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

HRID 1914969Notes

Reaction equation

HRID 1914969 reaction equation
[CH2:1]([P:3]([CH2:10][CH2:11][CH2:12][OH:13])(=[O:9])[O:4][CH2:5][CH2:6]CC)[CH3:2].C(O)C[OH:16]>C([O-])(C([O-])=O)=O.C([O-])(C([O-])=O)=O.O=[Ti+2].[K+].[K+]>[CH2:1]([P:3]([CH2:10][CH2:11][CH2:12][OH:13])(=[O:9])[O:4][CH2:5][CH2:6][OH:16])[CH3:2]

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 86656676Butyl ethyl-3-hydroxypropylphosphinate

Product 1

HCID 866566782-Hydroxyethyl ethyl(3-hydroxypropyl)phosphinateYield 111.9%

Reagents, catalysts & solvents 1

HCID 56841016Potassium titanium oxalateCatalyst

Conditions

Temperature
200 °C

Procedure

To 416 g (2 mol) of butyl ethyl(3-hydroxypropyl)phosphinate (produced as in Example 9) are added 155 g (2.5 mol) of ethylene glycol and 0.4 g of potassium titanyloxalate, followed by stirring at 200° C. for 2 h. Volatiles are distilled off by gradual evacuation to leave 439 g (98% of theory) of 2-hydroxyethyl ethyl(3-hydroxypropyl)phosphinate.

Workup

  1. distillationVolatiles are distilled off by gradual evacuation

Sources & evidence

ORD record
ord-65b0d4108f934a628e3df72217f06fe2
Source dataset
uspto-grants-2013_12
Patent number
US08614267B2

Reaction notes

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