Hydrochloric Acid → 4-tert-Butyl-6-methylbenzene-1,3-diamine
Reaction equation
[C:1]1([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]([NH2:7])=[CH:5][CH:6]=1.Cl.[CH3:11][C:12](=[CH2:14])[CH3:13]>>[C:12]([C:5]1[CH:6]=[C:1]([CH3:9])[C:2]([NH2:8])=[CH:3][C:4]=1[NH2:7])([CH3:13])([CH3:11])[CH3:14]Participants
Conditions
- Temperature
- 180 °C
Procedure
A 300 cc Hastalloy C pressure vessel equipped with a mechanical stirrer was used for producing t-butyltoluenediamine. Approximately 100 grams or 0.819 moles of 2,4-toluenediamine were charged to the vessel along with 5 grams of 36% aqueous hydrochloric acid. The vessel was sealed and purged with nitrogen, leaving a 33 psig nitrogen blanket. The vessel contents then were heated to 180° C. with continuous stirring. Isobutylene then was introduced into the reactor and 53.4 grams or 0.06 moles were added over 15 minutes. On addition of the isobutylene, the pressure in the reactor increased to 766 psig. The reaction mixture was maintained at 180° C. for 24 hours with constant stirring. At the end of the 24 hour period the pressure had dropped to 524 psig. The contents were then cooled to 160° C. and stirring discontinued. At that time the reactor was vented and the reaction product analyzed for composition.
Workup
- customThe vessel was sealed
- custompurged with nitrogen
- customleaving a 33 psig nitrogen blanket
- additionwere added over 15 minutes
- temperaturethe pressure in the reactor increased to 766 psig
- temperatureThe reaction mixture was maintained at 180° C. for 24 hours with constant stirring
- additionAt the end of the 24 hour period the pressure had dropped to 524 psig
- temperatureThe contents were then cooled to 160° C.
Sources & evidence
- ORD record
- ord-2185e49cdbc746ec93aeee78da99d909
- Source dataset
- uspto-grants-1988_05
- Patent number
- US04745223
Reaction notes
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