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
- 140 °C
Procedure
3080 pounds (about 1400 kg) of diphenylamine (Aristech Chemical Corp., Pittsburgh, Pa.) and 125 pounds (about 56.8 kg) of Retrol™ F-20 clay (Engelhard Corp., Iselin, N.J.) were mixed in a reactor and heated to 140° C. for 10 minutes to drive off moisture. These components were then heated to 150° C. About 2658 pounds (443 gallons, about 1208 kg, about 1677 L) of diisobutylene (Neochem, Bayonne, N.J.) at room temperature was then added to the reactor at a rate of 50 gallons (about 189 L) per minute. The reaction temperature dropped and then climbed back to an initial set point temperature of 150° C. Within about 10 minutes of first adding the diisobutylene, 630 pounds (about 286 kg) of isobutylene (Exxon Chemical Co., Baytown, Tex.) was charged in the reactor at a rate of 18 pounds (about 8.2 kg) per minute. 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
- temperatureThese components were then heated to 150° C
- additionThe reaction temperature dropped
- customset point temperature of 150° C
- additionwas charged in the reactor at a rate of 18 pounds (about 8.2 kg) per minute
Sources & evidence
- ORD record
- ord-85ad0da106774a7a952faa9b63112123
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06204412B1
Reaction notes
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