Hydrazobenzene → Azobenzene

HRID 2164382

Reaktionsgleichung

Reaktionsgleichung von HRID 2164382
[NH:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>[Pd]>[NH2:1][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:1]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[N:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 31222HydrazobenzeneHCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 2272AzobenzeneHCID 6115Aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

It has now been found that the abovementioned disadvantages are avoided when the aryldiazosulfonates are catalytically hydrogenated. There is apparently a prejudice against this means of reduction, since even though a large number of reducing agents have been proposed for this purpose (Houben-Weyl, loc. cit. 180 to 223), catalytic hydrogenation has not been considered, presumably because reducing agents which can convert a nitro group into the amino group cleave aromatic hydrazo compounds to give the amines (Houben-Weyl, 11/1, 522). Thus hydrazobenzene in the presence of palladium black, even in the absence of hydrogen, disproportionates to give aniline and azobenzene. Hydrogenation in the presence of nickel produces aniline in virtually quantitative yield. Under the same conditions, phenylhydrazine readily decomposes to give aniline and ammonia (Houben-Weyl, loc.cit. 538).

Quellen und Nachweise

ORD-Eintrag
ord-c6b0097aa71142f58cba5d8b4ccfa66e
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04504424

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