CH243273A - Process for the production of a trichlorovinyl ketone. - Google Patents
Process for the production of a trichlorovinyl ketone.Info
- Publication number
- CH243273A CH243273A CH243273DA CH243273A CH 243273 A CH243273 A CH 243273A CH 243273D A CH243273D A CH 243273DA CH 243273 A CH243273 A CH 243273A
- Authority
- CH
- Switzerland
- Prior art keywords
- ketone
- trichlorovinyl
- production
- naphthalene
- act
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- MQGVZPCVUTWNMB-UHFFFAOYSA-N 1,1,2,4,5,5-hexachloropenta-1,4-dien-3-one Chemical compound ClC(Cl)=C(Cl)C(=O)C(Cl)=C(Cl)Cl MQGVZPCVUTWNMB-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 trichloroacrylic acid halide Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- BCOSEZGCLGPUSL-UHFFFAOYSA-N 2,3,3-trichloroprop-2-enoyl chloride Chemical compound ClC(Cl)=C(Cl)C(Cl)=O BCOSEZGCLGPUSL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910008046 SnC14 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Trichlor vinylketons. Es wurde gefunden, dass Trichlorvinyl- ketone der allgemeinen Formel
EMI0001.0006
sich durch ihre Giftigkeit gegenüber Insekten und deren Entwicklungsstadien auszeichnen.
In dieser Formel bedeutet R' einen auellierten oder direkt oder über NH, C0, CHz, 0 oder S gebundenen, isocyclischen Ring oder Ring verband, wobei sowohl R als auch R' substi- tuiert oder unsubstituiert sein können.
Zur Darstellung der oben definierten Ke- tone lässt man Tricbloracrylsäurehalogenide auf Verbindungen der allgemeinen Formel
EMI0001.0022
worin R' und R obiger Definition entspre chen, in Gegenwart von Katalysatoren, wie AICl3, FeCl3, SnC14 usw., einwirken. Vorteil haft arbeitet man in Verdünnungsmitteln, wie Schwefelkohlenstoff, Nitrobenzol usw.
Als Verbindungen der Formel
EMI0001.0032
kommen beispielsweise in Frage:
EMI0002.0001
Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Trichlor- vinylketons. Das Verfahren ist dadurch ge kennzeichnet, dass man auf Naphthalin ein Trichloracrylsäurehalogenid in Gegenwart eines Kondensationsmittels einwirken lässt.
Das entstandene Gemisch von a- und ss-Naph- thyl-trichlorvinylketon siedet bei 155-156 unter 0,6 mm Druck. Das Gemisch der a- und ss-Komponenten der neuen Verbindung soll als Insektizid Verwendung finden. Beispiel: Man löst 200 Teile Naphthalin in 600 Tei len trockenem Schwefelkohlenstoff und gibt dann 150 Teile Aluminiumchlorid zu. Unter gutem Rühren tropft man 194 Teile Tri- ehloracrylsäuTechlorid zu.
Nach beendigter Zugabe rührt man noch 2 Stunden bei Zim mertemperatur weiter und erwärmt anschlie ssend 2 Stunden zum Sieden. Die Reaktions mischung wird nach dem Abkühlen auf Eis gegossen und die Schwefelkohlenstofflösung abgetrennt. Man wäscht mit verdünnter Salz säure und Sodalösung und anschliessend mit Wasser.
Nach dem Trocknen und Abdestillie- ren des Lösungsmittels wird der Rückstand im Hochvakuum fraktioniert. Man erhält das Naphthyl-triehlorvinylketon als ein Gemisch der a- und ss-Isomeren vom Siedepunkt 155 bis 156 unter 0,6 mm Druck.
Process for the preparation of a trichloro vinyl ketone. It was found that trichlorovinyl ketones of the general formula
EMI0001.0006
are characterized by their toxicity to insects and their stages of development.
In this formula, R 'denotes an isocyclic ring or ring bonded or bonded directly or via NH, C0, CH2, O or S, where both R and R' can be substituted or unsubstituted.
To prepare the ketones defined above, tricbloroacrylic acid halides are allowed to form on compounds of the general formula
EMI0001.0022
where R 'and R correspond to the above definition, in the presence of catalysts such as AlCl3, FeCl3, SnC14, etc., act. It is advantageous to work in diluents such as carbon disulfide, nitrobenzene, etc.
As compounds of the formula
EMI0001.0032
for example:
EMI0002.0001
The present patent is a process for the preparation of a trichloro vinyl ketone. The process is characterized in that a trichloroacrylic acid halide is allowed to act on naphthalene in the presence of a condensing agent.
The resulting mixture of α- and β-naphthyl-trichlorovinyl ketone boils at 155-156 under 0.6 mm pressure. The mixture of the a and ss components of the new compound is said to be used as an insecticide. Example: 200 parts of naphthalene are dissolved in 600 parts of dry carbon disulfide and then 150 parts of aluminum chloride are added. 194 parts of tri-chloroacrylic acid chloride are added dropwise with thorough stirring.
When the addition is complete, the mixture is stirred for a further 2 hours at room temperature and then heated to boiling for 2 hours. After cooling, the reaction mixture is poured onto ice and the carbon disulfide solution is separated off. It is washed with dilute hydrochloric acid and soda solution and then with water.
After drying and distilling off the solvent, the residue is fractionated in a high vacuum. The naphthyl triehlorvinyl ketone is obtained as a mixture of the α and β isomers with a boiling point of 155 to 156 under 0.6 mm pressure.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH243273T | 1944-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH243273A true CH243273A (en) | 1946-07-15 |
Family
ID=4463450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH243273D CH243273A (en) | 1944-10-30 | 1944-10-30 | Process for the production of a trichlorovinyl ketone. |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE460997A (en) |
| CH (1) | CH243273A (en) |
-
0
- BE BE460997D patent/BE460997A/xx unknown
-
1944
- 1944-10-30 CH CH243273D patent/CH243273A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE460997A (en) |
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