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

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1250 g (≈4.4 liters, 13.57 mole) of toluene was charged to the reactor (25 ppm residual H2O), which was further made anhydrous by the addition of 0.28 g (4.4 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, 150 g (1.63 mole toluene) and 75.70 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.651 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 48.70 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.125 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) 1570 g (17.0 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3678 g (35.31 mole) was fed through the 1/16th inch OD feed line over 180 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 20.43 g/min. The reaction mixture was quenched with 15.03 g (0.250 mole) acetic acid in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 509, Mn: 514, Mw: 724, Mz: 1002, PD: 1.41, σn=329, nα3=1.992.

Provenance & Evidence