Ethylbenzene → HCID 86657606, compound

HRID 1427193Notes

Reaction equation

HRID 1427193 reaction equation
C([Li])CCC.[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].C(C1C=CC=CC=1)C.[CH3:20][N:21]([CH3:27])[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25]>C1CCCCC1.O>[CH3:6][C:7]([CH3:10])([O-:9])[CH3:8].[K+:11].[CH3:20][N:21]([CH3:27])[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 7500EthylbenzeneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium2×

Product 1

HCID 86657606HCID 86657606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent4×

Procedure

The procedure of Example 10 was repeated except that: 1325 g (≈1.7 liters, 15.74 mole) of cyclohexane was charged to the reactor (12 ppm residual H2O), which was further made anhydrous by the addition of 0.30 g (4.7 mmole) n-butyllithium. The anhydrous cyclohexane was heated to 70° C., upon reaching the set point temperature, a mixture comprised of 9.14 g (0.081 mole) potassium t-butoxide, 80 g (0.95 mole) cyclohexane, 236.6 g (2.23 mole, 100 ppm water) ethylbenzene and 50.30 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.433 mole) was charged through the charge vessel and delivered subsurface to the gently agitated (300 rpm) cyclohexane solution. The vessel and line were flushed with a 100 ml aliquot of cyclohexane before charging with 31.47 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.081 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) 1563 g (18.57 mole) of cyclohexane was charged to the reactor prior to initiating the styrene feed. Styrene, 1648 g (15.82 mole) was fed through the 1/16th inch OD feed line over 366 minutes such that the feed velocity was ≈3.82 ft/s with a feed rate of 4.50 g/min. The reaction mixture was quenched with 9.76 g (0.163 mole) isopropyl alcohol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 1598, Mn: 1056, Mw: 2027, Mz: 3377, PD: 1.92, σn==1010, nα3=2.699.

Workup

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

Sources & evidence

ORD record
ord-af997966d9894541b5b0f38d345e4b51
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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