DE538453C - Process for the preparation of complex salts of organic compounds containing phenolic groups - Google Patents
Process for the preparation of complex salts of organic compounds containing phenolic groupsInfo
- Publication number
- DE538453C DE538453C DE1930538453D DE538453DD DE538453C DE 538453 C DE538453 C DE 538453C DE 1930538453 D DE1930538453 D DE 1930538453D DE 538453D D DE538453D D DE 538453DD DE 538453 C DE538453 C DE 538453C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- complex salts
- preparation
- compounds containing
- organic compounds
- 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 6
- 150000003839 salts Chemical class 0.000 title claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000000843 powder Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FIHCMDIDYDOFDJ-UHFFFAOYSA-L copper;azane;sulfate Chemical compound N.[Cu+2].[O-]S([O-])(=O)=O FIHCMDIDYDOFDJ-UHFFFAOYSA-L 0.000 description 3
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 2
- OLXZIGFHNNMHOE-UHFFFAOYSA-N 2-(trichloromethyl)phenol Chemical compound OC1=CC=CC=C1C(Cl)(Cl)Cl OLXZIGFHNNMHOE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 hydroxyl compound Chemical class 0.000 description 2
- 150000004707 phenolate Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Darstellung von Komplexsalzen organischer, Phenolgruppen enthaltender Verbindungen Es wurde gefunden, daß beim Zusammenbringen von ammoniakalischen Lösungen anorganischer Kupfer- und Zinksalze mit negativ substituierten, phenolische Hydroxylgruppen enthaltenden organischen Verbindungen Komplexsalze entstehen, die Ammoniak, die organische Hydroxylverbindung und das Metall enthalten. Zu ihrer Darstellung werden Lösungen von Phenolen oder Phenolaten mit ammoniakalischen Lösungen dieser anorganischen Salze oder Lösungen von Ammonikaten derselben vereinigt, wobei die neuen Verbindungen sich ausscheiden. Dieselben werden durch Wasser schwer hydrolysiert, Säuren und Alkalien bewirken Zersetzung, während sie von Ammoniak und Aminen gelöst werden. Aus diesen Lösungen werden beim Verdunsten der überschüssigen Base die Verbindungen wieder ausgeschieden.Process for the preparation of complex salts of organic phenol groups containing compounds It has been found that when bringing together ammoniacal Solutions of inorganic copper and zinc salts with negatively substituted, phenolic Hydroxyl-containing organic compounds form complex salts which Ammonia, the organic hydroxyl compound and the metal. To their representation solutions of phenols or phenolates with ammoniacal solutions of these inorganic salts or solutions of ammonicates of the same combined, the new connections are eliminated. They are badly hydrolyzed by water, Acids and alkalis cause decomposition while being dissolved by ammonia and amines will. When the excess base evaporates, these solutions become the compounds retired again.
Die neuen Substanzen sollen in der Schädlingsbekämpfung und als Konservierungsmittel Verwendung finden.The new substances are said to be used in pest control and as preservatives Find use.
Beispiel 1 21 Teile Trichlorkresol werden in 7o Teilen Methanol gelöst und zu einer Lösung von 12,5 Teilen Kupferammoniaksulfat in 3oo Teilen Wassergegeben. Der ausfallende braune Niederschlag wird abgesaugt, mit Wasser gewaschen und getrocknet. Die Verbindung stellt ein braunes Pulver dar, das in Methanol und Aceton leicht löslich, in Äther und Benzol etwas löslich ist. Von Ammoniak und Aminen wird es mit blauer Farbe aufgenommen.Example 1 21 parts of trichlorocresol are dissolved in 70 parts of methanol and added to a solution of 12.5 parts of copper ammonia sulfate in 300 parts of water. The brown precipitate which separates out is filtered off with suction, washed with water and dried. The compound is a brown powder that dissolves easily in methanol and acetone soluble, somewhat soluble in ether and benzene. From ammonia and amines it gets recorded with blue color.
Beispiel 2 g Teile Kupferchlorid werden in 23 Teilen Wasser gelöst, 17 Teile Ammoniak hinzugefügt und darauf so viel Essigsäure, bis gerade wieder eine Trübung entsteht. Diese Lösung wird unter Rühren zu einer solchen von 21 Teilen Trichlorkresol in 7o Teilen Methanol gegeben und mit 3oo Teilen Wasser verdünnt. Die Eigenschaften der entstehenden Verbindung gleichen der nach Beispiel 1 erhaltenen.Example 2 g parts of copper chloride are dissolved in 23 parts of water, 17 parts ammonia added and then enough acetic acid until just one more Cloudiness arises. This solution becomes that of 21 parts with stirring Trichlorocresol is added to 70 parts of methanol and diluted with 300 parts of water. The properties of the resulting compound are the same as those obtained in Example 1.
Beispiel 3 23 Teile Trichlorkresolnatrium, in 5oo Teilen Wasser gelöst, werden unter Rühren zu 12,5 Teilen Kupferammoniaksulfat in 3oo Teilen Wasser gegeben. Die Eigenschaften der entstehenden Verbindung gleichen den vorhergenannten.Example 3 23 parts of trichlorocresol sodium, dissolved in 500 parts of water, are added with stirring to 12.5 parts of copper ammonia sulfate in 300 parts of water. The properties of the resulting compound are similar to those mentioned above.
Beispiel q.Example q.
1g Teile Trichlorphenol in 7o Teilen Methanol werden zu einer Lösung von 12,5 Teilen Kupferammoniaksulfat in 3oo Teilen Wasser gegeben. Die ausfallende Verbindung stellt ein dunkelbraunes Pulver dar mit gleichen Eigenschaften wie bei Beispiel i.1 g part of trichlorophenol in 70 parts of methanol become a solution given by 12.5 parts of copper ammonia sulfate in 300 parts of water. the The precipitating compound is a dark brown powder with the same properties as in example i.
Beispiel 5 Es wird analog wie in Beispiel i unter Verwendung von 2, 4-Dinitrophenol gearbeitet. Die neue Verbindung ist ein grünes Pulver, das sich in Ammoniak mit grüner Farbe löst. Sie ist bedeutend schwerer entzündlich als das freie Dinitrophenol oder dessen Phenölate.Example 5 The procedure is analogous to that in Example i, using 2, 4-Dinitrophenol worked. The new compound is a green powder that is Dissolves in ammonia with a green color. It's significantly more flammable than that free dinitrophenol or its phenolates.
Beispiel 6 Man arbeitet analog Beispiel i unter Verwendung von 2, 4-Dichlorphenol. Die Komplexverbindung ist ein rotbraunes Pulver.Example 6 The procedure is analogous to Example i using 2, 4-dichlorophenol. The complex compound is a red-brown powder.
Beispiel 7 ' Es wird analog Beispiel i unter Verwendung von 8-Oxychinolin gearbeitet und hierbei eine olivgrüne Komplexverbindung erhalten. Beispiel 8 ' i3 Teile Chlorzink werden in 63 Teilen Wasser und 30 Teilen Ammoniak gelöst, zu einer Lösung von 21 Teilen Trichlorkresolin Zoo Teilen Methanol gegeben und mit 3oo Teilen Wasser verdünnt. Die neue Verbindung ist weiß, löst sich schwer in Methanol und wäßrigem Ammoniak, leicht in mit Ammoniak gesättigtem Methanol, Glykol und Glycerin.Example 7 'The procedure is analogous to Example i, using 8-oxyquinoline, and an olive-green complex compound is obtained. EXAMPLE 8 13 parts of zinc chloride are dissolved in 63 parts of water and 30 parts of ammonia, added to a solution of 21 parts of trichlorocresoline and zoo parts of methanol and diluted with 300 parts of water. The new compound is white, difficult to dissolve in methanol and aqueous ammonia, easily dissolved in methanol, glycol and glycerin saturated with ammonia.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE539574T | 1930-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE538453C true DE538453C (en) | 1931-11-13 |
Family
ID=6558610
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930538453D Expired DE538453C (en) | 1930-05-16 | 1930-04-20 | Process for the preparation of complex salts of organic compounds containing phenolic groups |
| DE1930539574D Expired DE539574C (en) | 1930-05-16 | 1930-05-16 | Process for the preparation of complex salts of organic compounds containing phenolic groups |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1930539574D Expired DE539574C (en) | 1930-05-16 | 1930-05-16 | Process for the preparation of complex salts of organic compounds containing phenolic groups |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE538453C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2630419A (en) * | 1949-09-10 | 1953-03-03 | Union Carbide & Carbon Corp | Polyester resins modified with complex metal-phenol-nitrogen compounds |
-
1930
- 1930-04-20 DE DE1930538453D patent/DE538453C/en not_active Expired
- 1930-05-16 DE DE1930539574D patent/DE539574C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2630419A (en) * | 1949-09-10 | 1953-03-03 | Union Carbide & Carbon Corp | Polyester resins modified with complex metal-phenol-nitrogen compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE539574C (en) | 1931-11-28 |
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