DE1568634A1 - Process for the production of organophosphorus sulfene chlorides - Google Patents
Process for the production of organophosphorus sulfene chloridesInfo
- Publication number
- DE1568634A1 DE1568634A1 DE19661568634 DE1568634A DE1568634A1 DE 1568634 A1 DE1568634 A1 DE 1568634A1 DE 19661568634 DE19661568634 DE 19661568634 DE 1568634 A DE1568634 A DE 1568634A DE 1568634 A1 DE1568634 A1 DE 1568634A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorides
- organophosphorus
- sulfene
- production
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 sulfene chlorides Chemical class 0.000 title description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
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 phosphororganischer Sulfenchloride Es wurde gefunden, daß man neuartige phosphororganische Sulfenchloride erhält, wenn man Trihalogenmethansulfenchloride der Formel F3, ClnC-S-Cl in welcher n eine ganze Zahl von 1 bis 3 bedeutet, vorzugsweise in Gegenwart eines inerten organischen VerdRanungsmittels bei Temperaturen zwischen etwa 50 und etwa 2000t'. mit Phosphorpentasulfid umsetzt und die gebildete Verbindung der Formel worin n die obengenannte Bedeutung besitzt, isoliert.Process for the preparation of organophosphorus sulfene chlorides It has been found that novel organophosphorus sulfene chlorides are obtained if trihalomethanesulfene chlorides of the formula F3, ClnC-S-Cl in which n is an integer from 1 to 3, preferably in the presence of an inert organic diluent at temperatures between about 50 and about 2000t '. reacts with phosphorus pentasulfide and the resulting compound of the formula wherein n has the abovementioned meaning, isolated.
Die für das erfindungsgemäße Verfahren Verwendung findenden Ausgangsverbindungen sind bekannt.The starting compounds used for the process according to the invention are known.
Die Umsetzung wird vorzugsweise in Anwesenheit eines inerten organischen Verdünnungsmittels durchgeführt. Dabei werden insbesondere Lösungsmittel verwendet, die mit den Auagangssubstanzen nicht oder nur langsam reagieren. Als derartige Lösungsmittel seien beispielsweise genannt : Benzol, Toluol, Chlorbenzol, Dichlorbenzol.The reaction is preferably carried out in the presence of an inert organic Diluent carried out. Solvents are used in particular, which do not react or react only slowly with the outlet substances. As such a solvent examples include: benzene, toluene, chlorobenzene, dichlorobenzene.
Die Reaktionstemperatur kann in einem weiten Bereich variiert werden. Im allgemeinen arbeitet man zwischen etwa 50 und etwa 2000 C, vorzugsweise zwischen 120 und 1500 C.The reaction temperature can be varied within a wide range. In general, between about 50 and about 2000 C, preferably between 120 and 1500 C.
Im allgemeinen wird so gearbeitet, caß man eine Lösung von 3 Mol des Sulfenchlorids im entsprechenden Lösungsmittel mii etwa 1 Mol Phosphorpentasulfid versetzt und die Mischung solange zum Sieden erhitzt, bis eine weitgehend klare Lösung vorliegt. Gegebenenfalls kann es verteilhaft sein, einen Überschuß an Phosphorpentasulfid bis zu etwa 50%, vorzugsweise 10 - 20% zu verwenden. Nach Abdestillieren des Lösungsmittels fallen die neuen Verbindungen als destillierbare Flüssigkeiten an.In general, the procedure is such that a solution of 3 mol of des Sulfenchloride in the appropriate solvent with about 1 mole of phosphorus pentasulfide added and the mixture heated to the boil until a largely clear Solution is available. It may be advisable to use an excess of phosphorus pentasulphide up to about 50%, preferably 10-20% to be used. After distilling off the solvent the new compounds are obtained as distillable liquids.
Die erfindungsgemäß erhältlichen neuen phosphororganischen Sulfenchloride sind wertvolle Zwisotenprodukte zur Zerstellung von Pflanzenschutzmitteln.The new organophosphorus sulfene chlorides obtainable according to the invention are valuable two-way products for the preparation of pesticides.
Beispiel Ein Gemisch vt;n 51 g Fluordichlormethansulfenchlorid (0,3 Mol) und 22 g Phosphorpentasulfid (0,1 Mol) in 200 ccm Chlorbenzol wird unter Rückfluß erhitzt, bis eine weitgehend klare Lösung vorliegt ( ca. 1 Stunde). Man rührt bei Suedetemperatur noch 10 Minuten nach, läßt abkühlen und filtriert. Nach Entfernung des Lösungsmittels wird der Rückstand im Vakuum destilliert. Man erhält 26 g Chlor-(fluoriddichlormethylmercapto) -thiophosphoryl-sulfenylchlorid der Formel Kp.: 66 - 68°C / 0,12 Torr; nD20 1,6199.EXAMPLE A mixture of 51 g of fluorodichloromethanesulfen chloride (0.3 mol) and 22 g of phosphorus pentasulphide (0.1 mol) in 200 cc of chlorobenzene is refluxed until a largely clear solution is obtained (approx. 1 hour). The mixture is stirred at south temperature for a further 10 minutes, allowed to cool and filtered. After the solvent has been removed, the residue is distilled in vacuo. 26 g of chlorine (fluoride dichloromethyl mercapto) thiophosphoryl sulfenyl chloride of the formula are obtained B.p .: 66-68 ° C / 0.12 torr; nD20 1.6199.
Analog wird erhalten: Kp. : 108 - 109°C/0,2 Torr.The following is obtained analogously: Bp: 108-109 ° C / 0.2 Torr.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050854 | 1966-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1568634A1 true DE1568634A1 (en) | 1970-03-05 |
Family
ID=7104127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568634 Pending DE1568634A1 (en) | 1966-12-06 | 1966-12-06 | Process for the production of organophosphorus sulfene chlorides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1568634A1 (en) |
-
1966
- 1966-12-06 DE DE19661568634 patent/DE1568634A1/en active Pending
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