Hydrogen Peroxide → Styrene Oxide

HRID 1768395Notes

Reaction equation

HRID 1768395 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.NC(N)=[O:11].C(=O)(O)[O-].[Na+].OO>O.S([O-])([O-])(=O)=O.[Mn+2]>[CH2:1]1[O:11][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 7501StyreneHCID 516892Sodium Bicarbonate

Product 1

HCID 7276Styrene Oxide

Reagents, catalysts & solvents 2

HCID 24580Manganese SulfateCatalystHCID 962WaterSolvent

Procedure

To a mechanically stirred solution of commercial grade styrene (10.0 mol), commercial grade urea (26.6 mol), laboratory grade sodium bicarbonate (3.7 mol) and manganese sulphate (0.01 mol) in 2.50 L of water at 15° C. is added commercial grade 50% aqueous hydrogen peroxide (22.0 mol) slowly over a period of 5 hours. After 5.5 hours a separating funnel separated the organic layer of the reaction mixture. The crude styrene oxide was distilled to yield styrene oxide. The conversion to epoxide is 99% with selectivity 95%.

Workup

  1. customAfter 5.5 hours a separating funnel separated the organic layer of the reaction mixture
  2. distillationThe crude styrene oxide was distilled

Sources & evidence

ORD record
ord-8b6306d29f284af089d4897f962602fb
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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