EP0000184B1 - Procédé de transformation d'organosilanes - Google Patents

Procédé de transformation d'organosilanes Download PDF

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Publication number
EP0000184B1
EP0000184B1 EP78100222A EP78100222A EP0000184B1 EP 0000184 B1 EP0000184 B1 EP 0000184B1 EP 78100222 A EP78100222 A EP 78100222A EP 78100222 A EP78100222 A EP 78100222A EP 0000184 B1 EP0000184 B1 EP 0000184B1
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EP
European Patent Office
Prior art keywords
general formula
silane
hydrogen
carbon atoms
silanes
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
Application number
EP78100222A
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German (de)
English (en)
Other versions
EP0000184A1 (fr
Inventor
Werner Dr. Graf
Peter Dr. John
Volker Dr. Frey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
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Wacker Chemie AG
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Publication date
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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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0801—General processes
    • 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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/0827—Syntheses with formation of a Si-C bond
    • 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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
    • C07F7/125—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution reactions

Definitions

  • organosilanes can be reacted with at least one silane (1) of the general formula. with at least one of (1) different silane (II) of the general formula where R in each case denotes the same or different hydrocarbon radicals having 1 to 10 carbon atoms and free of aliphatic multiple bonds, a is 2, 3 or 4 and b is 0, 1, 2 or 3. It is also known to promote this reaction, which is referred to as "coproportionation” according to Noll, "Chemistry and Technology of Silicones", Weinheim, 1968, page 51/52, by catalysts. These catalysts include e.g. B.
  • one of the silanes used as reactants can contain Si-bonded hydrogen (see, for example, DE-AS 1 111 184, applicant: Imperial Chemical Industries Limited), the combination of aluminum chloride and silane at least one Si-bonded hydrogen atom (see, for example, US Pat. No. 2,786,861, issued; March 23, 1957, HR McEntee, assignor to General Electric Company, this US Pat. No.
  • the process according to the invention has the advantages, for example, that it can be carried out without using overpressure, at lower temperatures and with smaller amounts of aluminum compounds. Even with the method according to the invention, the disadvantages associated with the use of aluminum chloride, already known from GB-PS 8 51 868, cannot occur.
  • the invention relates to a process for converting organosilanes by reacting at least one silane (1) of the general formula. with at least one of (1) different silane (11) of the general formula where R is in each case the same or different hydrocarbon radicals having 1 to 10 carbon atoms and free from aliphatic multiple bonds, a is 2, 3 or 4 and b is 0, 1, 2 or 3, in the presence of at least one organoaluminum compound of the general formula where R 1 is the same or different alkyl radicals having 1 to 4 carbon atoms, Y halogen, hydrogen or oxygen-bonded to the aluminum atom, free from aliphatic multiple bonds, hydrocarbon radicals having 1 to 10 carbon atoms and c is 1, 2 or 3, characterized in that at least a silane (111) of the general formula where R, b and c each have the meaning given above with the proviso that the sum of b + c is at most 4, and 0.1 to 5 percent by weight, based on the total weight of the silanes (1), (11) and
  • hydrocarbon radicals R and Y are alkyl radicals, such as the methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and the 2-ethylhexyl radical and decyl radicals; Cycloalkyl radicals, such as the cyclohexyl radical; Aryl residues like that Phenyl radical; Aralkyl radicals, such as the benzyl radical; and alkaryl groups such as tolyl groups.
  • silanes of the general forms in R a SiCl 4-a (I) and R b SiCl 4-b (11) are trimethylchlorosilane, dimethyldichlorosilane, methyltrichlorosilane, diphenyldichlorosilane, ethyltrichlorosilane, n-propyltrichlorosilane, phenyltrichlorosilane, phenyltrichlorosilane, nyltrichlorosilane, Pentyltrichlorosilane, cyclohexyltrichlorosilane and methyl-ethyldichlorosilane.
  • silanes (1) of the general formula R a SiCl 4-a are tetramethylsilane and tetraphenylsilane.
  • the silane (11) of the general formula R b SiCl 4-b can also be tetrachlorosilane.
  • Silane (1) of the general formula R a SiCl 4-e is preferably used in amounts of 0.8 to 1.2 mol per mole of silane (11) of the general formula R b SiC1 4-b .
  • hydrocarbon radicals R and Y with 1 to 4 carbon atoms also apply in full to the hydrocarbon radicals R 1 .
  • hydrocarbon radicals R 1 and Y are tert-butyl radical.
  • Halogen Y chlorine is preferred because of its easy accessibility.
  • Halogen atoms Y can also be fluorine, bromine or iodine.
  • Preferred organoaluminum compounds are those with a boiling point above 150 ° C. at 760 mm Hg (abs.). Because of the easy accessibility, ethyl aluminum sesquichloride is particularly preferred.
  • Formula R b H c SiCI 4-bc are silane, methyldichlorosilane, dimethylchlorosilane, trichlorosilane and monochlorosilane.
  • Silane (111) is preferably used in amounts of 0.5 to 15 percent by weight, in particular 2 to 6 percent by weight, based in each case on the total weight of silanes (1) and (11).
  • hydrogen chloride is preferred as the hydrogen halide.
  • hydrogen fluoride hydrogen bromide and / or hydrogen iodide can also be used.
  • the process according to the invention can be carried out at room temperature and the pressure of the surrounding atmosphere, ie the 760 mm Hg (abs.) Or about 760 mm Hg (abs.).
  • higher temperatures can also be used, e.g. up to 450 ° C.
  • temperatures of at most 150 ° C. are preferred. If the use of higher temperatures and the boiling points of the reactants so require, pressure and / or a high-boiling solvent which is inert to the other constituents of the reaction mixture, e.g. a mixture of alkanes with a boiling point of at least 150 ° C at 760 mm Hg (abs.) can be used.
  • Water is preferably excluded as far as possible
  • the process according to the invention can be carried out batchwise, semi-continuously or fully continuously.
  • Example 2 The procedure described in Example 1 is repeated with the modification that no hydrogen halide is used. When determining the composition of the reaction mixture by gas chromatography, only about 1% trimethylchlorosilane is found.
  • Example 2 The procedure described in Example 2 is repeated with the modification that no silane with Si-bonded hydrogen is used. When determining the composition of the reaction mixture by gas chromatography, only less than 3,996 dimethyldichlorosilane are found.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (2)

1. Procédé de transformation d'organosilanes par réaction d'au moins un silane (1) de la formule générale
Figure imgb0017
avec au moins un silane (II) étant différent du silane (I) de la formule générale
Figure imgb0018
R représentant chacun des radicaux hydrocarbures identiques ou différents, étant libres de composés multiples aliphatiques, et comportant 1 à 10 atomes de carbone, a étant 2, 3 ou 4, et b étant 0, 1, 2 ou 3 en présence d'au moins une combinaison organoaluminium de la formule générale
Figure imgb0019
dans laquelle RI resrésente des radicaux alkyle identiques ou différents, comportant 1 à 4 atomes de carbone, Y représente du halogène, de l'hydrogène ou des radicaux hydrocarbures comportant 1 à 10 atomes de carbone, étant libres de composés multiples aliphatiques, et releis à l'atome d'aluminium par l'intermédiaire de l'oxygène, c est égal à 1, 2 ou 3, caracterisé en ce que l'on utilise en outre au moins un silane (III) de la formule générale
Figure imgb0020
dans laquelle R,b et c correspondent chacun aux définitions précitées dans la mesure où la somme de b + c est au maximum 4, et 0.1 à 5% en poids-ces proportions étant rapportées à la quantité totale des silanes (1), (II) et (Ili)-de halide d'hydrogène.
2. Procédé selon la revendication 1 caracterisé en ce qu'en tant que halide d'hydrogène, on utilise de l'acide chlorhydrique.
EP78100222A 1977-06-23 1978-06-23 Procédé de transformation d'organosilanes Expired EP0000184B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2728196A DE2728196C3 (de) 1977-06-23 1977-06-23 Verfahren zur Umwandlung von Organosilanen
DE2728196 1977-06-23

Publications (2)

Publication Number Publication Date
EP0000184A1 EP0000184A1 (fr) 1979-01-10
EP0000184B1 true EP0000184B1 (fr) 1980-07-23

Family

ID=6012137

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100222A Expired EP0000184B1 (fr) 1977-06-23 1978-06-23 Procédé de transformation d'organosilanes

Country Status (8)

Country Link
US (1) US4158010A (fr)
EP (1) EP0000184B1 (fr)
JP (1) JPS549229A (fr)
BR (1) BR7803931A (fr)
CA (1) CA1110646A (fr)
DD (1) DD133951A5 (fr)
DE (2) DE2728196C3 (fr)
IT (1) IT1105418B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5798531A (en) * 1980-12-11 1982-06-18 Kanebo Synthetic Fibers Ltd Porous film
DE3208829A1 (de) * 1981-05-15 1982-12-02 Wacker-Chemie GmbH, 8000 München Verfahren zum methylieren von siliciumverbindungen
GB2101620A (en) * 1981-05-15 1983-01-19 Wacker Chemie Gmbh Process for methylating silicon compounds
US4889838A (en) * 1983-12-22 1989-12-26 Union Carbide Corporation And Plastics Company Inc. Redistribution of organohalosilanes utilizing heat treated crystalline alumina catalysts
US4946980A (en) * 1988-10-17 1990-08-07 Dow Corning Corporation Preparation of organosilanes
US4962219A (en) * 1988-10-17 1990-10-09 Dow Corning Corporation Alkylation of halodisilanes
DE19520737C2 (de) * 1995-06-07 2003-04-24 Degussa Verfahren zur Herstellung von Alkylhydrogenchlorsilanen
CN101531674B (zh) * 2009-04-23 2012-02-15 嘉兴学院 一种甲基氯硅烷的制备方法
CN102276641A (zh) * 2011-09-15 2011-12-14 江苏弘博新材料有限公司 甲基氯硅烷的生产方法
US10858260B2 (en) * 2014-12-15 2020-12-08 Evonik Operations Gmbh Method for producing perhalogenated hexasilane anion and method for producing a cyclic silane compound
DE102016117519A1 (de) 2016-09-16 2018-03-22 Osram Opto Semiconductors Gmbh Verfahren zur Herstellung eines Siloxans, Verfahren zur Herstellung eines Polysiloxans, Verfahren zum Vergießen von optoelektronischen Bauelementen
EP3911657B1 (fr) 2019-07-10 2023-01-04 Wacker Chemie AG Procédé de conversion d'organosilanes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB881698A (en) * 1959-07-31 1961-11-08 Ici Ltd Organohalogenosilanes
US3769310A (en) * 1972-06-07 1973-10-30 Gen Electric Redistribution of alkylhydrosilanes
US3793357A (en) * 1972-10-20 1974-02-19 Gen Electric Process for the redistribution of alkylsilanes and alkylhydrosilanes
FR2279755A1 (fr) * 1974-07-26 1976-02-20 Rhone Poulenc Ind Procede de preparation de chlorosilanes et emploi des chlorosilanes ainsi obtenus

Also Published As

Publication number Publication date
DE2860047D1 (en) 1980-11-13
BR7803931A (pt) 1979-02-20
JPS5711915B2 (fr) 1982-03-08
DE2728196C3 (de) 1980-01-31
EP0000184A1 (fr) 1979-01-10
DD133951A5 (de) 1979-01-31
IT1105418B (it) 1985-11-04
IT7849967A0 (it) 1978-06-21
JPS549229A (en) 1979-01-24
CA1110646A (fr) 1981-10-13
DE2728196B2 (de) 1979-06-07
DE2728196A1 (de) 1979-01-04
US4158010A (en) 1979-06-12

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