CH300757A - Process for producing a phosphoric acid ester. - Google Patents
Process for producing a phosphoric acid ester.Info
- Publication number
- CH300757A CH300757A CH300757DA CH300757A CH 300757 A CH300757 A CH 300757A CH 300757D A CH300757D A CH 300757DA CH 300757 A CH300757 A CH 300757A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphoric acid
- acid ester
- isopropyl
- methyl
- producing
- 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 4
- IOJBNVBZZYSKNG-UHFFFAOYSA-N C[ClH]P(=S)(Cl)[ClH]C Chemical compound C[ClH]P(=S)(Cl)[ClH]C IOJBNVBZZYSKNG-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 12
- 238000003756 stirring Methods 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 238000009835 boiling Methods 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
- 238000001914 filtration 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
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material 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
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
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 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-isopropyl - 4- methyl-pyrimi- dyl- (6) ] -dimethylester, stellt eine leicht ge färbte Flüssigkeit dar, die unter 0,001 mm Druck bei 88 bis 90 siedet. Sie soll als Wirk substanz für Schädlingsbekämpfungsmittel Verwendung finden.
<I>Beispiel 1:</I> 152 Teile 2 - Isopropyl - 4 - methyl - 6 - oxy- pyrimidin werden mit 138 Teilen Kalium- carbonat und 2000 Teilen Benzol versetzt und unter Rühren zum Sieden erhitzt. Dabei wird das bei der Enolatbildung freiwerdende Wasser mit Benzol azeotrop abdestilliert. So bald sich im Destillat kein Wasser mehr ab- .
scheidet, wird auf 60 bis 70 abgekühlt, 162 Teile Dimethylthiophosphorsäurechlorid zu- getropft und anschliessend 10 Stunden unter Rückfluss gekocht. Nach dem Erkalten wird der Reaktionsmischung unter gutem Rühren # so lange Kaliumcarbonatlösung zugesetzt, bis die wässrige .Schicht Phenolphthaleinpapier eben rot anfärbt.
Nach Abtrennen der wässri- gen Schicht wird das Lösungsmittel abdestil- liert. Es bleibt der Thiophosphorsäure-[2-iso- propyl-4-methyl-pyrimidyl- (6) ] -@dimethylester zurück,. der sich im Hoehvakuum destillieren lässt und einen Kochpunkt von 88 bis 90 bei 0,001 mm Druck hat.
Er eignet sieh ohne weitete Reinigung als Wirkstoff. insektizid und @ akarizid wirksamer Präparate.
<I>Beispiel 2:</I> 76 Teile 2 - Isopropyl - 4 - methyl - ,6 - oxy- pyrimidin werden mit der berechneten Menge Kaliumearbonatlösung neutralisiert und zur Trockne eingedampft. Das staubtrockene Salz wird in 500 Teile absolutes Benzol ein getragen und unter Rühren mit 81 Teilen Dimethyl-thiophosphorsäurechlorid versetzt. Das Reaktionsgemisch wird einige Stunden auf 100 bis 110 erhitzt und darauf vom ge bildeten Kochsalz durch Filtration befreit.
Durch Aisschütteln mit Sodalösung werden eventuelle unveränderte Ausgangsmaterialien entfernt. Nach dem Abdestillieren des Ben zols erhält man den in Beispiel. 1 beschrie benen Thiophosphorsäii.re-[2-isopropyl-4-me- thyl-pyrimidy 1- (6) ] -dimethylester: ,
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
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 [2-isopropyl-4-methyl-pyrimidyl- (6)] -dimethyl ester, is a lightly colored liquid that boils at 88 to 90 under 0.001 mm pressure. It should be used as an active substance for pesticides.
<I> Example 1 </I> 152 parts of 2-isopropyl-4-methyl-6-oxy-pyrimidine 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 there is no more water in the distillate.
separates, is cooled to 60 to 70, 162 parts of dimethylthiophosphoric acid chloride are added dropwise and 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. The thiophosphoric acid [2-isopropyl-4-methyl-pyrimidyl- (6)] - @ dimethyl ester remains. which can be distilled in a high vacuum and has a boiling point of 88 to 90 at 0.001 mm pressure.
It is suitable as an active ingredient without further cleaning. Insecticidal and @acaricidal preparations.
<I> Example 2 </I> 76 parts of 2-isopropyl-4-methyl-, 6-oxy-pyrimidine are neutralized with the calculated amount of potassium carbonate solution and evaporated to dryness. The dust-dry salt is introduced into 500 parts of absolute benzene and mixed with 81 parts of dimethyl thiophosphoric acid chloride with stirring. The reaction mixture is heated to 100 to 110 for a few hours and then freed from the sodium chloride formed by filtration.
Any unchanged starting materials can be removed by shaking with soda solution. After the benzene has been distilled off, the example is obtained. 1 described thiophosphoric acid [2-isopropyl-4-methyl-pyrimidy 1- (6)] -dimethyl ester:,
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300757T | 1951-04-20 | ||
| CH294598T | 1951-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300757A true CH300757A (en) | 1954-08-15 |
Family
ID=25733518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300757D CH300757A (en) | 1951-04-20 | 1951-04-20 | Process for producing a phosphoric acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300757A (en) |
-
1951
- 1951-04-20 CH CH300757D patent/CH300757A/en unknown
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