Ethylbenzene → HCID 86657606, compound

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1325 g (≈1.7 liters, 15.74 mole) of cyclohexane was charged to the reactor (12 ppm residual H2O), which was further made anhydrous by the addition of 0.30 g (4.7 mmole) n-butyllithium. The anhydrous cyclohexane was heated to 70° C., upon reaching the set point temperature, a mixture comprised of 9.14 g (0.081 mole) potassium t-butoxide, 80 g (0.95 mole) cyclohexane, 236.6 g (2.23 mole, 100 ppm water) ethylbenzene and 50.30 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.433 mole) was charged through the charge vessel and delivered subsurface to the gently agitated (300 rpm) cyclohexane solution. The vessel and line were flushed with a 100 ml aliquot of cyclohexane before charging with 31.47 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.081 mole). All total (the initial charge, the amount used to form the potassium t-butoxide/TMEDA solution and the amount used to flush the charge lines) 1563 g (18.57 mole) of cyclohexane was charged to the reactor prior to initiating the styrene feed. Styrene, 1648 g (15.82 mole) was fed through the 1/16th inch OD feed line over 366 minutes such that the feed velocity was ≈3.82 ft/s with a feed rate of 4.50 g/min. The reaction mixture was quenched with 9.76 g (0.163 mole) isopropyl alcohol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 1598, Mn: 1056, Mw: 2027, Mz: 3377, PD: 1.92, σn==1010, nα3=2.699.

Provenance & Evidence