CH261806A - Process for the preparation of a phosphorus-containing ester. - Google Patents
Process for the preparation of a phosphorus-containing ester.Info
- Publication number
- CH261806A CH261806A CH261806DA CH261806A CH 261806 A CH261806 A CH 261806A CH 261806D A CH261806D A CH 261806DA CH 261806 A CH261806 A CH 261806A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- diethyl
- insoluble
- chlorophenol
- phosphoric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 3
- 150000002148 esters Chemical class 0.000 title claims description 3
- 239000011574 phosphorus Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 6
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 claims description 6
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- MXJBIALFHGDUPE-UHFFFAOYSA-N 4-chlorophenol;sodium Chemical compound [Na].OC1=CC=C(Cl)C=C1 MXJBIALFHGDUPE-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- -1 diethyl p-chlorophenyl phosphoric acid Chemical compound 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
Description
Verfahren zur Herstellung eines phosphorhaltigen Esters.
Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung des Diäthyl-p- chlorphenyl-phosphorsäureesters, welches dadurch gekennzeichnet ist, dass Diäthylphos- phorsäurechlorid mit dem wasserlöslichen Salz aus einer stickstofffreien Base und p-Chlorphenol umgesetzt wird.
Die neue Verbindung ist ein wasserklares, in Wasser unlösliches, darin aber leicht emulgierbares 61 vom Kp0,6 146 bis 150 C, welches als Insecticid verwendet werden soll.
Beispiel :
75 g trockenes p-Chlorphenolnatrium, gelöst in 300 cm3 absol. Alkohol, werden unter gutem Rühren und dauernder Kühlung auf etwa 00 C tropfenweise mit 86 g Diäthylphos- phorsäurechlorid versetzt. Nach vollendeter Reaktion wird vom gebildeten Kochsalz abgesa. ugt und das Lösungsmittel abdestilliert.
Man erhält als Rückstand ein Reaktionspro- dukt, das zur Hauptsache aus der Verbindung
EMI1.1
besteht und das durch Hochvakuumdestilla- tion leicht gereinigt werden kann. Es zeigt dann folgende Eigenschaften : Wasserklares, in Wasser unlösliches, aber leicht darin emulgierbares Íl.
Cl-Gehalt ber. 13,26 % gef. 13,8 %
P-Gehalt ber. 11, 74% gef. 11,42%
Spez. Gewicht : 1,241/15 .
Kp. : 146 bis 150# C/0, 6 mm Hg. pATENTANSPRUCH :
Verfahren zur Herstellung des Diäthyl-p- ehlorphenyl-phosphorsäureesters, dadurch gekennzeichnet, dass man Diäthylphosphorsäure- chlorid mit dem wasserlöslichen Salz aus einer stickstofffreien Base und p-Chlorphenol umsetzt.
Die neue Verbindung ist ein wasserklares, in Wasser unlösliches, darin aber leicht emulgierbares Öl vom Kp0,6 146 bis 150 C, welches als Insecticid verwendet werden soll.
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a phosphorus-containing ester.
The present invention relates to a process for producing the diethyl p-chlorophenyl phosphoric acid ester, which is characterized in that diethyl phosphoric acid chloride is reacted with the water-soluble salt of a nitrogen-free base and p-chlorophenol.
The new compound is a water-clear, water-insoluble, but easily emulsifiable 61 with a bp 0.6 146 to 150 C, which is to be used as an insecticide.
Example:
75 g dry p-chlorophenol sodium, dissolved in 300 cm3 absol. Alcohol, 86 g of diethylphosphoric acid chloride are added dropwise with thorough stirring and constant cooling to about 00 C. After the reaction is complete, the sodium chloride formed is removed. and the solvent is distilled off.
The residue obtained is a reaction product, which mainly consists of the compound
EMI1.1
and which can be easily cleaned by high vacuum distillation. It then shows the following properties: Water-clear oil that is insoluble in water but easily emulsifiable in it.
Cl content calculated 13.26% 13.8%
P content calculated 11.74% 11.42%
Specific weight: 1.241 / 15.
Bp: 146 to 150 # C / 0.6 mm Hg.PATENT CLAIM:
Process for the preparation of the diethyl-p-ehlorophenyl-phosphoric acid ester, characterized in that diethyl-phosphoric acid chloride is reacted with the water-soluble salt of a nitrogen-free base and p-chlorophenol.
The new compound is a water-clear, water-insoluble, but easily emulsifiable oil with a bp 0.6 146 to 150 C, which is to be used as an insecticide.
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH257649T | 1947-07-16 | ||
| CH261806T | 1947-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH261806A true CH261806A (en) | 1949-05-31 |
Family
ID=25730102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH261806D CH261806A (en) | 1947-07-16 | 1947-07-16 | Process for the preparation of a phosphorus-containing ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH261806A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870186A (en) * | 1954-12-22 | 1959-01-20 | Ethyl Corp | Dimethyl-(monochlorotolyl)-phosphate |
-
1947
- 1947-07-16 CH CH261806D patent/CH261806A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870186A (en) * | 1954-12-22 | 1959-01-20 | Ethyl Corp | Dimethyl-(monochlorotolyl)-phosphate |
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