CH300840A - 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
CH300840A
CH300840A CH300840DA CH300840A CH 300840 A CH300840 A CH 300840A CH 300840D A CH300840D A CH 300840DA CH 300840 A CH300840 A CH 300840A
Authority
CH
Switzerland
Prior art keywords
halogen
preparation
organic compound
compound containing
containing phosphorus
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy filed Critical Ciba Geigy
Publication of CH300840A publication Critical patent/CH300840A/en

Links

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 System
    • 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, i.e. RP(=X)(XH)2 (X = S, 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  
EMI0001.0007     
    gelangt,     wenn    man     11Vfol        Triäthylphosphit    mit  1     Mol        Trichloressigsäure-(ss-chloräthyl)-ester     umsetzt. Die neue     Verbindung        ist    ein hoch  siedendes Öl und kann als 'Schädlingsbekämp  fungsmittel verwendet werden.

   Sie besitzt  neben einer     guten        kontaktinsektieiden    auch  eine ausgesprochene     innertherapeutische,    so  genannte     sy        stemische        Wirkung.     



  Die erfindungsgemässe Kondensation er  folgt durch     Umsetzung    der Komponenten     in     molekularem Verhältnis unter Abspaltung von  1.     Mol        Äthylehlorid.    Die Reaktion verläuft       exotherm,    so dass die Komponenten zweck  mässig unter Kühlung und mit     inerten    Lö  sungsmitteln, wie Benzol,     Toluol,    Äther,     Di-          oxan,        Hexan    oder tiefsiedendem Benzin, ver  dünnt     vereinigt    werden. Zur Beendigung der       Umsetzung    wird die Reaktionsmischung vor  teilhaft auf 80 bis 120  erwärmt.

    



  <I>Beispiel:</I>  Zu einer Lösung von 386 Teilen     Trichlor-          essigsäure-(ss-chloräthyl)-ester    in 600 Volum-    teilen Benzol werden nach und nach 332 Teile       Triäthylphosphit    zugegeben, wobei die Reak  tion durch schwaches Kühlen gemildert wird.  Nach     Beendigung    der Zugabe wird die Mi  schung während 3     Stunden    unter     Rückfluss     erhitzt. Anschliessend     wird    das Benzol ab  destilliert und der Rückstand im Hochvakuum  fraktioniert. Man erhält 450 Teile eines farb  losen     Öls,    das bei 125 bis 130 l0,1 mm     siedet.  



      Process for the preparation of an organic compound containing phosphorus and halogen. It has been found that the new phosphorus and halogen-containing compound of the formula
EMI0001.0007
    obtained when 11Vfol triethyl phosphite is reacted with 1 mol of trichloroacetic acid (s-chloroethyl) ester. The new compound is a high boiling oil and can be used as a pesticide.

   In addition to good contact insecticides, it also has a pronounced internal therapeutic, so-called systemic effect.



  The inventive condensation he follows by reacting 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. To complete the reaction, the reaction mixture is heated to 80 to 120 before some.

    



  <I> Example: </I> 332 parts of triethyl phosphite are gradually added to a solution of 386 parts of trichloroacetic acid (ss-chloroethyl) ester in 600 parts by volume of benzene, the reaction being alleviated by gentle cooling . After the addition is complete, the mixture is refluxed for 3 hours. The benzene is then distilled off and the residue is fractionated in a high vacuum. 450 parts of a colorless oil are obtained which boil at 125 to 130 l0.1 mm.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung der neuen Phos phor und Halogen enthaltenden Verbindung der Formel EMI0001.0045 dadurch gekennzeichnet, dass man 1 Mol Tri-- äthylphosphit mit 1 Mol Trichloressigsäure-(ss- chloräthyl)-ester umsetzt. Die neue Verbindung ist ein hochsiedendes < >l und kann als Schädlingsbekämpfungsmittel verwendet werden. PATENT CLAIM: Process for the preparation of the new phosphorus and halogen-containing compound of the formula EMI0001.0045 characterized in that 1 mole of tri-ethyl phosphite is reacted with 1 mole of trichloroacetic acid (s-chloroethyl) ester. The new compound is a high-boiling oil and can be used as a pesticide. UNTERANSPRUCH; Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in Gegenwart von inerten Lösungsmitteln vor nimmt. SUBCLAIM; Process according to claim, characterized in that the reaction is carried out in the presence of inert solvents.
CH300840D 1951-09-25 1951-09-25 Process for the preparation of an organic compound containing phosphorus and halogen. CH300840A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH300840T 1951-09-25

Publications (1)

Publication Number Publication Date
CH300840A true CH300840A (en) 1954-08-31

Family

ID=4490827

Family Applications (1)

Application Number Title Priority Date Filing Date
CH300840D CH300840A (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) CH300840A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228109A (en) * 1978-08-01 1980-10-14 E. I. Du Pont De Nemours And Company 1-Alkyl-2,2-dichloro-2(phosphinyl)acetates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4228109A (en) * 1978-08-01 1980-10-14 E. I. Du Pont De Nemours And Company 1-Alkyl-2,2-dichloro-2(phosphinyl)acetates

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