CH310405A - Process for the preparation of an organic compound containing phosphorus and halogen. - Google Patents
Process for the preparation of an organic compound containing phosphorus and halogen.Info
- Publication number
- CH310405A CH310405A CH310405DA CH310405A CH 310405 A CH310405 A CH 310405A CH 310405D A CH310405D A CH 310405DA CH 310405 A CH310405 A CH 310405A
- Authority
- CH
- Switzerland
- Prior art keywords
- halogen
- preparation
- organic compound
- compound containing
- containing phosphorus
- Prior art date
Links
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 4
- 229910052736 halogen Inorganic materials 0.000 title claims description 4
- 150000002367 halogens Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 4
- 239000011574 phosphorus Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 3
- OXVISHZELPRKFQ-UHFFFAOYSA-N 2,2,3-trichlorobutanal Chemical compound CC(Cl)C(Cl)(Cl)C=O OXVISHZELPRKFQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000010438 heat treatment Methods 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
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 Phosphor und Halogen enthaltenden organischen Verbindung. Es wurde gefunden, dass man zu der neuen. Phosphor und Halogen enthaltenden Verbin dung der Formel
EMI0001.0002
gelangt, wenn man 1 Mol Triäthylphosphit mit 1 Mol Butylchloral umsetzt. Die neue Ver bindung ist ein hochsiedendes Öl und kann als Schädlingsbekämpfungsmittel verwendet wer den.
Die erfindungsgemässe Kondensation er folgt dureh Umsetzung der Komponenten in molekularem Verhältnis unter Abspaltung von 1. Mol Äthylchlorid. Die Reaktion verläuft exo- therm, so dass die Komponenten zweckmässig unter Kühlung und mit inerten Lösungsmit teln, wie Benzol, Toluol, Äther, Dioxan, Hexan oder tiefsiedendem Benzin, verdünnt vereinigt werden.
Zur Beendigung der Umsetzung wird die Reaktionsmischung vorteilhaft auf 80 bis 120 erwärmt.
<I>Beispiel:</I> Zu einer Lösung von 5,8 Teilen Butylchlo- ral der Formel OHC - CCl2. CHCI - CH3 in 20 Volumteilen Benzol wird unter Rühren bei 20-30 eine solche von 6 Teilen Triäthyl- phosphit in 5 Vohimteilen Benzol zugetropft. Hierauf lässt man die Reaktionsmischung wäh rend 30 Minuten bei Raiuntemperatur und während 1 Stunde bei 60-70 ohne Rühren stehen.
Nach dem Abdestillieren des Benzols und Erhitzen des Rückstandes bei 90-100 im Vakuum von 12 mm zur Entfernung von leichtflüchtigen Bestandteilen erhält man 9,0 Teile des Kondensationsproduktes als gelblich gefärbtes Öl.
Process for the preparation of an organic compound containing phosphorus and halogen. It was found that one to the new. Phosphorus and halogen-containing compound of the formula
EMI0001.0002
obtained when 1 mol of triethyl phosphite is reacted with 1 mol of butyl chloral. The new compound is a high-boiling oil and can be used as a pesticide.
The inventive condensation he follows dureh implementation of the components in a molecular ratio with elimination of 1 mole of ethyl chloride. The reaction is exothermic, so that the components are advantageously combined with cooling and diluted with inert solvents such as benzene, toluene, ether, dioxane, hexane or low-boiling gasoline.
The reaction mixture is advantageously heated to 80 to 120 to terminate the reaction.
<I> Example: </I> To a solution of 5.8 parts of butyl chloride of the formula OHC - CCl2. CHCI - CH3 in 20 parts by volume of benzene is added dropwise with stirring at 20-30% of 6 parts of triethyl phosphite in 5 parts by volume of benzene. The reaction mixture is then left to stand without stirring for 30 minutes at room temperature and for 1 hour at 60-70.
After distilling off the benzene and heating the residue at 90-100 in a vacuum of 12 mm to remove volatile constituents, 9.0 parts of the condensation product are obtained as a yellowish oil.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH300840T | 1951-09-25 | ||
| CH310405T | 1951-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310405A true CH310405A (en) | 1955-10-15 |
Family
ID=25734295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310405D CH310405A (en) | 1951-09-25 | 1951-09-25 | Process for the preparation of an organic compound containing phosphorus and halogen. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310405A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020623B (en) * | 1956-05-29 | 1957-12-12 | Boehringer Sohn Ingelheim | Process for the preparation of insecticidally active phosphonic acid esters |
-
1951
- 1951-09-25 CH CH310405D patent/CH310405A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020623B (en) * | 1956-05-29 | 1957-12-12 | Boehringer Sohn Ingelheim | Process for the preparation of insecticidally active phosphonic acid esters |
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