DE271159C - - Google Patents
Info
- Publication number
- DE271159C DE271159C DENDAT271159D DE271159DA DE271159C DE 271159 C DE271159 C DE 271159C DE NDAT271159 D DENDAT271159 D DE NDAT271159D DE 271159D A DE271159D A DE 271159DA DE 271159 C DE271159 C DE 271159C
- Authority
- DE
- Germany
- Prior art keywords
- arsenic
- parts
- phosphorus
- acid
- water
- 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
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910052785 arsenic Inorganic materials 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- RGTIBVZDHOMOKC-UHFFFAOYSA-N stearolic acid Chemical compound CCCCCCCCC#CCCCCCCCC(O)=O RGTIBVZDHOMOKC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- -1 chloroarsenic behenolic acid Chemical compound 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type 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
-
- 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
- C07F9/74—Aromatic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 271159 KLASSE 12 o. GRUPPE- M 271159 CLASS 12 or GROUP
Dr. FELIX HEINEMANN in BERLIN.Dr. FELIX HEINEMANN in BERLIN.
Zusatz zum Patent 257641.*)Addition to patent 257641. *)
Patentiert im Deutschen Reiche vom 31. Januar 1913 ab. Längste Dauer: 29.November 1926.Patented in the German Empire on January 31, 1913. Longest duration: November 29, 1926.
Durch Patent 257641 ist ein Verfahren zur Darstellung von arsen- und phosphorhaltigen Fettsäuren geschützt, .welches darin besteht, daß man die Säuren der Acetylenreihe mit den Trihalogenderivaten des Arsens und des Phosphors erhitzt. Nach dem Verfahren des Zusatzpatents 268829 wird das teure und giftige A s Cl3 durch A s2 O3 und Salzsäure ersetzt. Es wurde nun weiter gefunden, daß man anstatt der fertigen Trihalogenderivate des Arsens und Phosphors auch solche Reagenzien verwenden kann, welche diese Halogenderivate ohne Abspaltung von Wasser liefern, wie Phosphor oder Arsen und Sulfurylchlorid oder A s2 O8 und Thionylchlorid usw. Diese Abänderung hat vor dem Verfahren des Zusatzpatents 268829 wiederum den Vorteil, daß bei der Reaktion kein Wasser frei wird und sich dadurch die Anwendung wasserbindender Mittel erübrigt.A process for the preparation of arsenic and phosphorus-containing fatty acids is protected by patent 257641, which consists in heating the acids of the acetylene series with the trihalogen derivatives of arsenic and phosphorus. According to the procedure of the additional patent 268829, the expensive and toxic A s Cl 3 is replaced by A s 2 O 3 and hydrochloric acid. It has now further been found that can be used instead of the finished Trihalogenderivate of arsenic and phosphorus also such reagents which provide these halogen derivatives without elimination of water, such as phosphorus or arsenic, and sulfuryl chloride, or A S 2 O 8 and thionyl chloride, etc. has This amendment Against the process of the additional patent 268829 the advantage that no water is released during the reaction and thus the use of water-binding agents is unnecessary.
672 Teile Bebenolsäure werden mit 500 Teilen Arsenigsäureanhydrid in einem mit Rückfluß versehenen Gefäß gemischt und nach und nach unter Rühren mit 1000 Teilen Thionylchlorid versetzt. Nachdem die anfangs auftretende Erwärmung nachgelassen hat, bringt man die1 Temperatur der Reaktionsmasse unter Rühren auf 135 ° und hält 6 Stunden auf dieser Temperatur. Nach dem Erkalten destilliert man im Vakuum die niedrig siedenden Anteile (überschüssiges SO CP und ÄsCl3) ab, nimmt den Rückstand mit Äther auf und wäscht mit Wasser, bis die Waschwässer neutral ablaufen. Darauf destilliert man den Äther ab, löst den Rückstand in wenig Alkohol und gießt in eiskalte Normalkalilauge. Nachdem man einige Minuten geschüttelt hat, wird mit Salzsäure angesäuert und ausgeäthert. Die Ätherlösung wird neutral gewaschen, getrocknet und vom Äther befreit Man erhält so die Ghlorarsenbehenolsäure als braunes, dickes öl von den im Beispiel II des Hauptpatents beschriebenen Eigenschaften.672 parts of Bebenolic acid are mixed with 500 parts of arsenic anhydride in a vessel provided with reflux, and 1000 parts of thionyl chloride are gradually added with stirring. After initially appearing warming has subsided, bringing the one temperature of the reaction mass with stirring to 135 ° and holding for 6 hours at this temperature. After cooling, the low-boiling components (excess SO CP and ÄsCl 3 ) are distilled off in vacuo, the residue is taken up in ether and washed with water until the wash waters run off neutral. The ether is then distilled off, the residue is dissolved in a little alcohol and poured into ice-cold normal potassium hydroxide solution. After shaking for a few minutes, it is acidified with hydrochloric acid and extracted with ether. The ethereal solution is washed neutral, dried and freed from ether. The chloroarsenic behenolic acid is obtained in this way as a brown, thick oil with the properties described in Example II of the main patent.
280 Teile Stearolsäure werden mit 150 Teilen gepulvertem Arsen gemischt und in einem mit Rückfiußkühlung versehenen Gefäß mit 405 Teilen Sulfurylchlorid nach und nach unter Rühren versetzt. Man erhitzt die Masse dann 5 bis 6 Stunden auf 145 °. Nach beendeter Reaktion werden im Vakuum bei 100 ° die niedrig siedenden Anteile abdestilliert.280 parts of stearic acid are mixed with 150 parts of powdered arsenic and in one with Reflux-cooled vessel with 405 parts of sulfuryl chloride gradually with stirring offset. The mass is then heated to 145 ° for 5 to 6 hours. After finished The reaction is carried out in vacuo at 100 ° low-boiling fractions distilled off.
Der Rückstand wird dann genau wie im Beispiel 1 verarbeitet.The residue is then processed exactly as in Example 1.
Man erhält so die Chlorarsenstearolsäure von den im ersten Beispil des Hauptpatents angegebenen Eigenschaften.The arsenic chlorostearolic acid is thus obtained from those in the first example of the main patent specified properties.
*) Frühere Zusatzpatente: 268829 und 271158.*) Earlier additional patents: 268829 and 271158.
280 Teile Stearolsäure werden' mit 62 Teilen amorphem Phosphor gemischt und in einem mit Rückflußkühlung versehenen Gefäß nach und nach mit 405 Teilen Sulfurylchlorid unter Rühren versetzt, darauf wird die Masse 5 Stunden auf 140 ° erhitzt und nach dem Erhitzen in der im Beispiel III des Hauptpatents beschriebenen Weise weiter verarbeitet.280 parts of stearolic acid are 'mixed with 62 parts of amorphous phosphorus and in one refluxed vessel gradually with 405 parts of sulfuryl chloride under Stirring is added, then the mass is heated to 140 ° for 5 hours and after heating further processed in the manner described in Example III of the main patent.
Claims (1)
Abänderung des durch das Hauptpatent 257641 geschützten Verfahrens zur Darstellung von Arsen und Phosphor enthaltenden Säuren der Acetylenreihe, dadurch gekennzeichnet, daß man an Stelle der Trihalogenderivate des Arsens und Phosphors solche Mischungen anwendet, welche diese Körper ohne Abspaltung von Wasser liefern. Patent claim:
Modification of the process protected by the main patent 257641 for the preparation of arsenic and phosphorus-containing acids of the acetylene series, characterized in that mixtures are used in place of the trihalogen derivatives of arsenic and phosphorus which give these bodies without splitting off water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE291614T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE271159C true DE271159C (en) | 1900-01-01 |
Family
ID=6068887
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT273219D Expired DE273219C (en) | |||
| DENDAT271159D Expired DE271159C (en) | |||
| DENDAT291614D Expired DE291614C (en) | |||
| DENDAT257641D Expired DE257641C (en) | |||
| DENDAT268829D Expired DE268829C (en) | |||
| DENDAT271158D Expired DE271158C (en) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT273219D Expired DE273219C (en) |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT291614D Expired DE291614C (en) | |||
| DENDAT257641D Expired DE257641C (en) | |||
| DENDAT268829D Expired DE268829C (en) | |||
| DENDAT271158D Expired DE271158C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (6) | DE271158C (en) |
-
0
- DE DENDAT273219D patent/DE273219C/de not_active Expired
- DE DENDAT271159D patent/DE271159C/de not_active Expired
- DE DENDAT291614D patent/DE291614C/de not_active Expired
- DE DENDAT257641D patent/DE257641C/de not_active Expired
- DE DENDAT268829D patent/DE268829C/de not_active Expired
- DE DENDAT271158D patent/DE271158C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE291614C (en) | 1916-04-27 |
| DE268829C (en) | 1900-01-01 |
| DE271158C (en) | 1900-01-01 |
| DE273219C (en) | 1900-01-01 |
| DE257641C (en) | 1900-01-01 |
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