Benzoic Acid → Dicyclopentadiene

HRID 2419164Notes

Reaction equation

HRID 2419164 reaction equation
[C:1](O)(=[O:8])[C:2]1C=CC=CC=1.[C:10]1(=[O:20])[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.OCC(CO)(CO)CO>C1(C)C(C)=CC=CC=1>[CH2:1]1[CH:19]2[CH:18]3[CH:17]=[CH:16][CH:12]([CH:11]2[CH:10]=[CH:2]1)[CH2:13]3.[C:13]([OH:14])(=[O:8])/[CH:12]=[CH:11]/[C:10]([OH:15])=[O:20]

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 6811Phthalic AnhydrideHCID 8285Pentaerythritol

Product 2

HCID 6492DicyclopentadieneHCID 444972Fumaric Acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

640 T of soya oil fatty acid, 180 T of benzoic acid, 350 T of phthalic anhydride and 335 T of pentaerythritol are condensed at 210° to 230° C, after the addition of 35 T of xylene, in an inert gas atmosphere with distillation of the water formed during esterification, until an acid number of less than 10 is reached. Then 155 T of a copolymer obtained from dicyclopentadiene and fumaric acid in a molar ratio of 5:1 and having an acid number of 30 and a softening temperature of 70 to 80° C are added and condensed at 240° C with the alkyd resin formed beforehand until a viscosity of 10000 mPa.s (55% in a benzinexylene mixture 4:1) and an acid number of less than 15, based on the solid resin, are obtained. The end product is diluted with the above-mentioned mixture of solvents to form a 55% solution.

Workup

  1. customcondensed at 210° to 230° C
  2. distillationin an inert gas atmosphere with distillation of the water
  3. customformed during esterification, until an acid number of less than 10

Sources & evidence

ORD record
ord-5c77756ee05e40dfa4a708971c7a328b
Source dataset
uspto-grants-1978_08
Patent number
US04105607

Reaction notes

Loading…