DE261825C - - Google Patents
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- Publication number
- DE261825C DE261825C DENDAT261825D DE261825DA DE261825C DE 261825 C DE261825 C DE 261825C DE NDAT261825 D DENDAT261825 D DE NDAT261825D DE 261825D A DE261825D A DE 261825DA DE 261825 C DE261825 C DE 261825C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- antimony
- aromatic
- solution
- hydrochloric acid
- 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.)
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- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052787 antimony Inorganic materials 0.000 claims description 5
- -1 antimony halides Chemical class 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical class [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- JLBJQENXXWFDPO-UHFFFAOYSA-N ClC1=CC=C(C=C1)[SbH2] Chemical compound ClC1=CC=C(C=C1)[SbH2] JLBJQENXXWFDPO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- BYPJMNINGIGYTF-UHFFFAOYSA-K [N-]=[N+]=[Sb](O)(O)O Chemical class [N-]=[N+]=[Sb](O)(O)O BYPJMNINGIGYTF-UHFFFAOYSA-K 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-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
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- Ja 261825 — KLASSE 12 o. GRUPPE- Yes 261825 - CLASS 12 or GROUP
CHEMISCHE FABRIK von HEYDEN AKT-GES. in RADEBEUL b. DRESDEN.CHEMICAL FACTORY by HEYDEN AKT-GES. in RADEBEUL b. DRESDEN.
Verfahren zur Darstellung von aromatischen Stibinsäuren. Zusatz zum Patent 254421.Process for the preparation of aromatic stibic acids. Addition to patent 254421.
Patentiert im Deutschen Reiche vom 6. August 1912 ab. Längste Dauer: 2. August 1926.Patented in the German Empire on August 6, 1912. Longest duration: August 2, 1926.
Nach dem Verfahren des Patents 254421 werden primäre aromatische Stibinsäuren hergestellt durch Umsetzung von Diazoverbindungen aromatischer Amine mit antimoniger Säure und Abspaltung des Diazostickstoffs aus den intermediär entstandenen Diazoantimoniten. Primary aromatic stibic acids are produced by the process of patent 254421 by reacting diazo compounds of aromatic amines with antimony acid and splitting off the diazo nitrogen the intermediate diazoantimonites.
Je nach der Natur der Aminoverbindung kann man die Arbeitsweise mannigfach variieren, und bei weiterer Bearbeitung hat sich herausgestellt, daß man auch die Reihenfolge der einzelnen Operationen abändern kann. Man kann z. B. das Antimon in Form von Antimontrichlorid zu der Lösung des zu diazotierenden Amins hinzugeben, wodurch die Möglichkeit der Bildung einer Doppelverbindung aus Amin und Antimonchlorid gegeben ist (vgl. z. B. Journal of the Chemical Society, Transactions 1911, S. 1382—86, Percy May, »The action of the chlorides of antimony on aniline and its derivatives«), hierauf wie üblich diazotieren und dann mit Alkalilauge umsetzen ; oder man kann auch der Lösung des diazotierten Amins Antimontrichlorid zusetzen, wodurch nach den Angaben des Journal of the Chemical Society, Transactions 1912, S. 1037—4°> Percy May, »Compounds of antimony trichloride with diazonium chlorides« Doppelverbindungen aus Antimontrichlorid und Diazoniumchlorid gebildet werden, die man dann mit Alkalilauge zersetzt. Diese Doppelverbindung zu isolieren ist nicht nötig, man kann sie in vielen Fällen vorteilhaft bei Gegenwart ihrer Mutterlauge zersetzen. Percy May hat bereits solche Doppelverbindungen aus Diazoniumehloriden und Antimontrichlorid mit Wasser zersetzt und z. B. aus Benzoldiazoniumchlorid-Antimontrichlorid Phenol und Diphenyl erhalten.Depending on the nature of the amino compound, the mode of operation can be varied in many ways, and with further processing it turned out that you can also change the order of the individual operations can change. You can z. B. the antimony in the form of antimony trichloride to the solution to be diazotized Add amine, whereby the possibility of the formation of a double compound from amine and antimony chloride is given (see e.g. Journal of the Chemical Society, Transactions 1911, pp. 1382-86, Percy May, "The action of the chlorides of antimony on aniline and its derivatives"), then as usual diazotize and then react with alkali lye; or you can also solve the add diazotized amine antimony trichloride, which according to the Journal of the Chemical Society, Transactions 1912, pp. 1037-4 °> Percy May, "Compounds of antimony trichloride with diazonium chlorides" Double compounds of antimony trichloride and diazonium chloride are formed, which are then decomposed with alkali. These It is not necessary to isolate the double compound; in many cases it can be used to advantage Decompose the presence of their mother liquor. Percy May already has such double connections decomposed from diazonium chloride and antimony trichloride with water and z. B. from benzene diazonium chloride-antimony trichloride Obtained phenol and diphenyl.
Das Wesentliche bei dem vorliegenden allgemeinen Verfahren zur Darstellung von aromatischen Stibinsäuren ist in jedem Falle die Ausführung der Endoperation, die Abspaltung des Stickstoffs, bei Gegenwart von Alkali.The essence of the present general method for the preparation of aromatic In any case, stibic acids are the execution of the final operation, the splitting off of nitrogen, in the presence of alkali.
45 Beispiel 1.45 Example 1.
Darstellung von p-Chlorphenylstibin-Representation of p-chlorophenylstibine
säure.acid.
50 Teile Parachloranilin werden in 250 Teilen Salzsäure (spez. Gew. 1,123) und 150 Teilen Wasser gelöst und mit der Lösung von 29 Teilen Natriumnitrit wie üblich diazotiert. Andererseits werden 84 Teile Antimontrichlorid in 110 Teilen Salzsäure (spez. Gew. 1,123) und 50 Teilen Wasser gelöst und zu der Diazolösung zufließen gelassen. Es entsteht ein dicker, gelblicher Niederschlag, der abgesaugt, mit etwas verdünnter Salzsäure gewaschen und50 parts of parachloroaniline are dissolved in 250 parts of hydrochloric acid (specific weight 1.123) and 150 parts of water and diazotized as usual with the solution of 29 parts of sodium nitrite. On the other hand, 84 parts of antimony trichloride are dissolved in 110 parts of hydrochloric acid (specific weight 1.123) and 50 parts of water and allowed to flow into the diazo solution. A thick, yellowish precipitate is formed, which is filtered off with suction, washed with a little dilute hydrochloric acid and
in 1500 Teile Wasser eingerührt wird; hierzu läßt man i5oTeile Natronlauge (spez. Gew. 1,47) zufließen. Die Stickstoffentwicklung setzt dann langsam ein in dem Maße, wie die Doppelverbindung durch das Alkali zerlegt wird. Nach Beendigung derselben wird filtriert, der Rückstand mit verdünnter warmer Natronlauge nochmals ausgezogen und die vereinigten Filtrate mit Salzsäure gefällt. Die ausgefällte p-Chlorphenylstibinsäure wird abgesaugt und getrocknet in 110 Teilen Salzsäure (spez. Gew. 1,123) durch Erwärmen in Lösung gebracht. Die Lösung wird nach Zusatz von etwas Tierkohle filtriert und mit festem Salmiak bis zur Sättigung versetzt, zur Abscheidung des Oxychloride. Nach mehrstündigem Stehen wird abgesaugt, und durch Waschen mit an Salmiak gesättigter Salzsäure (spez. Gew. 1,123) werden die anorganischen Antimonverbindungen entfernt. Der Rückstand wird dann mit verdünnter Natronlauge zersetzt, die alkalische Lösung filtriert und mit verdünnter Salzsäure die reine p-Chlorphenylstibinsäure als weißer Niederschlag ausgefällt. Nach dem Trocknen stellt sie ein farbloses Pulver dar, welches aus einer Lösung in Alkohol, dem Benzol, Chloroform oder Schwefelkohlenstoff zugesetzt ist, in kristallisiertem Zustande erhältlich ist. Beim Erhitzen zersetzt sie sich, ohne vorher zu schmelzen.is stirred into 1500 parts of water; for this purpose, i5o parts of sodium hydroxide solution (specific weight 1.47) flow in. The evolution of nitrogen then begins slowly to the same extent as the double compound is decomposed by the alkali. When this is complete, it is filtered and the residue with dilute warm sodium hydroxide solution extracted again and the combined filtrates precipitated with hydrochloric acid. The precipitated one p-Chlorophenylstibic acid is filtered off with suction and dried in 110 parts of hydrochloric acid (spec. 1.123) brought into solution by heating. The solution becomes after adding some animal charcoal filtered and mixed with solid ammonia to saturation to separate the oxychloride. After standing for several hours, the mixture is filtered off with suction and washed with hydrochloric acid saturated with salmiac (specific weight 1.123) removes the inorganic antimony compounds. The residue is then diluted with Caustic soda decomposes, the alkaline solution filtered and diluted with hydrochloric acid the pure p-chlorophenylstibic acid precipitated as a white precipitate. After drying it is a colorless powder, which is made from a solution in alcohol, benzene, Chloroform or carbon disulfide is added, is available in crystallized state. When heated, it decomposes without melting first.
93 Teile Anilin werden zusammen mit 220 Teilen Antimonchlorür in 850 Teile Salzsäure (vom spez. Gew. 1,123) und 1000 Teile Wasser eingetragen und nach einigem Rühren in bekannter Weise mit 71 Teilen Natriumnitrit diazotiert. Nach beendeter Diazotierung läßt man unter Kühlung langsam eine Lösung von 400 Teilen Ätznatron in 10000 Teilen Wasser zufließen, während das Rühren fortgesetzt wird. Nach kurzer Zeit tritt lebhafte Stickstoffentwicklung ein, und es bildet sich Phenylstibinsäure, die nach der im Hauptpatent 254421, Beispiel 1, beschriebenen Weise aus der Reaktionsflüssigkeit gewonnen und gereinigt wird.93 parts of aniline are combined with 220 parts of antimony chloride in 850 parts of hydrochloric acid (from spec. Weight 1.123) and 1000 parts of water entered and after some stirring, diazotized in a known manner with 71 parts of sodium nitrite. After the end of the diazotization, a solution of 400 parts of caustic soda in 10,000 parts of water is slowly left with cooling flow in while stirring is continued. After a short time there is vigorous evolution of nitrogen one, and phenylstibic acid is formed, which according to the one in the main patent 254421, Example 1, described manner the reaction liquid is recovered and purified.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE191216350X | 1911-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE261825C true DE261825C (en) |
Family
ID=32337255
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT296940D Active DE296940C (en) | 1911-08-02 | ||
| DENDAT254421D Active DE254421C (en) | 1911-08-02 | ||
| DENDAT261825D Active DE261825C (en) | 1911-08-02 | ||
| DENDAT269205D Active DE269205C (en) | 1911-08-02 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT296940D Active DE296940C (en) | 1911-08-02 | ||
| DENDAT254421D Active DE254421C (en) | 1911-08-02 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT269205D Active DE269205C (en) | 1911-08-02 |
Country Status (2)
| Country | Link |
|---|---|
| DE (4) | DE269205C (en) |
| GB (1) | GB191216350A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL61894C (en) * | 1946-06-14 | |||
| FR2444043A1 (en) * | 1978-12-15 | 1980-07-11 | Bottu | NEW PARACETAMOL DERIVATIVE, PREPARATION METHOD THEREOF AND THERAPEUTIC USE THEREOF |
-
0
- DE DENDAT296940D patent/DE296940C/de active Active
- DE DENDAT254421D patent/DE254421C/de active Active
- DE DENDAT261825D patent/DE261825C/de active Active
- DE DENDAT269205D patent/DE269205C/de active Active
-
1912
- 1912-07-12 GB GB191216350D patent/GB191216350A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE254421C (en) | |
| GB191216350A (en) | 1912-12-19 |
| DE269205C (en) | |
| DE296940C (en) |
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