CH344407A - Process for the preparation of a new chlorine-containing compound - Google Patents
Process for the preparation of a new chlorine-containing compoundInfo
- Publication number
- CH344407A CH344407A CH344407DA CH344407A CH 344407 A CH344407 A CH 344407A CH 344407D A CH344407D A CH 344407DA CH 344407 A CH344407 A CH 344407A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- containing compound
- new
- new chlorine
- chlorine
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Description
Verfahren zur Herstellung einer neuen chlorhaltigen Verbindung
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung der neuen chlorhaltigen Verbindung 1, 4,5,6,7,7-Hexachlor-2-chlorformyl-bicyclo (2.2.1)-5-hepten, indem man Hexachlorcyclopentadien als Dienkomponente mit Acrylsäurechlo- rid als dienophiler Komponente umsetzt.
Die Umsetzung erfolgt gemäss folgender Reaktionsgleichung
EMI1.1
Die neue Verbindung ist ein Säurechlorid und reagiert leicht mit primären oder sekundären Aminen, Alkoholen, Phosphiten oder Phosphaten bzw. Thiophosphaten unter Bildung der entsprechenden Amide, Ester, Phosphonate, Phosphate bzw. Thiophosphate.
Diese Produkte eignen sich u. a. als Flammschutzmittel, Schmierölzusätze, Weichmacher für Lacke und Kunststoffe, Insektizide, Fungizide usw.
Setzt man das neue Säurechlorid mit Alkoholen oder Aminen um, die äthylenisch ungesättigte Doppelbindungen enthalten, so gelangt man zu monomeren Derivaten, die direkt oder in Form ihrer Polymerisate als Textilhilfsmittel dienen können.
Durch Amidierung, Veresterung, Phosphonierung oder Phosphorylierung kann man beispielsweise folgende Verbindungen erhalten :
EMI1.2
EMI2.1
fest--fest F = 74 fest--fest F = 99 Cl : 45,3 /o, 45,4 I/o (bzw. 45,7"/.) nicht destillierbare Flüssigkeit
Ausser als Zwischenprodukt kann das neue Säure- chlorid auch direkt zur Behandlung von basischen stickstoffhaltigen Fasern wie Wolle verwendet werden, um dieselben flammfest oder mottenecht zu machen.
Beispiel
In einem Dreihalskolben mit Rührer, Thermometer und Rückflusskühler wird eine Mischung von 136,5 g Hexachlorcyclopentadien und 45,5 g Acrylsäurechlorid auf dem Ölbad zum Sieden erhitzt. Die Temperatur beträgt zuerst 85 C und steigt sodann langsam nach zweistündigem Erhitzen am Rückfluss auf 135 C. In diesem Zeitpunkt hat das Sieden aufgehört, und die Reaktion ist praktisch beendet. Man hält die Temperatur noch während einer Stunde auf 135 C, lässt dann abkühlen und fraktioniert das Produkt im Hochvakuum. Man erhält 171 g einer farblosen Flüssigkeit von leicht stechendem Geruch, die bei 105 C/0, lmm siedet. Die Ausbeute beträgt 94"/o.
Die Analyse ergibt einen Chlorgehalt von 68,25 /o gegenüber einem berechneten Chlorgehalt von 68,35 Prozent.
Process for the preparation of a new chlorine-containing compound
The present invention relates to a process for the preparation of the new chlorine-containing compound 1, 4,5,6,7,7-hexachloro-2-chloroformyl-bicyclo (2.2.1) -5-heptene by using hexachlorocyclopentadiene as the diene component with acrylic acid chloride Ride implemented as a dienophilic component.
The reaction takes place according to the following reaction equation
EMI1.1
The new compound is an acid chloride and reacts easily with primary or secondary amines, alcohols, phosphites or phosphates or thiophosphates to form the corresponding amides, esters, phosphonates, phosphates or thiophosphates.
These products are suitable a. as flame retardants, lubricating oil additives, plasticizers for paints and plastics, insecticides, fungicides, etc.
If the new acid chloride is reacted with alcohols or amines which contain ethylenically unsaturated double bonds, monomeric derivatives are obtained which can serve as textile auxiliaries directly or in the form of their polymers.
The following compounds, for example, can be obtained by amidation, esterification, phosphonation or phosphorylation:
EMI1.2
EMI2.1
solid - solid F = 74 solid - solid F = 99 Cl: 45.3 / o, 45.4 I / o (or 45.7 "/.) non-distillable liquid
In addition to being an intermediate product, the new acid chloride can also be used directly to treat basic nitrogen-containing fibers such as wool in order to make them flame-proof or moth-proof.
example
In a three-necked flask equipped with a stirrer, thermometer and reflux condenser, a mixture of 136.5 g of hexachlorocyclopentadiene and 45.5 g of acrylic acid chloride is heated to the boil on an oil bath. The temperature is first 85 ° C. and then slowly rises to 135 ° C. after refluxing for two hours. At this point, the boiling has stopped and the reaction is practically complete. The temperature is kept at 135 ° C. for a further hour, then allowed to cool and the product is fractionated in a high vacuum. 171 g of a colorless liquid with a slightly pungent odor which boils at 105 ° C./0.1 mm are obtained. The yield is 94 "/ o.
The analysis shows a chlorine content of 68.25 / o compared to a calculated chlorine content of 68.35 percent.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH344407T | 1956-10-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH344407A true CH344407A (en) | 1960-02-15 |
Family
ID=4506914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH344407D CH344407A (en) | 1956-10-25 | 1956-10-25 | Process for the preparation of a new chlorine-containing compound |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH344407A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4082795A (en) * | 1975-08-29 | 1978-04-04 | Ciba-Geigy Corporation | Perfluoroalkylthio norbornane compounds |
-
1956
- 1956-10-25 CH CH344407D patent/CH344407A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4082795A (en) * | 1975-08-29 | 1978-04-04 | Ciba-Geigy Corporation | Perfluoroalkylthio norbornane compounds |
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