EP2049553A1 - Verfahren zur herstellung von siliciumorganischen verbindungen durch hydrosilylierung in ionischen flüssigkeiten - Google Patents

Verfahren zur herstellung von siliciumorganischen verbindungen durch hydrosilylierung in ionischen flüssigkeiten

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Publication number
EP2049553A1
EP2049553A1 EP07765548A EP07765548A EP2049553A1 EP 2049553 A1 EP2049553 A1 EP 2049553A1 EP 07765548 A EP07765548 A EP 07765548A EP 07765548 A EP07765548 A EP 07765548A EP 2049553 A1 EP2049553 A1 EP 2049553A1
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EP
European Patent Office
Prior art keywords
general formula
reaction
catalyst
hydrosilylation
ionic
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Withdrawn
Application number
EP07765548A
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German (de)
English (en)
French (fr)
Inventor
Andreas Bauer
Thomas Frey
Peter Wasserscheid
Peter Schulz
Norbert Hofmann
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Wacker Chemie AG
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Wacker Chemie AG
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Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP2049553A1 publication Critical patent/EP2049553A1/de
Withdrawn legal-status Critical Current

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    • 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
    • C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
    • 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
    • C07F7/0829—Hydrosilylation reactions
    • 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
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages

Definitions

  • the invention relates to a process for the preparation of organosilicon compounds by hydrosilylation in ionic liquids.
  • organosilicon compounds are carried out according to the prior art after the Muller-Rochow synthesis.
  • the functionalized organosilanes are of great economic importance, in particular halogen-substituted ones, since they serve as starting materials for the preparation of many important products, for example silicones, adhesion promoters, water repellents and building protection agents.
  • One way to prepare manganese silanes is to convert easily prepared silanes (excess silanes) to manganese silanes by a ligand exchange reaction.
  • ionic liquids in the two-phase system for ligand exchange of organochlorosilanes with other organochlorosilanes and is described for example in the patent DE 101 57 198 Al.
  • a ligand exchange reaction takes place on the silicon atom, in which an organosilane in the presence of an ionic liquid, which is a halide,
  • Metal or transition metal halide of organic nitrogen or phosphorus compounds, disproportionated or with another organosilane is reacted under ligand exchange.
  • Ionic liquids are generally understood to mean salts or mixtures of salts whose melting points are below 100 ° C., as described, for example, in P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926.
  • Literature-known salts of this type consist of anions such as halogenostannates, halogenoaluminates, hexafluorophosphates, tetrafluoroborates, alkyl sulfates, alkyl or aryl sulfonates, dialkyl phosphates, rhodanides or dicyanamides combined with substituted ammonium, phosphonium, imidazolium, pyridinium, pyrazolium, triazolium, picolinium - or pyrrolidinium cations.
  • Numerous publications already describe the use of ionic liquids as solvents for
  • Transition metal catalyzed reactions such as T. Welton, Chem. Rev. 1999, 99, 2071, and P. Wasserscheid, W. Keim, Angew. Chem., 2000, 112, 3926, and P. Wasserscheid, T. Welton (Eds.) &Quot; Ionic Liquids in Synthesis ", 2003, Wiley-VCH, Weinheim, pp 213-257
  • Improvements are also of considerable technical relevance and occur, for example, in a significantly improved catalyst removability and catalyst reuse, a significantly increased catalyst stability, a significantly increased reactivity or a significantly improved
  • ionic liquids offer the possibility of a gradual coordination of relevant structural variations Solvent properties towards a specific application goal.
  • the hydrosilylation of 1-alkenes is known to be catalyzed by platinum group metal complexes as described, for example, in J. Marciniec, "Comprehensive Handbook on Hydrosilylation", Pergamon Press, New York 1992.
  • platinum complexes such as the so-called “Speier catalyst” [H 2 PtCl 6 * 6 H 2 O] and the "Karstedt solution", a complex compound of [H 2 PtCl 6 * 6 H 2 O] and vinyl-substituted disiloxanes, are known to be very active catalysts in that with the use of some anhydrous platinum compounds, for example dicycloocadienylplatinum ([Pt (cod) 2 ]), platinum colloids are formed, which are also highly active hydrosilylation catalysts as described, for example, in LN Lewis, N. Lewis, J. Am. Chem Soc., 1986, 108, 7728.
  • Performing the hydrosilylation reaction as a liquid-liquid two-phase reaction requires a system with a polar and a nonpolar solvent in which both solvents have a miscibility gap.
  • the systems cyclohexane / propene were published as nonpolar and cyclohexane / propylene carbonate as the polar phase in A. Behr, N. Toslu, Chem. Eng. Technol. 2000, 23, 2.
  • this system for example, the hydrosilylation of ⁇ -undecenoic acid with triethoxysilane, where the product is enriched in the non-polar phase and can be easily separated from the catalyst and the starting materials which remain in the polar phase.
  • SILP supported ionic liquid phase
  • SILP catalyst technology the solution of a transition metal complex in an ionic liquid is applied to a mostly highly porous carrier, by physisorption or chemical reaction, and the resulting solid catalyst is contacted with the reactants in a gas phase or liquid phase reaction.
  • This technology represents a new approach to combining the advantages of classical homogeneous catalysis with those of classical heterogeneous catalysis.
  • Catalyst solution on a porous solid it is achieved that without high input of mechanical energy to the reactants a high specific surface of ionic catalyst solution is ready for reaction.
  • the catalyst is still homogeneous dissolved here.
  • the technology also provides very easy access to continuous processes, for example, in A. Riisager, P. Wasserscheid, R. van HaI, R. Fehrmann, J. Catal. 2003, 219, 252.
  • SILP technology Interactions of the active surface groups of the porous support with the transition metal catalyst in only a few nanometers thick carrier film, the successful use of SILP technology for the skilled person not obvious.
  • Other known applications of SILP technology include
  • the object of the invention was therefore to provide a process for the preparation of silanes by hydrosilylation, which proceeds very selectively and thus leads to high yields of the desired silanes.
  • This object has been achieved by the process according to the invention for the preparation of silanes by hydrosilylation, which is characterized in that the catalyst used for the hydrosilylation reaction is a transition metal complex compound which is dissolved in an ionic liquid during the reaction.
  • An advantage of the novel process according to this invention is the technical possibility of catalyst separation and recirculation in the liquid-liquid multiphase system or in variants in which the ionic catalyst solution is applied to solids.
  • a achieved significant selectivity improvement in silane synthesis in many cases compared to the known synthesis method a achieved significant selectivity improvement in silane synthesis.
  • R is independently a H, a monovalent Si-C-bonded, optionally halogen-substituted C] _-C] _g-
  • R 8 , R 9 , R 10 and R 11 are independently H, a monovalent optionally with F , Cl, OR, NR 2, CN or NCO substituted C] _C] _g hydrocarbon, chlorine, fluorine or C] _- C] _g alkoxy radical, wherein in each case 2 radicals of R 8 , R 9 , R 10 and R 11 together with the carbon atoms to which they are attached can form a cyclic radical.
  • those of the general formula (3) are preferably reacted as non-polymeric compounds
  • R carries the meaning given above, and c the values 0, 1, 2, 3 or 4 and d can have the values 1, 2 or 3.
  • Such a superposition of hydrosilylation, disportportionation, and ligand exchange reaction should thus technically facilitate the preparative use of hydrosilylation of non-polymeric compounds bearing one or more H-Si functionality (s) with unsaturated compounds using ionic catalyst solutions in the liquid-liquid multiphase system to make something useless.
  • Formula (1) which carry one or more H-Si functionality (s), is preferably carried out with such alkenes, in addition to Carbon and hydrogen may still contain chlorine, alkoxy or amino functionalities.
  • the instant process of this invention demonstrates an unexpected technical solution based on the discovery that the solution of a transition metal complex used as a hydrosilylation catalyst in an ionic liquid surprisingly catalyzes selectively a hydrosilylation of non-polymeric Si-H compounds in a multi-phase reaction regime.
  • the process according to this invention also offers a technically reliable possibility of catalyst separation and recirculation in the liquid-liquid two-phase system. With multiple recirculation of the ionic liquid, only slight changes in the activity and selectivity of the ionic catalyst solution are observed. In the preferred variants of the method according to the invention which are shown below, the changes are particularly slight.
  • Si-H compounds according to the Formula (3) are as Si-H compounds according to the Formula (3) the compounds HSiCl 3 , HSiCl 2 Me, HSiClMe 2 , HSiCl 2 Et and HSiClEt 2 , HSi (OMe) 3 , HSi (OEt) 3 , HSi (OMe) 2 Me, HSi (OEt) 2 Me, HSi (OMe) Me 2 and HSi (OEt) Me 2 used.
  • alkenes used are propene, allyl chloride, acetylene, ethylene, isobutylene, cyclopentene, cyclohexene and 1-hexadecene.
  • HSiCl 3 and HSiMeCl 2 are used as Si-H compound and allyl chloride as alkene component.
  • Platinum, iridium or rhodium used.
  • [Y] - an anion is selected from the group comprising [tetrakis (3, 5-bis (trifluoromethyl) phenyl) borate], ([BARF]), tetraphenylborate ([BF 4 ] “ ), hexafluorophosphate ([PF 6 ] “ ), trispentafluoroethyltrifluorophosphate ([P (C 2 F 5 ) 3 F 3 ] " ), hexafluoroantimonate ([SbF 6 ] " ), hexafluoroarsenate ([AsF 6 ] “ ), fluorosulfonate, [R '-COO] “ , [R'-SO 3] ", [R'-O-SO 3]” [R '2 PO 4] “, or [(R' SO 2) 2 N] -, where R 'is a linear or branched aliphatic or alicyclic alkyl containing 1 to 12 carbon atoms
  • radicals R 1'7 each independently represent organic radicals having 1-20 C atoms.
  • the radicals R 1'7 are preferably aliphatic, cycloaliphatic, aromatic, araliphatic or oligoether groups.
  • Aliphatic groups are straight-chain or branched hydrocarbon radicals having from one to twenty carbon atoms, it being possible for heteroatoms, such as, for example, oxygen, nitrogen or sulfur atoms, to be present in the chain.
  • the radicals R 1'7 may be saturated or have one or more double or triple bonds which may be conjugated or isolated in the chain.
  • Hydrocarbon groups having one to 14 carbon atoms for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl or n-decyl.
  • cycloaliphatic groups are cyclic hydrocarbon radicals having between three and twenty carbon atoms, which may contain ring heteroatoms, such as oxygen, nitrogen or sulfur atoms.
  • the cycloaliphatic groups may also be saturated or have one or more double or triple bonds which may be conjugated or isolated in the ring.
  • Aromatic groups carbocyclic-aromatic groups or heterocyclic-aromatic groups can have between six and twenty-two carbon atoms. Examples of suitable aromatic groups are phenyl, naphthyl or anthracyl.
  • Oligoether development are groups of the general formula (13)
  • R ⁇ represents an aliphatic, cycloaliphatic, aromatic or araliphatic group.
  • an ionic liquid is used whose cations [A] + can not be formed by deprotonation or oxidative addition of a C-H bond to a low-valence metal complex, metal complexes with N-heterocyclic carbene ligands.
  • Particularly preferred cations of the ionic liquid used are N-alkylpyridinium and 1, 2, 3-trialkylimidazolium cations.
  • the inventive method is carried out as a two-phase reaction, wherein the catalyst can be used as a liquid phase and the reaction products as a liquid or gas phase.
  • Transition metal complex dissolved in the ionic liquid and contacted with a non-miscible phase in the reactor, which contains the reaction product at the reactor outlet, so that the ionic catalyst solution is separated by phase separation in the process continuously and recycled to the reactor.
  • a further variant of the method consists in a Maschinenfabung such that a film of the ionic
  • Catalyst solution is applied to a carrier material and the catalyst is brought into contact in this form in a gas phase reaction or in a Flussigphasenresure with the reaction mixture.
  • This transfer of the known for other reactions SILP technology on the hydrosilylation of non-polymeric Si-H compounds according to formula (1) with alkenes according to formula (2) was surprisingly very successful, since this process variant, the first successful application of Pt-containing SILP Represents catalysts. It is further Surprisingly, despite the known sensitivity to water of the hydrosilylation reaction, the reaction with supported ionic catalyst solutions succeeds. The lack of deactivation of the sensitive transition metal catalyst or the possible deterioration of the product selectivity by interactions of the support with the catalyst could not be easily foreseen.
  • the described method can be carried out both without pressure and under pressure.
  • we carried out the process at a pressure of up to 200 bar, more preferably at a pressure of up to 20 bar.
  • Example 1 Pressure-free Hydrosilylation Experiment with Ionic Liquid Using the Example of the Synthesis of 3-Chloropropyltrichlorosilane (Inventive)
  • a three-necked flask (100-250 ml) is provided with dropping funnel and contact thermometer for internal temperature control and dried under high vacuum. Subsequently, 6.0 g of the product 3-chloropropyltrichlorosilane are placed under a protective gas atmosphere in the three-necked flask.
  • 80 0 C external temperature control
  • about 8.5 mg equivalent to 600 ppmn Pt
  • the organic catalyst complex solution of PtC14 in 1-dodecene
  • stirring magnetic stirrer
  • All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after the addition. It is particularly important to pay attention to the correct ratio of the reactants.
  • the reaction temperature of 100 ° C is set and controlled on the thermostat.
  • the temperature of the intensive cooler (-20 0 C) is replaced by a
  • Table 1 shows the results of Example 1 and Comparative Example 1.
  • Example 2 Hydrosilylation experiment with ionic liquid under pressure (according to the invention)
  • ionic liquid 1-ethyl-2,3-dimethylimidazoliumbistrifluoromethanesulphonylimide are initially introduced into a laboratory autoclave which has been dried under high vacuum and flooded with argon.
  • 3.5 mg of platinum tetrachloride (equivalent to 300 ppmn) are weighed into the approximately moisture-free ionic liquid.
  • the ionic catalyst solution is after the addition of the catalyst for one hour under vacuum at 100 0 C (internal temperature control) dried. Thereafter, the remaining reactants (3-
  • the reactor is placed under argon under the reaction pressure of 12 bar.
  • the reaction temperature of 100 ° C is set on the heating jacket and controlled internally. When the reaction temperature has been reached, the reactants are added from the dropping funnel.
  • the autoclave After the end of the reaction (about 2 hours), the autoclave is carefully cooled in an ice bath to room temperature and then opened under argon flow. The contents are added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate containers. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired. The organic phase is analyzed by gas chromatography. The amount of bled in the product phase platinum is determined by ICP-AES.
  • All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after the addition. It is particularly important to pay attention to the correct ratio of the reactants.
  • the reactor is pressurized with argon under the system pressure of 12 bar.
  • the reaction temperature 100 ° C. is set on the heating jacket and controlled internally. When the reaction temperature has been reached, the reactants are added from the dropping funnel. After the end of the reaction (about 2 hours), the autoclave is carefully cooled in an ice bath to room temperature and then opened under argon flow.
  • organic phase (top) and ionic catalyst solution are separated and filled into separate containers. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
  • the organic phase is analyzed by gas chromatography.
  • Table 2 shows the results of Example 2 and Comparative Example 2.
  • the three-necked flask is connected to the reflux condenser under constant protective gas flow and provided with a dropping funnel.
  • the third port of the piston is closed with a contact thermometer for internal temperature control. If the apparatus is gas-tight, all newly connected system parts are dried in the HV. Thereafter, the remaining reactants (3-chloropropyltrichlorosilane: 5.6 g; allyl chloride 5, 6 g and
  • Trichlorosilane 12.5 g
  • All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after addition into the dropping funnel.
  • the reaction temperature of 100 0 C is set and controlled at the thermostat.
  • the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
  • the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the reaction temperature has returned to the set point. When the addition is completed, stirring is continued for 60 minutes to ensure complete conversion of the reactants.
  • ionic liquid and products are cooled in an ice bath.
  • the content of the three-necked flask is added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate vessels. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
  • the organic phase is analyzed by gas chromatography. The amount of in the Product phase of bled platinum is determined by ICP-AES.
  • the carrier material used is a silica granulate (about 5 g) with a particle size distribution of 0.2 to 0.5 mm.
  • the support Before the ionic liquid is applied, the support is calcined for several hours at 450 ° C. and placed under protective gas while still hot.
  • the ionic liquid 1-ethyl-3-methylimidazoliumbistrifluoromethanesulfonylimide (1.0 g) is already charged with the catalyst (PtCl 4 : 0.7 mg, corresponding to 55 ppmn) and is dissolved in a 10-fold excess of methanol.
  • the carrier material is combined with the IL-methanol solution and stirred until a homogeneous distribution can be ensured.
  • the methanol is carefully removed under vacuum and moderately elevated temperature (about 50 0 C).
  • This SILP catalyst is then dried under constant stirring (magnetic stirrer) at 80 0 C (external temperature control) under HV for one hour.
  • a 3-necked flask (100-250 ml) is equipped with dropping funnel, reflux condenser and contact thermometer for internal temperature control. Between Ruckpoundkuhler and three-necked flask here is a heated glass frit used to keep the catalyst. The entire apparatus is dried under high vacuum, including the SILP catalyst. If the apparatus is cooled, the dropping funnel is under constant inert gas stream with 6.3 g of allyl chloride and 11.7 g
  • Trichlorosilane is filled. All reactants (allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after addition into the dropping funnel. It In this case, pay particular attention to the correct ratio of the reactants.
  • the reaction temperature of 100 0 C is adjusted and regulated via the heating line of the glass frit.
  • the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
  • the three-necked flask serves as an evaporator of the educts and is heated with an oil bath at 100 0 C. When the reaction temperature is reached, the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the
  • Reaction temperature has returned to the set point.
  • the organic products are analyzed by gas chromatography. Residues of organic material adhering to the SILP can be separated off by means of vacuum or dry cyclohexane. The amount of bled in the product phase platinum is determined by ICP-AES.
  • ionic liquid 1-ethyl-3-methylimidazolium bistrifluoromethanesulfonylimide 10 ml of the ionic liquid 1-ethyl-3-methylimidazolium bistrifluoromethanesulfonylimide are introduced into a heated flask (100-250 ml). This is predried with constant stirring (magnetic stirrer) at 80 0 C (external temperature control) in the HV for one hour. When the ionic liquid is approximately moisture-free, 0.7 mg platinum tetrachloride (equivalent to 55 ppmn) is weighed. The ionic catalyst solution is added after the addition of
  • the reaction temperature of 100 0 C is set and controlled at the thermostat.
  • the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
  • the reaction temperature is reached, the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the reaction temperature has returned to the set point.
  • stirring is continued for 60 minutes to ensure complete conversion of the reactants. Thereafter, ionic liquid and products are cooled in an ice bath.
  • the content of the three-necked flask is added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate vessels. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
  • the organic phase is analyzed by gas chromatography.
  • the amount of bled in the product phase platinum is determined by ICP-AES.
  • the ionic liquid is introduced again without work-up into the apparatus and used again in the manner already described (preparation and amount of the reactants used) in the reaction. It is important to pay attention to sufficient protective gas technology. A drying of the ionic liquid in a vacuum can be omitted here. Such recycling can be successfully carried out for at least four steps.
  • Table 4 shows the results after the respective recycling. It can be seen that the reuse of the ionic catalyst solution leads to good results even after the third recycle.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
EP07765548A 2006-06-27 2007-06-21 Verfahren zur herstellung von siliciumorganischen verbindungen durch hydrosilylierung in ionischen flüssigkeiten Withdrawn EP2049553A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006029430A DE102006029430A1 (de) 2006-06-27 2006-06-27 Verfahren zur Herstellung von siliciumorganischen Verbindungen durch Hydrosilylierung in ionischen Flüssigkeiten
PCT/EP2007/056210 WO2008000689A1 (de) 2006-06-27 2007-06-21 Verfahren zur herstellung von siliciumorganischen verbindungen durch hydrosilylierung in ionischen flüssigkeiten

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US (1) US20100267979A1 (zh)
EP (1) EP2049553A1 (zh)
JP (1) JP2009541420A (zh)
CN (1) CN101472932A (zh)
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WO (1) WO2008000689A1 (zh)

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TWI457398B (zh) * 2007-12-27 2014-10-21 Momentive Performance Mat Jp Thermosetting Silicone Oxygenated Compounds
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CN101671356B (zh) * 2009-07-23 2011-12-28 杭州师范大学 一种室温离子液体/超临界co2介质中铑络合物催化烯烃的硅氢加成反应
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WO2015147920A1 (en) * 2014-03-25 2015-10-01 Dow Corning Corporation Method of separating volatile siloxane from feed mixture
CN106795289B (zh) * 2014-06-11 2020-05-05 美国陶氏有机硅公司 使用膜接触器以使气体和液体反应而形成有机硅产物的方法
CN106633772B (zh) * 2016-12-24 2018-07-13 衢州普信新材料有限公司 一种用于聚碳酸酯的有机硅阻燃剂的制备方法
CN109384233B (zh) * 2018-12-13 2023-10-20 江苏中能硅业科技发展有限公司 一种用于处理硅聚合物的方法

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CN101472932A (zh) 2009-07-01
US20100267979A1 (en) 2010-10-21
JP2009541420A (ja) 2009-11-26

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