CH300760A - Process for producing a phosphoric acid ester. - Google Patents
Process for producing a phosphoric acid ester.Info
- Publication number
- CH300760A CH300760A CH300760DA CH300760A CH 300760 A CH300760 A CH 300760A CH 300760D A CH300760D A CH 300760DA CH 300760 A CH300760 A CH 300760A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- phosphoric acid
- acid ester
- acid
- oxo
- 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
- 239000007788 liquid Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000002253 acid Substances 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
- 238000004140 cleaning Methods 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
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 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
- 239000011541 reaction mixture Substances 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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)
- Agricultural Chemicals And Associated Chemicals (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
EMI0001.0005
worin X Chlor oder Brom bedeutet, mit einer Verbindung der Formel
EMI0001.0006
worin Y einen im Verlauf des Verfahrens sich abspaltenden Rest, wie Wasserstoff oder ein Kation, bedeutet, umsetzt.
Die erhaltene neue Verbindung, der Thio- phosphorsäure- [2 - oxo;-3 -methyl-12, 5 -dihydro- furyl-(4)]-diäthylester, stellt eine leicht ge färbte Flüssigkeit dar, die sich nicht urzer- setzt destillieren lässt. Sie soll als Wirksub- stanz für Schädlingsbekämpfungsmittel Ver wendung finden.
<I>Beispiel:</I> 114 Teile a-Methyl-tetronsäure (2-Oxo- 3-methyl-4-oxy-2,5-dihydrofuran) werden mit 138 Teilen Kaliumcarbonat und 2000 Teilen Aceton versetzt und unter Rühren zum Sie den erhitzt.
Dabei wird .das bei der Enolat- bildung freiwerdende Wasser mit Aceton azeotrop abdestilliert. Sobald sich im Destillat kein Wasser mehr abscheidet, wird auf 60 bis 70 abgekühlt, 190 Teile Diäthylthiophosphor- säurechlorid zugetropft und anschliessend 10 Stunden unter Rückfluss gekocht.
Nach dem Erkalten wird der Reaktionsmischung unter gutem Rühren so lange Kaliumcarbonat- lösung zugesetzt, bis die wässrige Schicht Phenolphthaleinpapier- eben rot anfärbt.
Nach Abtrennen :der wässrigen Schicht wird .das Lösungsmittel abdestilliert. Es bleibt :der Thzophosphorsäure- [2-oxo-3.-arnethyl-2,5-di- hydro-furyl-(4) ],diäthylester als schwach ge färbte Flüssigkeit zurück, die sieh nicht unzersetzt destillieren lässt.
Sie eignet sich ohne weitere Reinigung als Wirkstoff insek- tizid und akarizid wirksamer Präparate.
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
EMI0001.0005
wherein X is chlorine or bromine, with a compound of the formula
EMI0001.0006
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, thiophosphoric acid [2 - oxo; -3-methyl-12, 5 -dihydrofuryl- (4)] diethyl ester, is a slightly colored liquid which does not distill suddenly leaves. It is said to be used as an active substance for pesticides.
<I> Example: </I> 114 parts of a-methyl-tetronic acid (2-oxo-3-methyl-4-oxy-2,5-dihydrofuran) are mixed with 138 parts of potassium carbonate and 2000 parts of acetone and, with stirring, to you heated.
The water released during enolate formation is azeotropically distilled off with acetone. As soon as no more water separates out in the distillate, the mixture is cooled to 60 to 70, 190 parts of diethylthiophosphoric 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 turns red.
After separating: the aqueous layer, the solvent is distilled off. What remains: the thzophosphoric acid [2-oxo-3.-arnethyl-2,5-dihydro-furyl- (4)], diethyl ester as a weakly colored liquid, which cannot be distilled undecomposed.
It is suitable as an active ingredient in insecticidal and acaricidal preparations without further cleaning.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH294598T | 1951-04-20 | ||
| CH300760T | 1951-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300760A true CH300760A (en) | 1954-08-15 |
Family
ID=25733521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300760D CH300760A (en) | 1951-04-20 | 1951-04-20 | Process for producing a phosphoric acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300760A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3121095A (en) * | 1960-07-23 | 1964-02-11 | Thomae Gmbh Dr K | alpha-enolacylates of beta-acyl-gamma-phenyl-alpha-tetronic acids |
| US3432599A (en) * | 1959-07-22 | 1969-03-11 | Shell Oil Co | Organophosphorus insecticides |
-
1951
- 1951-04-20 CH CH300760D patent/CH300760A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3432599A (en) * | 1959-07-22 | 1969-03-11 | Shell Oil Co | Organophosphorus insecticides |
| US3121095A (en) * | 1960-07-23 | 1964-02-11 | Thomae Gmbh Dr K | alpha-enolacylates of beta-acyl-gamma-phenyl-alpha-tetronic acids |
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