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

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1220 g (≈1.4 liters, 13.24 mole) of toluene was charged to the reactor (12 ppm residual H2O), which was further made anhydrous by the addition of 0.14 g (2.1 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 16.34 g (0.146 mole) potassium t-butoxide, 188 g (2.04 mole) toluene and 85.53 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.736 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 56.28 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.145 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) 1578 g (17.1 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3647 g (35.02 mole) was fed through the 1/16th inch OD feed line over 186 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 19.61 g/min. The reaction mixture was quenched with 17.45 g (0.291 mole) acetic acid in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 512, Mn: 539, Mw: 780, Mz: 1074, PD: 1.45, σn=360, nα3=1.813.

Provenance & Evidence