DE976732C - Process for the production of chlorine- and fluorine-containing dimethyl sulfides - Google Patents
Process for the production of chlorine- and fluorine-containing dimethyl sulfidesInfo
- Publication number
- DE976732C DE976732C DESCH11832A DESC011832A DE976732C DE 976732 C DE976732 C DE 976732C DE SCH11832 A DESCH11832 A DE SCH11832A DE SC011832 A DESC011832 A DE SC011832A DE 976732 C DE976732 C DE 976732C
- Authority
- DE
- Germany
- Prior art keywords
- fluorine
- weight
- parts
- sulfide
- chlorine
- 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.)
- Expired
Links
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 title claims description 19
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 15
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 7
- 238000003682 fluorination reaction Methods 0.000 description 6
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 5
- 239000012025 fluorinating agent Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- -1 polyethylene Polymers 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HWHKIGQTQXAUNO-UHFFFAOYSA-N tetrachloro(dimethyl)-$l^{6}-sulfane Chemical compound CS(C)(Cl)(Cl)(Cl)Cl HWHKIGQTQXAUNO-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021582 Cobalt(II) fluoride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- FMSYTQMJOCCCQS-UHFFFAOYSA-L difluoromercury Chemical compound F[Hg]F FMSYTQMJOCCCQS-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- FQZUXVBMUHSNRN-UHFFFAOYSA-L mercury(1+);difluoride Chemical compound [Hg]F.[Hg]F FQZUXVBMUHSNRN-UHFFFAOYSA-L 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von chlor- und fluorhaltigen Dimethylsulfiden Es ist bekannt, daß in organischen Chlorverbindungen mit Fluorierungsmitteln, wie H2F2, HgF2, Hg2F2, CoF2, SbF3 und SbF3+SbCl5, oft ein Austausch von Chloratomen durch Fluoratome herbeigeführt werden kann. Nach dem heutigen Stand der Technik können aber keine generellen Regeln bzw.Process for the production of chlorine- and fluorine-containing dimethyl sulfides It it is known that in organic chlorine compounds with fluorinating agents such as H2F2, HgF2, Hg2F2, CoF2, SbF3 and SbF3 + SbCl5, often an exchange of chlorine atoms by Fluorine atoms can be brought about. According to the current state of the art, you can but no general rules or
Arbeitsvorschriften gegeben werden, vielmehr muß von Fall zu Fall experimentell geprüft werden, ob Chloratome einer organischen Verbindung durch Behandeln mit einem der bekannten Fluorierungsmittel durch Fluoratome austauschbar sind (siehe H. J. Emeleus, Journal of the Chemical Society, 1942, S. 44I bis 447; J. H. Simons, Fluoride Chemistry, Vol. II, S. 2I9, New York, 1954).Work regulations are given, rather must be given on a case-by-case basis experimentally tested whether chlorine atoms of an organic compound by treating are exchangeable by fluorine atoms with one of the known fluorinating agents (see H. J. Emeleus, Journal of the Chemical Society, 1942, pp. 44I to 447; J. H. Simons, Fluoride Chemistry, Vol. II, pp. 219, New York, 1954).
Chlor- und fluorhaltige Dimethylsulfide sind in der Literatur beschrieben worden: Nach H. Böhme, H. Fischer und R. Frank (vgl. Liebigs Annalen der Chemie, Bd. 563, [I949], S. 6I) soll Monochlor-dimethylsulfid bei Behandlung mit wasserfreiem Fluorwasserstoff in Kupfer-oder Platingefäßen in Monofluor-dimethylsulfid übergehen. Nach Beobachtungen der Erfinder ist das nicht der Fall. Sie haben selbst bei verschärften Versuchsbedingungen die Umsetzung nicht erzwingen können. Für die Gewinnung des Monofluordimethylsulfids geben die Autoren keine Arbeitsvorschrift; auch fehlen physikalische Kenndaten der Verbindung. Chlorine- and fluorine-containing dimethyl sulfides are described in the literature been: After H. Böhme, H. Fischer and R. Frank (cf. Liebigs Annalen der Chemie, Vol. 563, [1949], p. 6I) is said to be monochloro-dimethyl sulfide when treated with anhydrous In copper or platinum vessels, hydrogen fluoride is converted into monofluorodimethyl sulfide. According to observations the inventor is that is not the case. They have cannot force implementation even under more stringent test conditions. The authors do not give any work instructions for obtaining the monofluorodimethyl sulfide; physical characteristics of the connection are also missing.
Zu einer beabsichtigten Darstellung werden folgende Versuche durchgefihrt: a) Umsatz des Monochlor-dimethylsulfids mit wasserfreiem Fluorwasserstoff in Kupfergefäßen unter verschiedenen Versuchsbedingungen. b) Umsatz von Monochlordimethylsulfidmit SbF3. c) Umsatz von Monochlor-dimethylsulfid mit SbF8+ SbCl5. d) Umsatz von Monochlor-dimethylsulfid mit ShF3tBr2. The following experiments are carried out for an intended representation: a) Conversion of the monochloro-dimethyl sulfide with anhydrous hydrogen fluoride in copper vessels under different test conditions. b) conversion of monochlorodimethyl sulfide with SbF3. c) Conversion of monochloro-dimethyl sulfide with SbF8 + SbCl5. d) Conversion of monochloro-dimethyl sulfide with ShF3tBr2.
Keiner der Versuche ergab Monofluor-dimethylsulfid. Die Verbindung Monofluor-dimethylsulfid und die Austauschreaktion von Chlor durch Fluor bei chlorierten Dimethylsulfiden mittels Fluorwasserstoff haben damit als nicht bekannt zu gelten. None of the experiments resulted in monofluorodimethyl sulfide. The connection Monofluorodimethyl sulfide and the exchange reaction of chlorine with fluorine in chlorinated ones Dimethyl sulfides using hydrogen fluoride are therefore not to be considered known.
W. E. Truce und Mitarbeiter (vgl. Journal of the American Chemical Society Bd. 74, [I952], 5. 3594) haben mit SbFS beim a,a,a-Trichlordimethylsulfid und mit SbF3+SbCl5 beim a,a,a-Trichlor-dimethylsulfid, beim -asymmetrischen Tetrachlor-dimethylsulfid und beim Pentachlor-dimethylsulfid Chloratome durch Fluoratome ersetzen können. SbF3 ist aber kein allgemein anwendbares Fluorierungsmittel für chlorierte Dimethylsulfide, denn beim Hexachlor-dimethylsulfid ist die Fluorierung des Thioäthers nicht möglich. Nach W. E. Truce und Mitarbeitern (a. a. O) und eigenen Erfahrungen werden aus dem durchchlorierten Dimethylsulfid und SbF3 nur schwefelfreie halogenhaltige Bruchstücke erhalten. W. E. Truce et al. (See Journal of the American Chemical Society Vol. 74, [I952], 5. 3594) have worked with SbFS for a, a, a-Trichlorodimethylsulfid and with SbF3 + SbCl5 for a, a, a-trichloro-dimethylsulphide, for -asymmetrical tetrachloro-dimethylsulphide and in the case of pentachlorodimethyl sulfide, chlorine atoms can be replaced by fluorine atoms. However, SbF3 is not a generally applicable fluorinating agent for chlorinated dimethyl sulfides, because the fluorination of the thioether is not possible with hexachlorodimethyl sulfide. According to W. E. Truce and colleagues (op. Cit. O) and our own experience, the through chlorinated dimethyl sulfide and SbF3 only sulfur-free halogen-containing fragments obtain.
Es wurde nun gefunden, daß chlor- oder chlor-und fluorhaltige Dimethylsulfide mit mindestens 4 Halogenatomen im Molekül ihre Chloratome mittels Fluorwasserstoff austauschen. Dazu genügt schon Stehenlassen der chlorierten Thioäther mit technischem Fluorwasserstoff. Der Austausch der Chloratome durch Fluoratome tritt stufenweise ein; bei längeren Reaktionszeiten, höherer Reaktionstemperatur und Anwendung eines größeren tSberschusses an Fluorwasserstoff wird der Anteil an höherfluorierten Verbindungen größer. It has now been found that chlorine- or chlorine- and fluorine-containing dimethyl sulfides with at least 4 halogen atoms in the molecule their chlorine atoms by means of hydrogen fluoride change. All that is required is letting the chlorinated thioethers stand with technical grade Hydrogen fluoride. The exchange of chlorine atoms by fluorine atoms occurs gradually a; with longer reaction times, higher reaction temperature and use of a A larger excess of hydrogen fluoride increases the proportion of more highly fluorinated compounds greater.
Auch wenn Antimontrifluorid mit oder ohne Katalysatoren als Fluorierungsmittel brauchbar ist, 4ìat die Umsetzung mit Fluorwasserstoff auf alle Fälle Vorteile: nicht umgesetztes Fluorierungs- -mittel ist leicht zurückzugewinnen, es treten keine Nebenreaktionen unter Zerstörung des Thioäthers ein, und es bilden sich bei der Umsetzung keine festen Phasen. Even if antimony trifluoride with or without catalysts as a fluorinating agent is useful, the reaction with hydrogen fluoride is in any case Advantages: unconverted fluorinating agent can easily be recovered; none occur Side reactions with the destruction of the thioether, and it is formed in the Implementation no fixed phases.
Die gewinnbaren Verbindungen können als Insekticide, als Lösungs-Extraktions- und Fällungsmittel. als Kälteträger und als Zwischenprodukte Verwendung finden. The recoverable compounds can be used as insecticides, as solution extraction and precipitants. as a refrigerant and as an intermediate use.
Beispiel I Fluorierung von asymmetrischem Tetrachlor-dimethylsulfid a) Trichlor-monofluor-dimethylsulfid als Hauptprodukt In einer Kupferapparatur mit Rückflußkühler, Rührer und einer Vorrichtung zum Abführen des entwickelten Chlorwasserstoffes werden unter Kühlung I92 Gewichtsteile Fluorwasserstoff und 4.00 Gewichtsteile asymmetrisclles Tetrachlordimethylsulfid 10 Stunden kräftig gerührt. Man gießt das Reaktionsgemisch auf Eis und nimmt das Fluorierungsprodukt in Tetrachlorkohlenstoff auf. Example I Fluorination of Asymmetric Tetrachlorodimethylsulfide a) Trichloromonofluorodimethyl sulfide as the main product In a copper apparatus with Reflux condenser, stirrer and a device for removing the evolved hydrogen chloride 192 parts by weight of hydrogen fluoride and 4.00 parts by weight of asymmetric acid become with cooling Tetrachlorodimethyl sulfide was stirred vigorously for 10 hours. The reaction mixture is poured on ice and absorbs the fluorination product in carbon tetrachloride.
Nach dem Trocknen werden bei der Destillation 275 Gewichtsteile a-Fluor-a,a,a'-trichlor-dimethylsulfid erhalten (750/0 der Theorie; Kp.12=420 C, Kp.760= 1490 C); daneben entstehen 23,5 Gewichtsteile a,a-Difluor-a,a'-dichlor-dimethylsulfid (7 0/o der Theorie; Kp.760=o60 C). 64 Gewichtsteile Ausgangsmaterial (60/oder Theorie; Kp12=7i0 C) werden zurückgewonnen und können wieder verwendet werden. b) a,a-Difluor-a,a'-dichlor-dimethylsulfid als Hauptprodukt In der im Beispiel a) beschriebenen. Apparatur werden 400 Gewichtsteile asymmetrisches Tetrachlor-dimethylsulfid und 440 Gewichtsteile technischer Fluorwasserstoff 30 Stunden bei Zimmertemperatur gerührt. Die Aufarbeitung des Reaktionsproduktes geschieht in gleicher Weise, wie unter a) beschrieben worden ist. Es werden 2I7 Gewichtsteile a,a-Difluor-a,a'-dichlor-dimethylsulfid (65 0/o der Theorie; Kp.760 = 1060 C) und 5I Gewichtsteile a-Fluor-a,a,a'-trichlor-dimethylsulfid (I40/o der Theorie; Kp.12 =420 C) erhalten. c) a,a-Difluor-a,a'-dichlor-dimethylsulfid und a,a,a-Trifluor-a'-chlor-dimethylsulfid als Hauptprodukte 200 Gewichtsteile asymmetrisches Tetrachlordimethylsulfid bleiben mit I49 Gewichtsteilen technischem Fluorwasserstoff in einer Polyäthylenflasche 4 Tage lang bei Zimmertemperatur stehen.After drying, 275 parts by weight of a-fluoro-a, a, a'-trichloro-dimethyl sulfide are obtained in the distillation obtained (750/0 of theory; bp 12 = 420 C, bp 760 = 1490 C); next to it there are 23.5 Parts by weight of a, a-difluoro-a, a'-dichloro-dimethylsulfide (70 / o of theory; bp 760 = o60 C). 64 parts by weight of starting material (60 / or theory; Kp12 = 7i0 C) are recovered and can be used again. b) a, a-Difluoro-a, a'-dichloro-dimethyl sulfide as Main product in the one described in example a). Apparatus are 400 parts by weight asymmetric tetrachlorodimethyl sulfide and 440 parts by weight of technical hydrogen fluoride Stirred for 30 hours at room temperature. Working up the reaction product happens in the same way as has been described under a). There will be 2I7 Parts by weight of a, a-difluoro-a, a'-dichloro-dimethyl sulfide (65% of theory; boiling point 760 = 1060 C) and 51 parts by weight of a-fluoro-a, a, a'-trichloro-dimethyl sulfide (I40 / o der Theory; Kp.12 = 420 C). c) a, a-Difluoro-a, a'-dichloro-dimethyl sulfide and a, a, a-Trifluoro-a'-chloro-dimethyl sulfide as main products 200 parts by weight of asymmetric Tetrachlorodimethyl sulfide remains with 149 parts by weight of technical-grade hydrogen fluoride stand in a polyethylene bottle at room temperature for 4 days.
Die Polyäthylenflasche trägt ein ausgezogenes Polyäthylenrohr, damit kein tberdruck entstehen kann.The polyethylene bottle carries an extended polyethylene tube so that no overpressure can arise.
Man schüttelt das Reaktionsgefäß tagsüber stündlich um, wobei kräftig Chlorwasserstoff entweicht.The reaction vessel is shaken every hour during the day, vigorously Hydrogen chloride escapes.
Nach der unter a) beschriebenen Aufarbeitung werden 112 Gewichtsteile a,a-Difluor-a,a'-dichlor-dimethylsulfid (670/0 der Theorie; Kp.760 = 1060 C), 23 Gewichtsteile a,a, a-Trifluor-a'-chlor-dimethylsulfid (15 0/o der Theorie; Kp.700=60 C) und I3 Gewichtsteile a-Fluor-a, a,a'-trichlor-dimethylsulfid (70/0 der Theorie; Kp.12=42° C) erhalten.After the work-up described under a), 112 parts by weight are obtained a, a-Difluoro-a, a'-dichloro-dimethyl sulfide (670/0 of theory; bp 760 = 1060 C), 23 Parts by weight of a, a, a-trifluoro-a'-chloro-dimethyl sulfide (15% of theory; b.p. 700 = 60 C) and 13 parts by weight of a-fluoro-a, a, a'-trichloro-dimethyl sulfide (70/0 of theory; Bp 12 = 42 ° C).
Beispiel 2 Fluorierung von a-Fluor-a,a, a'-trichlor-dimethylsulfld In einer Polyäthylenflasche werden I85 Gewichtsteile a-Fluor-a,a,a'-trichlor-dimethylsulfid mit I49 Gewichtsteilen technischem Fluorwasserstoff wie unter Beispiel I, c) 2 Tage lang umgesetzt. Nach der I a) angegebenen Aufarbeitung werden 50 Gewichtsteile a,a - Difluor - a,a'- dichlor- dimethylsulfid (30% der Theorie; Kp.760=o60 C) und 15 Gewichtsteile a,a,a -Trifluor-a'- chlor- dimethylsulfid (10% der Theorie; Kp.7(o=64° C) erhalten; der Rest ist Ausgangsmaterial (Kp.12=7I0 C) und kann wieder verwendet werden. Example 2 Fluorination of a-fluoro-a, a, a'-trichloro-dimethyl sulfide In a polyethylene bottle, 185 parts by weight of a-fluorine-a, a, a'-trichloro-dimethyl sulfide with I49 Parts by weight of technical-grade hydrogen fluoride as in the example I, c) implemented for 2 days. After the work-up indicated I a) 50 parts by weight a, a - difluoro - a, a'-dichloro dimethyl sulfide (30% of theory; bp 760 = o60 C) and 15 parts by weight of a, a, a -trifluoro-a'-chloro-dimethyl sulfide (10% of theory; b.p. 7 (o = 64 ° C) obtained; the rest is the starting material (Kp.12 = 7I0 C) and can be reused will.
Beispiel 3 Fluorierung von Pentachlor-dimethylsulfid 325 Gewichtsteile Pentachlor-dimethylsulfid werden mit 790 Gewichtsteilen technischem Fluorwasserstoff 8 Tage lang wie unter 1 c) umgesetzt. Example 3 Fluorination of pentachloro dimethyl sulfide 325 parts by weight Pentachloro-dimethyl sulfide with 790 parts by weight of technical hydrogen fluoride Implemented for 8 days as under 1 c).
Bei der Destillation des Reaktionsproduktes werden 125 Gewichtsteile a-Fluor-a,a,a',a'-tetrachlor-dimethylsulfid (4I °/o der Theorie; Kp.15=52° C) und 46 Gewichtsteile a,a'- Difluor- a,a,a'-trichlor-dimethylsulfid (I70/o der Theorie; Kp.50=44°C) erhalten; der Rest ist Ausgangsmaterial (Kp.o= 740 C) und kann wieder verwendet werden.During the distillation of the reaction product, 125 parts by weight a-fluoro-a, a, a ', a'-tetrachloro-dimethylsulfide (41% of theory; bp 15 = 52 ° C) and 46 parts by weight of a, a'-difluoro-a, a, a'-trichloro-dimethyl sulfide (170 / o of theory; Bp 50 = 44 ° C) obtained; the rest is the starting material (bp = 740 C) and can be used again be used.
Beispiel 4 Fluorierung von Hexachlor-dimethylsulfid 270 Gewichtsteile Hexachlor-dimethylsulfid und 295 Gewichtsteile technischer Fluorwasserstoff werden 30 Tage lang wie unter 1 c) umgesetzt; nach jeweils 8 Tagen füllt man den verbrauchten Fluorwasserstoff nach. Nach der üblichen Aufarbeitung werden 72 Gewichtsteile Monofinor-pentachlordimethylsulfid (296/o der Theorie; Kp.12=66° C) und 6 Gewichtsteile symmetrisches Difluortetrachlor-dimethylsulfid (270/0 der Theorie; Kp.12= 540 C) erhalten. 103 Gewichtsteile Ausgangsmaterial (Kpe1O=go° C) werden zurückgewonnen und können wieder verwendet werden. Example 4 Fluorination of hexachlorodimethyl sulfide 270 parts by weight Hexachlorodimethyl sulfide and 295 parts by weight of technical hydrogen fluoride Implemented for 30 days as under 1 c); after every 8 days the used one is filled Hydrogen fluoride. After the usual work-up, 72 parts by weight of monofinor pentachlorodimethyl sulfide are added (296 / o of theory; bp 12 = 66 ° C) and 6 parts by weight of symmetrical difluorotetrachlorodimethyl sulfide (270/0 of theory; Kp.12 = 540 C). 103 parts by weight of starting material (Kpe1O = go ° C) are recovered and can be used again.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH11832A DE976732C (en) | 1953-02-25 | 1953-02-25 | Process for the production of chlorine- and fluorine-containing dimethyl sulfides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH11832A DE976732C (en) | 1953-02-25 | 1953-02-25 | Process for the production of chlorine- and fluorine-containing dimethyl sulfides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE976732C true DE976732C (en) | 1964-04-02 |
Family
ID=7426614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH11832A Expired DE976732C (en) | 1953-02-25 | 1953-02-25 | Process for the production of chlorine- and fluorine-containing dimethyl sulfides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE976732C (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE552919C (en) * | 1930-09-20 | 1932-06-21 | Kinetic Chemicals Inc | Process for the preparation of fluorine compounds of aliphatic hydrocarbons |
| DE575593C (en) * | 1931-11-10 | 1933-05-22 | I G Farbenindustrie Akt Ges | Process for the production of aromatic hydrocarbons fluorinated in the side chain |
| US2005710A (en) * | 1931-05-20 | 1935-06-18 | Kinetic Chemicals Inc | Preparation of fluorine compounds |
| FR798421A (en) * | 1934-11-29 | 1936-05-16 | Ig Farbenindustrie Ag | Process for the preparation of fluorinated compounds of aliphatic hydrocarbons |
| FR820796A (en) * | 1936-04-18 | 1937-11-18 | Ig Farbenindustrie Ag | Tri-fluoromethyl-phenyl sulphides, oxidation products of these sulphides and process for the preparation of these compounds |
-
1953
- 1953-02-25 DE DESCH11832A patent/DE976732C/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE552919C (en) * | 1930-09-20 | 1932-06-21 | Kinetic Chemicals Inc | Process for the preparation of fluorine compounds of aliphatic hydrocarbons |
| US2005710A (en) * | 1931-05-20 | 1935-06-18 | Kinetic Chemicals Inc | Preparation of fluorine compounds |
| DE575593C (en) * | 1931-11-10 | 1933-05-22 | I G Farbenindustrie Akt Ges | Process for the production of aromatic hydrocarbons fluorinated in the side chain |
| FR798421A (en) * | 1934-11-29 | 1936-05-16 | Ig Farbenindustrie Ag | Process for the preparation of fluorinated compounds of aliphatic hydrocarbons |
| FR820796A (en) * | 1936-04-18 | 1937-11-18 | Ig Farbenindustrie Ag | Tri-fluoromethyl-phenyl sulphides, oxidation products of these sulphides and process for the preparation of these compounds |
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