EP0960094A1 - Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine - Google Patents

Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine

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Publication number
EP0960094A1
EP0960094A1 EP98905307A EP98905307A EP0960094A1 EP 0960094 A1 EP0960094 A1 EP 0960094A1 EP 98905307 A EP98905307 A EP 98905307A EP 98905307 A EP98905307 A EP 98905307A EP 0960094 A1 EP0960094 A1 EP 0960094A1
Authority
EP
European Patent Office
Prior art keywords
aminomethylcyclopentylamine
distillation
separation
hexamethylenediamine
amcpa
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.)
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Application number
EP98905307A
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German (de)
French (fr)
Inventor
Hermann Luyken
Alwin Rehfinger
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
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0960094A1 publication Critical patent/EP0960094A1/en
Withdrawn legal-status Critical Current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
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C07C209/84—Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Definitions

  • the present invention relates to a process for separating 2-aminomethylcyclopentylamine (AMCPA) from a mixture comprising hexamethylenediamine and AMCPA.
  • AMCPA 2-aminomethylcyclopentylamine
  • HMI hexamethyleneimine
  • DACH 1, 2-diaminocyclohexane
  • AMCPA hexamethyleneimine
  • the partial or complete hydrogenation of adiponitrile can be carried out by one of the known processes, for example by one of the processes described above in US Pat. No. 4,601,859, US Pat. No. 2,762,835, US Pat 416, DE-A 4 235 466, US-A 3 696 153, DE-A 9 500 222 or WO 92/21650 by generally containing the hydrogenation in the presence of nickel, cobalt, iron or ruthenium Performs catalysts.
  • the catalysts can be used as.
  • Supported catalysts or as unsupported catalysts can be used.
  • aluminum oxide, silicon dioxide, titanium dioxide, magnesium oxide, activated carbon and spinels are suitable as catalyst supports.
  • Raney nickel and Raney cobalt, for example, are suitable as full catalysts.
  • the hydrogenation gives a mixture which contains hexamethylenediamine, AMCPA and optionally 6-aminocapronitrile and adiponitrile.
  • the separation from a mixture containing hexamethylenediamine and AMCPA can be carried out in a manner known per se, preferably by distillation, for example according to DE-A 195 002 22 or German application 19 548 289.1, simultaneously or in succession, for example in a distillation column or in a side draw column Partition (Petlyuk column), so that the condensation temperature of the subsequent cleaning column in the AMCPA separation is generally higher and the condensation is facilitated.
  • the low-boiling secondary component DACH if present, can advantageously be removed simultaneously with AMCPA, but the separation of DACH can also be carried out overhead in a separate column.
  • low-boiling secondary components such as HMI, if present, are advantageously separated off completely or partially.
  • the weight fraction of AMCPA, based on hexamethylenediamine is generally 10 to 10,000 ppm, in particular 100 to 1000 ppm, before the separation, the process according to the invention not being limited to these limits.
  • the separation of AMCPA from the mixture is advantageously carried out by distillation at pressures of between 1 and 1100 mbar, preferably 1 to 500, which results in bottom temperatures in the range from 40 to 250 ° C.
  • distillation columns which have a low pressure drop, preferably at most 1 mbar, in particular 0.5 mbar, per theoretical plate are particularly suitable.
  • Packing columns are particularly suitable, preferably with ordered packing such as sheet metal packs, in particular wire mesh packs.
  • water is added to the distillation mixture, with water contents of 0.01 to 10% by weight, in particular 0.1 to 5% by weight, based on the distillation mixture being preferred.
  • the water can be added to the mixture before the distillation or during the distillation, for example into the column, preferably in the area below the feed, in particular in the bottom area.
  • AMCPA and water are obtained as top product, generally, if hexamethylenediamine and AMCPA are present in the mixture, in a mixture with DACH and low-boiling components.
  • the distillation can be carried out in several, such as 2 or 3 columns, advantageously in a single column.
  • Hexamethylenediamine can be processed with dicarboxylic acids such as adipic acid into technically important polymers.

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

Abstract

The invention relates to a method for separating 2-aminomethylcyclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentyl-amine, characterized in that separation occurs by distillation in the presence of water.

Description

Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminomethylcy- clopentylaminProcess for the separation of 2-aminomethylcyclopentylamine from a mixture containing hexamethylenediamine and 2-aminomethylcyclopentylamine
Beschreibungdescription
Die vorliegende Erfindung betrifft ein Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin (AMCPA) aus einer Mischung ent- haltend Hexamethylendiamin und AMCPA.The present invention relates to a process for separating 2-aminomethylcyclopentylamine (AMCPA) from a mixture comprising hexamethylenediamine and AMCPA.
Die vollständige Hydrierung von Adipodinitril zu Hexamethylendiamin, sowie die partielle Hydrierung unter gleichzeitiger Herstellung von Hexamethylendiamin und 6-Amincapronitril, in Gegen- wart eines Katalysators auf der Basis eines Metalls wie Nickel, Cobalt, Eisen, Rhodium oder Ruthenium ist allgemein bekannt, beispielsweise aus: K. Weissermel, H.-J. Arpe, Industrielle Organische Chemie, 3. Auflage, VCH Verlagsgesellschaft mbH, Weinheim, 1988, Seite 266, US-A 4 601 859, US-A 2 762 835, US-A 2 208 598, DE-A 848 654, DE-A 954 416, DE-A 42 35 466, US-A 3 696 153, DE-A 19500222, WO 92/21650 und der Deutschen Anmeldung 19548289.1.The complete hydrogenation of adiponitrile to hexamethylenediamine, as well as the partial hydrogenation with simultaneous production of hexamethylenediamine and 6-aminapronitrile, in the presence of a catalyst based on a metal such as nickel, cobalt, iron, rhodium or ruthenium is generally known, for example from: K. Weissermel, H.-J. Arpe, Industrial Organic Chemistry, 3rd edition, VCH Verlagsgesellschaft mbH, Weinheim, 1988, page 266, US-A 4 601 859, US-A 2 762 835, US-A 2 208 598, DE-A 848 654, DE- A 954 416, DE-A 42 35 466, US-A 3 696 153, DE-A 19500222, WO 92/21650 and the German application 19548289.1.
Als Nebenprodukte entstehen unter anderem Hexamethylenimin (HMI) , 1, 2-Diaminocyclohexan (DACH) und AMCPA.By-products include hexamethyleneimine (HMI), 1, 2-diaminocyclohexane (DACH) and AMCPA.
Aus US-A 3 696 153 ist bekannt, daß das durch diese Hydrierung erhaltene Hexamethylendiamin als Nebenprodukt AMCPA enthält, das sich extrem schwer von der Mischung abtrennen läßt.It is known from US Pat. No. 3,696,153 that the hexamethylenediamine obtained by this hydrogenation contains AMCPA as a by-product, which is extremely difficult to separate from the mixture.
Aufgabe der vorliegenden Erfindung war es daher, ein Verfahren bereitzustellen, das die Abtrennung von AMCPA von einer Mischung, die im wesentlichen Hexamethylendiamin und AMCPA enthält, auf technisch einfache und wirtschaftliche Weise ermöglicht.It was therefore an object of the present invention to provide a process which enables the separation of AMCPA from a mixture which essentially contains hexamethylenediamine and AMCPA in a technically simple and economical manner.
Demgemäß wurde ein Verfahren zur Abtrennung von AMCPA aus einer Mischung enthaltend Hexamethylendiamin und AMCPA, dadurch gekennzeichnet, daß man die Trennung destillativ in Gegenwart von Wasser durchführt, gefunden.Accordingly, a process for the separation of AMCPA from a mixture containing hexamethylenediamine and AMCPA, characterized in that the separation is carried out by distillation in the presence of water, was found.
Die partielle oder vollständige Hydrierung von Adipodinitril kann man nach einem der bekannten Verfahren durchführen, beispielsweise nach einem der zuvor genannten Verfahren beschrieben in US 4 601 859, US 2 762 835, US 2 208 598, DE-A 848 654, DE-A 954 416, DE-A 4 235 466, US-A 3 696 153, DE-A 9 500 222 oder WO 92/21650, indem man im allgemeinen die Hydrierung in Gegenwart von Nickel-, Cobalt-, Eisen- oder Ruthenium-haltigen Katalysatoren durchführt. Dabei können die Katalysatoren als. Trägerkatalysatoren oder als Vollkatalysatoren verwendet werden. Als Katalysatorträger kommen beispielsweise Aluminiumoxid, Siliciumdioxid, Titandioxid, Magnesiumoxid, Aktivkohlen und Spinelle in Frage. Als Vollkatalysatoren kommen beispielsweise Raney-Nickel und Raney-Cobalt in Betracht.The partial or complete hydrogenation of adiponitrile can be carried out by one of the known processes, for example by one of the processes described above in US Pat. No. 4,601,859, US Pat. No. 2,762,835, US Pat 416, DE-A 4 235 466, US-A 3 696 153, DE-A 9 500 222 or WO 92/21650 by generally containing the hydrogenation in the presence of nickel, cobalt, iron or ruthenium Performs catalysts. The catalysts can be used as. Supported catalysts or as unsupported catalysts can be used. For example, aluminum oxide, silicon dioxide, titanium dioxide, magnesium oxide, activated carbon and spinels are suitable as catalyst supports. Raney nickel and Raney cobalt, for example, are suitable as full catalysts.
Bei der Hydrierung erhält man eine Mischung, die Hexamethylendiamin, AMCPA und gegebenenfalls 6 -Aminocapronitril und Adipodi- nitril enthält.The hydrogenation gives a mixture which contains hexamethylenediamine, AMCPA and optionally 6-aminocapronitrile and adiponitrile.
Die Abtrennung von einer Mischung enthaltend Hexamethylendiamin und AMCPA kann in an sich bekannter Weise, vorzugsweise destillativ, beispielsweise gemäß der DE-A 195 002 22 oder der Deutschen Anmeldung 19 548 289.1, gleichzeitig oder nacheinander erfolgen, beispielsweise in einer Destillationskolonne oder in einer Seitenabzugskolonne mit Trennwand (Petlyuk-Kolonne) , so daß die Kondensationstemperatur der nachfolgenden Reinigungskolonne bei der AMCPA-Trennung in der Regel höher und die Kondensation erleichtert ist. Die leichtsiedende Nebenkomponente DACH kann, sofern vorhanden, vorteilhaft gleichzeitig mit AMCPA abgetrennt werden, die Abtrennung von DACH kann aber auch in einer separaten Kolonne über Kopf erfolgen.The separation from a mixture containing hexamethylenediamine and AMCPA can be carried out in a manner known per se, preferably by distillation, for example according to DE-A 195 002 22 or German application 19 548 289.1, simultaneously or in succession, for example in a distillation column or in a side draw column Partition (Petlyuk column), so that the condensation temperature of the subsequent cleaning column in the AMCPA separation is generally higher and the condensation is facilitated. The low-boiling secondary component DACH, if present, can advantageously be removed simultaneously with AMCPA, but the separation of DACH can also be carried out overhead in a separate column.
Vorteilhaft trennt man vor der Reinigung des Hexamethylendiamins nach dem erfindungsgemäßen Verfahren leichtsiedende Neben- komponenten, wie HMI, sofern vorhanden, vollständig oder teilweise ab.Before the hexamethylenediamine is purified by the process according to the invention, low-boiling secondary components, such as HMI, if present, are advantageously separated off completely or partially.
In die Mischung enthaltend Hexamethylendiamin und AMCPA beträgt vor der Trennung im allgemeinen der Gewichtsanteil an AMCPA, bezogen auf Hexamethylendiamin, 10 bis 10000 ppm, insbesondere 100 bis 1000 ppm, wobei das erfindungsgemäße Verfahren nicht auf diese Grenzen beschränkt ist.In the mixture containing hexamethylenediamine and AMCPA, the weight fraction of AMCPA, based on hexamethylenediamine, is generally 10 to 10,000 ppm, in particular 100 to 1000 ppm, before the separation, the process according to the invention not being limited to these limits.
Die Abtrennung von AMCPA aus der Mischung führt man vorteilhaft destillativ bei Drücken von zwischen 1 und 1100 mbar, vorzugsweise 1 bis 500 durch, wodurch sich Sumpftemperaturen im Bereich von 40 bis 250°C ergeben.The separation of AMCPA from the mixture is advantageously carried out by distillation at pressures of between 1 and 1100 mbar, preferably 1 to 500, which results in bottom temperatures in the range from 40 to 250 ° C.
Für die Destillation kommen hierfür übliche Apparaturen in Betracht, wie sie beispielsweise in: Kirk-Othmer, Encyclopedia of Chemical Technology, 3. Ed., Vol. 7, John Wiley & Sons, New York, 1979, Seite 870-881 beschrieben sind, wie Siebbodenkolonnen, Glockenbodenkolonnen oder Füllkörperkolonnen. Besonders geeignet sind Destillationskolonnen, die einen geringen Druckverlust, vorzugsweise höchstens 1 mbar, insbesondere 0,5 mbar pro theoretischer Trennstufe aufweisen.For the distillation, customary apparatuses are considered, such as those described in: Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd Ed., Vol. 7, John Wiley & Sons, New York, 1979, pages 870-881, such as sieve plate columns, bubble plate plate columns or packed columns. Distillation columns which have a low pressure drop, preferably at most 1 mbar, in particular 0.5 mbar, per theoretical plate are particularly suitable.
Insbesondere geeignet sind Packungskolonnen, vorzugsweise mit geordneten Füllkörpern wie Metallblechpackungen, insbesondere Drahtgewebepackungen.Packing columns are particularly suitable, preferably with ordered packing such as sheet metal packs, in particular wire mesh packs.
Erfindungsgemäß gibt man dem Destillationsgemisch Wasser zu, wo- bei Wassergehalte von 0,01 bis 10 Gew. -%, insbesondere 0,1 bis 5 Gew. -% bezogen auf das Destillationsgemisch bevorzugt sind.According to the invention, water is added to the distillation mixture, with water contents of 0.01 to 10% by weight, in particular 0.1 to 5% by weight, based on the distillation mixture being preferred.
Das Wasser kann dabei dem Gemisch vor der Destillation oder während der Destillation, beispielsweise in die Kolonne, Vorzugs- weise in den Bereich unterhalb des Zulaufs, insbesondere in den Sumpf -Bereich, zugegeben werden.The water can be added to the mixture before the distillation or during the distillation, for example into the column, preferably in the area below the feed, in particular in the bottom area.
Nach dem erfindungsgemäßen Verfahren werden AMCPA und Wasser als Kopfprodukt erhalten, im allgemeinen, sofern im Gemisch enthal- tend Hexamethylendiamin und AMCPA vorhanden, im Gemisch mit DACH und leichtsiedenden Komponenten.In the process according to the invention, AMCPA and water are obtained as top product, generally, if hexamethylenediamine and AMCPA are present in the mixture, in a mixture with DACH and low-boiling components.
Die Destillation kann man in mehreren, wie 2 oder 3 Kolonnen, vorteilhaft einer einzigen Kolonne durchführen.The distillation can be carried out in several, such as 2 or 3 columns, advantageously in a single column.
Hexamethylendiamin kann mit Dicarbonsäuren wie Adipinsäure zu technisch bedeutenden Polymeren verarbeitet werden. Hexamethylenediamine can be processed with dicarboxylic acids such as adipic acid into technically important polymers.

Claims

Patentansprüche claims
1. Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminome- thylcyclopentylamin, dadurch gekennzeichnet, daß man die Trennung destillativ in Gegenwart von Wasser durchführt.1. A process for the separation of 2-aminomethylcyclopentylamine from a mixture containing hexamethylenediamine and 2-aminomethylcyclopentylamine, characterized in that the separation is carried out by distillation in the presence of water.
2. Verfahren nach Anspruch 1, wobei man als Destillationsappara- tur eine Destillationskolonne einsetzt.2. The method according to claim 1, wherein a distillation column is used as the distillation apparatus.
3. Verfahren nach Anspruch 1 oder 2, wobei man als Destillationsapparatur eine Packungskolonne einsetzt.3. The method according to claim 1 or 2, wherein a packing column is used as the distillation apparatus.
4. Verfahren nach den Ansprüchen 1 bis 3, wobei man als Destillationsapparatur eine Destillationskolonne einsetzt, die einen Druckverlust von höchstens 1 mbar pro theoretischer Trennstufe aufweist.4. The method according to claims 1 to 3, wherein a distillation column is used as the distillation apparatus, which has a pressure loss of at most 1 mbar per theoretical plate.
5. Verfahren nach den Ansprüchen 1 bis 4, wobei der Gewichts - anteil an 2-Aminomethylcyclopentylamin, bezogen auf Hexamethylendiamin, vor der Trennung 1 bis 10000 ppm beträgt.5. Process according to claims 1 to 4, wherein the weight fraction of 2-aminomethylcyclopentylamine, based on hexamethylenediamine, is 1 to 10,000 ppm before the separation.
6. Verfahren nach den Ansprüchen 1 bis 5, wobei der Gewichts- anteil an 2-Aminomethylcyclopentylamin, bezogen auf Hexamethylendiamin, nach der Trennung 0 bis 100 ppm beträgt. 6. The method according to claims 1 to 5, wherein the weight fraction of 2-aminomethylcyclopentylamine, based on hexamethylene diamine, is 0 to 100 ppm after the separation.
EP98905307A 1997-02-07 1998-01-17 Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine Withdrawn EP0960094A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19704618 1997-02-07
DE19704618A DE19704618A1 (en) 1997-02-07 1997-02-07 Process for the separation of 2-aminomethylcyclopentylamine from a mixture containing hexamethylenediamine and 2-aminomethylcyclopentylamine
PCT/EP1998/000241 WO1998034901A1 (en) 1997-02-07 1998-01-17 Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine

Publications (1)

Publication Number Publication Date
EP0960094A1 true EP0960094A1 (en) 1999-12-01

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EP98905307A Withdrawn EP0960094A1 (en) 1997-02-07 1998-01-17 Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine

Country Status (10)

Country Link
EP (1) EP0960094A1 (en)
JP (1) JP2001511163A (en)
KR (1) KR20000070888A (en)
CN (1) CN1251567A (en)
AR (1) AR011636A1 (en)
AU (1) AU6094798A (en)
BR (1) BR9807188A (en)
CA (1) CA2280830A1 (en)
DE (1) DE19704618A1 (en)
WO (1) WO1998034901A1 (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB731819A (en) * 1951-04-11 1955-06-15 Du Pont Improvements in or relating to the production of hexamethylene diamine and salts thereof
GB1125706A (en) * 1965-01-20 1968-08-28 Ici Ltd Process for the production of hexamethylene diamine
DE1543973A1 (en) * 1966-06-08 1970-02-05 Vickers Zimmer Ag Method for purifying hexamethylenediamine
CA915707A (en) * 1969-07-11 1972-11-28 J. Kershaw Bernard Hydrogenation of adiponitrile
SU810669A1 (en) * 1978-12-06 1981-03-07 Предприятие П/Я В-2609 Method of hexamethylenediamine purification

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9834901A1 *

Also Published As

Publication number Publication date
AU6094798A (en) 1998-08-26
DE19704618A1 (en) 1998-08-13
KR20000070888A (en) 2000-11-25
AR011636A1 (en) 2000-08-30
CA2280830A1 (en) 1998-08-13
JP2001511163A (en) 2001-08-07
BR9807188A (en) 2000-01-25
WO1998034901A1 (en) 1998-08-13
CN1251567A (en) 2000-04-26

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