Hydrazine as a Reducing Agent for Organic Compounds (Catalytic Hydrazine Reductions)

Furst, Arthur; Berlo, Robert C.; Hooton, Shirley

doi:10.1021/cr60233a002

Cited by 295 publications

(119 citation statements)

References 69 publications

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“…The nitro groups contain N atoms in a planar environment with N-C bond lengths of 149. The nitro functionalities of 3 were converted into amino groups with hydrazine hydrate in the presence of a Pd/C catalyst system [30]. Tetradentate meso-1,4-diamino-2,3-di(2-pyridyl)butane 4 was isolated from this reduction reaction with a yield of 76 %.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Kloubert

Schulz

Görls

et al. 2009

Zeitschrift Für Naturforschung B

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In a Henry-type reaction nitromethane reacts with N-(2-pyridylmethylidene)-methylamine (1) yielding 1-methylamino-1-(2-pyridyl)-2-nitromethane (2) in nearly quantitative yield. This orange compound decomposes slowly in an inert gas atmosphere and fast in contact with air. Therefore 2 has to be stored at −78 • C as a methanol solution. Reduction of 2 with hydrogen in the presence of a Pd/C catalyst leads to the formation of 1,4-dinitro-2,3-di(2-pyridyl)butane (3) in the rather poor yield of 12 %. The major product is the meso-isomer, meso-3, whereas only traces of (R, R)-and (S, S)-isomers of 3 are formed. A conversion of the nitro groups into amino functionalities succeeds with hydrazine hydrate in the presence of a Pd/C catalyst yielding meso-1,4-diamino-2,3-di(2-pyridyl)butane (4). Recrystallization from an aqueous solution gives 4·2H 2 O. The zinc(II) chloride complex 5 with the metal atoms in distorted tetrahedral environments can be isolated after addition of two equivalents of ZnCl 2 to 4. The molecular structures of trimeric 1, meso-3, (R, R)/(S, S)-3, meso-4, and 5 have been determined and are discussed.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Kloubert

Schulz

Görls

et al. 2009

Zeitschrift Für Naturforschung B

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“…Carbon can serve as an adsorbent and an electrical conductor [8,11] and these functions should be taken into account to discuss the above-mentioned impact of the surface modifications of AC on its catalytic performance. The present AC-derived materials can be a catalyst for the reduction of nitrobenzene and 3-nitrostyrene by hydrazine but not for styrene; the doping of oxygen and nitrogen species promotes the reduction of nitro groups but the reduction of vinyl group of vinylaniline is suppressed by the presence of surface nitrogen species, resulting in an increase in its selectivity.…”

Section: Implication Of Surface Hetero Dopants In the Reductionmentioning

confidence: 99%

“…Beier et al used supported platinum particles for reduction of 3-nitrostyrene by hydrogen and showed that the selectivity to vinylaniline was enhanced in the presence of basic ionic liquid, which suppressed its further hydrogenation to ethylaniline [20], similar to the present treated AC surface of basic nature. [8,12,14] Probably, those effects on the adsorption of the substrates and the reactivity of the reducing agent would be responsible for the catalytic performance of nitrogen-and oxygen-doped AC materials in the chemoselective hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene. It is interesting that the doping of hetero atoms to the surface of carbon-based catalysts, which produces polar sites (C-N, C-O) on their surface, is an effective way in promoting organic synthetic reactions and controlling their product distribution patterns.…”

Section: Implication Of Surface Hetero Dopants In the Reductionmentioning

confidence: 99%

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Nitrogen and oxygen-doped metal-free carbon catalysts for chemoselective transfer hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene with hydrazine

Fujita

Watanabe

Katagiri

et al. 2014

Journal of Molecular Catalysis A: Chemical

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An activated carbon (AC) was treated by hydrogen peroxide and ammonia to dope oxygen and nitrogen on its surface. The surface-functionalized AC catalysts were used for the transfer reduction of nitrobenzene, styrene, and 3-nitrostyrene by hydrazine hydrate. The reduction of nitrobenzene and 3-nitrostyrene was promoted over the oxygen-and nitrogen-doped catalysts compared to the parent AC catalyst. Those were less active for the reduction of styrene but active for the reduction of vinyl group of 3-nitrostyrene. However, the nitrogen dopant suppressed the reduction of vinyl group of 3-vinylaniline. The functionalized AC catalysts are likely to facilitate the adsorption and activation of nitro group of the nitro substrates through interactions with polarized surface induced by the oxygen and nitrogen hetero dopants. This should make it possible to reduce the vinyl group of 3-nitrostyrene on the surface. The nitrogen dopant hindered the reduction of the vinyl group of 3-vinylaniline because the adsorption through its amino group should become difficult on the surface of basic nature induced by the nitrogen doping. The AC serves as an electrical conductor and its performance should be enhanced by the surface functionalization and this would contribute to the formation of reducing species such as diimide and proton from hydrazine on the surface.The present results show that oxygen-and/or nitrogen-doped, functionalized carbon materials could be promising as metal-free multi-task catalysts.

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“…162 Hydrazine as a reducing agent for the conversion of nitroaromatic compounds to aromatic amines has been investigated. 163 The hydrazine reduction of nitrobenzene follows the overall reaction:…”

Section: Reduction Of Nitrobenzene By Hydrazinementioning

confidence: 99%

Create a Consortium and Develop Premium Carbon Products from Coal

Rusinko¹,

Andrésen²,

Hill³

et al. 2006

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The objective of these projects was to investigate alternative technologies for non-fuel uses of coal. Special emphasis was placed on developing premium carbon products from coal-derived feedstocks. A total of 14 projects, which are the 2003 Research Projects, are reported herein. These projects were categorized into three overall objectives. They are:(1) To explore new applications for the use of anthracite in order to improve its marketability; (2) To effectively minimize environmental damage caused by mercury emissions, CO 2 emissions, and coal impounds; and (3) To continue to increase our understanding of coal properties and establish coal usage in non-fuel industries.Research was completed in laboratories throughout the United States. Most research was performed on a bench-scale level with the intent of scaling up if preliminary tests proved successful.These projects resulted in many potential applications for coal-derived feedstocks. These include:• Use of anthracite as a sorbent to capture CO 2 emissions • Use of anthracite-based carbon as a catalyst • Use of processed anthracite in carbon electrodes and carbon black • Use of raw coal refuse for producing activated carbon • Reusable PACs to recycle captured mercury • Use of combustion and gasification chars to capture mercury from coal-fired power plants • Development of a synthetic coal tar enamel • Use of alternative binder pitches in aluminum anodes • Use of Solvent Extracted Carbon Ore (SECO) to fuel a carbon fuel cell • Production of a low cost coal-derived turbostratic carbon powder for structural applications • Production of high-value carbon fibers and foams via the co-processing of a low-cost coal extract pitch with well-dispersed carbon nanotubes • Use of carbon from fly ash as metallurgical carbon • Production of bulk carbon fiber for concrete reinforcement • Characterizing coal solvent extraction processes Although some of the projects funded did not meet their original goals, the overall objectives of the CPCPC were completed as many new applications for coal-derived feedstocks have been researched. Future research in many of these areas is necessary before implementation into industry. Potential Application for Exfoliated Anthracite: Filler in CathodesThe Pennsylvania State University -Subcontract # 2486-TPSU-DOE-0350…………….19 Use of Coal Gasification and Combustion Chars for Mercury CaptureThe Pennsylvania State University -Subcontract # 2482-TPSU-DOE-0350…………….46 Binding Efficiency of Coal-Derived Binders Towards Anode ButtsThe EXECUTIVE SUMMARYThe objective of these projects was to investigate alternative technologies for non-fuel uses of coal. Special emphasis was placed on developing premium carbon products from coal-derived feedstocks. A total of 14 projects, which are the 2003 Research Projects, are reported herein. These projects were categorized into three overall objectives. They are:(1) To explore new applications for the use of anthracite in order to improve its marketability; (2) To effectively minimize environmenta...

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Hydrazine as a Reducing Agent for Organic Compounds (Catalytic Hydrazine Reductions)

Cited by 295 publications

References 69 publications

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Nitrogen and oxygen-doped metal-free carbon catalysts for chemoselective transfer hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene with hydrazine

Create a Consortium and Develop Premium Carbon Products from Coal

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