Ethylene Oxide → 2-Hydroxyethyl ethyl(3-hydroxypropyl)phosphinate

HRID 1911725Notes

Reaction equation

HRID 1911725 reaction equation
[CH2:1]([P:3]([CH2:6][CH2:7][CH2:8][OH:9])(=[O:5])[OH:4])[CH3:2].[CH2:10]1[O:12][CH2:11]1.[OH-].[K+]>O>[CH2:1]([P:3]([CH2:6][CH2:7][CH2:8][OH:9])(=[O:4])[O:5][CH2:10][CH2:11][OH:12])[CH3:2]

Participants

5

Reactant 3

HCID 6354Ethylene Oxide2×HCID 14797Potassium HydroxideHCID 86656674Ethyl-3-hydroxypropylphosphinic acid

Product 1

HCID 866566782-Hydroxyethyl ethyl(3-hydroxypropyl)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 152 g (1 mol) of ethyl(3-hydroxypropyl)phosphinic acid (produced similarly to Example 13). Ethylene oxide is passed in at room temperature. A reaction temperature of 70° C. is set with cooling, followed by further reaction at 80° C. for 1 hour. The ethylene oxide takeup is 64.8 g. The acid number of the product is less than 1 mg KOH/g. 186 g (95% of theory) of 2-hydroxyethyl ethyl(3-hydroxy-propyl)phosphinate are obtained as colorless, water-clear liquid.

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. customproduced similarly to Example 13)
  4. customis passed in at room temperature
  5. customA reaction temperature of 70° C.
  6. temperaturewith cooling
  7. customfollowed by further reaction at 80° C. for 1 hour

Sources & evidence

ORD record
ord-6c6ed1575928475db84bb9214c6d8d6e
Source dataset
uspto-grants-2013_12
Patent number
US08604108B2

Reaction notes

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