Reaction equation
[N:1]1([CH2:7][P:8](=[O:11])([OH:10])[OH:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-:12].[Na+].Cl>O>[P:8]([CH2:7][NH:1][CH2:6][C:5]([OH:12])=[O:4])([OH:9])([OH:10])=[O:11].[NH2:1][CH2:7][P:8](=[O:9])([OH:11])[OH:10].[OH:4][CH2:3][CH2:2][NH:1][CH2:7][P:8](=[O:9])([OH:11])[OH:10]Participants
Reactant 3
Product 3
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 275 °C
Procedure
In a 100 mL Monel autoclave were mixed 4.0 g (22 mmol) of 4-morpholinylmethylphosphonic acid and 26.3 g (330 mmol) of a 50.3% solution of NaOH. The vessel was sealed and heated to 275° C. for four hours. The reaction was cooled to room temperature and the residual pressure generated by the reaction was vented off. The reaction mixture was a white slurry which was diluted with 10 mL of H2O and neutralized with 27.2 mL (330 mmol) of conc. HCl. This solution was concentrated to dryness. The residue was taken up in conc. HCl and the precipitated NaCl was filtered off. The filtrate was concentrated and purified by ion exchange chromatography to yield 1.29 g (34.7%) of N-phosphonomethylglycine, 0.57 g (23%) of aminomethylphosphonic acid, 0.67 g (19.6%) of N-(2-hydroxyethyl)aminomethylphosphonic acid, and 0.46 g (11.6%) of unreacted starting material.
Workup
- customThe vessel was sealed
- temperatureThe reaction was cooled to room temperature
- concentrationThis solution was concentrated to dryness
- filtrationthe precipitated NaCl was filtered off
- concentrationThe filtrate was concentrated
- custompurified by ion exchange chromatography
Sources & evidence
- ORD record
- ord-cfea267b03ce4365b5c51e32b62eb2d8
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04587061
Linked notes
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