CH311478A - Process for producing an organic phosphorus compound. - Google Patents
Process for producing an organic phosphorus compound.Info
- Publication number
- CH311478A CH311478A CH311478DA CH311478A CH 311478 A CH311478 A CH 311478A CH 311478D A CH311478D A CH 311478DA CH 311478 A CH311478 A CH 311478A
- 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
- KKDJPMSEXNCKID-UHFFFAOYSA-N 2-chloro-4-methyl-2-sulfanylidene-1,3,2$l^{5}-dioxaphospholane Chemical compound CC1COP(Cl)(=S)O1 KKDJPMSEXNCKID-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- CJOGVHAUJHBLPB-UHFFFAOYSA-N 2-chloro-4-methyl-1,3,2-dioxaphospholane Chemical compound CC1COP(Cl)O1 CJOGVHAUJHBLPB-UHFFFAOYSA-N 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JWRQWAZJPHHINW-UHFFFAOYSA-L dipotassium benzene carbonate Chemical compound [K+].[K+].[O-]C([O-])=O.C1=CC=CC=C1 JWRQWAZJPHHINW-UHFFFAOYSA-L 0.000 description 1
- -1 etc. Chemical compound 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 239000000575 pesticide Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657109—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s)
- C07F9/657118—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms esters of oxyacids of phosphorus in which one or more exocyclic oxygen atoms have been replaced by (a) sulfur atom(s) non-condensed with carbocyclic rings or heterocyclic rings or ring systems
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 Phosphorverbindung. Es wurde gefunden, dass man zu der neuen Verbindung der Formel
EMI0001.0002
gelangt, wenn man 1,2-Propylenchlor-thio- phosphat mit 2-Hydroxy-propan-dithiol-(1,3)- dimethy läther- (1,3) umsetzt. Die neue Ver bindung ist ein hochsiedendes Öl und kann als Schädlingsbekämpfungsmittel 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, Meth3>lpropylketon, in Frage. Die Umsetzung kann durch Zusatz von metallischem Kupfer katalytisch beschleunigt werden.
<I>Beispiel:</I> Zu einer Lösung von 7,6 Teilen 2-1=1y droxy- propan-dithiol- (1,3) -dimethyläther- (1,3) in 30 Volumteilen trockenem Benzol werden 8 Teile gesiebtes Kaliumcarbonat und 0,3 Teile Kupferpulver gegeben.
Bei gewöhnlicher Tem peratur werden hierauf 8,6 Teile 1,2-Propylen- ehlor-thiophosphat vom Siedepunkt 111 bis 115 /13 mm (hergestellt durch Anlagerung )n Schwefel an 1,2-Propylenchlorphosphit) langsam zugetropft. Nach 5stündigem Erwär- men auf 70-80 ist die Reaktion beendet. Nach dem Filtrieren wird das Benzol ab destilliert, und man erhält das Produkt der Formel
EMI0001.0029
als schwach gelb gefärbtes Öl.
Process for producing an organic phosphorus compound. It was found that the new compound of the formula
EMI0001.0002
obtained when 1,2-propylene chlorothiophosphate is reacted with 2-hydroxy-propane-dithiol- (1,3) - dimethyl ether- (1,3). The new compound is a high-boiling oil and can be used as a pesticide.
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, meth3> propyl ketone in question. The conversion can be accelerated catalytically by adding metallic copper.
<I> Example: </I> 8 parts of dry benzene are sieved to a solution of 7.6 parts of 2-1 = 1y droxy-propane-dithiol- (1,3) -dimethylether- (1,3) in 30 parts by volume of dry benzene Potassium carbonate and 0.3 parts of copper powder are added.
At the usual temperature, 8.6 parts of 1,2-propylene chlorothiophosphate with a boiling point of 111 to 115/13 mm (produced by addition of sulfur to 1,2-propylene chlorophosphite) are slowly added dropwise. After 5 hours of heating to 70-80, the reaction has ended. After filtration, the benzene is distilled off and the product of the formula is obtained
EMI0001.0029
as a pale yellow colored oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311478T | 1952-08-22 | ||
| CH308894T | 1952-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311478A true CH311478A (en) | 1955-11-30 |
Family
ID=25735533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311478D CH311478A (en) | 1952-08-22 | 1952-08-22 | Process for producing an organic phosphorus compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311478A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8466096B2 (en) | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
-
1952
- 1952-08-22 CH CH311478D patent/CH311478A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8466096B2 (en) | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
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