CH311474A - Process for producing an organic phosphorus compound. - Google Patents
Process for producing an organic phosphorus compound.Info
- Publication number
- CH311474A CH311474A CH311474DA CH311474A CH 311474 A CH311474 A CH 311474A CH 311474D A CH311474D A CH 311474DA CH 311474 A CH311474 A CH 311474A
- Authority
- CH
- Switzerland
- Prior art keywords
- producing
- phosphorus compound
- organic phosphorus
- parts
- new compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 4
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- -1 etc. Chemical compound 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Description
Verfahren zur Herstellung einer organischen Phosphorverhindung. Es wurde gefunden, dass man zu der neuen Verbindung der Formel
EMI0001.0002
gelangt, wenn man Diäthylchlorphosphat mit (y- Mercapto-propylen) - isopropylidendioxyd umsetzt. Die neue Verbindung ist ein hoch siedendes Öl und kann als Schädlingsbekämp fungsmittel verwendet werden.
Man arbeitet zweckmässig bei Raumtem peratur oder mässig erhöhter Temperatur und in inerten Verdünnungsmitteln; als solche kommen z. B. Kohlenwasserstoffe, wie Benzol, Toluol usw., Chlorbenzol und ähnliche, oder auch Ketone, wie Aceton, Methyläthylketon, Methylpropylketon, in Frage. Die Umsetzung kann durch Zusatz von metallischem Kupfer katalytisch beschleunigt werden. Zweckmässig wird das (y-Mercapto-propylen)-isopropyliden- dioxyd in Form des Natriumsalzes verwendet.
Beispiel: Zu einer Suspension von 1,15 Teilen zer stäubtem Natrium in 40 Volumteilen Toluol werden unter Rühren bei 30-40 langsam 7,4 Teile (y-Mercapto-propylen)-isopropylen- dioxyd zugegeben. Am Schluss wird auf 50 bis 60 aufgeheizt, worauf nach einer Stunde die Bildung des Natriumsalzes beendet ist. Hierauf werden bei 20-30 8,6 Teile Diäthyl- chlorphosphat zugetropft und eine Stunde bei Raumtemperatur weitergerührt.
Nach Zu gabe von 3 Volumteilen Wasser scheidet sich das Kochsalz ab, und die Toluollösung kann abgegossen werden. Nach dem Abdestillieren des Toluols im Vakuum bleiben 11,6 Teile eines farblosen Öls, das unter teilweiser Zersetzung bei 129-1351110,25 mm destilliert. Das erhal tene Produkt entspricht der Formel
EMI0001.0030
Process for the production of an organic phosphorus compound. It was found that the new compound of the formula
EMI0001.0002
obtained when diethyl chlorophosphate is reacted with (γ-mercapto-propylene) isopropylidene dioxide. The new compound is a high-boiling oil and can be used as a pest control agent.
It is expedient to work at room temperature or moderately elevated temperature and in inert diluents; as such come z. B. hydrocarbons such as benzene, toluene, etc., chlorobenzene and the like, or ketones such as acetone, methyl ethyl ketone, methyl propyl ketone, in question. The conversion can be accelerated catalytically by adding metallic copper. The (γ-mercapto-propylene) isopropylidene dioxide is expediently used in the form of the sodium salt.
Example: 7.4 parts of (γ-mercapto-propylene) isopropylene dioxide are slowly added to a suspension of 1.15 parts of atomized sodium in 40 parts by volume of toluene with stirring at 30-40. At the end it is heated to 50 to 60, whereupon the formation of the sodium salt has ended after one hour. Then 8.6 parts of diethyl chlorophosphate are added dropwise at 20-30 and stirring is continued for one hour at room temperature.
After adding 3 parts by volume of water, the common salt separates and the toluene solution can be poured off. After the toluene has been distilled off in vacuo, 11.6 parts of a colorless oil remain, which distills with partial decomposition at 129-1351110.25 mm. The product obtained corresponds to the formula
EMI0001.0030
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311474T | 1952-08-22 | ||
| CH308894T | 1952-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311474A true CH311474A (en) | 1955-11-30 |
Family
ID=25735529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311474D CH311474A (en) | 1952-08-22 | 1952-08-22 | Process for producing an organic phosphorus compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311474A (en) |
-
1952
- 1952-08-22 CH CH311474D patent/CH311474A/en unknown
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