Hydrogen Peroxide → Styrene Oxide

HRID 1768391Notes

Reaction equation

HRID 1768391 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>[CH2:1]1[O:23][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 5

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

Product 1

HCID 7276Styrene Oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mechanically stirred solution of styrene (0.1 mol), dodecane (0.01 mol), urea (2.08 mol), sodium bicarbonate (0.03 mol) in 50.0 ml of water at 20° C. is added 30% aqueous hydrogen peroxide (0.22 mol) drop-wise over a period of 5 h. After 5 h the organic layer of the reaction mixture was separated by a separating funnel. 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 95%.

Workup

  1. customAfter 5 h the organic layer of the reaction mixture was separated by a separating funnel
  2. extractionThe aqueous layer was extracted with 4×20 mL diethyl ether
  3. distillationThe combined organic layer was distilled

Sources & evidence

ORD record
ord-7c228b65bcde4168957f56f20fea6b69
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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