1-Octanol → Diglycidyl ether

HRID 1937070Notes

Reaction equation

HRID 1937070 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3]CCCCC.[OH-:10].[Na+].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl.[Cl-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:12]([O:10][CH2:3][CH:2]1[O:9][CH2:1]1)[CH:14]1[O:16][CH2:15]1

Participants

6

Reactant 4

HCID 9571-OctanolHCID 5234Sodium ChlorideHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide2×

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Octanol (132 g, 1 mol) was added to a round-bottomed four-neck flask equipped with an agitator, reflux condenser and thermometer at 30° C. Tetrabutylammonium bromide (16.1 g, 0.050 mol) and sodium hydroxide (61.9 g, 1.5 mol) were further added to the flask and stirred, and then, epichlorohydrin (140.1 g, 1.5 mol) was added dropwise for 10 minutes. After the mixture was stirred for 3 hours at the same temperature, by-products such as sodium chloride and sodium hydroxide were filtered off. The unreacted epichlorohydrin was reused via recovery process such as distillation. Then, glycidyl ether compound as the desired product was obtained by a simple filtration.

Workup

  1. customequipped with an agitator
  2. temperaturereflux condenser
  3. customthermometer at 30° C
  4. filtrationwere filtered off
  5. distillationThe unreacted epichlorohydrin was reused via recovery process such as distillation

Sources & evidence

ORD record
ord-27adc02a10b84d49a157a5affbb85927
Source dataset
uspto-grants-2002_05
Patent number
US06392064B2

Reaction notes

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