CA1082216A - Method for producing orthosilicic acid alkyl esters - Google Patents
Method for producing orthosilicic acid alkyl estersInfo
- Publication number
- CA1082216A CA1082216A CA257,119A CA257119A CA1082216A CA 1082216 A CA1082216 A CA 1082216A CA 257119 A CA257119 A CA 257119A CA 1082216 A CA1082216 A CA 1082216A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- silicon
- group
- ester
- surface active
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 35
- 239000010703 silicon Substances 0.000 claims abstract description 35
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 11
- 238000009835 boiling Methods 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 239000011149 active material Substances 0.000 claims abstract description 10
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000676 Si alloy Inorganic materials 0.000 claims abstract description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract 8
- 229910000519 Ferrosilicon Inorganic materials 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 229910052742 iron Inorganic materials 0.000 claims abstract 4
- 229910021332 silicide Inorganic materials 0.000 claims abstract 4
- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 claims abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- -1 nitrogenous organic bases Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 6
- 235000012239 silicon dioxide Nutrition 0.000 claims description 5
- 239000008396 flotation agent Substances 0.000 claims description 3
- 239000000837 restrainer Substances 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims 6
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 4
- 239000000470 constituent Substances 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- QNVBIDULDLPCDQ-UHFFFAOYSA-N Ilicic acid Natural products CC1(O)CCC2(C)CCC(CC2C1)C(=C)C(=O)O QNVBIDULDLPCDQ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FXKCXGBBUBCRPU-GBOPCIDUSA-N 2-[(2r,4ar,8s,8ar)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid Chemical compound C1C[C@@H](C(=C)C(O)=O)C[C@H]2[C@@](C)(O)CCC[C@@]21C FXKCXGBBUBCRPU-GBOPCIDUSA-N 0.000 description 3
- 229910005347 FeSi Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 241000518994 Conta Species 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- JKGITWJSGDFJKO-UHFFFAOYSA-N ethoxy(trihydroxy)silane Chemical class CCO[Si](O)(O)O JKGITWJSGDFJKO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas 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
- C07F7/04—Esters of silicic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP.2532473.6 | 1975-07-19 | ||
| DE2532475A DE2532475C2 (de) | 1975-07-19 | 1975-07-19 | Verfahren zur Herstellung von Orthokieselsäuretetraalkylestern |
| DE19752532476 DE2532476A1 (de) | 1975-07-19 | 1975-07-19 | Verfahren zur herstellung von orthokieselsaeuretetraalkylestern |
| DE19752532473 DE2532473A1 (de) | 1975-07-19 | 1975-07-19 | Verfahren zur herstellung von orthokieselsaeuretetraalkylestern |
| DEP.2532475.8 | 1975-07-19 | ||
| DEP2532476.9 | 1975-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1082216A true CA1082216A (en) | 1980-07-22 |
Family
ID=27186456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA257,119A Expired CA1082216A (en) | 1975-07-19 | 1976-07-16 | Method for producing orthosilicic acid alkyl esters |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4113761A (enExample) |
| JP (1) | JPS5212133A (enExample) |
| CA (1) | CA1082216A (enExample) |
| CH (1) | CH606036A5 (enExample) |
| DD (1) | DD125679A5 (enExample) |
| FR (1) | FR2318872A1 (enExample) |
| IT (1) | IT1066047B (enExample) |
| NL (1) | NL7607914A (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2395323A1 (fr) * | 1977-06-24 | 1979-01-19 | Pompey Acieries | Acier de construction a grains fins, a usinabilite amelioree |
| EP0004730B1 (en) * | 1978-03-23 | 1982-11-10 | Zirconal Processes Limited | Improvements in the manufacture of alkylsilicates and their conversion to alkylpolysilicates |
| JPS5946301B2 (ja) * | 1979-04-19 | 1984-11-12 | 大同特殊鋼株式会社 | 被削性にすぐれた冷間鍛造用鋼およびその製造方法 |
| JPS5946300B2 (ja) * | 1979-03-14 | 1984-11-12 | 大同特殊鋼株式会社 | 被削性にすぐれた冷間鍛造用鋼およびその製造方法 |
| US4288604A (en) * | 1980-05-19 | 1981-09-08 | Stauffer Chemical Company | Method for the production of tetraalkyl silicates |
| US4289889A (en) * | 1980-06-30 | 1981-09-15 | Union Carbide Corporation | Preparation of tetraalkoxysilanes |
| US4323690A (en) * | 1981-04-20 | 1982-04-06 | Carboline Company | Method of making silicate esters |
| JPS61253343A (ja) * | 1985-05-02 | 1986-11-11 | Kobe Steel Ltd | 超硬工具による被切削用快削鋼 |
| JPS62120390A (ja) * | 1985-11-20 | 1987-06-01 | Chisso Corp | テトラメトキシシランの製造方法 |
| US4761492A (en) * | 1987-09-28 | 1988-08-02 | Union Carbide Corporation | Process for recovering trimethoxysilane from a trimethoxysilane and methanol mixture |
| US4762939A (en) * | 1987-09-30 | 1988-08-09 | Union Carbide Corporation | Process for trialkoxysilane/tetraalkoxysilane mixtures from silicon metal and alcohol |
| US4914063A (en) * | 1988-04-04 | 1990-04-03 | The United States Of America As Represented By The United States Department Of Energy | Process for producing organic products containing silicon, hydrogen, nitrogen, and carbon by the direct reaction between elemental silicon and organic amines |
| US5783720A (en) * | 1996-10-10 | 1998-07-21 | Osi Specialties, Inc. | Surface-active additives in the direct synthesis of trialkoxysilanes |
| US6090965A (en) * | 1998-04-02 | 2000-07-18 | Osi Specialties, Inc. | Removal of dissolved silicates from alcohol-silicon direct synthesis solvents |
| US6166237A (en) * | 1999-08-13 | 2000-12-26 | Crompton Corporation | Removal of dissolved silicates from alcohol-silicon direct synthesis solvents |
| US8153566B2 (en) * | 2008-09-30 | 2012-04-10 | Cherron Oronite Company LLC | Lubricating oil compositions |
| US8901050B2 (en) | 2010-03-31 | 2014-12-02 | Chevron Oronite Company Llc | Method for improving copper corrosion performance |
| US8933001B2 (en) | 2010-03-31 | 2015-01-13 | Chevron Oronite Company Llc | Method for improving fluorocarbon elastomer seal compatibility |
| US10442899B2 (en) | 2014-11-17 | 2019-10-15 | Silbond Corporation | Stable ethylsilicate polymers and method of making the same |
| EP3954743A1 (de) | 2020-08-12 | 2022-02-16 | Evonik Operations GmbH | Verwendung von siliziumdioxid zur verbesserung der leitfähigkeit von beschichtungen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768339C3 (de) * | 1968-05-02 | 1974-07-04 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Orthokieselsäuretetramethylester |
| DE1793222A1 (de) * | 1968-08-17 | 1971-04-15 | Dynamit Nobel Ag | Verfahren zur Herstellung von Orthokieselsaeuretetraalkylestern |
| US3803197A (en) * | 1971-05-04 | 1974-04-09 | Anderson Dev Co | Method of preparation of alkyl and 2-alkoxy-ethyl silicates |
-
1976
- 1976-07-15 FR FR7621710A patent/FR2318872A1/fr active Granted
- 1976-07-16 CA CA257,119A patent/CA1082216A/en not_active Expired
- 1976-07-16 DD DD193926A patent/DD125679A5/xx unknown
- 1976-07-16 NL NL7607914A patent/NL7607914A/xx not_active Application Discontinuation
- 1976-07-16 IT IT50477/76A patent/IT1066047B/it active
- 1976-07-16 CH CH916476A patent/CH606036A5/xx not_active IP Right Cessation
- 1976-07-19 JP JP51085911A patent/JPS5212133A/ja active Pending
- 1976-07-19 US US05/706,864 patent/US4113761A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2318872B1 (enExample) | 1982-11-12 |
| IT1066047B (it) | 1985-03-04 |
| JPS5212133A (en) | 1977-01-29 |
| DD125679A5 (enExample) | 1977-05-11 |
| FR2318872A1 (fr) | 1977-02-18 |
| CH606036A5 (enExample) | 1978-10-13 |
| US4113761A (en) | 1978-09-12 |
| NL7607914A (nl) | 1977-01-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |