Dicyclopentadiene → Formaldehyde

HRID 2379478Notes

Reaction equation

HRID 2379478 reaction equation
C1C=CC(/C=C/[CH2:9][O:10][C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC=1.[CH2:22]1[CH:26]2[CH:27]3[CH:31]=[CH:30][CH:29]([CH:25]2[CH:24]=[CH:23]1)[CH2:28]3.[CH:32]1[CH2:36][CH:35]=[CH:34][CH:33]=1>O>[CH3:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:36][C:35]([OH:10])=[CH:34][CH:33]=1.[CH2:9]=[O:10]

Participants

6

Reactant 3

HCID 6492DicyclopentadieneHCID 7612CyclopentadieneHCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol

Product 2

HCID 712FormaldehydeYield 68%HCID 17524-Nonylphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

300 g of rosin are heated to 260° C. in a 3 liter pressure apparatus. 700 g of dicyclopentadiene containing 75% of cyclopentadiene units are metered in within 2 hours, and the mixture is kept at this temperature for a further 5 hours while stirring; during this procedure, the pressure, which initially increased to 9 bar, decreases to 5 bar. The melt is then allowed to cool to 160° C. 710 g of a water-soluble resol obtained from 1,860 g of nonylphenol and 510 g of formaldehyde (processing viscosity 250 mPa.s, residue on drying 68% after heating for one hour at 135° C.) are metered into this cooled melt. With constant removal of water, the mixture is heated to 250° C. and then, on reaching a viscosity of 100 mPa.s of a 50% strength toluene solution at 23° C., down to 50 mbar while distilling off the volatile components. Yield 1402 g, melting point 145° C., acid number 11 mg KOH/g, viscosity of a 40% strength solution in linseed oil at 350 dPa.s/23° C., compatibility with a mineral oil having a low aromatics content and a boiling range of 240°-270° C. and having an aniline point of 72° C. better than 1 : 20, and with an aromatics-free mineral oil having a boiling range of 240°-270° C. and an aniline point of 92° C. 1 : 2. The compatibility with linseed oil is infinite at 23° C. The weight average molecular weight Mw is 7,550.

Workup

  1. customare metered in within 2 hours
  2. temperatureduring this procedure, the pressure, which initially increased to 9 bar

Sources & evidence

ORD record
ord-4e576571d4aa42fcb29c061c41411194
Source dataset
uspto-grants-1994_11
Patent number
US05362818

Reaction notes

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