Sulfuric Acid → 1-Methyl-2-(1-phenylethyl)benzene

HRID 231758Notes

Reaction equation

HRID 231758 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>O>[C:15]1([CH:14]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:7])[CH3:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 1140TolueneHCID 7501Styrene2×HCID 14798Sodium Hydroxide2×

Product 1

HCID 2185401-Methyl-2-(1-phenylethyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene 4423g was charged to a 12 liter bottom outlet Pyrex reactor equipped with a mechanical agitator, heating mantle, addition funnel, cooling coil, thermometer, and a reflux condenser. Sulfuric acid, 981g of 96% was charged in one portion with agitation. Styrene, 3749g, was added dropwise at 80°-85° over 90 min. The mixture was agitated for an additional 30 min. At 80°-85° C. after the styrene addition was complete, the mixture was allowed to settle for 45 min. and the lower sulfuric acid layer was drained off. A solution of sodium hyroxide (80g in 552g of water) was charged and the mixture was allowed to settle for 30 min, and the lower sodium hydroxide layer was drained off at 80° C. Hot water (1440g) was charged and the mixture was agitated for 15 min. then allowed to settle for 30 in. The water wash was separated leaving 7375g of crude phenyltolylethane alkylate. The phenyltolylethane alkylate was vacuum fractionated to remove excess toluene then pure phenyltolylethane, BP 205° C. 100 mmHg.

Workup

  1. customequipped with a mechanical agitator
  2. temperatureheating
  3. additionmantle, addition funnel
  4. temperaturecooling coil
  5. waitto settle for 45 min.
  6. waitto settle for 30 min
  7. customwas drained off at 80° C
  8. stirringthe mixture was agitated for 15 min.
  9. washThe water wash
  10. customwas separated

Sources & evidence

ORD record
ord-1aae02c49cee4c50b2614036b343867d
Source dataset
uspto-grants-1989_07
Patent number
US04849400

Reaction notes

Loading…