Isobutylene → Isobutylene

HRID 649659Notes

Reaction equation

HRID 649659 reaction equation
[C:1]([C:5]1([NH2:13])[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][CH:6]1[CH3:12])([CH3:4])([CH3:3])[CH3:2].C1(C)C(N)=CC=CC=1N.CC(=C)C>>[CH3:3][C:1](=[CH2:2])[CH3:4].[C:6]1([CH3:12])[CH:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:5]=1[NH2:13]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 132052,6-ToluenediamineHCID 68115044HCID 68115044, compound

Product 2

HCID 8255IsobutyleneHCID 175932,3-Diaminotoluene

Conditions

Temperature
200 °C

Procedure

Synthesis of the above recited ortho-tert-butyltoluenediamine was carried out in a 1 gallon stainless steel pressure vessel equipped with a mechanical stirrer. The vessel was charged with a 150 gram portion of a powdered commercially available silica-alumina catalyst containing 13% alumina and 1500 grams (12.24 moles) of 2,6-toluenediamine. The autoclave was sealed and purged with nitrogen. A residual blanket of nitrogen was left in the autoclave, leaving the pressure at 16 psig. The contents of the reactor were heated to a temperature of 200° C. with constant agitation. Isobutylene was then introduced into the reactor and 870 grams or 15.5 moles were added over a 30 minute period resulting in an initial reaction pressure of 970 psig. This provided a mole ratio of 1.26:1 isobutylene to toluenediamine. The reaction mixture was maintained at 200° C. for about 45 hours with constant agitation.

Workup

  1. customwas carried out in a 1 gallon stainless steel pressure vessel
  2. customequipped with a mechanical stirrer
  3. additionThe vessel was charged with a 150 gram portion of a powdered commercially available silica-alumina catalyst
  4. customThe autoclave was sealed
  5. custompurged with nitrogen
  6. waitA residual blanket of nitrogen was left in the autoclave
  7. customleaving the pressure at 16 psig
  8. additionwere added over a 30 minute period
  9. customresulting in an initial
  10. customreaction pressure of 970 psig

Sources & evidence

ORD record
ord-d47c6402d018418bab5fb1354eb0a6db
Source dataset
uspto-grants-1988_04
Patent number
US04740620

Reaction notes

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