AT55396B - Process for the preparation of aryl substitution products of arsenic acid. - Google Patents
Process for the preparation of aryl substitution products of arsenic acid.Info
- Publication number
- AT55396B AT55396B AT55396DA AT55396B AT 55396 B AT55396 B AT 55396B AT 55396D A AT55396D A AT 55396DA AT 55396 B AT55396 B AT 55396B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- substitution products
- arsenic acid
- aryl substitution
- acid
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 3
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 title claims 2
- 229940000488 arsenic acid Drugs 0.000 title claims 2
- 238000000034 method Methods 0.000 title claims 2
- 238000006467 substitution reaction Methods 0.000 title claims 2
- -1 aromatic diazo compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XBPQKOIGZUZSRO-UHFFFAOYSA-N (4-nitrophenyl)arsinic acid Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)[AsH](O)=O XBPQKOIGZUZSRO-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ZIPJXJGTIGXUSE-UHFFFAOYSA-N 6-diazocyclohexa-2,4-dien-1-ol Chemical class OC1C=CC=CC1=[N+]=[N-] ZIPJXJGTIGXUSE-UHFFFAOYSA-N 0.000 description 1
- IOVGNRBSSGWNQO-UHFFFAOYSA-N CC(NC1=CC=CC([As])=C1)=O Chemical compound CC(NC1=CC=CC([As])=C1)=O IOVGNRBSSGWNQO-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910000413 arsenic oxide Inorganic materials 0.000 description 1
- 229960002594 arsenic trioxide Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PTLRDCMBXHILCL-UHFFFAOYSA-M sodium arsenite Chemical compound [Na+].[O-][As]=O PTLRDCMBXHILCL-UHFFFAOYSA-M 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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ab und dampft das Filtrat zur Trockne. Durch Umkristallisieren aus Wasser kann man von den entstandenen Nebenprodukten trennen und erhält so die p-Nitrophenylarsinsäure, welche aus Wasser umkristallisiert werden kann. Sie ist in Alkohol leicht löslich. Die Ausbeute an p-Nitrophenylarsinsäure ist besser, wenn man auch in diesem Beispiel an Stelle der sauren, eine alkalische
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sodann mit 2'5 Teilen p-nitrophenylarsinigsaurem Natron versetzt.
Sogleich setzt eine starke Sti (kstoffentwicklung ein, deren Aufhören das Ende der Reaktion anzeigt, worauf abfiltriert und das Filtrat mit Salzsäure angesäuert wird. Es scheidet sich nun di, p-Dinitrodiphenylarsill- säure als weisslichgelber Niederschlag ab. Diese Säure ist in Wasser uud Alkohol schwer löslich, die wässerige Lösung der Alkalisalze ist gelb gefärbt. Analog verhalten sich Verbindungen mit positiven Substituenten, wie z. B. m-Azetylaminophenylarsenoxyd usw.
Beispiel 12 : 1'09 Teile p-Aminophenol werden mit 6 Teilen Wasser und 2 Teilen konzentrierter Salzsäure (spezifisches Gewicht 1'16) in Lösung gebracht und in der üblichen Weise diazotiert. Zu diesem Gemisch wird, nachdem es mit konzentrierter Natronlauge alkalisch gemacht ist. bei nicht zu tiefer Temperatur eine Lösung von 1'5 Teilen Natriumarsenit in 6 Teilen Wasser gegeben und solange bei nicht zu stark alkalischer Reaktion erwärmt : bis Jie StickstoSentwicklu'ig 7. Ende ist.
Sodann neutral@@@ert man das Reaktionsgemisch, filtriert von unlöslichen Produkten ab und engt das Filtrat bei neutraler Reaktion zweckmässig mit Tierkohle ein. Aus der so erhaltenen
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Reinigung umkristallisiert werden. Analog verhalten sich die isomeren Aminophenole. Ist die Hydroxylgruppe veräthert oder verestert. dann werden die entsprechenden Äther-bzw. Ester- phenoiarsinsäuren erhalten. Diazophenole mit mehreren OR-Gruppen (r = Wasserstoff, Alkyl, Aryl oder AzyJ), \\1e z. B. Diazoguajakol, reagieren analog.
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and the filtrate evaporates to dryness. By recrystallizing from water, the byproducts formed can be separated and p-nitrophenylarsinic acid is obtained, which can be recrystallized from water. It is easily soluble in alcohol. The yield of p-nitrophenylarsinic acid is better if, in this example, instead of the acidic one, an alkaline one
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then mixed with 2'5 parts of p-nitrophenylarsinigsaurem sodium.
A strong evolution of nitrogen immediately sets in, the cessation of which indicates the end of the reaction, whereupon the filtrate is filtered off and the filtrate is acidified with hydrochloric acid. Di, p-Dinitrodiphenylarsilic acid separates out as a whitish-yellow precipitate. This acid is in water and alcohol Slightly soluble, the aqueous solution of the alkali salts is yellow in color. Compounds with positive substituents, such as m-acetylaminophenyl arsenic oxide etc., behave analogously.
Example 12: 1,09 parts of p-aminophenol are dissolved in 6 parts of water and 2 parts of concentrated hydrochloric acid (specific gravity 1'16) and diazotized in the usual way. This mixture is made alkaline with concentrated sodium hydroxide solution. a solution of 1'5 parts of sodium arsenite in 6 parts of water is added at a temperature that is not too low and the reaction is not too strongly alkaline and the mixture is heated until the end of nitrogen development.
The reaction mixture is then neutral, insoluble products are filtered off and the filtrate is concentrated with animal charcoal in the case of a neutral reaction. From the thus obtained
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Purification to be recrystallized. The isomeric aminophenols behave analogously. Is the hydroxyl group etherified or esterified. then the corresponding ether or. Ester phenoiarsinsäuren obtained. Diazophenols with several OR groups (r = hydrogen, alkyl, aryl or AzyJ), \\ 1e z. B. Diazoguajakol, react analogously.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE55396X | 1910-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT55396B true AT55396B (en) | 1912-09-10 |
Family
ID=5628378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT55396D AT55396B (en) | 1910-01-07 | 1911-01-05 | Process for the preparation of aryl substitution products of arsenic acid. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT55396B (en) |
-
1911
- 1911-01-05 AT AT55396D patent/AT55396B/en active
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