Hydrogen Peroxide → Dicyclopentadiene

HRID 2073379Notes

Reaction equation

HRID 2073379 reaction equation
OO.[C:3]1([CH3:13])[CH:8]=[CH:7][C:6](S(O)(=O)=O)=[CH:5][CH:4]=1.[C:14](OC)(=O)[C:15](C)=C.[CH3:21]OC1C=CC(O)=CC=1>>[CH2:14]1[CH:4]2[CH:5]3[CH:6]=[CH:7][CH:8]([CH:3]2[CH:13]=[CH:15]1)[CH2:21]3

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 6101p-Toluenesulfonic acidHCID 6658Methyl MethacrylateHCID 90154-Methoxyphenol

Product 1

HCID 6492Dicyclopentadiene

Conditions

Temperature
60 °C

Procedure

Into the same apparatus as in Example 9 were charged 194 g (1 mole) of ethylene glycol monodicyclopentenyl ether ##STR16## peroxide content: 35 ppm in terms of H2O2), and 5 g of p-toluenesulfonic acid. The temperature was raised to 60° C. with stirring and kept there for 10 minutes. Then, 350 g of methyl methacrylate and 0.13 g of 4-methoxyphenol were charged into the apparatus, and thereafter the reaction was carried out in the same manner as in Example 1. One hour after the beginning of raction, the reaction solution was colored dark-brown so seriously that when it was placed in a 18 mm diameter test tube, a substance on one side of the test tube could not be seen through the test tube from the other side. At that time the conversion was 25%. In addition, oligomer by-products having a molecular weight of about 700 to 1000 (which were presumed to be oligomers formed by ionic polymerization of dicyclopentadiene) had been formed in an amount of about 2%.

Workup

  1. customOne hour
  2. customwas placed in a 18 mm diameter test tube

Sources & evidence

ORD record
ord-4415fcab8a9543778d25d8394d59feb5
Source dataset
uspto-grants-1990_04
Patent number
US04916255

Reaction notes

Loading…