DE1219491B - Process for the recovery of 1, 4-diazabicyclo [2, 2, 2] octane and piperazine - Google Patents
Process for the recovery of 1, 4-diazabicyclo [2, 2, 2] octane and piperazineInfo
- Publication number
- DE1219491B DE1219491B DEC30419A DEC0030419A DE1219491B DE 1219491 B DE1219491 B DE 1219491B DE C30419 A DEC30419 A DE C30419A DE C0030419 A DEC0030419 A DE C0030419A DE 1219491 B DE1219491 B DE 1219491B
- Authority
- DE
- Germany
- Prior art keywords
- piperazine
- octane
- diazabicyclo
- fraction
- recrystallization
- 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.)
- Pending
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims description 44
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 13
- 238000011084 recovery Methods 0.000 title claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- 239000012452 mother liquor Substances 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- CWPIBZMCMRNFHK-UHFFFAOYSA-N piperazin-1-ium;carbamate Chemical compound NC(O)=O.C1CNCCN1 CWPIBZMCMRNFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- VARKIGWTYBUWNT-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanol Chemical compound OCCN1CCN(CCO)CC1 VARKIGWTYBUWNT-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 piperazine 1,4-Diazabicyclo [2.2.2] octane Chemical compound 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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
- C07D295/027—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 containing only one hetero ring
-
- 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
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
-
- 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Gewinnung von 1,4-Diazabicyclo [2,2,2]octan und Piperazin 1,4-Diazabicyclo[2,2,2]octan wird bekanntlich aus N-(ß-Hydroxyäthyl)-piperazin oder N,N'-Bis-(ß-hydrox..yäthyl)ipe'razin hergestellt.Process for the recovery of 1,4-diazabicyclo [2.2.2] octane and piperazine 1,4-Diazabicyclo [2.2.2] octane is known to be obtained from N- (ß-hydroxyethyl) piperazine or N, N'-bis (ß-hydrox..yäthyl) ipe'razin produced.
Die Aufarbeitung des Reaktionsgemisches erfolgt zunächst durch fraktionierte Destillation,.wobei die zwischen 130 und l90°C siedende Fraktion praktisch das gesamte entstandene 1,4-Diazabicyclo[2,2,2]octan enthält. Daneben sirfl darin noch etwa 10 bis 15°lo Piperazin und etwa 15 % zahlreiche weitere Umsetzungsprodukte enthalten. Bei der weiteren fraktionierten Destiltation kann das 1,4-Diazabicyclo[2,2,2]octan nur in geringen Ausbeuten und nur in einer Reinheit von etwa 9001o aus der genannten Fraktion gewonnen werden. The reaction mixture is first worked up by fractionated Distillation, where the fraction boiling between 130 and 190 ° C is practically the whole resulting 1,4-diazabicyclo [2.2.2] octane. In addition, it sirfl about 10 to 15 ° lo piperazine and about 15% contain numerous other reaction products. In the further fractional distillation, the 1,4-diazabicyclo [2.2.2] octane only in low yields and only in a purity of about 9001o from the mentioned Faction to be won.
Man hat auch bereits 'vor'geschlagen, aus der zwischen 130 und l90aC siedenden Fraktion das 1,4-Diazabicyclo[2,2,2]octan durch Umkristallisieren aus Aceton oder iLthylacetat zu gewinnen; Nach diesem Verfahren erhält man zwar bis zu 750/o des darin enthaltenen 1,4-Diazabicyclo[2,2,2]octans in etwa 95%iger Reinheit. Die weitere Aufarbeitung der verbleibenden Mutterlauge gelingt jedoch nur in vielstufiger Kristallisation, wobei das 1,4-Diazabicyclot2,2,2]octan schließlich ebenfalls sur in höchstens 95%iger Reinheit anfällt. Außerdem haben die genannten Verfahren den Nachteil, daß das in der Rohfraktion enthaltene Piperazin zum großen Teil verlorengeht. It has already been suggested, from between 130 and 190aC the 1,4-diazabicyclo [2.2.2] octane from the boiling fraction by recrystallization To obtain acetone or ethyl acetate; With this method you get up to to 750 / o of the 1,4-diazabicyclo [2.2.2] octane contained therein in about 95% purity. However, the remaining mother liquor can only be worked up in multiple stages Crystallization, whereby the 1,4-diazabicyclot2,2,2] octane finally also sur is obtained in a maximum of 95% purity. In addition, the procedures mentioned have the Disadvantage that the piperazine contained in the crude fraction is largely lost.
Der Vorschlag, das Piperazin zunächst als Acetat abzutrennen, führt zu technisch nicht tragbaren Essigsäureverlusten, da eine Wiedergewinnung der Esslgsäure in wirtschaftlicher Weise aus dem Umsetzungsgemisch nicht möglich ist. The proposal to first separate the piperazine as acetate leads to technically unacceptable loss of acetic acid, since the acetic acid is recovered is not economically feasible from the conversion mixture.
Es wurde nun ein Verfahren zur Gewinnung von 1,4-Diazabicyclo[2,2,2]octan und Piperazin gefunden, das darin besteht, daß man die zwischen 130 und 190°C siedende Fraktion, die durch in bekannter Weise, durchgeführte Umsetzung pon N-(ß-Hydroxyäthyl)-piperazin oder N,N'-Bis-(ß-hydroxyäthyl)-pierazin zu 1,4-Diazabicyclo[2,2,2]octan und anschlieende fraktionierte Destillation des Reaktionsgemisches erhalten worden ist, in Gegenwart eines organischen Lösungsmittels mit Kohlendioxyd behandelt, das ausgefallene Piperazincarbamat abtrennt, durch Erhitzen in Piperazin überführt, dieses in an sich bekannter Weise durch Umkristallisieren reinigt und aus der Mutter lauge des Piperazincarbamats, gegebenenfalls nach Abtrennen des Lösungsmittels, das 1,4-Diazabicyclo[2,2,2]octan in an sich bekannter Weise durch Umkristallisieren gewinnt. There has now been a process for the recovery of 1,4-diazabicyclo [2.2.2] octane and piperazine found, which consists in the fact that one boils between 130 and 190 ° C Fraction, which by in a known manner, carried out reaction pon N- (ß-hydroxyethyl) piperazine or N, N'-bis (ß-hydroxyethyl) -pierazine to 1,4-diazabicyclo [2.2.2] octane and then fractional distillation of the reaction mixture has been obtained in the presence treated with carbon dioxide of an organic solvent, the precipitated piperazine carbamate separated off, converted into piperazine by heating, this in a manner known per se Purifies by recrystallization and from the mother liquor of the piperazine carbamate, optionally after separating off the solvent, the 1,4-diazabicyclo [2.2.2] octane wins in a known manner by recrystallization.
Aus der nach der Kohlendioxydbehandlung anfallenden Mutterlauge wird das 1,4-Diazabicyclo[2,2,2]-octan nach einmaligem Umkristallisieren in etwa 99%iger Reinheit erhtalten. The mother liquor obtained after the carbon dioxide treatment becomes the 1,4-diazabicyclo [2,2,2] octane after recrystallization once in about 99% Maintain purity.
Das Verfahren wird im allgemeinen in folgender Weise durchgeführt: Die zwischen 130 und 190°C siedende Fraktion, die etwa 70% 1,4-Diazabicyclo[2,2,2]octan und 10 bis 15 0/o Piperazin enthält, wird in einem organischen Lösungsmittel, wie Benzol, Toluol, Äthylbenzol, Äthylacetat oder Aceton, aufgenommen. The procedure is generally carried out in the following way: The fraction boiling between 130 and 190 ° C, which is about 70% 1,4-diazabicyclo [2.2.2] octane and 10 to 15 0 / o contains piperazine is in an organic solvent such as Benzene, toluene, ethylbenzene, ethyl acetate or acetone, added.
Die Konzentration der Lösung soll etwa 25°/o betragen, kann jedoch auch größer oder kleiner sein. The concentration of the solution should be about 25%, but it can also be bigger or smaller.
In die Lösung wird Kohlendioxyd eingeleitet, bis keine Fällung mehr stattfindet. Das ausgefallene Piperazincarbamat wird dann durch Filtrieren oder Zentrifugieren abgetrennt. Carbon dioxide is passed into the solution until no more precipitation takes place. The precipitated piperazine carbamate is then filtered or Separated by centrifugation.
Aus der verbleibenden Mutterlauge wird gegebenenfalls nach Abtrennen des Lösungsmittels in an sich bekannter Weise durch Umkristallisieren aus Äthylacetat oder Aceton 1,4-Diazabicyclo[2,2,2]octan in einer Reinheit von etwa 99% gewonnen. The remaining mother liquor is optionally after separation of the solvent in a manner known per se by recrystallization from ethyl acetate or acetone 1,4-diazabicyclo [2.2.2] octane is obtained in a purity of about 99%.
Das ausgefallene rohe Piperazincarbamat enthält etwa 50 bis 60 °/0 Piperazin und 30% 1,4-Diazabicyclo-[2,2,2]octan und etwa 10% zahlreicher Nebenprodukte. The precipitated crude piperazine carbamate contains about 50 to 60% Piperazine and 30% 1,4-diazabicyclo- [2.2.2] octane and about 10% various by-products.
Das Rohprodukt wird auf etwa 130 bis 140°C erhitzt, um das Carbamat zu spalten; Anschließend wird das verbleibende rohe Piperazin durch Umkristallisieren, z. B. aus Dioxan, in Piperazin mit einer -Reinheit von etwa 95 bis 96% übergeführt.The crude product is heated to about 130 to 140 ° C to produce the carbamate to split; The remaining crude piperazine is then recrystallized, z. B. from dioxane, converted into piperazine with a purity of about 95 to 96%.
Nach dem Abtrennen des zur Kristallisation verwendeten Lösungsmittels wird der Rückstand mit der Mutterlauge aus der Umkristallisierung des 1,4-Diazabicyclo[2,2,2]octans 'vereinigt. After separating off the solvent used for crystallization the residue with the mother liquor from the recrystallization of 1,4-diazabicyclo [2.2.2] octane 'united.
Diese Mischung wird so weit eingeengt, däß nur noch etwa 1 bis 5% des ursprünglich eingesetzten Lösungsmittels vorhanden sind. Die ausgefallene kristalline Fraktion wird dann einer weiteren Charge der zwischen 130 und 190°C siedenden. Fraktion zugeführt und dieses Gemisch in der beschriebenen Weise einer weiteren Behandlung mit Kohlendioxyd unterworfen. This mixture is concentrated so that only about 1 to 5% of the solvent originally used are present. The unusual one crystalline Fraction is then used in another batch of the between 130 and 190 ° C boiling. fraction fed and this mixture in the manner described for further treatment subjected to carbon dioxide.
Bei fortlaufender Anwendung des Verfahrens werden 90 bis 95% des ursprünglich vorhandenen 1,4-Diazabicyclo[2,2,2]octans und 80 bis 90% des Piperazins in reiner Form gewonnen. Das Verfahren hat den Vorteil, daß das entstandene Piperazin nicht verlorengeht und daß des entstandene 1,4-Diazabicyclo[2,2,2]-octan schon nach der ersten Kristallisation in einer Reinheit von etwa 99°/e gewonnen wird, während es nach den bisherigen Verfahren nur in einer Reinheit von höchstens 95% bei der ersten Kristallisation erhalten worden war. With continued use of the procedure, 90 to 95% of the 1,4-diazabicyclo [2.2.2] octane originally present and 80 to 90% of the piperazine obtained in pure form. The process has the advantage that the resulting piperazine is not lost and that the 1,4-diazabicyclo [2,2,2] octane formed is already after the first crystallization is obtained in a purity of about 99 ° / e, during it according to the previous process only in a purity of at most 95% in the first crystallization had been obtained.
Aus Journ prakt. Chemie [2], 53, S. 24 (1896), ist es bekannt, daß beim Einleiten von Kohlendioxyd in eine alkoholische Lösung von Piperazin Piperazincarbamat ausfällt. Die bei 130 bis 190°C siedende, 1,SDiazabicyclo[2,2,2]octan und Piperazin enthaltende Fraktion, die im vorliegenden Verfahren verwendet wird, enthält noch zahlreiche weitere Umsetzungsprodukte (vgl. Spalte 1, Absatz 2). Es war daher. Auf Grund dieser komplexen Zusammensetzung der Fraktion nicht zu erwarten, daß aus der nach dem Ausfällen des Piperazincarbamates anfallenden Mutterlauge, die ebaenfils-J noch zahlreiche Nebenprodukte enthält, durch einmaliges Umkristallisieren 1,4-Diazabicyclo[2,2,2]octan in 99%iger Reinheit gewonnen werden konnte; um so mehr, da keineswegs zu erwarten war, daß unter den zahlreichen vorhandenen Nebinprodukten in der Rohfraktion gerade das darin enthaltene Piperazin die Ursache für die schwierige Reinigung darstellt. From Journ Prakt. Chemie [2], 53, p. 24 (1896), it is known that when introducing carbon dioxide into an alcoholic solution of piperazine piperazine carbamate fails. The 1, SDiazabicyclo [2.2.2] octane and piperazine boiling at 130 to 190 ° C containing fraction, which is used in the present process, still contains numerous other conversion products (see column 1, paragraph 2). It was therefore. on Because of this complex composition of the group is not to be expected from the after the precipitation of the piperazine carbamates resulting mother liquor, the ebaenfils-J still contains numerous by-products, 1,4-diazabicyclo [2.2.2] octane by recrystallization once could be obtained in 99% purity; all the more so as by no means to be expected was that among the numerous existing nebin products in the crude fraction the piperazine it contains is the cause of the difficult cleaning.
Beispiel Aus 500g der zwischen 130 und 190°C siedenden Fraktion des Reaktionsgemisches, die70,3 %1,4-Diazabicyclo[2,2,2]octan und 14a6°lo Piperazin enthält, wird eine 25%ige benzolische Lösung hergestellt und bis zur Beendigung der Fällung Kohlendioxyd eingeleitet. Example From 500 g of the fraction of des boiling between 130 and 190 ° C Reaction mixture containing 70.3% 1,4-diazabicyclo [2.2.2] octane and 14a6 ° lo piperazine a 25% benzene solution is made up and to completion carbon dioxide initiated the precipitation.
Die Fällung, die überwiegend aud rohem Piperazincarbamat (etwa 60°/o) besteht, wird abfiltriert, und aus der Mutterlauge wird das Benzol abgetrieben.The precipitation, which is mainly from crude piperazine carbamate (about 60%) consists, is filtered off, and the benzene is driven off from the mother liquor.
Die piperazinarme Fraktion 1, die etwa 80 bis 85°/o 1,4-Diazabicyclo[2,2,2]octan enthält, wird aus der 1,5fachen Gewichtsmenge Essigsäureäthylester umkristallisiert. Die anfallende Fraktion 3 ist 1,4-Diazabicyclo[2,2,2]octan mit einer Reinheit von 99,3%.The low-piperazine fraction 1, which is about 80 to 85% 1,4-diazabicyclo [2.2.2] octane contains, is recrystallized from 1.5 times the amount by weight of ethyl acetate. The resulting fraction 3 is 1,4-diazabicyclo [2.2.2] octane with a purity of 99.3%.
Die Fällung wird auf 130 bis 140°C erhitzt, bis kein Kohlendioxyd mehr entweicht. Diese Piperazin enthaltende Fraktion 2 wird aus der doppelten Gewichtsmenge Dioxan umkristallisiert, wobei reines Piperazin (Fraktion 4) anfällt. Die Mutterlauge wird eingedampft und der Rückstand mit der Mutterlauge der Fraktion 3 vereinigt. Diese Mischung wird fast bis zur Trockne eingedampft. Beim Erkalten fällt eine kristalline Fraktion (5) und eine Restmutterlauge (Fraktion 6) an, die ungefähr 10% Essigsäureäthylester enthalten soll.The precipitate is heated to 130 to 140 ° C until no carbon dioxide more escapes. This fraction 2 containing piperazine is made from twice the amount by weight Dioxane recrystallized, pure piperazine (fraction 4) being obtained. The mother liquor is evaporated and the residue is combined with the mother liquor from fraction 3. This mixture is evaporated almost to dryness. When it cools down, a crystalline one falls Fraction (5) and a residual mother liquor (fraction 6) containing about 10% ethyl acetate should contain.
Fraktion 5 wird mit weiteren 500 g der zwischen 130 und 190°C siedenden Fraktion, wie oben angegeben, behandelt. Die anfallende Fraktion 5 wird jeweils einer neuen Charge der Ausgangsfraktion zugeführt.Fraction 5 is boiled between 130 and 190 ° C with another 500 g Fraction, as indicated above, treated. The resulting fraction 5 is each fed to a new batch of the starting fraction.
In der folgenden Tabelle sind die Ergebnisse für die Verarbeitung
von sieben Chargen zusammengestellt, wobei in den Ausgangsgemischen 2 bis 7 jeweils
die Menge der vorangehenden Fraktion 5 enthalten ist:
Die vereinigten Fraktionen (6) enthalten 11% (67 g) Lösungsmittel und 535 g Trockensubstanz, die 93 g (3,8%, bezogen auf das Ausgangsmaterial) 1,4-Diazabicyclo[2,2,2]octan und 42 g Piperazin (8,2%, bezogen auf das Ausgangsmaterial) enthalten. The combined fractions (6) contain 11% (67 g) solvent and 535 g dry matter, which is 93 g (3.8% based on the starting material) 1,4-diazabicyclo [2.2.2] octane and 42 g of piperazine (8.2%, based on the starting material).
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30419A DE1219491B (en) | 1963-07-11 | 1963-07-11 | Process for the recovery of 1, 4-diazabicyclo [2, 2, 2] octane and piperazine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC30419A DE1219491B (en) | 1963-07-11 | 1963-07-11 | Process for the recovery of 1, 4-diazabicyclo [2, 2, 2] octane and piperazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1219491B true DE1219491B (en) | 1966-06-23 |
Family
ID=7019337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC30419A Pending DE1219491B (en) | 1963-07-11 | 1963-07-11 | Process for the recovery of 1, 4-diazabicyclo [2, 2, 2] octane and piperazine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1219491B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725681A (en) * | 1985-08-19 | 1988-02-16 | Ethyl Corporation | Production of triethylenediamine |
-
1963
- 1963-07-11 DE DEC30419A patent/DE1219491B/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4725681A (en) * | 1985-08-19 | 1988-02-16 | Ethyl Corporation | Production of triethylenediamine |
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