DE620510C - Process for the preparation of secondary or tertiary amines - Google Patents

Process for the preparation of secondary or tertiary amines

Info

Publication number
DE620510C
DE620510C DEI49774D DEI0049774D DE620510C DE 620510 C DE620510 C DE 620510C DE I49774 D DEI49774 D DE I49774D DE I0049774 D DEI0049774 D DE I0049774D DE 620510 C DE620510 C DE 620510C
Authority
DE
Germany
Prior art keywords
weight
parts
preparation
tertiary amines
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
DEI49774D
Other languages
German (de)
Inventor
Dr Walter Speer
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 DEI49774D priority Critical patent/DE620510C/en
Application granted granted Critical
Publication of DE620510C publication Critical patent/DE620510C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals

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

Description

Verfahren zur Herstellung vom sekundären oder tertiären Aminen Gegenstand des Hauptpatents 618 032 ist ein Verfahren zur Herstellung von sekundären oder tertiären aromatischen Aminen, bei dem man auf primäre oder sekundäre aromatische Amine Ketone oder Aldehyde in Gegenwart von Ameisensäureestern bei erhöhter Temperatur einwirken läßt.Process for the preparation of secondary or tertiary amines The subject of the main patent 618 032 is a process for the preparation of secondary or tertiary aromatic amines, in which ketones or aldehydes are allowed to act on primary or secondary aromatic amines in the presence of formic acid esters at elevated temperature.

Es wurde nun gefunden, daB nicht nur arömatische Amine, sondern auch andere Stickstoffbasen, die wenigstens ein freies Wasserstoffatom am Stickstoff enthalten, z. B. aliphatische oder cycloaliphatische Amine oder heterocyclische Basen, durch Einwirkung von Aldehyden oder Ketonen in Gegenwart von Ameisensäureestern in sehr vorteilhafter Weise in sekundäre oder tertiäre Amine übergeführt werden können.It has now been found that not only aromatic amines but also other nitrogen bases that have at least one free hydrogen atom on the nitrogen included, e.g. B. aliphatic or cycloaliphatic amines or heterocyclic Bases, by the action of aldehydes or ketones in the presence of formic acid esters be converted in a very advantageous manner into secondary or tertiary amines can.

Beispiel i 278 Gewichtsteile Dodecylamin, 94,5 Gewichtsteile Methylformiat und 174 Gewichtsteile Cyclohexanon werden in einem Autoklaven 3 bis 4 Stunden lang unter Entspannen der gebildeten Kohlensäure auf 24o° erhitzt. Nach beendeter Reaktion wird durch fraktionierte Destillation des Autoklaveninhaltes reines N-Cyclohexyl-dodecylamin erhalten, das unter einem Druck von 4,4 mm bei 171 bis r74° siedet.Example i 278 parts by weight of dodecylamine, 94.5 parts by weight of methyl formate and 174 parts by weight of cyclohexanone are in an autoclave for 3 to 4 hours heated to 240 ° while releasing the carbon dioxide formed. After the reaction has ended becomes pure N-cyclohexyl-dodecylamine by fractional distillation of the contents of the autoclave obtained boiling under a pressure of 4.4 mm at 171 to r74 °.

Beispiel 2 z7o Gewichtsteile Piperidin, z26 Gewichtsteile Methylformiat und Zoo Gewichtsteile Cyclohexanon werden unter Entspannung der gebildeten Kohlensäure 4 Stunden lang auf 23o° erhitzt. Der Autoklaveninhalt wird sodann fraktioniert destilliert. Unter einem Druck von 2,2 mm geht N-Cyclohexyl-piperidin bei einer Temperatur von 122 bis r23° über. Beispiel 3 297 Gewichtsteile Monocyclohexylamin, 294 Gewichtsteile Cyclohexanon und 189 Gewichtsteile Methylformiat werden 5 Stunden lang auf 24o° erhitzt, wobei die gebildete Kohlensäure entspannt wird. Nach beendeter Reaktion wird der Autoklaveninhalt fraktioniert destilliert. Dicyclohexylamin geht unter einem Druck von 16 mm zwischen i3o und i32° über.Example 2 70 parts by weight piperidine, 26 parts by weight methyl formate and zoo parts by weight of cyclohexanone are formed with relaxation of the carbonic acid Heated to 230 ° for 4 hours. The contents of the autoclave are then fractionally distilled. Under a pressure of 2.2 mm, N-Cyclohexyl-piperidine goes at a temperature of 122 to r23 ° over. Example 3 297 parts by weight monocyclohexylamine, 294 parts by weight Cyclohexanone and 189 parts by weight of methyl formate are heated to 24o ° for 5 hours heated, whereby the carbonic acid formed is relaxed. After the reaction has ended the contents of the autoclave are fractionally distilled. Dicyclohexylamine goes under a pressure of 16 mm between i3o and i32 ° above.

Es kann auch in der Weise gearbeitet werden, daß ein Gemisch von 5o Gewichtsteilen Cyclohexylamin, 5o Gewichtsteilen Cyclohexanon und 45 Gewichtsteilen Methylformiat unter gewöhnlichem Druck in Dampfform bei 35o° langsam- durch ein- VA-Rohr geleitet wird, das- mit V..A-Spänen-,gefüllt ist. Das Reaktionsprodukt wird fraktioniert, wobei Dicyclohexylamin bei einem Druck von 14 mm bei zag bis 1300 übergeht.It is also possible to work in such a way that a mixture of 50 parts by weight of cyclohexylamine, 50 parts by weight of cyclohexanone and 45 parts by weight of methyl formate is slowly passed through a VA tube under normal pressure in vapor form at 35 ° C. -Chippings-, is filled. The reaction product is fractionated, with dicyclohexylamine passing over at a pressure of 14 mm at zag up to 1300 .

a Beispiel q.a example q.

83 Gewichtsteile Piperidin, 1o6 Gewichtsteile Benzaldehyd und 63 Gewichtsteile Methylformiat werden 4 Stunden in einem Autoklaven auf a400 erhitzt. Der Autoklaveninhalt wird dann fraktioniert destilliert, wobei N-Benzyl-piperidin erhalten wird, das unter einem Druck von a1 mm zwischen 133 und 1340 überdestilliert.83 parts by weight of piperidine, 106 parts by weight of benzaldehyde and 63 parts by weight Methyl formate is heated to a400 in an autoclave for 4 hours. The contents of the autoclave is then fractionally distilled to give N-benzyl-piperidine, the distilled over under a pressure of a1 mm between 133 and 1340.

Beispiel 5 198 Gewichtsteile Cyclohexylamin, 12o Gewichtsteile Aceton und 126 Gewichtsteile Methylformiat werden 3 Stunden auf 26od erhitzt. Bei der Destillation des Reaktionsproduktes wird . N-Isopropyl-cyclohexylamin erhalten, das unter einem Druck von 64,5 min zwischen 93 und 94' übergeht.Example 5 198 parts by weight of cyclohexylamine, 12o parts by weight of acetone and 126 parts by weight of methyl formate are heated to 26 ° for 3 hours. During the distillation of the reaction product. N-Isopropyl-cyclohexylamine obtained under a Pressure of 64.5 min transitions between 93 and 94 '.

Claims (1)

PATENTANSPRUCFI: Verfahren zur Herstellung von sekundären oder tertiären Aminen durch Erhitzen von primären oder sekundären Aminen mit Aldehyden oder Ketonen in Gegenwart von Ameisensäureestern, dadurch gekennzeichnet,, daB man in Abänderung des Verfahrens des Hauptpatents 618 032 an Stelle von aromatischen Aminen hier Stickstoffbasen nichtaromatischer Natur, die mindestens ein freies Wasserstoffatom am Stickstoff enthalten, als Ausgangsstoffe verwendet.PATENT CLAIM: Process for the preparation of secondary or tertiary amines by heating primary or secondary amines with aldehydes or ketones in the presence of formic acid esters, characterized in that, in a modification of the process of main patent 618 032 , instead of aromatic amines, nitrogen bases of a non-aromatic nature are used, which contain at least one free hydrogen atom on the nitrogen, used as starting materials.
DEI49774D 1934-05-25 1934-05-25 Process for the preparation of secondary or tertiary amines Expired DE620510C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI49774D DE620510C (en) 1934-05-25 1934-05-25 Process for the preparation of secondary or tertiary amines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI49774D DE620510C (en) 1934-05-25 1934-05-25 Process for the preparation of secondary or tertiary amines

Publications (1)

Publication Number Publication Date
DE620510C true DE620510C (en) 1935-10-23

Family

ID=7192661

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI49774D Expired DE620510C (en) 1934-05-25 1934-05-25 Process for the preparation of secondary or tertiary amines

Country Status (1)

Country Link
DE (1) DE620510C (en)

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