CN102781947A - 用于转换二硅烷的方法 - Google Patents
用于转换二硅烷的方法 Download PDFInfo
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- disilane
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- hydrogen halide
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- 238000000034 method Methods 0.000 title claims description 19
- 238000006243 chemical reaction Methods 0.000 title description 17
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 11
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims abstract description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 6
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000011787 zinc oxide Substances 0.000 claims abstract description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 40
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 3
- 229960004643 cupric oxide Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 2
- 239000005751 Copper oxide Substances 0.000 abstract 1
- 229910000431 copper oxide Inorganic materials 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- -1 alkyl chlorosilane Chemical compound 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 4
- PVGYYKBIUKOMTG-UHFFFAOYSA-N trichloro-[chloro(dimethyl)silyl]silane Chemical compound C[Si](C)(Cl)[Si](Cl)(Cl)Cl PVGYYKBIUKOMTG-UHFFFAOYSA-N 0.000 description 4
- KQSUTCMQKDYZIY-UHFFFAOYSA-N N,N-dimethylmethanamine trichlorosilane Chemical compound Cl[SiH](Cl)Cl.CN(C)C KQSUTCMQKDYZIY-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- JZALIDSFNICAQX-UHFFFAOYSA-N dichloro-methyl-trimethylsilylsilane Chemical compound C[Si](C)(C)[Si](C)(Cl)Cl JZALIDSFNICAQX-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000005096 rolling process Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- AYRWZUOIHYWCBJ-UHFFFAOYSA-N CN(C)C.[SiH3][SiH3].[Cl+].[Cl+].[Cl+] Chemical compound CN(C)C.[SiH3][SiH3].[Cl+].[Cl+].[Cl+] AYRWZUOIHYWCBJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VYFXMIAQVGXIIN-UHFFFAOYSA-N trichloro(chlorosilyl)silane Chemical compound Cl[SiH2][Si](Cl)(Cl)Cl VYFXMIAQVGXIIN-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- 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
- C07F7/128—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions covered by more than one of the groups C07F7/122 - C07F7/127 and of which the starting material is unknown or insufficiently determined
-
- 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
- C07F7/123—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-halogen linkages
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- 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
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明提供了一种用于制备通式(1)RaSi2Cl6-a(1)的二硅烷的方法，其中使包括通式(2)RbSi2Cl6-b(2)的二硅烷的混合物与卤化氢在氧化铝催化剂的存在下反应，其中R代表具有1到6个碳原子的烷基，a代表1、2或3，b代表4、5或6，所述氧化铝催化剂每100重量份氧化铝包含1到10重量份的氯化铝以及0到10重量份的选自氧化镁、氧化铜、氧化锌及其混合物的金属氧化物。
Description
技术领域
发明涉及用卤化氢从包括氯和烷基的二硅烷催化脱落（detachment）烷基。
背景技术
源自甲基氯及硅的反应的具有高于70°C沸点（高沸物）的高沸点部分含有所谓的“可裂解二硅烷”二甲基四氯二硅烷及三甲基三氯二硅烷，其在胺催化下通过下面已知工艺用卤化氢简单裂解为单硅烷。带有四个、五个及六个甲基的其它二硅烷不能以该方式利用并且还因此叫做“非裂解二硅烷”。
多个专利涉及高沸物到单聚烷基氯硅烷的转换（转化）。已经描述的工艺都成本很高且不方便并且对设备要求高。例如，EP 635510A描述了通过用卤化氢以及含氯化铝的催化剂在高于250°C的温度下进行高沸物到单硅烷的转换。
H.Sakurei等（Aluminum chloride-catalyzed reactions of organosiliconcompounds II,tetrahydron letters No.45,pp.5493-5497,1966,pergamonpress ltd.）描述了在乙酰氯存在下部分在液相中分批转换（转化）二硅烷。
发明内容
发明提供生产通式(1)的二硅烷的方法
RaSi2Cl6-a (1)，
其包括使包括通式(2)的二硅烷的混合物与卤化氢在氧化铝催化剂存在下反应，
RbSi2Cl6-b (2)，
其中
R代表具有1到6个碳原子的烷基，
a代表1、2或3，
b代表4、5或6，
氧化铝催化剂，每100重量份氧化铝，包含1到10重量份的氯化铝以及0到10重量份的选自氧化镁，氧化铜，氧化锌及其混合物中的金属氧化物。
该方法使得能够以简单、稳固及连续方式利用富烷基的二硅烷如六甲基二硅烷、五甲基氯二硅烷及四甲基二氯硅烷。
该方法在路易斯酸催化剂下用卤化氢脱落（detach）烷基以形成所谓的可裂解二硅烷，其可被供应入胺催化的裂解工艺。因为该反应放热，反应器仅要求其保证热移出。
在该方法中优选氯化氢用作卤化氢。
基团R优选具有1到6个碳原子。基团R更特别为甲基或乙基。硅烷(2)可以相对彼此以任何所需的比例存在。它们可类似存在于具有不破坏转换的其它可蒸发物质的混合物中。
二烷基四氯二硅烷和三烷基三氯二硅烷是优选的产品。
氧化铝可为α-氧化铝或优选γ-氧化铝。氧化铝催化剂可用作粉末或优选用作成形制品。
每100重量份氧化铝，氧化铝催化剂优选包括至少1重量份，特别至少3重量份且至多10重量份，特别至多6重量份的氯化铝。每100重量份氧化铝，氧化铝催化剂可包括至多5重量份，特别至多2重量份的金属氧化物。金属镁、铜及锌的任一所需氧化物或混合氧化物可用作金属氧化物或混合氧化物。特别优选氧化镁。
氧化铝催化剂优选具有至少100m2/g的BET表面积，更优选至少230m2/g且优选最大600m2/g。
氧化铝催化剂优选具有至少0.2cm3/g的孔体积，更优选至少0.5cm3/g且优选最大1.5cm3/g。
所用的氧化铝催化剂优选是用氯化铝涂覆的氧化铝-金属氧化物载体材料。氯化铝涂层可通过用氯化氢活化Al2O3原位产生。
该方法在过量卤化氢下进行，优选不高于由化学计量计算产生的卤化氢量的两倍。
该方法优选在不低于150°C、更优选180°C、特别不低于200°C且优选不高于370°C、更优选不高于350°C、甚至更优选不高于280°C、特别不高于240°C下进行。该方法优选在不低于1巴、更优选不低于2巴、特别不低于4巴且优选不高于30、更优选不高15巴、特别不高于10巴下进行。
该方法可分批或优选连续进行。
允许固体催化剂易于处理的任何温度可控的设备可用作该方法的反应器。特别优选用配备有传热介质回路的管状反应器，其允许方便的温度管理。
上面式中的上述符号在每种情况下都具有相互独立的意义。硅原子在所有化学式中为四价。
具体实施方式
在下面的发明实施例及比较例中，除非另有特别陈述，全部量及百分比是以重量计且全部反应在6.5巴（绝对）压力及300°C的温度下实施。
实施例中的反应用标称宽度50的传热介质加热的管状反应器及1升包括γ-氧化铝的催化剂挤出物而实施，γ-氧化铝具有5wt%的氯化铝、200m2/g的BET表面积及0.5cm3/g的孔体积。
实施例3中的催化剂另外含0.8wt%氧化物形式的Mg。
具有70-160°C的沸程的待用的硅烷部分包括不同比例的反应物成分及副产物如各种烷基(C2或更大)-甲基-氯硅烷、氯甲基硅氧烷及烃。
实施例1:
含70%的四甲基二氯二硅烷、五甲基氯二硅烷及六甲基二硅烷的混合物及30%的次要成分的二硅烷部分以0.9mol/h要分离的甲基吞吐量速率（大约170g/h）与1.6倍过量的氯化氢在220°C反应器壳体温度及5.5巴过压下反应以提供到二甲基四氯二硅烷及三甲基三氯硅烷的96%的二硅烷转换。
实施例2:
含55%的四甲基二氯二硅烷、五甲基氯二硅烷及六甲基二硅烷的混合物及45%的次要成分的二硅烷部分以0.75mol/h要分离的甲基吞吐量速率（大约170g/h）与1.6倍过量的氯化氢在220°C反应器壳体温度及5.5巴过压下反应以提供到二甲基四氯二硅烷及三甲基三氯硅烷的77%的二硅烷转换。
实施例3:
含55%的四甲基二氯二硅烷、五甲基氯二硅烷及六甲基二硅烷的混合物及45%的次要成分的二硅烷部分以0.66mol/h要分离的甲基吞吐量速率（大约150g/h）与3倍过量的氯化氢在220°C反应器壳体温度及5.5巴过压下反应以提供到二甲基四氯二硅烷及三甲基三氯硅烷的87%的二硅烷转换。
Claims (6)
1.一种用于生产通式(1)的二硅烷的方法
RaSi2Cl6-a (1)，
该方法包括使包括通式(2)的二硅烷的混合物与卤化氢在氧化铝催化剂存在下反应，
RbSi2Cl6-b (2)，
其中
R代表具有1到6个碳原子的烷基，
a代表数值1、2或3，
b代表数值4、5或6，
所述氧化铝催化剂每100重量份氧化铝含1到10重量份的氯化铝及0到10重量份的选自氧化镁、氧化铜、氧化锌及其混合物的金属氧化物。
2.如权利要求1所述的方法，其中基团R为甲基或乙基。
3.如权利要求1或2所述的方法，其中使用氯化氢作为卤化氢。
4.如权利要求1或2或3所述的方法，所述氧化铝催化剂具有至少0.2cm3/g的孔体积。
5.如权利要求1或2或3或4所述的方法，其中所述氧化铝催化剂具有至少100m2/g的BET表面积。
6.如权利要求1或2或3或4或5所述的方法，其中温度为在180°C到280°C的范围。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010002577.1 | 2010-03-04 | ||
| DE102010002577A DE102010002577A1 (de) | 2010-03-04 | 2010-03-04 | Verfahren zur Umwandlung von Disilanen |
| PCT/EP2011/052440 WO2011107360A1 (de) | 2010-03-04 | 2011-02-18 | Verfahren zur umwandlung von disilanen |
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| Publication Number | Publication Date |
|---|---|
| CN102781947A true CN102781947A (zh) | 2012-11-14 |
| CN102781947B CN102781947B (zh) | 2015-01-21 |
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| CN201180012401.3A Expired - Fee Related CN102781947B (zh) | 2010-03-04 | 2011-02-18 | 用于转换二硅烷的方法 |
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| Country | Link |
|---|---|
| US (1) | US8680312B2 (zh) |
| EP (1) | EP2542558B1 (zh) |
| JP (1) | JP2013521241A (zh) |
| KR (1) | KR101414694B1 (zh) |
| CN (1) | CN102781947B (zh) |
| DE (1) | DE102010002577A1 (zh) |
| WO (1) | WO2011107360A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102015009129B4 (de) | 2014-07-22 | 2016-12-15 | Norbert Auner | Verfahren zur Spaltung von Silicium-Silicium-Bindungen und/oder von Silicium-Chlor-Bindungen in Mono-, Poly- und/oder Oligosilanen |
| JP2022546015A (ja) | 2019-08-22 | 2022-11-02 | ダウ シリコーンズ コーポレーション | ケイ素化合物を精製するためのプロセス |
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| WO2009003805A1 (de) * | 2007-07-04 | 2009-01-08 | Wacker Chemie Ag | Verfahren zur umwandlung von si-h-verbindungen in si-halogen-verbindungen |
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| JPS52108931A (en) * | 1976-03-08 | 1977-09-12 | Toshiba Silicone | Process for manufacturing 1*22dimethyltetrachlorodisilane |
| JPS6039078B2 (ja) * | 1976-06-07 | 1985-09-04 | 東芝シリコ−ン株式会社 | ジシラン類の製造方法 |
| JPS6039079B2 (ja) * | 1976-12-27 | 1985-09-04 | 東芝シリコ−ン株式会社 | ジシラン類の製造方法 |
| US4855471A (en) * | 1988-01-20 | 1989-08-08 | Dow Corning Corporation | Process for the chlorodephenylation of phenyldisilanes |
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2011
- 2011-02-18 WO PCT/EP2011/052440 patent/WO2011107360A1/de active Application Filing
- 2011-02-18 US US13/582,642 patent/US8680312B2/en not_active Expired - Fee Related
- 2011-02-18 EP EP11707119.1A patent/EP2542558B1/de not_active Not-in-force
- 2011-02-18 KR KR1020127020288A patent/KR101414694B1/ko not_active IP Right Cessation
- 2011-02-18 CN CN201180012401.3A patent/CN102781947B/zh not_active Expired - Fee Related
- 2011-02-18 JP JP2012555360A patent/JP2013521241A/ja active Pending
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| CN1637005A (zh) * | 2003-11-20 | 2005-07-13 | 瓦克化学有限公司 | 由烷基氯硅烷类直接合成的残余物制造烷基氯硅烷类的方法 |
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Also Published As
| Publication number | Publication date |
|---|---|
| KR101414694B1 (ko) | 2014-07-03 |
| CN102781947B (zh) | 2015-01-21 |
| US20120330045A1 (en) | 2012-12-27 |
| EP2542558A1 (de) | 2013-01-09 |
| WO2011107360A1 (de) | 2011-09-09 |
| DE102010002577A1 (de) | 2011-09-08 |
| JP2013521241A (ja) | 2013-06-10 |
| EP2542558B1 (de) | 2015-06-17 |
| KR20120099301A (ko) | 2012-09-07 |
| US8680312B2 (en) | 2014-03-25 |
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