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Hydrogen Peroxide → Allyl methacrylate

HRID 1415718
Notes
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Reaction equation

HRID 1415718 reaction equation
P(=O)(O)(O)O.OO.[N+]([O-])([O-])=O.C([N+](CCCCCCCC)(CCCCCCCC)C)CCCCCCC.[C:38]([O:43][CH2:44][CH:45]1O[CH2:46]1)(=[O:42])[C:39]([CH3:41])=[CH2:40]>O.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+].C1(C)C=CC=CC=1>[C:38]([O:43][CH2:44][CH:45]=[CH2:46])(=[O:42])[C:39]([CH3:41])=[CH2:40]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 1004Phosphoric AcidHCID 7837Glycidyl methacrylateHCID 110590751-Octanaminium, N-methyl-N,N-dioctyl-, nitrate

Product 1

HCID 7274Allyl methacrylate

Reagents, catalysts & solvents 3

HCID 150191
Sodium Tungstate Dihydrate
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

An aqueous solution containing 1.32 g (0.004 mole), of sodium tungstate dihydrate 1.0 g (0.01 mole) of phosphoric acid and 12.5 g (0.12 mole) of 30% hydrogen peroxide in 18 ml of water (mixture pH=2.05) was added to a 24 ml toluene solution containing 7.5 g (0.06 mole) of allyl methaccrylate and 1.0 g (0.0023 equiv.) trioctylmethylammonium nitrate. The mixture was stirred at 45° C. for 30 hrs and was stopped when gas chromotrography showed that almost all starting material had disappeared and a major new peak having identical retention time as commercial glycidyl methacrylate had appeared. The mixture was cooled and the organic layer was separated and washed three time with 10 ml portions of water. It was then dried over magnesium sulfate, filtered and concentrated in vacuo to give 9.8 g of a viscous amber liquid.

Workup

  1. additionAn aqueous solution containing 1.32 g (0.004 mole)
  2. temperatureThe mixture was cooled
  3. customthe organic layer was separated
  4. washwashed three time with 10 ml portions of water
  5. dry with materialIt was then dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5edefafb980a419aabd73c9a987b6825
Source dataset
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05908943

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes