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US4368162A
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Process for producing aminomethylphosphonic acid
Assignee: Novartis Corp
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Filing: 1981-11-02
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Granted: 1983-01-11
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Expires: 2001-11-02
Abstract
Abstract Aminomethylphosphonic acid is produced by reaction of a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms or a phenyl group, in the presence of a Lewis acid as catalyst, with an ester of the phosphorous acid of the formula ##STR2## wherein R 1 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a benzyl group, the 2-cyanoethyl group or the 2,2,2-trichloroethyl group, to give an N-carboxyaminomethylphosphonic acid derivative of the formula ##STR3## and subsequent hydrolysis thereof in an aqueous medium and in the presence of a strong acid. Aminomethylphosphonic acid can be used as active substance for influencing plant growth, and as intermediate for producing herbicidal active substances.
Inventors
- 👤 Ludwig Maier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 07:34
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808; C07F9/40; C07F9/4003; C07F9/4006
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
134 words
A process for producing aminomethylphosphonic acid of the formula I ##STR8## which process comprises reacting a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II ##STR9## wherein R is an alkyl group having 1 to 4 carbon atoms, or a phenyl group, at a temperature of 90°-150° C. in the presence of a Lewis acid as catalyst, with an ester of the phosphorous acid of the formula III ##STR10## wherein R 1 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a benzyl group, the 2-cyanoethyl group or the 2,2,2-trichloroethyl group, to give an N-carboxyaminomethylphosphonic acid derivative of the formula IV ##STR11## wherein R and R 1 have the meanings defined above, and subsequently hydrolysing this derivative in an aqueous medium, in the presence of a strong acid, to obtain aminomethylphosphonic acid.
Claim 2
Dependent Claim
134 words
A process for producing aminomethylphosphonic acid of the formula I ##STR8## which process comprises reacting a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II ##STR9## wherein R is an alkyl group having 1 to 4 carbon atoms, or a phenyl group, at a temperature of 90°-150° C. in the presence of a Lewis acid as catalyst, with an ester of the phosphorous acid of the formula III ##STR10## wherein R 1 is an alkyl group having 1 to 5 carbon atoms, a phenyl group, a benzyl group, the 2-cyanoethyl group or the 2,2,2-trichloroethyl group, to give an N-carboxyaminomethylphosphonic acid derivative of the formula IV ##STR11## wherein R and R 1 have the meanings defined above, and subsequently hydrolysing this derivative in an aqueous medium, in the presence of a strong acid, to obtain aminomethylphosphonic acid.
Claim 3
Dependent Claim
23 words
A process according to claim 1, wherein the Lewis acid used is: boron trifluoride etherate, titanium tetrachloride, tin tetrachloride, iron(III)chloride or aluminium chloride.
Claim 4
Dependent Claim
15 words
A process according to claim 1, wherein the Lewis acid used is boron trifluoride etherate.
Claim 5
Dependent Claim
28 words
A process according to claim 1, wherein the Lewis acid is used in an amount of 1-10 mol %, relative to hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II.
Claim 6
Dependent Claim
28 words
A process according to claim 1, wherein the Lewis acid is used in an amount of 4-6 mol %, relative to hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II.
Claim 7
Dependent Claim
37 words
A process according to claim 1, wherein the reaction of a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II with an ester of the phosphorous acid of the formula III is performed at a temperature of 120°-150° C.
Claim 8
Dependent Claim
27 words
A process according to claim 1, wherein there is used as starting material a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II wherein R is methyl or ethyl.
Claim 9
Dependent Claim
42 words
A process according to claim 1, wherein there is used as starting material an ester of the phosphorous acid of the formula III wherein R 1 is an alkyl group having 1 to 3 carbon atoms, the 2-cyanoethyl group or 2,2,2-trichloroethyl group.
Claim 10
Dependent Claim
26 words
A process according to claim 1, wherein the ester of the phosphorous acid of the formula III is used in an excess of 3-10 mol %.
Claim 11
Dependent Claim
43 words
A process according to claim 1, wherein the strong acid used, in the presence of which the hydrolysis of an N-carboxy-aminomethylphosphonic acid derivative of the formula IV is performed, is: hydrochloric acid, hydrobromic acid, hydriodic acid, sulfuric acid, phosphoric acid or p-toluenesulfonic acid.
Claim 12
Dependent Claim
33 words
A process according to claim 1, wherein the strong acid used, in the presence of which the hydrolysis of an N-carboxy-aminomethylphosphonic acid derivative of the formula IV is performed, is a hydrohalic acid.
Claim 13
Dependent Claim
41 words
A process according to claim 1, wherein the hydrolysis of an N-carboxy-aminomethylphosphonic acid derivative of the formula IV is performed in water, or in a mixture of water with acetonitrile, methanol or ethanol, at the reflux temperature of the reaction medium.
Claim 14
Dependent Claim
143 words
A process according to claim 1, wherein a hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II, wherein R is methyl or ethyl, is reacted in the presence of 4-6 mol % of boron trifluoride etherate, relative to the employed hexahydro-1,3,5-triazine-N,N',N"-tris-carboxylic acid ester of the formula II, at a temperature of 120°-150° C., with an ester of the phosphorous acid of the formula III, wherein R 1 is an alkyl group having 1 to 3 carbon atoms, a 2-cyanoethyl group or 2,2,2-trichloroethyl group, to give an N-carboxy-aminomethylphosphonic acid derivative of the formula IV, wherein R is methyl or ethyl, and R 1 is an alkyl group having 1 to 3 carbon atoms, 2-cyanoethyl or 2,2,2-trichloroethyl; and subsequently hydrolysing this derivative in an aqueous medium, in the presence of hydrochloric acid or hydrobromic acid, at the reflux temperature of the reaction medium, to obtain aminomethylphosphonic acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-01-10 | 1986-07-12 | 1987-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-01-10 | 1990-07-12 | 1991-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-01-10 | 1994-07-12 | 1995-01-11 | $7700.00 | Window Closed / Lapsed |