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

HRID 1427188Notes

Reaction equation

HRID 1427188 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 1140TolueneSolvent5×

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-1f5ccac8d9ae40ddb38930d23f5dc6c4
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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