CH275435A - Process for producing a phosphonic acid. - Google Patents
Process for producing a phosphonic acid.Info
- Publication number
- CH275435A CH275435A CH275435DA CH275435A CH 275435 A CH275435 A CH 275435A CH 275435D A CH275435D A CH 275435DA CH 275435 A CH275435 A CH 275435A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- sep
- producing
- aminomethylphosphonic
- phosphonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 2
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
- 229940106681 chloroacetic acid Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FZXSSJIKXCFPDP-UHFFFAOYSA-N chloro(dichlorophosphoryl)methane Chemical compound ClCP(Cl)(Cl)=O FZXSSJIKXCFPDP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
Verfahren zur Herstellung einer Phosphonsäure. Die Aminomethylphosphonsäure-N-N-di- essigsäure ist als wirksamer Komplexbildner beschrieben worden [Cr. Schwarzenbach, H. Ackermann, R. Ruckstuhl, Helv. 32, 1175 (1949)]. Der Weg zu dieser Substanz führt über das Chlormethylphosphonsäuredichlorid zur Chlormethylphosphonsäure, die mit Imino- diessigsäure umgesetzt wird.
Dieses Verfahren ist für die Durehfüh- rung in technischem Massstab kaum geeignet. 5o muss das eine Ausgangsprodukt des Ver fahrens, das Chlormethylphosphonsäuredichlo- rid, dureh Erhitzen von polymerem Form aldehyd mit Phosphortrichlorid auf 200 unter Druck hergestellt werden, was bei Herstellung grösserer Mengen begreiflieherweise einen er heblichen apparativen Aufwand erfordert.
Weiter benötigt der Umsatz von Chlormethy 1- phosphonsäure mit Iminodiessigsäure nach eigenen Messungen, die durch die zitierte Li teratur bestätigt wurden, über eine Woche, bis er bei 98 zu drei Vierteln vollzogen ist. Das zweite Ausgangsprodukt des Verfahrens, die Iminodiessigsäure, wird nach den bis jetzt. bekannten Verfahren nur in geringer Aus beute erhalten.
Es wurde nun gefunden, dass man auf ein fache reise und mit vorzüglicher Ausbeute zu der Aminomethylphosphonsäure-N-N-diessig- säure gelangenkann, indem man die leicht erhält liehe Aminomethylphosphonsäure mit Chlor- essigsäure umsetzt. Die Aminomethyiphosphon- säure und ihre Herstellung ist im USA-Patent Nr. 2328358 beschrieben.
Wie gefunden wurde, kann man, ohne die in der genannten Patentschrift erwähnten Zwischenprodukte zu isolieren, mit 80 bis 90 0/0 Ausbeute direkt zu der bei 320 unter Zerset zung schmelzenden Aminomethylphosphon- säure gelangen.
Infolge dieser Vereinfachung ist die Ver bindung leicht zugänglich geworden. Gegenstand des Patentes ist somit ein Ver fahren zur Herstellung der als Zwischenpro dukt verwendbaren Aminomethyiphosphon- säure-N-N-diessigsäure, das dadurch gekenn zeichnet ist, dass man Aminomethylphosphon- säure in alkalischer Lösung mit Chloressig säure umsetzt, wobei man den PH-Wert zwi schen 9,5 und 11 hält.
<I>Beispiel:</I> 22g Aminomethylphosphonsäure werden mit 8 g Ätznatron in 200 cm3 Wasser gelöst und mit einer Lösung von 42 g Chloressig säure und 17,8 g Ätznatron in 80 em3 Wasser vermischt. Nun wird auf dem Wasserbad unter Turbinieren auf 90 erwärmt. Durch Zutropfen von 55 em3 30 11/o iger Natronlauge wird die Lösung gerade thymolphthaleinalka- lisch Gehalten. Nach etwa 45 Minuten bleibt das PH konstant.
Die Lösung wird mit Aktiv kohle verrührt, filtriert, mit 80 ein:' konzen trierter Salzsäure angesäuert und nach dem Abkühlen mit 20 cm' Äthanol versetzt. Die ausgefallene Kristallmasse wird abgesaugt und getroeknet. 'Man erhält so die gewünschte Aminomethylphosphonsäure-N-N-diessigsäure in Form farbloser Kristalle, die bei 213 unter Zersetzung schmelzen.
Die Auswage beträgt 36,2 g, entsprechend einer Ausbeute von 801/o der Theorie.
Die Verbindung ist in heissem Wasser gut löslieli; in den gewöhnliehen organischen Lö sungsmitteln löst sie sich wenig.
EMI0002.0010
Analyse. <SEP> Ber. <SEP> C <SEP> : <SEP> 26,45% <SEP> Gef. <SEP> C <SEP> : <SEP> <B>26,661/0</B>
<tb> H <SEP> : <SEP> -1,4.1% <SEP> H <SEP> : <SEP> 4,68 <SEP> %
<tb> N: <SEP> 6,170/'o <SEP> N: <SEP> 6,15%
Process for producing a phosphonic acid. The aminomethylphosphonic acid-N-N-diacetic acid has been described as an effective complexing agent [Cr. Schwarzenbach, H. Ackermann, R. Ruckstuhl, Helv. 32, 1175 (1949)]. The route to this substance leads via the chloromethylphosphonic acid dichloride to chloromethylphosphonic acid, which is reacted with iminodiacetic acid.
This method is hardly suitable for implementation on an industrial scale. One of the starting products of the process, chloromethylphosphonic acid dichloride, has to be produced by heating polymeric formaldehyde with phosphorus trichloride to 200 under pressure, which, of course, requires considerable expenditure on equipment when producing larger quantities.
Furthermore, the conversion of chloromethyl 1-phosphonic acid with iminodiacetic acid takes over a week, according to our own measurements, which have been confirmed by the cited literature, until it is three-quarters complete at 98. The second starting product of the process, iminodiacetic acid, is used according to the until now. known method only obtained in low loot from.
It has now been found that aminomethylphosphonic acid-N-N-diacetic acid can be obtained easily and with excellent yield by reacting the easily obtained aminomethylphosphonic acid with chloroacetic acid. Aminomethylphosphonic acid and its preparation is described in US Pat. No. 2,328,358.
As has been found, without isolating the intermediates mentioned in the patent mentioned, it is possible to obtain the aminomethylphosphonic acid which melts at 320 with decomposition directly in a yield of 80 to 90%.
As a result of this simplification, the connection has become easily accessible. The subject of the patent is thus a process for the production of aminomethylphosphonic acid-NN-diacetic acid, which can be used as an intermediate product, which is characterized in that aminomethylphosphonic acid is reacted in alkaline solution with chloroacetic acid, with the pH between tween 9.5 and 11 holds.
<I> Example: </I> 22g aminomethylphosphonic acid are dissolved with 8 g caustic soda in 200 cm3 water and mixed with a solution of 42 g chloroacetic acid and 17.8 g caustic soda in 80 em3 water. It is now heated to 90 on the water bath with turbines. The solution is just thymolphthalein-alkaline by adding 55 cubic meters of 30 11 / o sodium hydroxide solution. After about 45 minutes the pH remains constant.
The solution is stirred with activated charcoal, filtered, acidified with 80 a: 'concentrated hydrochloric acid and, after cooling, mixed with 20 cm' of ethanol. The precipitated crystal mass is filtered off with suction and dried. The desired aminomethylphosphonic acid-N-N-diacetic acid is thus obtained in the form of colorless crystals which melt at 213 with decomposition.
The final weight is 36.2 g, corresponding to a yield of 801 / o of theory.
The compound dissolves well in hot water; It does not dissolve very much in the usual organic solvents.
EMI0002.0010
Analysis. <SEP> Ber. <SEP> C <SEP>: <SEP> 26.45% <SEP> Found <SEP> C <SEP>: <SEP> <B> 26.661 / 0 </B>
<tb> H <SEP>: <SEP> -1.4.1% <SEP> H <SEP>: <SEP> 4.68 <SEP>%
<tb> N: <SEP> 6.170 / 'o <SEP> N: <SEP> 6.15%
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH275435T | 1949-06-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH275435A true CH275435A (en) | 1951-05-31 |
Family
ID=4480239
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH275435D CH275435A (en) | 1949-06-30 | 1949-06-30 | Process for producing a phosphonic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH275435A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014012986A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-phosphonomethyliminodiacetic acid |
US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
-
1949
- 1949-06-30 CH CH275435D patent/CH275435A/en unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014012986A1 (en) | 2012-07-17 | 2014-01-23 | Straitmark Holding Ag | Method for the synthesis of n-phosphonomethyliminodiacetic acid |
US9676799B2 (en) | 2012-07-17 | 2017-06-13 | Straitmark Holding Ag | Method for the synthesis of N-(phosphonomethyl)glycine |
US10280189B2 (en) | 2012-07-17 | 2019-05-07 | Monsanto Technology Llc | Method for the synthesis of aminoalkylenephosphonic acid |
US10364262B2 (en) | 2012-07-17 | 2019-07-30 | Monsanto Technology Llc | Method for the synthesis of N-phosphonomethyliminodiacetic acid |
US10464958B2 (en) | 2012-07-17 | 2019-11-05 | Monsanto Technology Llc | Method for the synthesis of alpha-aminoalkylenephosphonic acid |
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