2,4-Diaminotoluene → 4-tert-Butyl-6-methylbenzene-1,3-diamine

HRID 2309169Notes

Reaction equation

HRID 2309169 reaction equation
[C:1]1([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]([NH2:7])=[CH:5][CH:6]=1.[CH3:10][C:11](=[CH2:13])[CH3:12]>>[C:11]([C:5]1[CH:6]=[C:1]([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]=1[NH2:7])([CH3:12])([CH3:10])[CH3:13]

Participants

3

Reactant 2

HCID 72612,4-DiaminotolueneHCID 8255Isobutylene

Product 1

HCID 139327594-tert-Butyl-6-methylbenzene-1,3-diamine

Conditions

Temperature
180 °C

Procedure

The procedure of Example 1 was followed to produce toluenediamine (5tBTDA) by using 15 grams of powdered montmorillonite clay in place of the silica-alumina catalyst and using 150 g (1.23 moles) of the 2,4-toluenediamine isomer as opposed to the 2,6-isomer. As in Example 1, the reaction contents were purged with nitrogen and then the contents were heated to 180° C. with stirring. Approximately 278 grams or 4.95 moles of isobutylene were then added to the reaction mixture over 20 minutes. The initial reaction pressure increased to 1210 psig and the contents maintained 180° C. for 23 hours. At that time the contents were cooled 150° C. and the reactor vented. The catalyst then was removed by hot filtration.

Workup

  1. customAs in Example 1, the reaction contents
  2. customwere purged with nitrogen
  3. customThe initial reaction pressure
  4. temperatureincreased to 1210 psig
  5. temperaturethe contents maintained 180° C. for 23 hours
  6. temperatureAt that time the contents were cooled 150° C.
  7. customThe catalyst then was removed by hot filtration

Sources & evidence

ORD record
ord-4ba416dc7a0f4174bb96b013d30ad939
Source dataset
uspto-grants-1987_09
Patent number
US04693837

Reaction notes

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