Nevertheless, reports related to this latter approach are still scarce and need further scouting in terms of types of supports used. This short review accounts for relevant contributions from 2010 onwards on the use of NHPI-based systems for hydrocarbon oxyfunctionalization.

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Cobalt/N-Hydroxyphthalimide(NHPI)-Catalyzed Aerobic Oxidation of Hydrocarbons with Ionic Liquid Additive

Cited by 33 publications

References 99 publications

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

Selective Aerobic Oxidation of Toluene in the Presence of Co²⁺ and Task-Specific Organic Salts, Including Ionic Liquids

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

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Cobalt/N-Hydroxyphthalimide(NHPI)-Catalyzed Aerobic Oxidation of Hydrocarbons with Ionic Liquid Additive

Cited by 33 publications

References 99 publications

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

Solvent‐Free Aerobic Oxidation of Ethylbenzene Promoted by NHPI/Co(II) Catalytic System: The Key Role of Ionic Liquids

Selective Aerobic Oxidation of Toluene in the Presence of Co2+ and Task-Specific Organic Salts, Including Ionic Liquids

Organocatalysis Meets Hydrocarbon Oxyfunctionalization: the Role of N‐Hydroxyimides

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Selective Aerobic Oxidation of Toluene in the Presence of Co²⁺ and Task-Specific Organic Salts, Including Ionic Liquids