Acrylic Acid → Acrylic Acid Trimethylolpropane Triacrylate

HRID 83937

Reaction equation

HRID 83937 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].C(N(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].[Na+].[Na+].[C:38]([OH:42])(=[O:41])[CH:39]=[CH2:40].[C:43]([OH:47])(=[O:46])[CH:44]=[CH2:45].[C:48]([OH:52])(=[O:51])[CH:49]=[CH2:50].[CH2:53]([C:55]([CH2:60][OH:61])([CH2:58][OH:59])[CH2:56][CH3:57])[OH:54].[O-]S(OOS([O-])(=O)=O)(=O)=O.[Na+].[Na+]>O>[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[C:38]([OH:42])(=[O:41])[CH:39]=[CH2:40].[C:43]([OH:47])(=[O:46])[CH:44]=[CH2:45].[C:48]([OH:52])(=[O:51])[CH:49]=[CH2:50].[CH2:53]([C:55]([CH2:60][OH:61])([CH2:58][OH:59])[CH2:56][CH3:57])[OH:54]

Participants

6

Reactant 4

HCID 6581Acrylic Acid2×HCID 8779Pentasodium PentetateHCID 62655Sodium PersulfateHCID 250191762-Ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid

Product 1

HCID 19427618Acrylic Acid Trimethylolpropane Triacrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a three neck round bottom glass flask, equipped with a mechanical stirrer and a thermocouple with a nitrogen inlet at the side of the inlet-tube was added 70.38 g of 20% caustic (0.353 mol) and 15.63 g water. Next, 26 g of acrylic acid (0.36 mol) were added slowly via a dropping funnel. After the mixture was cooled to room temperature, 0.28 g of a 40 wt. % active solution of Versenex 80 (diethylene glycol triamine pentaacetate from Aldrich) were added. Then 0.8 g trimethylolpropane triacrylate (TMPTA) were dissolved in 13.75 g acrylic acid (0.19 mol) and added to the reaction flask. The dropping funnel was taken off and the opening was covered by a septum. An amount of 0.2 ml of a 0.1% solution of FeSO4x7H2O was added by a syringe through the septum, followed by 0.635 ml of a 10% Na2S2O8 solution. The reaction started immediately. A gel formed. After the temperature peaked the flask was heated for another hour at 70° C. using a heating mantle. Then the aqueous gel was removed and was minced in a lab grinder. One portion was heated in a vacuum oven for 2 hours at 170° C. and a second portion was heated for several hours at 220° C. The products were ground and sieved with 30 mesh (595 μm) and 50 mesh (297 μm) sieves.

Workup

  1. customTo a three neck round bottom glass flask, equipped with a mechanical stirrer
  2. additionadded to the reaction flask
  3. customA gel formed
  4. temperaturewas heated for another hour at 70° C.
  5. customThen the aqueous gel was removed
  6. temperatureOne portion was heated in a vacuum oven for 2 hours at 170° C.
  7. temperaturea second portion was heated for several hours at 220° C
  8. filtrationsieved with 30 mesh (595 μm) and 50 mesh (297 μm)

Sources & evidence

ORD record
ord-a8203ea07a78435ba41ac0091019f882
Source dataset
uspto-grants-2014_09
Patent number
US08846817B2

Linked notes

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