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DE947707C - Process for the preparation of aromatic di-tertiary diamines - Google Patents

Process for the preparation of aromatic di-tertiary diamines

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Publication number
DE947707C
DE947707C DEB32488A DEB0032488A DE947707C DE 947707 C DE947707 C DE 947707C DE B32488 A DEB32488 A DE B32488A DE B0032488 A DEB0032488 A DE B0032488A DE 947707 C DE947707 C DE 947707C
Authority
DE
Germany
Prior art keywords
parts
phosgene
diethylamino
ethyl
preparation
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
DEB32488A
Other languages
German (de)
Inventor
Dr Herbert Friederich
Dr Otto-Alfred Grosskinsky
Dr Heinz Mueller-Tamm
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 DEB32488A priority Critical patent/DE947707C/en
Application granted granted Critical
Publication of DE947707C publication Critical patent/DE947707C/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
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings

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

Description

Verfahren zur Herstellung von aromatischen di-tertiären Diaminen Zusatz zum Patent 939630 Das Patent 939 630 betrifft ein Verfahren zur Herstellung von heterocyclischen Verbindungen mit ringständiger Imilnogruppe, die durch basische Gruppen substituiert ist, bei dem man die durch Umsetzen der iminogruppenhaltigen Heterocyclen mit Phosgen und dann mit Aminoalkoholen erhältlichen Aminourethane oder ihre Hydrohalogenide auf Temperaturen zwischen etwa I50 und 2200 erhitzt.Process for the production of aromatic di-tertiary diamines additive to patent 939630 The patent 939 630 relates to a method for the production of heterocyclic compounds with an imilno group in the ring, which are replaced by basic Groups is substituted, in which one by reacting the imino-containing Heterocycles with phosgene and then aminourethanes obtainable with amino alcohols or their hydrohalides are heated to temperatures between about 150 and 2200.

Es wurde nun gefunden, daß sich in analoger Weise auch aromatische di-tertiäre Diamine in guter Ausbeute herstellen lassen, wenn man statt der heterocyclischen Amine sekundäre aromabische Amine verwendet. It has now been found that aromatic substances can also be produced in an analogous manner Di-tertiary diamines can be produced in good yield if, instead of the heterocyclic Amines used secondary aromatic amines.

Geeignete sekundäre aromatische Amine sind z. B. Diphenylamin, Phenylnaphthylamin, Dinaphthylamin, Phenyl-a-pyrildylamin. Suitable secondary aromatic amines are e.g. B. Diphenylamine, Phenylnaphthylamine, Dinaphthylamine, phenyl-a-pyrildylamine.

Die Durchführung des Verfahrens erfolgt in der im Patent 939 630 beschnebenen Weise, beispielsweise indem man die sekundären aromatischen Amine mit I Mol Phosgen und anschließend mit Aminoalkoholen, wie sie im Patent 939 630 aufgeführt sind, umsetzt und die so erhaltenen Hydrochloride der Aminourethane bzw. die freien Amino- urethane einige Zeit auf höhere Temperaturen, vorteilhaft auf etwa I80 bis 2500, erhitzt, wobei die Abspaltung von Kohlendioxyd noch durch Zugabe geringer Mengen Kupferpulver beschleunigt werden kann. The method is carried out in the patent 939 630 Beschnebenen manner, for example by using the secondary aromatic amines I mole of phosgene and then with amino alcohols, as listed in patent 939 630 are, reacted and the resulting hydrochlorides of aminourethanes or the free Amino urethane at higher temperatures for some time, advantageous heated to about 180 to 2500, with the elimination of carbon dioxide still through Adding small amounts of copper powder can be accelerated.

Die in den Beispielen angegebenen Teile sind Gewichtsteile. The parts given in the examples are parts by weight.

Beispiel I 100 Teile N, N-Diphenyl-(diäthylamino-äthyl) -urethan, das durch Umsetzen von Diphenylamin mit Phosgen in Xylol und Behandeln des so erhaltenen Diphenylharnstoffchlorids mit Diäthylaminoäthanol hergestellt wurde, werden nach Zugabe geringer Mengen Kupferpulver bis zur Beendigung der Kohlendioxydabspaltung auf 180 bis 2000 erhitzt. Man erhält durch anschließende Destillation des Umsetzungsgemisches bei 2 Torr 83 Teile N, N-Diphenyl- (diäthylamino-äthyl) -amin (Kp.2 I70 bis I750) entsprechend einer Ausbeute von 95 °/o der Theorie. Example I 100 parts of N, N-diphenyl (diethylamino-ethyl) urethane, by reacting diphenylamine with phosgene in xylene and treating the resultant Diphenylurea chloride with diethylaminoethanol was prepared according to Add small amounts of copper powder until the carbon dioxide has been eliminated heated to 180-2000. Subsequent distillation of the reaction mixture is obtained at 2 Torr 83 parts of N, N-diphenyl- (diethylamino-ethyl) amine (Kp.2 I70 to I750) corresponding to a yield of 95% of theory.

Beispiel 2 100 Teile des aus N-Phenyl-f3-naphthylamin mit Phosgen und Diäthylaminoäthanol in der im Beispiel I beschriebenen Weise hergestellten Urethans werden 2 bis 3 Stunden auf 2500 erhitzt, wobei ein kräftiger Kohlendioxydstrom entweicht. Nach Beendigung der Kohlendioxydabspaltung destilliert man den Rückstand bei I Torr, wobei man 86 Teile N - Phenyl - N - fl- naphthyl -(4-diäthylamino - äthyl) -amin vom Siedepunkt 210 bis 2140 erhält. Die Ausbeute- entspricht 98 <>10 der Theorie. Example 2 100 parts of the compound obtained from N-phenyl-f3-naphthylamine with phosgene and diethylaminoethane prepared in the manner described in Example I. are heated to 2500 for 2 to 3 hours, a vigorous stream of carbon dioxide escaping. After the elimination of carbon dioxide has ended, the residue is distilled at 1 Torr, 86 parts of N - phenyl - N - fl-naphthyl - (4-diethylamino - ethyl) amine obtained from boiling point 210 to 2140. The yield corresponds to 98 <> 10 of theory.

Claims (2)

Beispiel 3 27 Teile N, N-Diphenyl-(4-diäthylamino-äthyl)-urethan-hydrochlorid (F. I70 bis 1720), die aus einer ätherischen Lösung des in Beispiel I beschriebenen Urethans mit Chlorwasserstoff erhalten wurden, werden mit einer geringen Menge Kupferpulver im Vakuum auf I70 bis I90° erhitzt, bis die Gasentwicklung aufhört. Das Umsetzungsprodukt wird anschließend destilliert. Man erhält 5,5 Teile N, N-Diphenyl-(ß-diäthylamino-äthyl)-amin vom Kp. Example 3 27 parts of N, N-diphenyl (4-diethylamino-ethyl) urethane hydrochloride (F. 170 to 1720) obtained from an ethereal solution of that described in Example I. Urethanes obtained with hydrogen chloride are made with a small amount of copper powder heated in vacuo to 170 to 190 ° until the evolution of gas ceases. The conversion product is then distilled. 5.5 parts of N, N-diphenyl- (ß-diethylamino-ethyl) amine are obtained from Kp. 2 I70 bis I750 PATENTANSPRUCH: Weiterbildung des Verfahrens des Patents 939 630 zur Herstellung von an einem Stickstoffatom durch basische Gruppen substituierten Verbindungen durch . Erhitzen der aus sekundären Aminen, Phosgen und Aminoalkoholen erhältlichen Urethane, dadurch gekennzeichnet, daß man als Amine sekundäre aromatische Amine verwendet, diese in an sich bekannter Weise mit I Mol Phosgen und anschließend mit Aminoalkoholen zu Aminourethanen umsetzt und letztere oder ihre Hydrohalogenide auf Temperaturen zwischen etwa I80 und 2500 erhitzt.2 I70 to I750 PATENT CLAIM: Further development of the process of patent 939 630 for the preparation of substituted on a nitrogen atom by basic groups Connections through. Heating of secondary amines, phosgene and amino alcohols available urethanes, characterized in that the amines are secondary aromatic Amines used, this in a manner known per se with 1 mole of phosgene and then with amino alcohols to form aminourethanes and the latter or their hydrohalides heated to temperatures between about 180 and 2500.
DEB32488A 1954-09-05 1954-09-05 Process for the preparation of aromatic di-tertiary diamines Expired DE947707C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEB32488A DE947707C (en) 1954-09-05 1954-09-05 Process for the preparation of aromatic di-tertiary diamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB32488A DE947707C (en) 1954-09-05 1954-09-05 Process for the preparation of aromatic di-tertiary diamines

Publications (1)

Publication Number Publication Date
DE947707C true DE947707C (en) 1956-08-23

Family

ID=6963765

Family Applications (1)

Application Number Title Priority Date Filing Date
DEB32488A Expired DE947707C (en) 1954-09-05 1954-09-05 Process for the preparation of aromatic di-tertiary diamines

Country Status (1)

Country Link
DE (1) DE947707C (en)

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