WO2001046122A1 - Purification of n,n-substituted amides of the trifluoroacetic acid - Google Patents

Purification of n,n-substituted amides of the trifluoroacetic acid Download PDF

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Publication number
WO2001046122A1
WO2001046122A1 PCT/EP2000/012591 EP0012591W WO0146122A1 WO 2001046122 A1 WO2001046122 A1 WO 2001046122A1 EP 0012591 W EP0012591 W EP 0012591W WO 0146122 A1 WO0146122 A1 WO 0146122A1
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Prior art keywords
water
trifluoroacetic acid
amides
purification
dialkylamides
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PCT/EP2000/012591
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German (de)
French (fr)
Inventor
Olaf BÖSE
Matthias Rieland
Dirk Seffer
Wolfgang Kalbreyer
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Solvay Fluor Und Derivate Gmbh
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Priority to AU25108/01A priority Critical patent/AU2510801A/en
Publication of WO2001046122A1 publication Critical patent/WO2001046122A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification

Definitions

  • the invention relates to a process for the purification of N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and of certain derivatives with cyclic amide groups.
  • Trifluoroacetyl-N, N-dimethylamide can be used as an electrolyte solvent for lithium batteries with increased safety (flame-retardant). A high degree of cleaning is required for these and other applications.
  • the object of the present invention is to provide a simple, energetically favorable process for the purification of N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and their amides, in which the nitrogen atom is integrated in a saturated ring system with 5 or 6 ring atoms , This object is achieved by the method of the present invention.
  • the process according to the invention for the purification of solvent-free N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and their amides, in which the nitrogen atom is incorporated in a saturated ring system, for the purpose of separating off water-soluble and hydrolyzable impurities, provides that the contaminated amide is also included Water contacts, so that the water-soluble impurities pass into the water, and then the organic phase is separated. There is no distillation.
  • the purified product obtained in this way can be used for those purposes in which low water contents in the amide do not interfere.
  • the water can optionally contain dissolved substances such as salts or alkalis.
  • the process according to the invention makes it possible to remove various organic water-soluble compounds which are present in the preparation, such as the corresponding carboxylic acid, trifluoroethanol, ethanol, cyclic amine and its salts, dialkylamine and its salts and hydrolyzable substances.
  • hydrolyzable substances particularly includes trifluoroacetic acid esters (especially the ethyl ester), trifluoroacetic anhydride or trifluoroacetic acid halides (e.g. the chloride).
  • these impurities form reaction products which dissolve easily in water.
  • these products are also removed in the process according to the invention (the substances formed in the water / amide system have a significantly larger distribution coefficient than the impurities originally present.
  • the amides to be purified by the process according to the invention can be prepared without solvents by z. B. generated by reacting the amine with acid esters, chlorides or anhydrides in the absence of a solvent.
  • the aqueous phase and the organic phase are separated in a conventional manner, for example by decanting.
  • N, N-dimethyltrifluoroacetamide, for example, is the heavier phase.
  • the water content of the organic phase ie the A id
  • This product is useful as an electrolyte solvent for Li batteries.
  • the subsequent drying in the preferred embodiment is carried out with customary inert drying agents.
  • sorbent drying agents such as zeolites, in particular molecular sieves; Use silica gel and other drying oxidic materials. Salts which incorporate or otherwise bind water in their crystal lattice, such as sodium sulfate or P 4 O 10, can of course also be used .
  • the amount of drying agent to be used depends on the desired drying time and the desired residual water content.
  • a particularly preferred drying agent for example 5 to 15 g of molecular sieve are used per 100 g of the amide.
  • the residual water content in N, N-dimethyltrifluoroacetamide, for example is only a few ppm. Free acid is no longer detectable analytically.
  • N, N-dialkylamides in which alkyl is C1-C3-alkyl groups, preferably methyl, are preferably cleaned and dried.
  • the cleaning process is very particularly preferably applied to N, N-dimethyltrifluoroacetamide.
  • the method is also advantageous in that an energy-intensive distillative cleaning can be dispensed with.
  • Another object of the invention are the amides specified in claim 4, in particular high-purity N, N-dimethyltrifluoroacetamide with a water content of max. 6 ppm.
  • N, N-dimethyltrifluoroacetamide contaminated with trifluoroacetic acid were extracted three times with 20 ml of water, the lower phase being formed by N, N-dimethyltrifluoroacetamide.
  • the aqueous phases were separated off and discarded.
  • the water content of the N, N-dimethyltrifluoroacetamide was 1.9% at 20 ° C.
  • the water content was determined by Karl Fischer titration.
  • the N, N-dimethyltrifluoroacetamide was dried using a 4 ⁇ molecular sieve. 15 g of molecular sieve A4 were added and the mixture was shaken several times. After a drying time of 24 hours, the residual water content in the N, N-dimethyltrifluoroacetamide was only 6 ppm. Free acid was no longer detectable analytically in N, N-dimethyltrifluoroacetamide.
  • N, N-dimethyltrifluoroacetamide was stored for one month at room temperature over a 4 ⁇ molecular sieve. No changes could be detected by gas chromatography. This proves that the compound is very stable against molecular sieve 4 ⁇ and that this therefore represents a very good drying agent for the trifluoroacetamide produced.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Abstract

N,N-dialkylamides of the trifluoroacetic acid and the perfluoroethane carboxylic acid and the amides thereof and of cyclic amines can be purified by washing using water for separating water-soluble and hydrolysable contaminations, whereby distillation is not required. The water content can be reduced to single-digit ppm values by drying using a molecular sieve 4 Å for instance. The inventive method is particularly suitable for purifying trifluoroacetyl-N,N-dimethylamide which can be used as an electrolyte solvent in lithium batteries.

Description

REINIGUNG VON N-N-SUBSTITUIERTEN AMIDEN DER TRIFLUORESSIGSÄURE PURIFICATION OF N-N-SUBSTITUTED AMIDES OF TRIFLUOROACETIC ACID
Beschreibungdescription
Die Erfindung bezieht sich auf ein Verfahren zur Reinigung von N,N-Dialkylamiden der Trifluoressigsäure und der Perfluorethancarbonsäure und von bestimmten Derivaten mit cyclischen Amid-Gruppen .The invention relates to a process for the purification of N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and of certain derivatives with cyclic amide groups.
Trifluoracetyl-N, N-dimethylamid ist als Elektrolyt- Lösungsmittel für Lithium-Batterien mit erhöhter Sicherheit (schwerentflammbar) brauchbar. Für diesen und andere Anwendungszwecke ist ein hoher Reinigungsgrad von Nöten. Aufgabe der vorliegenden Erfindung ist es, ein einfaches, energetisch günstiges Verfahren zur Reinigung von N, N-Dialkylamiden der Trifluoressigsäure und der Perfluorethancarbonsäure und deren Amide, in welchen das Sticksto fatom in ein gesättigtes Ringsystem mit 5 oder 6 Ring-Atomen eingebunden ist, anzugeben. Diese Aufgabe wird durch das Verfahren der vorliegenden Erfindung gelöst.Trifluoroacetyl-N, N-dimethylamide can be used as an electrolyte solvent for lithium batteries with increased safety (flame-retardant). A high degree of cleaning is required for these and other applications. The object of the present invention is to provide a simple, energetically favorable process for the purification of N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and their amides, in which the nitrogen atom is integrated in a saturated ring system with 5 or 6 ring atoms , This object is achieved by the method of the present invention.
Das erfindungsgemäße Verfahren zur Reinigung von lösungsmittelfrei vorliegenden N, N-Dialkylamiden der Trifluoressigsäure und der Perfluorethancarbonsäure und deren Amiden, in welchen das Stickstoffatom in ein gesättigtes Ringsystem eingebunden ist, zwecks Abtrennung wasserlöslicher und hydro- lysierbarer Verunreinigungen sieht vor, daß man das verunreinigte Amid mit Wasser kontaktiert, so daß die wasserlöslichen Verunreinigungen in das Wasser übergehen, und man sodann die organische Phase abtrennt. Eine Destillation erfolgt nicht. Das derart erhaltene gereinigte Produkt kann für jenen Zwecke eingesetzt werden, bei welchen geringe Gehalte an Wasser im Amid nicht stören. Dabei kann das Wasser gegebenenfalls Substanzen wie Salze oder Laugen gelöst enthalten.The process according to the invention for the purification of solvent-free N, N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid and their amides, in which the nitrogen atom is incorporated in a saturated ring system, for the purpose of separating off water-soluble and hydrolyzable impurities, provides that the contaminated amide is also included Water contacts, so that the water-soluble impurities pass into the water, and then the organic phase is separated. There is no distillation. The purified product obtained in this way can be used for those purposes in which low water contents in the amide do not interfere. The water can optionally contain dissolved substances such as salts or alkalis.
Das erfindungsgemäße Verfahren gestattet es, verschiedene organische, herstellungsbedingt vorhandene wasserlösliche Verbindungen wie die entsprechende Carbonsäure, Trifluoretha- nol, Ethanol, cyclisches Amin und dessen Salze, Dialkylamin und dessen Salze sowie hydrolysierbare Substanzen zu entfernen.The process according to the invention makes it possible to remove various organic water-soluble compounds which are present in the preparation, such as the corresponding carboxylic acid, trifluoroethanol, ethanol, cyclic amine and its salts, dialkylamine and its salts and hydrolyzable substances.
Der Begriff "hydrolysierbare Substanzen" umfaßt insbesondere Trifluoressigsäureester (besonders den Ethylester) , Trifluoressigsäureanhydrid oder Trifluoressigsäurehalogenide (z. B. das Chlorid). Diese Verunreinigungen bilden infolge der zu beobachtenden Hydrolyse Reaktionsprodukte, die sich leicht in Wasser lösen. Diese Produkte werden beim erfindungsgemäßen Verfahren mit entfernt (die gebildeten Stoffe besitzen im System Wasser/Amid einen deutlich größeren Verteilungskoeffizienten als die ursprünglich vorliegenden Verunreinigungen.The term "hydrolyzable substances" particularly includes trifluoroacetic acid esters (especially the ethyl ester), trifluoroacetic anhydride or trifluoroacetic acid halides (e.g. the chloride). As a result of the hydrolysis observed, these impurities form reaction products which dissolve easily in water. These products are also removed in the process according to the invention (the substances formed in the water / amide system have a significantly larger distribution coefficient than the impurities originally present.
Die nach dem erfindungsgemäßen Verfahren zu reinigenden Amide können lösungsmittelfrei hergestellt werden, indem man sie z. B. durch Umsetzung des Amins mit Säureestern, -Chloriden oder -anhydriden in Abwesenheit eines Lösungsmittels erzeugt .The amides to be purified by the process according to the invention can be prepared without solvents by z. B. generated by reacting the amine with acid esters, chlorides or anhydrides in the absence of a solvent.
Zweckmäßig fördert man den Stoffaustausch durch intensives Schütteln, Rühren, Führen über Kontaktkörper und andere bekannte Methoden.The exchange of substances is expediently promoted by intensive shaking, stirring, guiding over contact bodies and other known methods.
Die wäßrige Phase und die organische Phase werden in üblicher Weise getrennt, beispielsweise durch Dekantieren. N,N- Dimethyltrifluoracetamid stellt beispielsweise die schwerere Phase dar. In einer bevorzugten Ausführungsform wird der Wassergehalt der organischen Phase (d. h. des A ids) verringert. Dies Produkt ist als Elektrolytlösungsmittel für Li-Batterien brauchbar .The aqueous phase and the organic phase are separated in a conventional manner, for example by decanting. N, N-dimethyltrifluoroacetamide, for example, is the heavier phase. In a preferred embodiment, the water content of the organic phase (ie the A id) is reduced. This product is useful as an electrolyte solvent for Li batteries.
Die in der bevorzugten Ausführungsform sich anschließende Trocknung wird mit üblichen inerten Trocknungsmitteln durchgeführt. Beispielsweise kann man sorptiv arbeitende Trocknungsmittel wie Zeolithe, insbesondere Molekularsieb; Kieselgel und andere trocknend wirkende oxidische Materialien einsetzen. Brauchbar sind natürlich auch Salze, die Wasser in ihr Kristallgitter einbauen oder anders binden, wie Natriumsulfat bzw. P4O10.The subsequent drying in the preferred embodiment is carried out with customary inert drying agents. For example, sorbent drying agents such as zeolites, in particular molecular sieves; Use silica gel and other drying oxidic materials. Salts which incorporate or otherwise bind water in their crystal lattice, such as sodium sulfate or P 4 O 10, can of course also be used .
Die einzusetzende Menge an Trocknungsmittel richtet sich nach der gewünschten Trocknungszeit und dem gewünschten Restwassergehalt. Bei Verwendung von Molekularsieb 4 Ä, einem besonders bevorzugten Trocknungsmittel, setzt man beispielsweise 5 bis 15 g Molekularsieb pro 100 g des Amids ein. Nach einer mehrstündigen Trocknungszeit beträgt der Restwassergehalt beispielsweise in N, N-Dimethyltrifluoracetamid nur noch wenige ppm. Freie Säure ist analytisch nicht mehr nachweisbar.The amount of drying agent to be used depends on the desired drying time and the desired residual water content. When using 4 Å molecular sieve, a particularly preferred drying agent, for example 5 to 15 g of molecular sieve are used per 100 g of the amide. After a drying time of several hours, the residual water content in N, N-dimethyltrifluoroacetamide, for example, is only a few ppm. Free acid is no longer detectable analytically.
Bevorzugt reinigt und trocknet man N,N-Dialkylamide, in welchen Alkyl für Cl-C3-Alkylgruppen, vorzugsweise für Methyl steht. Ganz besonders bevorzugt wendet man das Reinigungsverfahren auf N, N-Dimethyltrifluoracetamid an.N, N-dialkylamides in which alkyl is C1-C3-alkyl groups, preferably methyl, are preferably cleaned and dried. The cleaning process is very particularly preferably applied to N, N-dimethyltrifluoroacetamide.
Man kann aber auch Amide der Trifluoressigsäure und der Perfluorethancarbonsäure reinigen und trocknen, in welchen der Stickstoff der Amidgruppe in ein gesättigtes 5- oder 6- Ringsystem eingebaut ist. Beispielsweise kann man das Morpho- linid, das Pyrrolidinid oder das Piperidinid der genannten Säuren reinigen und trocknen. Von besonderem Vorteil bei der Durchführung des erfindungsgemäßen Verfahrens ist der Umstand, daß die genannten Fluorcarbonsäureamide mit Wasser nicht mischbar sind und nicht hydrolysieren. Erstaunlicherweise sind diese Verbindungen auch bei Kontakt mit den Trocknungsmitteln wie Molekularsieb 4 Ä beständig. Beispielsweise wurde N, N-Dimethyltri- fluoracetamid monatelang über Molekularsieb 4 Ä aufbewahrt. Gaschromatographisch wurde keine Veränderung der Verbindung identifiziert .But you can also clean and dry amides of trifluoroacetic acid and perfluoroethane carboxylic acid, in which the nitrogen of the amide group is built into a saturated 5- or 6-ring system. For example, the morpholine, the pyrrolidinide or the piperidinide of the acids mentioned can be cleaned and dried. Of particular advantage when carrying out the process according to the invention is the fact that the fluorocarboxamides mentioned are immiscible with water and do not hydrolyze. Surprisingly, these compounds are stable even when they come into contact with drying agents such as 4 Å molecular sieves. For example, N, N-dimethyltrifluoroacetamide was stored for months over 4 Å molecular sieve. No change in the compound was identified by gas chromatography.
Das Verfahren ist weiterhin insofern vorteilhaft, als auf eine energieaufwendige destillative Reinigung verzichtet werden kann.The method is also advantageous in that an energy-intensive distillative cleaning can be dispensed with.
Ein weiterer Gegenstand der Erfindung sind die in Anspruch 4 angegebenen Amide, insbesondere hochreines N,N- Dimethyltrifluoracetamid mit einem Wassergehalt von max. 6 ppm.Another object of the invention are the amides specified in claim 4, in particular high-purity N, N-dimethyltrifluoroacetamide with a water content of max. 6 ppm.
Die folgenden Beispiele sollen die Erfindung weiter erläutern, ohne sie in ihrem Umfang einzuschränken.The following examples are intended to illustrate the invention without restricting its scope.
BeispieleExamples
Beispiel 1: Entfernung von aziden Komponenten und Wasser aus N, N-TrifluoracetamidenExample 1: Removal of acidic components and water from N, N-trifluoroacetamides
Reinigung von N, -DimethyltrifluoracetamidPurification of N, -dimethyltrifluoroacetamide
100 ml mit Trifluoressigsäure verunreinigtes N, N-Dimethyltri- fluoracetamid wurden dreimal mit 20 ml Wasser extrahiert, wobei die untere Phase durch N, N-Dimethyltrifluoracetamid gebildet wurde. Die wäßrigen Phasen wurde jeweils abgetrennt und verworfen. Nach dieser Behandlung betrug der Wassergehalt des N,N-Dimethyltrifluoracetamids 1,9 % bei 20 °C. Bestimmt wurde der Wassergehalt durch Karl-Fischer-Titration. Nach erfolgter Phasentrennung wurde das N, N-Dimethyltrifluoracetamid mit Hilfe von Molsieb 4 Ä getrocknet. Es wurden 15 g Molsieb A4 zugegeben und die Mischung mehrfach geschüttelt. Nach einer Trocknungszeit von 24 Stunden betrug der Restwassergehalt im N, N-Dimethyltrifluoracetamid lediglich 6 ppm. Freie Säure war im N, N-Dimethyltrifluoracetamid analytisch nicht mehr nachweisbar.100 ml of N, N-dimethyltrifluoroacetamide contaminated with trifluoroacetic acid were extracted three times with 20 ml of water, the lower phase being formed by N, N-dimethyltrifluoroacetamide. The aqueous phases were separated off and discarded. After this treatment, the water content of the N, N-dimethyltrifluoroacetamide was 1.9% at 20 ° C. The water content was determined by Karl Fischer titration. After phase separation, the N, N-dimethyltrifluoroacetamide was dried using a 4 Å molecular sieve. 15 g of molecular sieve A4 were added and the mixture was shaken several times. After a drying time of 24 hours, the residual water content in the N, N-dimethyltrifluoroacetamide was only 6 ppm. Free acid was no longer detectable analytically in N, N-dimethyltrifluoroacetamide.
Beispiel 2 : LangzeitstabilitätsversuchExample 2: Long-term stability test
N, N-Dimethyltrifluoracetamid wurde einen Monat bei Raumtemperatur über Molsieb 4 Ä gelagert. Gaschromatographisch konnten keine Veränderungen nachgewiesen werden. Dies belegt, daß die Verbindung sehr stabil gegenüber Molsieb 4 Ä ist und dieses daher ein sehr gutes Trocknungsmittel für das hergestellte Trifluoracetamid darstellt. N, N-dimethyltrifluoroacetamide was stored for one month at room temperature over a 4 Å molecular sieve. No changes could be detected by gas chromatography. This proves that the compound is very stable against molecular sieve 4 Å and that this therefore represents a very good drying agent for the trifluoroacetamide produced.

Claims

Patentansprüche claims
1. Verfahren zur Reinigung von lösungsmittelfrei vorliegenden N, N-Dialkylamiden der Trifluoressigsäure und der1. Process for the purification of solvent-free N, N-dialkylamides of trifluoroacetic acid and
Perfluorethancarbonsäure und deren Amiden mit gesättigten cyclischen A inen zwecks Abtrennung wasserlöslicher oder hydrolysierbarer Verunreinigungen, wobei man das verunreinigte Amid mit Wasser kontaktiert, so daß die wasserlöslichen bzw. hydrolysierbaren Verunreinigungen in das Wasser übergehen, und man sodann die organische Phase von der wäßrigen Phase abtrennt und gewünschtenfalls den Wassergehalt der organischen Phase verringert.Perfluoroethane carboxylic acid and its amides with saturated cyclic amines for the purpose of separating water-soluble or hydrolyzable impurities, wherein the contaminated amide is contacted with water so that the water-soluble or hydrolyzable impurities pass into the water, and then the organic phase is separated from the aqueous phase and if desired, the water content of the organic phase is reduced.
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man das gereinigte Amid im wesentlichen vollständig trocknet, vorzugsweise indem man es mit Silicagel, P4O10 oder Zeolithen, insbesondere mit Molekularsieb 4 Ä kontaktiert.2. The method according to claim 1, characterized in that the purified amide is substantially completely dried, preferably by contacting it with silica gel, P 4 O 10 or zeolites, in particular with 4 Å molecular sieve.
3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man N, N-Dimethyl-, N,N-Diethyl- oder N,N-Dipropylamid, das Morpholinid, Pyrrolidimid oder Piperidinid der Trifluor- essigsäure reinigt.3. The method according to claim 1, characterized in that N, N-dimethyl, N, N-diethyl or N, N-dipropylamide, the morpholinide, pyrrolidimide or piperidinide of trifluoroacetic acid is cleaned.
4. N, N-Dialkylamide und Amide mit cyclischen Aminen mit gesättigen 5- oder 6-Ringsystemen der Trifluoressigsäure und der Perfluorethancarbonsäure mit einem Wassergehalt von maximal 6 ppm. 4. N, N-dialkylamides and amides with cyclic amines with saturated 5- or 6-ring systems of trifluoroacetic acid and perfluoroethane carboxylic acid with a water content of at most 6 ppm.
PCT/EP2000/012591 1999-12-21 2000-12-12 Purification of n,n-substituted amides of the trifluoroacetic acid WO2001046122A1 (en)

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DE1999161747 DE19961747A1 (en) 1999-12-21 1999-12-21 N,N-dialkylamides of trifluoroacetic acid and perfluoroethane carboxylic acid, useful as electrolyte solvents for the production of lithium batteries, having a specific water content

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0239063A2 (en) * 1986-03-27 1987-09-30 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for preparing N-omega-trifluoroacetyl amino acid

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0239063A2 (en) * 1986-03-27 1987-09-30 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Process for preparing N-omega-trifluoroacetyl amino acid

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