DE372461C - Process for the production of basic aluminum compounds of santonin - Google Patents
Process for the production of basic aluminum compounds of santoninInfo
- Publication number
- DE372461C DE372461C DEK80484D DEK0080484D DE372461C DE 372461 C DE372461 C DE 372461C DE K80484 D DEK80484 D DE K80484D DE K0080484 D DEK0080484 D DE K0080484D DE 372461 C DE372461 C DE 372461C
- Authority
- DE
- Germany
- Prior art keywords
- santonin
- production
- aluminum compounds
- basic aluminum
- aluminum
- 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
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 title claims description 8
- TUFPZQHDPZYIEX-UHFFFAOYSA-N alpha-Santonin Natural products C1CC2(C)C=CC(=O)C=C2C2C1C(C)C(=O)O2 TUFPZQHDPZYIEX-UHFFFAOYSA-N 0.000 title claims description 6
- XJHDMGJURBVLLE-BOCCBSBMSA-N alpha-santonin Chemical compound C([C@]1(C)CC2)=CC(=O)C(C)=C1[C@@H]1[C@@H]2[C@H](C)C(=O)O1 XJHDMGJURBVLLE-BOCCBSBMSA-N 0.000 title claims description 6
- 229940074353 santonin Drugs 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UNPYYTKZOHYHMZ-DQMQVFGMSA-N (2S)-2-[(1S,2S,5S,6R,8R)-1,5-dimethyl-4,7-dioxo-8-tricyclo[4.4.0.02,8]decanyl]propanoic acid Chemical class C1C(=O)[C@@H](C)[C@H]2C(=O)[C@@]3([C@@H](C(O)=O)C)[C@@H]1[C@]2(C)CC3 UNPYYTKZOHYHMZ-DQMQVFGMSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung basischer Aluminiumverbindungen des Santonins. Die moderne therapeutisch-chemische Forschung hat gezeigt, daß Aluminiumverbindungen für die therapeutische Darreichung besonders wertvoll sind. Infolgedessen verdienen auch die Aluminiumsalze des Santonins, das wohl das wichtigste Anthelmintikum unseres Arzneimittelschatzes vorstellt, besondere Beachtung.Process for the production of basic aluminum compounds of santonin. Modern therapeutic-chemical research has shown that aluminum compounds are particularly valuable for therapeutic administration. As a result, earn also the aluminum salts of santonin, probably the most important anthelmintic of ours Medicinal treasure presents, special attention.
In Gmelin-Kraut, Handbuch der organischen Chemie 1866, Seite 1181, ist eine von T r o m m s d o r f stammende Beobachtung wiedergegeben, wonach Natriumsantoninat in einer Lösung von Aluminiumsulfat »weiße Flocken« erzeugt, die in Alkohol löslich sind. Eine nähere Beschreibung dieser Fällung, Analysen usw. finden sie nicht.In Gmelin-Kraut, Handbook of Organic Chemistry 1866, page 1181, an observation from T r o m m s d o r f is given, according to which sodium toninate in a solution of aluminum sulphate produces "white flakes" which are soluble in alcohol are. They do not find a more detailed description of this precipitation, analyzes, etc.
Gegenstand vorliegenden Patentanspruches ist nun ein Verfahren zur Herstellung basischer Aluminiumverbindungen des Santonins, die dadurch erzeugt werden, daß heiße Lösungen von Aluminiumsalzen und santoninsauren Salzen bei gewöhnlichem oder erhöhtem Druck zusammengegeben werden. Auf diese Weise entstehen dichte, weiße Niederschläge, die nach dem Filtrieren und Trocknen als weißes,-feines Pulver gewonnen werden. Dasselbe ist in Alkohol unlöslnch, daher muß es als bisher unbekannt angesprochen werden.The subject of the present claim is now a method for Production of basic aluminum compounds of santonin, which are produced by that hot solutions of aluminum salts and santonic acid salts with ordinary or increased pressure. This creates dense, white ones Precipitates obtained after filtering and drying as a white, fine powder will. It is insoluble in alcohol, so it must be addressed as previously unknown will.
Die dem Entstehen dieser Fällungen zugrunde liegenden chemischen-Reaktionen sind leicht verständlich. Aluminiumhydroxyd ist eine schwache Base, Santoninsäure eine schwache Säure. Salze aus diesen Komponenten werden also in hohem Maße der hydrolytischen Spaltung unterworfen sein. Je höher die Temperatur der Lösungen ist und je länger die Fällungen mit Wasser in Berührung sind, je weiter wird .die Hydrolyse fortschreiten. Es ist gelungen, durch geeignete Versuchsanordnung eine stufenweise Hydrolyse mit ziemlicher Genauigkeit zu verfolgen, j,e nachdem ein Molekül oder mehrere Moleküle Wasser an der Reaktion beteiligt sind. Aus den Analysen kann bei verschiedenen Fällungen auf folgende Zusammensetzung geschlossen werden: A1 (O H) (C15 H13 04)z und AL (0 H). (C15 H13 O4)s.The chemical reactions underlying the formation of these precipitations are easy to understand. Aluminum hydroxide is a weak base, santonic acid is a weak acid. Salts from these components will therefore be subject to hydrolytic cleavage to a high degree. The higher the temperature of the solutions and the longer the precipitates are in contact with water, the further the hydrolysis will proceed. It has been possible to follow a step-by-step hydrolysis with reasonable accuracy by means of a suitable experimental set-up, j, e after one or more molecules of water are involved in the reaction. The following composition can be concluded from the analyzes for various precipitations: A1 (OH) (C15 H13 04) z and AL (0 H). (C15 H13 O4) s.
Es sind naturgemäß aber auch alle Zwischenstufen und auch weiter hydrolytisch gespaltene Produkte möglich. Die Verhältnisse sind analog denjenigen, die bei der basisch essigsauren Tonerde :beobachtet worden sind.Naturally, however, all intermediate stages and also further are hydrolytic split products possible. The conditions are analogous to those in the basic acetic clay: have been observed.
Auch durch Arbeiten unter Druck lassen sich die beschriebenen Produkte herstellen. -Die Herstellung geschieht beispielsweise auf folgende Art: 2o Teile kristallisiertes, reines Natriumsa;ntoninat werden in zoo Teilen Wasser von Siedetemperatur gelöst und dazu wird eine heiße Lösung von 6,¢ Teilen Aluminiumsulfat in 5o Teilen Wasser gegeben. Der sich sofort abscheidende. voluminöse Brei wird abgenutscht und mit heißem Wasser gewaschen. Aus dem Filtrat kann die bei der Bildung der basischen Salze entstehende freie Santoninsäure wiedergewonnen werden. Das abgesaugte Produkt wird nach dem Trocknen und Pulverisieren zur Entfernung der letzten Reste anhaftender freier Santoninsäure mit Chloroform gewaschen.The products described can also be achieved by working under pressure produce. -The production is done, for example, in the following way: 2o parts Crystallized, pure sodium santoninate are dissolved in zoo parts of water at the boiling point dissolved and a hot solution of 6.0 parts of aluminum sulfate in 50 parts Given water. The immediately separating one. voluminous pulp is sucked off and washed with hot water. From the filtrate can those in education the free santonic acid formed from the basic salts can be recovered. The sucked off Product is dried and pulverized to remove the last residue adhering free santoninic acid washed with chloroform.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK80484D DE372461C (en) | 1922-01-12 | 1922-01-12 | Process for the production of basic aluminum compounds of santonin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK80484D DE372461C (en) | 1922-01-12 | 1922-01-12 | Process for the production of basic aluminum compounds of santonin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE372461C true DE372461C (en) | 1923-03-28 |
Family
ID=7233887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK80484D Expired DE372461C (en) | 1922-01-12 | 1922-01-12 | Process for the production of basic aluminum compounds of santonin |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE372461C (en) |
-
1922
- 1922-01-12 DE DEK80484D patent/DE372461C/en not_active Expired
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