2,4,4-Trimethyl-1-pentene → N-octyl-N-phenylaniline
Reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C:15]([CH2:17][C:18]([CH3:21])(C)C)=[CH2:16].[CH3:22][C:23](=C)[CH3:24]>>[CH2:22]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:23][CH2:24][CH2:21][CH2:18][CH2:17][CH2:15][CH3:16]Participants
Conditions
- Temperature
- 160 °C
Procedure
In a 50 gallon (about 189 L) reactor, 144 pounds (about 65.5 kg) of diphenylamine and 5.9 pounds (about 2.7 kg) of Filtrol™ clay (Engelhard Corp., Iselin, N.J.) were mixed in a reactor and heated to 160° C. for 20 minutes to drive off moisture. About 124.3 pounds (about 56.5 kg) of diisobutylene at room temperature was then added to the reactor at a rate of about 60 pounds (about 27 kg) per minute. The reaction temperature dropped to 140° C. and then climbed back to an initial set point temperature of 160° C. Within about 10 minutes of first adding the diisobutylene, 37.4 pounds (about 17 kg) of isobutylene was charged in the reactor over one hour. The temperature during this period reached a maximum of about 190° C. due to the exothermic nature of the reaction. Based on experience and Examples illustrated in U.S. Pat. No. 5,750,787, it is believed that the initiation of the addition of isobutylene occurred before the reactive composition of diisobutylene and diphenylamine formed at least 50 wt. % monooctyldiphenylamine.
Workup
- additionThe reaction temperature dropped to 140° C.
- customset point temperature of 160° C
- additionwas charged in the reactor over one hour
- waitThe temperature during this period reached
- customa maximum of about 190° C. due to the exothermic nature of the reaction
Sources & evidence
- ORD record
- ord-7ddc7457265546cf901158002619f0ca
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204412B1
Reaction notes
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