2,4,4-Trimethyl-1-pentene → N-octyl-N-phenylaniline

HRID 1532801Notes

Reaction equation

HRID 1532801 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

4

Reactant 3

HCID 78682,4,4-Trimethyl-1-pentene3×HCID 8255Isobutylene2×HCID 11487Diphenylamine2×

Product 1

HCID 66575N-octyl-N-phenylaniline

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 over the period of one minute or less. The reaction temperature dropped and then climbed back to an initial set point temperature of 160° C. Within about 10 minutes of first adding the diisobutylene, 28.7 pounds (about 13 kg) of isobutylene was charged in the reactor over a period of about 30 minutes such that the pressure was kept below about 90 psi (about 6.2×105 Pa). 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

  1. additionThe reaction temperature dropped
  2. customset point temperature of 160° C
  3. additionwas charged in the reactor over a period of about 30 minutes such that the pressure

Sources & evidence

ORD record
ord-63fcf16503dc4c21888c3fe81c318600
Source dataset
uspto-grants-2001_03
Patent number
US06204412B1

Reaction notes

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