Epichlorohydrin → HCID 88641557, compound

HRID 648789Notes

Reaction equation

HRID 648789 reaction equation
[P:1]([O-:23])([O-:22])([O:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:2].[OH-].[K+:25].[CH2:26]([CH:28]1[O:30][CH2:29]1)[Cl:27]>>[P:1]([O-:22])([O:23][CH2:29][CH:28]([OH:30])[CH2:26][Cl:27])([O:3][CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:2].[K+:25]

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 131715487HCID 131715487, compound

Product 1

HCID 88641557HCID 88641557, compoundYield 67.8%

Conditions

Temperature
80 °C

Procedure

20 g (0.052 moles) of monooctadecenyl phosphate having a purity of 90% (AV1=165.0, AV2=323.2) was charged into a reactor, to which 58.8 ml of 1N potassium hydroxide aqueous solution was added and agitated at 80° C. to obtain uniform solution, at which the acid value of the reaction system was 40.2. While keeping the reaction system at 80° C., 24.1 g (0.26 moles) of epichlorohydrin was gradually dropped, followed by agitation at the temperature for 6 hours. The acid value of the reaction system was approximately zero, revealing that the reaction rate of the phosphoric monoester was almost 100%. The resulting product was collected by HPLC and the solvent was distilled off under reduced pressure to obtain 16.9 g (yield 67.8%) of potassium octadecenyl 2-hydroxy-3-chloropropyl phosphate.

Workup

  1. additionwas added
  2. customto obtain uniform solution
  3. customat 80° C.
  4. customThe resulting product was collected by HPLC
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-183addcb3a4c40d99d3c5bbb62ae60d5
Source dataset
uspto-grants-1988_04
Patent number
US04736051

Reaction notes

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