WO2010016416A1 - Catalyseur pour une réaction d'hydrosilylation et procédé de production d'un composé organique du silicium utilisant le catalyseur - Google Patents

Catalyseur pour une réaction d'hydrosilylation et procédé de production d'un composé organique du silicium utilisant le catalyseur Download PDF

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WO2010016416A1
WO2010016416A1 PCT/JP2009/063498 JP2009063498W WO2010016416A1 WO 2010016416 A1 WO2010016416 A1 WO 2010016416A1 JP 2009063498 W JP2009063498 W JP 2009063498W WO 2010016416 A1 WO2010016416 A1 WO 2010016416A1
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group
compound
catalyst
iron
bond
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PCT/JP2009/063498
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Japanese (ja)
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浩 中沢
真澄 板崎
賢治 田中
明成 板垣
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公立大学法人大阪市立大学
信越化学工業株式会社
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Priority to JP2010523834A priority Critical patent/JP5572798B2/ja
Publication of WO2010016416A1 publication Critical patent/WO2010016416A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron

Definitions

  • the present invention relates to a novel catalyst for hydrosilylation reaction and a method for producing an organosilicon compound using the same.
  • Si—C bonds are used for functional compounds, but especially compounds having Si—C bonds are often used. Examples include silane coupling agents, rubber, release paper, adhesives, mold taking agents, LIMS molding agents and the like.
  • Si—C bond formation includes a method using an organometallic compound such as magnesium and lithium, and a hydrosilylation reaction between a silicon hydride compound and an unsaturated compound.
  • the former method has a wide range of synthesis and is suitable for the synthesis of special compounds, but has a complicated process and is not suitable for industrial mass production.
  • hydrosilylation reactions are used for industrial mass production because they have few by-products and are easy to react.
  • Examples of the hydrosilylation catalyst include transition metals such as platinum, palladium, rhodium, and ruthenium.
  • platinum is generally used because of its yield and ease of operation (Non-Patent Documents 1 to 3).
  • Non-Patent Documents 1 to 3 Non-Patent Documents 1 to 3).
  • the rise in metal prices due to the increase in demand for rare metals has been remarkable.
  • platinum has a high rate of price increase because it has many uses.
  • 92% of platinum produced worldwide is limited to South Africa and the Russian Federation. Therefore, there is great concern about stable supply.
  • the present invention has been made in view of the above circumstances, and a novel hydrosilyl capable of reacting a ⁇ Si—H group and a carbon-carbon multiple bond group to form a ⁇ Si—C bond using an iron compound catalyst. It is an object of the present invention to provide a catalyst for an oxidation reaction and a method for producing an organosilicon compound using the catalyst.
  • the present inventors have found that when a platinum catalyst is used when an ⁇ Si—H group is reacted with a carbon-carbon multiple bond group using an iron complex compound as a catalyst. It was found that ⁇ Si—C bonds can be formed in the same manner as described above, and the present invention has been made.
  • Claim 1 A catalyst for hydrosilylation reaction comprising an iron complex compound represented by the following general formula (1).
  • R 1 is a hydrogen atom, an unsubstituted or substituted alkyl or aryl group having 1 to 10 carbon atoms, or a ligand that affects the oxidation number of an iron atom formed from a SiR 3 group;
  • s is 0 ⁇ s ⁇ 3
  • R represents a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms or alkoxy group, a halogen atom, or a siloxane residue.
  • X is a ligand that affects the oxidation number of the iron atom, and is an unsubstituted or substituted cyclic compound having a C 4-10 aliphatic unsaturated group, trispirazolyl borate, tetrafluoroborate, hexafluorophosphate , And porphine and phthalocyanine.
  • t is 0 ⁇ t ⁇ 2.
  • Y is a ligand that does not affect the oxidation number of iron atoms formed from ammonia molecules, carbonyl molecules, oxygen atoms, oxygen molecules, amine molecules, phosphine molecules, or phosphite molecules, and u is 0 ⁇ u ⁇ 12.
  • Claim 2 The hydrosilylation catalyst comprising an iron complex compound according to claim 1, wherein the iron complex compound is a compound represented by the following general formula (2).
  • Claim 3 The catalyst for hydrosilylation reaction comprising the iron complex compound according to claim 2, wherein the iron complex compound is a compound represented by the following general formula (3).
  • Claim 4 A silicon compound having a ⁇ Si-H group and an organic compound having a carbon-carbon multiple bond group as raw materials, and in the presence of a hydrosilylation reaction catalyst comprising an iron complex compound according to any one of claims 1 to 3, A method for producing an organic compound having an Si-C bond, wherein an organic compound having an Si-C bond is obtained by a hydrosilylation reaction in the presence or absence of an organic solvent.
  • Claim 5 5.
  • Claim 6 6.
  • an ⁇ Si—H group and a carbon-carbon multiple bond group are reacted using the iron complex compound of the formula (1) of the present invention, an ⁇ Si—C bond can be formed in the same manner as when a platinum catalyst is used. Is possible. According to the present invention, a useful siloxane or silane compound can be produced in a high yield, and a compound having a ⁇ Si—C bond useful as a functional compound material can be produced at a low cost.
  • the novel catalyst for hydrosilylation reaction of the present invention is a compound represented by the following general formula (1), particularly a II-valent or IV-valent complex.
  • R 1 is independently a hydrogen atom, an alkyl group such as a methyl group, an ethyl group or a propyl group, an aryl group such as a phenyl group or a pyridyl group, or a part of hydrogen atoms bonded to a carbon atom of these groups ( 1 or 2 or more) or all of them are selected from a hydroxypropyl group, a cyanoethyl group, a 1-chloropropyl group, a 3,3,3-trifluoropropyl group, etc. substituted with a hydroxy group, a cyano group, a halogen atom, etc.
  • R independently represents a hydrogen atom, an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms or an alkoxy group, a halogen atom, or a siloxane residue.
  • examples of the unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms, the alkoxy group, and the halogen atom include those similar to R 6 in the formula (5) described later.
  • Examples of the siloxane residue include a group in which one hydrogen atom bonded to a silicon atom is eliminated in formula (4) described later.
  • X is cyclopentadiene, cyclohexadiene, cyclooctatetraene or a part (one or two or more) or all of hydrogen atoms bonded to carbon atoms of these groups by hydroxy group, cyano group, halogen atom, etc.
  • a ligand formed from an anion, porphine, or phthalocyanine that forms a salt such as a cyclic product, trispyrazolyl borate, tetrafluoroborate, hexafluorophosphate.
  • cyclopentadienyl anion is preferable.
  • Y affects the oxidation number of iron atoms selected from ammonia molecules, carbonyl molecules, oxygen atoms, oxygen molecules, amine molecules, phosphine molecules such as triphenylphosphine, phosphite molecules such as triethyl phosphite and triphenyl phosphite. It is a ligand that does not give.
  • s, t, and u are 0 ⁇ s ⁇ 3, 0 ⁇ t ⁇ 2, and 0 ⁇ u ⁇ 12.
  • s is greater than 0 and t and u are 0 or more, but s, t and u are numbers that make the entire metal salt neutral, and s and t are divalent or 4 oxidation numbers of iron atoms. It is a number that gives a value.
  • R 1 is a hydrogen atom, or a methyl group, an ethyl group, a phenyl group, an alkyl group or an aryl group having 1 to 8 carbon atoms such as a pyridyl group
  • X is denoted by C 5 R 2 5
  • R 2 is hydrogen
  • Y is a carbonyl molecule or a phosphine molecule such as triphenylphosphine.
  • (A) is a catalyst precursor, and the actual catalytically active species is considered to be (B). It is considered that (B) is formed by reacting (A) with the starting complex and hydrosilane, and olefin and hydrosilane are sequentially reacted with this to cause a hydrosilylation reaction.
  • (B) is formed by reacting (A) with, for example, 2 equivalents of hydrosilane, a complex (C) is formed, and when this complex is heated in solution, the silyl group and hydride are reductively eliminated from the iron to yield (B). Therefore, (C) is also a catalyst precursor for the hydrosilylation reaction of olefin, and complex (C) is an IV valent iron complex.
  • an organic compound having a Si—C bond by a hydrosilylation reaction according to the present invention, a silicon compound having an ⁇ Si—H group, an organic compound having a carbon-carbon multiple bond group, a general formula as a catalyst for a hydrosilylation reaction
  • an organic compound having a Si—C bond can be produced.
  • Each component for producing an organic compound having a Si—C bond more suitably by a hydrosilylation reaction is described below.
  • silicon compounds having ⁇ Si—H groups include the following components (A) and (B).
  • Component (A) is an organohydrogenpolysiloxane represented by the following general formula (4).
  • R 4 is independently a hydrogen atom or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms and does not have an aliphatic unsaturated bond, such as an alkyl group such as a methyl group, an ethyl group, or a propyl group. Groups, aryl groups such as phenyl groups, aralkyl groups such as benzyl groups and phenylethyl groups, and halogen-substituted alkyl groups such as 3,3,3-trifluoropropyl groups.
  • R 5 is independently an unsubstituted or substituted monovalent hydrocarbon group having 1 to 10 carbon atoms and having no aliphatic unsaturated bond.
  • Examples of the monovalent hydrocarbon group include a methyl group, an ethyl group, and a propyl group. And an alkyl group such as a phenyl group, an aryl group such as a phenyl group, an aralkyl group such as a benzyl group and a phenylethyl group, and a halogen-substituted alkyl group such as a 3,3,3-trifluoropropyl group.
  • g, h, i, and j are 0 or a positive number, but any one of g, h, and i must be a positive number, and g + h + i + j ⁇ 2 and at least one Si—H group in one molecule. It is what you have. More preferably, 2 ⁇ g + h + i + j ⁇ 1,000, still more preferably 2 ⁇ g + h + i + j ⁇ 100, and the number of Si is preferably 2 to 1,000, particularly 2 to 100.
  • the Si—H number is preferably 1 or more, particularly 2 to 100.
  • the amount of hydrogen polysiloxane blended is such that the number of moles of hydrogen atoms bonded to silicon atoms is 0.3 to 10 times the mole of the total number of alkenyl groups of the compound having a carbon-carbon multiple bond. It is sufficient if it is a mass part corresponding to 0.5 to 5 moles. If the blending amount is less than 0.3 times mole, it is not practical because the remaining amount of the organic compound having a carbon-carbon multiple bond group, which is the other reaction raw material of the hydrosilylation reaction, increases, and it exceeds 10 times mole. Even if used, the yield of the hydrosilylation reaction is not improved.
  • Component (B) is a silane compound having an ⁇ Si—H group represented by the following composition formula (5).
  • R 6 is independently a hydrogen atom, An alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group; a cycloalkyl group such as a cyclohexyl group; an aryl group such as a phenyl group or a biphenyl group; or one of hydrogen atoms bonded to a carbon atom of these groups. 1 to 10 carbon atoms of unsubstituted or substituted selected from trifluoromethyl group, hydroxypropyl group, cyanoethyl group, etc., wherein part (one or two or more) or all are substituted with hydroxy group, cyano group, halogen atom, etc.
  • the amount of the silane compound used is such that the number of moles of hydrogen atoms bonded to the silicon atom is 0.3 parts by weight corresponding to the total number of alkenyl groups of the compound having a carbon-carbon multiple bond.
  • the mass part may correspond to 0.5 to 5 times mol. If the blending amount is less than 0.3 times mol, the remaining amount of the organic compound having a carbon-carbon multiple bond group, which is another reaction raw material of the hydrosilylation reaction, is not practical, and more than 10 times mol. Even if used, the yield of the hydrosilylation reaction is not improved.
  • an organic compound represented by the following composition formula (6) can be exemplified as the component (C).
  • R 7 is independently a hydrogen atom, Alkyl groups such as methyl group, ethyl group, propyl group, butyl group, cycloalkyl groups such as cyclopentyl group, cyclohexyl group, aryl groups such as phenyl group, naphthyl group, biphenyl group, vinyl group, allyl group, butenyl group, etc. Alkenyl groups, or trifluoromethyl groups, hydroxypropyl groups, cyanoethyl groups, in which part or all of the hydrogen atoms bonded to the carbon atoms of these groups are substituted with hydroxy groups, cyano groups, epoxy groups, halogen atoms, etc.
  • Alkyl groups such as methyl group, ethyl group, propyl group, butyl group
  • cycloalkyl groups such as cyclopentyl group, cyclohexyl group
  • aryl groups such as phenyl group, naphthy
  • An unsubstituted or substituted alkoxycarbonyl group having 1 to 10 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, or a propoxycarbonyl group;
  • Halogen atoms such as acrylic group, fluorine, chlorine, bromine, iodine, Examples include polyether-containing groups.
  • an acetylene structure in which R 7 groups on different carbon atoms at the 1 and 2 positions are small, or R 7 may be bonded to each other to form a cyclic structure.
  • cyclopentene, cyclohexene, norbornene, Norbornadiene, bicyclo [2,2,2] octene, indene and the like, and a part (one or two or more) or all of hydrogen atoms bonded to carbon atoms of these cyclic structures are further methyl group, ethyl group Alkyl groups such as propyl group, cycloalkyl groups such as cyclopentyl group and cyclohexyl group, aryl groups such as phenyl group, naphthyl group and biphenyl group, alkenyl groups such as vinyl group, allyl group and butenyl group, or Some or all of the hydrogen atoms bonded to the carbon atom are replaced with hydroxy groups, cyano groups, epoxy groups
  • Those substituted with 10 alkoxycarbonyl groups, and those further substituted with acrylic groups, halogen atoms such as fluorine, chlorine, bromine and iodine, polyether-containing groups and the like are also included.
  • an alkenyl group, an alkyl group, an aryl group, and an alkoxy group are preferable, and an alkenyl group, an alkyl group, and an alkoxy group are more preferable.
  • the substitution pattern of the carbon-carbon multiple bond is preferably disubstituted, monosubstituted, more preferably monosubstituted olefin.
  • Component (D) is a novel catalyst for hydrosilylation reaction, and is an iron complex represented by the above general formula (1).
  • the above iron catalyst can be suitably used in an amount of 0.0001 to 10-fold mol, preferably 0.001 to 1-fold mol based on the total number of alkenyl groups in component (C).
  • an organic solvent can be optionally used for the production of an organic compound having a Si—C bond.
  • the organic solvent is an organic solvent that does not participate in the hydrosilylation reaction, preferably a hydrocarbon type, more preferably heptane, octane, or toluene.
  • the production of the organic compound having an Si—C bond by the hydrosilylation reaction is 20 to 150 ° C., preferably 50 to 120 ° C. as the reaction temperature.
  • Example 1 The Schlenk tube was placed under a nitrogen atmosphere, C 5 H 5 Fe (CO) 2 CH 3 [dicarbonylcyclopentadienylmethyliron] 23 mg (0.119 mmol), 1-hexene 1.47 mL (11.88 mmol), pentamethyl 1 mL of toluene was added to 0.584 mL (2.97 mmol) of disiloxane, and the mixture was stirred at 80 ° C. for 48 hours. After cooling, the reaction mixture was concentrated under reduced pressure.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solvent: hexane), and 244 mg of the product 2,2,4,4-tetramethyl-3-oxa-2,4-disiladecane (7) was obtained. (1.04 mmol) was obtained.
  • Example 2 The Schlenk tube was placed under a nitrogen atmosphere, 20.7 mg (0.107 mmol) of C 5 H 5 Fe (CO) 2 CH 3 [dicarbonylcyclopentadienylmethyliron], 1.67 mL (10.67 mmol) of 1-octene, 1 mL of toluene was added to 0.524 mL (2.67 mmol) of pentamethyldisiloxane, and the mixture was stirred at 80 ° C. for 48 hours. After cooling, the reaction mixture was concentrated under reduced pressure.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solvent: hexane) to obtain 621 mg of the product 2,2,4,4-tetramethyl-3-oxa-2,4-disiladodecane (8). (2.66 mmol) was obtained.
  • Example 3 The Schlenk tube was placed under a nitrogen atmosphere, 21.1 mg (0.109 mmol) of C 5 H 5 Fe (CO) 2 CH 3 [dicarbonylcyclopentadienylmethyliron], 0.311 mL (2.72 mmol) of styrene, pentamethyl 1 mL of toluene was added to 0.533 mL (2.71 mmol) of disiloxane, and the mixture was stirred at 80 ° C. for 48 hours. After cooling, the reaction mixture was concentrated under reduced pressure.
  • the obtained residue was purified by column chromatography (filler: silica gel, developing solvent: hexane), and the product 2,2,4,4-tetramethyl-6-phenyl-3-oxa-2,4-disilahexane ( 9) and 2,2,4,4-tetramethyl-6-phenyl-3-oxa-2,4-disilahex-5-ene (10) 308 mg were obtained.

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Abstract

L'invention porte sur un catalyseur pour une réaction d'hydrosilylation, qui comprend un composé complexe du fer représenté par la formule générale (1) : Xt-Fe-R1 s(Yu) (1) [dans laquelle R1 représente H, un groupe alkyle, un groupe aryle ou un ligand qui est formé par un groupe SiR3 et peut avoir une influence sur le nombre d'oxydation de l'atome de fer; s représente un nombre de plus de 0 et de pas plus de 3 (à savoir 0 < s ≤ 3); R représente H, un groupe alcoxy, un atome d'halogène ou un reste siloxane; X représente un ligand qui peut avoir une influence sur le nombre d'oxydation de l'atome de fer et est choisi parmi une structure cyclique ayant un groupe en C4-10 insaturé aliphatique, un trispyrazolylborate, un tétrafluoroborate, un hexafluorophosphate, une porphine et une phtalocyanine; t représente un nombre de pas moins de 0 et de moins de 2 (à savoir 0 ≤ t < 2); Y représente un ligand formé par une molécule d'ammoniac, une molécule carbonylée, un atome d'oxygène, une molécule d'oxygène, une molécule d'amine, une molécule de phosphine ou une molécule de phosphite et n'influence pas le nombre d'oxydation de l'atome de fer; et u représente un nombre de 0 à 12 inclus (à savoir 0 ≤ u ≤ 12); à la condition que s représente un nombre de plus de 0, t et u représentent indépendamment un nombre de 0 ou plus, s, t et u représentent indépendamment un nombre tel qu'un sel métallique devienne neutre dans son ensemble, et s et t représentent indépendamment un nombre tel que le nombre d'oxydation de l'atome de fer devienne 2 ou 4].
PCT/JP2009/063498 2008-08-05 2009-07-29 Catalyseur pour une réaction d'hydrosilylation et procédé de production d'un composé organique du silicium utilisant le catalyseur WO2010016416A1 (fr)

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Cited By (10)

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US8415443B2 (en) 2009-07-10 2013-04-09 Momentive Performance Materials Inc. Hydrosilylation catalysts
WO2013081794A1 (fr) * 2011-12-01 2013-06-06 Dow Corning Corporation Catalyseurs de réaction d'hydrosilylation et compositions durcissables et procédés pour leur préparation et utilisation
KR20170042319A (ko) 2014-08-12 2017-04-18 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 반응 촉매
KR20170042681A (ko) 2014-08-19 2017-04-19 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 철 촉매
KR20180030080A (ko) 2015-07-14 2018-03-21 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 반응 촉매
US10000515B2 (en) 2014-08-12 2018-06-19 Kyushu University, National University Corporation Hydrosilylation reaction catalyst
WO2018159595A1 (fr) 2017-02-28 2018-09-07 国立大学法人九州大学 Catalyseur pour réaction d'hydrosilylation, réaction d'hydrogénation, et réaction de réduction par hydrosilane
KR20180108656A (ko) 2016-01-22 2018-10-04 신에쓰 가가꾸 고교 가부시끼가이샤 신규 아이소사이아나이드 화합물 및 하이드로실릴화 반응 촉매
CN110234679A (zh) * 2016-12-23 2019-09-13 埃肯有机硅法国简易股份公司 可用作有机硅组合物的氢化硅烷化、脱氢甲硅烷基化和交联的催化剂的钴化合物
FR3126417A1 (fr) * 2021-08-31 2023-03-03 Elkem Silicones France Sas Procédé d’hydrosilylation catalysé par un complexe de fer

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BRUNNER, H. ET AL.: "Synthesis of (C5H5)Fe(CO) (SiHPh2)2H, a catalytically active intermediate in the hydrosilylation of acetophenone by diphenylsilane", J. ORGANOMET. CHEM., vol. 412, no. 1-2, 1991, pages C11 - C13 *

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8415443B2 (en) 2009-07-10 2013-04-09 Momentive Performance Materials Inc. Hydrosilylation catalysts
WO2013081794A1 (fr) * 2011-12-01 2013-06-06 Dow Corning Corporation Catalyseurs de réaction d'hydrosilylation et compositions durcissables et procédés pour leur préparation et utilisation
CN103958059A (zh) * 2011-12-01 2014-07-30 道康宁公司 硅氢加成反应催化剂和可固化组合物及它们的制备和使用方法
JP2015510494A (ja) * 2011-12-01 2015-04-09 ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ ヒドロシリル化反応触媒及び硬化性組成物並びにこれらの調製及び使用方法
US9073950B2 (en) 2011-12-01 2015-07-07 Dow Corning Corporation Hydrosilylation reaction catalysts and curable compositions and methods for their preparation and use
US10000515B2 (en) 2014-08-12 2018-06-19 Kyushu University, National University Corporation Hydrosilylation reaction catalyst
KR20170042319A (ko) 2014-08-12 2017-04-18 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 반응 촉매
US10005797B2 (en) 2014-08-12 2018-06-26 Kyushu University, National University Corporation Hydrosilylation reaction catalyst
US10239896B2 (en) 2014-08-19 2019-03-26 Kyushu University, National University Corporation Hydrosilylation iron catalyst
KR20170042681A (ko) 2014-08-19 2017-04-19 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 철 촉매
KR20180030080A (ko) 2015-07-14 2018-03-21 고쿠리쓰다이가쿠호진 규슈다이가쿠 하이드로실릴화 반응 촉매
KR20180108656A (ko) 2016-01-22 2018-10-04 신에쓰 가가꾸 고교 가부시끼가이샤 신규 아이소사이아나이드 화합물 및 하이드로실릴화 반응 촉매
US10829504B2 (en) 2016-01-22 2020-11-10 Shin-Etsu Chemical Co., Ltd. Isocyanide compound and hydrosilylation reaction catalyst
CN110234679A (zh) * 2016-12-23 2019-09-13 埃肯有机硅法国简易股份公司 可用作有机硅组合物的氢化硅烷化、脱氢甲硅烷基化和交联的催化剂的钴化合物
CN110234679B (zh) * 2016-12-23 2021-09-28 埃肯有机硅法国简易股份公司 可用作有机硅组合物的氢化硅烷化、脱氢甲硅烷基化和交联的催化剂的钴化合物
WO2018159595A1 (fr) 2017-02-28 2018-09-07 国立大学法人九州大学 Catalyseur pour réaction d'hydrosilylation, réaction d'hydrogénation, et réaction de réduction par hydrosilane
KR20190125374A (ko) 2017-02-28 2019-11-06 고쿠리쓰다이가쿠호진 규슈다이가쿠 히드로실릴화 반응, 수소화 반응 및 히드로실란 환원 반응용 촉매
FR3126417A1 (fr) * 2021-08-31 2023-03-03 Elkem Silicones France Sas Procédé d’hydrosilylation catalysé par un complexe de fer
WO2023031524A1 (fr) 2021-08-31 2023-03-09 Elkem Silicones France Sas Procede d'hydrosilylation catalyse par un complexe de fer

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