DE279254C - - Google Patents
Info
- Publication number
- DE279254C DE279254C DENDAT279254D DE279254DA DE279254C DE 279254 C DE279254 C DE 279254C DE NDAT279254 D DENDAT279254 D DE NDAT279254D DE 279254D A DE279254D A DE 279254DA DE 279254 C DE279254 C DE 279254C
- Authority
- DE
- Germany
- Prior art keywords
- arsenic acid
- arsenic
- inositol
- salts
- water
- 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.)
- Active
Links
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical class O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims description 16
- 229940000488 arsenic acid Drugs 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 7
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 6
- 229960000367 inositol Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 5
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229930195725 Mannitol Natural products 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 239000000594 mannitol Substances 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 2
- 229940000489 arsenate Drugs 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- -1 arsenic acid compound Chemical class 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000005639 glycero group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GIYFBMOEQXSGJH-UHFFFAOYSA-N [As](O)(O)(O)=O.[Mo] Chemical compound [As](O)(O)(O)=O.[Mo] GIYFBMOEQXSGJH-UHFFFAOYSA-N 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004001 inositols Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 230000004580 weight loss 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/72—Aliphatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß man Arsensäureverbindungen der höheren, mehrwertigen Alkohole, welche zum Teil das Arsen in sehr fester Bindung enthalten, in einfacher Weise dadurch gewinnen kann, daß man höhere, mehrwertige Alkohole oder ihre Ester mit Arsensäure oder Arsensäureanhydrid im Vakuum auf höhere Temperatur erhitzt.It has been found that arsenic acid compounds of the higher, polyhydric alcohols, some of which contain the arsenic in a very tight bond, can be obtained in a simple manner by using higher, polyhydric alcohols or their esters with arsenic acid or arsenic anhydride in a vacuum heated to a higher temperature.
Arsensäure Verbindungen von höheren, mehr-·Arsenic acid compounds of higher, more
ίο wertigen Alkoholen und deren Salzen sind bis jetzt noch nicht bekannt.ίο valuable alcohols and their salts are up not yet known.
P ag el (Journ. pharm. chim. [6], 13, S. 449; Zentralblatt 1901/I. S. 1383) hat durch mehrtägiges Erhitzen von Glycerin mit Arsensäure und Neutralisieren der Flüssigkeit mit Kalk ein Calciumglyceroarseniat erhalten. Auger (Compt. rend. 134, S. 238; Zentralblatt 1902, I. S. 522) war es nicht möglich, das von P ag el (1. c.) beschriebene Salz herzustellen, da durch Wasser sofort Hydrolyse eintrat. Dieser Umstand einerseits sowie die Feststellungen von Lang, Makay und Gortner (Proc. 24, 150; Zentralblatt 1908, II. S. 849), welche fanden, daß sich Ester der arsenigen Säure beim Kochen von As2O3 mit Alkohole'n nur in sehr geringer Menge bilden, da sie durch das gebildete Wasser sehr schnell wieder zersetzt werden, ließen es nicht erwarten, daß die Ester der höheren, mehrwertigen Alkohole, wie z. B. des Mannits und des Inosits, mit Arsensäure nach dem vorliegenden Verfahren glatt und in guter Ausbeute entstehen würden. Außerdem war auch nicht vorauszusehen, daß es möglich sein werde, Salze der Arsensäureverbindungen von höheren, mehrwertigen Alkoholen herzustellen, da ja schon die niederen Glieder als sehr leicht hydrolytisch spaltbar bekannt waren.P ag el (Journ. Pharm. Chim. [6], 13, p. 449; Zentralblatt 1901 / IS 1383) obtained a calcium glycero arsenate by heating glycerine with arsenic acid for several days and neutralizing the liquid with lime. Auger (Compt. Rend. 134, p. 238; Zentralblatt 1902, IS 522) it was not possible to produce the salt described by P ag el (1. c.), Since hydrolysis occurred immediately with water. This fact on the one hand as well as the findings of Lang, Makay and Gortner (Proc. 24, 150; Zentralblatt 1908, II. P. 849), who found that esters of arsenic acid are only formed when As 2 O 3 is boiled with alcohols form in very small amounts, since they are very quickly decomposed again by the water formed, it was not to be expected that the esters of the higher, polyhydric alcohols, such as. B. of mannitol and inositol, with arsenic acid according to the present process would arise smoothly and in good yield. In addition, it was not foreseeable that it would be possible to produce salts of the arsenic acid compounds of higher, polyhydric alcohols, since the lower members were already known to be very easily hydrolytically cleavable.
Von dem weiter bekannten Verfahren zur Herstellung von Glyceroarseniat (Pi et et und Bon, Zentralblatt 1906, I. S. 21) unterscheidet sich das vorliegende Verfahren durch größere Einfachheit. Dort wird nämlich zunächst Arsentrioxyd durch fraktionierte Destillation in Arsenessigsäureanhydrid übergeführt und diese Verbindung mit Glycerin erhitzt.From the further known process for the production of glycero arsenate (Pi et et and Bon, Zentralblatt 1906, I. p. 21) the present method differs by greater simplicity. There arsenic trioxide is first produced by fractional distillation converted into arsenic anhydride and heated this compound with glycerine.
Die Arsensäureverbindungen der mehrwertigen Alkohole sollen therapeutische Verwendung finden.The arsenic acid compounds of the polyhydric alcohols are said to have therapeutic use Find.
120 Teile Mannit werden mit 78 Teilen Arsensäure gemischt, etwas angefeuchtet und während 24 Stunden bei 30 mm Hg auf 140 bis 145 ° erhitzt. Das Reaktionsprodukt wird mit Wasser und 20 Teilen Magnesiumoxyd geschüttelt. Hernach wird die Lösung abfütriert und mit absolutem Alkohol versetzt. Die Arsensäureverbindung des Mannits fällt dann als weißes Pulver aus. Die Substanz enthält 14,44 Prozent Arsen, währenddem die Theorie für die Verbindung: [Mannit-As O2] 2 Mg 15,5 Prozent As erfordert.120 parts of mannitol are mixed with 78 parts of arsenic acid, slightly moistened and heated to 140 to 145 ° for 24 hours at 30 mm Hg. The reaction product is shaken with water and 20 parts of magnesium oxide. The solution is then filtered off and absolute alcohol is added. The arsenic acid compound of mannitol then precipitates as a white powder. The substance contains 14.44 percent arsenic, while the theory for the compound: [Mannitol As O 2 ] 2 Mg requires 15.5 percent As.
Gleiche Teile von Inosit und Arsensäure werden im Vakuum bei einer Temperatur von
über 2öo° während 12 Stunden zusammengeschmolzen.
Nach der' Beendigung der Reaktion wird das Produkt mit Wasser und
,Magnesiumoxyd geschüttelt und das Magne-/siumsalz
der Arsensäure verbindung des Inosits ίο' mit 'Alkohol gefällt. Zur Entfernung von
/ eventuell unverändertem Inosit wird die Fäl- _;' lung nochmals in Wasser gelöst, abermals mit
Alkohol gefällt und dann noch mit 8oprozentigem Alkohol ausgekocht.
Das auf diese Weise erhaltene Magnesium-,· salz einer Inositarsensäure stellt ein weißes
'' amorphes, in Wasser lösliches Pulver dar, welches mit Ammonmolybdat bei Gegenwart von
starker Salpetersäure auch nach mehrstündigem Erhitzen auf dem Wasserbade keine Molybdänarsensäure
abscheidet.Equal parts of inositol and arsenic acid are melted together in a vacuum at a temperature of over 20 ° for 12 hours. After the end of the reaction, the product is shaken with water and magnesium oxide and the magnesium / sium salt of the arsenic acid compound of the inositol is precipitated with alcohol. To remove / possibly unaltered inositol, the Fäl- _; ' Dissolved again in water, precipitated again with alcohol and then boiled with 8% alcohol.
The magnesium salt of an inositol arsenic acid obtained in this way is a white, amorphous, water-soluble powder which, with ammonium molybdate, does not deposit any molybdenum arsenic acid in the presence of strong nitric acid, even after several hours of heating in the water bath.
Aus dem Magnesiumsalz kann man in üblicher Weise die übrigen Salze dieser Inositarsensäure darstellen.The remaining salts of this inositol arsenic acid can be obtained from the magnesium salt in the usual way represent.
TI · · !TI · ·!
265 Teile Inosithexacetat vom Schmelzpunkt 211 ° werden mit 150 g Arsensäure auf dem Wasserbade so lange erwärmt, bis die Mischung sich verflüssigt hat. Hierauf wird dieselbe im Vakuum auf 140 bis 200° erhitzt. Wenn keine Gewichtsabnahme mehr stattfindet, so wird die Reaktionsmasse in gleicher Weise aufgearbeitet, wie im Beispiel 2 angegeben. Man erhält ebenfalls das Magnesiumsalz einer Inositarsensäure.265 parts of inositol hexacetate with a melting point of 211 ° are mixed with 150 g of arsenic acid Heat the water bath until the mixture has liquefied. Then it becomes the same heated in vacuo to 140 to 200 °. If there is no more weight loss, the reaction mass is worked up in the same way as indicated in Example 2. The magnesium salt of an inositol arsenic acid is also obtained.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE279254C true DE279254C (en) |
Family
ID=535186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT279254D Active DE279254C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE279254C (en) |
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0
- DE DENDAT279254D patent/DE279254C/de active Active
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