WO1998034902A1 - Method for separating 2-aminomethylcylcopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcylopentylamine - Google Patents

Method for separating 2-aminomethylcylcopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcylopentylamine Download PDF

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Publication number
WO1998034902A1
WO1998034902A1 PCT/EP1998/000242 EP9800242W WO9834902A1 WO 1998034902 A1 WO1998034902 A1 WO 1998034902A1 EP 9800242 W EP9800242 W EP 9800242W WO 9834902 A1 WO9834902 A1 WO 9834902A1
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mbar
hexamethylenediamine
amcpa
separation
distillation
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PCT/EP1998/000242
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German (de)
French (fr)
Inventor
Hermann Luyken
Alwin Rehfinger
Peter Bassler
Guido Voit
Rolf Fischer
Martin Merger
Harald Rust
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Basf Aktiengesellschaft
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Priority to AU58640/98A priority Critical patent/AU5864098A/en
Publication of WO1998034902A1 publication Critical patent/WO1998034902A1/en

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    • 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
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—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
  • a process for the separation of AMCPA from a mixture containing hexamethylenediamine and AMCPA characterized in that the separation is carried out by distillation at a pressure of 1 to 300 mbar.
  • 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 comprising essentially hexamethylenediamine and AMCPA can be carried out simultaneously or in succession 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, for example in a distillation column or in one Side draw column with dividing wall (Petlyuk column), so that the condensation temperature of the subsequent cleaning column is generally higher during the AMCPA separation and the condensation is facilitated.
  • the low-boiling secondary component DACH if present, can advantageously be separated off 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 carried out according to the invention by distillation at pressures of between 1 and 300 mbar, preferably 1 to 200 mbar, which results in bottom temperatures in the range from 40 to 160 ° C.
  • Distillation apparatuses which have a pressure drop from 0 to 200 mbar, preferably 0 to 50 mbar, from the bottom to the top, the pressure in the bottom in the range from 3 to 300 mbar, in particular 3 to 200 mbar, and in the top in the range from 1 up to 300 mbar, in particular 1 to 200 mbar.
  • 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.
  • the AMCPA is obtained as the top product, generally, if present in a mixture comprising hexamethylenediamine and AMCPA, 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 to give technically important polymers.
  • 300 g / h HMD with a DACH content of 6850 ppm, an AMCPA content of 270 ppm and a content of 1, 5-diamino-2-methylpentane (MPMDA) of 11 ppm were in a column with low pressure loss tissue packing corresponding to 66 theoretical Separation stages supplied.
  • a pressure of 100 mbar was set at the top of the column and a pressure of 103 mbar was measured in the bottom.
  • a constant 33 g / h of distillate were taken off at the top of the column and 1650 g / h were returned as the column's reflux. After a running time of 24 h, the distillate and bottom discharge were collected over 17 h.
  • the AMCPA content of the hexamethylenediamine obtained as the bottom product was 6 ppm, the DACH and MPMDA content was below the detection limit of 1 ppm.
  • the hexamethylene diamine content of the top product was 93.5%.

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 by distillation occurs at a pressure of 1-3,000 mbars.

Description

Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexa ethylendiamin und 2-Aminomethylcy- clopentylamin Process for the separation of 2-aminomethylcyclopentylamine from a mixture containing hexa-ethylenediamine 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 bei einem Druck von 1 bis 300 mbar 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 at a pressure of 1 to 300 mbar.
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 im wesentlichen 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 Re- gel höher und die Kondensation erleichtert ist. Die leicht - siedende 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 comprising essentially hexamethylenediamine and AMCPA can be carried out simultaneously or in succession 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, for example in a distillation column or in one Side draw column with dividing wall (Petlyuk column), so that the condensation temperature of the subsequent cleaning column is generally higher during the AMCPA separation and the condensation is facilitated. The low-boiling secondary component DACH, if present, can advantageously be separated off 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 Nebenkomponenten, 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 erfindungs- gemäß destillativ bei Drücken von zwischen 1 und 300 mbar, vorzugsweise 1 bis 200 mbar durch, wodurch sich Sumpftemperaturen im Bereich von 40 bis 160°C ergeben.The separation of AMCPA from the mixture is carried out according to the invention by distillation at pressures of between 1 and 300 mbar, preferably 1 to 200 mbar, which results in bottom temperatures in the range from 40 to 160 ° 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. Bevorzugt sind Destillationsapparturen, die vom Sumpf zum Kopf einen Druckabfall von 0 bis 200 mbar, vorzugsweise 0 bis 50 mbar aufweisen, wobei vorteilhaft der Druck im Sumpf im Bereich von 3 bis 300 mbar, insbesondere 3 bis 200 mbar und im Kopf im Bereich von 1 bis 300 mbar, insbesondere 1 bis 200 mbar, liegen sollte.Conventional apparatuses are suitable for the distillation, as described, for example, 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 apparatuses are preferred which have a pressure drop from 0 to 200 mbar, preferably 0 to 50 mbar, from the bottom to the top, the pressure in the bottom in the range from 3 to 300 mbar, in particular 3 to 200 mbar, and in the top in the range from 1 up to 300 mbar, in particular 1 to 200 mbar.
Besonders geeignet sind Destillationskolonnen, die einen geringen Druckverlust, vorzugsweise höchstens 1 mbar, insbesondere 0,5 mbar pro theoretischer Trennstufe aufweisen.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.
Nach dem erfindungsgemäßen Verfahren wird das AMCPA als Kopf - Produkt erhalten, im allgemeinen, sofern im Gemisch enthaltend Hexamethylendiamin und AMCPA vorhanden, im Gemisch mit DACH und leichtsiedenden Komponenten.In the process according to the invention, the AMCPA is obtained as the top product, generally, if present in a mixture comprising hexamethylenediamine and AMCPA, 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 Adipinsaure zu technisch bedeutenden Polymeren verarbeitet werden.Hexamethylenediamine can be processed with dicarboxylic acids such as adipic acid to give technically important polymers.
Beispielexample
300 g/h HMD mit einem DACH-Gehalt von 6850 ppm, einem AMCPA- Gehalt von 270 ppm und einem Gehalt an 1, 5-Diamino-2-methylpentan (MPMDA) von 11 ppm wurden in einer Kolonne mit druckverlustarmer Gewebepackung entsprechend 66 theoretischen Trennstufen zugeführt. Am Kopf der Kolonne wurde ein Druck von 100 mbar eingestellt, im Sumpf ein Druck von 103 mbar gemessen. Am Kopf der Kolonne wurden konstant 33 g/h Destillat abgenommen und 1650 g/h als Rücklauf der Kolonne zurückgeführt. Nach einer Laufzeit von 24 h wurden Destillat und Sumpfaustrag über 17 h gesammelt.300 g / h HMD with a DACH content of 6850 ppm, an AMCPA content of 270 ppm and a content of 1, 5-diamino-2-methylpentane (MPMDA) of 11 ppm were in a column with low pressure loss tissue packing corresponding to 66 theoretical Separation stages supplied. A pressure of 100 mbar was set at the top of the column and a pressure of 103 mbar was measured in the bottom. A constant 33 g / h of distillate were taken off at the top of the column and 1650 g / h were returned as the column's reflux. After a running time of 24 h, the distillate and bottom discharge were collected over 17 h.
Der Gehalt an AMCPA des als Sumpf rodukt erhaltenen Hexamethylendiamins betrug 6 ppm, der Gehalt an DACH und MPMDA lag unter der Nachweisgrenze von 1 ppm. Der Gehalt an Hexamethylendiamin des KopfProduktes betrug 93,5 %. The AMCPA content of the hexamethylenediamine obtained as the bottom product was 6 ppm, the DACH and MPMDA content was below the detection limit of 1 ppm. The hexamethylene diamine content of the top product was 93.5%.

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 bei einem Druck von 1 bis 300 mbar durchführt .1. A process for the separation of 2-aminomethylcyclopentylamine from a mixture comprising hexamethylenediamine and 2-aminomethylcyclopentylamine, characterized in that the separation is carried out by distillation at a pressure of 1 to 300 mbar.
2. Verfahren nach Anspruch 1, wobei der Druckverlust zwischen dem Kopf und dem Sumpf der Destillationsapparatur zwischen 0 und 200 mbar beträgt.2. The method according to claim 1, wherein the pressure loss between the top and the bottom of the distillation apparatus is between 0 and 200 mbar.
3. Verfahren nach Anspruch 1 oder 2, wobei der Druck im Sumpf der Destillationsapparatur zwischen 3 und 300 mbar beträgt.3. The method according to claim 1 or 2, wherein the pressure in the bottom of the distillation apparatus is between 3 and 300 mbar.
4. Verfahren nach den Ansprüchen 1 bis 3, wobei der Druck im Kopf der Destillationsapparatur zwischen 1 und 300 mbar beträgt.4. The method according to claims 1 to 3, wherein the pressure in the top of the distillation apparatus is between 1 and 300 mbar.
Verfahren nach den Ansprüchen 1 bis 4, wobei man als Destillationsapparatur eine Destillationskolonne einsetzt.Process according to claims 1 to 4, wherein a distillation column is used as the distillation apparatus.
6. Verfahren nach den Ansprüchen 1 bis 5, wobei man als De- stillationsapparatur eine Packungskolonne einsetzt.6. The method according to claims 1 to 5, wherein a packing column is used as the distillation apparatus.
7. Verfahren nach den Ansprüchen 1 bis 6, wobei man als Destillationsapparatur eine Destillationskolonne einsetzt, die einen Druckverlust von höchstens 1 mbar pro theoretischer Trennstufe aufweist.7. The method according to claims 1 to 6, wherein a distillation column is used as the distillation apparatus, which has a pressure loss of at most 1 mbar per theoretical plate.
8. Verfahren nach den Ansprüchen 1 bis 7, wobei der Gewichtsanteil an 2-Aminomethylcyclopentylamin, bezogen auf Hexamethylendiamin, vor der Trennung 1 bis 10000 ppm beträgt.8. The method according to claims 1 to 7, wherein the weight fraction of 2-aminomethylcyclopentylamine, based on hexamethylenediamine, is 1 to 10,000 ppm before the separation.
Verfahren nach den Ansprüchen 1 bis 8, wobei der Gewichts- anteil an 2-Aminomethylcyclopentylamin, bezogen auf Hexamethylendiamin, nach der Trennung 0 bis 100 ppm beträgt. Process according to claims 1 to 8, wherein the weight fraction of 2-aminomethylcyclopentylamine, based on hexamethylenediamine, is 0 to 100 ppm after the separation.
PCT/EP1998/000242 1997-02-07 1998-01-17 Method for separating 2-aminomethylcylcopentylamine from a mixture containing hexamethylene diamine and 2-aminomethylcylopentylamine WO1998034902A1 (en)

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DE19704616.9 1997-02-07
DE19704616A DE19704616A1 (en) 1997-02-07 1997-02-07 Process for the separation of 2-aminomethylcyclopentylamine from a mixture containing hexamethylenediamine and 2-aminomethylcyclopentylamine

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1543973A1 (en) * 1966-06-08 1970-02-05 Vickers Zimmer Ag Method for purifying hexamethylenediamine
US3652545A (en) * 1969-11-28 1972-03-28 Celanese Corp Process for preparing n-(6-aminohexyl) hexamethyleneimine
FR2722784A1 (en) * 1994-07-21 1996-01-26 Rhone Poulenc Chimie Catalytic hydrogenation of nitrile(s) to amine(s)
DE19500222A1 (en) * 1995-01-05 1996-07-11 Basf Ag Process for the simultaneous production of caprolactam and hexamethylenediamine

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1543973A1 (en) * 1966-06-08 1970-02-05 Vickers Zimmer Ag Method for purifying hexamethylenediamine
US3652545A (en) * 1969-11-28 1972-03-28 Celanese Corp Process for preparing n-(6-aminohexyl) hexamethyleneimine
FR2722784A1 (en) * 1994-07-21 1996-01-26 Rhone Poulenc Chimie Catalytic hydrogenation of nitrile(s) to amine(s)
DE19500222A1 (en) * 1995-01-05 1996-07-11 Basf Ag Process for the simultaneous production of caprolactam and hexamethylenediamine

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 80, no. 15, 15 April 1974, Columbus, Ohio, US; abstract no. 81945p, KASHNIKOV, A. M. ET AL.: "Selection of working pressure during vacuum fractionation." page 319; column 1; XP002063061 *
DATABASE WPI Week 6800, Derwent World Patents Index; AN 68-08724Q, XP002063062 *
DATABASE WPI Week 7236, Derwent World Patents Index; AN 72-56935T, XP002063063 *
TR. GOS. NAUCH.-ISSLED. PROCKT. INST. AZOTN. PROM. PROD. ORG. SIN., vol. 15, 1972, pages 160 - 163 *

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