Trimethylolpropane → 2-Ethyl-2-(hydroxymethyl)propane-1,3-diol;bis(prop-2-enoic acid)

HRID 1439474

Reaction equation

HRID 1439474 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].COC1C=CC(O)=CC=1.C(OCC=C)(=O)[C:25]1[C:26](=CC=CC=1)[C:27]([O:29]CC=C)=[O:28]>O>[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[C:27]([OH:29])(=[O:28])[CH:26]=[CH2:25].[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

6

Reactant 4

HCID 6510TrimethylolpropaneHCID 6581Acrylic AcidHCID 8560Diallyl phthalateHCID 90154-Methoxyphenol

Product 1

HCID 867352212-Ethyl-2-(hydroxymethyl)propane-1,3-diol;bis(prop-2-enoic acid)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.68 kg of trimethylolpropane, 3.03 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 of BAYER AG), 9 g of hydroquinone monomethyl ether and 1.5 liters of petroleum ether (boiling range 60° to 70° C) were heated under a water separator, whilst stirring, in a 10 liter three-necked flask equipped with a stirrer, water separator and gas inlet tube. At the same time, a constant stream of air was passed through the flask at about 2 liters/hour. Over the course of the entire reaction time of 72 hours, during which an acid number of 17 was reached, a total of 20 ml of diallyl phthalate was added dropwise to the reaction mixture. The petroleum ether was distilled off, remnants being removed by applying a vacuum of approx. 4 mm Hg at a product temperature of 40° C. The esterification catalyst was filtered off. The resulting trimethylolpropane diacrylate mixture was pale yellowish and clear. The viscosity corresponded to a time of outflow of 186 seconds, measured in a DIN cup 4, at 20° C.

Workup

  1. customequipped with a stirrer
  2. customOver the course of the entire reaction time of 72 hours
  3. distillationThe petroleum ether was distilled off
  4. customremnants being removed
  5. customat a product temperature of 40° C
  6. filtrationThe esterification catalyst was filtered off
  7. customcorresponded to a time of outflow of 186 seconds
  8. custommeasured in a DIN cup 4, at 20° C.

Sources & evidence

ORD record
ord-030ea17e9ed94786abf315118bdf74ae
Source dataset
uspto-grants-1977_11
Patent number
US04059721

Linked notes

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