Isoprene → 4-Methyl-6-(3-methylbut-2-en-1-yl)benzene-1,3-diamine

HRID 231364Notes

Reaction equation

HRID 231364 reaction equation
[C:1]1([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]([NH2:7])=[CH:5][CH:6]=1.[CH2:10]=[CH:11][C:12](=[CH2:14])[CH3:13]>CCCCC>[CH3:14][C:12]([CH3:13])=[CH:11][CH2:10][C:5]1[CH:6]=[C:1]([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]=1[NH2:7]

Participants

4

Reactant 2

HCID 6557IsopreneHCID 72612,4-Diaminotoluene

Product 1

HCID 156640144-Methyl-6-(3-methylbut-2-en-1-yl)benzene-1,3-diamine

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

A 200g (1.64 mol) portion of 2,4-toluenediamine, 167g (2.45 mol) of isoprene, 200g (2.78 mol) pentane, and 20g of catalyst comprised of 13% alumina and 87% silica were reacted at 200° C. in a similar fashion as indicated in Example 5. Isolation of catalyst free sample was accomplished by hot filtration. Selective removal of all residual low boiling hydrocarbons by vacuum distillation afforded the following product mixture:

Workup

  1. customwere reacted at 200° C. in a similar fashion as indicated in Example 5
  2. filtrationIsolation of catalyst free sample was accomplished by hot filtration
  3. customremoval of all residual
  4. distillationby vacuum distillation
  5. customafforded the following product mixture

Sources & evidence

ORD record
ord-673ba9a5030b46539174c063369fe477
Source dataset
uspto-grants-1989_07
Patent number
US04845291

Reaction notes

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