Epichlorohydrin → HCID 88638245, compound

HRID 648787Notes

Reaction equation

HRID 648787 reaction equation
[P:1]([O-:21])([O-:20])([O:3][CH2:4][CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:2].[CH2:22]([CH:24]1[O:26][CH2:25]1)[Cl:23].[OH-].[Na+:28]>>[P:1]([O-:20])([O:21][CH2:25][CH:24]([OH:26])[CH2:22][Cl:23])([O:3][CH2:4][CH:5]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:2].[Na+:28]

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 21832863HCID 21832863, compound

Product 1

HCID 88638245HCID 88638245, compoundYield 82.3%

Procedure

20 g (0.057 moles) of mono2-hexyldecyl phosphate having a purity of 92% (AV1=167.2, AV2=329.8) was dispersed in 59.6 ml of 1N sodium hydroxide aqueous solution, at which the acid value of the reaction system was 39.5. While keeping the reaction system at 80° C., 16.5 g (0.178 moles) of epichlorohydrin was gradually added, followed by agitation at the temperature for 8 hours. The acid value of the reaction system was approximately zero, revealing that the conversion rate of the phosphoric monoester was almost 100%. The reaction solution was analyzed by HPLC. The chromatography showed peaks corresponding to hydrolysate or epichlorhidrine and a new reaction product. The resulting product was collected by HPLC and the solvent was distilled off under reduced pressure to obtain 20.5 g (yield 82.3%) of sodium 2-hexyldecyl 2-hydroxy-3-chloropropyl phosphate.

Workup

  1. customat 80° C.
  2. customThe resulting product was collected by HPLC
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-60eac515339846b89874d3dc01cd3cc9
Source dataset
uspto-grants-1988_04
Patent number
US04736051

Reaction notes

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