EP0000184A1 - Procédé de transformation d'organosilanes - Google Patents

Procédé de transformation d'organosilanes Download PDF

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Publication number
EP0000184A1
EP0000184A1 EP78100222A EP78100222A EP0000184A1 EP 0000184 A1 EP0000184 A1 EP 0000184A1 EP 78100222 A EP78100222 A EP 78100222A EP 78100222 A EP78100222 A EP 78100222A EP 0000184 A1 EP0000184 A1 EP 0000184A1
Authority
EP
European Patent Office
Prior art keywords
general formula
silane
carbon atoms
hydrogen
hydrocarbon radicals
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.)
Granted
Application number
EP78100222A
Other languages
German (de)
English (en)
Other versions
EP0000184B1 (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
Original Assignee
Wacker Chemie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP0000184A1 publication Critical patent/EP0000184A1/fr
Application granted granted Critical
Publication of EP0000184B1 publication Critical patent/EP0000184B1/fr
Expired legal-status Critical Current

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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

  • the invention relates to an improvement in the process for converting organosilanes by reacting at least one silane (I) of the general formula with at least one of (I) different silane (II) of the general formula where R is in each case the same or different, free from aliphatic multiple bonds, carbon dioxide residues with 1 to 10 carbon atoms, 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.
  • the improvement is, for example, that the process according to the invention can be carried out at a considerably lower temperature.
  • the improvement is achieved in that in the process according to the invention at least one silane (III) 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 (I), (II) and (III), hydrogen halide can also be used.
  • organosilanes by reacting at least one silane (I) of the general formula with at least one of (I) different silane (II) of the general formula where R is in each case the same or different hydrocarbon radicals with 1 to 10, free of aliphatic multiple bonds Carbon atoms means a is 2, 3 or 4 and b is O, 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, for example, the combination of aluminum chloride and silane with at least one Si-bonded hydrogen atom (see, for example, US Pat. No.
  • GB-PS 8 51 868 published: October 19, 1960, applicant: Imperial Chemical Industries Limited, which GB-PS corresponds to FR-PS 12 04 830 of the same applicant, published: January 28, 1960).
  • the method according to the invention has the advantages, for example, that it can be carried out without using excess pressure, 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 (I) of the general formula with at least one of (I) different silane (II) of the general formula wherein each R is the same or different, aliphatic M ehrfachitatien free hydrocarbon radicals having 1 to 10 carbon atoms, a 2, 3 or 4 and b is 0, 1, 2 or 3, in the presence of at least one Organoaluminiumver - 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 (III) of the general formula where R,
  • 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 radicals, such as the phenyl radical; Aralkyl radicals, such as the benzyl radical; and alkaryl groups such as tolyl groups.
  • 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 radicals such as the phenyl radical
  • Aralkyl radicals such as the benzyl radical
  • alkaryl groups such
  • silanes of the general formulas R a SiCl 4-a (I) and R b SiCl 4-b (II) are trimethylchlorosilane, dimethyldichlorosilane, methyltrichlorosilane, diphenyldichlorosilane, ethyltrichlorosilane, n-propyltrichlorosilane, phenyltrichlorosilane, phenyltrichlorosilane, n-pentillorosilane, Pentyltrichlorosilane, cycldhexyltrichlorosilane and methylethyldichlorosilane.
  • silanes (I) of the general formula R a SiCl 4-a are tetramethylsilane and tetraphenylsilane.
  • Formula R b SiCl 4-b can also be tetrachlorosilane.
  • Silane (I) of the general formula R a SiCl 4-a is preferably used in amounts of 0.8 to 1.2 mol per mole of silane (II) of the general formula R b SiCl 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 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 sesguichloride is particularly preferred.
  • silanes (III) of the general formula R b H c SiCl 4-bc are silane, methyldichlorosilane, dimethylchlorosilane, trichlorosilane and monochlorosilane.
  • Silane (III) 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 the silanes (I) and (II).
  • 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% of dimethyldichlorosilane is found.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 true EP0000184A1 (fr) 1979-01-10
EP0000184B1 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)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2505843A1 (fr) * 1981-05-15 1982-11-19 Wacker Chemie Gmbh Procede pour methyler des composes du silicium
EP0747384A1 (fr) * 1995-06-07 1996-12-11 Hüls Aktiengesellschaft Procédé de préparation d'alkylhydrogènechlorosilanes
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

Families Citing this family (9)

* 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
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
CN101531674B (zh) * 2009-04-23 2012-02-15 嘉兴学院 一种甲基氯硅烷的制备方法
EP3345866B1 (fr) * 2014-12-15 2021-10-06 Evonik Operations GmbH Procédé de fabrication d'un composé de silane cyclique
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
CN113454094B (zh) 2019-07-10 2024-03-22 瓦克化学股份公司 用于转化有机硅烷的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1111184B (de) * 1959-07-31 1961-07-20 Ici Ltd Verfahren zur Disproportionierung von organosilanhaltigen Mischungen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1111184B (de) * 1959-07-31 1961-07-20 Ici Ltd Verfahren zur Disproportionierung von organosilanhaltigen Mischungen

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2505843A1 (fr) * 1981-05-15 1982-11-19 Wacker Chemie Gmbh Procede pour methyler des composes du silicium
EP0747384A1 (fr) * 1995-06-07 1996-12-11 Hüls Aktiengesellschaft Procédé de préparation d'alkylhydrogènechlorosilanes
US5654459A (en) * 1995-06-07 1997-08-05 Huels Aktiengesellschaft Process for preparing alkylhydrogenchlorosilanes
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

Also Published As

Publication number Publication date
EP0000184B1 (fr) 1980-07-23
CA1110646A (fr) 1981-10-13
DE2728196B2 (de) 1979-06-07
BR7803931A (pt) 1979-02-20
JPS5711915B2 (fr) 1982-03-08
DE2860047D1 (en) 1980-11-13
IT1105418B (it) 1985-11-04
DE2728196A1 (de) 1979-01-04
US4158010A (en) 1979-06-12
JPS549229A (en) 1979-01-24
IT7849967A0 (it) 1978-06-21
DE2728196C3 (de) 1980-01-31
DD133951A5 (de) 1979-01-31

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