P-Cresol → HCID 54398422, compound

HRID 601089Notes

Reaction equation

HRID 601089 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.FC(F)(F)S(O)(=O)=O.[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH:17]([C:5]1[C:6]([OH:7])=[C:1]([CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:2]=[C:3]([CH3:8])[CH:4]=1)=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 2879P-Cresol3×HCID 7501Styrene3×HCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 54398422HCID 54398422, compound

Conditions

Temperature
70 °C

Procedure

This example illustrates a reaction system comprising two reactors and providing for a two tiered temperature profile for forming styrenated p-cresol. 50 Kg (110.2 lb, 462.2 moles) p-cresol was pumped from a preheated drum into a 50 gallon glass lined steel jacketed reactor equipped with an agitator, thermowell, and a pump around loop for sampling and acid injection. The p-cresol was heated to about 60° C. followed by the addition of 1.6 to 8.3 g (5.53e-05 to 1.07e-02 moles) of trifluoromethane sulfonic acid via a syringe in an injection port of the pump around loop. 93.9 Kg (2071b, 901.6 moles) styrene was fed through a mass flow meter at a constant rate over a 3 to 4 hour reaction time where the reactor temperature was maintained at 70° C. The molar ratio of styrene to p-cresol fed was maintained at 1.95. After the completion of the styrene feed, the reactor contents were pumped to a second 50 gallon glass lined steel jacketed reactor and heated to 90° C. Approximately 1.5 lb (0.7 Kg) of acid-leached bentonite clay (Filtrol 20×) was added through a man hole to the second reactor and agitated for 15 minutes. The product was then pumped to a bag filter and into product drums. The typical sample result from this production, based on total GC area, are provided below in TABLE 10.

Workup

  1. customequipped with an agitator
  2. aliquotthermowell, and a pump around loop for sampling
  3. customreaction time where the reactor temperature
  4. temperatureheated to 90° C
  5. additionApproximately 1.5 lb (0.7 Kg) of acid-leached bentonite clay (Filtrol 20×) was added through a man hole to the second reactor
  6. filtrationfilter and into product drums
  7. customThe typical sample result from this production
  8. customare provided below in TABLE 10

Sources & evidence

ORD record
ord-c89493007455457684e1f256b613dd3e
Source dataset
uspto-grants-2011_03
Patent number
US07902280B2

Reaction notes

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