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

HRID 1427186Notes

Reaction equation

HRID 1427186 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: 1268 g (≈1.5 liters, 13.76 mole) of toluene was charged to the reactor (56 ppm residual H2O), which was further made anhydrous by the addition of 0.64 g (10.0 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 14.07 g (0.125 mole) potassium t-butoxide, 160 g (1.74 mole) toluene and 78.77 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.678 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 47.74 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.123 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) 1598 g (17.3 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3620 g (34.76 mole) was fed through the 1/16th inch OD feed line over 180 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 20.11 g/min. The reaction mixture was quenched with 14.91 g (0.248 mole) acetic acid in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 520, Mn: 551, Mw: 747, Mz: 986, PD: 1.36, σn=329, nα3=1.692. 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-cdf7f4210cd84dc4b681e75f6b67d362
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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