DE223796C - - Google Patents
Info
- Publication number
- DE223796C DE223796C DENDAT223796D DE223796DC DE223796C DE 223796 C DE223796 C DE 223796C DE NDAT223796 D DENDAT223796 D DE NDAT223796D DE 223796D C DE223796D C DE 223796DC DE 223796 C DE223796 C DE 223796C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- acids
- oxyarylarsinic
- diazotized
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940000488 arsenic acid Drugs 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YKQNYRADBBHWOK-UHFFFAOYSA-N phenylarsonamidic acid Chemical compound N[As](O)(=O)C1=CC=CC=C1 YKQNYRADBBHWOK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution 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
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 223796 -KLASSE 12 #. GRUPPE - JVl 223796 - CLASS 12 #. GROUP
Verfahren zur Darstellung von Oxyarylarsinsäuren.Process for the preparation of oxyarylarsinic acids.
Zusatz zum Patente 205616 vom 7. August 1907.Addendum to patent 205616 of August 7, 1907.
Patentiert im Deutschen Reiche vom 7. August 1907 ab. Längste Dauer: 6. August 1922. Patented in the German Empire on August 7 , 1907 . Longest duration: August 6 , 1922.
Es wurde gefunden, daß man die für medizinische Zwecke wertvollen Oxyarylarsinsäuren, deren Herstellen durch Erhitzen von Phenolen mit Arsensäure durch das Hauptpatent geschützt ist, auch in der Weise herstellen kann, daß man diazotierte Aminophenylarsinsäure und deren Homologen in wäßriger Lösung zersetzt.It has been found that oxyarylarsinic acids, which are valuable for medical purposes, their manufacture by heating phenols with arsenic acid by the main patent is protected, can also be prepared in such a way that diazotized aminophenylarsinic acid and their homologues decomposed in aqueous solution.
■ Beispiel:■ Example:
217 Gewichtsteile ρ -.Aminophenylarsinsäure werden in 4000 Teilen 5 prozentiger Schwefelsäure gelöst und mit 74 Teilen Natriumnitrit diazotiert. Die Diazolösung wird auf dem Dampfbade erwärmt, bis die Stickstoffentwicklung beendet ist. Um das gebildete Phenolderivat zu isolieren, kann man die Schwefelsäure mit Barytwasser ausfällen und die filtrierte Flüssigkeit im Vakuum zur Trockne dampfen. Das Natriumsalz der p-Oxyphenylarsinsäure bleibt als schwach gelbliche Kristallmasse zurück; es läßt sich durch Umkristallisieren aus verdünntem Alkohol rein gewinnen. Durch Eindampfen des Natriumsalzes mit berechneter Menge Schwefelsäure, am besten im Vakuum, und Extraktion des Rückstands mit Aceton erhält man nach dem Verdampfen des letzteren die freie Oxyphenylarsinsäure als in Wasser leicht lösliches, schwach gelbliches, bald erstarrendes öl.217 parts by weight of ρ-aminophenylarsinic acid are dissolved in 4000 parts of 5 percent sulfuric acid and 74 parts of sodium nitrite diazotized. The diazo solution is heated on the steam bath until the evolution of nitrogen is finished. Sulfuric acid can be used to isolate the phenol derivative formed precipitate with barite water and the filtered liquid to dryness in a vacuum steam. The sodium salt of p-oxyphenylarsinic acid remains as a pale yellowish crystal mass return; it can be obtained in pure form by recrystallization from dilute alcohol. By evaporating the sodium salt with the calculated amount of sulfuric acid, preferably im Vacuum, and extraction of the residue with acetone is obtained after evaporation of the the latter the free oxyphenylarsinic acid as easily soluble in water, slightly yellowish, soon solidifying oil.
Durch Kristallisation aus Eisessig gewinnt man die Oxyphenylarsinsäure in kleinen gelblichen Prismen, die bei 173 bis 174 ° unter Zersetzung schmelzen. Sie ist leicht löslich in kaltem Wasser, Alkohol, Aceton und verdünnten Mineralsäuren, in Äther und Essigester dagegen schwer löslich. Die Alkalisalze sind in Wasser leicht löslich und kristallisieren aus verdünntem Alkohol in Nadeln.By crystallizing from glacial acetic acid, the oxyphenylarsinic acid is obtained in small, yellowish forms Prisms that melt at 173 to 174 ° with decomposition. It is easily soluble in cold water, alcohol, acetone and dilute mineral acids, in ether and ethyl acetate on the other hand hardly soluble. The alkali salts are easily soluble in water and crystallize from diluted alcohol in needles.
In analoger Weise werden aus anderen Aminoarylarsinsäuren die entsprechenden Oxyarylarsinsäuren erhalten.In an analogous manner, other aminoarylarsinic acids are converted into the corresponding oxyarylarsinic acids obtain.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE223796T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE223796C true DE223796C (en) | 1910-07-02 |
Family
ID=5852444
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT205616D Expired DE205616C (en) | |||
| DENDAT223796D Expired DE223796C (en) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT205616D Expired DE205616C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE223796C (en) |
-
0
- DE DENDAT205616D patent/DE205616C/de not_active Expired
- DE DENDAT223796D patent/DE223796C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE205616C (en) | 1900-01-01 |
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