Ethanol → Sulfuric Acid

HRID 1393838Notes

Reaction equation

HRID 1393838 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].[OH2:22].C([OH:25])C>[Zn]>[S:16]([OH:18])([OH:25])(=[O:17])=[O:22].[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:6][CH:5]=1.[S:16]([O-:18])([O-:25])(=[O:17])=[O:22].[S:16](=[O:18])(=[O:25])([OH:17])[OH:22]

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 58586708HCID 58586708, compound

Product 3

HCID 1117Sulfate IonHCID 1118Sulfuric AcidYield 96%HCID 69205091HCID 69205091, compound

Reagents, catalysts & solvents 1

HCID 23994ZincSolvent

Procedure

25.6 g (0.0891 mol) of N-[4-(4-nitrophenylamino)butyl]methanesulfonamide (26) were hydrogenated in a mixture of 49 g of zinc powder, 1.6 g of ammonium chloride, 24 mL of water, and 135 mL of ethanol brought to reflux. After suction-filtering of the slurry, the para-phenylenediamine was isolated in the form of a sulfate by addition of 8.1 mL of 96% sulfuric acid. After filtration and drying, 31.3 g of grey product were obtained.

Workup

  1. temperatureto reflux
  2. filtrationAfter suction-filtering of the slurry

Sources & evidence

ORD record
ord-7c700f5d3aba414cb44e496ee84f3aac
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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