US2666776A - Production of organic silicon compounds - Google Patents
Production of organic silicon compounds Download PDFInfo
- Publication number
- US2666776A US2666776A US156947A US15694750A US2666776A US 2666776 A US2666776 A US 2666776A US 156947 A US156947 A US 156947A US 15694750 A US15694750 A US 15694750A US 2666776 A US2666776 A US 2666776A
- Authority
- US
- United States
- Prior art keywords
- copper
- silicon
- production
- alloy
- organic silicon
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000003377 silicon compounds Chemical class 0.000 title description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001502 aryl halides Chemical class 0.000 claims description 2
- 239000012808 vapor phase Substances 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 10
- 229910045601 alloy Inorganic materials 0.000 description 8
- 239000000956 alloy Substances 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001879 copper Chemical class 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 4
- 229910000881 Cu alloy Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000676 Si alloy Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkyl silicon halides Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 229910000519 Ferrosilicon Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VNJCDDZVNHPVNM-UHFFFAOYSA-N chloro(ethyl)silane Chemical class CC[SiH2]Cl VNJCDDZVNHPVNM-UHFFFAOYSA-N 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- WCCJDBZJUYKDBF-UHFFFAOYSA-N copper silicon Chemical compound [Si].[Cu] WCCJDBZJUYKDBF-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002893 slag 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
- C07F7/16—Preparation thereof from silicon and halogenated hydrocarbons direct synthesis
Definitions
- Another object of the invention is to provide a simple and economical catalytic process for producing organosilicon halides, and particularly alkyl and aryl compounds thereof, with greater uniformity of conversion and higher yield than has heretofore been possible.
- alkyl or aryl halides of silicon by reacting gaseous aryl or alkyl halides with silicon in the presence of copper, nickel, antimony, copper oxide or copper chloride.
- gaseous aryl or alkyl halides with silicon in the presence of copper, nickel, antimony, copper oxide or copper chloride.
- the various possible combinations of these materials yield fluctuating transformations and outputs, so that it is necessary for economic reasons to use catalysts which promote uniform transformation and high output.
- aryl or alkyl silicon halides particularly dialkyl or diaryldihalogensilanes
- an alloy which contains besides silicon and copper also a metal of the th to 8th groups of the periodic table, particular cobalt, nickel, iron or phosphorus.
- These bodies can be used as powders, lumps, or as pressings.
- An additional increase in emciency is attained if the catalyst is used in connection with an activator, for example a copper salt.
- the catalyst is wetted or coated with solutions or pastes of copper salts.
- inorganic salts particularly copper chloride or salt mixtures are preferred above all other.
- the activation may be performed before or during the conversion. It is also possible to bring about the formation of metal salts on the catalyst through corre sponding transformations before or during the production of the organosilicon compound; thereby the desired oxidation stages may be adjusted or maintained before or during the transformation.
- the procedure is preferably such that an alloy of silicon, copper, and a metal of the 5th to 8th groups, for example cobalt, nickel, iron or phosphorous, is melted under slag or an inert gas.
- the finished alloy is reduced to pieces or ground into a powder which is pressed into tablets.
- the pieces may be wet with a copper chloride solution or paste, or the powdered alloy may be mixed with such solution and. then compressed.
- the copper salt may also be formed by reaction of copper with an acid, such as hydrochloric acid, before or during the transformation. In the latter case the acid may be introduced into the reaction simul- 'taneously with the halogen compounds.
- the halide is conducted at an elevated temperature preferably between 250 and 380 C. over a catalyst'such as that described above, the silicon is transformed uniformly and with a good output to the corresponding organic silicon compounds which contain chiefly dialkyl or aryldihalogensilanes.
- Example I An alloy consisting of silicon, copper and cobait is melted and then reduced in the manner described above. Ethyl chloride is conducted in contact with this alloy at an elevated temperature as previously described. Ethylchlorosilanes are produced with a good output.
- Example II An alloy of ferrosilicon (90% silicon) and copper (about 20-30%) is prepared. This is pulverized and the powder is treated with a solution of Cu-hydrochloric acid, which suitably contains some copper in bivalent form. After drying, the powder is converted with methyl chloride, preferably at 270-300 C. After 21 hours 6.690 kg. raw product was formed from about 2.1 kg. of treated silicon.
- the reaction product contained about 2,400 g. of pure dimethyldichlorsilane and 2,170 g. pure methyl trichlorsilane, up to 42 C. about 380 g. were transformed, the rest was distributed to intermediate fractions of 425-50" 0., 50-60 C., -63 C., as well as a residue of 300 g. B. P. over C.
- An alloy of silicon, copper, and. niclgel whiclg, contains 1400 g. silicon is mixed with"cuprous' chloride. During a period of 26 hours methyl chloride is passed over this material at a 't'einperature of about 275-280" C. 512, kg. product nnealed l mshqi vent qn. c aimed i 1, The proce s for p odu ing or anohal eeno 511219.
- reaction massijor use in the production of organosilicon halides consisting essentially of an allgyoij silicon, copper and a metal selected from the group consisting of iron, cabalt, and nickel, i h. memes mes rt e ins. a oppe alt.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Description
Patented Jan. 19, 1954 PRODUCTION or ORGANIC SILICON COMPOUNDS Siegfried Nitzsche, Burghausen, Upper Bavaria,
Germany, assignor, by mesne assignments, to Wacker-Chemie G. in. b. H., Munich, Germany No Drawing. Application April 19, 1950, Serial No. 156,947
Claims'priority, application Germany May 5, 1949 7 Claims. (Cl. 260-4482) This invention relates to the production of organosilicon halides and it has for its object to provide a novel and improved process for this purpose. 7
Another object of the invention is to provide a simple and economical catalytic process for producing organosilicon halides, and particularly alkyl and aryl compounds thereof, with greater uniformity of conversion and higher yield than has heretofore been possible.
Various other objects and advantages will be apparent as the nature of the invention is more fully disclosed.
The present application is a continuation-inpart of application Serial No. 140,157, filed January 23, 1950.
It is possible to produce alkyl or aryl halides of silicon by reacting gaseous aryl or alkyl halides with silicon in the presence of copper, nickel, antimony, copper oxide or copper chloride. However, the various possible combinations of these materials yield fluctuating transformations and outputs, so that it is necessary for economic reasons to use catalysts which promote uniform transformation and high output.
I have found that these requirements are attained to a satisfactory degree, and that aryl or alkyl silicon halides, particularly dialkyl or diaryldihalogensilanes, are obtained if an alloy is used which contains besides silicon and copper also a metal of the th to 8th groups of the periodic table, particular cobalt, nickel, iron or phosphorus. These bodies can be used as powders, lumps, or as pressings. An additional increase in emciency is attained if the catalyst is used in connection with an activator, for example a copper salt. For this purpose the catalyst is wetted or coated with solutions or pastes of copper salts. As such inorganic salts, particularly copper chloride or salt mixtures are preferred above all other. The activation may be performed before or during the conversion. It is also possible to bring about the formation of metal salts on the catalyst through corre sponding transformations before or during the production of the organosilicon compound; thereby the desired oxidation stages may be adjusted or maintained before or during the transformation.
For the production of the catalyst the procedure is preferably such that an alloy of silicon, copper, and a metal of the 5th to 8th groups, for example cobalt, nickel, iron or phosphorous, is melted under slag or an inert gas. The finished alloy is reduced to pieces or ground into a powder which is pressed into tablets. In order to activate this alloy the pieces may be wet with a copper chloride solution or paste, or the powdered alloy may be mixed with such solution and. then compressed. The copper salt may also be formed by reaction of copper with an acid, such as hydrochloric acid, before or during the transformation. In the latter case the acid may be introduced into the reaction simul- 'taneously with the halogen compounds. If the halide is conducted at an elevated temperature preferably between 250 and 380 C. over a catalyst'such as that described above, the silicon is transformed uniformly and with a good output to the corresponding organic silicon compounds which contain chiefly dialkyl or aryldihalogensilanes.
Example I An alloy consisting of silicon, copper and cobait is melted and then reduced in the manner described above. Ethyl chloride is conducted in contact with this alloy at an elevated temperature as previously described. Ethylchlorosilanes are produced with a good output.
Example II Example III An alloy of ferrosilicon (90% silicon) and copper (about 20-30%) is prepared. This is pulverized and the powder is treated with a solution of Cu-hydrochloric acid, which suitably contains some copper in bivalent form. After drying, the powder is converted with methyl chloride, preferably at 270-300 C. After 21 hours 6.690 kg. raw product was formed from about 2.1 kg. of treated silicon. The reaction product contained about 2,400 g. of pure dimethyldichlorsilane and 2,170 g. pure methyl trichlorsilane, up to 42 C. about 380 g. were transformed, the rest was distributed to intermediate fractions of 425-50" 0., 50-60 C., -63 C., as well as a residue of 300 g. B. P. over C.
3 (730 mm.). After the expiration of the abovementioned 21 hours 5% of hydrochloric acid was added to the methyl chloride, and there was formed in the course of about the next succeeding 5 hours. at a somewhat" higher temperature; a further kg. raw product, which consisted mainly of methylchlorosilanes. Usually when an iron containing silicon copper alloy of about 6 per cent iron is used, about 3 15g. of silanes are formed from each 10kg. of methyl chloride. I Example. 11V,
An alloy of silicon, copper, and. niclgel whiclg, contains 1400 g. silicon is mixed with"cuprous' chloride. During a period of 26 hours methyl chloride is passed over this material at a 't'einperature of about 275-280" C. 512, kg. product nnealed l mshqi vent qn. c aimed i 1, The proce s for p odu ing or anohal eeno 511219. 3 which QOmDtiseS reacting a material selected-trope the group consisting oiaryl and alkyl '4 halides in vapor phase with an alloy consisting essentially of silicon, copper and a metal selected from the group consisting of iron, cobalt, and nickel, in the presence of a copper salt.
- '2. The" process according tdclaim 1 in which the halide is methyl chloride.
3. The process according to claim 1 in which the halide is ethyl chloride.
4-. The. process according to claim 1 in which the reaction is conducted at a temperature of about 250 to 380 C.
5. The. process according to claim 1 in which the copper salt isa copper choride.
6. The process according to claim 1 in which n the halide employed contains also hydrogen hali e.
'7 A reaction massijor use in the production of organosilicon halides consisting essentially of an allgyoij silicon, copper and a metal selected from the group consisting of iron, cabalt, and nickel, i h. memes mes rt e ins. a oppe alt.
srscmrm NI'IT SQHE- Referenc s, Qiteai in, t e fi i is tent UNITEP: STATES... PATENTS.-
Nlll'ilbflf Name Date LIFT-7,17; Machin Sept. 30. 1930 2,380,995 Rochow V Aug. '7, 1945 2 4 9 G ll a 9 2-,f 7. Berr r, 1,-
Claims (1)
1. THE PROCESS FOR PRODUCING ORGANOHALOGENOSILANES WHICH COMPRISES REACTING A MATERIAL SELECTED FROM THE GROUP CONSISTING OF ARYL AND ALKYL HALIDES IN VAPOR PHASE WITH AN ALLOWY CONSISTING ESSENTIALLY OF SILICON, COPPER AND A METAL, SELECTED FROM THE GROUP CONSISTING OF IRON, COBALT, AND NICKEL, IN THE PRESENCE OF A COPPER SALT.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP41780A DE921566C (en) | 1949-05-05 | 1949-05-05 | Process for the preparation of alkyl- or arylhalosilanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2666776A true US2666776A (en) | 1954-01-19 |
Family
ID=27184988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US156947A Expired - Lifetime US2666776A (en) | 1949-05-05 | 1950-04-19 | Production of organic silicon compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2666776A (en) |
| CH (1) | CH282375A (en) |
| DE (1) | DE921566C (en) |
| GB (1) | GB681387A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3110721A (en) * | 1960-06-24 | 1963-11-12 | Philadelphia Quartz Co | Preparation of organo-halogenosilanes |
| US4181673A (en) * | 1979-01-23 | 1980-01-01 | Veb Chemiewerk Nunchritz | Process for preparing dimethylhydrogenchlorosilane |
| US4487950A (en) * | 1982-04-16 | 1984-12-11 | General Electric Company | Method for making methylchlorosilanes |
| US4500724A (en) * | 1983-07-28 | 1985-02-19 | General Electric Company | Method for making alkylhalosilanes |
| USRE33452E (en) * | 1983-07-28 | 1990-11-20 | General Electric Company | Method for making alkylhalosilanes |
| US5281739A (en) * | 1992-12-23 | 1994-01-25 | Dow Corning Corporation | Process for manufacture of alkylhalosilanes |
| US20080262258A1 (en) * | 2004-05-04 | 2008-10-23 | Dow Corning Corporation | Container For Forming Self-Baking Electrodes |
| EP3233731A4 (en) * | 2014-12-18 | 2018-10-17 | Dow Silicones Corporation | Method for producing aryl-functional silanes |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2903473A (en) * | 1954-03-19 | 1959-09-08 | Takami Yasuo | Process for the production of phenylchlorosilanes |
| DE1076131B (en) * | 1954-09-25 | 1960-02-25 | Wacker Chemie Gmbh | Process for the preparation of organohalosilanes |
| GB929024A (en) * | 1960-06-02 | 1963-06-19 | Unilever Ltd | Preparation of organo-halogeno-silanes |
| FR2707619B1 (en) * | 1993-07-01 | 1995-09-01 | Pechiney Electrometallurgie | Metallurgical silicon containing phosphorus and intended for the preparation of alkyl or aryl halosilanes. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1777174A (en) * | 1929-04-04 | 1930-09-30 | P M G Metal Trust Ltd | Method of improving copper or copper alloys and hardener for use therein |
| US2380995A (en) * | 1941-09-26 | 1945-08-07 | Gen Electric | Preparation of organosilicon halides |
| US2464033A (en) * | 1947-02-27 | 1949-03-08 | Gen Electric | Preparation of dialkyl-substituted dihalogenosilanes |
| US2488487A (en) * | 1946-02-07 | 1949-11-15 | Dow Chemical Co | Production of alkyl silicon halides |
-
1949
- 1949-05-05 DE DEP41780A patent/DE921566C/en not_active Expired
-
1950
- 1950-01-07 CH CH282375D patent/CH282375A/en unknown
- 1950-01-25 GB GB2005/50A patent/GB681387A/en not_active Expired
- 1950-04-19 US US156947A patent/US2666776A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1777174A (en) * | 1929-04-04 | 1930-09-30 | P M G Metal Trust Ltd | Method of improving copper or copper alloys and hardener for use therein |
| US2380995A (en) * | 1941-09-26 | 1945-08-07 | Gen Electric | Preparation of organosilicon halides |
| US2488487A (en) * | 1946-02-07 | 1949-11-15 | Dow Chemical Co | Production of alkyl silicon halides |
| US2464033A (en) * | 1947-02-27 | 1949-03-08 | Gen Electric | Preparation of dialkyl-substituted dihalogenosilanes |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3110721A (en) * | 1960-06-24 | 1963-11-12 | Philadelphia Quartz Co | Preparation of organo-halogenosilanes |
| US4181673A (en) * | 1979-01-23 | 1980-01-01 | Veb Chemiewerk Nunchritz | Process for preparing dimethylhydrogenchlorosilane |
| US4487950A (en) * | 1982-04-16 | 1984-12-11 | General Electric Company | Method for making methylchlorosilanes |
| US4500724A (en) * | 1983-07-28 | 1985-02-19 | General Electric Company | Method for making alkylhalosilanes |
| USRE33452E (en) * | 1983-07-28 | 1990-11-20 | General Electric Company | Method for making alkylhalosilanes |
| US5281739A (en) * | 1992-12-23 | 1994-01-25 | Dow Corning Corporation | Process for manufacture of alkylhalosilanes |
| US20080262258A1 (en) * | 2004-05-04 | 2008-10-23 | Dow Corning Corporation | Container For Forming Self-Baking Electrodes |
| EP3233731A4 (en) * | 2014-12-18 | 2018-10-17 | Dow Silicones Corporation | Method for producing aryl-functional silanes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE921566C (en) | 1954-12-20 |
| GB681387A (en) | 1952-10-22 |
| CH282375A (en) | 1952-04-30 |
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