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

HRID 1427183Notes

Reaction equation

HRID 1427183 reaction equation
C([Li])CCC.[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].[CH3:12][N:13]([CH3:19])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17]>C1(C)C=CC=CC=1.O>[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].[CH3:12][N:13]([CH3:19])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium2×

Product 1

HCID 86657606HCID 86657606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent4×

Procedure

The procedure of Example 10 was repeated except that: 1088 g (≈1.3 liters, 11.81 mole) of toluene was charged to the reactor (41 ppm residual H2O), which was further made anhydrous by the addition of 0.48 g (7.6 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 13.06 g (0.116 mole) potassium t-butoxide, 399 g (4.33 mole) toluene and 72.00 g N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.620 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 46.17 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.119 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) 1657 g (18.0 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3718 g (35.70 mole) was fed through the 1/16th inch OD feed line over 182 minutes such that the feed velocity was ≈18 ft/s with a feed rate of 20.43 g/min. The reaction mixture was quenched with 7.52 g (0.235 mole) methanol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 413, Mn: 620, Mw: 885, Mz: 1233, PD: 1.42, σn405, nα=1.991. The workup procedure followed the general workup procedure as in Example 10—Part B, with the following conditions:

Workup

  1. additionwas charged through the charge vessel
  2. customThe vessel and line were flushed with a 100 ml aliquot of toluene
  3. additionAll total (the initial charge

Sources & evidence

ORD record
ord-202ee150db2a402092049d4f5cd8a8a6
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

Loading…