Dicyclopentadiene → HCID 66588561, compound

HRID 1596854Notes

Reaction equation

HRID 1596854 reaction equation
OS(C(F)(F)F)(=O)=O.CN1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].[CH2:16]1[CH:20]2[CH:21]3[CH:25]=[CH:24][CH:23]([CH:19]2[CH:18]=[CH:17]1)[CH2:22]3.[OH-].[Na+]>C1(O)C=CC=CC=1.O>[CH2:16]1[CH:20]2[CH:21]3[CH:25]=[CH:24][CH:23]([CH:19]2[CH:18]=[CH:17]1)[CH2:22]3.[C:11]1([OH:15])[CH:17]=[CH:16][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6492Dicyclopentadiene2×HCID 13387N-methyl-2-pyrrolidoneHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 66588561HCID 66588561, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 996PhenolSolvent5×

Conditions

Temperature
45 °C

Procedure

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.

Workup

  1. customA multi-neck 1 liter flask to be fitted with condenser
  2. additionwas added over 2 hours
  3. temperaturewhile maintaining 45° C.±0.5° C
  4. temperatureThe reaction was heated under vacuum
  5. customto recover the majority of unreacted phenol at 125-130° C. under 26.5 to 29.5 inches vacuum
  6. customFurther recovery was obtained
  7. temperatureby heating at 160° C. under 29.5 inches vacuum
  8. temperatureheating continued briefly at 160° C. under 29.5 inches vacuum
  9. customcrystallization of the condensate

Sources & evidence

ORD record
ord-e34fd1005c8e45df87854ffa846feae1
Source dataset
uspto-grants-2001_09
Patent number
US06291723B1

Reaction notes

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