WO2001046122A1 - Purification d"amides a substitution n-n de l"acide trifluoroacetique - Google Patents

Purification d"amides a substitution n-n de l"acide trifluoroacetique 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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WO
WIPO (PCT)
Prior art keywords
water
trifluoroacetic acid
amides
purification
dialkylamides
Prior art date
Application number
PCT/EP2000/012591
Other languages
German (de)
English (en)
Inventor
Olaf BÖSE
Matthias Rieland
Dirk Seffer
Wolfgang Kalbreyer
Original Assignee
Solvay Fluor Und Derivate Gmbh
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 Solvay Fluor Und Derivate Gmbh filed Critical Solvay Fluor Und Derivate Gmbh
Priority to AU25108/01A priority Critical patent/AU2510801A/en
Publication of WO2001046122A1 publication Critical patent/WO2001046122A1/fr

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Classifications

    • 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

Selon l"invention, des N,N-dialkylamides de l"acide trifluoroacétique et de l"acide perfluoroéthanecarboxylique et leurs amides d"amines cycliques peuvent être purifiés par un lavage avec de l"eau, lavage dont le but est de séparer tant les contaminants hydrosolubles que les contaminants hydrolysables, sans qu"il soit nécessaire de procéder à une distillation. Par séchage avec, par exemple, un tamis moléculaire de 4 Å, la teneur en eau peut être abaissée à une valeur de ppm à un seul chiffre. Ce procédé convient particulièrement bien à la purification de trifluoroacétyl-N,N-diméthylamide qui peut être utilisé comme solvant électrolytique dans des piles au lithium.
PCT/EP2000/012591 1999-12-21 2000-12-12 Purification d"amides a substitution n-n de l"acide trifluoroacetique WO2001046122A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU25108/01A AU2510801A (en) 1999-12-21 2000-12-12 Purification of n,n-substituted amides of the trifluoroacetic acid

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19961747.3 1999-12-21
DE1999161747 DE19961747A1 (de) 1999-12-21 1999-12-21 Reinigung von N,N-substituierten Amiden

Publications (1)

Publication Number Publication Date
WO2001046122A1 true WO2001046122A1 (fr) 2001-06-28

Family

ID=7933637

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/012591 WO2001046122A1 (fr) 1999-12-21 2000-12-12 Purification d"amides a substitution n-n de l"acide trifluoroacetique

Country Status (3)

Country Link
AU (1) AU2510801A (fr)
DE (1) DE19961747A1 (fr)
WO (1) WO2001046122A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0239063A2 (fr) * 1986-03-27 1987-09-30 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Procédé pour la fabrication de l'amino-acide N oméga-trifluoroacétyl

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0239063A2 (fr) * 1986-03-27 1987-09-30 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Procédé pour la fabrication de l'amino-acide N oméga-trifluoroacétyl

Also Published As

Publication number Publication date
DE19961747A1 (de) 2001-06-28
AU2510801A (en) 2001-07-03

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