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

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1215 g (≈1.4 liters, 13.19 mole) of toluene was charged to the reactor (59 ppm residual H2O), which was further made anhydrous by the addition of 0.66 g (10.3 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 16.29 g (0.145 mole) potassium t-butoxide, 186 g (2.02 mole) toluene and 90.45 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.778 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 56.00 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.144 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) 1571 g (17.1 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3604 g (34.60 mole) was fed through the 1/16th inch OD feed line over 184 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 19.59 g/min. The reaction mixture was quenched with 200 g (11.1 mole) of deoxygenated water pumped into the reactor. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 517, Mn: 547, Mw: 795, Mz: 1092, PD: 1.45, σn=368, nα3=1.773. The workup procedure followed the general workup procedure as in Example 10—Part B, with the following conditions

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