US20070185344A1 - Method of preparing halogenoalkyldialkyl chlorosilane - Google Patents
Method of preparing halogenoalkyldialkyl chlorosilane Download PDFInfo
- Publication number
- US20070185344A1 US20070185344A1 US10/561,223 US56122304A US2007185344A1 US 20070185344 A1 US20070185344 A1 US 20070185344A1 US 56122304 A US56122304 A US 56122304A US 2007185344 A1 US2007185344 A1 US 2007185344A1
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- US
- United States
- Prior art keywords
- hal
- formula
- auxiliary
- iii
- uhc
- 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.)
- Abandoned
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- 238000000034 method Methods 0.000 title claims description 33
- 239000005046 Chlorosilane Substances 0.000 title 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 title 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims abstract description 27
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000012429 reaction media Substances 0.000 claims abstract description 19
- 150000002576 ketones Chemical class 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 7
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 7
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 7
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
- 150000004053 quinones Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 5
- BJLJNLUARMMMLW-UHFFFAOYSA-N chloro-(3-chloropropyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCl BJLJNLUARMMMLW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 33
- 239000003446 ligand Substances 0.000 claims description 22
- 229910052741 iridium Inorganic materials 0.000 claims description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 15
- -1 alkenyl halide Chemical class 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910000077 silane Inorganic materials 0.000 claims description 11
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 6
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 6
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 4
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 claims description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 claims description 3
- UPGHEUSRLZSXAE-UHFFFAOYSA-N 2-prop-2-enylcyclohexan-1-one Chemical compound C=CCC1CCCCC1=O UPGHEUSRLZSXAE-UHFFFAOYSA-N 0.000 claims description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 3
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 claims description 3
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- FEWIGMWODIRUJM-HWKANZROSA-N (E)-4-hexen-3-one Chemical compound CCC(=O)\C=C\C FEWIGMWODIRUJM-HWKANZROSA-N 0.000 claims description 2
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
- FNOOZJAPZFHNCW-UHFFFAOYSA-N 2-methylidenebicyclo[2.2.1]heptan-3-one Chemical compound C1CC2C(=O)C(=C)C1C2 FNOOZJAPZFHNCW-UHFFFAOYSA-N 0.000 claims description 2
- ZLODZDLDZBRDLS-UHFFFAOYSA-N 2-prop-1-enyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound CC=C[SiH]1O[SiH2]O[SiH2]O[SiH2]O1 ZLODZDLDZBRDLS-UHFFFAOYSA-N 0.000 claims description 2
- SPTVCXKSSRBTMN-UHFFFAOYSA-N 3-(2-oxocyclohexyl)propanenitrile Chemical compound O=C1CCCCC1CCC#N SPTVCXKSSRBTMN-UHFFFAOYSA-N 0.000 claims description 2
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 claims description 2
- UPEUQDJSUFHFQP-UHFFFAOYSA-N 4-phenylbut-3-yn-2-one Chemical compound CC(=O)C#CC1=CC=CC=C1 UPEUQDJSUFHFQP-UHFFFAOYSA-N 0.000 claims description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 2
- FEWIGMWODIRUJM-UHFFFAOYSA-N hex-4-en-3-one Natural products CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 claims 1
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 150000002503 iridium Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RIVWZEZVZPBUNR-UHFFFAOYSA-N C.C.C=CC.C=CCCl.C[SiH](C)Cl.C[Si](C)(Cl)CCCCl.C[Si](C)(Cl)Cl.I.II.I[IH]I Chemical compound C.C.C=CC.C=CCCl.C[SiH](C)Cl.C[Si](C)(Cl)CCCCl.C[Si](C)(Cl)Cl.I.II.I[IH]I RIVWZEZVZPBUNR-UHFFFAOYSA-N 0.000 description 1
- NCSWRLFKBWCUKM-UHFFFAOYSA-N C.C=CCCl.C[SiH](C)Cl.C[Si](C)(Cl)CCCCl Chemical compound C.C=CCCl.C[SiH](C)Cl.C[Si](C)(Cl)CCCCl NCSWRLFKBWCUKM-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
Definitions
- the present invention relates to a process for the preparation of haloalkyldialkylhalosilane.
- the present invention relates to a process for the preparation of 3-halopropyldimethylchlorosilane by hydrosilylation of dimethylhydrochlorosilane using allyl chloride and a catalyst based on a platinum ore metal, in particular iridium, and optional recovery of the said metal.
- the reaction involved in this example is as follows:
- Another route for improving the economics of the process would be to optimize the activity of the catalyst. To do this, it is arranged for the degree of conversion (DC) of the hydrosilane (II) to be increased or, for a given DC, for the selectivity (S) of the catalyst to be significantly increased.
- DC degree of conversion
- S selectivity
- BE-B-785343 (U.S. Pat. No. 3,798,252) discloses the hydrosilylation of allyl chloride by trichlorohydrosilane in the presence of chloroplatinic acid in solution in cyclohexanone (removal of water from the solution using Na 2 SO 4 ). The ketone is combined with the platinum in order to improve the selectivity of the reaction.
- Another essential object of the invention is to provide a process for the preparation of a haloalkyldialkylhalosilane of the above type which is effective, economical and easy to implement.
- a catalyst based on iridium in the oxidation state 1 in the structure of which each iridium atom corresponds to the complex form of the Ir(L) 3 X type where the symbols L and X have the definitions given in the work “Chimie Organométallique” [Organometallic Chemistry] by Didier Astruc, published in 2000 by EDP Sciences (cf. in particular page 31 et seq.).
- the catalyst corresponds to the formula (I): [Ir(R 4 ) x (R 5 )] y (IV)
- the ligands R 4 of the preferred catalyst (IV) can be identical to or different from the UHCs (v) of the auxiliary.
- the iridium-based catalyst can be supported, as is disclosed, for example, in U.S. Pat. No. 6,177,585 and GB-A-1 526 324.
- the catalytic system used in accordance with the process according to the invention makes it possible to reduce the amount of catalyst necessary for the achievement of a full degree of conversion DC of the silane of formula (II): (Hal-(R 2 R 3 )Si—H) and/or to increase the selectivity S for a given and fixed DC.
- auxiliaries can be used in the liquid or solid form. Provided that they are liquid, they can be introduced in an amount such that, in the reaction medium, they, in addition to acting as hydrosilylation promoter, act as solvent for the reaction.
- solvent of the auxiliary can also make it possible, in particular when it is a heavy solvent (namely, a solvent having a boiling point at atmospheric pressure which is greater than that of the compound of formula (I), such as, for example, a polyether), to improve the stability of the reaction medium and thus the safety of the process.
- a heavy solvent namely, a solvent having a boiling point at atmospheric pressure which is greater than that of the compound of formula (I), such as, for example, a polyether
- this offers possibilities of easy recovery of the catalyst and thus of recycling the latter.
- the auxiliary When the auxiliary is in the free state, it can be introduced into the reaction medium according to a molar ratio, with respect to the iridium metal, of at least 0.2, preferably of at least 1. Depending on the nature of the ligands, a molar ratio of greater than 10 and even of greater than 100 can more preferably be chosen.
- the concentration of catalyst (preferably IV) is such that the iridium/ silane of formula (II) molar ratio is less than or equal to 400 ⁇ 10 ⁇ 6 , preferably less than or equal to 200 ⁇ 10 6 and more preferably still less than or equal to 50 ⁇ 10 ⁇ 6 .
- ketones (i) to those defined in U.S. Pat. No. 3 798 252 et in PL-A-176036, PL-A-174810, PL-A-145670 and JP-A-75024947.
- the auxiliary is selected from the group consisting in particular of: cyclohexanone, 2-cyclohexen-1-one, isophorone, 2-benylidenecyplohexanone, 3-methylene-2-norbornanone, 4-hexen-3-one, 2-allylcyclohexanone, 2-oxo-1-cyclohexanepropionitrile, 2-(1-cyclohexenyl)cyclohexanone, monoglyme, ethylene glycol divinyl ether, ethyl ether, benzoquinone, phenylbenzoquinone, maleic anhydride, allyl succinic anhydride, 3-benzylidene-2,4-pentadione, phenothiazine, (methylvinyl)cyclotetrasiloxane (vinylated D4), 4-phenyl-3-butyn-2-one, 1,3-butadiene, 1,5-hexadiene, 1,3-(vin
- the auxiliary is a mixture (vi) comprising at least one UHC (v), preferably COD, and at least one ketone (i), preferably cyclohexanone, and/or at least one ether (ii) and/or at least one quinone (iii).
- the concentration of catalyst, preferably of formula (IV), is such that the iridium/silane of formula (II) molar ratio is less than or equal to 100 ⁇ 10 ⁇ 6 , preferably less than or equal to 60 ⁇ 10 ⁇ 6 , and more preferably still is between 40 ⁇ 10 ⁇ 6 and 1 ⁇ 10 ⁇ 6 .
- the components of the mixture (vi), UHC/(i) and/or (ii) and/or (iii), are present in the reaction medium when the reaction begins.
- the process according to the invention can be employed either continuously, semicontinuously or batchwise.
- the product of formula (I) is 3-chloropropyldimethylchlorosilane
- the product of formula (II) is dimethylhydrochlorosilane
- the product of formula (III) is allyl chloride.
- the invention relates to a catalytic system for the preparation of a haloalkyldialkylhalosilane of formula (I): Hal-(R 2 R 3 )Si—(CH 2 ) s -Hal by hydrosilylation reaction of a reaction medium comprising:
- the tests are carried out in parallel reactors.
- Each reactor is equipped with a magnetic stirrer, with a reflux condenser and with a thermometer.
- the heat-exchange fluid is brought to a temperature of ⁇ 35° C., which makes it possible to obtain a material balance always greater than 95% by weight.
- hydrosilylation auxiliaries The effect of the hydrosilylation auxiliaries is compared with a control reaction, where only di- ⁇ -chlorobis( ⁇ -1,5-cyclooctadiene)diiridium was used.
- a control reaction where only di- ⁇ -chlorobis( ⁇ -1,5-cyclooctadiene)diiridium was used.
- an intentionally low amount of catalyst was introduced in order to obtain a degree of conversion of the corresponding SiH functional groups of the order of 50%.
- the dimethylhydrochlorosilane with a purity of 99% by weight, is added by running onto a heel, composed of the allyl chloride (1.05 mol. eq./silane) and of the catalytic system
- the reaction medium is analyzed by gas chromatography calibrated with n-tetradecane.
- the dimethylhydrochlorosilane with a purity of 99% by weight, is introduced into the reaction medium via a peristaltic pump. 107.15 g (1.117 mol) thereof are introduced over 2 hours 30 minutes. The flow rate for introduction is adjusted in order to maintain the temperature of the reaction medium between 20 and 25° C., taking into account the high exothermicity of the reaction. The reaction medium is kept stirred for 20 minutes after the end of the introduction of the dimethylhydrochlorosilane.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silicon Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0350222 | 2003-06-17 | ||
| FR0350222A FR2856402B1 (fr) | 2003-06-17 | 2003-06-17 | Procede de preparation d'halogenoalkylchlorosilane |
| PCT/FR2004/001487 WO2004113354A2 (fr) | 2003-06-17 | 2004-06-16 | Procede de preparation d'halogenoalkyldialkyl-chlorosilane |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR2004/001487 A-371-Of-International WO2004113354A2 (fr) | 2003-06-17 | 2004-06-16 | Procede de preparation d'halogenoalkyldialkyl-chlorosilane |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/173,968 Continuation US7884225B2 (en) | 2003-06-17 | 2008-07-16 | Process for the preparation of halogenoalkyldialkyl chlorosilane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20070185344A1 true US20070185344A1 (en) | 2007-08-09 |
Family
ID=33484723
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/561,223 Abandoned US20070185344A1 (en) | 2003-06-17 | 2004-06-16 | Method of preparing halogenoalkyldialkyl chlorosilane |
| US12/173,968 Expired - Fee Related US7884225B2 (en) | 2003-06-17 | 2008-07-16 | Process for the preparation of halogenoalkyldialkyl chlorosilane |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/173,968 Expired - Fee Related US7884225B2 (en) | 2003-06-17 | 2008-07-16 | Process for the preparation of halogenoalkyldialkyl chlorosilane |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20070185344A1 (de) |
| EP (1) | EP1633761B1 (de) |
| JP (1) | JP4510011B2 (de) |
| CN (1) | CN100448882C (de) |
| AT (1) | ATE394406T1 (de) |
| DE (1) | DE602004013583D1 (de) |
| ES (1) | ES2305834T3 (de) |
| FR (1) | FR2856402B1 (de) |
| WO (1) | WO2004113354A2 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007011158A1 (de) * | 2007-03-07 | 2008-09-11 | Wacker Chemie Ag | Iridiumkatalysiertes Herstellungsverfahren für siliciumorganische Verbindungen |
| JP5455937B2 (ja) * | 2008-03-06 | 2014-03-26 | ダウ・コーニング・コーポレイション | ハロアルキルアルコキシシランおよびハロアルキルハロシランの製造方法 |
| CN108291030B (zh) | 2015-12-07 | 2021-01-05 | 美国陶氏有机硅公司 | 使用铱络合物催化剂氢化硅烷化羧酸烷基酯和氢封端的有机硅氧烷寡聚物的方法和组合物 |
| WO2017154846A1 (ja) * | 2016-03-09 | 2017-09-14 | 国立研究開発法人産業技術総合研究所 | イリジウム錯体等を用いたアリル化合物のヒドロシリル化によるシリル化合物の製造方法 |
| JP7252142B2 (ja) | 2017-06-26 | 2023-04-04 | ダウ シリコーンズ コーポレーション | 脂肪族不飽和アルコキシシラン及び水素末端オルガノシロキサンオリゴマーをヒドロシリル化して、イリジウム触媒を使用してポリオルガノシロキサンを官能化するのに有用なアルコキシシリル末端ポリマーを調製する方法 |
| US10723843B2 (en) * | 2017-07-20 | 2020-07-28 | Dow Silicones Corporation | Process for preparing platinum organosiloxane complexes using an enone additive |
| WO2019040383A1 (en) | 2017-08-22 | 2019-02-28 | Dow Silicones Corporation | DOUBLE CURING ADHESIVE COMPOSITION AND METHODS OF PREPARATION AND USE |
| CN110577485B (zh) * | 2018-06-11 | 2022-11-04 | 武汉大学 | 一种降樟脑衍生的[2,2,1]-桥环烯酮类化合物及其合成方法和应用 |
| JP2021178786A (ja) * | 2020-05-13 | 2021-11-18 | 信越化学工業株式会社 | ジメチルクロロシラン化合物の製造方法 |
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- 2004-06-16 JP JP2006516295A patent/JP4510011B2/ja not_active Expired - Fee Related
- 2004-06-16 WO PCT/FR2004/001487 patent/WO2004113354A2/fr active IP Right Grant
- 2004-06-16 EP EP04767350A patent/EP1633761B1/de not_active Not-in-force
- 2004-06-16 ES ES04767350T patent/ES2305834T3/es active Active
- 2004-06-16 US US10/561,223 patent/US20070185344A1/en not_active Abandoned
- 2004-06-16 DE DE602004013583T patent/DE602004013583D1/de active Active
- 2004-06-16 CN CNB200480019676XA patent/CN100448882C/zh not_active Expired - Fee Related
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2008
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| US5449802A (en) * | 1994-12-27 | 1995-09-12 | Dow Corning Corporation | Acetylenic alcohols and ethers as accelerators for hydrosilation |
| US5481016A (en) * | 1995-04-17 | 1996-01-02 | Dow Corning Corporation | Alcohols and silated alcohols as accelerators for hydrosilation |
| US5486637A (en) * | 1995-04-17 | 1996-01-23 | Dow Corning Corporation | Unsaturated alcohols as accelerators for hydrosilation |
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Also Published As
| Publication number | Publication date |
|---|---|
| US20080275264A1 (en) | 2008-11-06 |
| US7884225B2 (en) | 2011-02-08 |
| DE602004013583D1 (de) | 2008-06-19 |
| ES2305834T3 (es) | 2008-11-01 |
| EP1633761A2 (de) | 2006-03-15 |
| ATE394406T1 (de) | 2008-05-15 |
| JP2006527742A (ja) | 2006-12-07 |
| CN1820013A (zh) | 2006-08-16 |
| FR2856402B1 (fr) | 2005-08-26 |
| CN100448882C (zh) | 2009-01-07 |
| EP1633761B1 (de) | 2008-05-07 |
| WO2004113354A2 (fr) | 2004-12-29 |
| WO2004113354A3 (fr) | 2005-03-17 |
| FR2856402A1 (fr) | 2004-12-24 |
| JP4510011B2 (ja) | 2010-07-21 |
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