EP2134728A2 - Procede de traitement d'alcoxysilanes a l'aide d'un compose organometallique, en particulier pour preparer des organomonoalcoxy (ou monohydroxy)silanes - Google Patents

Procede de traitement d'alcoxysilanes a l'aide d'un compose organometallique, en particulier pour preparer des organomonoalcoxy (ou monohydroxy)silanes

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Publication number
EP2134728A2
EP2134728A2 EP08717421A EP08717421A EP2134728A2 EP 2134728 A2 EP2134728 A2 EP 2134728A2 EP 08717421 A EP08717421 A EP 08717421A EP 08717421 A EP08717421 A EP 08717421A EP 2134728 A2 EP2134728 A2 EP 2134728A2
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EP
European Patent Office
Prior art keywords
reaction
radical
metal
θebi
linear
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.)
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Application number
EP08717421A
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German (de)
English (en)
French (fr)
Inventor
Thierry Vidal
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.)
Rhodia Operations SAS
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Rhodia Operations SAS
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Filing date
Publication date
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Publication of EP2134728A2 publication Critical patent/EP2134728A2/fr
Withdrawn legal-status Critical Current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
    • C07F7/18—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 present invention relates to substitution treatments for alkoxy functions carried by alkoxysilanes, by groups other than alkoxy, for example alkyl groups (especially methyl) or functional groups such as haloalkyl groups (in particular propyl). These treatments are carried out using organometallic compounds, optionally halogenated.
  • Such substitutions are at the heart of certain methods for the synthesis of functionalized organomonoalkoxy (or monohydroxy) silanes, in particular halogenated or alkenylated, as well as the use of these organomonoalkoxy (or monohydroxy) silanes as synthesis intermediates in organic chemistry, for the production of organomonoalkoxy (or monohydroxy) silanes functionalized with groups other than halogens or alkenyls, for example by amino, thiol or polysulfur groups.
  • the invention is also directed to compositions containing such synthetic intermediates in organic chemistry.
  • the technical problem underlying the invention is related to the fact that the alkoxysilane rearrangement reaction by groups other than alkoxy generates troublesome by-products, ie optionally halogenated metal alkoxylates.
  • These co-products are troublesome because they can be aggressive or denaturing with respect to the substituted alkoxysilanes that one seeks to obtain.
  • they can be non-recoverable waste and difficult to manage on the environmental level.
  • the application WO-A-03/027125 describes, inter alia, a process for obtaining functionalized organomonoalkoxysilanes, in particular halogens, which can be used, in particular, as synthesis intermediates.
  • This process consists in reacting a halogenated organotrialkoxysilane with a halogenated organomagnesium compound, so as to obtain the target halogenated organomonoalkoxysilane and halogenated organomagnesium salts, according to the following reaction (Ra): (Ra)
  • R 1 is an ethyl group
  • B is a divalent residue of formula - (CH 2 ) 3 -
  • Me and Et respectively represent CH 3 - and
  • the dimethylethoxy-chloropropylsilane compound (I) is the intermediate compound of interest.
  • the reaction must therefore stop at this stage if we want to optimize the yield.
  • the magnesium ethoxides generated during the synthesis of organomonoalkoxysilanes by reaction of alkylmagnesian with alkoxysilanes are undesirable co-products.
  • These are basic salts which can degrade the silanes formed, in this case the dimethylethoxy-chloropropylsilane compound (I) targeted in the reactions Ra & Ra.1 described above.
  • One of the objectives of the present invention is to provide a new process for the substitution treatment of alkoxy functions of alkoxysilanes by groups other than alkoxides, using at least one organometallic compound, in which the problem of the presence of unwanted co-products of metal alkoxylate type would be solved.
  • Another object of the present invention is to provide an alternative to the synthesis of functionalized organomonoalkoxy (or monohydroxy) silanes, in particular halogen (for example dimethylethoxychloropropylsilane) or alkenyl (for example dimethylethoxyallylsilane) especially useful as synthesis intermediates in chemistry.
  • organic which may allow their improvement, for example with regard to the neutralization of troublesome co-products, yield, productivity, cost, environmental compatibility and / or the availability of reagents consumables used.
  • Another object of the invention is to provide a process for preparing functionalized organomonoalkoxy (or monohydroxy) silanes, in particular halogenated or alkenylated, capable of reacting with a nucleophilic agent to produce functionalized organomonoalkoxy (or monohydroxy) silanes, for example by amino, thiol or polysulfide groups.
  • Another object of the invention is also to propose the use of compounds obtained by this process as an intermediate for the synthesis of organomonoalkoxy (or monohydroxy) silanes functionalized, for example, with amino, thiol or polysulphide groups.
  • This method essentially consists in bringing the metal alkoxylate MOR into contact with at least one agent (A) capable of reacting the alkoxy OR functions of this alkoxylate MOR in order to generate one or more species inert with respect to the alkoxysilane, said agent (A) being selected from the group of electrophiles and / or mineral acids. It is the merit of the inventors to have found a simple, economical, elegant and efficient way of transforming co-products (ie metal alkoxylates, optionally halogenated) into chemical species, on the one hand, compatible with the targeted products, and, secondly, easily manageable in terms of treatment, or even recovery, waste.
  • co-products ie metal alkoxylates, optionally halogenated
  • the agent (A), which is electrophilic and / or acidic, is, for example: a derivative of the halo (in particular chloro) silane type in order to generate a halide (in particular a chloride) metal (in particular magnesium) and, incidentally, another alkoxysilane, an acyl halide (for example chloride), or a mineral acid such as HCl, H 2 SO 4 .
  • the halide (for example chloride) metal (for example magnesium) is an inert species, that is to say, more neutral lato sensu than an alkoxylate (for example ethoxide) and can thus allow the distillation of noble species without significant degradation.
  • this inert or neutral species namely for example the magnesium salt, can be solubilized directly in water and be discharged into aqueous waste since it contains no organic filler (absence of COD).
  • the alkoxysilane generated in the case where the agent (A) is a silane can be reengaged as a starting reagent in a subsequent operation of metal condensation (for example magnesium).
  • metal condensation for example magnesium
  • the process according to the invention makes it possible to improve the yields. It is thus possible to recover by distillation the organomonoalkoxysilane (I), efficiently, simply, economically, industrially, selectively and without effluent management problem, since the metal salts (which may be, for example, magnesium salts) ) generated are inorganic and can be solubilized in water.
  • the metal salts which may be, for example, magnesium salts
  • agent (A) is chosen from the group comprising the compounds of formula:
  • X1 1, 2 or 3;
  • the symbols X 1 identical to or different from each other, are identical or different from X and represent a halogen;
  • Z 1 which are identical or different, each represent a hydrocarbon radical, preferably a linear, branched or cyclic alkyl radical having from 1 to 8 carbon atoms; an aryl radical having 6 to 18 carbon atoms; an arylalkyl radical or an alkylaryl radical (C 6 aryl) C 18, C 1 -C 6 alkyl), Z 1 optionally carrying at least one halogen or perhalogenated group;
  • X 2 are identical or different from each other and correspond to the same definition as X 1 ;
  • Z 2 are identical or different from each other and correspond to the same definition as Z 1 ;
  • X 3 are identical or different from each other and correspond to the same definition as X 1 ;
  • Z 3 are identical to or different from each other and correspond to the same definition as Z 1 ;
  • X 4 are identical or different from each other and correspond to the same definition as X 1 ;
  • the symbols Z 4 are identical to or different from one another and correspond to the same definition as Z 1 ;
  • the symbols Z 5 are identical or different from each other and correspond to the same definition as Z 1 ; o and their mixtures.
  • X 1 , X 2 , X 3 , X 4 are each a halogen identical to that involved in the reaction between the alkoxysilane and the metal species M.
  • a preferred example of an electrophilic agent (Aa) is chloropropyltrichlorosilane.
  • a preferred example of an electrophilic agent is chloroacetate.
  • a preferred example of an electrophilic agent (A.c) is mesyl chloride.
  • a preferred example of an electrophilic agent (A.d) is diethylchlorophosphate.
  • the agent (A) is introduced into the reaction medium at least partly before and / or during and / or after, preferably after, the appearance of the co-product alkoxylate (X) x MOR in this reaction medium.
  • the metal M is selected from the group consisting of Mg, Na, Li, Ca, Ba, Cd, Zn, Cu, their mixtures and their alloys, with magnesium being preferred.
  • One of the key elements of the "dealkoxylation" treatment process according to the invention is the reaction between the metal alkoxylate (X) x MOR [hereinafter designated by reference (IV)] and the agent (A) , in particular electrophilic.
  • the reaction between the metal alkoxylate (X) x MOR [hereinafter designated by the reference (IV)] and the agent (Ab) is advantageously the next one :
  • agent (A) used result from the stoichiometry of the inactivation reaction of the alkoxylate (IV) (in particular reactions 1 and 2 referred to above). In practice, they are advantageously 1.2 ⁇ 0.5 times the molar stoichiometry and more preferably still 1 times the molar stoichiometry.
  • the operating conditions in which the inactivation of the alkoxylate takes place are advantageously 1.2 ⁇ 0.5 times the molar stoichiometry and more preferably still 1 times the molar stoichiometry.
  • (IV) of the alkoxylate (X) x MOR co-product with the agent (A) are, for example, a reaction temperature of between 0 and 200 ° C. and a pressure equal to atmospheric pressure.
  • the treatment method according to the invention has a particularly advantageous application for the preparation of functionalized organoalkoxy (or hydroxy) silanes, especially functionalized organomonoalkoxy (or monohydroxy) silanes, in particular halogenated or alkenylated silanes.
  • these functionalized organomonoalkoxy (or monohydroxy) silanes may satisfy the following formula (I):
  • R 1 represents hydrogen or a monovalent hydrocarbon group corresponding to R, R 1 being in the latter case chosen from alkyl radicals, linear, branched or cyclic, having from 1 to 25, preferably 1 to 8 carbon atoms, carbon and linear, branched or cyclic alkoxyalkyl radicals having from 2 to
  • R 2 which are identical or different, are each a monovalent hydrocarbon group, different from an alkoxy, corresponding to R 'and each represents a linear, branched or cyclic alkyl radical having from 1 to 25, preferably 1 to 8 carbon atoms; an aryl radical having 6 to 18 carbon atoms; an arylalkyl radical or an alkylaryl radical (C 18 -C 18 aryl, C 1 -C 20 alkyl); R 2 optionally carrying at least one halogen or perhalogenated group;
  • Y represents either -BY 1 or Y 2 : with Y 1 corresponding to: II ) a halogen atom (symbol HaI), preferably chosen from chlorine, bromine and iodine atoms; ii.l) a group R 3 corresponding to a linear, branched or cyclic alkyl radical having 1 to 8 carbon atoms, an aryl radical having 6 to 18 carbon atoms, an arylalkyl radical or an alkylaryl radical; (C 1 -C 18 aryl, C 1 -C 0 alkyl), R optionally comprising at least one heteroatom and optionally carrying at least one halogen or perhalogenated group; iii.l) or an organic monovalent functional group W selected from the group consisting of linear or branched linear alkoxyl or acyl radicals having from 2 to 8 carbon atoms, the amino, mercapto, cyano, thiocyanato, oxycyanato, ( organos
  • R 4'1 alkenyl groups linear, branched or cyclic, having from 2 to 10 carbon atoms, tthhee ggrroouuppeess.
  • This preparation process is of the type consisting essentially of reacting at least one organometallic reagent which contains metal M and which is optionally generated in situ, with at least one organoalkoxysilane (II) chosen from di-, tri-, the tetraalkoxysilanes and mixtures thereof and of the type of those in which at least one of the co-products comprises at least one halogenated metal (IV) metal alkoxylate comprising metal M.
  • organometallic reagent which contains metal M and which is optionally generated in situ
  • this preparation process is characterized in that the alkoxy-functional alkoxysilane (s) of formula OR is an organoalkoxysilane (II) chosen from di-, tri-, tetraalkoxysilanes and mixtures thereof and is contacted with the organometallic compound (III) of formula R'M to generate the co-product (IV) comprising at least one metal alkoxylate of formula (X) x MOR.
  • organoalkoxysilane (II) chosen from di-, tri-, tetraalkoxysilanes and mixtures thereof and is contacted with the organometallic compound (III) of formula R'M to generate the co-product (IV) comprising at least one metal alkoxylate of formula (X) x MOR.
  • the preparation process is of the type consisting essentially of reacting at least one halogenated organoalkoxysilane (II) chosen from tri-, tetra-alkoxysilane and mixtures thereof, with at least one organometallic compound (III) of formula R 2 -M, in the presence of at least one solvent (Sl) having an initial boiling point ⁇ ebi (Sl) less than or equal to the boiling temperature ⁇ eb (I) of the organomonoalkoxysilane (I) and optionally at least one solvent (S2) having an initial boiling point ⁇ ebi (S2) greater than or equal to ⁇ ebi (I), ⁇ ebi (Sl) being less than or equal to ⁇ ebi (S2) , this compound organometallic (III) being capable of substituting the alkoxy radicals with organic radicals, in particular according to the following reaction scheme:
  • this process comprises the following steps:
  • addition / reaction comprising the steps (successive or not) following: -al- addition of a solution of the organometallic compound (III) in a solvent Sl, the compound (II);
  • V.1 which may be a metal salt (Va.l) with water; possible elimination of the solution obtained in dl;
  • phase -e- separation and collection of the organomonoalkoxysilane (I), preferably by distillation, and more preferably still, by distillation under reduced pressure; the product (VL1) of reactions 1 and 2 included in the distillation residue being optionally recycled in reaction 3; - Phase -f- possible hydrolysis step for converting organomonoalkoxysilane (I) organomonohydroxysilane (I); the phases -d- and -e- possibly being reversed.
  • a heavy solvent for example of water-immiscible hydrocarbon type
  • the halogeno-metallic (III) in which the metal salts (for example magnesium) formed are in powder form and can therefore be perfectly stirred (which makes it possible to envisage a distillation)
  • the organomonoalkoxysilane (I) is distilled, preferably under reduced pressure.
  • the -d- phase consists in solubilizing the salts formed once the organomonoalkoxysilane (I) has left the reaction medium. This makes it possible to avoid the hydrolysis of the organomonoalkoxysilane (I) and to recycle without treatment the heavy solvent S 2 in the process.
  • the preparation process according to the invention is of the type consisting essentially of reacting at least one non-halogenated organoalkoxysilane (II) chosen from tri-, tetraalkoxysilane and mixtures thereof, with at least one halogenated organic compound (III) (preferably an allyl halide), in the presence of at least one metal (M) and in the presence of at least one solvent (Sl) having a temperature of initial boiling ⁇ ebi (Sl) less than or equal to the boiling temperature ⁇ eb (I) of the organomonoalkoxysilane (I) and optionally at least one solvent (S2) having an initial boiling point ⁇ ebi (S2) upper or equal to ⁇ ebi (I), ⁇ ebi (Sl) being less than or equal to ⁇ ebi (S2), this halogenated organic compound (III) being capable of substituting the alkoxy radicals by organic radicals, according to the following reaction scheme (reaction II /
  • reaction between the halogenated metal alkoxylate comprising metal M (IV.2) and the agent (A.b), in particular electrophilic is as follows:
  • the method according to the second embodiment comprises the following steps: -a bringing the metal M and the solvent S1, or possibly a solvent S2; -b- Possible activation of the reaction, preferably by adding a catalytic amount of at least one halogen and / or an alkyl halide and / or by heating the reaction medium and / or the metal M;
  • the temperature of the reaction medium is preferably maintained at a temperature ⁇ r less than or equal to the boiling temperature ⁇ ebSl of the solvent S1;
  • organomonoalkoxysilanes (I) and (VI.2) preferably by distillation, and more preferably still, by distillation under reduced pressure;
  • (III) is introduced into the reaction medium in equivalent molar amount, or even a slight excess or slight defect, relative to the starting alkoxysilane (II).
  • lightly defect or excess is meant, for example, within the meaning of the invention, a margin of ⁇ 5 mol%.
  • the process according to the second embodiment of the invention can thus make it possible to recover the functionalized (preferably alkenyl) organomonoalkoxy (or monohydroxy) silane targeted selectively, efficiently, simply, directly, economically, industrially, without too much constraints on ecotoxicity (effluent treatment).
  • By-products such as metal salts (for example magnesium) are formed in smaller amounts than those observed in the known routes, in particular the Grignard route.
  • the process according to the invention is advantageously "eco-compatible".
  • This process consists, among other things, in slowly introducing the compound (III), for example the allyl halide, onto a base containing the organoalkoxysilane (II) silicone derivative and the metal (M), in particular magnesium, for example in the form of turns.
  • the compound (III) for example the allyl halide
  • the metal (M) in particular magnesium, for example in the form of turns.
  • the molar ratios of these reagents (III), (II) and metal (M), in particular magnesium, are stoichiometric. It is also possible to use an excess of metal (especially magnesium) to further limit the formation of bis-allyl.
  • the possible addition of S2 in the reaction medium, at the beginning of the process, for example with Sl, in particular during step -a-, and / or during the optional stage -el- is advantageously associated not only with a step -h- separation and collection of a functionalized organomonoalkoxy (or monohydroxy) silane (I), preferably by distillation and, more preferably still, by distillation under reduced pressure , but also with the step -i which intervenes, advantageously, after the step -h- and which consists in solubilizing the metal salts (for example magnesium) present in solid form (for example in suspension) in the reaction medium, this solubilization being preferably carried out by adding an aqueous acidic solution.
  • the metal salts for example magnesian
  • the solvent S1 is employed such that the SI / M molar ratio is between 3: 1 and 1: 1, preferably between 2.5: 1 and 1.5: 1, and more preferably still equal to about 2: 1.
  • the temperature of the reaction medium ⁇ r is generally preferable for the temperature of the reaction medium ⁇ r to be between approximately ( ⁇ ebSl - ( ⁇ ebS1 x 0.50)) and ⁇ ebS1, in particular between approximately ( ⁇ ebS1 - ( ⁇ ebS1 x 0.20)) and ⁇ ebS1.
  • the halogenated organic compound (III) is a haloalkenyl, preferably a halide (especially chloride or bromide) of allyl or methallyl, isopenyl, butenyl or cyclic hexenyl. or not, and more preferably still, an allyl chloride or bromide.
  • the step -h- separation and collection of the compound (I) is carried out discontinuously in at least one time, preferably by distillation under reduced pressure.
  • the boiling temperature " ⁇ eb" of a compound corresponds to its initial boiling point, according to the ASTM D 86-99 standard test.
  • the radical Z 2 of the agent (Ab) is chosen such that the product (Vb) of the reaction 2 has an initial boiling temperature ⁇ ebi (Vb), which has a deviation of at least ⁇ ebi (S2) and / or ⁇ ebi (I) from at least 5 0 C, preferably at least 10 0 C, more preferably at least 30 0 C, and still more preferably at least 40 0 C.
  • Sl is chosen from the group of ethereal organic compounds and / or from the group of acetals, and in particular from the subgroup comprising tetrahydrofuran (THF), methyl-THF (Me-THF), dialkyl ethers (preferably dibutyl ether), dioxanes and mixtures thereof.
  • THF tetrahydrofuran
  • Me-THF methyl-THF
  • dialkyl ethers preferably dibutyl ether
  • S 2 is selected from the group of compounds having an initial boiling point ⁇ ebi, defined as follows: 150 ° C. ⁇ ebi, preferably 180 ° C. ⁇ ebi, and still more preferably 190 ° C. ⁇ ebi ⁇ 350 ° C.
  • S 2 is generally chosen from the group of compounds comprising silanes (in particular alkoxysilanes), hydrocarbons, hydrocarbon cuts, (poly) aromatic compounds (especially alkylbenzenes), alkanes (in particular heavy), and (poly) ) ethers, phosphorus compounds, sulfolanes (especially dialkylsulfones), ionic liquids, dialkylnitriles and mixtures thereof.
  • solvent S2 By way of examples of commercial products that may be used as solvent S2, mention may be made of petroleum cuts or hydrocarbon cuts, in particular those sold under the name ISOP AR® M, N or P, by the company Exxon Mobil Chemical.
  • the amount of solvent S 2 in the reaction medium may be between 50 and 300 g for 300 g of reaction medium, before the step -a4- elimination of Sl, preferably by distillation.
  • the amount of solvent S1 and / or S2 is generally set so that the reaction medium can be stirred.
  • the incorporation of S2 into the reaction medium is preferably carried out when the organic compound (II) is consumed at least 70% by weight, preferably at least 90% by weight. weight, by the reaction of (II) with (III).
  • radicals R 1 are chosen from the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, CH 3 OCH 2 -, CH 3 OCH 2 CH 2 - and CH 3 OCH (CH 3 ) CH 2 -,
  • radicals R 2 are chosen from the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl and phenyl,
  • the radical Y 2 represents: the symbol R ° representing radicals which are identical to or different from one another and correspond to hydrogen or a linear, branched or cyclic alkyl having from 1 to 8 carbon atoms, preferably -CH3 or -CH2CH3.
  • radical B in particular halogens, corresponding to formula (I), can represent an alkylene which corresponds to the following formulas:
  • R 1 , R 2 which are identical or different, each represent CH 3 CH 2 - or CH 3 - (preferably R 1 represents CH 3 CH 2 - and R 2 represents CH 3 -);
  • reaction pressure is, for example, ambient atmospheric pressure.
  • the method according to the invention may comprise continuous sequences. It is preferably semi-continuous.
  • the process according to the invention is applicable, for example, to the preparation of organomonoalkoxysilanes (I) of formulas: ## STR1 ## First implementation mode (halogenated organomonoalkoxysilanes): CH 3
  • the invention also relates to the use of an organomonoalkoxysilane of formula
  • the symbols R 1 , R 2 identical or different, preferably represent each CH 3 CH 2 - or CH 3 - (preferably R 1 represents CH 3 CH 2 - and R 2 represents CH 3 -), the symbol M represents Mg, the symbol X 1 represents Cl.
  • R 1 , R 2 , B, Y and W of formulas (I) and (VIII) are as defined above.
  • the nucleophilic agent with which the synthetic intermediate (I) is capable of reacting for the production of functionalized organosilanes of formula (VIII) can be of different types.
  • it may be, for example, nucleophilic agents as described on page 12, line 10 to page 14, line 27 of application WO-A-03/027125.
  • reference may be made for more details to the content of, for example, EP-A-0 848 006, which illustrates, starting from other reagents, operating procedures applicable to driving. of the synthesis considered.
  • Phase -a- In a double jacket reactor: Phase -a-:
  • Phase -a- In a double jacket reactor: Phase -a-:
  • Example 3 Isolation with treatment of magnesium salts to facilitate the separability of the reaction medium
  • Phase -a- In a double jacket reactor: Phase -a-:
  • Phase -c- • Charge the Isopar M (S2) (200 g) at 15-25 0 C

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
EP08717421A 2007-03-08 2008-03-05 Procede de traitement d'alcoxysilanes a l'aide d'un compose organometallique, en particulier pour preparer des organomonoalcoxy (ou monohydroxy)silanes Withdrawn EP2134728A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0701706A FR2913423B1 (fr) 2007-03-08 2007-03-08 Procede de traitement d'alcoxysilanes a l'aide d'un compose organometallique, en particulier pour preparer des organomonoalcoxy(ou monohydroxy)silanes.
PCT/EP2008/052671 WO2008110490A2 (fr) 2007-03-08 2008-03-05 Procede de traitement d'alcoxysilanes a l'aide d'un compose organometallique, en particulier pour preparer des organomonoalcoxy (ou monohydroxy)silanes

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EP2134728A2 true EP2134728A2 (fr) 2009-12-23

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US (1) US8461369B2 (zh)
EP (1) EP2134728A2 (zh)
JP (1) JP5385160B2 (zh)
CN (1) CN101687894B (zh)
FR (1) FR2913423B1 (zh)
WO (1) WO2008110490A2 (zh)

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CN111892560B (zh) * 2020-07-20 2022-08-12 湖北华邦化学有限公司 一种分步格氏法中四氢呋喃的回收处理工艺

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JPH0739427B2 (ja) * 1987-04-03 1995-05-01 信越化学工業株式会社 モノアルコキシシラン化合物の製造方法
JPH02178293A (ja) * 1988-12-28 1990-07-11 Toray Dow Corning Silicone Co Ltd ハロアルキルジアルキルアルコキシシランの製造方法
JP2795135B2 (ja) * 1993-06-07 1998-09-10 信越化学工業株式会社 オルガノアルコキシシラン化合物の製造方法
DE19651849A1 (de) 1996-12-13 1998-06-18 Degussa Verfahren zur Herstellung von Bis(silylorganyl)-polysulfanen
DE19954635A1 (de) * 1999-11-13 2001-05-17 Degussa Verfahren zur Herstellung von Alkoxysilanen
JP2002179687A (ja) * 2000-12-18 2002-06-26 Dow Corning Toray Silicone Co Ltd オルガノアルコキシシランの製造方法
FR2830013B1 (fr) * 2001-09-21 2005-02-25 Rhodia Chimie Sa Procede d'obtention de monoorganoxysilanes halogenes utilisables notamment en tant qu'intermediaires de synthese
FR2830014B1 (fr) * 2001-09-21 2005-02-18 Rhodia Chimie Sa Procede d'obtention de monoorganoxysilanes halogenes utilisables notamment en tant qu'intermediaires de synthese

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Title
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WO2008110490A3 (fr) 2008-11-06
CN101687894A (zh) 2010-03-31
WO2008110490A2 (fr) 2008-09-18
JP5385160B2 (ja) 2014-01-08
CN101687894B (zh) 2014-11-26
FR2913423A1 (fr) 2008-09-12
US8461369B2 (en) 2013-06-11
FR2913423B1 (fr) 2009-04-17
JP2010520260A (ja) 2010-06-10
US20100185005A1 (en) 2010-07-22

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