CH300741A - Process for producing a phosphoric acid ester. - Google Patents
Process for producing a phosphoric acid ester.Info
- Publication number
- CH300741A CH300741A CH300741DA CH300741A CH 300741 A CH300741 A CH 300741A CH 300741D A CH300741D A CH 300741DA CH 300741 A CH300741 A CH 300741A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphoric acid
- acid ester
- producing
- compound
- formula
- 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
- 150000001875 compounds Chemical class 0.000 claims description 6
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 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
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 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
- JRQMRDBHOIOIIL-UHFFFAOYSA-N 3-methyl-1,5-dihydropyrazol-4-one Chemical compound CC1=NNCC1=O JRQMRDBHOIOIIL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000004480 active ingredient Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
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)
Description
Verfahren zur Herstellung eines Phosphorsänreesters. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Phos- phorsäureesters. Das Verfahren ist dadurch gekennzeichnet, 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 Verlaufe des Verfahrens sich abspaltenden Rest, wie Wasserstoff oder ein Kation, bedeutet, umsetzt.
Die erhaltene neue Verbindung, der Thio- phosphorsäure- [3-anethyl-pyrazolyl-(5) ] -di- äthylester, stellt eine leicht gefärbte Flüssigkeit dar, die sich nicht unzersetzt destillieren lä.sst.
Sie soll als Wirksubstanz für Schädlings- bekämpfungsmittel Verwendung finden. Beispiel: 98 Teile 3-Methyl-pyrazolon- (5) werden mit 138 Teilen Kaliumcarbonat und 2000 Tei len Benzol versetzt und unter Rühren zum Sieden erhitzt.
Dabei wird das bei der Enolatbildung freiwerdende Wasser mit Benzol azeotro.p abdestilliert. Sobald sich im Destillat kein Wasser mehr abscheidet, wird auf 60 bis 70 ,abgekühlt, 190 Teile Diäthyl- thiophosphorsäurechlorid fugetropft und an schliessend 10 Stunden unter Rückfhtss ge kocht.
Nach dem Erkalten wird der Reak tionsmischung unter gutem Rühren so lange galiumcarbonatlösung zugesetzt, bis die wäss- rige Schicht Phenolphthaleinpapier eben rot anfärbt. Nach Abtrennen der wässrigen Schicht wird das Lösungsmittel abdestilliert. Es bleibt der Thiophosphorsäure-[3-methyl- pyrazolyl-(5)]-diäthylester als schwach ge färbte Flüssigkeit zurück, der sich nicht un- zersetzt destillieren lässt.
Process for the production of 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
where 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 thiophosphoric acid [3-anethyl-pyrazolyl- (5)] -diethyl ester, is a slightly colored liquid which cannot be distilled without decomposition.
It should be used as an active ingredient for pesticides. Example: 98 parts of 3-methylpyrazolone (5) 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 distilled off with benzene azeotro.p. As soon as no more water separates out in the distillate, the mixture is cooled to 60 to 70 parts, 190 parts of diethyl thiophosphoric acid chloride are added dropwise and the mixture is then refluxed for 10 hours.
After cooling, the reaction mixture 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. The thiophosphoric acid [3-methylpyrazolyl (5)] diethyl ester remains as a weakly colored liquid which cannot be distilled without decomposition.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294598T | 1951-04-20 | ||
| CH300741T | 1951-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300741A true CH300741A (en) | 1954-08-15 |
Family
ID=25733502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300741D CH300741A (en) | 1951-04-20 | 1951-04-20 | Process for producing a phosphoric acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300741A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700687A (en) * | 1969-04-05 | 1972-10-24 | Bayer Ag | (thiono) phosphoric (phosphonic)-acid esters |
| US3700686A (en) * | 1969-03-14 | 1972-10-24 | Bayer Ag | O-alkyl-o-pyrazolyl-phosphoric, phosphonic, thionophosphoric and thionophosphonic acid esters |
-
1951
- 1951-04-20 CH CH300741D patent/CH300741A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700686A (en) * | 1969-03-14 | 1972-10-24 | Bayer Ag | O-alkyl-o-pyrazolyl-phosphoric, phosphonic, thionophosphoric and thionophosphonic acid esters |
| US3700687A (en) * | 1969-04-05 | 1972-10-24 | Bayer Ag | (thiono) phosphoric (phosphonic)-acid esters |
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