Cyclopentadiene → HCID 19706219, compound

HRID 1680979Notes

Reaction equation

HRID 1680979 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:6]([OH:10])(=[O:9])[CH:7]=[CH2:8].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].[CH2:16]([C:18]([CH2:23][OH:24])([CH2:21][OH:22])[CH2:19][CH3:20])[OH:17].[CH:25]1[CH2:29][CH:28]=[CH:27][CH:26]=1>>[CH:18]12[CH2:21][CH:3]([CH:2]([C:1]([OH:5])=[O:4])[CH2:16]1)[CH:20]=[CH:19]2.[CH:26]12[CH2:25][CH:29]([CH:7]([C:6]([OH:10])=[O:9])[CH2:8]1)[CH:28]=[CH:27]2.[CH:18]12[CH2:21][CH:13]([CH:12]([C:11]([OH:15])=[O:14])[CH2:16]1)[CH:20]=[CH:19]2.[CH2:16]([C:18]([CH2:23][OH:24])([CH2:21][OH:22])[CH2:19][CH3:20])[OH:17]

Participants

3

Reactant 2

HCID 7612CyclopentadieneHCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Product 1

HCID 19706219HCID 19706219, compound

Conditions

Temperature
40 °C

Procedure

Trimethylolpropane triacrylate (338 g, 1.0 mol) was stirred under nitrogen in a 1000 ml, four-necked, round-bottomed flask equipped with a Freidrichs condenser, a thermometer, a constant pressure addition funnel, and mechanical stirring at 40° C. Freshly cracked cyclopentadiene monomer (217 g, 3.3 mol) was added at such a rate that the temperature of the reaction slowly climbs to about 90° C. by the end of the addition. The reaction mixture was stirred at this temperature for two hours. The extent of reaction as monitored by the decrease in the infrared absorption band at 1636 cm-1. When the reaction was judged to be complete (no change in the infrared absorption), excess cyclopentadiene was removed by vacuum concentration of the resin. The yield of resin is 534 g.

Workup

  1. customfour-necked, round-bottomed flask equipped with a Freidrichs condenser
  2. additiona thermometer, a constant pressure addition funnel
  3. customthat the temperature of the reaction
  4. additionslowly climbs to about 90° C. by the end of the addition
  5. stirringThe reaction mixture was stirred at this temperature for two hours
  6. customThe extent of reaction
  7. customin the infrared absorption), excess cyclopentadiene
  8. customwas removed by vacuum concentration of the resin

Sources & evidence

ORD record
ord-adba8a73a20b4fb596dc2e6ca51cebc6
Source dataset
uspto-grants-1992_12
Patent number
US05167882

Reaction notes

Loading…