JP6338651B2 - グリニャールカップリング反応において高選択性のジアルキル−、ジアリール−、及びアルキルアリール−ジハロシランの製造方法 - Google Patents
グリニャールカップリング反応において高選択性のジアルキル−、ジアリール−、及びアルキルアリール−ジハロシランの製造方法 Download PDFInfo
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- 238000005859 coupling reaction Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000004795 grignard reagents Chemical class 0.000 claims description 65
- 239000007818 Grignard reagent Substances 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 49
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 46
- 239000012530 fluid Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000376 reactant Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 18
- 238000003747 Grignard reaction Methods 0.000 claims description 15
- 238000011010 flushing procedure Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000004791 alkyl magnesium halides Chemical group 0.000 claims description 5
- 150000004792 aryl magnesium halides Chemical class 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 5
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical group C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 5
- IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical group [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 159000000003 magnesium salts Chemical class 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 4
- 239000013529 heat transfer fluid Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical group [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- OJZNZOXALZKPEA-UHFFFAOYSA-N chloro-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C)C1=CC=CC=C1 OJZNZOXALZKPEA-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 2
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002530 polyetherether ketone Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical compound COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920004511 Dow Corning® 200 Fluid Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- ADSXDBCZNVXTRD-UHFFFAOYSA-N [Mg]C1=CC=CC=C1 Chemical compound [Mg]C1=CC=CC=C1 ADSXDBCZNVXTRD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- -1 isopropanol (IPA) Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FAANOBAJWDSCGM-UHFFFAOYSA-M magnesium;1,2,3-trifluorobenzene-5-ide;bromide Chemical compound [Mg+2].[Br-].FC1=C[C-]=CC(F)=C1F FAANOBAJWDSCGM-UHFFFAOYSA-M 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- KVENDAGPVNAYLY-UHFFFAOYSA-N tribromo(ethyl)silane Chemical compound CC[Si](Br)(Br)Br KVENDAGPVNAYLY-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 239000008096 xylene 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/125—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving both Si-C and Si-halogen linkages, the Si-C and Si-halogen linkages can be to the same or to different Si atoms, e.g. redistribution 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
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/122—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-C linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Claims (11)
- ジアルキル−、ジアリール−、又はアルキルアリール−ジハロシランをグリニャールカップリング反応において高選択性で作製する方法であって、
押し出し流れ反応器(PFR)、連続管型反応器(CTR)、ピストン流れ反応器、及び直列で接続された2つ以上の連続撹拌槽型反応器(CSTR)の群から選択される1つの反応器を準備するステップ、
炭化水素溶媒流れを所定の流量で前記反応器に提供するステップ、
アルキル−又はアリールトリハロシラン流れを所定の流量で前記反応器に提供するステップ、
アルキル−又はアリールマグネシウムハライドを含むグリニャール試剤流れを所定の流量で前記反応器に提供するステップ、
前記溶媒流れ、アルキル−又はアリールトリハロシラン流れ、及びグリニャール試剤流れを一体化して、一体化された反応剤流れを形成させるステップであって、
前記一体化された反応剤流れ中の前記アルキル−又はアリールトリハロシラン:前記グリニャール試剤の質量比が、1.5:1以上であり、及び前記一体化された反応剤流れ中の前記溶媒:前記グリニャール試剤の質量比が3:1以上であるように、前記溶媒流れ、
アルキル−又はアリールトリハロシラン流れ、及び前記グリニャール試剤流れの流量が選択される、ステップ、
前記一体化された反応剤流れを10℃〜80℃の温度で反応させて、R2SiX2、R3SiX、及び塩を含む生成物混合物を形成し、そこでは、各Rがアルキル又はアリール基であるように独立に選択され、Xがハロゲン基であり、及び前記生成物混合物中のR2SiX2:R3SiXの質量比が7:1超であるステップ、及び
所望により、前記生成物混合物を捕集するステップを含む、方法。 - 前記反応器が、少なくとも1つの流体モジュールを含むPFRである、請求項1に記載の方法。
- 前記方法が、前記グリニャール反応の開始に先立って、前記反応器中のベースライン圧力低下を測定するステップ、
前記グリニャール反応の過程の間、前記反応器中の前記圧力低下をモニターするステップ、及び
前記グリニャール反応の過程の間、モニターされる前記反応器にわたる前記圧力低下を前記ベースライン圧力低下と比較して、前記圧力低下の変化を決定するステップであって、 前記圧力低下の変化が、前記反応器中で塊化及び沈降した又は前記反応器中で壁上に堆積した塩が前記反応器を詰まらせた程度に対する測定値を提供する、ステップを更に含む、請求項1又は2に記載の方法。 - 前記方法が、前記グリニャール反応を停止するステップ、
前記反応器を詰まらせる塩を除去するステップ、及び
前記グリニャール反応を再開するステップを更に含む、請求項3に記載の方法。 - 前記反応器を詰まらせる前記塩を除去するステップが、
前記反応器の残部から前記反応器の前記詰まった部分を単離するステップ、
前記反応器の前記単離された部分に炭化水素溶媒をフラッシュして、アルキル−又はアリールトリハロシランを除去するステップ、
全ての塩が除去されるまで、前記反応器の前記単離された部分に水をフラッシュするステップ、
前記反応器の前記単離された部分にアルコールをフラッシュして、いかなる残存する水も除去するステップ、
前記反応器の前記単離された部分に前記炭化水素溶媒を再度フラッシュして、前記アルコールを前記単離された部分から追い出すステップ、及び
前記反応器の前記単離された部分と前記反応器の前記残部との間の接触を再建するステップを更に含む、請求項4に記載の方法。 - 前記一体化された反応剤流れは、前記一体化された反応剤流れが前記反応器中に滞留する平均時間が30秒未満であるように、前記反応器の大きさに基づいて予め決められた流量を有する、請求項1〜4のいずれか一項に記載の方法。
- 前記反応器中における前記一体化された反応剤流れの滞留時間が、20秒未満である、請求項6に記載の方法。
- 溶媒:グリニャール試剤の質量比が5:1超である、請求項1〜7のいずれか一項に記載の方法。
- 前記生成物混合物中のR2SiX2:R3SiXの質量比が12:1超である、請求項1〜8のいずれか一項に記載の方法。
- 前記グリニャール試剤流れが、溶媒中に分散された前記グリニャール試剤を含む溶液であり、
前記溶液中に存在するグリニャール試剤の量が、
前記溶液の全重量基準で75重量%未満である、請求項1〜9のいずれか一項に記載の方法。 - 前記溶媒がトルエンであり、前記グリニャール試剤がフェニルマグネシウムクロリド(PhMgCl)であり、前記アルキル−又はアリールトリハロシランがメチルトリクロロシラン(MeSiCl3)であり、並びに形成される前記生成物混合物が、PhMeSiCl2、Ph2MeSiCl、及びMgCl2を含む、請求項1〜10のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US201361786750P | 2013-03-15 | 2013-03-15 | |
US61/786,750 | 2013-03-15 | ||
PCT/US2014/027339 WO2014152436A1 (en) | 2013-03-15 | 2014-03-14 | A method of preparing dialkyl-diaryl-, and alkylaryl-dihalosilanes with high selectivity in a grignard coupling reaction |
Publications (2)
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JP2016512265A JP2016512265A (ja) | 2016-04-25 |
JP6338651B2 true JP6338651B2 (ja) | 2018-06-06 |
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Country Status (6)
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US (1) | US9828394B2 (ja) |
EP (1) | EP2970343B1 (ja) |
JP (1) | JP6338651B2 (ja) |
KR (1) | KR102189390B1 (ja) |
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CN105164140A (zh) | 2015-12-16 |
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