DE421846C - Process for the preparation of complex metallarsenobenzene compounds - Google Patents
Process for the preparation of complex metallarsenobenzene compoundsInfo
- Publication number
- DE421846C DE421846C DEF53935D DEF0053935D DE421846C DE 421846 C DE421846 C DE 421846C DE F53935 D DEF53935 D DE F53935D DE F0053935 D DEF0053935 D DE F0053935D DE 421846 C DE421846 C DE 421846C
- Authority
- DE
- Germany
- Prior art keywords
- water
- compounds
- preparation
- solution
- silver
- 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 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 title description 7
- 239000010949 copper Substances 0.000 claims description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 239000010931 gold Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- AWYSLGMLVOSVIS-UHFFFAOYSA-N phenyl(phenylarsanylidene)arsane Chemical class C1=CC=CC=C1[As]=[As]C1=CC=CC=C1 AWYSLGMLVOSVIS-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910001961 silver nitrate Inorganic materials 0.000 description 5
- -1 formaldehyde sulfoxylate compound Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 3
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 2
- 239000005750 Copper hydroxide Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229910001956 copper hydroxide Inorganic materials 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940100890 silver compound Drugs 0.000 description 2
- 150000003379 silver compounds Chemical class 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- DETXZQGDWUJKMO-UHFFFAOYSA-N alpha-hydroxymethanesulfonic acid Natural products OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 1
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000010956 nickel silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229940083025 silver preparation Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- 239000004552 water soluble powder 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Verfahren zur Darstellung von komplexen metallarsenobenzolverbindungen. Es wurde gefunden, daß man zu komplexen Metallverbindungen der Arsenobenzole dadurch gelangen kann, daß man Arseno-Benzole, welche in der Aminogntppe durch einen sauerstoffhaltigen Rest substituiert sind, wie NH - CH, # COOH oder NH # CH, # S02H, NH # CHZS03H, NH # C02Na oder NH - CHZ # CH(OH) - CHZ(OH), in neutraler oder alkalischer Lösung mit den Oxyden bzw. Hydroxyden der Metalle, wie Kupfer, Silber oder Gold, zusammenbringt. Man gelangt so zu neutralwasserlöslichen Verbindungen, welche eine gute Beständigkeit insbesondere auch gegenüber Kohlensäure besitzen und ebenso wie bekannte, nach anderen Verfahren dargestellte Metallarsenobenzolverbindungen eine vorzügliche trypanocideWirkung besitzen. Die Verbindungen sind braune bis braunschwarze Körper, in Wasser klar löslich, gegen Kohlensäure beständig.Process for the preparation of complex metallarsenobenzene compounds. It has been found that complex metal compounds of arsenobenzenes can be obtained by using arsenobenzenes which are substituted in the amino group by an oxygen-containing radical, such as NH - CH, # COOH or NH # CH, # SO2H, NH # CHZSO3H , NH # C02Na or NH - CHZ # CH (OH) - CHZ (OH), in neutral or alkaline solution with the oxides or hydroxides of metals such as copper, silver or gold. This leads to compounds which are soluble in neutral water and which are particularly resistant to carbonic acid and, like known metallarsenobenzene compounds produced by other processes, have an excellent trypanocidal effect. The compounds are brown to brown-black bodies, clearly soluble in water, resistant to carbonic acid.
B eispiele.Examples.
1. 4 g Silbernitrat werden in Ag(OH) übergeführt. Das gut ausgewaschene Silber-Z, wird in wenig Wasser suspendiert und in eine Lösung von 15 g. einer Formaldehydsulfoxylatverbindung des 4, 4'-Dioxy-3, 3'-diaminoarsenobenzols in 3o ccm Wasser eingetragen. Es entsteht eine tiefschwarze Lösung, die mit Alkohol gefällt wird. Das erhaltene Produkt ist klar in Wasser löslich.1. 4 g of silver nitrate are converted into Ag (OH). The well-washed one Silver-Z is suspended in a little water and converted into a solution of 15 g. a formaldehyde sulfoxylate compound of 4, 4'-dioxy-3, 3'-diaminoarsenobenzene entered in 3o ccm of water. It arises a deep black solution that is precipitated with alcohol. The product obtained is clearly soluble in water.
a. 0,83.- Goldhydroxyd [Au(OH)3] werden mit wenig Wasser verrieben und in eine Lösung von 2,25 g einer Formaldehydsulfoxylatverbindung des Dioxydiaminoarsenobenzols in io ccm Wasser eingetragen. Das Gold geht langsam, schneller beim Erwärmen, in Lösung. Man filtriert, fällt mit absolutem Alkohol und trocknet. Die Verbindung ist klar löslich in Wasser.a. 0.83.- Gold hydroxide [Au (OH) 3] are rubbed with a little water and in a solution of 2.25 g of a formaldehyde sulfoxylate compound of dioxydiaminoarsenobenzene entered in 10 cc of water. The gold goes in slowly, faster when heated Solution. It is filtered, precipitated with absolute alcohol and dried. The connection is clearly soluble in water.
3. Kupferhydroxyd Cu(OH)2 aus 4g CuC12 werden unter Luftabschluß in konzentrierter wäßriger Lösung von 12 g einer Formaldehydsulfoxylatverbindung des Dioxydiaminoarsenobenzols unter Rühren eingetragen. Das Kupferhydroxyd wird vollständig von der Sulfoxylatverbindung gelöst. Die klare Lösung wird dann in ein Gemisch von Alkohol und Äther eingetragen. Das Kupfersalz fällt als gelbliches Pulver aus und wird dann ebenfalls unter Luftabschluß abgesaugt. Der Filterrückstand wird mit Alkohol und Äther gewaschen, möglichst trocken gesaugt und in gutem Vakuum getrocknet. Der getrocknete Niederschlag stellt ein rotbraunes wasserlösliches Pulver dar. Auf Zusatz von Alkali bleibt die Lösung unverändert, Schwefelammonium ruft erst nach einiger Zeit eine Fällung hervor.3. Copper hydroxide Cu (OH) 2 from 4g CuC12 are in the absence of air in concentrated aqueous solution of 12 g of a formaldehyde sulfoxylate compound des Dioxydiaminoarsenobenzols entered with stirring. The copper hydroxide becomes complete dissolved from the sulfoxylate compound. The clear solution is then added to a mixture of Alcohol and ether entered. The copper salt precipitates out as a yellowish powder and is then also suctioned off with exclusion of air. The filter residue becomes with alcohol and ether washed, sucked as dry as possible and dried in a good vacuum. Of the The dried precipitate is a red-brown, water-soluble powder. On addition the solution remains unchanged from alkali, sulfur ammonium only calls after a few Time a precipitate emerged.
4. 5,26 g Natriumsalz des p-Arsenophenylglycins werden in 5o ccm Wasser gelöst. Zur Lösung bringt man 1,25 Ag(OH) aus 479 Silbernitrat. Das Silberhydroxyd löst sich sehr bald auf. Nach Lösung filtriert man und fällt die neue Verbindung mit Alkohol aus. Sie stellt ein braunschwarzes Pulver dar und ist in Wasser löslich.4. 5.26 g of the sodium salt of p-arsenophenylglycine will dissolved in 50 cc of water. 1.25 Ag (OH) from 479 silver nitrate are brought to the solution. The silver hydroxide dissolves very soon. After solution, it is filtered and precipitated the new connection with alcohol. It represents a brown-black powder and is soluble in water.
5. 5,68 g 4, 4'-Bismethylamino-3, 3', 5, 5'-tetraaminoarsenobenzolchlorhydrat werden mit 5 g Natriumbicarbonat und 5o ccm Wasser als carbaminsaures Salz unter Luftabschluß gelöst. Zur Lösung fügt man 1,25 Ag(OH), aus 479 Silbernitrat gewonnen, hinzu. Das Silberhydroxyd wird sehr bald gelöst. Sobald Lösung eingetreten ist, wird filtriert und die Silberverbindung mit Alkohol ausgefällt.5. 5.68 g of 4,4'-bismethylamino-3, 3 ', 5, 5'-tetraaminoarsenobenzene chlorohydrate are mixed with 5 g of sodium bicarbonate and 5o ccm of water as a carbamic acid salt Air exclusion solved. 1.25 Ag (OH), obtained from 479 silver nitrate, is added to the solution. added. The silver hydroxide dissolves very soon. As soon as solution has occurred, is filtered and the silver compound is precipitated with alcohol.
Die neue Verbindung stellt ein braunes Pulver dar und ist Gin Wasser löslich.The new compound is a brown powder and is gin water soluble.
6. 5,98 g der Formaldehydbisulfitverbindung des 4, 4'-Dioxy-3, 3'-diaminoarsenobenzols werden in 25 ccm Wasser gelöst und zur Lösung 1,25 Ag(OH) aus 1,7 Silbernitrat hinzugegeben. Das Silberhydroxyd ist sehr bald gelöst. Nach Filtration wird die neue Silberverbindung mit Alkohol gefällt. Sie bildet ein braunes Pulver und ist in Wasser löslich.6. 5.98 g of the formaldehyde bisulfite compound of 4,4'-dioxy-3, 3'-diaminoarsenobenzene are dissolved in 25 ccm of water and 1.25 Ag (OH) from 1.7 silver nitrate are added to the solution. The silver hydroxide is dissolved very quickly. After filtration it becomes the new silver compound like with alcohol. It forms a brown powder and is soluble in water.
7. 5,5g 4, 4'-Bi=methylamino-3, 3', 5, 5'-t--traaminoarsenobenzolglycid, wie es nach Beispiel 5 des Patents 412171 erhalten wird, werden in 2o ccm Wasser gelöst und dazu Silberoxyd aus 1,7 g Silbernitrat gegeben. Dann wird geschüttelt, bis Lösung eingetreten ist, filtriert und das Filtrat in 5oo ccm Alkohol eingerührt. Man gibt noch 5oo ccm Äther zu und saugt von dem ausgefallenen - Silberpräparat ab, wäscht mit Alkohol und Äther und trocknet im Vakuum. Das Produkt ist dunkelbraun und in Wasser löslich.7. 5.5g 4, 4'-Bi = methylamino-3, 3 ', 5, 5'-t - traaminoarsenobenzene glycid, as is obtained according to Example 5 of patent 412171, in 2o ccm of water dissolved and added silver oxide from 1.7 g of silver nitrate. Then it is shaken until solution has occurred, filtered and the filtrate stirred into 5oo ccm of alcohol. Another 500 cc of ether is added and the precipitated silver preparation is sucked off off, wash with alcohol and ether and dry in vacuo. The product is dark brown and soluble in water.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF53935D DE421846C (en) | 1923-04-09 | 1923-04-10 | Process for the preparation of complex metallarsenobenzene compounds |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE214237T | 1923-04-09 | ||
| DEF53935D DE421846C (en) | 1923-04-09 | 1923-04-10 | Process for the preparation of complex metallarsenobenzene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE421846C true DE421846C (en) | 1925-11-19 |
Family
ID=31947338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF53935D Expired DE421846C (en) | 1923-04-09 | 1923-04-10 | Process for the preparation of complex metallarsenobenzene compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE421846C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010000579A1 (en) | 2010-02-26 | 2011-09-01 | Samson Ag | Workpiece holder for holding a workpiece to be machined in a machine tool |
-
1923
- 1923-04-10 DE DEF53935D patent/DE421846C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010000579A1 (en) | 2010-02-26 | 2011-09-01 | Samson Ag | Workpiece holder for holding a workpiece to be machined in a machine tool |
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