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

HRID 576018Notes

Reaction equation

[CH2:1]([P:3]([CH2:10][CH2:11][CH2:12][NH2:13])(=[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.O=[Ti].[K+].[K+]>[CH2:1]([P:3]([CH2:10][CH2:11][CH2:12][NH2:13])(=[O:9])[O:4][CH2:5][CH2:6][OH:16])[CH3:2]

Participants

Conditions

Temperature: 200 °C

Procedure

To 414 g (2 mol) of butyl ethyl(3-aminopropyl)phosphinate (produced as in Example 14) are added 155 g (2.5 mol) of ethylene glycol and 0.4 g of potassium titanyl oxalate and the mixture is stirred at 200° C. for 2 h. Gradual evacuation is applied to distill off volatiles, leaving 374 g (96% of theory) of 2-hydroxyethyl ethyl-(3-aminopropyl)phosphinate.

Workup

distillationto distill off volatiles

Sources & evidence

ORD record: ord-750eb5afa1e140ca816865f9ff42ca09
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09035088B2

Reaction notes

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