WO2004113354A2 - Procede de preparation d'halogenoalkyldialkyl-chlorosilane - Google Patents
Procede de preparation d'halogenoalkyldialkyl-chlorosilane Download PDFInfo
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- WO2004113354A2 WO2004113354A2 PCT/FR2004/001487 FR2004001487W WO2004113354A2 WO 2004113354 A2 WO2004113354 A2 WO 2004113354A2 FR 2004001487 W FR2004001487 W FR 2004001487W WO 2004113354 A2 WO2004113354 A2 WO 2004113354A2
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 22
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012429 reaction media Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 150000002576 ketones Chemical class 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 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
- 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
- BJLJNLUARMMMLW-UHFFFAOYSA-N chloro-(3-chloropropyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCl BJLJNLUARMMMLW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 34
- 239000003446 ligand Substances 0.000 claims description 23
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 229910000077 silane Inorganic materials 0.000 claims description 11
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 9
- -1 alkene halide Chemical class 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 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
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 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
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-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
- 125000004429 atom Chemical group 0.000 claims description 3
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 3
- VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 claims description 2
- 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
- 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
- UPGHEUSRLZSXAE-UHFFFAOYSA-N 2-prop-2-enylcyclohexan-1-one Chemical compound C=CCC1CCCCC1=O UPGHEUSRLZSXAE-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- WUMMIJWEUDHZCL-UHFFFAOYSA-N 3-prop-2-enyloxolane-2,5-dione Chemical compound C=CCC1CC(=O)OC1=O WUMMIJWEUDHZCL-UHFFFAOYSA-N 0.000 claims 1
- 229950000688 phenothiazine Drugs 0.000 claims 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 abstract description 13
- 239000000654 additive Substances 0.000 abstract 4
- 230000000996 additive effect Effects 0.000 abstract 4
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000006884 silylation reaction Methods 0.000 abstract 1
- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 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 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- FNOOZJAPZFHNCW-UHFFFAOYSA-N 2-methylidenebicyclo[2.2.1]heptan-3-one Chemical compound C1CC2C(=O)C(=C)C1C2 FNOOZJAPZFHNCW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MDWJXLWTUKQCNA-UHFFFAOYSA-N C(C1=CC=CC=C1)=C1C=CC2=NC3=CC=CC=C3SC2=C1 Chemical compound C(C1=CC=CC=C1)=C1C=CC2=NC3=CC=CC=C3SC2=C1 MDWJXLWTUKQCNA-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- MOHYGSBMXIJZBJ-UHFFFAOYSA-N [Ir+4] Chemical class [Ir+4] MOHYGSBMXIJZBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000013529 heat transfer fluid Substances 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000009466 transformation Effects 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 haloalkyldialkylhalogenosilane.
- the present invention relates to a process for the preparation of 3-halopropyldimethylchlorosilane, by hydrosilylation of dimethylhydrogenochlorosilane by means of allyl chloride and of a catalyst based on a platinum metal, in particular iridium, and possible recovery of said metal.
- Another way of improving the economy of the process would be to optimize the activity of the catalyst. To do this, ensure that the conversion rate (TT) of the hydrogenosilane (II) is increased or that, for a given TT, the selectivity (S) of the catalyst is significantly increased.
- transformation rate (TT) and selectivity (S) meet the following definitions: number of moles of SiH units consumed
- BE-B-785343 (US-B-3 798 252) describes the hydrosilylation of allyl chloride with trichlorohydrogensosilane, in the presence of chloroplatinic acid in solution in cyclohexanone (elimination of water in this solution in l using Na 2 SO).
- the ketone is combined with platinum to improve the selectivity of the reaction.
- one of the essential objectives of the present invention is to propose a means making it possible to optimize the activity of the iridium-based catalyst compared to what is taught in the prior art [in particular
- Another essential objective of the invention is to provide a process for the preparation of a haloalkyldialkylhalosilane of the above type, which is efficient, economical and easy to implement.
- reaction medium comprising:
- Hal represents a halogen atom chosen from chlorine, bromine and iodine atoms
- R 2 and R 3 identical or different, each represent a monovalent hydrocarbon group chosen from an alkyl radical, linear or branched, having from 1 to 6 carbon atoms and a phenyl radical
- CHI unsaturated hydrocarbon compounds having an aromatic character and / or comprising at least one carbon ⁇ carbon double bond and / or at least one C ⁇ C triple bond, these unsaturated bonds being able to be conjugated or unconjugated
- said CHI being linear or cyclic (mono or polycyclic), having from 4 to 30 carbon atoms, having from 1 to 8 ethylenic and / or acetylenic unsaturations and possibly comprising one or more heteroatoms,> (vi) and their mixtures, with the condition that when the auxiliary comprises one or more CHI as defined above, then this (these) CHI is (are ) mixed with at least one other auxiliary other than a CHI.
- mixtures (vi) in particular means auxiliary compounds: o (vi.1). any mixture of compounds (i) and / or (ii) and / or (iii) and / or (iv) and / or
- any compound whose molecule comprises at least two different chemical functions and selected from the group comprising the functions: ketone, ether, anhydride, quinone, C C, and CC, characteristics of compounds (i) to (v), o (vi .3) any mixture of compounds (vi.2), o (vi.4) as well as any mixture based on at least one compound (i) to (v) and at least one compound (vi.2) .
- an iridium-based catalyst of oxidation state I is used, in the structure of which each iridium atom responds to the complex form of the Ir (L) 3 X type where the symbols L and X have the definitions given in the book "Organometallic Chemistry of Didier ASTRUC", published in 2000 by EDP Sciences (cf. notably on page 31 and following).
- the catalyst corresponds to formula (IV):
- Catalysts corresponding to the above-mentioned more preferred definition are well suited in which:
- - R 4 is a ligand comprising at least one carbon ⁇ carbon double bond and / or at least one C ⁇ C triple bond, these unsaturated bonds being able to be conjugated or unconjugated, said ligand: being linear or cyclic (mono or polycyclic), having from 4 to 30 carbon atoms, having from 1 to 8 ethylenic and / or acetylenic unsaturations and optionally comprising one or more heteroatoms, and - R 5 , in addition to Hal, may also represent an LX ligand such as in particular a ligand derived from acetylacetone, a ⁇ -ketoester, a malonic ester, an allylated compound.
- LX ligand such as in particular a ligand derived from acetylacetone, a ⁇ -ketoester, a malonic ester, an allylated compound.
- the ligands R 4 of the preferred catalyst (IV) may be identical or different from the CHI (v) of the auxiliary.
- the iridium-based catalyst can be supported as described for example in US-B-6,177,585 and GB-A-1526324
- the catalytic system used in accordance with the process according to the invention makes it possible to reduce the quantity of catalyst necessary for obtaining a complete TT conversion rate 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 TT.
- auxiliaries can be used in liquid or solid form. As soon as they are liquid, they can be introduced in such a quantity into the reaction medium that they play, in addition to a role of hydrosilylation promoter, a role of solvent for the reaction.
- the optional solvent function 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 higher than that of the compound of formula (I), for example a polyether), to improve the stability of the medium reaction and therefore the safety of the process. In addition, this offers possibilities of easy recovery of the catalyst and therefore recycling of the latter.
- a heavy solvent namely a solvent having a boiling point at atmospheric pressure which is higher than that of the compound of formula (I), for example a polyether
- the auxiliary When the auxiliary is in the free state, it can be introduced into the reaction medium in a molar ratio, relative to the iridium metal, of at least 0.2, preferably at least 1. According to the nature of the ligands, it is more preferable to choose a molar ratio greater than 10 and even greater than 100.
- the concentration of catalyst (preferably IV) is such that the molar ratio
- Iridium / silane of formula (II), expressed in moles, is less than or equal to 400.10, preferably 200.10, and more preferably still 50.10 "6 .
- ketones (i) reference can be made to those defined in US-B-3 798 252 and in PL-A-176036, PL-A-174810, PL-A-145670 and JP-A -75,024,947.
- Suitable ethers (ii) reference may be made to those defined in US-B-4,820,674 and in JP-A-52093718.
- the auxiliary is selected from the group comprising in particular: cyclohexanone, 2-cyclohexen-1-one, isophorone, 2-benzylidenecyclohexanone, 3-Methylene-2-norbornanone, 4-hexen-3-one, 2-allylcyclohexanone, 2 -Oxo-1- cyclohexaneproprionitrile, 2- (1-cyclohexenyl) cyclohexanone, monoglyme, ethylene-glycoldivinyl ether, ethyl ether, benzoquinone, phenyl-benzoquinone, maleic anhydride, allylated succinic anhydride, 3-benzylidene phenothiazine, (methylvinyl) cyclotetrasiloxane (vinylated D4), 4-phenyl-3-butyn-2- one, butadiene-1, 3, hexadiene-1, 5, cyclohexadiene
- the auxiliary is a mixture (vi) comprising at least one CHI (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 molar ratio of formula (II), expressed in moles, is lower or equal to 100.10, preferably 60.10, and even more preferably is between 40.10 "6 and 1.10 " 6 .
- the components of the mixture (vi): CHI / (i) and / or (ii) and / or (iii) are present in the reaction medium when the reaction starts.
- iridium (IV) complexes which are even more suitable, the following catalysts may be mentioned: d - ⁇ -chlorobis ( ⁇ -1, 5-hexadiene) diiridium, d - ⁇ -bromobis ( ⁇ - 1, 5-hexadiene) diiridium, d - ⁇ -iodobis ( ⁇ -1, 5-hexadiene) diiridium, d - ⁇ -chlorobis ( ⁇ -1, 5-cyclooctadiene) diiridium, d - ⁇ -bromobis ( ⁇ -1, 5-cyclooctadiene) diiridium, d - ⁇ -iodobis ( ⁇ -1, 5-cyclooctadiene) diiridium, d - ⁇ -chlorobis ( ⁇ -2,5-norbomadiene) diiridium, d - ⁇ -bromobis ( ⁇ -2,5- norbornadiene) diiridium, d - ⁇ -chlor
- the method according to the invention can be implemented either continuously, or semi-continuously, or discontinuously.
- the catalyst - preferably IV - is used in a homogeneous liquid medium, according to a preferred arrangement of the invention and as described in JP-B-2 938 731 and EP-A-1 156 052.
- the product of formula (I) is 3-chloropropyl-dimethylchlorosilane
- the product of formula (II) is dimethylhydrogenochlorosilane
- the product of formula (III) is allyl chloride.
- the invention relates to a catalytic system for the preparation of a haloalkyldialkyl-halogenosilane of formula (I):
- CH CH- (CH 2 ) s-2 Hal formulas in which: - the symbol Hal represents a halogen atom chosen from chlorine, bromine and iodine atoms,
- R 2 and R 3 identical or different, each represent a monovalent hydrocarbon group chosen from an alkyl radical, linear or branched, having from 1 to 6 carbon atoms and a phenyl radical, and - s represents an integer included between 2 and 10 inclusive,
- CHI unsaturated hydrocarbon compounds
- said CHI being linear or cyclic (mono or polycyclic), having from 4 to 30 carbon atoms, having from 1 to 8 ethylenic and / or acetylenic unsaturations and optionally comprising one or more heteroatoms, vi) and their mixtures,
- this (these) CHI is (are) mixed with at least one other auxiliary different from a CHI.
- the tests are carried out in parallel reactors.
- Each reactor is equipped with a magnetic stirrer, a reflux condenser and a thermometer.
- the heat transfer fluid is brought to a temperature of -35 ° C, which makes it possible to obtain a material balance always greater than 95% by mass.
- the effect of the hydrosilylation auxiliaries is compared to a control reaction where only di- ⁇ -chlorobis ( ⁇ -1, 5-cyclooctadiene) diiridium was used.
- a deliberately small amount of catalyst was introduced in order to obtain a conversion rate of the SiH functions of the order of 50%.
- Dimethylhydrogenochlorosilane of purity 99% by weight, is added by casting on a foot heated to 35 ° C and consisting of allyl chloride (1.05 eq. Mol / silane) as well as the catalytic system
- silane is poured through a syringe pump at a flow rate of 1.3 ml / minute.
- the temperature of the reaction medium is not regulated.
- reaction medium The analysis of the reaction medium is carried out by gas phase chromatography calibrated with n-tetradecane.
- Dimethylhydrogenochlorosilane purity 99% by weight is introduced by a peristaltic pump into the reaction medium.
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- 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)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602004013583T DE602004013583D1 (de) | 2003-06-17 | 2004-06-16 | Verfahren zur herstellung von halogenalkyldialkylchlorsilan |
EP04767350A EP1633761B1 (fr) | 2003-06-17 | 2004-06-16 | Procede de preparation d' halogenoalkyldialkyl-chlorosilane |
US10/561,223 US20070185344A1 (en) | 2003-06-17 | 2004-06-16 | Method of preparing halogenoalkyldialkyl chlorosilane |
JP2006516295A JP4510011B2 (ja) | 2003-06-17 | 2004-06-16 | ハロアルキルジアルキルクロルシランの製造方法 |
US12/173,968 US7884225B2 (en) | 2003-06-17 | 2008-07-16 | Process for the preparation of halogenoalkyldialkyl chlorosilane |
Applications Claiming Priority (2)
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 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/561,223 A-371-Of-International US20070185344A1 (en) | 2003-06-17 | 2004-06-16 | Method of preparing halogenoalkyldialkyl chlorosilane |
US12/173,968 Continuation US7884225B2 (en) | 2003-06-17 | 2008-07-16 | Process for the preparation of halogenoalkyldialkyl chlorosilane |
Publications (2)
Publication Number | Publication Date |
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WO2004113354A2 true WO2004113354A2 (fr) | 2004-12-29 |
WO2004113354A3 WO2004113354A3 (fr) | 2005-03-17 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/FR2004/001487 WO2004113354A2 (fr) | 2003-06-17 | 2004-06-16 | Procede de preparation d'halogenoalkyldialkyl-chlorosilane |
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US (2) | US20070185344A1 (fr) |
EP (1) | EP1633761B1 (fr) |
JP (1) | JP4510011B2 (fr) |
CN (1) | CN100448882C (fr) |
AT (1) | ATE394406T1 (fr) |
DE (1) | DE602004013583D1 (fr) |
ES (1) | ES2305834T3 (fr) |
FR (1) | FR2856402B1 (fr) |
WO (1) | WO2004113354A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8580994B2 (en) | 2008-03-06 | 2013-11-12 | Dow Corning Corporation | Process for the preparation of haloalkylalkoxysilanes and haloalkylhalosilanes |
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---|---|---|---|---|
DE102007011158A1 (de) * | 2007-03-07 | 2008-09-11 | Wacker Chemie Ag | Iridiumkatalysiertes Herstellungsverfahren für siliciumorganische Verbindungen |
US10280265B2 (en) | 2015-12-07 | 2019-05-07 | Dow Corning Corporation | Method and composition for hydrosilylation of carboxylic acid alkenyl esters and hydrogen terminated organosiloxane oligomers with an iridium complex catalyst |
WO2017154846A1 (fr) * | 2016-03-09 | 2017-09-14 | 国立研究開発法人産業技術総合研究所 | Procédé de production d'un composé silyle par hydrosilylation d'un composé allylique à l'aide d'un complexe d'iridium ou similaire |
EP3645607A1 (fr) | 2017-06-26 | 2020-05-06 | Dow Silicones Corporation | Procédé d'hydrosilylation d'alcoxysilanes aliphatiquement insaturés et d'oligomères d'organosiloxane à terminaison hydrogène pour préparer des polymères à terminaison alcoxysilyle utiles pour fonctionnaliser des polyorganosiloxanes à l'aide d'un catalyseur à l'iridium |
JP6929457B2 (ja) * | 2017-07-20 | 2021-09-01 | ダウ シリコーンズ コーポレーション | エノン添加剤を使用した白金オルガノシロキサン錯体を調製するためのプロセス |
WO2019040383A1 (fr) | 2017-08-22 | 2019-02-28 | Dow Silicones Corporation | Composition adhésive à double durcissement et ses procédés de préparation et d'utilisation |
CN114940661B (zh) * | 2018-06-11 | 2023-12-22 | 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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EP0709390A1 (fr) * | 1994-10-27 | 1996-05-01 | Dow Corning Corporation | Cétones insaturées comme accélérateur d'hydrosilylation |
EP0722947A1 (fr) * | 1994-12-27 | 1996-07-24 | Dow Corning Corporation | Alcools et éthers acétyléniques comme accélérateurs pour hydrosilylation |
EP0738731A2 (fr) * | 1995-04-17 | 1996-10-23 | Dow Corning Corporation | Alcools et alcools silylé comme accélérateur pour l'hydrosilylation |
EP0738730A2 (fr) * | 1995-04-17 | 1996-10-23 | Dow Corning Corporation | Alcools insaturés comme accélérateurs pour l'hydrosilylation |
EP0751140A2 (fr) * | 1995-06-26 | 1997-01-02 | Dow Corning Corporation | Ene-yne composés insaturés comme accélérateurs dans le procédé d'hydrosililation |
EP0786465A1 (fr) * | 1996-01-29 | 1997-07-30 | Dow Corning Corporation | Aldéhyde comme promoteurs de réactions d'hydrosilylation |
EP0850943A2 (fr) * | 1996-12-30 | 1998-07-01 | Dow Corning Corporation | Procédé d'hydrosililationa vec des accélérateurs insaturés |
EP1156052A2 (fr) * | 2000-05-15 | 2001-11-21 | Shin-Etsu Chemical Co., Ltd. | Procédé de préparation de halopropyldiméthylchlorosilanes |
DE10053037C1 (de) * | 2000-10-26 | 2002-01-17 | Consortium Elektrochem Ind | Herstellung von Organosilanen |
DE10232663C1 (de) * | 2002-07-18 | 2003-10-16 | Wacker Chemie Gmbh | Kontinuierliche Herstellung von Organosilanen |
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JP2938731B2 (ja) * | 1993-10-28 | 1999-08-25 | 信越化学工業株式会社 | ハロプロピルジメチルクロロシランの製造方法およびその合成用の触媒 |
US5756796A (en) * | 1997-05-19 | 1998-05-26 | Dow Corning Corporation | Method for preparation of alkenylsilanes |
US6500977B1 (en) * | 2001-11-27 | 2002-12-31 | Dow Corning Corporation | Process for producing organosilanes |
FR2833265B1 (fr) * | 2001-12-06 | 2006-02-10 | Rhodia Chimie Sa | Procede d'obtention de monoorganoxysilane polysulfures |
FR2843392B1 (fr) * | 2002-08-09 | 2004-09-10 | Rhodia Chimie Sa | Procede de preparation d'halogenoalkyldialkylchlorosilane |
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2003
- 2003-06-17 FR FR0350222A patent/FR2856402B1/fr not_active Expired - Fee Related
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2004
- 2004-06-16 JP JP2006516295A patent/JP4510011B2/ja not_active Expired - Fee Related
- 2004-06-16 AT AT04767350T patent/ATE394406T1/de not_active IP Right Cessation
- 2004-06-16 DE DE602004013583T patent/DE602004013583D1/de not_active Expired - Lifetime
- 2004-06-16 CN CNB200480019676XA patent/CN100448882C/zh 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/fr not_active Expired - Lifetime
- 2004-06-16 US US10/561,223 patent/US20070185344A1/en not_active Abandoned
- 2004-06-16 ES ES04767350T patent/ES2305834T3/es not_active Expired - Lifetime
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2008
- 2008-07-16 US US12/173,968 patent/US7884225B2/en not_active Expired - Fee Related
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0709390A1 (fr) * | 1994-10-27 | 1996-05-01 | Dow Corning Corporation | Cétones insaturées comme accélérateur d'hydrosilylation |
EP0722947A1 (fr) * | 1994-12-27 | 1996-07-24 | Dow Corning Corporation | Alcools et éthers acétyléniques comme accélérateurs pour hydrosilylation |
EP0738731A2 (fr) * | 1995-04-17 | 1996-10-23 | Dow Corning Corporation | Alcools et alcools silylé comme accélérateur pour l'hydrosilylation |
EP0738730A2 (fr) * | 1995-04-17 | 1996-10-23 | Dow Corning Corporation | Alcools insaturés comme accélérateurs pour l'hydrosilylation |
EP0751140A2 (fr) * | 1995-06-26 | 1997-01-02 | Dow Corning Corporation | Ene-yne composés insaturés comme accélérateurs dans le procédé d'hydrosililation |
EP0786465A1 (fr) * | 1996-01-29 | 1997-07-30 | Dow Corning Corporation | Aldéhyde comme promoteurs de réactions d'hydrosilylation |
EP0850943A2 (fr) * | 1996-12-30 | 1998-07-01 | Dow Corning Corporation | Procédé d'hydrosililationa vec des accélérateurs insaturés |
EP1156052A2 (fr) * | 2000-05-15 | 2001-11-21 | Shin-Etsu Chemical Co., Ltd. | Procédé de préparation de halopropyldiméthylchlorosilanes |
DE10053037C1 (de) * | 2000-10-26 | 2002-01-17 | Consortium Elektrochem Ind | Herstellung von Organosilanen |
DE10232663C1 (de) * | 2002-07-18 | 2003-10-16 | Wacker Chemie Gmbh | Kontinuierliche Herstellung von Organosilanen |
WO2004009607A1 (fr) * | 2002-07-18 | 2004-01-29 | Wacker-Chemie Gmbh | Production continue d'organosilanes |
Cited By (1)
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US8580994B2 (en) | 2008-03-06 | 2013-11-12 | Dow Corning Corporation | Process for the preparation of haloalkylalkoxysilanes and haloalkylhalosilanes |
Also Published As
Publication number | Publication date |
---|---|
US20070185344A1 (en) | 2007-08-09 |
DE602004013583D1 (de) | 2008-06-19 |
FR2856402A1 (fr) | 2004-12-24 |
ATE394406T1 (de) | 2008-05-15 |
EP1633761B1 (fr) | 2008-05-07 |
JP4510011B2 (ja) | 2010-07-21 |
CN100448882C (zh) | 2009-01-07 |
EP1633761A2 (fr) | 2006-03-15 |
JP2006527742A (ja) | 2006-12-07 |
US20080275264A1 (en) | 2008-11-06 |
WO2004113354A3 (fr) | 2005-03-17 |
US7884225B2 (en) | 2011-02-08 |
ES2305834T3 (es) | 2008-11-01 |
FR2856402B1 (fr) | 2005-08-26 |
CN1820013A (zh) | 2006-08-16 |
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