EP2049553A1 - Procédé de production de composés organosilicium par hydrosilylation de liquides ioniques - Google Patents
Procédé de production de composés organosilicium par hydrosilylation de liquides ioniquesInfo
- Publication number
- EP2049553A1 EP2049553A1 EP07765548A EP07765548A EP2049553A1 EP 2049553 A1 EP2049553 A1 EP 2049553A1 EP 07765548 A EP07765548 A EP 07765548A EP 07765548 A EP07765548 A EP 07765548A EP 2049553 A1 EP2049553 A1 EP 2049553A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- reaction
- catalyst
- hydrosilylation
- ionic
- 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- Withdrawn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
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 58
- 238000006459 hydrosilylation reaction Methods 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000003961 organosilicon compounds Chemical class 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 73
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 13
- 150000003624 transition metals Chemical class 0.000 claims abstract description 13
- 150000004756 silanes Chemical class 0.000 claims abstract description 8
- -1 3, 5-bis- (trifluoromethyl) -phenyl Chemical group 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 36
- 239000012071 phase Substances 0.000 claims description 26
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 238000005191 phase separation Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 4
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 claims description 2
- 238000010574 gas phase reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 229910018540 Si C Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229910010271 silicon carbide Inorganic materials 0.000 claims 1
- 239000000376 reactant Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 18
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 15
- 239000005052 trichlorosilane Substances 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 230000001681 protective effect Effects 0.000 description 12
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- WMFFUNWLTYCMTH-UHFFFAOYSA-N manganese silane Chemical class [SiH4].[Mn] WMFFUNWLTYCMTH-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 3
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229940069096 dodecene Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 150000001367 organochlorosilanes Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical class C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical class C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 238000005913 hydroamination reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006464 oxidative addition reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000005053 propyltrichlorosilane Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001425 triazolyl group Chemical class 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
- C07F7/0829—Hydrosilylation reactions
-
- 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 invention relates to a process for the preparation of organosilicon compounds by hydrosilylation in ionic liquids.
- organosilicon compounds are carried out according to the prior art after the Muller-Rochow synthesis.
- the functionalized organosilanes are of great economic importance, in particular halogen-substituted ones, since they serve as starting materials for the preparation of many important products, for example silicones, adhesion promoters, water repellents and building protection agents.
- One way to prepare manganese silanes is to convert easily prepared silanes (excess silanes) to manganese silanes by a ligand exchange reaction.
- ionic liquids in the two-phase system for ligand exchange of organochlorosilanes with other organochlorosilanes and is described for example in the patent DE 101 57 198 Al.
- a ligand exchange reaction takes place on the silicon atom, in which an organosilane in the presence of an ionic liquid, which is a halide,
- Metal or transition metal halide of organic nitrogen or phosphorus compounds, disproportionated or with another organosilane is reacted under ligand exchange.
- Ionic liquids are generally understood to mean salts or mixtures of salts whose melting points are below 100 ° C., as described, for example, in P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926.
- Literature-known salts of this type consist of anions such as halogenostannates, halogenoaluminates, hexafluorophosphates, tetrafluoroborates, alkyl sulfates, alkyl or aryl sulfonates, dialkyl phosphates, rhodanides or dicyanamides combined with substituted ammonium, phosphonium, imidazolium, pyridinium, pyrazolium, triazolium, picolinium - or pyrrolidinium cations.
- Numerous publications already describe the use of ionic liquids as solvents for
- Transition metal catalyzed reactions such as T. Welton, Chem. Rev. 1999, 99, 2071, and P. Wasserscheid, W. Keim, Angew. Chem., 2000, 112, 3926, and P. Wasserscheid, T. Welton (Eds.) &Quot; Ionic Liquids in Synthesis ", 2003, Wiley-VCH, Weinheim, pp 213-257
- Improvements are also of considerable technical relevance and occur, for example, in a significantly improved catalyst removability and catalyst reuse, a significantly increased catalyst stability, a significantly increased reactivity or a significantly improved
- ionic liquids offer the possibility of a gradual coordination of relevant structural variations Solvent properties towards a specific application goal.
- the hydrosilylation of 1-alkenes is known to be catalyzed by platinum group metal complexes as described, for example, in J. Marciniec, "Comprehensive Handbook on Hydrosilylation", Pergamon Press, New York 1992.
- platinum complexes such as the so-called “Speier catalyst” [H 2 PtCl 6 * 6 H 2 O] and the "Karstedt solution", a complex compound of [H 2 PtCl 6 * 6 H 2 O] and vinyl-substituted disiloxanes, are known to be very active catalysts in that with the use of some anhydrous platinum compounds, for example dicycloocadienylplatinum ([Pt (cod) 2 ]), platinum colloids are formed, which are also highly active hydrosilylation catalysts as described, for example, in LN Lewis, N. Lewis, J. Am. Chem Soc., 1986, 108, 7728.
- Performing the hydrosilylation reaction as a liquid-liquid two-phase reaction requires a system with a polar and a nonpolar solvent in which both solvents have a miscibility gap.
- the systems cyclohexane / propene were published as nonpolar and cyclohexane / propylene carbonate as the polar phase in A. Behr, N. Toslu, Chem. Eng. Technol. 2000, 23, 2.
- this system for example, the hydrosilylation of ⁇ -undecenoic acid with triethoxysilane, where the product is enriched in the non-polar phase and can be easily separated from the catalyst and the starting materials which remain in the polar phase.
- SILP supported ionic liquid phase
- SILP catalyst technology the solution of a transition metal complex in an ionic liquid is applied to a mostly highly porous carrier, by physisorption or chemical reaction, and the resulting solid catalyst is contacted with the reactants in a gas phase or liquid phase reaction.
- This technology represents a new approach to combining the advantages of classical homogeneous catalysis with those of classical heterogeneous catalysis.
- Catalyst solution on a porous solid it is achieved that without high input of mechanical energy to the reactants a high specific surface of ionic catalyst solution is ready for reaction.
- the catalyst is still homogeneous dissolved here.
- the technology also provides very easy access to continuous processes, for example, in A. Riisager, P. Wasserscheid, R. van HaI, R. Fehrmann, J. Catal. 2003, 219, 252.
- SILP technology Interactions of the active surface groups of the porous support with the transition metal catalyst in only a few nanometers thick carrier film, the successful use of SILP technology for the skilled person not obvious.
- Other known applications of SILP technology include
- the object of the invention was therefore to provide a process for the preparation of silanes by hydrosilylation, which proceeds very selectively and thus leads to high yields of the desired silanes.
- This object has been achieved by the process according to the invention for the preparation of silanes by hydrosilylation, which is characterized in that the catalyst used for the hydrosilylation reaction is a transition metal complex compound which is dissolved in an ionic liquid during the reaction.
- An advantage of the novel process according to this invention is the technical possibility of catalyst separation and recirculation in the liquid-liquid multiphase system or in variants in which the ionic catalyst solution is applied to solids.
- a achieved significant selectivity improvement in silane synthesis in many cases compared to the known synthesis method a achieved significant selectivity improvement in silane synthesis.
- R is independently a H, a monovalent Si-C-bonded, optionally halogen-substituted C] _-C] _g-
- R 8 , R 9 , R 10 and R 11 are independently H, a monovalent optionally with F , Cl, OR, NR 2, CN or NCO substituted C] _C] _g hydrocarbon, chlorine, fluorine or C] _- C] _g alkoxy radical, wherein in each case 2 radicals of R 8 , R 9 , R 10 and R 11 together with the carbon atoms to which they are attached can form a cyclic radical.
- those of the general formula (3) are preferably reacted as non-polymeric compounds
- R carries the meaning given above, and c the values 0, 1, 2, 3 or 4 and d can have the values 1, 2 or 3.
- Such a superposition of hydrosilylation, disportportionation, and ligand exchange reaction should thus technically facilitate the preparative use of hydrosilylation of non-polymeric compounds bearing one or more H-Si functionality (s) with unsaturated compounds using ionic catalyst solutions in the liquid-liquid multiphase system to make something useless.
- Formula (1) which carry one or more H-Si functionality (s), is preferably carried out with such alkenes, in addition to Carbon and hydrogen may still contain chlorine, alkoxy or amino functionalities.
- the instant process of this invention demonstrates an unexpected technical solution based on the discovery that the solution of a transition metal complex used as a hydrosilylation catalyst in an ionic liquid surprisingly catalyzes selectively a hydrosilylation of non-polymeric Si-H compounds in a multi-phase reaction regime.
- the process according to this invention also offers a technically reliable possibility of catalyst separation and recirculation in the liquid-liquid two-phase system. With multiple recirculation of the ionic liquid, only slight changes in the activity and selectivity of the ionic catalyst solution are observed. In the preferred variants of the method according to the invention which are shown below, the changes are particularly slight.
- Si-H compounds according to the Formula (3) are as Si-H compounds according to the Formula (3) the compounds HSiCl 3 , HSiCl 2 Me, HSiClMe 2 , HSiCl 2 Et and HSiClEt 2 , HSi (OMe) 3 , HSi (OEt) 3 , HSi (OMe) 2 Me, HSi (OEt) 2 Me, HSi (OMe) Me 2 and HSi (OEt) Me 2 used.
- alkenes used are propene, allyl chloride, acetylene, ethylene, isobutylene, cyclopentene, cyclohexene and 1-hexadecene.
- HSiCl 3 and HSiMeCl 2 are used as Si-H compound and allyl chloride as alkene component.
- Platinum, iridium or rhodium used.
- [Y] - an anion is selected from the group comprising [tetrakis (3, 5-bis (trifluoromethyl) phenyl) borate], ([BARF]), tetraphenylborate ([BF 4 ] “ ), hexafluorophosphate ([PF 6 ] “ ), trispentafluoroethyltrifluorophosphate ([P (C 2 F 5 ) 3 F 3 ] " ), hexafluoroantimonate ([SbF 6 ] " ), hexafluoroarsenate ([AsF 6 ] “ ), fluorosulfonate, [R '-COO] “ , [R'-SO 3] ", [R'-O-SO 3]” [R '2 PO 4] “, or [(R' SO 2) 2 N] -, where R 'is a linear or branched aliphatic or alicyclic alkyl containing 1 to 12 carbon atoms
- radicals R 1'7 each independently represent organic radicals having 1-20 C atoms.
- the radicals R 1'7 are preferably aliphatic, cycloaliphatic, aromatic, araliphatic or oligoether groups.
- Aliphatic groups are straight-chain or branched hydrocarbon radicals having from one to twenty carbon atoms, it being possible for heteroatoms, such as, for example, oxygen, nitrogen or sulfur atoms, to be present in the chain.
- the radicals R 1'7 may be saturated or have one or more double or triple bonds which may be conjugated or isolated in the chain.
- Hydrocarbon groups having one to 14 carbon atoms for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl or n-decyl.
- cycloaliphatic groups are cyclic hydrocarbon radicals having between three and twenty carbon atoms, which may contain ring heteroatoms, such as oxygen, nitrogen or sulfur atoms.
- the cycloaliphatic groups may also be saturated or have one or more double or triple bonds which may be conjugated or isolated in the ring.
- Aromatic groups carbocyclic-aromatic groups or heterocyclic-aromatic groups can have between six and twenty-two carbon atoms. Examples of suitable aromatic groups are phenyl, naphthyl or anthracyl.
- Oligoether development are groups of the general formula (13)
- R ⁇ represents an aliphatic, cycloaliphatic, aromatic or araliphatic group.
- an ionic liquid is used whose cations [A] + can not be formed by deprotonation or oxidative addition of a C-H bond to a low-valence metal complex, metal complexes with N-heterocyclic carbene ligands.
- Particularly preferred cations of the ionic liquid used are N-alkylpyridinium and 1, 2, 3-trialkylimidazolium cations.
- the inventive method is carried out as a two-phase reaction, wherein the catalyst can be used as a liquid phase and the reaction products as a liquid or gas phase.
- Transition metal complex dissolved in the ionic liquid and contacted with a non-miscible phase in the reactor, which contains the reaction product at the reactor outlet, so that the ionic catalyst solution is separated by phase separation in the process continuously and recycled to the reactor.
- a further variant of the method consists in a Maschinenfabung such that a film of the ionic
- Catalyst solution is applied to a carrier material and the catalyst is brought into contact in this form in a gas phase reaction or in a Flussigphasenresure with the reaction mixture.
- This transfer of the known for other reactions SILP technology on the hydrosilylation of non-polymeric Si-H compounds according to formula (1) with alkenes according to formula (2) was surprisingly very successful, since this process variant, the first successful application of Pt-containing SILP Represents catalysts. It is further Surprisingly, despite the known sensitivity to water of the hydrosilylation reaction, the reaction with supported ionic catalyst solutions succeeds. The lack of deactivation of the sensitive transition metal catalyst or the possible deterioration of the product selectivity by interactions of the support with the catalyst could not be easily foreseen.
- the described method can be carried out both without pressure and under pressure.
- we carried out the process at a pressure of up to 200 bar, more preferably at a pressure of up to 20 bar.
- Example 1 Pressure-free Hydrosilylation Experiment with Ionic Liquid Using the Example of the Synthesis of 3-Chloropropyltrichlorosilane (Inventive)
- a three-necked flask (100-250 ml) is provided with dropping funnel and contact thermometer for internal temperature control and dried under high vacuum. Subsequently, 6.0 g of the product 3-chloropropyltrichlorosilane are placed under a protective gas atmosphere in the three-necked flask.
- 80 0 C external temperature control
- about 8.5 mg equivalent to 600 ppmn Pt
- the organic catalyst complex solution of PtC14 in 1-dodecene
- stirring magnetic stirrer
- All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after the addition. It is particularly important to pay attention to the correct ratio of the reactants.
- the reaction temperature of 100 ° C is set and controlled on the thermostat.
- the temperature of the intensive cooler (-20 0 C) is replaced by a
- Table 1 shows the results of Example 1 and Comparative Example 1.
- Example 2 Hydrosilylation experiment with ionic liquid under pressure (according to the invention)
- ionic liquid 1-ethyl-2,3-dimethylimidazoliumbistrifluoromethanesulphonylimide are initially introduced into a laboratory autoclave which has been dried under high vacuum and flooded with argon.
- 3.5 mg of platinum tetrachloride (equivalent to 300 ppmn) are weighed into the approximately moisture-free ionic liquid.
- the ionic catalyst solution is after the addition of the catalyst for one hour under vacuum at 100 0 C (internal temperature control) dried. Thereafter, the remaining reactants (3-
- the reactor is placed under argon under the reaction pressure of 12 bar.
- the reaction temperature of 100 ° C is set on the heating jacket and controlled internally. When the reaction temperature has been reached, the reactants are added from the dropping funnel.
- the autoclave After the end of the reaction (about 2 hours), the autoclave is carefully cooled in an ice bath to room temperature and then opened under argon flow. The contents are added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate containers. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired. The organic phase is analyzed by gas chromatography. The amount of bled in the product phase platinum is determined by ICP-AES.
- All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after the addition. It is particularly important to pay attention to the correct ratio of the reactants.
- the reactor is pressurized with argon under the system pressure of 12 bar.
- the reaction temperature 100 ° C. is set on the heating jacket and controlled internally. When the reaction temperature has been reached, the reactants are added from the dropping funnel. After the end of the reaction (about 2 hours), the autoclave is carefully cooled in an ice bath to room temperature and then opened under argon flow.
- organic phase (top) and ionic catalyst solution are separated and filled into separate containers. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
- the organic phase is analyzed by gas chromatography.
- Table 2 shows the results of Example 2 and Comparative Example 2.
- the three-necked flask is connected to the reflux condenser under constant protective gas flow and provided with a dropping funnel.
- the third port of the piston is closed with a contact thermometer for internal temperature control. If the apparatus is gas-tight, all newly connected system parts are dried in the HV. Thereafter, the remaining reactants (3-chloropropyltrichlorosilane: 5.6 g; allyl chloride 5, 6 g and
- Trichlorosilane 12.5 g
- All reactants (3-chloropropyltrichlorosilane, allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after addition into the dropping funnel.
- the reaction temperature of 100 0 C is set and controlled at the thermostat.
- the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
- the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the reaction temperature has returned to the set point. When the addition is completed, stirring is continued for 60 minutes to ensure complete conversion of the reactants.
- ionic liquid and products are cooled in an ice bath.
- the content of the three-necked flask is added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate vessels. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
- the organic phase is analyzed by gas chromatography. The amount of in the Product phase of bled platinum is determined by ICP-AES.
- the carrier material used is a silica granulate (about 5 g) with a particle size distribution of 0.2 to 0.5 mm.
- the support Before the ionic liquid is applied, the support is calcined for several hours at 450 ° C. and placed under protective gas while still hot.
- the ionic liquid 1-ethyl-3-methylimidazoliumbistrifluoromethanesulfonylimide (1.0 g) is already charged with the catalyst (PtCl 4 : 0.7 mg, corresponding to 55 ppmn) and is dissolved in a 10-fold excess of methanol.
- the carrier material is combined with the IL-methanol solution and stirred until a homogeneous distribution can be ensured.
- the methanol is carefully removed under vacuum and moderately elevated temperature (about 50 0 C).
- This SILP catalyst is then dried under constant stirring (magnetic stirrer) at 80 0 C (external temperature control) under HV for one hour.
- a 3-necked flask (100-250 ml) is equipped with dropping funnel, reflux condenser and contact thermometer for internal temperature control. Between Ruckpoundkuhler and three-necked flask here is a heated glass frit used to keep the catalyst. The entire apparatus is dried under high vacuum, including the SILP catalyst. If the apparatus is cooled, the dropping funnel is under constant inert gas stream with 6.3 g of allyl chloride and 11.7 g
- Trichlorosilane is filled. All reactants (allyl chloride and trichlorosilane) are tared for initial weighing in syringes and weighed after addition into the dropping funnel. It In this case, pay particular attention to the correct ratio of the reactants.
- the reaction temperature of 100 0 C is adjusted and regulated via the heating line of the glass frit.
- the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
- the three-necked flask serves as an evaporator of the educts and is heated with an oil bath at 100 0 C. When the reaction temperature is reached, the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the
- Reaction temperature has returned to the set point.
- the organic products are analyzed by gas chromatography. Residues of organic material adhering to the SILP can be separated off by means of vacuum or dry cyclohexane. The amount of bled in the product phase platinum is determined by ICP-AES.
- ionic liquid 1-ethyl-3-methylimidazolium bistrifluoromethanesulfonylimide 10 ml of the ionic liquid 1-ethyl-3-methylimidazolium bistrifluoromethanesulfonylimide are introduced into a heated flask (100-250 ml). This is predried with constant stirring (magnetic stirrer) at 80 0 C (external temperature control) in the HV for one hour. When the ionic liquid is approximately moisture-free, 0.7 mg platinum tetrachloride (equivalent to 55 ppmn) is weighed. The ionic catalyst solution is added after the addition of
- the reaction temperature of 100 0 C is set and controlled at the thermostat.
- the temperature of the intensive cooler (-20 0 C) is generated by a cryostat.
- the reaction temperature is reached, the reactants are carefully added from the dropping funnel (drop rate 5-40 drops / min). If the reaction temperature is exceeded by more than 10 0 C, the addition is interrupted until the reaction temperature has returned to the set point.
- stirring is continued for 60 minutes to ensure complete conversion of the reactants. Thereafter, ionic liquid and products are cooled in an ice bath.
- the content of the three-necked flask is added to a syringe for phase separation, organic phase (top) and ionic catalyst solution are separated and filled into separate vessels. It dissolves a small amount of the products in the ionic catalyst solution and can be removed in vacuo if desired.
- the organic phase is analyzed by gas chromatography.
- the amount of bled in the product phase platinum is determined by ICP-AES.
- the ionic liquid is introduced again without work-up into the apparatus and used again in the manner already described (preparation and amount of the reactants used) in the reaction. It is important to pay attention to sufficient protective gas technology. A drying of the ionic liquid in a vacuum can be omitted here. Such recycling can be successfully carried out for at least four steps.
- Table 4 shows the results after the respective recycling. It can be seen that the reuse of the ionic catalyst solution leads to good results even after the third recycle.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006029430A DE102006029430A1 (de) | 2006-06-27 | 2006-06-27 | Verfahren zur Herstellung von siliciumorganischen Verbindungen durch Hydrosilylierung in ionischen Flüssigkeiten |
PCT/EP2007/056210 WO2008000689A1 (fr) | 2006-06-27 | 2007-06-21 | Procédé de production de composés organosilicium par hydrosilylation de liquides ioniques |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2049553A1 true EP2049553A1 (fr) | 2009-04-22 |
Family
ID=38430546
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP07765548A Withdrawn EP2049553A1 (fr) | 2006-06-27 | 2007-06-21 | Procédé de production de composés organosilicium par hydrosilylation de liquides ioniques |
Country Status (6)
Country | Link |
---|---|
US (1) | US20100267979A1 (fr) |
EP (1) | EP2049553A1 (fr) |
JP (1) | JP2009541420A (fr) |
CN (1) | CN101472932A (fr) |
DE (1) | DE102006029430A1 (fr) |
WO (1) | WO2008000689A1 (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI588210B (zh) * | 2007-12-27 | 2017-06-21 | 邁圖高新材料日本合同公司 | Thermosetting silicone rubber composition |
TWI457398B (zh) * | 2007-12-27 | 2014-10-21 | Momentive Performance Mat Jp | Thermosetting Silicone Oxygenated Compounds |
CN101671356B (zh) * | 2009-07-23 | 2011-12-28 | 杭州师范大学 | 一种室温离子液体/超临界co2介质中铑络合物催化烯烃的硅氢加成反应 |
EP2875166B1 (fr) * | 2012-07-20 | 2018-04-11 | L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Précurseurs d'organosilane pour des applications faisant intervenir des films contenant du silicium dans des procédés ald/cvd |
DE102014203770A1 (de) * | 2014-02-28 | 2015-09-03 | Wacker Chemie Ag | Verfahren zur Hydrosilylierung unter Zusatz organischer Salze |
JP6275866B2 (ja) * | 2014-03-25 | 2018-02-07 | ダウ コーニング コーポレーションDow Corning Corporation | 揮発性シロキサンを供給混合物から分離する方法 |
EP3155036B1 (fr) | 2014-06-11 | 2019-07-31 | Dow Silicones Corporation | Procédé de formation d'un produit d'organosilicium à l'aide d'un contacteur à membrane pour réagir à un gaz et un liquide |
CN106633772B (zh) * | 2016-12-24 | 2018-07-13 | 衢州普信新材料有限公司 | 一种用于聚碳酸酯的有机硅阻燃剂的制备方法 |
CN109384233B (zh) * | 2018-12-13 | 2023-10-20 | 江苏中能硅业科技发展有限公司 | 一种用于处理硅聚合物的方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10157198C2 (de) * | 2001-11-22 | 2002-11-14 | Wacker Chemie Gmbh | Ligandentausch an Organochlorsilanen in ionischen Flüssigkeiten |
DE10232305A1 (de) * | 2002-07-17 | 2004-02-05 | Goldschmidt Ag | Verfahren zur Herstellung von organomodifizierten Polysiloxanen unter Verwendung ionischer Flüssigkeiten |
DE10236079A1 (de) * | 2002-08-07 | 2004-02-26 | Umicore Ag & Co.Kg | Neue Nickel-, Palladium- und Platin-Carbenkomplexe, ihre Herstellung und Verwendung in katalytischen Reaktionen |
DE10257938A1 (de) * | 2002-12-12 | 2004-06-24 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Metallkomplexen der Gruppen 6 bis 10 des Periodensystems und ihr Einsatz als Katalysatoren |
DE102006039191A1 (de) * | 2006-08-21 | 2008-03-20 | Wacker Chemie Ag | Kontinuierliche Herstellung von Organosilanen |
-
2006
- 2006-06-27 DE DE102006029430A patent/DE102006029430A1/de not_active Withdrawn
-
2007
- 2007-06-21 WO PCT/EP2007/056210 patent/WO2008000689A1/fr active Application Filing
- 2007-06-21 JP JP2009517131A patent/JP2009541420A/ja not_active Withdrawn
- 2007-06-21 US US12/306,050 patent/US20100267979A1/en not_active Abandoned
- 2007-06-21 EP EP07765548A patent/EP2049553A1/fr not_active Withdrawn
- 2007-06-21 CN CNA2007800224706A patent/CN101472932A/zh active Pending
Non-Patent Citations (1)
Title |
---|
See references of WO2008000689A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2008000689A1 (fr) | 2008-01-03 |
JP2009541420A (ja) | 2009-11-26 |
DE102006029430A1 (de) | 2008-01-03 |
CN101472932A (zh) | 2009-07-01 |
US20100267979A1 (en) | 2010-10-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2008000689A1 (fr) | Procédé de production de composés organosilicium par hydrosilylation de liquides ioniques | |
EP1245271B1 (fr) | Appareil et procédé pour préparer trialkoxysilanes practiquement exempts de chlore | |
EP1520870B1 (fr) | Procédé pour préparation des combinaisons organiques de silicium | |
EP1894935B1 (fr) | Production continue d'organosilanes | |
EP0600266B1 (fr) | Procédé de préparation d'organopolysiloxanes contenant des groupes SiH | |
DE69130599T2 (de) | Verfahren zur Herstellung von Vinylalkoxysilanen | |
EP3440088B1 (fr) | Mélange hydrosilylable exempt de métaux nobles | |
EP2006250B1 (fr) | Procédé de préparation de silanes comportant des groupes SiH | |
EP0032376A2 (fr) | Procédé pour la préparation en continu de silanes ou polysiloxanes contenant un groupement SiOC | |
EP3195932B1 (fr) | Catalyseur de réaction d'hydrosilylation | |
EP0709388A1 (fr) | Procédé de préparation d'alcoxysilanes | |
EP3966217B1 (fr) | Composés de germanium(ii) cationiques, procédé de préparation de ces composés et leur utilisation comme catalyseurs d'hydrosilylation | |
DE2834691C2 (de) | Monomere, polymere und traegerfixierte rhodiumkomplexverbindungen, verfahren zu ihrer herstellung und verwendung als katalysatoren | |
EP2550281B1 (fr) | Derives cyclique sila-oxa | |
EP3110823A1 (fr) | Procédé d'hydrosilylation sous addition de sels organiques | |
EP3500580B1 (fr) | Procédé de production d'hydridosilanes | |
DE112018001105T5 (de) | Sequenzkontrolliertes Oligosiloxan und Herstellungsverfahren und Oligosiloxansynthesevorrichtung dafür | |
DE1768588B1 (de) | Verfahren zur Alkylierung von Silicium- und Zinnderivaten | |
EP0205891A1 (fr) | Organosilanes contenant des groupes phényléniques, procédé de leur préparation | |
DE19619138A1 (de) | Verfahren zur Herstellung von vinylierten Silicium-organischen Verbindungen | |
DE69130433T2 (de) | Verfahren zur Herstellung von Cyclopentyl-trichlorosilan | |
DE69424503T2 (de) | Verfahren zur Herstellung von Dimethylchlorsilan und Triorganochlorsilan | |
DE10104966A1 (de) | Verfahren zur Herstellung von in 3-Stellung funktionalisierten Propylsilanen | |
DE69417502T2 (de) | Ein Verfahren zur Herstellung von Platin-Komplexen | |
DE10034894A1 (de) | Verfahren zur Herstellung von Vinylsilanen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20081219 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC MT NL PL PT RO SE SI SK TR |
|
AX | Request for extension of the european patent |
Extension state: AL BA HR MK RS |
|
17Q | First examination report despatched |
Effective date: 20090831 |
|
DAX | Request for extension of the european patent (deleted) | ||
RBV | Designated contracting states (corrected) |
Designated state(s): BE DE FR GB IT |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20120606 |