CA1105799A - Method of hydrolyzing chlorosilanes - Google Patents
Method of hydrolyzing chlorosilanesInfo
- Publication number
- CA1105799A CA1105799A CA339,435A CA339435A CA1105799A CA 1105799 A CA1105799 A CA 1105799A CA 339435 A CA339435 A CA 339435A CA 1105799 A CA1105799 A CA 1105799A
- Authority
- CA
- Canada
- Prior art keywords
- chlorosilicon
- polyfunctional
- composition
- hydrogen chloride
- aqueous medium
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000003301 hydrolyzing effect Effects 0.000 title claims abstract description 10
- 239000005046 Chlorosilane Substances 0.000 title description 6
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 title description 6
- SLLGVCUQYRMELA-UHFFFAOYSA-N chlorosilicon Chemical compound Cl[Si] SLLGVCUQYRMELA-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 239000012736 aqueous medium Substances 0.000 claims abstract description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000006227 byproduct Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 150000001367 organochlorosilanes Chemical class 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 4
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 23
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 23
- 239000000499 gel Substances 0.000 abstract description 15
- 239000003921 oil Substances 0.000 description 16
- 239000007863 gel particle Substances 0.000 description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- -1 ional chlorosilicon compounds Chemical class 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000010687 lubricating oil Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical class C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000010909 process residue Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 description 1
- 241000908596 Centistes Species 0.000 description 1
- 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 description 1
- 241000283986 Lepus Species 0.000 description 1
- 241001296096 Probles Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FQEKAFQSVPLXON-UHFFFAOYSA-N butyl(trichloro)silane Chemical compound CCCC[Si](Cl)(Cl)Cl FQEKAFQSVPLXON-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NBWIIOQJUKRLKW-UHFFFAOYSA-N chloro(phenyl)silane Chemical class Cl[SiH2]C1=CC=CC=C1 NBWIIOQJUKRLKW-UHFFFAOYSA-N 0.000 description 1
- FXMNVBZEWMANSQ-UHFFFAOYSA-N chloro(silyl)silane Chemical class [SiH3][SiH2]Cl FXMNVBZEWMANSQ-UHFFFAOYSA-N 0.000 description 1
- NQOYHMKLWAVZDX-UHFFFAOYSA-N chloro(silyloxy)silane Chemical class [SiH3]O[SiH2]Cl NQOYHMKLWAVZDX-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- KTPJDYNQZVAFBU-UHFFFAOYSA-N dichloro-[chloro(dimethyl)silyl]-methylsilane Chemical compound C[Si](C)(Cl)[Si](C)(Cl)Cl KTPJDYNQZVAFBU-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910001504 inorganic chloride Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005053 propyltrichlorosilane Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 1
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 description 1
- LMMGPWSCQFYALZ-UHFFFAOYSA-N trichloro-[dichloro(methyl)silyl]oxysilane Chemical compound C[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl LMMGPWSCQFYALZ-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
- 229910052905 tridymite Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Lubricants (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12,684 | 1979-02-16 | ||
| US06/012,684 US4221691A (en) | 1979-02-16 | 1979-02-16 | Method of hydrolyzing chlorosilanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105799A true CA1105799A (en) | 1981-07-28 |
Family
ID=21756196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA339,435A Expired CA1105799A (en) | 1979-02-16 | 1979-11-08 | Method of hydrolyzing chlorosilanes |
Country Status (9)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4609751A (en) * | 1981-12-14 | 1986-09-02 | General Electric Company | Method of hydrolyzing chlorosilanes |
| GB2112407B (en) * | 1981-12-14 | 1985-06-19 | Gen Electric | Method of hydrolyzing chlorosilanes |
| US4408030A (en) * | 1982-03-22 | 1983-10-04 | Dow Corning Corporation | Waste chlorosilane treatment |
| US4463114A (en) * | 1982-03-31 | 1984-07-31 | Minnesota Mining And Manufacturing Company | Antistatic films |
| US4532185A (en) * | 1982-03-31 | 1985-07-30 | Minnesota Mining And Manufacturing Company | Antistatic films |
| DE3523543A1 (de) * | 1985-07-02 | 1987-01-15 | Bayer Ag | Verfahren zur aufarbeitung von hydrolyserueckstaenden aus der methylchlorsilansynthese |
| DE3525495C1 (de) * | 1985-07-17 | 1987-01-02 | Heraeus Schott Quarzschmelze | Verfahren zur Herstellung von Gegenstaenden aus synthetischem Siliziumdioxid |
| DE3829582A1 (de) * | 1988-09-01 | 1990-03-08 | Bayer Ag | Verfahren zur aufarbeitung von hydrolyserueckstaenden aus der organochlorsilansynthese |
| DE3829581A1 (de) * | 1988-09-01 | 1990-03-15 | Bayer Ag | Verfahren zur aufarbeitung von hydrolyserueckstaenden aus der organochlorsilansynthese |
| DE4033157A1 (de) * | 1990-10-12 | 1992-04-16 | Nuenchritz Chemie Gmbh | Verfahren zur herstellung von loeslichen methylalkoxypoly(disilyl)-siloxanen |
| DE4116925C2 (de) * | 1991-05-24 | 1999-06-24 | Huels Silicone Gmbh | Verfahren zur Aufbereitung von Destillationsrückständen der Direkten Synthese von Chlor- und/oder Organochlorsilanen |
| US5312946A (en) * | 1992-04-13 | 1994-05-17 | General Electric Company | Siloxane fluid from methylchlorosilane residue waste |
| US5378790A (en) * | 1992-09-16 | 1995-01-03 | E. I. Du Pont De Nemours & Co. | Single component inorganic/organic network materials and precursors thereof |
| US5876609A (en) * | 1997-03-28 | 1999-03-02 | General Electric Company | Process for treating methylchlorosilanes by-products |
| US5905183A (en) * | 1997-06-03 | 1999-05-18 | General Electric Company | Process for reducing the residual chloride concentration in copper containing solids |
| US5945497A (en) * | 1997-12-22 | 1999-08-31 | Dow Corning Corporation | Method for hydrolyzing organochlorosilanes |
| US6075109A (en) * | 1998-12-17 | 2000-06-13 | Dow Corning Corporation | Method of forming a granular siloxane gel having reduced chloride content |
| EP2909217B1 (en) * | 2012-10-16 | 2016-10-26 | Dow Corning Corporation | Method of preparing halogenated silahydrocarbylenes |
| CN103550902B (zh) * | 2013-10-29 | 2015-09-30 | 江西星火狮达科技有限公司 | 有机硅浆渣的水解再生环保工艺 |
| CN103553051B (zh) * | 2013-10-29 | 2015-06-17 | 泸州北方化学工业有限公司 | 一种有机硅生产过程中浆渣固液分离的方法 |
| CN103951691B (zh) * | 2014-05-16 | 2017-01-18 | 吴娟 | 一种回收氯硅烷渣浆残液制备硅酸酯的方法 |
| CN117871351A (zh) * | 2023-12-06 | 2024-04-12 | 湖北兴瑞硅材料有限公司 | 一种有机硅浆渣中硅渣粒径的测定方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398672A (en) * | 1942-08-21 | 1946-04-16 | Gen Electric | Method of preparing organopolysiloxanes |
| US2483209A (en) * | 1945-11-21 | 1949-09-27 | Gen Electric | Method for hydrolyzing chlorosilanes and preparing polysiloxane resins |
| US2470497A (en) * | 1945-11-21 | 1949-05-17 | Gen Electric | Preparation of polysiloxane resins |
| US3090765A (en) * | 1959-07-16 | 1963-05-21 | Wacker Chemie Gmbh | Method of hydrolyzing chlorosilanes |
| FR1498915A (fr) | 1965-11-10 | 1967-10-20 | Dow Corning | Compositions auto-émulsionnables utiles pour la stabilisation du sol |
-
1979
- 1979-02-16 US US06/012,684 patent/US4221691A/en not_active Expired - Lifetime
- 1979-11-08 CA CA339,435A patent/CA1105799A/en not_active Expired
- 1979-12-12 AU AU53760/79A patent/AU525768B2/en not_active Ceased
-
1980
- 1980-01-11 JP JP55002019A patent/JPS5827810B2/ja not_active Expired
- 1980-01-30 BR BR8000578A patent/BR8000578A/pt unknown
- 1980-02-06 GB GB8003921A patent/GB2043089B/en not_active Expired
- 1980-02-14 FR FR8003278A patent/FR2449095A1/fr active Granted
- 1980-02-15 BE BE0/199418A patent/BE881749A/fr not_active IP Right Cessation
- 1980-02-15 DE DE3005743A patent/DE3005743C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE881749A (fr) | 1980-08-18 |
| GB2043089B (en) | 1983-01-26 |
| AU525768B2 (en) | 1982-12-02 |
| DE3005743C2 (de) | 1982-06-03 |
| FR2449095B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-01-07 |
| GB2043089A (en) | 1980-10-01 |
| BR8000578A (pt) | 1980-10-21 |
| US4221691A (en) | 1980-09-09 |
| FR2449095A1 (fr) | 1980-09-12 |
| DE3005743A1 (de) | 1980-08-21 |
| AU5376079A (en) | 1980-08-21 |
| JPS55110122A (en) | 1980-08-25 |
| JPS5827810B2 (ja) | 1983-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |