Amination by Reduction

Werner, Jesse

doi:10.1021/ie50465a005

Cited by 11 publications

(4 citation statements)

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“…In the process of making the final ethyl 3-(2', 4'dihydroxyphenylazo)benzoate, many problems with the synthesis have been encountered, mainly regarding the protection of the very reactive acidic proton on benzoic acid derivates used. The first problem with the carboxylic proton at 3-aminobenzoic acid came at the nitro-group reduction step; having much lower yield and separation of resulting product wasn't possible when either iron or tin were used as reducing agents [15]. That was most likely due to the formation of iron and tin complexes with the product and possible carboxylate-amine polymerization.…”

Section: Discussionmentioning

confidence: 99%

Azo dyes synthesis demonstrations for education purposes

Verner

2023

JASB

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Practical organic chemistry is one of the least accessible subjects to study in high school laboratories, due to high cost demands on organic chemicals and equipement. The objective of this project was to design and carry out an easily replicable synthesis for students to try out or for educators to demonstrate. The resulting 4-step 5-reaction synthesis, which uses well-known as well as alternative reactions, but only cheap and accessible reagents produces a diazonium dye which can be demonstrated by its pH-measuring properties.

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Section: Discussionmentioning

confidence: 99%

Azo dyes synthesis demonstrations for education purposes

Verner

2023

JASB

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“…review summarizes significant information which has become available in the past decade about hydrogenation as a unit process. Coal hydrogenation, and reduction and alkylation of nitrogen compounds by hydrogenation have been the subject of recent reviews and are not covered in this paper (227,248,266,267).…”

Section: Thismentioning

confidence: 99%

Hydrogenation and Hydrogenolysis

O'Boyle¹

1950

Ind. Eng. Chem.

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“…Aminoarenes have been produced industrially by the reduction of nitroarenes using Bechamp reduction, which requires Fe and hydrochloric acid as catalysts. [4] Because the Bechamp reduction reaction requires a stoichiometric reducing agent and generates a large amount of waste, heterogeneous catalysts that promote the chemoselective hydrogenation of nitro compounds is desirable from the perspective of green chemistry.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Hydrogenation of Nitroarenes Using Ni−Fe Alloy Catalysts at Ambient Pressure

et al. 2021

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NiÀ Fe alloy catalysts have been used to achieve high activity and selectivity toward the hydrogenation of nitroarenes to aminoarenes. 4-Nitrostyrene hydrogenation using a series of Ni-based bimetallic alloys and intermetallic compounds supported on SiO 2 revealed that NiÀ Fe alloy catalysts exhibit higher Turnover frequency (TOF) than Ni monometal catalysts with almost similar nanoparticle size. Furthermore, nitroselective hydrogenation under atmospheric hydrogen was observed, which has never been reported using conventional Ni catalysts. XRD and XAFS measurements revealed that both Ni and Fe were reduced to their metallic states by pretreatment under hydrogen flow at 400°C. Kinetic experiments suggested that the formation of NiÀ Fe alloy promoted the adsorption of the nitro group and suppressed the hydrogenation of the vinyl group. TOF and selectivity for 4-nitrostyrene hydrogenation increased by reducing nanoparticle sizes, indicating that the metal-support interfaces interacted with 4-nitrostyrene. Theoretical calculations suggested that the addition of Fe enhanced the co-adsorption of dissociated hydrogen and the nitro group.

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Amination by Reduction

Cited by 11 publications

References 1 publication

Azo dyes synthesis demonstrations for education purposes

Azo dyes synthesis demonstrations for education purposes

Hydrogenation and Hydrogenolysis

Chemoselective Hydrogenation of Nitroarenes Using Ni−Fe Alloy Catalysts at Ambient Pressure

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