EP2097425A2 - Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylen - Google Patents

Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylen

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Publication number
EP2097425A2
EP2097425A2 EP07822451A EP07822451A EP2097425A2 EP 2097425 A2 EP2097425 A2 EP 2097425A2 EP 07822451 A EP07822451 A EP 07822451A EP 07822451 A EP07822451 A EP 07822451A EP 2097425 A2 EP2097425 A2 EP 2097425A2
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EP
European Patent Office
Prior art keywords
iii
group
reaction
solvent
θebsl
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EP07822451A
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English (en)
French (fr)
Inventor
Gérard Mignani
Samir Mansouri
Samuel Arthaud
Thierry Vidal
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Rhodia Operations SAS
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Rhodia Operations SAS
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Publication of EP2097425A2 publication Critical patent/EP2097425A2/de
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02Silicon compounds
    • C07F7/08Compounds having one or more C—Si linkages
    • C07F7/18Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804Compounds having Si-O-C linkages
    • C07F7/1872Preparation; Treatments not provided for in C07F7/20
    • C07F7/1876Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages

Definitions

  • the present invention relates to a novel route for the synthesis of functionalized, and in particular unsaturated (for example alkenyl) organomonoalkoxy (or monohydroxy) silanes, which can be used especially as synthesis intermediates in organic chemistry, for the production of organomonoalkoxy (or monohydroxy) silanes.
  • functionalized by groups other than alkenyls for example by amino, thiol or polysulfide groups.
  • the invention also provides compositions containing such synthetic intermediates in organic chemistry.
  • the technical problem underlying the invention is to find an alternative to the known techniques for the synthesis of functionalized organomonoalkoxy (or monohydroxy) silanes, which may allow their improvement, for example with regard to yield, productivity, cost and respect the environment.
  • Patent Application JP-A-2002179687 discloses a process for producing halogenated organoalkoxysilanes comprising the following steps (i) to (iii): (i) reaction of a tetralcoxysilane [Si (OCHs) 4 ] or a trialkoxysilane with a organomagnesium compound halogen [e.g. (C 5 H 4) -MgCl or (COHS) -MgCl] in solution in an ether solvent such as tetrahydrofuran (THF); this reaction takes place in a nonpolar solvent (for example xylene) and having a boiling point higher than that of the ethereal solvent containing the halogenated organomagnesium compound,
  • a nonpolar solvent for example xylene
  • step (ii) maintaining the reaction medium of step (i) at an elevated temperature of the order of 150 ° C., optionally under reduced pressure, so as to distil the ethereal solvent (THF), the reaction between the tetraalkoxysilane or the trialkoxysilane and the halogenated organomagnesium compound continuing to obtain a reaction suspension (slurry), and
  • magnesium salts formed in the process according to the patent application JP-A-2002179687 pose serious problems of environmental management of the effluents, in particular because of the reactivity of these salts. They react exothermically with water, releasing ethanol. In addition, these magnesium salts constitute a high pollutant load in the effluents (very high chemical demand in
  • 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)
  • B is a divalent residue of formula - (CH 2 ) S-,
  • R 2 identical or different, each represent a group -CH 3 ,
  • the synthetic route according to the patent application JP-A-2002179687 and the application WO-A-03/027125 is a route involving a trialkoxysilane functionalized with a halogenated alkyl group and a Grignard type reaction mechanism, which involves a so-called halogenomagnetic Grignard reagent, such as MeMgCl.
  • organomonoalkoxy (or monohydroxy) silanes functionalized with a group other than a halogen group, for example an alkenyl group.
  • the lack of selectivity of the Grignard pathway results in the production of organomonoalkoxy (or monohydroxy) silanes with low yields due to the presence of co-products such as organo-bisallylsilane.
  • the reaction also generates annoying byproducts, namely insoluble or soluble magnesium salts which may constitute an obstacle to the separation and the collection of the targeted product.
  • EP 0798302 discloses a process for the preparation of allylsilane comprising contacting magnesium metal with a mixture comprising diethylene glycol dibutyl ether, a halide (allyl chloride) and a halosilane (trimethylchlorosilane), at a temperature between 5 and 200 0 C.
  • the allylsilanes obtained are for example allyldimethylhydrogensilane, allylméthylhydrogénochlorosilane, allyltriméthylsilane, allyldiméthylchlorosilane and allylméthyldichlorosilane. It is not in any case alkoxysilanes or hydroxysilanes.
  • One of the objectives of the present invention is to provide an alternative to the known synthesis of functionalized organomonoalkoxy (or monohydroxy) silanes, in particular alkenyl (for example dimethylethoxyallylsilane), especially useful as synthesis intermediates in organic chemistry, which may allow preferably an improvement, for example in terms of productivity, efficiency, selectivity, simplicity of implementation, cost reduction, compatibility with respect to the environment and / or availability of consumable reagents used.
  • Another object of the invention is to provide a process for the preparation of functionalized organomonoalkoxy (or monohydroxy) silanes, in particular alkenyl, capable of reacting with a nucleophilic agent to produce organomonoalkoxy (or monohydroxy) silanes functionalized by a different group of an alkenyl functional group, for example an amine, thiol or polysulfide functional group.
  • a nucleophilic agent capable of reacting with a nucleophilic agent to produce organomonoalkoxy (or monohydroxy) silanes functionalized by a different group of an alkenyl functional group, for example an amine, thiol or polysulfide functional group.
  • An object of the invention is also to provide novel compositions of synthesis intermediates based on functionalized organomonoalkoxy (or monohydroxy) silanes, in particular alkenyl, reduced bi-functional organomonoalkoxy (or monohydroxy) silanes.
  • Another object of the invention is to provide a process for the preparation of monofunctionalized organomonoalkoxy (or monohydroxy) silanes, in particular monoalkenyls, of such compounds which can constitute a new raw material opening new ways of obtaining organomonoalkoxy (or monohydroxy monofunctionalized silanes with a group other than an alkenyl functional group, for example by a group chosen from amine, thiolated or polysulphurized functional groups, in particular polysulphurized groups in which the polysulfurized entity is linked at both ends to organomonoalkoxy residues ( or monohydroxy) silanes.
  • An object of the present invention is also to provide a process for the preparation of functionalized organomonoalkoxy (or monohydroxy) silanes, in particular alkenylated, having a very good selectivity in monoallyl-diorganomonoalkoxy (or monohydroxy) silanes and achievable in concentrated reaction medium , so as to improve productivity and this, avoiding the use of Grignard organomagnesium reagents that pose particular security constraints, particularly during storage.
  • Another objective of the invention is to propose an alternative route to the "Grignard" access route to allyl-alkoxy (or monohydroxy) silanes.
  • R 1 represents hydrogen or a monovalent hydrocarbon group chosen from a linear, branched or cyclic alkyl radical having from 1 to 20 carbon atoms and a linear, branched or cyclic alkoxyalkyl radical having from 1 to 20 carbon atoms; carbon atoms;
  • R 2 which are identical or different, each represent 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 -C 18 alkyl-C 6); R 2 optionally carrying at least one halogen or perhalogenated group;
  • Y represents an organic monovalent functional group, preferably selected from the functional groups "sensitive" R 3 comprising at least one ethylenic unsaturation and / or acetylenic, particularly selected from: • R 3'1 alkenyl, linear , branched or cyclic, having from 2 to 10 carbon atoms,
  • the symbols R 1 , R 2 and Y are as defined above, the symbol M corresponds to a metal chosen from the group comprising Mg,
  • the symbol X represents a halogen (symbol HaI), preferably a chlorine, bromine or hydrogen atom. iodine, o and in that it comprises the following steps:
  • the temperature of the reaction medium is preferably maintained at a temperature ⁇ r less than or equal to the boiling temperature ⁇ ebS1 of the solvent S 1;
  • the boiling temperature " ⁇ eb" of a compound corresponds to its initial boiling point, according to the ASTM D 86-99 standard test.
  • One of the essential steps of the process according to the invention is the stage of progressive and controlled introduction of the halogenated organic compound (III) into the reaction medium.
  • the introduction of the halogenated organic compound (III), for example the allyl halide is preferably slower than the consumption of said compound (III) in the reaction.
  • the compound (III) is in liquid form and is then called casting liquid (III) in the reaction medium.
  • the control of this speed of introduction can be done by any appropriate means.
  • the temperature is a physical parameter reflecting the amount of compound (III) added to the reaction medium.
  • An alternative, which may or may not be combined with the measurement of the reaction temperature consists in measuring the concentration of compound (III) in the reaction medium, preferably continuously or semi-continuously, and by any appropriate and known means of the reaction medium. skilled person. It may be for example gas chromatography.
  • the halogenated organic compound (III) is introduced into the reaction medium in equivalent molar amount, or even in slight excess or slight defect, with respect to the alkoxysilane (II) starting material.
  • short defect or excess is meant, for example, within the meaning of the invention, a margin of ⁇ 5 mol%.
  • the process according to the present 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 many constraints in terms of 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".
  • the fact of using the metal (M), preferably magnesium, in metallic form makes it possible to reduce the consumption of metal and, above all, constitutes an advantageous alternative compared to the use of a Grignard RMgX reagent in solution, delicate to prepare and store.
  • the selectivity performance of the process of the invention is reflected in terms of yield and productivity, among others.
  • the gains in yield of the compound (I) are advantageously at least 150% relative to the known Larsson technique and that the methyltrietoxysilane and the allyl chloride are added together with the mixture in the reaction medium containing the turnings of magnesium metal.
  • the silane with an isolated transformation ratio of at least 65%, in particular at least 70%, or even at least 75% or even 85%, and a purity higher than or equal to 95%, and especially with a very high selectivity, especially at least 98%: for example, a single allylation occurs when Y is an allyl.
  • the level of Si-O-Si oligomers formed is very low, for example less than 1 mol%.
  • 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), especially magnesium are stoichiometric. It is also possible to use an excess of metal (especially magnesium) to further limit the formation of bis-allyl.
  • the preferred radicals R 1 are chosen from the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, CH 3 OCH 2 -,
  • radicals R 1 are chosen from methyl, ethyl, n-propyl and isopropyl, ethyl being particularly preferred.
  • the preferred radicals R 2 are chosen from the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, n-hexyl and phenyl; more preferably, the radicals R 2 are methyls.
  • radical Y can represent:
  • R representing radicals identical to or different from each other and corresponding to hydrogen or to a linear, branched or cyclic alkyl having from 1 to 8 carbon atoms, preferably -CH 3 , -CH 2 CH 3 .
  • At least one of the following definitions is (are) verified in formulas (I), (II) and (III) : the symbols R 1 and R 2 , which are identical or different, each represent hydrogen,
  • solvent S1 is generally an important parameter of the process according to the invention.
  • Sl can be chosen for example from the group of solvents having a boiling temperature ⁇ ebSl lower than the boiling temperature ⁇ eb (I) of the compound
  • 51 may be chosen from the group of solvents having a boiling point ⁇ ebSl generally less than 150 ° C. (below 760 mmHg), for example less than
  • S 1 is selected from the group of ethereal organic solvents and / or from the group of acetals, and even more preferably from the subgroup comprising tetrahydrofuran (THF), methyl-THF (Me-THF). dialkyl ethers (preferably diethyl ether or even more preferably dibutyl ether), dioxanes and mixtures thereof.
  • THF tetrahydrofuran
  • Me-THF methyl-THF
  • dialkyl ethers preferably diethyl ether or even more preferably dibutyl ether
  • S2 corresponds in particular to the optional step -f- and is intended to contain in solid or solubilized form any metal salts (in particular magnesium) likely to form in the reaction medium.
  • S2 is intended to allow easier separation and collection of the object compound (I) during step -g-, namely, preferably, distillation and, more preferably still, distillation under reduced pressure.
  • S2 does not react with any metal salts (for example magnesium).
  • S2 is different from S1.
  • the 52 is preferably chosen from the group of solvents having a boiling temperature ⁇ ebS2 greater than the boiling temperature ⁇ eb (I) of the organomonoalkoxy (or monohydroxy) silane (I), and advantageously greater than the boiling temperature ⁇ ebSl solvent S1.
  • S2 is sufficiently heavy to be the last to distill with respect to the compound (I) and the solvent S 1.
  • solvent S2 it is possible to favor, for example, solvents chosen from the group of solvents having a boiling point ⁇ ebS2 greater than 126 ° C.
  • 760 mm Hg generally at least 150 0 C (at 760 mm Hg), and in particular in the solvent group defined as follows: 150 0 C ⁇ ebS2, preferably 180 0 C ⁇ ebS2 and more preferably still, 190 ° C. ⁇ ebS2 ⁇ 350 ° C. (below 760 mmHg).
  • S2 in the group of solvents including hydrocarbons, hydrocarbon cuts, compounds
  • S 2 can be selected from methylal, anisole and diphenyl ether.
  • S2 solvents include petroleum fractions or hydrocarbon fractions, in particular those sold under the name ISOPAR ® M, N or P, by Exxon Mobil Chemical, or else alkylbenzene.
  • 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 step -f - optional is advantageously associated not only with a step -g- 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 optional step -h'- which intervenes, advantageously, after the step -g- 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 is preferably carried out by adding an aqueous acidic solution.
  • the metal salts for example magnesian
  • the possible addition of S2 takes place not only during step -a- and / or during the possible step -f-, but also at any time of the process. preferably before and / or during step -g-, at least once.
  • 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, about 2: 1.
  • the amount of the solvent S 2 used in the reaction medium may for example be between 50 and 300 g per 300 g of reaction medium before the step -h- separation and collection of the compound (I).
  • ⁇ r can depend on operating conditions of the process, in particular the type of casting of the halogenated organic compound (III).
  • the temperature ⁇ r can be for example 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 hexenyl cyclic 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.
  • an M / (II) molar ratio of between 1.4: 1 and 1: 1, preferably between 1 , 3: 1 and 1.1: 1, and even more preferably equal to about 1.2: 1.
  • reaction pressure is, for example, ambient atmospheric pressure.
  • the bringing together of the metal M, for example magnesium, with the solvent S1, for example the anhydrous ether may consist of disposing of metal turnings, chips or the like in a reactor and then adding the solvent S1, or possibly a solvent S2, in the latter.
  • Step -b This optional activation may be catalytic type chemical, by adding a catalytic amount of at least one halogen and / or an alkyl halide.
  • the halogen (X ') optionally introduced is a grain or an iodine crystal with or without a solvent of the type 1, 2-dibromoethane or any other haloalkane.
  • This catalytic type chemical activation can be supplemented or replaced by a thermal activation of the metal M, which consists, for example, in simply leaving said metal M for several minutes at an activation temperature close to the temperature of the reaction medium ⁇ r.
  • An indicator of the end of the activation period may advantageously be the discoloration of the reaction medium.
  • the organoalkoxysilane (II) is added to the reaction medium without particular precautions.
  • organoalkoxysilane (II) for example dialkoxydialkylsilane wherein R1 is methyl and R2 is methyl, may be added prior to the introduction of the halogen X '.
  • Step -d- The halogenated organic compound (III), preferably the allyl halide, is slowly introduced into the reaction medium, which is maintained at a temperature ⁇ r, corresponding for example to about 80% of the boiling point.
  • ⁇ ebSl of the solvent Sl In practice, this can be for example about 30 0 C when S1 is diethyl ether and about 50 0 C when S1 is tetrahydrofuran.
  • the reaction (II / III) can take place for several hours at a temperature ⁇ r, for example for 1 to 36 hours, preferably for 1 to 24 hours.
  • the temperature of the reaction medium is controlled by the rate of introduction of the halogenated organic compound (III) as well as by any known and appropriate temperature maintenance means (for example by the use of a refrigerant reaction chamber).
  • solvent S2 is carried out conventionally without any particular precaution.
  • the amount of solvent S2 used is such that the reaction medium can be easily stirred and / or transferred from one place to another.
  • Distillation is one of the appropriate methods among others for selectively isolating the organomonoalkoxy (or mono) silane (I) from the reaction medium.
  • ⁇ ebS2 be greater than ⁇ eb (I) in the case where S2 is used.
  • this distillation can be carried out at a temperature between
  • the filter used may be a glass frit, a wire mesh filter, etc.
  • the solvent used for washing the cake is advantageously Sl and / or S2.
  • This optional step of solubilizing metal salts is an alternative to the step -h-.
  • the -h'- step just like the -h- step, preferably occurs after a distillation -g- of the target functionalized organomonoalkoxy (or monohydroxy) silane (I). It is preferably carried out using an acidic aqueous solution, for example based on at least one strong acid (especially mineral acid), such as HCl, in particular so as to bring the pH of the reaction medium to a pH that is advantageously equal to at about 4.0-4.5.
  • This optional hydrolysis step is preferably carried out by rapid or gradual addition of a hydrolysis agent, preferably water, or, alternatively, a solution, in particular a hydroorganic solution, for example buffered with a pH of between 4.5 and 8 and according to a stoichiometry such that there is 1 to 2 equivalents (for example 1.5 equivalents) of water per equivalent of organomonoalkoxy (or mono) silane (I).
  • a hydrolysis agent preferably water, or, alternatively, a solution, in particular a hydroorganic solution, for example buffered with a pH of between 4.5 and 8 and according to a stoichiometry such that there is 1 to 2 equivalents (for example 1.5 equivalents) of water per equivalent of organomonoalkoxy (or mono) silane (I).
  • the hydrolysis temperature is between 40 and 90 ° C., in particular between 50 and 90 ° C., for example between 70 and 80 ° C.
  • the removal of the metal salts is even easier, these being in the form of an aqueous solution.
  • One of the essential points of the process of the invention is to propose a slow introduction of the compound (III) into the reaction medium, so that the latter always has a low or even zero concentration of Grignard reagent as well as in compound (III) (in particular allyl halide).
  • the reaction medium does not advantageously comprise solid Grignard reagent and therefore does not carry the constraints related to the Grignard type reaction mechanism (in particular the storage problem).
  • the process according to the invention may comprise continuous sequences, but it is preferably semi-continuous.
  • the product (I) obtained at the end of the process described above is a synthesis intermediate, in particular capable of reacting with at least one nucleophilic agent for the production of other organoalkoxysilanes functionalized with groups Y other than R 3 groups, in particular by groups other than alkenyls, for example by amino, thiol or polysulfide functional groups.
  • the nucleophilic agent with which the synthesis intermediate (I) is capable of reacting for the production of these organoalkoxysilanes functionalized with groups Y other than the groups R 3 can be of different natures.
  • it may be a nucleophilic agent of the type of those described in the application WO-A-03/027125 (page
  • the present invention also relates to a composition (synthetic intermediates composition) comprising: an effective amount of at least one organomonoalkoxy (or monohydroxy) silane of formula (I) (directly) obtained by the process according to the invention:
  • R 1 , R 2 and Y being as defined above; at most 5%, preferably at most 1% and more preferably at most 0.5%, by weight of:
  • R 2 and Y being as defined above.
  • the symbols R 1 and R 2 which are identical or different, each represent CH 3 CH 2 - or CH 3 - (more preferably, R 1 represents CH 3 CH 2 - and R 2 represents CH 3 -) and the symbol Y represents a group R 3 , more preferred is an alkenyl group and, more preferably still, an allyl or methallyl group.
  • EXAMPLE 5 1.04 g (42.7 mmol) of Mg in turnings and 8 ml of anhydrous ether are introduced into a 100 ml three-necked flask under argon. 4.4 ml of dichlorodimethylsilane (36.2 mmol) and one iodine grain are then introduced. 3.9 ml (47.4 mmol) of allyl chloride are then added. The reaction is exothermic. The temperature is maintained at 40 ° C. for 40 minutes. Then it is maintained 24 hours at room temperature. The reaction mass is treated with 20 ml of ethanol and 20 ml of triethylamine. The reaction mass is filtered. The filtrate is then taken up in 50 ml of ether.
  • EXAMPLE 7 In a strictly anhydrous 250 ml three-necked flask, with temperature probe, magnetic stirrer, oil bath, refrigerated and under argon, 2.47 g of Mg in turns (1.2 eq.), 80 ml of diethylene glycol are introduced. dry dibutyl ether, 1 grain of iodine. The Mg is allowed to activate for 20 minutes at 100 ° C. Once the reaction mass is decolorized, and still at 100 ° C., 400 ⁇ l of dibromoethane is introduced until a cloud in the reaction mass appears. 14.6 ml of diethoxydimethylsilane are then introduced.
  • the reaction mass is then distilled under reduced pressure (minimum pressure: 350 mbar), using a packed column of 60 cm, with retrogradation and a reflux ratio of 1/10. After distillation, the isolated yield of allyldimethylethoxysilane is 79%, without formation of bisallydimethylsilane.
  • the organic phase thus obtained is washed with 7 times 30 ml of water.
  • the organic phase is dried over MgSO 4 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
EP07822451A 2006-11-10 2007-11-09 Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylen Withdrawn EP2097425A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0609839A FR2908412B1 (fr) 2006-11-10 2006-11-10 Procede de preparation d'organomonoalcoxy (ou monohydroxy) silanes fonctionnalises, en particulier alcenyles
PCT/EP2007/062163 WO2008055984A2 (fr) 2006-11-10 2007-11-09 Procede de preparation d'organomonoalcoxy(ou monohydroxy)silanes fonctionnalises, en particulier alcenyles

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EP2097425A2 true EP2097425A2 (de) 2009-09-09

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JP5675581B2 (ja) * 2011-12-27 2015-02-25 東レ・ダウコーニング株式会社 有機珪素化合物の製造方法
CN115449080B (zh) * 2022-08-16 2024-03-01 宁波杭州湾新材料研究院 一种碳硅烷高分子及其制备方法

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US2442053A (en) * 1945-06-06 1948-05-25 Corning Glass Works Dialkylated silicon esters and method of making them
US4650891A (en) * 1986-05-02 1987-03-17 Monsanto Company Catalytic process for producing silahydrocarbons
US4777278A (en) * 1987-10-08 1988-10-11 Akzo America Inc. Synthesis of alkyl cycloalkyl dialkoxysilanes
DE3821483C2 (de) * 1988-06-25 1996-04-11 Witco Gmbh Verfahren zur Herstellung von Diorganodialkoxysilanen
US5629439A (en) * 1996-03-28 1997-05-13 Dow Corning Corporation Method for preparation of allylsilanes
US5756796A (en) * 1997-05-19 1998-05-26 Dow Corning Corporation Method for preparation of alkenylsilanes
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
DE10159859C1 (de) * 2001-12-06 2003-01-16 Fraunhofer Ges Forschung Verfahren zur Herstellung von Styryl-funktionalisierten Silanen

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US20100140541A1 (en) 2010-06-10
WO2008055984A3 (fr) 2008-10-16
FR2908412B1 (fr) 2010-10-15
WO2008055984A2 (fr) 2008-05-15
FR2908412A1 (fr) 2008-05-16

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