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

HRID 972553Notes

Reaction equation

HRID 972553 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].C1(C=CC(O)=CC=1)O.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].[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 785HydroquinoneHCID 6510TrimethylolpropaneHCID 6581Acrylic AcidHCID 7501Styrene

Product 1

HCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;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, 2.44 kg of trimethylolpropane, 3.93 kg of acrylic acid, 0.5 kg of an acid ion exchanger (Lewatit 3333 from Bayer AG), 9 g of hydroquinone and also 19 g of styrene together with 1.5 l of petroleum ether (boiling range 60°-70° C.) were heated, whilst stirring, under the water separator. During the esterification a slow stream of air was passed through the reaction. After 80 hours, the reaction mixture had an acid number of 32 and the boiling point had risen to 72° C. The petroleum ether was distilled off, residues being removed by applying a vacuum of 0.2 mm Hg at a product temperature of 40° C. The esterification catalyst was separated off by filtration. The trimethylolpropane tris-acrylate, which was obtained in almost quantitative yield, was pale yellowish and clear. The viscosity corresponded to a flow time of 20 seconds, measured according to DIN 53,211 in a DIN cup 4, at 20° C. Even when stored for 4 months at 60° C., the product showed no change. When used in a printing ink, which can be cured by UV light, and which contained a photoinitiator, the product polymerised at a high rate.

Workup

  1. customDuring the esterification a slow stream of air was passed through the reaction
  2. customhad risen to 72° C
  3. distillationThe petroleum ether was distilled off
  4. customresidues being removed
  5. customat a product temperature of 40° C
  6. customThe esterification catalyst was separated off by filtration

Sources & evidence

ORD record
ord-628a605eb26f40e09abadc9cf14c63e5
Source dataset
uspto-grants-1977_10
Patent number
US04053504

Reaction notes

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