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

Participants

Reaction Steps

The procedure of Example 10 was repeated except that: 1097 g (≈=13 liters, 11.91 mole) of toluene was charged to the reactor (30 ppm residual H2O), which was further made anhydrous by the addition of 0.51 g (7.9 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 12.80 g (0.114 mole) potassium t-butoxide, 480 g (5.21 mole) toluene and 70.30 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.605 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 44.43 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.114 mole). The initial total toluene charge to the reactor is (the initial charge, the amount used to form the potassium t-butoxide/TMEDA solution and the amount used to flush the charge lines) 1747 g (16.8 mole) prior to initiating the styrene feed. Styrene, 3004 g (28.84 mole) was combined with 628 g (6.04 mole) of toluene and then fed through the 1/16th inch OD feed line over 170 minutes such that the feed velocity was ≈18 ft/s with a styrene feed rate of 17.67 g/min (solution feed rate of 21.4 g/min). The reaction mixture was quenched with 13.72 g (0.229 mole) acetic acid in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 404, Mn: 484, Mw: 714, Mz: 1004, PD: 1.47, σn=334, nα3=1.937. The workup procedure followed the general workup procedure as in Example 10—Part B, with the following conditions

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