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

HRID 972554Notes

Reaction equation

HRID 972554 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(Cl)C=CC1C=CC=CC=1>O>[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[C:10]([OH:14])(=[O:13])[CH:11]=[CH2:12].[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 90154-MethoxyphenolHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a 10 l three-necked flask with a stirrer, a water separator and a gas inlet tube, 2.68 kg of trimethylolpropane, 3.03 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 from Bayer AG), 9 g of hydroquinone monomethyl ether and 28.6 g of cinnamyl chloride, together with 1.5 l of petroleum ether (boiling range 60°-70° C.) were heated under the water separator, whilst stirring. At the same time a continuous stream of air was passed through at a rate of about 2 l/hour. After a reaction period of 72 hours, an acid of 17 was reached. The petroleum ether was distilled off, residues being removed by applying a vacuum of about 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 flow time of 186 seconds, measured according to DIN 53,211 in a DIN cup 4, at 20° C.

Workup

  1. customAfter a reaction period of 72 hours
  2. distillationThe petroleum ether was distilled off
  3. customresidues being removed
  4. customat a product temperature of 40° C
  5. filtrationThe esterification catalyst was filtered off
  6. customcorresponded to a flow time of 186 seconds
  7. custommeasured according to DIN 53,211 in a DIN cup 4, at 20° C.

Sources & evidence

ORD record
ord-26b958f65bc045618aad00c3b43536c9
Source dataset
uspto-grants-1977_10
Patent number
US04053504

Reaction notes

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