Hydrogen Peroxide → Styrene Oxide

HRID 1768394Notes

Reaction equation

HRID 1768394 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCCCCCCCCCCC.NC(N)=[O:23].C(=O)(O)[O-].[Na+].OO>O.S([O-])([O-])(=O)=O.[Mn+2]>[CH2:1]1[O:23][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 7501StyreneHCID 8182DodecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 7276Styrene Oxide

Reagents, catalysts & solvents 2

HCID 24580Manganese SulfateCatalystHCID 962WaterSolvent

Procedure

To a mechanically stirred solution of styrene (1.0 mol), dodecane (0.1 mol), urea (20.8 mol), sodium bicarbonate (0.3 mol) and manganese sulphate (0.001 mol) in 500 ml of water at 40° C. is added 50% aqueous hydrogen peroxide (2.2 mol) drop-wise over a period of 4 hours. The reaction was allowed to stir for 8 hours. After 8 hours a separating funnel separated the organic layer of the reaction mixture. The aqueous layer was extracted with 4×20 mL diethyl ether. The combined organic layer was distilled to yield styrene oxide. The conversion to epoxide is 99% with selectivity 94%.

Workup

  1. customAfter 8 hours a separating funnel separated the organic layer of the reaction mixture
  2. extractionThe aqueous layer was extracted with 4×20 mL diethyl ether
  3. distillationThe combined organic layer was distilled

Sources & evidence

ORD record
ord-d8370d9b7d7442b590a2cd4c75b080d8
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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