2,4-Dinitrophenol → 2,4-Diaminophenol

HRID 2285618Notes

Reaction equation

HRID 2285618 reaction equation
[H][H].[N+:3]([C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[OH:15])([O-])=O>[Pd].[Rh].O>[NH2:3][C:6]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:7]=1[OH:15]

Participants

6

Reactant 2

HCID 14932,4-DinitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 72662,4-DiaminophenolYield 102.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23948RhodiumCatalystHCID 962WaterSolvent

Conditions

Temperature
116 °C

Procedure

Onto the bottom of a cylindrical reactor a chamber is placed which is made of a 100μ-thick foil having the working surface area of 50 cm2. The foil is manufactured of an alloy consisting of 95% by mass of palladium and 5% by mass of rhodium. Hydrogen is continuously fed inside the chamber under the pressure 2.5 atm at the rate of 10 ml/min. Outside the chamber in the reactor there are placed 22 g of 2,4-dinitrophenol, whereafter 250 ml of distilled water are added thereto. The reactor is heated to the temperature of 116° C., pressure inside the reactor is increased to 4 atm; under these conditions the process of hydrogenation is conducted under stirring for 3 hours. Then the reactor is cooled and the precipitated crystals are filtered-off to give 15.2 g of 2,4-diaminophenol. The product is recrystallized from acetone to give 10.3 g of 2,4-diaminophenol with the melting point of 80° C. The yield of 2,4-diaminophenol is 71.6% of the theoretical (i.e. as calculated for the initial 2,4-dinitrophenol).

Workup

  1. customOnto the bottom of a cylindrical reactor a chamber is placed
  2. temperatureis increased to 4 atm
  3. temperatureThen the reactor is cooled

Sources & evidence

ORD record
ord-becb0d7b9c1e4454968c51125d590fea
Source dataset
uspto-grants-1982_04
Patent number
US04323708

Reaction notes

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