DE739533C - Process for the production of organic chloronitro compounds - Google Patents

Process for the production of organic chloronitro compounds

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Publication number
DE739533C
DE739533C DER107983D DER0107983D DE739533C DE 739533 C DE739533 C DE 739533C DE R107983 D DER107983 D DE R107983D DE R0107983 D DER0107983 D DE R0107983D DE 739533 C DE739533 C DE 739533C
Authority
DE
Germany
Prior art keywords
organic
production
compounds
chloronitro
chloronitro compounds
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.)
Expired
Application number
DER107983D
Other languages
German (de)
Inventor
Dipl-Ing Manfred Kuehnel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DER107983D priority Critical patent/DE739533C/en
Application granted granted Critical
Publication of DE739533C publication Critical patent/DE739533C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von organischen Chlornitroverhindungen Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von _o@rganischen Chlornitroverbindungen, indem man Nitrylchlorid auf ungesättigte organische Verbindungen einwirken läßt. Die Anlagerung verläuft schon in der Kälte mit hinreichender Geschwindigkeit, sie kann aber durch Arbeiten bei höherer Temperatur im Einschlußrohr bedeutend beschleunigt werden. In manchen Fällen ist es jedoch zweckmäßig, mit Verdünnungsmitteln zu arbeiten, da unter Umständen schon in der Kälte explosionsartige Umsetzung eintreten kann.Process for the production of organic chloronitro compounds subject the present invention is a process for the preparation of organic chloronitro compounds, by allowing nitryl chloride to act on unsaturated organic compounds. The accumulation proceeds with sufficient speed even in the cold, they but can be significantly accelerated by working at a higher temperature in the containment tube will. In some cases, however, it is advisable to work with thinners, because under certain circumstances explosive conversion can occur even in the cold.

Nach der Umsetzung läßt sich ein kleiner Überschuß an N itrylchlorid durch Abdunsten entfernen. Danach wird das Reaktionsprodukt durch Destillation gereinigt. 13 g Trichloräthylen und io g Nitrylchlorid werden unter Tiefkühlung im Bombenrohr zusammengegeben. Man erhitzt längere Zeit auf ioo°. Nach völligem Abkühlen ist im Rohr nur noch geringer Überdruck. Die Flüssigkeit wird nach Abdunsten überschüssigen Nitrylchlorids im Vakuum destilliert. Zunächst geht ein kleiner Teil nicht umge setzten Trichloräthylen.s, dann Idas Tetrachlornitro,äthan bei 74 bis 76 ° (i8 mm) über. Ausbeute 15 g = 70°o d. Th.After the reaction, a small excess of nitryl chloride can be removed by evaporation. The reaction product is then purified by distillation. 13 g of trichlorethylene and 10 g of nitryl chloride are combined in a sealed tube with freezing. It is heated to 100 ° for a long time. After it has completely cooled down, there is only a slight overpressure in the pipe. After the excess nitryl chloride has evaporated, the liquid is distilled in vacuo. At first a small part of unreacted trichlorethylene, then Ida's tetrachloronitro, ethane passes over at 74 to 76 ° (18 mm). Yield 15 g = 70 ° o d. Th.

Beispiel a Anlagerung von N 02 Cl an olefinische Doppelbindung in fettaromatischen Säuren: g Zimtsäure «.erden im Einschlußrohr mit 5-g N 02 Cl (verdünnt mit C C'4) 2 Std. auf etwa 850 erhitzt. Nach Abtreiben des Lösungsmittels wurde die gelbe Kristallmasse aus heißem Wasser umkristallisiert. Schmp. 162 bis 163'. Beispiel 3 Anlagerung von N O, Cl an Acetylenbindung: io g Phenylacetylen (in 2o g Äther gelöst) werden unter Kühlung mit 8.- N 02 Cl (in 2o g Äther gelöst) vermischt. Nach Absaugen des Äthers hinterbleibt das Monoadditionsprodukt als ein hellgelbes Öl, das sich alsbald zu einer zähen, dunkelroten Flüssigkeit polymerisiert. Bei der Destillation im Vakuum (12 mm) tritt Zersetzung ein.Example a Addition of N 02 Cl to an olefinic double bond in fatty aromatic acids: g of cinnamic acid are ground in the containment tube with 5 g of N 02 Cl (diluted with C C'4) heated to about 850 for 2 hours. After the solvent had been stripped off, the yellow crystal mass was recrystallized from hot water. M.p. 162 to 163 '. Example 3 Addition of NO, Cl to acetylene bond: 10 g phenylacetylene (dissolved in 20 g ether) are mixed with 8 N 02 Cl (dissolved in 20 g ether) while cooling. After the ether has been suctioned off, the monoaddition product remains as a light yellow oil, which soon polymerizes to a viscous, dark red liquid. Decomposition occurs during distillation in vacuo (12 mm).

Das Diadditionsprodukt wird in gleicher Weise erhalten. Man versetzt dazu das Phenylacetylen mit der doppelten Menge N itrylchlorid. Rotbraune Flüssigkeit, die sich ebenfalls nicht, unzersetzt destillieren läßt.The diaddition product is obtained in the same way. One relocates in addition the phenylacetylene with twice the amount of nitryl chloride. Red-brown liquid, which also cannot be distilled without decomposition.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von organischen Chlornitroverbindungen, dadurch gekennzeichnet, daß man Nitrylchlorid auf ungesättigte organische Verbindungen, gegebenenfalls unter Druck und erhöhter Temperatur, einwirken läßt.PATENT CLAIM: Process for the production of organic chloronitro compounds, characterized in that nitryl chloride is based on unsaturated organic compounds, optionally under pressure and elevated temperature, allowed to act.
DER107983D 1940-07-25 1940-07-25 Process for the production of organic chloronitro compounds Expired DE739533C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DER107983D DE739533C (en) 1940-07-25 1940-07-25 Process for the production of organic chloronitro compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DER107983D DE739533C (en) 1940-07-25 1940-07-25 Process for the production of organic chloronitro compounds

Publications (1)

Publication Number Publication Date
DE739533C true DE739533C (en) 1943-09-28

Family

ID=7421568

Family Applications (1)

Application Number Title Priority Date Filing Date
DER107983D Expired DE739533C (en) 1940-07-25 1940-07-25 Process for the production of organic chloronitro compounds

Country Status (1)

Country Link
DE (1) DE739533C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511915A (en) * 1950-06-20 Production of chloronitro

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2511915A (en) * 1950-06-20 Production of chloronitro

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