Ethylene Glycol → 2-ethenylcyclopropane-1,1-dicarboxylic acid

HRID 2059092Notes

Reaction equation

C(O)CO.[CH:5]([CH:7]1[CH2:9][C:8]1([C:14]([O:16]C)=[O:15])[C:10]([O:12]C)=[O:11])=[CH2:6].C([O-])(=O)C.C([O-])(=O)C.C([Sn+2]CCCC)CCC.C1(C=CC(O)=CC=1)O>CO>[CH:5]([CH:7]1[CH2:9][C:8]1([C:14]([OH:16])=[O:15])[C:10]([OH:12])=[O:11])=[CH2:6]

Participants

Conditions

Temperature: 185 °C

Procedure

Ethylene glycol (0.2 mols) and dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (0.2 mols) were combined with 0.1 gms dibutyltin diacetate and 0.1 gms hydroquinone. The temperature was gradually raised to 185° C. over a 3 hour period and then maintained for an additional 41/2 hours during which time about 3.2 gms methanol was collected. The temperature was then reduced to about 80° C. and a vacuum (0.1 mm Hg) pulled on the system to remove final traces of volatile products. The resulting light viscous oil (38.5 gms) contained some monomeric product but consisted primarily of oligomeric products of up to about 5 repeating units. A portion of the product containing 5% benzoin isobutyl ether was spread on a glass plate and upon irradiation with an ultraviolet light source provided a transparent, tack-free, resilient polymer film. Similar products are obtained when 2-vinylcyclopropane-1,1-dicarboxylic acid is esterified with ethylene glycol and diethylene glycol.

Workup

customwas collected
customwas then reduced to about 80° C.
customto remove final traces of volatile products
additionA portion of the product containing 5% benzoin isobutyl ether
customwas spread on a glass plate and upon irradiation with an ultraviolet light source
customprovided a transparent, tack-free, resilient polymer film

Sources & evidence

ORD record: ord-0218e552e2b84d568ca1e228aa3195e3
Source dataset: uspto-grants-1982_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04321406

Reaction notes

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