1,4-Butanediol → 1,4-Butanediol bis(dichlorophosphate)

HRID 84974Notes

Reaction equation

HRID 84974 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[CH2:6]([OH:11])[CH2:7][CH2:8][CH2:9][OH:10]>>[P:1]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][O:11][P:1]([Cl:5])([Cl:3])=[O:2])([Cl:5])([Cl:3])=[O:2]

Participants

3

Reactant 2

HCID 80641,4-ButanediolHCID 24813Phosphorus oxychloride2×

Product 1

HCID 885924331,4-Butanediol bis(dichlorophosphate)

Procedure

A 500 ml four-necked flask with stirrer, thermometer, dropping funnel with pressure compensation and reflux condenser was charged with 300.0 g of phosphoryl chloride at 20° C. Then a vacuum of 200 mbar was applied and 45.0 g of 1,4-butanediol were added dropwise over the course of 45 minutes. Cooling in an ice-water bath kept the temperature at 20° C. A clear, colourless reaction mixture was formed. After the end of the metered addition, the pressure was lowered to about 100 mbar, and stirring was continued for 2 hours. A distillation bridge was then mounted on, and the excess of phosphoryl chloride was removed by distillation. This left 144.9 g (91%) of 1,4-butanediol bis(dichlorophosphate).

Workup

  1. customA 500 ml four-necked flask with stirrer, thermometer, dropping
  2. temperaturefunnel with pressure compensation and reflux condenser
  3. temperatureCooling in an ice-water bath
  4. customat 20° C
  5. customA clear, colourless reaction mixture was formed
  6. additionAfter the end of the metered addition
  7. customwas removed by distillation

Sources & evidence

ORD record
ord-7f95c8e53f644820affa3a854b648c8d
Source dataset
uspto-grants-2014_09
Patent number
US08846967B2

Reaction notes

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