DE573130C - Process for the production of water-soluble antimony salts - Google Patents
Process for the production of water-soluble antimony saltsInfo
- Publication number
- DE573130C DE573130C DEC42300D DEC0042300D DE573130C DE 573130 C DE573130 C DE 573130C DE C42300 D DEC42300 D DE C42300D DE C0042300 D DEC0042300 D DE C0042300D DE 573130 C DE573130 C DE 573130C
- Authority
- DE
- Germany
- Prior art keywords
- water
- antimony
- solution
- production
- sodium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001462 antimony Chemical class 0.000 title description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000001323 aldoses Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 2
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 claims 1
- 150000002927 oxygen compounds Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- -1 antimonyl lactates Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 208000006558 Dental Calculus Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 3
- 150000001463 antimony compounds Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002895 emetic Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001880 stiboryl group Chemical group *[Sb](*)(*)=O 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- SZOADBKOANDULT-UHFFFAOYSA-K antimonous acid Chemical compound O[Sb](O)O SZOADBKOANDULT-UHFFFAOYSA-K 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- UNKOHCAZUXZPIQ-UHFFFAOYSA-N oxoantimony;hydrate Chemical compound O.[Sb]=O UNKOHCAZUXZPIQ-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- AQKFVNLHZYOMKQ-WWNCWODVSA-M sodium;(2r,3r,4r,5r)-2,3,5,6-tetrahydroxy-4-[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate Chemical compound [Na+].[O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O AQKFVNLHZYOMKQ-WWNCWODVSA-M 0.000 description 1
- UPMFZISCCZSDND-FLGKMABCSA-M sodium;(2r,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Na+].OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C([O-])=O UPMFZISCCZSDND-FLGKMABCSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
- 235000019640 taste Nutrition 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
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung wasserlöslicher Antimonsalze Während die einfachen Salze des Antimons infolge Hydrolyse meist nicht klar in Wasser löslich sind, zeigt das komplex an Säure gebundene Antimonmolekül diese oft störend empfundenen Eigenschaften kaum mehr. Die Antimonylverbindungen haben aber in wässeriger Lösung vom Neutralpunkt oft stark abweichende Reaktion; der meist gebräuchliche Brechweinstein z. B. reagiert ziemlich stark s4uer. Beim Versuch, die saure Reaktion mit Alkali zu neutralisieren, trübt sich die Lösung unter Ausscheidung basischer Antimonverbindungen.Process for the preparation of water-soluble antimony salts During the simple salts of antimony are usually not clearly soluble in water due to hydrolysis the antimony molecule, which is complexly bound to the acid, shows this, which is often perceived as annoying Properties hardly any more. However, the antimonyl compounds are in aqueous solution often strongly deviating reaction from the neutral point; the most common emetic tartar z. B. reacts quite strongly. When trying the acidic reaction with alkali to neutralize, the solution becomes cloudy with the excretion of basic antimony compounds.
Ähnlich verhalten sich auch die Antimonyllaktate und -glykolate, welche nach den Verfahren der Patentschriften 98 939 bzw. 263 455 hergestellt werden können. So reagiert z. B. das nach der Patentschrift 263 455 erhaltene Antimonylglykolat in wässeriger Lösung sauer; diese saure Reaktion ist aber gerade sehr uner@viinscht, besonders bei therapeutischer Anwendung. - Versucht man nun eine Lösung des Antimonylglykolates zu neutralisieren, so trübt sich die Lösung, bevor sie neutral ist.The antimonyl lactates and glycolates behave similarly, which can be prepared by the process of patents 98,939 and 263,455. This is how z. B. the antimonyl glycolate obtained according to patent specification 263 455 acidic in aqueous solution; but this acidic reaction is very unlikely at the moment, especially for therapeutic use. - If one tries now a solution of the antimonyl glycolate to neutralize, the solution becomes cloudy before it is neutral.
Es wurde nun gefunden, daß man alkalibeständige, neutrale, leicht und klar in Wasser lösliche Antimonverbindungen herstellen kann, wenn man Antimonoxydhydrate in wässerigen Lösungen von Alkalimetallsalzen der Polyoxymonocarbonsäuren, hergestellt durch Oxydation von Aldosen, auflöst.It has now been found that alkali-resistant, neutral, easy and antimony compounds which are clearly soluble in water can be produced by using antimony oxyhydrates in aqueous solutions of alkali metal salts of polyoxymonocarboxylic acids by oxidation of aldoses, dissolves.
Zur Ausführung des Verfahrens wird Antimonoxydhydrat, hergestellt z. B. aus Brechweinstein, durch Behandeln desselben mit Mineralsäure in Natriumglykonatlösung gelöst und die neue Verbindung aus der Lösung durch Eindampfen oder Fällen mit Alkohol isoliert. Die auf diese Art erhaltenen Produkte sind in Wasser leicht löslich, besitzen aber eine schwach saure Reaktion, welche neutralisiert werden kann. Diese Lösungen sind j e nach dem Ausgangsmaterial stabil: oder trüben sich allmählich, rascher bei erhöhter Temperatur und um so schneller, je alkalischer sie sind. Diese Zersetzung kann leicht vermieden und alkalibeständige Lösungen können erhalten werden, wenn- man diesen weitere Mengen Natriumglykonat zufügt. Sie bleiben dann bei langemn Lagern oder auch bei stundenlangem Erhitzen in siedendem Wasserbad klar. Den so hergestellten Verbindungen können folgende Konstitutionsformeln gegeben werden. Das vorliegende Verfahren bedeutet gegenüber den eingangs erwähnten bekannten Verfahren einen Fortschritt, da es erlaubt, leicht lösliche und zugleich neutrale und beständige Antimonverbindungen herzustellen; diese sollen therapeutische sowie chemisch-technische Verwendung finden.To carry out the process, antimony oxide hydrate, produced e.g. B. from emetic tartar, dissolved by treating it with mineral acid in sodium glyconate solution and the new compound isolated from the solution by evaporation or precipitation with alcohol. The products obtained in this way are easily soluble in water, but have a weakly acidic reaction which can be neutralized. Depending on the starting material, these solutions are stable: or they become cloudy gradually, more quickly at elevated temperature and the more quickly the more alkaline they are. This decomposition can easily be avoided and alkali-resistant solutions can be obtained if further amounts of sodium glyconate are added to them. They then remain clear after long periods of storage or after hours of heating in a boiling water bath. The following constitutional formulas can be given to the compounds thus prepared. The present process represents an advance over the known processes mentioned at the beginning, since it allows the production of easily soluble and at the same time neutral and stable antimony compounds; these should find therapeutic and chemical-technical use.
Beispiel z ro g Natriumglykonat werden in :2o ccm lauwarmem Wasser gelöst und solange mit frisch gefälltem, noch feuchtem Antimontrihydroxyd versetzt, bis die Lösung nichts mehr aufnimmt, sondern eine starke Trübung bestehen bleibt. Die Lösung wird hierauf filtriert. Wenn man nach dem Erkalten mit viel Alkohol ausfällt, erhält man eine zähe Masse, die aber bald spröde wird, so daß sie sich leicht zerreiben läßt. Das Salz wird dann mit Alkohol gewaschen und getrocknet; Ausbeute 15 g.Example z ro g of sodium glyconate are dissolved in: 20 cc of lukewarm water and freshly precipitated, still moist antimony trihydroxide is added until the solution no longer absorbs anything, but rather a strong cloudiness persists. The solution is then filtered. If you precipitate with a lot of alcohol after cooling, you get a viscous mass, which, however, soon becomes brittle, so that it can be easily grinded. The salt is then washed with alcohol and dried; Yield 15 g.
Es stellt ein farbloses, nicht hygroskopisches Pulver dar, welches in Wasser leicht mit schwach saurer Reaktion löslich ist. Es ist unlöslich in den gebräuchlichen Lösungsmitteln. Die wässerige Lösung schmeckt fade salzig. Geringe Mengen Mineralsäure und Alkalien verändern die wässerige Lösung zunächst nicht, allmählich aber trüben sie diese und setzen unlösliche Flocken ab, rascher bei erhöhter Temperatur. Zusatz von genügend Natriumglykonat verhindert dieFällung durch Alkalien auch in der Siedehitze, nicht aber die Fällung durch Mineralsäuren. Schwefelwasserstoff fällt orange farbenes Antimonsulfid. Das Produkt enthält 3 47 °% Antimon, berechnet für C, H1.2 O, Sb Na M. G. 372,89 : 3266 % Sb.It is a colorless, non-hygroscopic powder, which is easily soluble in water with a weakly acidic reaction. It is insoluble in common solvents. The aqueous solution tastes blandly salty. Small amounts of mineral acids and alkalis do not change the aqueous solution at first, but gradually they cloud it and deposit insoluble flakes, more quickly at elevated temperature. The addition of sufficient sodium glyconate prevents precipitation by alkalis even at the boiling point, but not precipitation by mineral acids. Hydrogen sulfide falls orange-colored antimony sulfide. The product contains 3 47% antimony, calculated for C, H1.2 O, Sb, Na, MW 372.89: 3266 % Sb.
Beispiel e 3 g Natriumantimonylglykonat und 4,5 g Natriumglykonat werden in 15 ccm lauwarmem Wasser gelöst und so lange mit 2 n-Natronlauge versetzt, bis die Lösung amphoter reagiert, wozu etwas mehr als z ccm er= j forderlich ist. Die Lösung kann nun beliebig verdünnt werden und bleibt im siedenden Wasserbad stundenlang klar. Beispiel 3 In einer warmen Lösung von io g Natriumgalaktonat in "2o ccm Wasser wird aus Brechweinstein mit Schwefelsäure gefällte antimonige Säure gelöst, bis die Lösung damit gesättigt ist, was sich in einer dauernden starken Trübung kundgibt. Nach etwa i Stunde wird vom Unlöslichen durch Zentrifugieren oder Filtrieren abgetrennt und aus der klaren Lösung das Produkt abgeschieden, z. B. durch Versetzen mit ioTeilen Methylalkohol. Man erhält so 8,5 g eines farblosen lockeren Pulvers. Der Antimongehalt beträgt 33 % (Theorie: 32,66 °/a Sb). Im übrigen sind die Eigenschaften fast gleich denen des in Beispiel i beschriebenen Natriumantimonylglykonats.Example e 3 g of sodium antimonyl glyconate and 4.5 g of sodium glyconate are dissolved in 15 cc of lukewarm water and 2N sodium hydroxide solution is added until the solution reacts amphoterically, for which a little more than z cc = j is required. The solution can now be diluted as required and remains clear for hours in a boiling water bath. EXAMPLE 3 In a warm solution of 10 g sodium galactonate in 20 cc water, antimony acid precipitated from emetic tartar with sulfuric acid is dissolved until the solution is saturated with it, which manifests itself in a permanent strong turbidity. After about 1 hour the insolubles are removed by centrifugation or by filtration and separated the product from the clear solution, for example by adding 10 parts of methyl alcohol. This gives 8.5 g of a colorless, loose powder. The antimony content is 33 % (theory: 32.66 ° / a Sb) Otherwise, the properties are almost the same as those of the sodium antimonyl glyconate described in Example i.
Beispiel q.Example q.
Eine Lösung von i4,8 g lalctobionsaurem Natrium in 3o ccm Wasser wird mit Antimontrihydroxyd gesättigt, ohne zu erwärmen, bis die starke Trübung bestehen bleibt. Nach dem Klären werden durch das iofache Volumen Methylalkohol io g eines farblosen amorphen Pulvers abgeschieden. Es ist in Wasser sehr leicht löslich und hat einen Antimongehaltvon 2i,3 °/o. (Für C12H22 O14 Sb Na M. G. 535 berechnet sich der Antimongehalt auf :22,77'/,.) Im übrigen stimmen die Eigenschaften mit denen des in Beispiel i angeführten Natriumantimönylglykonats überein.A solution of 14.8 g of sodium lactobionate in 3o cc of water is used saturated with antimony trihydroxide, without heating, until the strong cloudiness persists remain. After clarification, io g of one are made up by iof the volume of methyl alcohol colorless amorphous powder deposited. It is very easily soluble in water and has an antimony content of 21.3%. (For C12H22 O14 Sb Na M.G. 535 is calculated the antimony content: 22.77 '/ ,.) Otherwise, the properties agree with those of the sodium antimönyl glyconate listed in Example i.
Analoge Verbindungen liefern die übrigen von Aldosen sich ableitenden Polyoxymonocarbonsäuren.The other compounds derived from aldoses provide analogous compounds Polyoxymonocarboxylic acids.
Claims (1)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE365818D BE365818A (en) | 1928-11-30 | ||
| DEC42300D DE573130C (en) | 1928-11-30 | 1928-11-30 | Process for the production of water-soluble antimony salts |
| US408936A US2007092A (en) | 1928-11-30 | 1929-11-21 | Manufacture of antimony compounds |
| GB35968/29A GB343898A (en) | 1928-11-30 | 1929-11-23 | Manufacture of new antimony compounds |
| CH148102D CH148102A (en) | 1928-11-30 | 1929-11-26 | Process for the preparation of a water-soluble antimony salt. |
| FR685728D FR685728A (en) | 1928-11-30 | 1929-11-28 | |
| DE1930578213D DE578213C (en) | 1928-11-30 | 1930-07-09 | Process for the production of water-soluble antimony salts |
| US547175A US2031268A (en) | 1928-11-30 | 1931-06-26 | Manufacture of new stable antimony compounds |
| GB18538/31A GB372143A (en) | 1928-11-30 | 1931-06-26 | Manufacture of new antimony compounds |
| GB18539/31A GB384687A (en) | 1928-11-30 | 1931-06-26 | Improvements in or relating to the manufacture of new stable antimony compounds |
| FR40484D FR40484E (en) | 1928-11-30 | 1931-07-07 | Process for preparing water-soluble antimony salts |
| CH155687D CH155687A (en) | 1928-11-30 | 1931-07-08 | Process for the preparation of a water-soluble antimony salt. |
| CH155686D CH155686A (en) | 1928-11-30 | 1931-07-08 | Process for the preparation of a water-soluble antimony salt. |
| CH158146D CH158146A (en) | 1928-11-30 | 1931-07-08 | Process for the preparation of a water-soluble antimony salt. |
| CH155688D CH155688A (en) | 1928-11-30 | 1931-07-08 | Process for the preparation of a water-soluble antimony salt. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC42300D DE573130C (en) | 1928-11-30 | 1928-11-30 | Process for the production of water-soluble antimony salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE573130C true DE573130C (en) | 1933-03-29 |
Family
ID=7024905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC42300D Expired DE573130C (en) | 1928-11-30 | 1928-11-30 | Process for the production of water-soluble antimony salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE573130C (en) |
-
1928
- 1928-11-30 DE DEC42300D patent/DE573130C/en not_active Expired
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