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Method for the Preparation of Cyclopentyl Trichlorosilane

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Method for the Preparation of Cyclopentyl Trichlorosilane Europaisches Patentamt (19) European Patent Office Office europeenpeen des brevets EP 0 460 589 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.e: C07F 7/14 of the grant of the patent: 04.11.1998 Bulletin 1998/45 (21) Application number: 91109082.7 (22) Date of filing: 04.06.1991 (54) Method for the preparation of cyclopentyl Trichlorosilane Verfahren zur Herstellung von Cyclopentyl-trichlorosilan Procede de preparation de cyclopentyl trichlorosilane (84) Designated Contracting States: (74) Representative: DE FR GB IT Luderschmidt, Schiiler & Partner GbR Patentanwalte, (30) Priority: 07.06.1990 JP 149338/90 Postfach 3929 65029 Wiesbaden (DE) (43) Date of publication of application: 11.12.1991 Bulletin 1991/50 (56) References cited: EP-A- 0 278 863 DE-A- 1 941 411 (73) Proprietor: SHIN-ETSU CHEMICAL CO., LTD. GB-A-2 013 207 Chiyoda-ku Tokyo (JP) • CHEMICAL ABSTRACTS vol. 89, no. 17, 23 (72) Inventors: October 1 978, page 61 9, abstract no. 1 46975f , • Shinohara, Toshio Columbus, Ohio, US; R.A. BENKESER: Takasaki-shi, Gunma-ken (JP) "Chloroplatinic acid catalyzed additions of • Iwabuchi, Motoaki silanes to isoprene" Annaka-shi, Gunma-ken (JP) DO O) 00 CO ^- Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice the Patent Office of the Notice of shall be filed in o to European opposition to European patent granted. opposition a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. a. 99(1) European Patent Convention). LU Printed by Jouve, 75001 PARIS (FR) 1 EP 0 460 589 B1 2 Description such as chloroplatinic acid as a catalyst according to a procedure well known in the hydrosilation between a sil- BACKGROUND OF THE INVENTION icon compound having a silicon-bonded hydrogen atom and a linear alkenyl compound. Different from other cy- The present invention relates to a method for the 5 cloalkene compounds such as cyclohexene of a 6-mem- synthetic preparation of cyclopentyl trichlorosilane or, bered ring, nevertheless, no report is found in the liter- more particularly, to a method for the preparation of cy- atures for the hydrosilation reaction of cyclopentene clopentyl trichlorosilane from trichlorosilane and cy- with trichlorosilane. This is presumably due to the low clopentene by the hydrosilation reaction. reactivity of cyclopentene even by the catalytic promo- Cyclopentyl trichlorosilane is a compound having 10 tion of the reaction by conventional platinum catalysts. usefulness as an intermediate in the synthetic prepara- EP-A-0 278 863 discloses the reaction of cyclopen- tion of various kinds of organosilicon compounds having tene with trichlorosilane in the presence of a platinum two or three cycloalkyl groups in a molecule. Since cy- catalyst prepared from chloroplatinic acid and an alco- clopentyl-containing organosilicon compounds have a hol. Acceptable yields of cyclopentyl trichlorosilane are refractive index intermediate between those of methyl- is only obtained under UV-irradiation. and phenyl-containing organosilicon compounds, an advantage is expected in matching of the refractive in- SUMMARY OF THE INVENTION dices when a transparent silicone composition is de- sired. Further, the bulkiness of the cyclopentyl group The present invention accordingly has an object to promisingly indicates the usefulness of cyclopentyl-con- 20 provide a novel and efficient method for the synthetic taining silane compounds as a silylating agent in various preparation of cyclopentyl trichlorosilane by the hydrosi- organic syntheses for which tert-butyl dimethyl chlorosi- lation reaction between trichlorosilane and cyclopen- lane is the most conventional. Several methods are tene without the problems and disadvantages in the known in the prior art for the preparation of this com- above described prior art methods such as the "direct pound. For example, the so-called "direct method" pro- 25 method" and the Grignard method. posed by E.G. Rochow is also applicable to the prepa- Thus, the method of the present invention for the ration of this silane compound in which metallic silicon preparation of cyclopentyl trichlorosilane comprises the and cyclopentyl chloride are reacted in the presence of steps of: a copper catalyst. Alternatively, it can be synthesized by the reaction of cyclopentyl magnesium halide as a Grig- 30 (a) mixing trichlorosilane, cyclopentene and a plat- nard reagent with tetrachlorosilane. inum catalyst, which is a reaction product of chloro- The above mentioned "direct method" is not advan- platinic acid with a basic compound so as to de- tageous when the organosilane compound to be pre- crease the atomic ratio of chlorine to platinum in the pared is cyclopentyl trichlorosilane because by-prod- range from 0.001 to 0. 1 , to form a reaction mixture; ucts are formed in large amounts so that great difficulties 35 and are encountered in the isolation and purification of cy- (b) heating the reaction mixture at a temperature clopentyl trichlorosilane. The Grignard method has an higher by at least 1°C than the boiling point of the economical disadvantage as an industrial method due reaction mixture under normal pressure or, prefer- to the expensiveness of the Grignard reagent in addition ably, in the range from 50 to 80°C. to the problem of troublesomeness and danger of fire or 40 explosion accompanying the use of a very inflammable DETAILED DESCRIPTION OF THE PREFERRED organic solvent such as ether. Moreover, the productiv- EMBODIMENTS ity of the Grignard method cannot be high enough due to the formation of a large amount of a magnesium hal- As is understood from the above description, the ide as the by-product which must be removed from the 45 most characteristic feature of the inventive method for reaction mixture. Further, the Grignard reagent, i.e. cy- the hydrosilation reac-tion consists in the use of a very clopentyl magnesium halide, is highly susceptible to ox- specific platinum catalyst and in the specific reaction idation by oxygen in the atmospheric air to be converted conditions relative to the temperature. into cyclopentyloxy magnesium halide from which cy- While the amounts of trichlorosilane and cyclopen- clopentyloxy trichlorosilane is formed as the product of so50 tene pertaining to the hydrosilation reaction are equimo- the Grignard reaction while this compound can hardly lar, the molar ratio of cyclopentene to trichlorosilane in be separated from cyclopentyl trichlorosilane, for exam- the reaction mixture should be in the range from 0.6 to ple, by distillation because these two compounds have 1 .5 or, preferably, from 0.9 to 1 .1 from the standpoint of physical properties very close to each other. productivity of the process. When one of the reactants It would be a speculatively possible way that cy- 55 is used in an excessive amount over equimolar, a por- clopentyl trichlorosilane could be prepared by the hy- tion of the reactant remains unreacted in the reaction drosilation reaction between trichlorosilane and cy- mixture after completion of the reaction as a matter of clopentene in the presence of a platinum compound course and must be removed from the mixture to isolate 2 3 EP 0 460 589 B1 4 the cyclopentyl trichlorosilane as the product. When the sure-resistance of the reac-tion vessel.. reaction is performed under appropriately selected con- In the following, the method of the present invention ditions according to the inventive method, the reac-tion is described in more detail by way of examples. proceeds almost quantitatively with formation of very small amounts of by-products. 5 Example 1 . Different from the platinum catalysts conventionally used in the hydrosilation reaction, the platinum catalyst The atomic ratio of chlorine to platinum was 0.05 in used in the inventive method is a chlorine-deficient chlo- the chlorine-deficient chloroplatinic acid catalyst, re- roplatinic acid catalyst, of which the atomic ratio of chlo- ferred to as the catalyst I hereinbelow, used in this ex- rine to platinum is in the range from 0.001 to 0. 1 . When 10 ample, which was prepared by treating chloroplatinic ac- conventional chloroplatinic acid or chloroplatinous acid, id hexahydrate with sodium hydrogen-carbonate and in which the atomic ratio of chlorine to platinum is 6 or was in the form of a solution in toluene in a concentration 4, respectively, is used as such as the catalyst for the of 0.5% by weight as platinum. hydrosilation reaction between trichlorosilane and cy- Into an autoclave of 2-liter capacity were introduced clopentene, the extent of the reaction can rarely exceed is 1 41 g (1 .04 moles) of trichlorosilane, 71 g (1 .04 moles) 20%. It was discovered quite unexpectedly that the hy- of cyclopentene and 4.1 g of the catalyst I mentioned drosilation reaction could proceed almost to complete- above corresponding to 97 ppm by weight as platinum ness when the catalyst was a chlorine-deficient chloro- based on the total amount of trichlorosilane and cy- platinic acid catalyst of which the atomic ratio of chlorine clopentene to form a reaction mixture, which was heated to platinum was in the above specific range. Such a chlo- 20 at 65 to 75 °C for 24 hours under a spontaneously pro- rine-deficient chloroplatinic acid catalyst can be pre- duced pressure of about 4 kg/cm2G. Small portions of pared by the treatment of chloroplatinic acid with sodium the reaction mixture were periodically taken out of the hydrogencarbonate and an organosiloxane compound autoclave and analyzed by the gas chromatography to having a silicon-bonded vinyl group in a molecule ac- monitor progress of the reaction. More than 99% of the cording to the disclosure in Japanese Patent Publication 25 starting reactants had been reacted at the end of the 47-23679.
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