GB573906A - Process for the production of organo substituted silicon compounds - Google Patents
Process for the production of organo substituted silicon compoundsInfo
- Publication number
- GB573906A GB573906A GB650543A GB650543A GB573906A GB 573906 A GB573906 A GB 573906A GB 650543 A GB650543 A GB 650543A GB 650543 A GB650543 A GB 650543A GB 573906 A GB573906 A GB 573906A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silicane
- orthosilicate
- reacted
- alkyl
- sodium
- 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
Links
- 150000003377 silicon compounds Chemical class 0.000 title abstract 2
- 125000000962 organic group Chemical group 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 alkyl orthosilicate Chemical compound 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 abstract 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 abstract 1
- 229910000497 Amalgam Inorganic materials 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 abstract 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229910001023 sodium amalgam Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1876—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
Organo-substituted silicon compounds are prepared by reacting an alkyl orthosilicate with an alkyl, cyclo-alkyl, aryl or aralkyl halogenide in the presence of an alkali metal. The reaction is preferably carried out in an inert organic solvent, with the alkali metal either in a finely-divided state or in the form of an amalgam. The proportions of the reactants may be varied with the resultant formation of compounds in which one, two or three of the alkoxy radicals are replaced by alkyl &c. radicals. If the reaction is carried out in the presence of excess orthosilicate which is one of the preferred forms of the invention, the main product is a compound of the structure R1Si(OR)3. In examples: (1) methyl orthosilicate is reacted with iso-amyl bromide in toluene solution in the presence of sodium to give a mixture of mono-iso-amyl trimethoxy silicane and di-iso-amyl-dimethoxy silicane; (2) methyl orthosilicate is reacted with chlorobenzene in liquid paraffin solution in the presence of sodium to form phenyl trimethoxy silicane; (3) as in example (2) using toluene as the solvent; (4) as in example (2) using cyclohexyl bromide instead of chlorobenzene; (5) as in example (1) using benzyl chloride as the halide; (6) ethyl orthosilicate is reacted with ethyl bromide in dekalin solution in the presence of sodium to give a mixture of monoethyl triethoxy silicane, diethyl diethoxy silicane, and triethyl ethoxy silicane; (7) methyl orthosilicate is reacted with N-hexyl bromide in toluene solution in the presence of sodium amalgam to give N-hexyl trimethoxy silicane. If desired, the alkylation may be carried out in two or more stages and in this case different hydrocarbon radicals may be introduced in each stage.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB650543A GB573906A (en) | 1943-04-22 | 1943-04-22 | Process for the production of organo substituted silicon compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB650543A GB573906A (en) | 1943-04-22 | 1943-04-22 | Process for the production of organo substituted silicon compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB573906A true GB573906A (en) | 1945-12-12 |
Family
ID=9815733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB650543A Expired GB573906A (en) | 1943-04-22 | 1943-04-22 | Process for the production of organo substituted silicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB573906A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521267A (en) * | 1947-09-08 | 1950-09-05 | Uddeholms Ab | Method of alkylating alkoxy silanes |
| US2985678A (en) * | 1957-11-27 | 1961-05-23 | Ethyl Corp | Tert-alkyl alkoxy silanes and preparation thereof |
| US3160647A (en) * | 1961-05-19 | 1964-12-08 | Ethyl Corp | Alkylation of dialkoxy monohalo silanes |
| US3223736A (en) * | 1962-07-20 | 1965-12-14 | Carlisle Chemicals Works Inc | Preparation of alkyl phosphines from hydrocarbon phosphites and alkyl sodium compounds |
| US5068387A (en) * | 1989-12-01 | 1991-11-26 | Dow Corning Corporation | Production of organofunctional alkoxysilanes |
| US5120458A (en) * | 1991-01-02 | 1992-06-09 | Ethyl Corporation | Phenyltrialkylsilane lubricating compositions |
| WO2001077120A1 (en) * | 2000-04-05 | 2001-10-18 | General Electric Company | Method for making organooxysilanes |
| CN102898457A (en) * | 2012-05-16 | 2013-01-30 | 杭州师范大学 | Ethylphenyldiethoxysilane and preparation method thereof |
-
1943
- 1943-04-22 GB GB650543A patent/GB573906A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2521267A (en) * | 1947-09-08 | 1950-09-05 | Uddeholms Ab | Method of alkylating alkoxy silanes |
| US2985678A (en) * | 1957-11-27 | 1961-05-23 | Ethyl Corp | Tert-alkyl alkoxy silanes and preparation thereof |
| US3160647A (en) * | 1961-05-19 | 1964-12-08 | Ethyl Corp | Alkylation of dialkoxy monohalo silanes |
| US3223736A (en) * | 1962-07-20 | 1965-12-14 | Carlisle Chemicals Works Inc | Preparation of alkyl phosphines from hydrocarbon phosphites and alkyl sodium compounds |
| US5068387A (en) * | 1989-12-01 | 1991-11-26 | Dow Corning Corporation | Production of organofunctional alkoxysilanes |
| US5120458A (en) * | 1991-01-02 | 1992-06-09 | Ethyl Corporation | Phenyltrialkylsilane lubricating compositions |
| WO2001077120A1 (en) * | 2000-04-05 | 2001-10-18 | General Electric Company | Method for making organooxysilanes |
| US6667411B2 (en) | 2000-04-05 | 2003-12-23 | General Electric Company | Method for making organooxysilanes |
| CN102898457A (en) * | 2012-05-16 | 2013-01-30 | 杭州师范大学 | Ethylphenyldiethoxysilane and preparation method thereof |
| CN102898457B (en) * | 2012-05-16 | 2015-06-17 | 杭州师范大学 | Ethylphenyldiethoxysilane and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB593727A (en) | Improvements in and relating to methods of rendering materials water-repellent | |
| GB573906A (en) | Process for the production of organo substituted silicon compounds | |
| GB767400A (en) | Process for the manufacture of trialkylaluminium compounds | |
| GB740274A (en) | Process of preparing an alkyl or aryl tin compound | |
| US2530367A (en) | Disproportionation of alkoxysilanes | |
| GB685657A (en) | Improvements in and relating to methods of preparing organohalogenosilanes | |
| GB825987A (en) | Method of alkylating silicon tetrachloride or alkyl-or aryl-chlorosilanes | |
| GB751665A (en) | A process for preparing alkoxysilicon compounds | |
| GB987443A (en) | Process for the alkylation of halogenosilanes | |
| GB802796A (en) | Method of preparing hydrocarbon-tin compounds | |
| GB684293A (en) | Improvements in or relating to organosilicon compounds | |
| GB1057343A (en) | Organo-substituted borazines | |
| GB695610A (en) | Process of preparing a tetra alkyl or aryl tin | |
| GB824428A (en) | Improvements in and relating to the production of aluminium alkyls | |
| GB669179A (en) | Organo silicon compounds | |
| GB1187497A (en) | Improvements in or relating to the production of Hydrocarbonoxy Silanes | |
| ES360438A1 (en) | Process for the preparation of alkyl-thiono-phosphonic acid dichlorides | |
| GB671553A (en) | Improvements in organosilicon compounds | |
| GB627809A (en) | A process for the manufacture of organo-silicon compounds | |
| GB669178A (en) | Organo silicon compounds | |
| GB671710A (en) | Improvements in or relating to chlorosilanes | |
| GB923179A (en) | Process for the production of alkyl tin compounds | |
| GB876708A (en) | Process for producing alkylhydrosilanes | |
| US3488369A (en) | Process for the production of hydrocarbonlead compounds | |
| GB632563A (en) | A process for the manufacture of organo-silicon compounds |