Ethylene → Ethylene vinyl Ethylene Carbonate

Temperature

23 °C

A 200 mL flame dried pear-shaped Schlenk flask equipped with a magnetic stir bar and capped with a septum was charged with (2,6-di-isopropylphenylimino)-[1.4]dithiane Pd(II) catalyst XXXV (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 (25 mL) and immediately treated with vinyl ethylene carbonate (5 mL). The resulting orange solution was stirred at 23° C. under an ethylene atmosphere (1 atm) for 20 hours. A small amount of polymer had precipitated out of solution. The polymerization was quenched with MeOH and acetone leaving gray oil adhering to the walls of the flask. The polymer was washed several times with acetone and MeOH to remove any remaining monomer. The polymer was dissloved in CH2Cl2 and transferred to a storage jar. The solvent was left to evaporate and the resulting oily polymer was dried in vacuo at ˜80° C. for 3 days to afford a tacky solid (2.15 g, 1100 TO). 1H NMR was consistent with a copolymer containing approximately 96.5 weight % ethylene and 3.5 weight % vinyl ethylene carbonate monomer units.; Mn 40,200 g/mol; Mw 92,100 g/mol; DSC Tg−68° C. Tm−38° C.

1. temperatureA 200 mL flame dried pear-shaped Schlenk flask
2. customequipped with a magnetic stir bar
3. customcapped with a septum
4. customUpon removal from the glove box
5. customthe flask was evacuated
6. dissolutionThe catalyst was dissolved in CH2Cl2 (25 mL)
7. additionimmediately treated with vinyl ethylene carbonate (5 mL)
8. customA small amount of polymer had precipitated out of solution
9. customThe polymerization was quenched with MeOH and acetone leaving gray oil adhering to the walls of the flask
10. washThe polymer was washed several times with acetone and MeOH
11. customto remove any remaining monomer
12. waitThe solvent was left
13. customto evaporate
14. customthe resulting oily polymer was dried in vacuo at ˜80° C. for 3 days
15. customto afford a tacky solid (2.15 g, 1100 TO)
16. customTm−38° C.

ORD record

ord-53259c430fca4302ab598228d9b15438

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303720B1