Oxidation of methyl phenyl sulfide, diphenyl sulfide and styrene by oxovanadium(IV) and copper(II) complexes of NS donor ligand encapsulated in zeolite-Y

Maurya, Mannar R.; Chandrakar, Anil Kumar; Chand, Shri

doi:10.1016/j.molcata.2007.08.021

Cited by 43 publications

(14 citation statements)

References 26 publications

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“…The reason for lower selectivity at higher amount of catalyst may be due to two reactants adsorbed or chemisorbed on different catalyst particles. Thus, reducing the chance to interact between the two reactants, leading to a decrease in selectivity [23] . However, increasing the catalyst amount from 5 mg to 20 mg, the cyclooctene conversion can be significantly raised from 82.7 to 99.4 %.…”

Section: Resultsmentioning

confidence: 99%

Bimetallic‐organic Frameworks CoMo‐ZIF‐67: An Efficient and Stable Catalyst for Selective Oxidation of Alkenes

et al. 2020

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Developing catalysts for the selective oxidation of alkenes with environment‐friendly, unique structural characteristics, high economic benefit and better catalytic performance is important. Herein, we employed ZIF‐67 as the sacrificial template to synthesize bimetallic‐organic frameworks CoxMo100‐x‐ZIF nanocages by a facile dissolution‐regrowth strategy. The Co51.8Mo48.2‐ZIF catalyst was tested under various experimental parameters for the selective oxidation of cyclooctene to screen the optimal reaction conditions. Under the optimal reaction conditions, Co51.8Mo48.2‐ZIF nanocages exhibited a high cyclooctene conversion of 99.3 % and a selectivity of 99.0 % to epoxy cyclooctane. Furthermore, Co51.8Mo48.2‐ZIF nanocages can maintain their catalytic performance after reused five catalytic cycles. This bimetallic catalyst could also be used for the epoxidation of a wide range of alkenes, such as hexene or cyclohexene. In addition, the kinetic studies were conducted, and a reasonable reaction mechanism was proposed based on density functional theory calculations. The outstanding catalytic performance of CoxMo100‐x‐ZIF nanocages can be attributed to the cooperativity between Co and Mo sites and the hollow structure with high surface areas.

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Section: Resultsmentioning

confidence: 99%

Bimetallic‐organic Frameworks CoMo‐ZIF‐67: An Efficient and Stable Catalyst for Selective Oxidation of Alkenes

et al. 2020

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“…3 It gives a good yield, but the method is complex and tedious. Ph 2 SO, on the other hand, is usually made by catalytic oxidation of Ph 2 S. 4,5 The preparation often suffers with overoxidation to the diphenyl sulfone (Ph 2 SO 2 ) side product. In order to overcome this difficulty, a different method was developed by the reaction of Ph 2 S with sulfuryl chloride (SO 2 Cl 2 ), which gives moderate yield of Ph 2 SO after crystallization.…”

Section: Introductionmentioning

confidence: 99%

Formation of Diphenyl Sulfoxide and Diphenyl Sulfide via the Aluminum Chloride–Facilitated Electrophilic Aromatic Substitution of Benzene with Thionyl Chloride, and a Novel Reduction of Sulfur (IV) to Sulfur (II)

Sun

Haas

Sayre

et al. 2010

Phosphorus, Sulfur, and Silicon and the Related Elements

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The aluminum chloride (AlCl 3 )-facilitated electrophilic aromatic substitution (EAS) reaction of benzene (PhH) with thionyl chloride (SOCl 2 ) in the molar ratio of PhH:SOCl 2 :AlCl 3 = 2:1:1 was studied under different conditions. At about 70 • C, adding granular AlCl 3 (equimolar to SOCl 2 ) piecewise to a 2:1 mixture of PhH and SOCl 2 led to formation of a highly pure (99.9%) sole product of diphenyl sulfoxide (Ph 2 SO) in an isolated yield of 85% after aqueous workup. It represents a simple and very efficient synthesis of Ph 2 SO, an important fundamental organic reagent. At about 0 • C, adding PhH (twice the molar quantity of SOCl 2 ) to a 1:1 mixture of SOCl 2 and AlCl 3 gave both diphenyl sulfide Ph 2 S (yield: 37%) and Ph 2 SO (yield: 27%) after aqueous workup, together with a small amount of S-phenyl benzenesulfonothioate PhSO 2 SPh (yield: about 5%) and a trace amount of diphenyl sulfone (Ph 2 SO 2 ). A possible mechanism has been proposed to account for formation of all these products, especially for the formation of Ph 2 S [S (II)] from SOCl 2 [S (IV)], which involves a novel reduction of sulfur in the course of the EAS reaction.

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“…The MCl 3 -(M=Cl and Fe)-catalysed reactions of SeOCl 2 with benzene were apparently much slower than the AlCl 3 -catalysed reaction of SOCl 2 with benzene at the same temperature, which was indicated by much slower rate of bubbling in the SeOCl 2 reactions. The products from MCl 3 -(M=Al and Fe)-catalysed reactions of benzene with SeOCl 2 were characterised by GC-MS, showing that two compounds, diphenyl selenide (Ph 2 Se) and diphenyl diselenide (PhSeSePh), were produced in each reaction in different molar percentages [Eqn (7)], which were established by examining the GC peak areas according to Eqn (8). The initially expected diphenyl selenoxide (Ph 2 SeO) was not identified by GC-MS in either of the reaction products.…”

Section: Aluminium-chloride-(alcl 3 )-And Iron(iii)-chloride-(fecl 3 mentioning

confidence: 99%

Investigations on the Lewis-Acids-Catalysed Electrophilic Aromatic Substitution Reactions of Thionyl Chloride and Selenyl Chloride, the Substituent Effects, and the Reaction Mechanisms

Sun

Haas

McWilliams

et al. 2013

Journal of Chemical Research

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The previously established aluminium-chloride-(AlCl 3 )-catalysed electrophilic aromatic substitution (EAS) of benzene (PhH) with thionyl chloride (SOCl 2 ) has been extended to toluene (PhCH 3 ), chlorobenzene (PhCl), and phenol (PhOH). -CH 3 was found to be mainly a para-director with a minor ortho-directing effect on the EAS reactions giving diaryl sulfoxides (Ar 2 SO). -Cl was found to be exclusively a para-director for formation of Ar 2 SO. All the -CH 3 , -Cl, and -OH groups were shown to be exclusive para-directors for formation of diaryl sulfides (Ar 2 S) from the EAS reactions. Although the reactions of PhH and PhCH 3 with SOCl 2 in the presence of AlCl 3 gave the major Ar 2 SO and minor Ar 2 S at ambient temperature, the phenol (PhOH) reaction was shown to give only the reduced sulfide (p-HOC 6 H 4 ) 2 S with no sulfoxide (p-HOC 6 H 4 ) 2 SO formed. The mixed diaryl sulfoxides ArSOAr′ (Ar, Ar′=C 6 H 5 , p-CH 3 C 6 H 4 ; C 6 H 5 , o-CH 3 C 6 H 4 ; and C 6 H 5 , p-ClC 6 H 4 ) were produced in the AlCl 3 -catalysed reactions of SOCl 2 with molar 1:1 PhH-PhX mixtures (X=CH 3 and Cl). Efforts to enhance the yield of S-aryl arenesulfonothioates ArSO 2 SAr (Ar=Ph, p-CH 3 C 6 H 4 , and p-ClC 6 H 4 ) from the AlCl 3 -catalysed EAS reactions of SOCl 2 were made, showing that decreasing the molar ratios of ArH/SOCl 2 or lowering the temperature resulted in an increase in the product yield. A detailed mechanism has been proposed to account for the formation of ArSO 2 SAr. The Lewis-acid-MCl 3 -(M=Al and Fe)-catalysed EAS reactions of PhH with selenyl chloride (SeOCl 2 ) were demonstrated to give the reduced diphenyl selenide (Ph 2 Se) and diphenyl diselenide (PhSeSePh) via novel auto-redox processes in selenium of the key EAS intermediates.

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Oxidation of methyl phenyl sulfide, diphenyl sulfide and styrene by oxovanadium(IV) and copper(II) complexes of NS donor ligand encapsulated in zeolite-Y

Cited by 43 publications

References 26 publications

Bimetallic‐organic Frameworks CoMo‐ZIF‐67: An Efficient and Stable Catalyst for Selective Oxidation of Alkenes

Bimetallic‐organic Frameworks CoMo‐ZIF‐67: An Efficient and Stable Catalyst for Selective Oxidation of Alkenes

Formation of Diphenyl Sulfoxide and Diphenyl Sulfide via the Aluminum Chloride–Facilitated Electrophilic Aromatic Substitution of Benzene with Thionyl Chloride, and a Novel Reduction of Sulfur (IV) to Sulfur (II)

Investigations on the Lewis-Acids-Catalysed Electrophilic Aromatic Substitution Reactions of Thionyl Chloride and Selenyl Chloride, the Substituent Effects, and the Reaction Mechanisms

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