DE2104756A1 - Fluorinated alkyl and alkeyl etherpretrifluoride from alkyl - and cobalt - Google Patents

Abstract

Fluorinated ethers R1-O-R2 (where R1 and R2 each are 1-6 (1-4)C fluorinated alk(en)yl, in which at least half of all H atoms present are replaced by F atoms and no more than 2 F atoms are linked to each C), are prepared by contacting alkyl ethers, pref. diethyl ether, in gas-phase with CoF3, pref. at 40-60 degrees C. The fluoralkyl ether(s) formed are treated, if alkenyl ethers are desired, with a strong base which splits off HF, pref. NaOH. Products are pref. used as inhalation anaesthetics, and the alkenyl ether derivs. can be polymerised to F-containing polymers.

Description

Description of the patent application relating to "Fluorinated Ether "The compound relates to fluorine compounds and especially fluorinated ethers.

The fluorinated ethers of the invention are fluorinated lower alkyl or lower alkenyl ethers of the general formula R1 O O-R2 in which R1 and R2, respectively independently fluorinated lower alkyl or lower alkenyl groups with 1 to 6 and especially with 1 to 4 carbon atoms, in which at least half of all existing hydrogen atoms are replaced by fluorine atoms and on no more than 2 fluorine atoms are bonded to each carbon atom.

The invention also relates to a process for the preparation of the fluorinated ones Ether, which is characterized in that there is a lower alkyl ether in the Bringing gas phase with cobalt trifluoride. The emerging ether can be converted to a fluorinated lower alkenyl ether by adding it treated with a strong base that splits off hydrogen fluoride.

The compounds of the invention are useful as inhalation anesthetics suitable and the invention therefore also relates to a means for inhalation anesthesia, the one or more of the above-mentioned compounds in the vapor phase and in admixture with a physiologically suitable carrier such as air or other oxygen-containing Contains breathing gases.

The fluorinated alkenyl ethers according to the invention can with the help of a Vinyl polymerization process are polymerized, with valuable new fluorine-containing Polymer materials are created.

Particularly favorable fluorinated lower alkyl ethers can be obtained from diethyl ether for example by contacting diethyl ether with cobalt trifluoride, preferably at a temperature of 40 to 600C. The resulting mixture of compounds can be separated by fractional distillation.

Compounds made in accordance with the present invention can include 1,1,2,2,4,5-heptafluoro-3-oapentane, 1,1,2,4,5,5-hexafluoro-3-oxapentane (dl- and meso-), and 1,1,2,4,5-pentafluoro-3-oxapentane.

The fluorinated lower alkenyl ethers can be prepared by a suitable fluorinated lower alkyl ether with a strong base e.g. molten potassium hydroxide. For example, when 1,1,2,4,5,5-hexafluoro-3-oxapentane is contacted with molten potassium hydroxide at about 2000C one dß-Trifluoräthoxy-Z-diffluoro rcithylen, ßß-Trifluorathoxy-E-difluoroethylene and bis (-Z-difluorovinyl) ethers.

The invention is illustrated in more detail by the following examples: Example 1: Fluorination of diethyl ether with cobalt trifluoride In a typical 150 g of diethyl ether were charged through a standard reaction vessel containing 6 kg of cobalt trifluoride entSelt, passed at 40-60 ° C, using 110 g of a mixture of fluorinated Ethanes and ethers received. The combined products of 8 batches (70 g) were fractionated and the following compounds were obtained from the mixture: (percent numbers based on the total mixture) (A) 1,2-difluoroethane boiling point 28.5 ° 4%; (B) 1,1,2,4,5,5-hexafluoro-3-oxapentane Bp 620 56, (c) dl- or meso-1,1,2,4,5,5-hexafluoro-3-oxapentane bp 81.5 ° 45%, (D) dl- or meso-1,1,2,4,5,5-hexafluoro-3-oxapentane bp 890 31%, (E) 1,1,2,4,5-hexafluoro-3-oxapentane Bp approx. 95 ° 3%. If the compound C or D is fluorinated again at 150 to 17,000 mainly compound B.

Compounds B, C, D and E were made in terms of their anesthetic Effectiveness according to the method of Burns et al in "Anästhesia" Vol. 16 No. 3, July Investigated in mice in 1961. Different concentrations of each of the compounds were made Administered to groups of 4 mice for half an hour. It turned out that the Mice quickly passed out when the compounds were administered and within regained consciousness about 5 minutes after the end of treatment. The mice were observed for an additional 48 hours and then sacrificed. It couldn't adverse effects of the treatment are noted.

Example 2: Elimination of hydrogen fluoride from 1,1,2,4,5,5-hexafluoro-3-oxapentane 5 es of oapentane was bubbled through molten potassium hydroxide at 210 ° C in a stream of nitrogen.

The product (4 g) contained 4 components. When separating by gas-liquid chromatography obtained in addition to the unreacted starting material (2 g) αßß-trifluoroethoxy-Z- (1g) (0.5g each) difluoroethylene and smaller amounts of ABß-trifluoroethoxy-E-difluoroethylene and bis - (- Z-difluorovinyl) ether, all by mass spectroscopy, elemental analysis and nuclear magnetic resonance spectra were characterized.

PATENTS? CLAIMS:

Claims (6)

Claims 1. Fluorinated ethers of the formula R1 - O-R2 in R1 and R2, independently of one another, are each fluorinated lower alkyl or lower alkenyl groups with 1 to 6, preferably 1 to 4 carbon atoms, at least the Half of all existing hydrogen atoms are replaced by fluorine atoms and attached to each Carbon atom no more than 2 fluorine atoms are bonded. 2. Process for the preparation of the fluorinated ethers according to claim 1, by noting that a lower alkyl ether is in the gas phase with cobalt trifluoride, and the resulting fluoroalkyl ether, if necessary treated with a strong base. 3. The method according to claim 2, characterized in that g e k e n n -z e i c h n e t that one starts from diethyl ether. 4. The method according to claim 2 or 3, characterized in that g e k e n n -Z e i c Not that you can start the reaction with cobalt trifluoride at a temperature in the range from 40 to 60 ° C. Method according to Claim 2, characterized in that that sodium hydroxide is used as the strong base. 6. Use of the fluorinated ethers according to claim 1 as inhalation anesthetics.