N,N,N',N'-Tetramethylethylenediamine → HCID 86657606, compound

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1188 g (≈1.4 liters, 12.90 mole) of toluene was charged to the reactor (19 ppm residual H2O), which was further made anhydrous by the addition of 0.21 g (3.2 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 14.01 g (0.125 mole) potassium t-butoxide, 167 g (1.81 mole) toluene and 74.73 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.643 mole) was charged through the charge vessel and delivered subsurface to the gently agitated (300 rpm) toluene solution. The vessel and line were flushed with a 100 ml aliquot of toluene before charging with 47.35 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.122 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) 1526 g (16.6 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3655 g (35.09 mole) was fed through the 1/16th inch OD feed line over 176 minutes such that the feed velocity was ≈18 ft/s with a feed rate of 20.77 g/min. The reaction mixture was quenched with 14.82 g (0.247 mole) isopropyl alcohol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 508, Mn: 497, Mw: 675, Mz: 895, PD: 1.36, σn=297, nα3=1.732. The workup procedure followed the general workup procedure as in Example 10—Part B, with the following conditions:

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