2,4-Diaminotoluene → 2,3-Dinitrotoluene

HRID 2109872Notes

Reaction equation

HRID 2109872 reaction equation
[H][H].NC1C=C(N)C=CC=1C.NC1C=CC=C(N)C=1C.[N+:21]([C:24]1[CH:29]=[C:28]([N+]([O-])=O)[CH:27]=[CH:26][C:25]=1[CH3:33])([O-:23])=[O:22].[N+:34](C1C=CC=C([N+]([O-])=O)C=1C)([O-:36])=[O:35]>O>[N+:34]([C:29]1[C:24]([N+:21]([O-:23])=[O:22])=[C:25]([CH3:33])[CH:26]=[CH:27][CH:28]=1)([O-:36])=[O:35]

Participants

7

Reactant 5

HCID 72612,4-DiaminotolueneHCID 84612,4-DinitrotolueneHCID 118132,6-DinitrotolueneHCID 132052,6-ToluenediamineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 117612,3-Dinitrotoluene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An autoclave having a volume of 1000 ml and equipped with a gassing stirrer, a hydrogen supply pipe, an inlet pipe for the nitro compound and an outlet valve for excess hydrogen was used. The reaction mixture left the reactor through a frit, which retained the catalyst. The temperature in the reactor was regulated by means of an external heating or cooling circuit. A coiled cooling pipe inside the reactor provided additional cooling of the reaction mixture. 480 g of a commercial mixture comprising a mixture of 80% 2,4-diaminotoluene and 20% 2,6-diaminotoluene (TDA) with water in a weight ratio of TDA to water of 63:37 as well as 5.0 g-6.5 g of catalyst were placed in the reactor. The contents of the reactor were then placed under pressure by means of hydrogen and heated. At a temperature of 180° C. and a pressure of 26 bar, 125 g/h of a commercial mixture of 80% 2,4-dinitrotoluene and 20% 2,6-dinitrotoluene were passed into the reactor hourly and hydrogenation was carried out until the catalyst was exhausted. The resulting hydrogenation product was removed from the reactor continuously and worked up to form the pure diaminotoluene isomeric mixture.

Workup

  1. customequipped with a gassing stirrer
  2. waitThe reaction mixture left the reactor through a frit, which
  3. temperaturean external heating
  4. temperaturecooling circuit
  5. customA coiled cooling pipe inside the reactor provided additional
  6. temperaturecooling of the reaction mixture
  7. temperatureheated
  8. customThe resulting hydrogenation product was removed from the reactor continuously

Sources & evidence

ORD record
ord-3d472df5dd48489291000119c8e78a64
Source dataset
uspto-grants-2009_04
Patent number
US07517829B2

Reaction notes

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