CH300759A - Process for producing a phosphoric acid ester. - Google Patents
Process for producing a phosphoric acid ester.Info
- Publication number
- CH300759A CH300759A CH300759DA CH300759A CH 300759 A CH300759 A CH 300759A CH 300759D A CH300759D A CH 300759DA CH 300759 A CH300759 A CH 300759A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphoric acid
- acid ester
- dimethyl
- producing
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000003014 phosphoric acid esters Chemical class 0.000 title claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent 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
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines Phosphorsäureesters. Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Phosphor- säureesters. Das Verfahren ist dadurch ge kennzeichnet, dass man eine Verbindung der Formel
EMI0001.0009
worin X Chlor oder Brom bedeutet, mit einer Verbindung der Formel
EMI0001.0010
worin Y einen im Verlauf des Verfahrens sich abspaltenden Rest, wie Wasserstoff oder ein Kation, bedeutet, umsetzt.
Die erhaltene neue Verbindung, der Phos phorsäure- [2,6 -dimethyl-pyridyl- (4) ] -diäthyl- ester, stellt eine leicht gefärbte Flüssigkeit dar, die unter 0,2 mm Druck bei 118 bis 120 siedet. Sie soll als Wirksubstanz für Schäd- lingsbekämpfungsmittel Verwendung finden. <I>Beispiel 1:</I> 123 Teile 2,6-Dimethyl-4-oxy-pyridin wer den mit 138 Teilen Kaliumcarbonat und 2000 Teilen Benzol versetzt und unter Rüh ren zum Sieden erhitzt.
Dabei wird das bei der Enolatbildung freiwerdende Wasser mit Benzol azeotrop abdestilliert. Sobald sich im Destillat kein Wasser mehr abscheidet, wird auf 60 bis 70 abgekühlt, 174 Teile Diäthyl- phosphorsäurechlorid zugetropft und an schliessend 10 Stunden unter Rückfluss ge kocht.
Nach dem Erkalten wird der Reak- tionsmischung unter gutem Rühren so lange Kaliumcarbonatlösung zugesetzt, bis die wäss- rige Schicht Phenolphthaleinpapier eben rot anfärbt.
Nach Abtrennen der wässrigen Schicht wird das Lösungsmittel abdestilliert. Es bleibt. der Phosphorsä-Ltre-[2,6-dimethyl- pyridyl-(4)]-diäthylester zurück, der unter 0,2 mm. Druck bei 118 bis 120 siedet. Er eignet sich ohne weitere Reinigung als Wirk stoff insektizid Lund akarizid wirksamer Prä parate.
<I>Beispiel 2:</I> 12,3 Teile 2,6 - Dimethyl - 4 - oxy - pyridin werden in eine- Lösung von 2,3 Teilen Na trium in 150 Teilen-abs. Äthanol eingetragen.
Zu der erhaltenen Lösung des Natriumsalzes des 2,i6-Dimethyl-4-oxy-pyridins fügt man 17,4 Teile Diäthylphosphorsäurechlorid und kocht 9 Stunden unter Rückfluss. Die ab gekühlte Lösung wird vom ausgeschiedenen Natriumchlorid abfiltriert und das Filtrat im Vakuum vom Alkohol befreit. Durch Aus- schütteln mit Wasser lässt sich allfälliges nicht umgesetztes 2,6-Dimethyl-4-oxy-pyridin ab trennen.
Man erhält den in Beispiel 1 be schriebenen Phosphorsäure- [2,6- dimethyl- pyridyl- (4) ] =diäthylester.
Process for producing a phosphoric acid ester. The present patent relates to a process for the production of a phosphoric acid ester. The process is characterized in that a compound of the formula
EMI0001.0009
wherein X is chlorine or bromine, with a compound of the formula
EMI0001.0010
wherein Y is a radical which is split off in the course of the process, such as hydrogen or a cation.
The new compound obtained, the phosphoric acid [2,6-dimethyl-pyridyl- (4)] -diethyl ester, is a light-colored liquid that boils at 118 to 120 under 0.2 mm pressure. It should be used as an active substance for pest control agents. <I> Example 1: </I> 123 parts of 2,6-dimethyl-4-oxy-pyridine are mixed with 138 parts of potassium carbonate and 2000 parts of benzene and heated to the boil with stirring.
The water released during enolate formation is azeotropically distilled off with benzene. As soon as no more water separates out in the distillate, the mixture is cooled to 60 to 70, 174 parts of diethylphosphoric acid chloride are added dropwise and the mixture is then refluxed for 10 hours.
After cooling, potassium carbonate solution is added to the reaction mixture with thorough stirring until the aqueous layer of phenolphthalein paper just turns red.
After the aqueous layer has been separated off, the solvent is distilled off. It stays. the Phosphorsä-Ltre- [2,6-dimethylpyridyl- (4)] - diethyl ester, which is below 0.2 mm. Pressure boils at 118 to 120. It is suitable as an active ingredient in insecticidal and acaricidal preparations without further cleaning.
<I> Example 2: </I> 12.3 parts of 2,6 - dimethyl - 4 - oxy - pyridine are in a solution of 2.3 parts of sodium in 150 parts of abs. Ethanol registered.
17.4 parts of diethylphosphoric acid chloride are added to the resulting solution of the sodium salt of 2,16-dimethyl-4-oxy-pyridine and the mixture is refluxed for 9 hours. The cooled solution is filtered off from the precipitated sodium chloride and the filtrate is freed from alcohol in vacuo. Any unreacted 2,6-dimethyl-4-oxy-pyridine can be separated off by shaking with water.
The phosphoric acid [2,6-dimethylpyridyl- (4)] = diethyl ester described in Example 1 is obtained.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH294598T | 1951-04-20 | ||
CH300759T | 1951-04-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH300759A true CH300759A (en) | 1954-08-15 |
Family
ID=25733520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH300759D CH300759A (en) | 1951-04-20 | 1951-04-20 | Process for producing a phosphoric acid ester. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH300759A (en) |
-
1951
- 1951-04-20 CH CH300759D patent/CH300759A/en unknown
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