Epichlorohydrin → Sodium butyl 2-hydroxy-3chloropropyl phosphate

HRID 648788Notes

Reaction equation

HRID 648788 reaction equation
[P:1]([O-:9])([O-:8])([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].[OH-].[Na+:11].[CH2:12]([CH:14]1[O:16][CH2:15]1)[Cl:13]>>[P:1]([O-:9])([O:8][CH2:15][CH:14]([OH:16])[CH2:12][Cl:13])([O:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].[Na+:11]

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 12691398Butyl phosphate

Product 1

HCID 86743212Sodium butyl 2-hydroxy-3chloropropyl phosphateYield 86.5%

Conditions

Temperature
70 °C

Procedure

20 g (0.13 moles) of monobutyl phosphate having a purity of 99% (AV1=360.6, AV2=721.3) was charged into a reactor, to which 129 ml of 1N sodium hydroxide aqueous solution was added and agitated at 70° C. to obtain uniform solution, at which the acid value of the reaction system was 46.7. While keeping the reaction system at 70° C., 59.2 g (0.64 moles) of epichlorohydrin was gradually dropped, followed by agitation at the temperature for 20 hours. The acid value of the reaction system was approximately zero, revealing that the conversion 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 30.2 g (yield 86.5%) of sodium butyl 2-hydroxy-3-chloropropyl phosphate.

Workup

  1. additionwas added
  2. customto obtain uniform solution
  3. customat 70° C.
  4. customThe resulting product was collected by HPLC
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-311f385075b44f298805aeb9e2116330
Source dataset
uspto-grants-1988_04
Patent number
US04736051

Reaction notes

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