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WO1998034901A1 - Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine - Google Patents

Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine Download PDF

Info

Publication number
WO1998034901A1
WO1998034901A1 PCT/EP1998/000241 EP9800241W WO9834901A1 WO 1998034901 A1 WO1998034901 A1 WO 1998034901A1 EP 9800241 W EP9800241 W EP 9800241W WO 9834901 A1 WO9834901 A1 WO 9834901A1
Authority
WO
WIPO (PCT)
Prior art keywords
aminomethylcyclopentylamine
distillation
separation
hexamethylenediamine
amcpa
Prior art date
Application number
PCT/EP1998/000241
Other languages
German (de)
English (en)
Inventor
Hermann Luyken
Alwin Rehfinger
Original Assignee
Basf Aktiengesellschaft
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 Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to BR9807188-2A priority Critical patent/BR9807188A/pt
Priority to EP98905307A priority patent/EP0960094A1/fr
Priority to JP53367398A priority patent/JP2001511163A/ja
Priority to AU60947/98A priority patent/AU6094798A/en
Priority to CA002280830A priority patent/CA2280830A1/fr
Publication of WO1998034901A1 publication Critical patent/WO1998034901A1/fr

Links

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.

Landscapes

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

Abstract

L'invention concerne un procédé permettant de séparer de la diamine de 2-aminométhylène et de la 2-aminométhylcyclopentylamine qui se caractérise en ce que la séparation s'effectue par distillation en présence d'eau.
PCT/EP1998/000241 1997-02-07 1998-01-17 Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine WO1998034901A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR9807188-2A BR9807188A (pt) 1997-02-07 1998-01-17 Processo para separação de 2-amino-metil-ciclo-pentil-amina de uma mistura compreendendo hexametileno-diamina e 2-amino-etil-ciclo-pentil-amina.
EP98905307A EP0960094A1 (fr) 1997-02-07 1998-01-17 Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine
JP53367398A JP2001511163A (ja) 1997-02-07 1998-01-17 ヘキサメチレンジアミンと２−アミノメチルシクロペンチルアミンを含有する混合物から２−アミノメチルシクロペンチルアミンを分離する方法
AU60947/98A AU6094798A (en) 1997-02-07 1998-01-17 Method for separating 2-aminomethylcylclopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcyclopentylamine
CA002280830A CA2280830A1 (fr) 1997-02-07 1998-01-17 Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19704618.5 1997-02-07
DE19704618A DE19704618A1 (de) 1997-02-07 1997-02-07 Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminomethylcyclopentylamin

Publications (1)

Publication Number Publication Date
WO1998034901A1 true WO1998034901A1 (fr) 1998-08-13

Family

ID=7819570

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/000241 WO1998034901A1 (fr) 1997-02-07 1998-01-17 Procede pour separer de la 2-aminomethylcyclopentylamine contenue dans un melange comprenant de la diamine d'hexamethylene et de la 2-aminomethylcyclopentylamine

Country Status (10)

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

Citations (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
FR1464546A (fr) * 1965-01-20 1966-12-30 Ici Ltd Fabrication de l'hexaméthylène-diamine
DE1543973A1 (de) * 1966-06-08 1970-02-05 Vickers Zimmer Ag Verfahren zur Reinigung von Hexamethylendiamin
US3696153A (en) * 1969-07-11 1972-10-03 Du Pont Hydrogenation of adiponitrile
SU810669A1 (ru) * 1978-12-06 1981-03-07 Предприятие П/Я В-2609 Способ очистки гексаметилендиа-МиНА

Patent Citations (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
FR1464546A (fr) * 1965-01-20 1966-12-30 Ici Ltd Fabrication de l'hexaméthylène-diamine
DE1543973A1 (de) * 1966-06-08 1970-02-05 Vickers Zimmer Ag Verfahren zur Reinigung von Hexamethylendiamin
US3696153A (en) * 1969-07-11 1972-10-03 Du Pont Hydrogenation of adiponitrile
SU810669A1 (ru) * 1978-12-06 1981-03-07 Предприятие П/Я В-2609 Способ очистки гексаметилендиа-МиНА

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 8149, Derwent World Patents Index; Class A41, AN 81-90805D, XP002064653 *
DATABASE WPI Section Ch Week 8348, Derwent World Patents Index; Class A41, AN 83-831192, XP002064652 *

Also Published As

Publication number Publication date
JP2001511163A (ja) 2001-08-07
EP0960094A1 (fr) 1999-12-01
BR9807188A (pt) 2000-01-25
DE19704618A1 (de) 1998-08-13
CA2280830A1 (fr) 1998-08-13
KR20000070888A (ko) 2000-11-25
CN1251567A (zh) 2000-04-26
AR011636A1 (es) 2000-08-30
AU6094798A (en) 1998-08-26

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