Ethylbenzene → HCID 86657606, compound

HRID 1427194Notes

Reaction equation

HRID 1427194 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: 1290 g (≈1.7 liters, 15.33 mole) of cyclohexane was charged to the reactor (18 ppm residual H2O), which was further made anhydrous by the addition of 0.35 g (5.5 mmole) n-butyllithium. The anhydrous cyclohexane was heated to 70° C., upon reaching the set point temperature, a mixture comprised of 10.36 g (0.092 mole) potassium t-butoxide, 82 g (0.98 mole) cyclohexane, 238.6 g (2.25 mole, 131 ppm water) ethylbenzene and 57.42 g of N,N,N′,N′-tetramethylethylenediamine (TMEDA, 0.494 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 36.36 g n-butyllithium solution (2.0 M, 16.5 wt % in cyclohexane, 0.094 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) 1526 g (18.13 mole) of cyclohexane was charged to the reactor prior to initiating the styrene feed. Styrene, 1675 g (16.08 mole) was fed through the 1/16th inch OD feed line over 375 minutes such that the feed velocity was ≈3.79 ft/s with a feed rate of 4.47 g/min. The reaction mixture was quenched with 11.17 g (0.186 mole) isopropyl alcohol in 100 ml of toluene. An aliquot of the reaction mixture gave the following GPC analysis: Mp: 1585, Mn: 1046, Mw: 2055, Mz: 3471, PD: 1.96, σn=1030, nα3=2.771.

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-a746d0f724544d828517ea89f349a2bb
Source dataset
uspto-grants-2015_01
Patent number
US08933159B2

Reaction notes

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