CH300758A - Process for producing a phosphoric acid ester. - Google Patents
Process for producing a phosphoric acid ester.Info
- Publication number
- CH300758A CH300758A CH300758DA CH300758A CH 300758 A CH300758 A CH 300758A CH 300758D A CH300758D A CH 300758DA CH 300758 A CH300758 A CH 300758A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphoric acid
- acid ester
- producing
- compound
- distilled
- 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 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 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 12
- 238000003756 stirring Methods 0.000 description 3
- JRQMRDBHOIOIIL-UHFFFAOYSA-N 3-methyl-1,5-dihydropyrazol-4-one Chemical compound CC1=NNCC1=O JRQMRDBHOIOIIL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 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
- 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
- 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
- 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
- C07F9/650905—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 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 V erbindimg der Formel
EMI0001.0011
worin Y einen im Verlauf des Verfahrens sich abspaltenden Rest, wie Wasserstoff oder ein Kation, bedeutet,
umsetzt.
Die erhaltene neue Verbindung, der Phos phorsäure- [3 -methyl-pyrazolyl- (5) ] -diäthyl- ester, stellt eine leicht gefärbte Flüssigkeit dar, die sich nicht urzersetzt destillieren lässt. Sie soll als Wirksubstanz für Schäd lingsbekämpfungsmittel Verwendung finden. <I>Beispiel 1:</I> 98 Teile 3-Methyl-pyrazolon-(5) werden mit 138 Teilen Kaliumcarbonat und 2000 Tei- ].en Benzol versetzt und unter Rühren zum Sieden erhitzt.
Dabei wird das bei der Enolatbildung freiwerdende Wasser mit Ben zol azeotrop abdestilliert. Sobald sich im Destillat kein Wasser mehr abscheidet, wird auf 60 bis 70 abgekühlt, 174 Teile Diäthyl- phosphorsäurechlorid zugetrrnpft 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 Phosphorsäure-[3-methyl-pyr- azolyl - (5) ] - diäthylester zurück, der sich nicht urzersetzt destillieren lässt. Er eignet sich ohne weitere Reinigung als Wirkstoff insektizid und akarizid wirksamer Präparate.
<I>Beispiel 2:</I> 49 Teile 3-Methyl-pyrazolon-(5) werden mit der berechneten Menge Kaliumcarbonat- lösung neutralisiert und zur Trockne ein gedampft. Das staubtrockene Salz wird in 500 Teile absolutes Benzol eingetragen und unter Rühren mit 87 Teilen Diäthyl-phos- phorsäurechlorid versetzt. Das Reaktions gemisch wird einige Stunden auf 100 bis 110 erhitzt und darauf vom gebildeten Kochsalz durch Filtration befreit.
Durch Ausschütteln mit Sodalösung werden eventuelle wnverän- derte Ausgangsmaterialien entfernt. Nach dem Abdestillieren des Benzols erhält man den in Beispiel 1 beschriebenen Phosphor säure- [3-methyl-pyrazolyl(5) ] -diäthylester.
Process for producing a phosphoric acid ester. The present patent is 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
EMI0001.0011
where Y is a radical which is split off in the course of the process, such as hydrogen or a cation,
implements.
The new compound obtained, the phosphoric acid [3 -methyl-pyrazolyl- (5)] -diethyl ester, is a slightly colored liquid that cannot be distilled after decomposition. It should be used as an active ingredient for pesticides. Example 1: 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 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 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. The phosphoric acid [3-methyl-pyrazolyl - (5)] diethyl ester remains, which cannot be distilled after decomposition. It is suitable as an active ingredient in insecticidal and acaricidal preparations without further cleaning.
<I> Example 2 </I> 49 parts of 3-methylpyrazolone (5) 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 87 parts of diethyl phosphoric acid chloride are added 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 phosphoric acid [3-methyl-pyrazolyl (5)] diethyl ester described in Example 1 is obtained.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300758T | 1951-04-20 | ||
| CH294598T | 1951-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH300758A true CH300758A (en) | 1954-08-15 |
Family
ID=25733519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH300758D CH300758A (en) | 1951-04-20 | 1951-04-20 | Process for producing a phosphoric acid ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH300758A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235928B (en) * | 1960-01-25 | 1967-03-09 | Dow Chemical Co | Process for the production of biocidally active phosphorus or thiophosphoric ester amides |
| 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 CH300758D patent/CH300758A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1235928B (en) * | 1960-01-25 | 1967-03-09 | Dow Chemical Co | Process for the production of biocidally active phosphorus or thiophosphoric ester amides |
| 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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