EP2097425A2 - Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylen - Google Patents
Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylenInfo
- 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
- Authority
- EP
- European Patent Office
- Prior art keywords
- iii
- group
- reaction
- solvent
- θebsl
- 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.)
- Withdrawn
Links
- 125000003342 alkenyl group Chemical group 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 150000004756 silanes Chemical class 0.000 title abstract description 20
- 125000000962 organic group Chemical group 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 claims abstract description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 44
- -1 halide compound Chemical class 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 51
- 239000012429 reaction media Substances 0.000 claims description 43
- 239000011777 magnesium Substances 0.000 claims description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 28
- 239000002184 metal Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- 238000009835 boiling Methods 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 20
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 19
- 150000002894 organic compounds Chemical class 0.000 claims description 19
- 150000003254 radicals Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052749 magnesium Inorganic materials 0.000 claims description 16
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 13
- 229910000077 silane Inorganic materials 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 230000000750 progressive effect Effects 0.000 claims description 3
- 238000005063 solubilization Methods 0.000 claims description 3
- 230000007928 solubilization Effects 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229910009257 Y—Si Inorganic materials 0.000 claims description 2
- 150000001241 acetals Chemical class 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 150000002012 dioxanes Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000002608 ionic liquid Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 9
- 239000007858 starting material Substances 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000008569 process Effects 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 12
- FEIZMBLMTCAJSQ-UHFFFAOYSA-N ethoxy-dimethyl-prop-2-enylsilane Chemical compound CCO[Si](C)(C)CC=C FEIZMBLMTCAJSQ-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000007514 turning Methods 0.000 description 8
- 239000007818 Grignard reagent Substances 0.000 description 7
- 150000004795 grignard reagents Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001994 activation Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000002901 organomagnesium compounds Chemical class 0.000 description 5
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002734 organomagnesium group Chemical group 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 238000007184 Barbier reaction Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003344 environmental pollutant Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 231100000719 pollutant Toxicity 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- BUHVMRGRQGNLIW-UHFFFAOYSA-N CCO[SiH](CC=CC)OCC Chemical compound CCO[SiH](CC=CC)OCC BUHVMRGRQGNLIW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005937 allylation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- DNAJDTIOMGISDS-UHFFFAOYSA-N prop-2-enylsilane Chemical compound [SiH3]CC=C DNAJDTIOMGISDS-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000005372 silanol group Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 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
- C07F7/18—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 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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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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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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EP07822451A Withdrawn EP2097425A2 (de) | 2006-11-10 | 2007-11-09 | Verfahren zur herstellung funktionalisierter organomonoalkoxy- (oder monohydroxy-)silane, insbesondere alkenylen |
Country Status (4)
Country | Link |
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US (1) | US20100140541A1 (de) |
EP (1) | EP2097425A2 (de) |
FR (1) | FR2908412B1 (de) |
WO (1) | WO2008055984A2 (de) |
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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 |
Family Cites Families (8)
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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 |
-
2006
- 2006-11-10 FR FR0609839A patent/FR2908412B1/fr not_active Expired - Fee Related
-
2007
- 2007-11-09 EP EP07822451A patent/EP2097425A2/de not_active Withdrawn
- 2007-11-09 WO PCT/EP2007/062163 patent/WO2008055984A2/fr active Application Filing
- 2007-11-09 US US12/514,251 patent/US20100140541A1/en not_active Abandoned
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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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