CH97977A - Process for the preparation of acigarsic acid. - Google Patents
Process for the preparation of acigarsic acid.Info
- Publication number
- CH97977A CH97977A CH97977DA CH97977A CH 97977 A CH97977 A CH 97977A CH 97977D A CH97977D A CH 97977DA CH 97977 A CH97977 A CH 97977A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- arsenic
- preparation
- weight
- parts
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims description 6
- 229940000488 arsenic acid Drugs 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- HFNUUHLSQPLBQI-UHFFFAOYSA-N acetic acid;calcium Chemical compound [Ca].CC(O)=O HFNUUHLSQPLBQI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- -1 amides and Esier Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von Essigarsinsäure. Es wurde gefunden, dass man durch Um setzung von Halogenessigsäure mit arseniger Säure unter Zusatz von einem alkalisch wirk enden Mittel, zum Beispiel Alkalilauge zu der Essigarsinsäure gelangen kann.
Die neue karboxylierte Arsinsäure be sitzt wertvolle therapeutische Eigenschaften. Sie hat auf Arsen berechnet dieselbe Wirk samkeit wie die arsenige Säure.
<I>Beispiel:</I> 198 Gewichtsteilo Arsenigsäureanhydrid werden mit 830 Gewichtsteilen Natriumhy- droxyd in 700 Gewichtsteilen Wasser gelöst. In diese Lösung giesst man unter Rühren eine kalt bereitete Lösung von 273,5 Gewiclztstei- len Chloressigsäure und 130 Gewichtsteile Natriumhydroxyd iri 130 Gewichtsteilen Wasser. Sehr bald erfolgt Reaktion unter Temperaturerhöhung.
Nach ihrer Beendigung neutralisiert man mit Essigsäure, übersättigt mit Ammoniak und fällt durch Zusatz von Chlorp,alcium das essigarsinsaure Calcium aus, das man absaugt und trocknet. 120 Gewichtsteile des so gewonnenen Kalksalzes werden in 1500 Gewichtsteilen n-Schwefelsäure im Wasserbade erwärmt, heiss vom Calciumsulfat abgesaugt und das Filtrat im Vakuum bei 70 bis 80 zur Trockne verdampft. Der Rückstand wird in Aceton aufgenommen, scharf abgesaugt und die rohe Essigarsinsäure an der Luft getrocknet.
Eine weitere Menge lässt sich aus dem Filtrat durch Abdestillieren des Acetons und Abpressen des langsam kristallisierenden Rückstandes ge winnen. Die rohe Säure wird dann zur Tren nung von anorganischen Beimengungen in 5 Gewichtsteilen heissem Alkohol gelöst, so fort allgekühlt, filtriert und das Filtrat im Vakuum bei 50-60 bis auf einen kleinen Rest erbdestilliert. Beim Versetzen des Rück standes mit Benzol entsteht eine ölige, schnell erstarrende Fällung, die abgesaugt und mit etwas Aceton nachgewachen wird.
Durch Um kristallisieren aus 10 Gewichtsteilen Eisessig gewinnt man die Essigarsinsäure in harten, farblosen Kristallen, die bei 152 schmelzen. An Stelle von Chloressigsäure kann na türlich auch Bromessigsäure oder Derivate solcher Säuren, wie Amide und Esier ver wendet werden. An Stelle der arsenigcn Säure können ihre Derivate und 'Salze benutzt wer den.
In allen Fällen entsteht bei der Reaktion intermediär Halogensäure resp. arsenige Säure.
Process for the preparation of acigarsic acid. It has been found that the acetic acid can be obtained by reacting haloacetic acid with arsenic acid with the addition of an alkaline agent, for example alkali lye.
The new carboxylated arsic acid has valuable therapeutic properties. Calculated on arsenic, it has the same potency as arsenic acid.
<I> Example: </I> 198 parts by weight of arsenic anhydride are dissolved with 830 parts by weight of sodium hydroxide in 700 parts by weight of water. A cold solution of 273.5 parts by weight of chloroacetic acid and 130 parts by weight of sodium hydroxide in 130 parts by weight of water is poured into this solution with stirring. A reaction with an increase in temperature takes place very soon.
When this has ended, it is neutralized with acetic acid, supersaturated with ammonia, and the acetic acid calcium is precipitated by adding chlorine and alcium, which is filtered off and dried. 120 parts by weight of the lime salt obtained in this way are heated in 1500 parts by weight of n-sulfuric acid in a water bath, the calcium sulfate is suctioned off while hot and the filtrate is evaporated to dryness in vacuo at 70 to 80. The residue is taken up in acetone, sharply suctioned off and the crude acetic arsenic is dried in the air.
A further amount can be obtained from the filtrate by distilling off the acetone and pressing off the slowly crystallizing residue. The crude acid is then dissolved in 5 parts by weight of hot alcohol to separate inorganic impurities, immediately cooled and filtered and the filtrate is earth-distilled in vacuo at 50-60 with the exception of a small residue. When benzene is added to the residue, an oily, rapidly solidifying precipitate is formed, which is filtered off with suction and waxed up with a little acetone.
By crystallizing from 10 parts by weight of glacial acetic acid, the acetic arsic acid is obtained in hard, colorless crystals which melt at 152. Instead of chloroacetic acid, bromoacetic acid or derivatives of such acids, such as amides and Esier, can of course also be used. In place of arsenic acid its derivatives and salts can be used.
In all cases, the reaction produces intermediate halogen acid, respectively. arsenic acid.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE97977X | 1920-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH97977A true CH97977A (en) | 1923-02-16 |
Family
ID=5646590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH97977D CH97977A (en) | 1920-10-18 | 1921-09-20 | Process for the preparation of acigarsic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH97977A (en) |
-
1921
- 1921-09-20 CH CH97977D patent/CH97977A/en unknown
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