Process for the preparation of N-phosphonomethylglycine
AssigneeBASF SE
InventorsChristian Wulff, Stefan Orsten, Alfred Oftring
Life of this patent
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Abstract
The present invention relates to a process for the preparation of N-phosphonomethylglycine by reacting a hexahydrotriazine derivative with a triacyl phosphite. The process gives N-phosphonomethylglycine in high yield and in a simple and inexpensive manner.
Claims25
A process for the preparation of N-phosphonomethylglycine, wherein
- a) hexahydrotriazine derivative of the formula II
- 10
- in which X is CN, COOZ, CONR1R2 or CH2OY,
- Y is H or a radical which is readily exchangable for H,
- Z is H, an alkali metal, alkaline earth metal, C1-C18-alkyl or aryl, which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl,
- R1 and R2 can be identical or different and are H or C1-C4-alkyl,
- is reacted with a triacyl phosphite of the formula III
- P(OCOR3)3 (III)
- in which the radicals R3, which can be identical or different, are C1-C18-alkyl or aryl which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl, and
- b) the product obtained is hydrolyzed, and, if X is CH2OY, oxidized.
A process for the preparation of a phosphono compound of the formula I
- 12
- in which the radicals R3, which can be identical or different, are C1-C18-alkyl or aryl which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl, and
- X us CN, COOZ, CONR1R2 or CH2OY,
- Y is H or a radical which is readily exchangeable for H;
- Z is H, an alkali metal, alkaline earth metal, C1-C18-alkyl or aryl, which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl;
- R1 and R2, which can be identical or different, are H or C1-C4-alkyl, in which a hexahydrotriazine derivative of the formula II
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- is reacted with a triacyl phosphite of the formula III
- P(OCOR3)3 (III)
- in which R3 and X are as defined above.
A process as claimed in any of the preceding claims, wherein X is CN or COOZ.
A process as claimed in any of the preceding claims, wherein R3 is phenyl which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl, or is CH3.
A process as claimed in any of the preceding claims, wherein step (a) is carried out in an organic solvent.
A process as claimed in any of the preceding claims, wherein the compounds of the formulae II and III in employed in essentially equivalent amounts.
A phosphono compound of the formula I
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- in which the radicals R3, which can be identical or different, are C1-C18-alkyl or aryl which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl, and
- X is CN, COOZ, CONR1R2 or CH2OY,
- Y is H or a radical which is readily exchangeable for H;
- Z is H, an alkali metal, alkaline earth metal, C1-C18-alkyl or aryl, which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl;
- R1 and R2, which can be identical or different, are H or C1-C4-alkyl, or a salt thereof.
An intermediate obtainable by reacting a hexahydrotriazine derivative of the formula II
- 16
- in which X is CN, COOZ, CONR1R2 or CH2OY,
- Y is H or a radical which is readily exchangeable for H;
- Z is H, an alkali metal, alkaline earth metal, C1-C18-alkyl or aryl, which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl;
- R1 and R2 can be identical or different and are H or C1-C4-alkyl,
- is reacted with a triacyl phosphite of the formula III
- P(OCOR3)3 (III)
- in which the radicals R3, which can be identical or different, are C1-C18-alkyl or aryl which is unsubstituted or substituted by C1-C4-alkyl, NO2 or OC1-C4-alkyl.
Dependencies are inferred from the claim text.