Kinetic and mechanistic investigations of chlorocomplex of Ru(III) and Ir(III) catalyzed oxidation of d -fructose by N-bromophthalimide in acidic medium

Sachdev, Neerja; Singh, Ajaya Kumar; Shrivastava, Alpa; Katre, Yokraj

doi:10.1016/j.jscs.2012.12.006

Cited by 8 publications

(5 citation statements)

References 38 publications

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“…NBP possesses a highly polar N–Br bond in the lines of other its structural analogue NBS. In view of this, NBP has been reported as a good oxidizing and brominating agent by earlier workers . Thus in aqueous acetic acid solutions, NBP may exist as free NBP, protonated NBP (i.e., NBPH + ), HOBr, Br + , in the lines of its structural analogue NBS according to the following equilibria:

NBP + {normalH}_{2} O ⇌ HOBr + NHP

NBP + H^{+} ⇌ NHP + B r^{+}

NBP + H^{+} ⇌ {(NBPH)}^{+}

HOBr + H^{+} ⇌ {({normalH}_{2} OBr)}^{+}

…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, kinetics, and mechanism of bromophenols by N‐bromophthalimide in aqueous acetic acid

Anjaiah

Prameela

Srinivas

et al. 2018

Int J of Chemical Kinetics

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The kinetics and mechanism of bromination of phenol and its substituents, viz. 4‐chlorophenol, 4‐bromophenol, 4‐methylphenol, and 4‐methoxyphenol by N‐bromophthalimide (NBP) in the presence of mercuric acetate in the temperature range of 303–318 K in aqueous acetic acid medium have been investigated. The reaction follows first‐order dependence on [NBP] and fractional order dependence of rate on [Phenol]. The activation parameters have been evaluated, and based on the observed kinetic results the probable mechanism has been proposed. Observed kinetic features and Hammett's reaction constant (ρ) suggests that bromination occurs through electrophilic substitution of bromonium ion (Br+) into the aromatic ring in the transition state. Large negative entropy of activation values probably suggests the rigid nature of transition state.

show abstract

NBP + {normalH}_{2} O ⇌ HOBr + NHP

NBP + H^{+} ⇌ NHP + B r^{+}

NBP + H^{+} ⇌ {(NBPH)}^{+}

HOBr + H^{+} ⇌ {({normalH}_{2} OBr)}^{+}

…”

Section: Resultsmentioning

confidence: 99%

“…In view of this, NBP has been reported as a good oxidizing and brominating agent by earlier workers. [21][22][23][24][25][26] Thus in aqueous acetic acid solutions, NBP may exist as free NBP, protonated NBP (i.e., NBPH + ), HOBr, Br + , in the lines of its structural analogue NBS according to the following equilibria:…”

Section: Reactive Species and Mechanismmentioning

confidence: 99%

Synthesis, kinetics, and mechanism of bromophenols by N‐bromophthalimide in aqueous acetic acid

Anjaiah

Prameela

Srinivas

et al. 2018

Int J of Chemical Kinetics

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“…By literature, we found several articles on the oxidation of several organic compounds NBP in transition metal catalyzed system in acidic and alkaline medium, i.e., d-glucose [76,77], d-fructose [78], glycine [79,80], valine [81][82][83], β-alanine [84], leucine [85], d-arabinose [86].…”

Section: Oxidation Of Organic Compound By Nbp (Transition Metal Ions Catalyzed)mentioning

confidence: 99%

Oxidative behavior of N-bromophthalimide for organic compounds: a review

Jain¹,

Negi

Singh³

2018

SN Appl. Sci.

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Organic compounds receive from industries as effluents are highly toxic and hazardous for the environment. Conventional oxidation process for the oxidation of organic compounds through use of N-bromophthalimide (NBP) is one of the significant process for conversion of organic compounds into environmental friendly or less harmful substances. The main scenario of this review is oxidation and kinetics of different organic compounds by NBP with different experimental methods-iodometric and potentiometric along with uncatalyzed, and catalyzed system. In addition to this we also summarize synthesis, properties and reactive species of NBP. Oxidation products obtained by oxidation of various organic compounds by NBP were acetic acid, aldehyde, carbon dioxide, ammonia, cyanide, aldonic acid etc. Present review, first time offers all aspects of NBP as an oxidizing agent for oxidation of organic compounds.

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“…Furfural is a high-value furan aldehyde, with a wide range of industrial uses, especially in the production of pharmaceuticals, polymers, resins, solvents, fine chemicals, fuel additives, and biofuels [1][2][3][4]. Xylose is an encouraging feedstock for furfural synthesis because of the process simplicity and product selectivity [5,6].…”

Section: Introductionmentioning

confidence: 99%

Catalytic Conversion of Xylose to Furfural by p-Toluenesulfonic Acid (pTSA) and Chlorides: Process Optimization and Kinetic Modeling

et al. 2021

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Furfural is one of the most promising precursor chemicals with an extended range of downstream derivatives. In this work, conversion of xylose to produce furfural was performed by employing p-toluenesulfonic acid (pTSA) as a catalyst in DMSO medium at moderate temperature and atmospheric pressure. The production process was optimized based on kinetic modeling of xylose conversion to furfural alongwith simultaneous formation of humin from xylose and furfural. The synergetic effects of organic acids and Lewis acids were investigated. Results showed that the catalyst pTSA-CrCl3·6H2O was a promising combined catalyst due to the high furfural yield (53.10%) at a moderate temperature of 120 °C. Observed kinetic modeling illustrated that the condensation of furfural in the DMSO solvent medium actually could be neglected. The established model was found to be satisfactory and could be well applied for process simulation and optimization with adequate accuracy. The estimated values of activation energies for xylose dehydration, condensation of xylose, and furfural to humin were 81.80, 66.50, and 93.02 kJ/mol, respectively.

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Kinetic and mechanistic investigations of chlorocomplex of Ru(III) and Ir(III) catalyzed oxidation of d -fructose by N-bromophthalimide in acidic medium

Cited by 8 publications

References 38 publications

Synthesis, kinetics, and mechanism of bromophenols by N‐bromophthalimide in aqueous acetic acid

Synthesis, kinetics, and mechanism of bromophenols by N‐bromophthalimide in aqueous acetic acid

Oxidative behavior of N-bromophthalimide for organic compounds: a review

Catalytic Conversion of Xylose to Furfural by p-Toluenesulfonic Acid (pTSA) and Chlorides: Process Optimization and Kinetic Modeling

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