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

HRID 1427191Notes

Reaction equation

HRID 1427191 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: 1281 g (≈1.5 liters, 13.90 mole) of toluene was charged to the reactor (33 ppm residual H2O), which was further made anhydrous by the addition of 0.38 g (5.9 mmole) n-butyllithium. The anhydrous toluene was heated to 70° C., upon reaching the set point temperature, a mixture comprised of 18.19 g (0.162 mole) potassium t-butoxide, 164 g (1.78 mole toluene) and 99.00 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.852 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 62.40 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.161 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) 1615 g (17.5 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3722 g (35.74 mole) was fed through the 1/16th inch OD feed line over 188 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 19.80 g/min. The reaction mixture was quenched with 19.39 g (0.323 mole) acetic acid in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 415, Mn: 576, Mw: 845, Mz: 1155, PD: 1.47, σn=394, nα3=1.694.

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-4ab656be792544ec89b275d23227a053
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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