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

HRID 1427184Notes

Reaction equation

HRID 1427184 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: 1215 g (≈1.4 liters, 13.19 mole) of toluene was charged to the reactor (59 ppm residual H2O), which was further made anhydrous by the addition of 0.66 g (10.3 mmole) n-butyllithium. The anhydrous toluene was heated to 80° C., upon reaching the set point temperature, a mixture comprised of 16.29 g (0.145 mole) potassium t-butoxide, 186 g (2.02 mole) toluene and 90.45 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.778 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 56.00 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.144 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) 1571 g (17.1 mole) of toluene was charged to the reactor prior to initiating the styrene feed. Styrene, 3604 g (34.60 mole) was fed through the 1/16th inch OD feed line over 184 minutes such that the feed velocity was ≈17 ft/s with a feed rate of 19.59 g/min. The reaction mixture was quenched with 200 g (11.1 mole) of deoxygenated water pumped into the reactor. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 517, Mn: 547, Mw: 795, Mz: 1092, PD: 1.45, σn=368, nα3=1.773. 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-c9921a414ebf46b1a7c442f4c2600570
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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