Dicyclopentadiene → HCID 66588561, compound

Participants

Reaction Conditions

Reaction Steps

A multi-neck 1 liter flask to be fitted with condenser, overhead stirrer and thermometer was charged with: 414 g of phenol (4.4 moles which contained 0.04% water); 2.08 g of 10% triflic acid in phenol; and 0.2g of N-methyl pyrrolidone. This reaction mixture was heated to 45° C. at which time 262 g of dicyclopentadiene (1.98 moles of Ultrene 97) was added over 2 hours while maintaining 45° C.±0.5° C. The reaction was maintained at 45° C. for an additional 4 hours whereupon catalyst was neutralized by addition of 0.50 g of 10% sodium hydroxide in water. The reaction was heated under vacuum to recover the majority of unreacted phenol at 125-130° C. under 26.5 to 29.5 inches vacuum. Further recovery was obtained by heating at 160° C. under 29.5 inches vacuum. Phenol level was further reduced by introduction of water at 155-160° C. under 20 inches of vacuum and then heating continued briefly at 160° C. under 29.5 inches vacuum. Yield of phenol vacuum distillate was 317 g and yield of condensate was 330 g which was characterized as follows; 0.05% free phenol, Mw/Mn=140/138(112/106 with the SEC peak at 95±1); 0.54% of dicyclopentadiene; viscosity of 270 cps (25° C.) and there was extensive crystallization of the condensate upon standing. The high level of dicyclopentadiene is atypical since levels ore generally below 0.1% which is indicative of quantitative conversion.

Provenance & Evidence