Acrylic Acid → Hydrogen Peroxide

HRID 1608638Notes

Reaction equation

HRID 1608638 reaction equation
C(O)(=O)/C=C\C(O)=O.C1(=O)OC(=O)[C@H]2CC=CC[C@@H]12.[OH-].[Na+:21].C(O)(=O)C=C.[S:27]([O:31][O:32][S:33]([O-:36])(=[O:35])=[O:34])([O-:30])(=[O:29])=[O:28].[Na+].[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[S:27]([O:31][O:32][S:33]([O-:36])(=[O:35])=[O:34])([O-:30])(=[O:29])=[O:28].[Na+:21].[Na+:21].[OH:31][OH:32]

Participants

10

Reactant 6

HCID 6581Acrylic Acid2×HCID 14798Sodium Hydroxide2×HCID 62655Sodium PersulfateHCID 98495Tetrahydrophthalic anhydride, cis-HCID 444266Maleic AcidHCID 656671Sodium Pyrosulfite

Product 2

HCID 784Hydrogen PeroxideHCID 62655Sodium Persulfate

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent5×

Conditions

Temperature
91 °C

Procedure

To a one liter, 4-neck flask equipped with a mechanical stirrer, reflux condenser, thermometer, and inlets for the gradual addition of monomer and initiator solution was added 50.0 grams of deionized water, 40.0 grams of maleic acid, 44.7 grams of cis-1,2,3,6-tetrahydrophthalic anhydride, 6.0 grams of a 0.15% aqueous ferrous sulfate heptahydrate solution, 1.3 grams of a 0.15% aqueous copper sulfate solution and 87.0 grams of 50% by weight aqueous sodium hydroxide. The contents of the flask were heated to 91° C. A monomer solution of 145.0 grams of acrylic acid and 100.0 grams of deionized water, and an initiator solution of 7.5 grams of sodium persulfate, 41.7 grams of 30% by weight aqueous hydrogen peroxide and 50.0 grams of deionized water were prepared. 15.0 grams of glacial acrylic acid were added to the flask. After two minutes, 10.0 grams of the initiator solution were added to the flask. The contents of the flask were then heated to 100° C. The remainder of the monomer solution and initiator solution were then fed into the flask linearly and separately while stirring over two hours and thirty minutes. Once the additions were complete, 1.0 grams of sodium persulfate dissolved in 5.0 grams of deionized water was added. The system was kept at 100° C. for 30 minutes. The system was then cooled to 80° C. A solution of 5.0 grams of sodium metabisulfite dissolved in 20.0 grams of deionized water was added. The system was then cooled to 50° C. and the pH was adjusted from 3.6 to 7.4 with 164.0 grams of 50% by weight aqueous sodium hydroxide.

Workup

  1. customTo a one liter, 4-neck flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionthermometer, and inlets for the gradual addition of monomer and initiator solution
  4. temperatureThe contents of the flask were then heated to 100° C
  5. additionwas added
  6. waitThe system was kept at 100° C. for 30 minutes
  7. temperatureThe system was then cooled to 80° C
  8. additionwas added
  9. temperatureThe system was then cooled to 50° C.

Sources & evidence

ORD record
ord-7986964dee2b4d788e6e446ef97781bc
Source dataset
uspto-grants-1995_03
Patent number
US05395905

Reaction notes

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