The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

Zhang, Qunfeng; Su, Chang; Cen, Jie; Feng, Feng; Ma, Lei; Lu, Chunshan; Li, Xiaonian

doi:10.1016/j.cjche.2014.08.007

Cited by 14 publications

(10 citation statements)

References 23 publications

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“…Palladium is another frequently‐used precious metal catalyst with high catalytic activity for hydrogenation of CNB to the corresponding CAN [11, 15, 16]. Although compared with platinum, it is low‐cost, the hydrodechlorination reaction over the supported Pd catalysts is hard to avoid, resulting in a relative low selectivity to CAN [15].…”

Section: Introductionmentioning

confidence: 99%

“…Although compared with platinum, it is low‐cost, the hydrodechlorination reaction over the supported Pd catalysts is hard to avoid, resulting in a relative low selectivity to CAN [15]. Some efforts have been attempted to suppress the hydrodechlorination over the supported Pd catalysts, such as the modification of Sn 4+ [11] and diphenyl sulphide to Pd [16], and the combination of Pd and Au [2]. Those strategies all exhibited high selectivity to CAN, however, the supported Pd catalysts with an excellent performance is still a challenge.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Ying

Jang

et al. 2016

Micro & Nano Letters

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Pd-B amorphous alloy was successfully supported on the surface of natural nanoclay palygorskite (PAL) via a simple chemical reduction method. Compared with the conventional supported Pd catalyst, the Pd-B/PAL amorphous catalyst possessed the ultra-high selectivity (100%) to o-chloroaniline (o-CAN) in the hydrogenation of o-chloronitrobenzene (o-CNB) to o-CAN and avoided the dechlorination of o-CNB. XPS analysis results indicated that PAL support could reduce the electron density of Pd atoms and suppressed the hydrogenolysis of C-Cl bond. Meanwhile, the Pd-B/PAL amorphous catalyst exhibited a good stability and is a prospective catalyst for the selective hydrogenation of CNB to CAN.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Ying

Jang

et al. 2016

Micro & Nano Letters

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“…[1][2][3][4][5][6][7][8][9][10] However, these catalysts are not qualied to catalyse the selective hydrogenation of organic compounds with multiple reducible functionalities because of their very high activity. [1][2][3][4][5][6][7][8][9][10] However, these catalysts are not qualied to catalyse the selective hydrogenation of organic compounds with multiple reducible functionalities because of their very high activity.…”

Section: Introductionmentioning

confidence: 99%

“…Supported noble-metal catalysts are among the most industrially applied heterogeneous catalysts in various reductive reactions and have attracted extensive scientic interest. [1][2][3][4][5][6][7][8][9][10] However, these catalysts are not qualied to catalyse the selective hydrogenation of organic compounds with multiple reducible functionalities because of their very high activity. Therefore, modications of noble-metal catalysts for selective hydrogenation have been extensively applied in synthetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Preparation of supported core–shell structured Pd@Pd_xS_y/C catalysts for use in selective reductive alkylation reaction

Zhang

Feng

et al. 2015

RSC Adv.

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Supported noble-metal sulphide catalysts have attracted extensive scientific interest for their good selectivity in selective hydrogenation. However, the application of noble-metal catalysts is limited due to their lower activity, leading to harsh reaction conditions and poor conversion during hydrogenation reactions. In this study, Pd/C was sulphidized by H 2 S to prepare a series of core-shell structured Pd@Pd x S y /C catalysts, which were characterized by BET, EDS, XPS, XRD and CO chemisorption to investigate the influences of sulphidation temperature, sulphidation time and sulphidation atmosphere on the structure of the resulting catalysts. The sulphidation of Pd/C at low temperatures resulted in a core-shell structured catalyst, Pd@Pd x S y /C; with increasing sulphidation temperature, the size of Pd 0 as the core decreased, and the thickness of palladium sulphides as the shell increased correspondingly.When the sulphidation temperature reached 150 C, the resulting catalyst transformed to a complete palladium sulphide catalyst, Pd x S y /C. The structure of Pd@Pd x S y /C sulphidized at 30 C was independent of sulphidation time and sulphidation atmosphere. The sulphidized catalysts were applied to the reductive alkylation of PADPA and MIBK to DBPPD. The sulphidized catalysts presented a much higher selectivity for DBPPD compared with Pd/C, and Pd@Pd x S y /C showed higher activity than Pd x S y /C; moreover, the greater amount of Pd x S y content in the resulting catalyst led to a lower activity.

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“…Hydrogenolysis of the carbon-halogen bond is enhanced by the substitution of the amino group in the aromatic rings [6]. Many metal catalysts, such as Pt [7], Pd [8,9], Ru [10], and Ni [11,12], are used in this reaction. On one hand, Raney nickel is widely used in this hydrogenation reaction [11,12], but considering the selectivity, it is necessary to add an donating compound such as morpholine as an inhibitor [4].…”

Section: Introductionmentioning

confidence: 99%

Morpholine-Modified Pd/γ-Al2O3@ASMA Pellet Catalyst with Excellent Catalytic Selectivity in the Hydrogenation of p-Chloronitrobenzene to p-Chloroaniline

Wang

Thapa

et al. 2017

Catalysts

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An amino poly (styrene-co-maleic anhydride) polymer (ASMA) encapsulated γ-Al 2 O 3 pellet material has been synthesized successfully. After loading with Pd species and modified with morpholine, the inorganic-organic hybrid material shows an excellent catalytic property in the selective hydrogenation of p-chloronitrobenzene (p-CNB) to p-chloroaniline (p-CAN). In this procedure, morpholine can connect with the polymer layer in a form of amide bond and acts as an unparalleled immobilized dechlorination inhibitor, which can avoid further dechlorination efficiently and keeps stability due to the repulsive effect from the surviving C-O-C bond. The catalyst as prepared was characterized by using XRD, TGA, SEM, TEM, FT-IR, and ICP-OES, and it was further tested in the selective hydrogenation of p-CNB. It shows a supreme catalytic activity (almost 100%) and selectivity (up to 99.51%) after recycling for even 10 times, much superior to the blank alumina supported palladium (47.09%).

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The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

Cited by 14 publications

References 23 publications

Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Preparation of supported core–shell structured Pd@Pd_xS_y/C catalysts for use in selective reductive alkylation reaction

Morpholine-Modified Pd/γ-Al2O3@ASMA Pellet Catalyst with Excellent Catalytic Selectivity in the Hydrogenation of p-Chloronitrobenzene to p-Chloroaniline

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The Modification of Diphenyl Sulfide to Pd/C Catalyst and Its Application in Selective Hydrogenation of p-Chloronitrobenzene

Cited by 14 publications

References 23 publications

Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Preparation of Pd–B/palygorskite amorphous catalyst for the selective hydrogenation of o ‐chloronitrobenzene to o ‐chloroaniline

Preparation of supported core–shell structured Pd@PdxSy/C catalysts for use in selective reductive alkylation reaction

Morpholine-Modified Pd/γ-Al2O3@ASMA Pellet Catalyst with Excellent Catalytic Selectivity in the Hydrogenation of p-Chloronitrobenzene to p-Chloroaniline

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Preparation of supported core–shell structured Pd@Pd_xS_y/C catalysts for use in selective reductive alkylation reaction