WO1997030959A1 - Synthesis of organic iodine-fluorine compounds - Google Patents

Synthesis of organic iodine-fluorine compounds Download PDF

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Publication number
WO1997030959A1
WO1997030959A1 PCT/FR1997/000153 FR9700153W WO9730959A1 WO 1997030959 A1 WO1997030959 A1 WO 1997030959A1 FR 9700153 W FR9700153 W FR 9700153W WO 9730959 A1 WO9730959 A1 WO 9730959A1
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Prior art keywords
iodide
iodo
compound
trifluoroethane
dimethyl
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PCT/FR1997/000153
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French (fr)
Inventor
Gilles Drivon
Jean-Philippe Gillet
Jean-Pierre Schirmann
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Elf Atochem S.A.
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Publication of WO1997030959A1 publication Critical patent/WO1997030959A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX

Definitions

  • the invention relates to the field of halogenated hydrocarbons and more particularly relates to the synthesis of iodo-fluorinated organic compounds from the corresponding chlorofluorinated compounds.
  • iodo-fluorinated compounds Due to the reactivity of their iodine atom, iodo-fluorinated compounds are important synthesis intermediates for the manufacture of pharmaceutical products, phytosanitary products, extinguishing agents and products for oleophobic and hydrophobic treatment.
  • various substrates such as textiles, leathers, papers, building materials.
  • 2-iodo-1, 1, 1-trifluoroethane (CF3CH2I) is often used to introduce the radical 1, 1, 1 -trif luoroéthy le into pharmaceu ⁇ tically active molecules.
  • CF3CH2I 2-iodo-1, 1, 1-trifluoroethane
  • Chlorofluorinated organic compounds such as 2-chloro-1, 1, 1-trifluoroethane are inexpensive products and are available industrially. It has now been found that, under certain conditions, their reaction with an alkaline iodide gives access to the iodo-fluorinated organic compounds, in a particularly simple manner and with excellent selectivity and yield.
  • the subject of the invention is therefore a process for the preparation of an iodo-fluorinated organic compound of general formula: Rp-CH2l in which Rp denotes a perfluoroalkyl radical, linear or branched, containing from 1 to 8 carbon atoms, characterized in that that the corresponding chlorofluorinated compound is reacted with an alkaline iodide in a polar aprotic solvent having a boiling point greater than that of the desired iodo-fluorinated compound.
  • the polar aprotic solvent is chosen for example from the group consisting of sulfolane (tetramethylene sulfone), N, N-dimethylformamide, dimethyl sulfoxide, N, N-dimethylacetamide, N-methylpyrrolidone, 1, 3-dimethyl -2-imidazolidinone, 1, 3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone and their mixtures.
  • sulfolane or 1,3-dimethyl-2-imidazolidinone is used.
  • the amount of solvent to be used depends on the embodiment chosen (discontinuous, semi-continuous or continuous) and on the intrinsic solubility of the alkaline iodide used. Generally from 1 to 75 parts by weight of alkali iodide per 100 parts by weight of solvent can be used, but preferably from 5 to 50 parts of alkali iodide per 100 parts of solvent are used.
  • Iodide of any alkali metal Li, Na, K, Rb, Cs
  • sodium iodide or potassium iodide can be used, but it is preferred to use sodium iodide or potassium iodide.
  • REMPIACEMEMT SHEET (RULE 26) molar of the chlorofluorinated compound Rp-CH2CI in alkaline iodide can vary within wide limits. It is generally between 1 and 10, preferably between 1 and 5.
  • chlorofluorinated compounds Rp-CH2Cl there may be mentioned more particularly 2-chloro-1, 1, 1-trifluoroethane, 3-chloro-1, 1, 1, 2,2-pentafluoropropane, 3-chloro -1, 1, 1, 2-tetrafluoro-2-trifluoromethylpropane.
  • the reaction temperature can vary within wide limits. It is generally between room temperature and the boiling point of the solvent used, preferably between 50 and 250X.
  • the temperature is to be chosen according to the reactivity of the starting chlorofluorinated compound; thus, in the case of 2-chloro-1, 1, 1-trifluoroethane, the operation is advantageously between 100 and 230 ° C, preferably between 180 and 220 ° C. It is preferred to work at atmospheric pressure, but it would not depart from the scope of the present invention by operating at lower or higher pressure.
  • the reactor is first charged with alkaline iodide and the polar aprotic solvent, then after having brought the reaction medium under stirring and to the chosen temperature, continuously introducing the chlorofluorinated compound and continuously withdrawing a gaseous vent consisting of a mixture of the desired iodo-fluorinated compound and the unreacted chlorofluorinated compound.
  • the latter can be separated from the iodo-fluorinated compound by simple distillation and recycled to the reactor.
  • the operation is carried out in the same manner as previously for the semi-continuous process, but the liquid phase is further drawn off which is filtered to remove the alkali chloride. trained; the filtrate is recycled to the reactor after adding an alkaline iodide supplement.
  • EXAMPLE 1 In a glass reactor with a capacity of 500 ml, equipped with a stirring device (turbine type), a heating device and a temperature regulation system, 200 g of 1, 3-dimethyl-2-imidazolidinone (DMI) and 45 g (0.3 mole) of sodium iodide. The reaction medium is brought to 210 ° C. with stirring. tion, then continuously introduced 2-chloro-1, 1, 1-trifluoroethane in gaseous form at atmospheric pressure, by means of an introduction rod at the bottom of the reactor. The average flow rate is around 40 g / h.
  • DMI 1, 3-dimethyl-2-imidazolidinone
  • the 2-iodo-1, 1, 1-trifluoroethane is recovered as it is formed by condensation of the gaseous "vents". After 3 hours of reaction, a conversion of 89% of the sodium iodide is obtained and a yield of 2-iodo-1,1,1-trifluoroethane of 86% relative to the Nal used.
  • Example 1 was repeated, but replacing the DMI with the same amount of sulfolane and increasing the time for the introduction of 2-chloro-1, 1, 1, -trifluoroethane to 5 hours to 5 hours. 40 g / h.
  • Example 1 was repeated, but replacing the sodium iodide with 35.7 g (0.3 mole) of potassium bromide. After 3 hours of reaction, the conversion of potassium bromide was

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An organic iodine-fluorine compound such as CF3CH2l may be prepared by reacting the corresponding chlorine-fluorine compound with an alkaline iodide in a polar aprotic solvent having a higher boiling point than the desired iodine-fluorine compound.

Description

SYNTHESE DE COMPOSES ORGANIQUES IODO-FLUORES SYNTHESIS OF IODO-FLUORINATED ORGANIC COMPOUNDS
L'invention concerne le domaine des hydrocarbures halogènes et a plus particulièrement pour objet la synthèse de composés organiques iodo-fluorés à partir des composés chlorofluorés correspondants.The invention relates to the field of halogenated hydrocarbons and more particularly relates to the synthesis of iodo-fluorinated organic compounds from the corresponding chlorofluorinated compounds.
En raison de la réactivité de leur atome d'iode, les composés iodo-fluorés sont d'importants intermédiaires de synthèse pour la fabrication de produits pharma¬ ceutiques, de produits phytosanitaires, d'agents extincteurs et de produits pour le traitement oléophobe et hydrophobe de divers substrats tels que textiles, cuirs, papiers, matériaux de construction.Due to the reactivity of their iodine atom, iodo-fluorinated compounds are important synthesis intermediates for the manufacture of pharmaceutical products, phytosanitary products, extinguishing agents and products for oleophobic and hydrophobic treatment. various substrates such as textiles, leathers, papers, building materials.
Ainsi, par exemple, le 2-iodo-1 ,1 ,1-trifluoroéthane (CF3CH2I) est souvent utilisé pour introduire le radical 1 ,1 ,1 -trif luoroéthy le dans des molécules pharmaceu¬ tiquement actives. On connaît plusieurs modes de synthèse de ce composé iodo- fluoré, mais les méthodes décrites à ce jour sont difficiles à mettre en oeuvre indus- triellement ou font appel à des matières premières onéreuses.Thus, for example, 2-iodo-1, 1, 1-trifluoroethane (CF3CH2I) is often used to introduce the radical 1, 1, 1 -trif luoroéthy le into pharmaceu¬ tically active molecules. Several modes of synthesis of this iodofluorinated compound are known, but the methods described to date are difficult to carry out industrially or use expensive raw materials.
Les composés organiques chlorofluorés tels que le 2-chloro-1 ,1 ,1-trifluoroé- thane sont des produits peu coûteux et disponibles industriellement. Il a maintenant été trouvé que, dans certaines conditions, leur réaction avec un iodure alcalin permet d'accéder aux composés organiques iodo-fluorés, de manière particulièrement simple et avec une sélectivité et un rendement excellents.Chlorofluorinated organic compounds such as 2-chloro-1, 1, 1-trifluoroethane are inexpensive products and are available industrially. It has now been found that, under certain conditions, their reaction with an alkaline iodide gives access to the iodo-fluorinated organic compounds, in a particularly simple manner and with excellent selectivity and yield.
L'invention a donc pour objet un procédé de préparation d'un composé organique iodo-fluoré de formule générale : Rp-CH2l dans laquelle Rp désigne un radical perfluoroalkyle, linéaire ou ramifié, contenant de 1 à 8 atomes de carbone, caractérisé en ce que l'on fait réagir le composé chlorofluoré correspondant avec un iodure alcalin au sein d'un solvant aprotique polaire ayant un point d'ébuliition supé¬ rieur à celui du composé iodo-fluoré désiré.The subject of the invention is therefore a process for the preparation of an iodo-fluorinated organic compound of general formula: Rp-CH2l in which Rp denotes a perfluoroalkyl radical, linear or branched, containing from 1 to 8 carbon atoms, characterized in that that the corresponding chlorofluorinated compound is reacted with an alkaline iodide in a polar aprotic solvent having a boiling point greater than that of the desired iodo-fluorinated compound.
On choisit le solvant aprotique polaire par exemple dans le groupe constitué par le sulfolane (tétraméthylène sulfone), le N,N-diméthylformamide, le diméthylsul- foxyde, le N,N-diméthylacétamide, la N-méthylpyrrolidone, la 1 ,3-diméthyl-2-imidazo- lidinone, la 1 ,3-diméthyl-3,4,5,6-tétrahydro-2-pyrimidinone et leurs mélanges. De préférence, on utilise le sulfolane ou la 1 ,3-diméthyl-2-imidazolidinone.The polar aprotic solvent is chosen for example from the group consisting of sulfolane (tetramethylene sulfone), N, N-dimethylformamide, dimethyl sulfoxide, N, N-dimethylacetamide, N-methylpyrrolidone, 1, 3-dimethyl -2-imidazolidinone, 1, 3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone and their mixtures. Preferably, sulfolane or 1,3-dimethyl-2-imidazolidinone is used.
La quantité de solvant à mettre en oeuvre dépend du mode de réalisation choisi (discontinu, semi-continu ou continu) et de la solubilité intrinsèque du iodure alcalin utilisé. On peut généralement employer de 1 à 75 parties en poids d'iodure alcalin pour 100 parties en poids de solvant, mais on utilise de préférence de 5 à 50 parties d'iodure alcalin pour 100 parties de solvant.The amount of solvent to be used depends on the embodiment chosen (discontinuous, semi-continuous or continuous) and on the intrinsic solubility of the alkaline iodide used. Generally from 1 to 75 parts by weight of alkali iodide per 100 parts by weight of solvent can be used, but preferably from 5 to 50 parts of alkali iodide per 100 parts of solvent are used.
On peut employer l'iodure de n'importe quel métal alcalin (Li, Na, K, Rb, Cs), mais on préfère utiliser l'iodure de sodium ou l'iodure de potassium. Le rapportIodide of any alkali metal (Li, Na, K, Rb, Cs) can be used, but it is preferred to use sodium iodide or potassium iodide. The report
FEUILLE DE REMPIACEMEMT (REGLE 26) molaire du composé chlorofluoré Rp-CH2CI en iodure alcalin peut varier dans de larges limites. Il est généralement compris entre 1 et 10, de préférence entre 1 et 5.REMPIACEMEMT SHEET (RULE 26) molar of the chlorofluorinated compound Rp-CH2CI in alkaline iodide can vary within wide limits. It is generally between 1 and 10, preferably between 1 and 5.
Comme exemples de composés chlorofluorés Rp-CH2CI de départ, on peut mentionner plus particulièrement le 2-chloro-1 ,1 ,1-trifluoroéthane, le 3-chloro- 1 ,1 ,1 ,2,2-pentafluoropropane, le 3-chloro-1 ,1 ,1 ,2-tétrafluoro-2-trifluorométhyl- propane.As examples of starting chlorofluorinated compounds Rp-CH2Cl, there may be mentioned more particularly 2-chloro-1, 1, 1-trifluoroethane, 3-chloro-1, 1, 1, 2,2-pentafluoropropane, 3-chloro -1, 1, 1, 2-tetrafluoro-2-trifluoromethylpropane.
La température réactionnelle peut varier dans de larges limites. Elle est gé¬ néralement comprise entre la température ambiante et le point d'ébuliition du solvant mis en oeuvre, de préférence entre 50 et 250X. La température est à choisir en fonction de la réactivité du composé chlorofluoré de départ ; ainsi, dans le cas du 2- chloro-1 ,1 ,1-trifluoroéthane, on opère avantageusement entre 100 et 230°C, de préférence entre 180 et 220°C. On préfère travailler à la pression atmosphérique, mais on ne sortirait pas du cadre de la présente invention en opérant à pression inférieure ou supérieure. Bien que le procédé selon l'invention puisse être réalisé en discontinuThe reaction temperature can vary within wide limits. It is generally between room temperature and the boiling point of the solvent used, preferably between 50 and 250X. The temperature is to be chosen according to the reactivity of the starting chlorofluorinated compound; thus, in the case of 2-chloro-1, 1, 1-trifluoroethane, the operation is advantageously between 100 and 230 ° C, preferably between 180 and 220 ° C. It is preferred to work at atmospheric pressure, but it would not depart from the scope of the present invention by operating at lower or higher pressure. Although the process according to the invention can be carried out batchwise
(batch), il est particulièrement commode d'opérer de façon semi-continue ou conti¬ nue en éliminant le composé iodo-fluoré du milieu réactionnel au fur et à mesure de sa formation. Le chlorure alcalin sous-produit étant très peu soluble dans le solvant aprotique polaire, précipite dans le milieu réactionnel. Pour la mise en oeuvre du procédé selon l'invention en mode semi-continu, on charge préalablement le réacteur avec l'iodure alcalin et le solvant aprotique polaire, puis après avoir porté le milieu réactionnel sous agitation et à la température choisie, on y introduit en continu le composé chlorofluoré et on soutire en continu un évent gazeux constitué d'un mélange du composé iodo-fluoré désiré et du composé chlorofluoré non réagi. Ce dernier peut être séparé du composé iodo-fluoré par simple distillation et recyclé au réacteur.(batch), it is particularly convenient to operate semi-continuously or continuously by eliminating the iodo-fluorinated compound from the reaction medium as it is formed. The alkaline chloride by-product being very slightly soluble in the polar aprotic solvent, precipitates in the reaction medium. For the implementation of the process according to the invention in semi-continuous mode, the reactor is first charged with alkaline iodide and the polar aprotic solvent, then after having brought the reaction medium under stirring and to the chosen temperature, continuously introducing the chlorofluorinated compound and continuously withdrawing a gaseous vent consisting of a mixture of the desired iodo-fluorinated compound and the unreacted chlorofluorinated compound. The latter can be separated from the iodo-fluorinated compound by simple distillation and recycled to the reactor.
Pour la mise en oeuvre du procédé selon l'invention en mode continu, on opère de la même manière que précédemment pour le procédé semi-continu, mais on soutire en plus en continu la phase liquide que l'on filtre pour éliminer le chlorure alcalin formé ; le filtrat est recyclé au réacteur après ajout d'un appoint d'iodure alcalin.For the implementation of the process according to the invention in continuous mode, the operation is carried out in the same manner as previously for the semi-continuous process, but the liquid phase is further drawn off which is filtered to remove the alkali chloride. trained; the filtrate is recycled to the reactor after adding an alkaline iodide supplement.
Les exemples suivants illustrent l'invention sans la limiter.The following examples illustrate the invention without limiting it.
EXEMPLE 1 Dans un réacteur en verre d'une capacité de 500 ml, équipé d'un dispositif d'agitation (type turbine), d'un dispositif de chauffage et d'un système de régulation de la température, on introduit 200 g de 1 ,3-diméthyl-2-imidazolidinone (DMI) et 45 g (0,3 mole) d'iodure de sodium. Le milieu réactionnel est porté à 210°C sous agita- tion, puis on introduit en continu du 2-chloro-1 ,1 ,1-trifluoroéthane sous forme gazeuse à pression atmosphérique, au moyen d'une canne d'introduction en pied de réacteur. Le débit moyen est d'environ 40 g/h.EXAMPLE 1 In a glass reactor with a capacity of 500 ml, equipped with a stirring device (turbine type), a heating device and a temperature regulation system, 200 g of 1, 3-dimethyl-2-imidazolidinone (DMI) and 45 g (0.3 mole) of sodium iodide. The reaction medium is brought to 210 ° C. with stirring. tion, then continuously introduced 2-chloro-1, 1, 1-trifluoroethane in gaseous form at atmospheric pressure, by means of an introduction rod at the bottom of the reactor. The average flow rate is around 40 g / h.
Le 2-iodo-1 ,1 ,1-trifluoroéthane est récupéré au fur et à mesure de sa forma- tion par condensation des "évents" gazeux. Après 3 heures de réaction, on obtient une conversion de 89 % de l'iodure de sodium et un rendement en 2-iodo-1 ,1 ,1- trifluoroéthane de 86 % par rapport au Nal engagé.The 2-iodo-1, 1, 1-trifluoroethane is recovered as it is formed by condensation of the gaseous "vents". After 3 hours of reaction, a conversion of 89% of the sodium iodide is obtained and a yield of 2-iodo-1,1,1-trifluoroethane of 86% relative to the Nal used.
EXEMPLE 2 On a répété l'exemple 1 , mais en remplaçant le DMI par la même quantité de sulfolane et en portant à 5 heures la durée d'introduction du 2-chloro-1 , 1 ,1 ,-trifluo- roéthane au débit moyen de 40 g/h.EXAMPLE 2 Example 1 was repeated, but replacing the DMI with the same amount of sulfolane and increasing the time for the introduction of 2-chloro-1, 1, 1, -trifluoroethane to 5 hours to 5 hours. 40 g / h.
En fin de réaction, on a obtenu une conversion de 89 % de l'iodure de sodium et un rendement en 2-iodo- 1 ,1 ,1 -trif luoroéthane de 85 % par rapport au Nal engagé.At the end of the reaction, a conversion of 89% of the sodium iodide was obtained and a yield of 2-iodo 1, 1, 1 -trif luoroethane of 85% relative to the Nal used.
EXEMPLE 3 (ComparatiflEXAMPLE 3 (Comparativel
On a répété l'exemple 1 , mais en remplaçant l'iodure de sodium par 35,7 g (0,3 mole) de bromure de potassium. Après 3 heures de réaction, la conversion du bromure de potassium était deExample 1 was repeated, but replacing the sodium iodide with 35.7 g (0.3 mole) of potassium bromide. After 3 hours of reaction, the conversion of potassium bromide was
33 % et le rendement en 2-bromo-1 ,1 ,1-trifluoroéthane de 22 % par rapport au KBr engagé.33% and the yield of 2-bromo-1, 1, 1-trifluoroethane of 22% relative to the KBr used.
EXEMPLE 4 On a répété l'exemple 1 , mais en remplaçant l'iodure de sodium par 50 gEXAMPLE 4 Example 1 was repeated, but replacing the sodium iodide with 50 g
(0,3 mole) d'iodure de potassium.(0.3 mole) potassium iodide.
Après 3 heures et demie d'introduction du 2-chloro-1 ,1 , 1-trifluoroéthane (débit moyen : 41 g/h), on a obtenu une conversion de 95 % de l'iodure de potas¬ sium et un rendement de 90 % en 2-iodo-1 ,1 ,1-trifluoroéthane par rapport à l'iodure de potassium engagé. After 3.5 hours of introduction of 2-chloro-1, 1, 1-trifluoroethane (average flow rate: 41 g / h), 95% conversion of the potassium iodide was obtained and a yield of 90% in 2-iodo-1, 1, 1-trifluoroethane compared to the potassium iodide used.

Claims

REVENDICATIONS
1. Procédé de préparation d'un composé organique iodo-fluoré de formule générale RF-CH2I dans laquelle Rp désigne un radical perfluoroalkyle, linéaire ou ramifié, contenant de 1 à 8 atomes de carbone, caractérisé en ce que l'on fait réagir le composé chloro-fluoré correspondant avec un iodure alcalin au sein d'un solvant aprotique ayant un point d'ébuliition supérieur à celui du composé iodofluoré désiré.1. Process for the preparation of an iodo-fluorinated organic compound of general formula RF-CH2I in which Rp denotes a perfluoroalkyl radical, linear or branched, containing from 1 to 8 carbon atoms, characterized in that the chloro-fluorinated compound corresponding with an alkaline iodide in an aprotic solvent having a boiling point higher than that of the desired iodofluorinated compound.
2. Procédé selon la revendication 1 dans lequel le solvant aprotique polaire est choisi dans le groupe constitué par le sulfolane, le N,N-diméthylformamide, le diméthylsulfoxyde, le N,N-diméthylacétamide, la N-méthylpyrrolidone, la 1,3- diméthyl-2-imidazolidinone, la 1 ,3-diméthyl-3,4,5,6-tétrahydro-2-pyrimidinone et leurs mélanges.2. Method according to claim 1 wherein the polar aprotic solvent is chosen from the group consisting of sulfolane, N, N-dimethylformamide, dimethylsulfoxide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3- dimethyl-2-imidazolidinone, 1, 3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone and their mixtures.
3. Procédé selon la revendication 1 dans lequel le solvant aprotique polaire est le sulfolane ou la 1 ,3-diméthyl-2-imidazolidinone.3. The method of claim 1 wherein the polar aprotic solvent is sulfolane or 1,3-dimethyl-2-imidazolidinone.
4. Procédé selon l'une des revendications 1 à 3 dans lequel on opère à une température allant de la température ambiante jusqu'au point d'ébuliition du solvant, de préférence à une température comprise entre 50 et 250°C.4. Method according to one of claims 1 to 3 wherein one operates at a temperature ranging from room temperature to the boiling point of the solvent, preferably at a temperature between 50 and 250 ° C.
5. Procédé selon l'une des revendications 1 à 4 dans lequel on opère à pression atmosphérique.5. Method according to one of claims 1 to 4 wherein one operates at atmospheric pressure.
6. Procédé selon l'une des revendications 1 à 5 dans lequel on utilise l'iodure de sodium ou l'iodure de potassium.6. Method according to one of claims 1 to 5 wherein sodium iodide or potassium iodide is used.
7. Procédé selon l'une des revendications 1 à 6 dans lequel on emploie 1 à 75 parties en poids d'iodure alcalin (de préférence 5 à 50) pour 100 parties en poids de solvant.7. Method according to one of claims 1 to 6 wherein one uses 1 to 75 parts by weight of alkali iodide (preferably 5 to 50) per 100 parts by weight of solvent.
8. Procédé selon l'une des revendications 1 à 7 dans lequel le rapport molaire du composé chlorofluoré au iodure alcalin est compris entre 1 et 10, de préférence entre 1 et 5.8. Method according to one of claims 1 to 7 wherein the molar ratio of chlorofluorinated compound to alkali iodide is between 1 and 10, preferably between 1 and 5.
9. Procédé selon l'une des revendications 1 à 8 dans lequel prépare le 2- iodo-1 ,1 ,1-trifluoroéthane à partir du 2-chloro-1 ,1 ,1-trifluoroéthane.9. Method according to one of claims 1 to 8 wherein prepares 2-iodo-1, 1, 1-trifluoroethane from 2-chloro-1, 1, 1-trifluoroethane.
10. Procédé selon la revendication 9 dans lequel on opère entre 100 et 230°C, de préférence entre 180 et 220X. 10. The method of claim 9 wherein one operates between 100 and 230 ° C, preferably between 180 and 220X.
PCT/FR1997/000153 1996-02-26 1997-01-27 Synthesis of organic iodine-fluorine compounds WO1997030959A1 (en)

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PATENT ABSTRACTS OF JAPAN vol. 013, no. 553 (C - 663) 8 December 1989 (1989-12-08) *

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