Epichlorohydrin → 1-Dodecyl glycidyl ether

HRID 2304975Notes

Reaction equation

HRID 2304975 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.[OH-].[Na+]>FC(F)(F)S(O)(=O)=O.O>[CH2:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:16]1[O:18][CH2:17]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 81931-DodecanolHCID 14798Sodium Hydroxide

Product 1

HCID 171631-Dodecyl glycidyl etherYield 114.3%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Dodecanol (167.4 g) and 8.1 g of trifluoromethanesulfonic acid were heated to 95° C. while stirring. To the reaction mixture, 166.5 g of epichlorohydrin was added dropwise over 1 hour, followed by stirring for 8 hours. After completion of the reaction, the reaction mixture was cooled to 50° C. Over 1 hour, 75 g of a 48% aqueous solution of sodium hydroxide was added dropwise at a temperature maintained at 50° C. After stirring for 3 hours, 120 mL of water was added to the reaction mixture to cause separation. The water layer thus occurred was removed. The residue was then washed twice with 100 mL of water, whereby 249 g of crude dodecyl glycidyl ether was obtained.

Workup

  1. stirringby stirring for 8 hours
  2. customAfter completion of the reaction
  3. temperaturemaintained at 50° C
  4. stirringAfter stirring for 3 hours
  5. customseparation
  6. customThe water layer thus occurred was removed
  7. washThe residue was then washed twice with 100 mL of water

Sources & evidence

ORD record
ord-13ba51e981a2462ca60ca58669b50e59
Source dataset
uspto-grants-2002_08
Patent number
US06437196B1

Reaction notes

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