Ethylene → Ethylene Vinylethylene Carbonate

HRID 2288941Notes

Reaction equation

HRID 2288941 reaction equation
C=C.[C:3]1(=[O:10])[O:7][CH2:6][CH:5]([CH:8]=[CH2:9])[O:4]1>C(Cl)Cl>[CH2:5]=[CH2:6].[C:3]1(=[O:10])[O:7][CH2:6][CH:5]([CH:8]=[CH2:9])[O:4]1

Participants

4

Reactant 2

HCID 6325EthyleneHCID 27350381,3-Dioxolan-2-one, 4-ethenyl-

Product 1

HCID 86755542Ethylene Vinylethylene Carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 300 mL flame dried round bottom Schlenk flask was charged with α-diimine Pd(II) catalyst X (100 mg) in an argon filled glove box. Upon removal from the glove box, the flask was evacuated and backfilled with ethylene. The catalyst was dissolved in CH2Cl2 (50 mL) and immediately treated with vinylethylene carbonate (12 mL). The resulting orange solution was stirred at 23° C. under an ethylene atmosphere (1 atm) overnight. A small amount of polymer had precipitated out of solution. The polymerization was quenched with MeOH and filtered on a glass frit. The polymer was collected and dried in vacuo at 60° C. for 3 days to afford a tacky solid (800 mg). 1H NMR was consistent with a copolymer containing approximately 99.5 mole % ethylene and 0.5 mole % vinylethylene carbonate monomer units. IR (CH2Cl2 film) 1818 cm-1 ; Mn 40,000 g /mol ; Mw 81,000 g /mol ; DSC Tg -62° C., Tm -30° C.

Workup

  1. customDSC Tg -62° C., Tm -30° C.

Sources & evidence

ORD record
ord-c64face711a64fcaa8d5f564b5d8ab55
Source dataset
uspto-grants-2000_07
Patent number
US06090900

Reaction notes

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