DE3209416A1 - Process for the preparation of trimethylsilyl trifluoromethanesulphonate - Google Patents
Process for the preparation of trimethylsilyl trifluoromethanesulphonateInfo
- Publication number
- DE3209416A1 DE3209416A1 DE19823209416 DE3209416A DE3209416A1 DE 3209416 A1 DE3209416 A1 DE 3209416A1 DE 19823209416 DE19823209416 DE 19823209416 DE 3209416 A DE3209416 A DE 3209416A DE 3209416 A1 DE3209416 A1 DE 3209416A1
- Authority
- DE
- Germany
- Prior art keywords
- tetramethylsilane
- reaction
- process according
- trifluoromethanesulfonic acid
- hydrocarbons
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims abstract description 16
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001942 cyclopropanes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QDUOESIXNVKNKB-UHFFFAOYSA-N trimethylsilyl hydrogen sulfate Chemical compound C[Si](C)(C)OS(O)(=O)=O QDUOESIXNVKNKB-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
Abstract
Description
Verfahren zur Herstellung von Trimethylsilyl-Process for the preparation of trimethylsilyl
trifluoromethansulfonat Die Erfindung betrifft eine einfache in-situ-Herstellung von Trimethylsilyl-trifluoromethansulfonat. trifluoromethanesulfonate The invention relates to a simple in-situ production of trimethylsilyl trifluoromethanesulfonate.
Trimethylsilyl-trifluoromethansulfonat (2; TMS-Triflat) ist im Handel erhältlich und wird weit verbreitet für verschiedene synthetische Anwendungszwecke verwendet (vgl. R. Noyori, S. Murata und M. Suzuki, Tetrahedron 37, 3899 (1981); H. Emde et al, Synthesis, 1982, 1; M. Demuth et al, Helv.Chim.Acta 63, 2440 (1980); K. Schaffner und M. Demuth, Chimia 35, 437 (1981); M.Trimethylsilyl trifluoromethanesulfonate (2; TMS triflate) is commercially available available and widely used for various synthetic uses used (see R. Noyori, S. Murata and M. Suzuki, Tetrahedron 37, 3899 (1981); H. Emde et al, Synthesis, 1982, 1; M. Demuth et al, Helv. Chim. Acta 63: 2440 (1980); K. Schaffner and M. Demuth, Chimia 35, 437 (1981); M.
Demuth, G. Mikhail und M.V. George, Helv.Chim.Acta 64, 2759 (1981)). Das Reagens hydrolysiert rasch an der Luft. Dieser Nachteil lässt sich vermeiden, wenn man es in seiner polymeren Form, als Nafion-TMS, verwendet; letzteres widersteht in beträchtlichem Maße einer hydrolytischen Spaltung (T. Noyori et al, loc. cit.; M. Demuth et al, loc. cit. (1980, 1981); K.Demuth, G. Mikhail and M.V. George, Helv. Chim. Acta 64, 2759 (1981)). The reagent hydrolyzes rapidly in air. This disadvantage can be avoided when used in its polymeric form, as Nafion-TMS; the latter resists to a considerable extent hydrolytic cleavage (T. Noyori et al, loc. cit .; M. Demuth et al, loc. cit. (1980, 1981); K.
Schaffner und M. Demuth, loc.cit.). Das monomere TMS-Triflat bietet jedoch andere Vorteile gegenüber dem Polymeren (R. Noyori et al., loc.cit.,H. Emde et al, loc.cit.); z.B. bewirkt sein stärker ausgeprägtes elektrophiles Verhalten eine Spaltung von Cyclopropanen bereits bei Umgebungstemperatur (M.Schaffner and M. Demuth, loc. Cit.). The monomeric TMS triflate offers however, other advantages over the polymer (R. Noyori et al., loc.cit., H. Emde et al, loc. Cit.); E.g. its more pronounced causes electrophilicity Behavior a cleavage of cyclopropanes already at ambient temperature (M.
Demuth et al., 1980). Aus diesem Grunde erschien eine billige in-situ-Herstellung, die nur inerte Nebenprodukte liefert, wünschenswert.Demuth et al., 1980). For this reason, cheap in-situ manufacture appeared, which only provides inert by-products, is desirable.
TMS-Triflat -(2) ist bisher im Prinzip auf folgenden drei Wegen zugänglich, von denen jedoch keiner sämtlichen vorgenannten Anforderungen genügt: Behandlung von Chlorotrimethylsilan mit dem teuren Silber-trifluoromethansulfonat in Benzol unter Rückfluß (M. Schmeißer,P. Sartori und B. Lippsmeier, Chem. Ber. 103, 868 (1970) und mit unverdünnter Trifluoromethansulfonsäure (1) während mehrerer Stunden bei 1200C und Abtreiben des entstandenen Hydrogenchlorids (H.C. Marsmann und H.G. Horn, Z.Naturforsch.(b) 27, 1448 (1972)). Weiterhin wurde Trimethylsilyltrifluoromethansulfonat (2) auch in situ durch Reaktion von Trifluoromethansulfonsäure (1) unter milden Bedingungen mit einem der beiden kostspieligen Silane Phenyltrimethylsilan (D. Häbich und F. Effenberger, Synthesis 1978, 755) und Allyltrimethylsilan (T. Morita, Y. Okamoto und H. Sakurai, Synthesis 1981, 745).TMS-Triflat - (2) has so far been accessible in principle in the following three ways, none of which, however, meet all of the above requirements: Treatment of chlorotrimethylsilane with the expensive silver trifluoromethanesulfonate in benzene under reflux (M. Schmeißer, P. Sartori and B. Lippsmeier, Chem. Ber. 103, 868 (1970) and with undiluted trifluoromethanesulfonic acid (1) for several hours 1200C and driving off the hydrogen chloride formed (H.C. Marsmann and H.G. Horn, Z. Naturforsch. (B) 27, 1448 (1972)). Trimethylsilyl trifluoromethanesulfonate was also used (2) also in situ by reacting trifluoromethanesulfonic acid (1) under mild conditions Conditions with one of the two expensive silanes phenyltrimethylsilane (D. Häbich and F. Effenberger, Synthesis 1978, 755) and allyltrimethylsilane (T. Morita, Y. Okamoto and H. Sakurai, Synthesis 1981, 745).
hergestellt.manufactured.
Es ist ferner bekannt, daß Schwefelsäure mit Tetramethylsilan während 1,5stündigem Schütteln bei Raumtemperatur reagiert und Trimethylsilylsulfat liefert (R.E. Reavill, J.Chem. Soc. 1964, 519).It is also known that sulfuric acid reacts with tetramethylsilane during Shaking for 1.5 hours at room temperature reacts and gives trimethylsilyl sulfate (R.E. Reavill, J. Chem. Soc. 1964, 519).
Es wurde ferner überraschenderweise von M. Schmeißer et al, loc.cit. berichtet, daß die Umsetzung von Trifluormethansulfonsäure (1) mit Tetramethylsilan auch bei einer 48 Stunden währenden Behandlung unter Rückflußtemperatur zu keinem Ergebnis führt. Aufgrund dieser Veröffentlichung wurden daher andere Methoden zur Herstellung von Trimethylsilyl-trifluormethansulfonat gefunden und veröffentlicht, die alle wesentlich kostspieliger sind und teilweise unangenehme Nebenprodukte liefern, wobei die Veröffentlichungen oben genannt wurden.It was also surprisingly by M. Schmeißer et al, loc. Cit. reported that the reaction of trifluoromethanesulfonic acid (1) with tetramethylsilane even after treatment for 48 hours under reflux temperature, none Result leads. As a result of this publication, other methods for Production of trimethylsilyl trifluoromethanesulfonate found and published, all of which are much more expensive and sometimes unpleasant by-products deliver, the publications mentioned above.
Die Erfindung stellt sich die Aufgabe, ein leicht durchführbares Verfahren zur Herstellung von Trimethylsilyl-trifluormethansulfonat zu schaffen.The object of the invention is to provide a method that can be carried out easily to create trimethylsilyl trifluoromethanesulfonate.
Überraschenderweise wurde gefunden, daß man sehr einfach zum gewünschten Produkt Trimethylsilyl-trifluormethansulfonat (2) gelangen kann, wenn man Trifluormethansulfonsäure (1) bei Umgebungstemperatur und Normaldruck mit Tetramethylsilan umsetzt.Surprisingly, it has been found that it is very easy to get to the desired Trimethylsilyl trifluoromethanesulfonate (2) product can be obtained when using trifluoromethanesulfonic acid (1) Reacts with tetramethylsilane at ambient temperature and normal pressure.
Das erfindungsgemässe Verfahren wird durch die folgende Gleichung erläutert. The method according to the invention is illustrated by the following equation.
Die Erfindung betrifft dementsprechend ein Verfahren zur Herstellung von Trimethylsilyl-trifluormethansulfonat, das dadurch gekennzeichnet ist, daß man Trifluormethansulfonsäure mit Tetramethylsilan umsetzt.The invention accordingly relates to a method of production of trimethylsilyl trifluoromethanesulfonate, which is characterized in that Reacts trifluoromethanesulfonic acid with tetramethylsilane.
Das Verfahren kann bei Temperaturen von -80 bis +100"C, vorzugsweise bei Temperaturen von 0 bis 800C und insbesondere bei Raum- oder Umgebungstemperatur, d.h. in einem Bereich von 10 bis 300C durchgeführt werden. Die Trifluromethansulfonsäure und das Tetramethylsilan können in beliebigem Molverhältnis eingesetzt werden, jedoch wird ein Molverhältnis von 1 : 1, oder aber ein kleiner Überschuss des Tetramethylsilan bevorzugt, d.h. ein Molverhältnis von Trifluormethansulfonsäure zu Tetramethylsilan von 1 : 1,1 bis 1,5, vorzugsweise von 1 : 1,2. Man kann ohne weiteres auch einen höheren Überschuss an Tetramethylsilan verwenden, wenn das Tetramethylsilan gleichzeitig als Lösungsmittel dienen soll.The process can be carried out at temperatures from -80 to +100 "C, preferably at temperatures from 0 to 800C and especially at room or ambient temperature, i.e. in a range of 10 to 300C. The trifluromethanesulfonic acid and the tetramethylsilane can be used in any molar ratio, however a molar ratio of 1: 1, or a small excess of the tetramethylsilane preferred, i.e. a molar ratio of trifluoromethanesulfonic acid to tetramethylsilane from 1: 1.1 to 1.5, preferably from 1: 1.2. You can do without additional also use a higher excess of tetramethylsilane if the tetramethylsilane to serve as a solvent at the same time.
Die Reaktion kann in inerten Lösungsmitteln durchgeführt werden.The reaction can be carried out in inert solvents.
Geeignete Lösungsmittel sind beispielsweise Kohlenwasserstoffe wie Pentan, Hexan, Dodecan oder aromatische Kohlenwasserstoffe wie Benzol, Toluol, Xylole oder chlorierte Kohlenwasserstoffe wie Dichlormethan, Trichlormethan, Tetrachlormethan, Chlorbenzol oder Äther wie Tetrahydrofuran, Diethylether, Furan.Suitable solvents are, for example, hydrocarbons such as Pentane, hexane, dodecane or aromatic hydrocarbons such as benzene, toluene, xylenes or chlorinated hydrocarbons such as dichloromethane, trichloromethane, carbon tetrachloride, Chlorobenzene or ethers such as tetrahydrofuran, diethyl ether, furan.
Die erfindungsgemässe Umsetzung wird üblicherweise bei Normaldruck durchgeführt.The reaction according to the invention is usually carried out at normal pressure carried out.
Im allgemeinen wird die Umsetzung unter Feuchtigkeitsausschluß, vorzugsweise unter einem inerten Schutzgas wie z.B. Argon durchgeführt.In general, the reaction with the exclusion of moisture is preferred carried out under an inert protective gas such as argon.
Für die Umsetzung spielt es keine Rolle, ob-man von sauber redestilliertem Tetramethylsilan oder von Tetramethylsilan ausgeht, das als Handelsprodukt z.B. von Merck Darmstadt erhältlich ist. Das gleiche glt für die Trifluormethansulfonsäure.For the implementation, it does not matter whether you redistilled from clean Starting from tetramethylsilane or from tetramethylsilane, which is available as a commercial product e.g. is available from Merck Darmstadt. The same applies to trifluoromethanesulfonic acid.
Die Erfindung wird anhand des folgenden Ausführungsbeispiels erläutert.The invention is explained using the following exemplary embodiment.
Beispiel 0,1 Mol Trifluormethansulfonsäure wurde mit 0,12 Mol Tetramethylsilan unter Argon bei Raumtemperatur vermischt, wobei eine spontane Methanentwicklung auftrat (die Analyse wurde mittels Gas-Flüssigkeitschromatographie unter Einsatz einer 48 m-Glas-Kapillarsäule OVl bei 0°C und Massenspektroskopie durchgeführt).Example 0.1 mole of trifluoromethanesulfonic acid was mixed with 0.12 mole of tetramethylsilane mixed under argon at room temperature, with a spontaneous evolution of methane occurred (analysis was performed using gas-liquid chromatography carried out a 48 m glass capillary column OVl at 0 ° C and mass spectroscopy).
Aufgrund der Überwachung mittels H-NMR-Spektroskopie wurde gefunden, daß die Umsetzung nach zwei Stunden vollständig stattgefunden hatte. Die Destillation der Reaktionsmischung (nur für Zwecke der Identifizierung erforderlich) bei 380C/14,7 mbar (11 Torr) lieferte Trimethylsilyltrifluormethansulfonat (2) als farblose Flüssigkeit in annähernd quantitativer Ausbeute. Die Identifizierung erfolgte durch Vergleich mit einer im Handel erhältlichen Probe (Fluka): 1H-NMR (CDCl3):= 0,55 ppm (Morita et al., loc.cit.) Massenspektrum (70 eV): m/e 222 (M+), 207, 147, 77, 73, 69; Elementaranalyse Bei Versuchen wurde festgestellt, daß Trifluoressigsäure, die sich im Bezug auf ihre Azidität ähnlich wie Schwefelsäure verhält, auch bei höherer Temperatur nicht mit Tetramethylsilan reagierte. Dies zeigt, daß auch aus diesem Grund es überraschend ist, daß das erfindungsgemässe Verfahren zum Erfolg führt.On the basis of the monitoring by means of H-NMR spectroscopy it was found that the reaction had taken place completely after two hours. The distillation of the reaction mixture (only required for identification purposes) at 380C / 14.7 mbar (11 Torr) yielded trimethylsilyl trifluoromethanesulfonate (2) as a colorless liquid in almost quantitative yield. The identification was made by comparison with a commercially available sample (Fluka): 1H-NMR (CDCl3): = 0.55 ppm (Morita et al., loc. cit.) mass spectrum (70 eV): m / e 222 (M +), 207, 147, 77, 73, 69; Elemental analysis Tests have shown that trifluoroacetic acid, which is related to its acidity is similar to that of sulfuric acid, not even at higher temperatures reacted with tetramethylsilane. This shows that for this reason too it is surprising is that the inventive method leads to success.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823209416 DE3209416A1 (en) | 1982-03-16 | 1982-03-16 | Process for the preparation of trimethylsilyl trifluoromethanesulphonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823209416 DE3209416A1 (en) | 1982-03-16 | 1982-03-16 | Process for the preparation of trimethylsilyl trifluoromethanesulphonate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3209416A1 true DE3209416A1 (en) | 1983-09-22 |
Family
ID=6158323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823209416 Withdrawn DE3209416A1 (en) | 1982-03-16 | 1982-03-16 | Process for the preparation of trimethylsilyl trifluoromethanesulphonate |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3209416A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991002297A1 (en) * | 1989-07-31 | 1991-02-21 | Spectrum Sciences B.V. | Improved charge director compositions for liquid developers |
| WO1999043687A1 (en) * | 1998-02-27 | 1999-09-02 | Rhodia Chimie | Useful method for triflic acid silylation |
-
1982
- 1982-03-16 DE DE19823209416 patent/DE3209416A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991002297A1 (en) * | 1989-07-31 | 1991-02-21 | Spectrum Sciences B.V. | Improved charge director compositions for liquid developers |
| US5208130A (en) * | 1989-07-31 | 1993-05-04 | Spectrum Sciences B.V. | Charge director compositions for liquid developer |
| WO1999043687A1 (en) * | 1998-02-27 | 1999-09-02 | Rhodia Chimie | Useful method for triflic acid silylation |
| FR2775478A1 (en) * | 1998-02-27 | 1999-09-03 | Rhodia Chimie Sa | USEFUL PROCESS FOR THE SILYLATION OF TRIFLIC ACID |
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