DE801330C - Process for the production of halogen-containing unsaturated amines - Google Patents

Process for the production of halogen-containing unsaturated amines

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Publication number
DE801330C
DE801330C DEP11847D DEP0011847D DE801330C DE 801330 C DE801330 C DE 801330C DE P11847 D DEP11847 D DE P11847D DE P0011847 D DEP0011847 D DE P0011847D DE 801330 C DE801330 C DE 801330C
Authority
DE
Germany
Prior art keywords
halogen
production
containing unsaturated
amines
unsaturated amines
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
DEP11847D
Other languages
German (de)
Inventor
Friedrich Dr Becke
Georg Dr Hummel
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to DEP11847D priority Critical patent/DE801330C/en
Application granted granted Critical
Publication of DE801330C publication Critical patent/DE801330C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy 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

(WiGBl. S. 175)(WiGBl. P. 175)

AUSGEGEBEN AM 4. JANUAR 1951ISSUED JANUARY 4, 1951

p 11847 IV d j 12 ο Dp 11847 IV d j 12 ο D

in Ludwigshafen, Rheinin Ludwigshafen, Rhine

Es wurde gefunden, daß man in einfacher Weise und mit guter Ausbeute halogenhaltige ungesättigte Amine erhält, wenn man organische Halogenverbindungen, die Halogenatome an mindestens drei gesättigten Kohlenstoffatomen und davon mindestens zwei an benachbarten Kohlenstoffatomen enthalten, mit Ammoniak oder mit primären oder sekundären Aminen bei erhöhter Temperatur umsetzt.It has been found that halogen-containing unsaturated compounds can be obtained in a simple manner and with good yield Amines are obtained when organic halogen compounds have at least three saturated halogen atoms Contain carbon atoms and at least two of them on adjacent carbon atoms, with ammonia or with primary or secondary amines at elevated temperature.

Geeignete organische Halogenverbindungen sind z. B. das ι · ζ ■ 3-Trichlorpropan, das 1-2-3-, und das 1 · 2 ■ 4-Trichloi'butan und das 1 · 2 · 3 · 4-Tetrachlorbutan. Als Amine eignen sich z. B. Methyl-, Äthyl-, Cyclohexyl- oder Stearylamin, Dimethyl- oder Methyläthylamin, Anilin oder Monomethylamin!. Man verwendet die Amine zweckmäßig in flüssiger Form, gewünschtenfalls in einem indifferenten Losungsmittel. Suitable organic halogen compounds are, for. B. the ι · ζ ■ 3-trichloropropane, the 1-2-3, an d the 1 × 2 ■ 4-Trichloi'butan and the 1 x 2 x 3 x 4-tetrachlorobutane. Suitable amines are, for. B. methyl, ethyl, cyclohexyl or stearylamine, dimethyl or methylethylamine, aniline or monomethylamine !. The amines are expediently used in liquid form, if desired in an inert solvent.

Die Umsetzung erfolgt bei erhöhter Temperatur, erforderlichenfalls unter Druck. Die günstigsten Arbeitsbedingungen sind von Fall zu Fall verschieden; sie lassen sich durch Vorversuche leicht ermitteln. In manchen Fällen ist die Mitverwendung von Katalysatoren, wie Kupfer oder seinen Oxyden und Halogeniden, zweckmäßig.The reaction takes place at elevated temperature, if necessary under pressure. The most favorable working conditions vary from case to case; they can easily be determined by preliminary tests. In In some cases, the use of catalysts, such as copper or its oxides and halides, expedient.

Im Falle der Umsetzung von 1 · 2 · 3-Trichlorpropan mit Ammoniak ergibt sich folgendes Reaktionsschema:In the case of the reaction of 1 · 2 · 3-trichloropropane with ammonia, the following reaction scheme results:

Cl-CH2-CHCl- CH2Cl + 3 NH3-> CH2 = C-CH2-NH2+2 NH4Cl.Cl-CH 2 -CHCl- CH 2 Cl + 3 NH 3 -> CH 2 = C-CH 2 -NH 2 +2 NH 4 Cl.

Neben dem primären Amin bilden sich stets mehr oder weniger große Mengen des entsprechenden sekundären und tertiären Amins, also im obigen Fall neben dem /J-Chlorallylamin auch das Di-^-chlorallyl-) und das Tri-(/J-chlorallyl-)amin.In addition to the primary amine, more and more are always formed or less large amounts of the corresponding secondary and tertiary amine, so in the above case in addition the / J-chlorallylamine also the di - ^ - chlorallyl-) and the tri (/ J-chlorallyl) amine.

Die nach dem geschilderten Verfahren leicht zugänglichen halogenhaltigen ungesättigten Amine haben z.T. erhebliche insektizide Wirksamkeit. Sie sind außerdem wertvolle Zwischenprodukte, insbesondere für ίο Textilhilfsmittel und Pharmazeutika.The halogen-containing unsaturated amines which are easily accessible by the process described have partly considerable insecticidal effectiveness. They are also valuable intermediates, especially for ίο textile auxiliaries and pharmaceuticals.

Die im Beispiel genannten Teile sind Gewichtsteile.The parts mentioned in the example are parts by weight.

Beispielexample

Man erhitzt in einem Rührautoklaven 1500 Teile ι · 2 · 3-Trichlorpropan (hergestellt aus Allylchlorid und Chlor) mit 1500 Teilen flüssigem Ammoniak 3 Stunden auf ioo°. Die erhaltene halbfeste, braune Masse wird mit einem Lösungsmittel, wie Äther oder Methanol, behandelt, das das Ammoniumchlorid ungelöst läßt. Die abfiltrierte Lösung wird mit Ätzkali getrocknet ao und dann eingedampft. Es hinterbleiben 770 g einer leicht beweglichen, braunen Flüssigkeit von starkem Amingeruch. Sie läßt sich durch fraktionierte Destillation in /8-Chlorallylamin vom Siedepunkt 106 bis 107 ° (bei gewöhnlichem Druck) und Di- (ß-chlorallyl-) amin vom Siedepunkt 62 bis 64° (bei 2 mm Druck) zerlegen.1500 parts of ι · 2 · 3-trichloropropane (made from allyl chloride and Chlorine) with 1500 parts of liquid ammonia for 3 hours at 100 °. The semi-solid, brown mass obtained is treated with a solvent such as ether or methanol which leaves the ammonium chloride undissolved. The filtered solution is dried ao with caustic potash and then evaporated. There remains 770 g of one easily mobile, brown liquid with a strong amine odor. You can by fractional distillation in / 8-chloroallylamine from a boiling point of 106 to 107 ° (at ordinary pressure) and di (ß-chlorallyl) amine decompose from boiling point 62 to 64 ° (at 2 mm pressure).

Claims (1)

Patenta N sp R uc H.Verfahren zur Herstellung halogenhaltiger ungesättigter Amine, dadurch gekennzeichnet, daß man organische Halogenverbindungen, die Halogenatome an mindestens drei gesättigten Kohlenstoffatomen und davon mindestens zwei an benachbarten Kohlenstoffatomen enthalten, mit Ammoniak oder mit primären oder sekundären Aminen bei erhöhter Temperatur umsetzt.Patenta N sp R uc H. Process for the production of halogen-containing unsaturated Amines, characterized in that one organic halogen compounds, the halogen atoms on at least three saturated carbon atoms and at least two of them on adjacent ones Containing carbon atoms, with ammonia or with primary or secondary amines at elevated levels Temperature converts. © 30S0 12.50© 30S0 12.50
DEP11847D 1948-10-02 1948-10-02 Process for the production of halogen-containing unsaturated amines Expired DE801330C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEP11847D DE801330C (en) 1948-10-02 1948-10-02 Process for the production of halogen-containing unsaturated amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEP11847D DE801330C (en) 1948-10-02 1948-10-02 Process for the production of halogen-containing unsaturated amines

Publications (1)

Publication Number Publication Date
DE801330C true DE801330C (en) 1951-01-04

Family

ID=7363714

Family Applications (1)

Application Number Title Priority Date Filing Date
DEP11847D Expired DE801330C (en) 1948-10-02 1948-10-02 Process for the production of halogen-containing unsaturated amines

Country Status (1)

Country Link
DE (1) DE801330C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960191C (en) * 1953-09-22 1957-03-21 Huels Chemische Werke Ag Process for the production of nitrogen-containing vinyl ethers

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE960191C (en) * 1953-09-22 1957-03-21 Huels Chemische Werke Ag Process for the production of nitrogen-containing vinyl ethers

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