Ethylene Oxide → 2-Hydroxyethyl ethyl(2-hydroxyethyl)phosphinate

HRID 878921Notes

Reaction equation

HRID 878921 reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][OH:8])(=[O:5])[OH:4])[CH3:2].[CH2:9]1[O:11][CH2:10]1.[OH-].[K+]>O>[CH2:1]([P:3]([CH2:6][CH2:7][OH:8])(=[O:4])[O:5][CH2:9][CH2:10][OH:11])[CH3:2]

Participants

5

Reactant 3

HCID 6354Ethylene Oxide2×HCID 14797Potassium HydroxideHCID 46832563HCID 46832563, compound

Product 1

HCID 468325682-Hydroxyethyl ethyl(2-hydroxyethyl)phosphinateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml five-neck flask equipped with gas inlet tube, thermometer, high-performance stirrer and reflux condenser with gas incineration is charged with 138 g (1 mol) of ethyl(2-hydroxyethyl)phosphinic acid (produced as in Example 8) and ethylene oxide is passed in. A reaction temperature of 70° C. is set, followed by further reaction for 1 h. The ethylene oxide takeup is 64.8 g. The acid number of the product is less than 1 mg KOH/g. 173 g (95% of theory) of 2-hydroxyethyl ethyl(2-hydroxyethyl)phosphinate as colorless, water-clear liquid were obtained.

Workup

  1. customA 500 ml five-neck flask equipped with gas inlet tube
  2. temperaturethermometer, high-performance stirrer and reflux condenser with gas incineration
  3. customA reaction temperature of 70° C.
  4. customfollowed by further reaction for 1 h

Sources & evidence

ORD record
ord-dcdef202caef4c69a3b24384e2ce8e18
Source dataset
uspto-grants-2015_03
Patent number
US08987490B2

Reaction notes

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