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United States Patent Office Patented Apr 3,128,297 United States Patent Office Patented Apr. 7, 1964 1. 2 The various operable organo-silicon compounds, operable 3,128,297 catalysts and reaction conditions will now be defined in PROCESS FOR SELICON-HALOGEN BOND more detail. The term "halogen' as used herein includes RED STRIBUTION the elements fluorine, chlorine, bromine and iodine. Bernard Kanner, Tonawanda, and Donald L. Bailey, Sny Monomeric silanes which can be employed as reactants der, N.Y., assignors to Union Carbide Corporation, a in the process of this invention may be represented by corporation of New York No Drawing. Filed Mar. 31, 1961, Ser. No. 99,667 the formula: 20 Claims. (C. 260-448.2) (B) R (Y-R-) six This invention relates to a process for the redistribution 10 wherein R is a divalent hydrocarbon group, the Y group of silicon-halogen chemical bonds. More particularly, is hydrogen, fluoro, chloro, bromo, iodo, cyano, the invention is directed to a process for the redistribution O of silicon-fluorine and other silicon-halogen bonds, pref -COO G, -NG, G -O G, erably silicon-chlorine bonds, in organo-silicon com -V-va, pounds. This application is a continuation-in-part of our 5 or nitro, the R' group is hydrogen, the vinyl group or an copending application Serial No. 15,841, filed March 18, Y-R- group, X is a halogen, G is a monovalent hy 1960, now abandoned. drocarbon group, e is an integer having a value from 0 We have discovered that an efficient and rapid redis to 3, f is an integer having a value from 0 to 1 and the tribution of silicon-fluorine and other silicon-halogen sum of e and f is never greater than 3. bonds takes place at moderate temperatures when an or 20 The divalent hydrocarbon group R is preferably one gano-silicon compound or mixture of organo-silicon.com containing between one and 17 carbon atoms and may be pounds wherein there is at least one silicon-fluorine bond an alkylene group such as methylene, ethylene, butylene and at least one other different silicon-halogen bond is (1,4), hexylene (1,2), 2-ethylhexylene (1,6 and the like, contacted with a basic catalyst. For example, if trimeth a cycloalkylene group such as cyclopentylene (1,3), cyclo ylfluorosilane and methyltrichlorosilane are contacted 25 hexylene (1,4), 3-octylcyclohexylene (1,4) and the like and with triethylamine at about room temperature a redis an arylene or alkarylene group such as phenylene (1,4), tribution reaction takes place according to the equation: naphthalene (1,4), 2-ethylphenylene (1,4) (A) catalyst (CH3)2SiF -- CHSiCl3 e 30 (CH3)3SiCl -- CH3SiF Cl2 + CH3SiFC 1 - CH3SiF ÖH, The methods heretofore proposed for the redistribution of silicon-halogen bonds resulted in extremely slow CH CH, CH, GH, reactions even at relatively high temperatures. For ex / YoH- - /N ample, in J. Am. Chem. Soc., vol. 70, 3068, (1948), it 35 was reported that trimethylchlorosilane did not react with - ÖH, FSi(Me) CHSiMe2F to any detectable extent. When cí. , aluminum chloride, a Lewis acid, was added to the mix and the like. ture a very slow redistribution reaction took place at 40 The monovalent hydrocarbon group G is preferably one elevated temperatures. Another article in the J. Am. containing from one to 10 carbon atoms and may be Chem. Soc., vol. 72, 2091, (1950), reports that the re alkyl, cycloalkyl, aryl or alkaryl. Examples of the group distribution reaction involving SiC and SiF4 proceeded G are methyl, ethyl, isobutyl, hexyl, 2-ethylhexyl, cyclo very slowly even at 740 C. It was estimated that a tem pentyl, 2-ethylcyclohexyl, phenyl, tolyl, mesityl, cumyl, perature of 900° C. to 1000° C. would be required to and naphthyl. attain an equilibrium mixture of redistribution products 45 Typical monomers which can be employed in this within a reasonably short reaction time. It is, therefore, an object of this invention to provide process are a process for the redistribution of silicon-fluorine and silicon tetrachloride, other different silicon-halogen bonds in organo-silicon methyltrichlorosilane, compounds which is not subject to the disadvantages of 50 phenyltrichlorosilane, the methods heretofore known. naphthyltrichlorosilane, An additional object of this invention is to provide an ethyltrichlorosilane, efficient process for the production of organo-silicon com tricholorosilane, pounds containing silicon-fluorine and/or other silicon methyldichlorosilane, halogen bonds. 55 phenyldichlorosilane, A further object of this invention is to provide a process dimethyldichlorosilane, for producing organo-functional silicon halide compounds diphenyldichlorosilane, containing functional groups in the organic portion of phenylmethyldichlorosilane, the molecule. trimethylchlorosilane, A still further object of the invention is to provide a 60 phenyldimethylchlorosilane, process for the purification of chlorosilanes, bromosilanes dichlorosilane, and iodosilanes. bis-trichlorosilylbenzene, Other objects will be apparent from the following de tolydiphenylchlorosilane, tailed description and the appended claims. beta-cyanoethyltrichlorosilane, Broadly stated the process of this invention comprises 65 m-fluorophenylvinyldichlorosilane, contacting an organo-silicon compound or mixture of p-iodobenzyltrifluorosilane, organo-silicon compounds (provided, of course, that in nitrophenyltrichlorosilane, these organo-silicon compounds there is at least one sili bis-nitrophenyldichlorosilane, con-fluorine bond and at least one other different silicon cyanophenylmethyldichlorosilane, halogen bond) with a basic catalyst and heating the re 70 gamma-chloroisobutyltrichlorosilane, sulting mixture to a temperature sufficiently elevated to gamma-cyanopropyltrichlorosilane, cause the silicon-halogen bond redistribution to take place. beta-carbethoxyethyldichlorosilane, 3,128,297 3. 4. delta-nitrobutylmethyldichlorosilane, Also included in the operable monomeric silanes are 4-trichlorosilyl-N,N-dimethylbenzamide, mixed chloro-, bromo- iodo- and fluorosilanes such as di delta-bromobutyltrichlorosilane, methylfluorochlorosilane, 4-acetylphenylmethylchloro methoxyphenyltrichlorosilane, fluorosilane, phenyldichlorofluorosilane, beta-cyanoethyl phenyltrifluorosilane, 5 difluorochlorosilane, diethylchlorobromosilane, phenyl diphenylidifluorosilane, fluorobromoiodosilane and nitrophenylmethylfluoro silicon tetrafluoride, chlorosilane and the like. methylvinylidifluorosilane, Linear and cyclic polysiloxane polymers can also be beta-cyanoethyltrifluorosilane, used in the process of this invention. Operable linear gamma-chloroisobutyltrifluorosilane, 10 polysiloxanes can be represented by the formula: gamma-(N-methyl-N-phenylamino)propyltrifluorosilane, (C) R-Y R-Y beta-phenoxyethylmethylidifluorosilane,nitronaphthylmethylidifluorosilane, s -4-x. beta-phenylethyltrifluorosilane, R-Y y R-Y silicon tetrabromide, wherein R, Y and X have the meanings defined herein methyltribromosilane, above and y is an integer having a value from 1 to 10,000. phenyltribromosilane, Examples of operable linear siloxanes are 1,5-dichloro naphthyltribromosilane, hexamethyltrisiloxane, 1,3-dichlorotetramethyldisiloxane, ethyltribromosilane, 1,3-difluorotetraphenyltrisiloxane, 1,7-dichlorooctamethyl tribromosilane, ' tetrasiloxane, 1,5-dibromohexamethyltrisiloxane, 1-chloro, methyldibromosilane, 3-iodo-tetramethyldisiloxane, and the like. phenyldibromosilane, The cyclic polysiloxane polymers which can be em dimethyldibromosilane, ployed in the process of this invention may be represented diphenyldibromosilane, by the formula: phenylmethyldibromosilane, 25 s trimethylbromosilane, (D) 1–Y phenyldimethylbromosilane, -Si-O -Si-O dibromosilane, k-y r k-y s tolydiphenylbromosilane, beta-cyanoethyltribromosilane, 30 wherein R, Y,X have the meanings defined hereinabove, beta-carbethoxyethylmethyldibromosilane, r is an integer having a value from 1 to 3 and s is an nitrophenyltribromosilane, integer having a value from 2 to 10 with a preferred bis-nitrophenyldibromosilane, range of from 2 to 4. Examples of operable cyclic poly cyanophenylmethyldibromosilane, siloxanes include chloroheptamethylcyclotetrasiloxane, gamma-chloroisobutyltribromosilane, 35 chloropentamethylcyclotrisiloxane, iodopentamethylcyclo beta-carbethoxypropyltribromosilane, trisiloxane, dibromohexamethylcyclotetrasiloxane, fluoro gamma-cyanopropyltrichlorosilane, heptaethylcyclotetrasiloxane, and the like. delta-nitrobutylmethyldibromosilane, The redistribution process of this invention applies to delta-N,N-dimethylaminobutyldimethylbromosilane, mixtures of silanes, linear polysiloxanes and cyclic poly delta-bromobutyltribromosilane, 40 siloxanes, and includes the redistribution of silicon N,N-diethylaminophenylmethyldibromosilane, fluorine bonds with mixtures of silicon-chlorine, silicon methoxyphenyltribromosilane, bromine and silicon-iodine bonds. beta-methoxyethylmethyldibromosilane, The operable basic catalysts in the process of the pres delta-ethylmercaptobutyltribromosilane, ent invention are tertiary amines, tri(monovalent hydro silicon tetraiodide, 45 carbon group) phosphines and silylamines. The term methyltriiodosilane, "tertiary amine” as used herein means a class of com phenyltriiodosilane, pounds wherein all three normal valences of the nitrogen naphthyltriiodosilane, atoms in Such compounds are bonded to carbon atoms ethyltriiodosilane, of hydrocarbon moieties. Thus, the term “tertiary triiodosilane, 50 amines' includes tri(monovalent hydrocarbon group) methyldiiodosilane, amines and pyridines, for example, triethylamine triso phenyldiiodosilane, propylamine,
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