DE397458C - Process for the preparation of monoarylantimony compounds - Google Patents
Process for the preparation of monoarylantimony compoundsInfo
- Publication number
- DE397458C DE397458C DEC31417D DEC0031417D DE397458C DE 397458 C DE397458 C DE 397458C DE C31417 D DEC31417 D DE C31417D DE C0031417 D DEC0031417 D DE C0031417D DE 397458 C DE397458 C DE 397458C
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloric acid
- monoarylantimony
- compounds
- preparation
- diphenylstibine
- 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 3
- 150000001875 compounds Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- -1 diaryl stibine oxides Chemical class 0.000 description 4
- AVIGKMZINWJGRY-UHFFFAOYSA-N oxo(diphenyl)-lambda5-stibane Chemical compound C1(=CC=CC=C1)[SbH](C1=CC=CC=C1)=O AVIGKMZINWJGRY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 101100005631 Mus musculus Ccni gene Proteins 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SSXPEHBFLFUZCU-UHFFFAOYSA-M chloro(diphenyl)stibane Chemical compound C=1C=CC=CC=1[Sb](Cl)C1=CC=CC=C1 SSXPEHBFLFUZCU-UHFFFAOYSA-M 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- WQGPPBHFCXJZLP-UHFFFAOYSA-N diphenylstibane Chemical compound C=1C=CC=CC=1[SbH]C1=CC=CC=C1 WQGPPBHFCXJZLP-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JPZWFTMPXWHNRP-UHFFFAOYSA-N oxo-$l^{5}-stibane Chemical compound [SbH3]=O JPZWFTMPXWHNRP-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/92—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von monoarylantimonverbindungen. Es wurde befunden, daß man Diarylstibinoxyde in Moaioarylstibinoxyde überführen kann, indem man sie der Einwirkung saurer Medien aussetzt, wie Eisessig oder Ameisensäure oder auch alkoholischer Salzsäure. An Stelle der Diarylstibinoxyde können auch deren Derivate, wie Diarylstibinchlorüre, -äcetate usw., der Umwandlung unterworfen werden. Die Umwandlung kann schon bei gewöhnlicher Temperatur eintreten, nötigenfalls muß man erwärmen. Letzteres ist z. B. der Fall, wenn man das bei der bekannten Einwirkung von Salzsäure auf DiphenyIstibinoxyd in Eisessiglösung entstehende Diphenylstibinclilorür in die Monophenylstibinverbiiidung überführen will (siehe Beispiel 2,).Process for the preparation of monoarylantimony compounds. It was found that diarylstibine oxides can be converted into moaioarylstibine oxides by they are exposed to acidic media such as glacial acetic acid or formic acid or also alcoholic hydrochloric acid. Instead of the diaryl stibine oxides, their Derivatives such as diarylstibine chloride, acetates, etc., are subjected to the conversion. The conversion can already take place at ordinary temperature, if necessary it has to to warm up. The latter is z. B. the case if you do this with the known exposure Diphenylstibine chloride formed from hydrochloric acid on diphenylstibine oxide in glacial acetic acid solution wants to convert into the monophenylstibine compound (see Example 2,).
Beispiel i.Example i.
3- Diacetylaminodiphenylstibinoxyd werden in 3o ccni Eisessig durch Erwärmen gel<ist und die Lösung in ein Bad von 70° gebracht. Anfangs kristallisiert ein Acetat des Stibinoxyds aus, das sich aber langsam löst. Nach i- Stunde wird in Eis gekühlt und 6o cctn eisgekühlte Salzsäure 1,17 zugesetzt. Nach einiger Zeit setzt eine Kristallisation ein. Nach 12 Stunden saugt man ab, wäscht finit Salzsäure und trocknet .auf Ton. Die erhaltene Substanz ist nach dem Ergebnis der Analyse und den Eigenschaften identisch mit 1i - Acetylainiiioplienvlstiliinchlorürchlorhydrat SCH, CO - N H - C,;II4 - Sb C I.,) HCl. Dieselbe Umwandlung geht in iooprozentiger Ameisensäure schon beim Stehen vor sich. Diphenylstibinoxyd selbst ,und andere im Benzolkern stubstituierte Abkömmlinge des Diphenylstibinoxyds lassen sich der gleichen Umwandlung unterworfen. 3- Diacetylaminodiphenylstibinoxyd are gel <is in 3o ccni glacial acetic acid by heating and the solution is brought into a bath at 70 °. Initially, an acetate of stibine oxide crystallizes out, but it slowly dissolves. After 1 hour, the mixture is cooled in ice and 6o cctn of ice-cold hydrochloric acid 1.17 is added. After a while, crystallization sets in. After 12 hours, the product is filtered off with suction, washed finely with hydrochloric acid and dried on clay. According to the result of the analysis and the properties, the substance obtained is identical to 1i - Acetylainiiioplienvlstiliinchlorurchlorhydrat SCH, CO - NH - C,; II4 - Sb C I.,) HCl. The same conversion takes place in 100% formic acid when standing. Diphenylstibinoxide itself, and other derivatives of diphenylstibinoxide which are substituted in the benzene nucleus, can be subjected to the same transformation.
Beispiele. 3 g Diphenvlstibinoxyd werden in 45 ccm NIetliylalkohol und 21 ccm gesättigter alkoliolischer Salzsäure gelöst. Durch ;diese Behandlung mit Salzsäure in .der Kälte wird ,das Diphenylstibinoxyd lediglich in Diphenylstib,inchlorür übergeführt, wie das schon in ähnlicher Weise in Ann. d. Chemie, Bd. d.21, S.235 (Chem. Zentralblatt ig2i, I 138) beschrieben ist. Diese Lösung wind im KohlensätirestrOm q. biss 5 Stunden am Rückflußkühl.er gekocht, nach dem Erkalten unter Eiskühlung in verdünnter Natronlauge eingerührt. Der ausfallende flockige Niederschlag wird abgesaugt und mit Wasser und Äther gewaschen. Er enthält Phenylsti,bi@noxyd, aber noch nicht in reiner Form. Durch Behandeln mit alkalischer Wasserstoffsuperoxydlösung, worin es sich auflöst, und Wiederausfällen mit verdünnter Salzsäure läßt sich das erhaltene Produkt z. B. in Phenylstibinsäure überführen, welche in bekannter Weise über das Chlorammondoppelsalz gereinigt werden kann.Examples. 3 g of diphenyl stibine oxide are dissolved in 45 cc of methyl alcohol and 21 cc of saturated alcoholic hydrochloric acid dissolved. Through; this treatment with hydrochloric acid in the cold, the diphenylstibine oxide is only converted into diphenylstibine, inchlorur transferred, as already in a similar way in Ann. d. Chemie, Vol. D.21, p.235 (Chem. Zentralblatt ig2i, I 138) is described. This solution winds up in the coal flow q. until boiled for 5 hours on the reflux cooler, after cooling with ice cooling stirred into dilute sodium hydroxide solution. The falling out flaky precipitate will Aspirated and washed with water and ether. It contains phenylsti, bi @ noxyd, but not yet in its pure form. By treating with alkaline hydrogen peroxide solution, in which it dissolves, and reprecipitation with dilute hydrochloric acid can do that product obtained e.g. B. convert into phenylstibic acid, which in a known manner can be cleaned using the chlorammon double salt.
Auch Triplienylstibin, das unter milderen Bedingungen durch alkoholische Salzsäure in die Diphenylstibinverliindung übergeführt wird (vg1. Patent 397o79), kann ül:er die Diplienylstibinstufe hinweg bis zur --NIonoplienylantimonverbindung abgebaut werden, Wenn es der Einwirkung dieses sauren :Mittels unter den oben beschriebenen energischeren Bedingungen ausgesetzt wird.Also triplienylstibine, the milder one conditions is converted into the diphenylstibine compound by alcoholic hydrochloric acid (cf. Patent 397o79), it can go past the diplienylstibine level up to the --Nionoplienylantimony compound If there is exposure to this acidic: agent among those described above exposed to more vigorous conditions.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31417D DE397458C (en) | 1921-11-26 | 1921-11-26 | Process for the preparation of monoarylantimony compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31417D DE397458C (en) | 1921-11-26 | 1921-11-26 | Process for the preparation of monoarylantimony compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE397458C true DE397458C (en) | 1924-06-21 |
Family
ID=7019817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC31417D Expired DE397458C (en) | 1921-11-26 | 1921-11-26 | Process for the preparation of monoarylantimony compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE397458C (en) |
-
1921
- 1921-11-26 DE DEC31417D patent/DE397458C/en not_active Expired
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