CA1067090A - Process for the esterification of chlorosilanes - Google Patents
Process for the esterification of chlorosilanesInfo
- Publication number
- CA1067090A CA1067090A CA257,515A CA257515A CA1067090A CA 1067090 A CA1067090 A CA 1067090A CA 257515 A CA257515 A CA 257515A CA 1067090 A CA1067090 A CA 1067090A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- mol
- ilane
- alcohols
- esterification
- 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 20
- 230000032050 esterification Effects 0.000 title claims abstract description 9
- 238000005886 esterification reaction Methods 0.000 title claims abstract description 9
- 239000005046 Chlorosilane Substances 0.000 title description 7
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 title description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000001298 alcohols Chemical class 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 3
- 150000003138 primary alcohols Chemical class 0.000 claims abstract 2
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 6
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims description 4
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 claims description 4
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 3
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 3
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 claims description 2
- OOXSLJBUMMHDKW-UHFFFAOYSA-N trichloro(3-chloropropyl)silane Chemical compound ClCCC[Si](Cl)(Cl)Cl OOXSLJBUMMHDKW-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 150000004756 silanes Chemical class 0.000 abstract description 4
- 239000003755 preservative agent Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 9
- 229940012189 methyl orange Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- -1 alkyl radical Chemical class 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 229950011008 tetrachloroethylene Drugs 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000228957 Ferula foetida Species 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FORHPIYYTQZPDW-UHFFFAOYSA-N ethyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](CC)(OCCOC)OCCOC FORHPIYYTQZPDW-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000009991 pite Nutrition 0.000 description 1
- 244000293655 pite Species 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- YZORUOZKRBVLEG-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 YZORUOZKRBVLEG-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- 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
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2532887A DE2532887C2 (de) | 1975-07-23 | 1975-07-23 | Verfahren zur Veresterung von Halogensilanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1067090A true CA1067090A (en) | 1979-11-27 |
Family
ID=5952229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA257,515A Expired CA1067090A (en) | 1975-07-23 | 1976-07-22 | Process for the esterification of chlorosilanes |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5949228B2 (cs) |
| BE (1) | BE844278A (cs) |
| CA (1) | CA1067090A (cs) |
| CH (1) | CH606038A5 (cs) |
| DD (1) | DD125707A5 (cs) |
| DE (1) | DE2532887C2 (cs) |
| FR (1) | FR2318873A1 (cs) |
| GB (1) | GB1549009A (cs) |
| IT (1) | IT1066001B (cs) |
| NL (1) | NL7608134A (cs) |
| PL (1) | PL103000B1 (cs) |
| SU (1) | SU1233802A3 (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2800017C2 (de) * | 1978-01-02 | 1983-05-26 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Organoalkoxysilanen |
| US4172805A (en) * | 1978-02-27 | 1979-10-30 | Dow Corning Corporation | Benzyloxy endblocked organosilicon dielectric fluids and electrical devices containing same |
| JPS59104899A (ja) * | 1982-12-08 | 1984-06-16 | Kita Nippon Onkyo Kk | スピ−カの磁気回路の組立方法 |
| DE19755597A1 (de) * | 1997-12-15 | 1999-06-17 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Alkoxysilanen |
| RU2320666C1 (ru) * | 2007-01-09 | 2008-03-27 | Открытое акционерное общество "Химпром" | Способ получения алкоксисиланов |
| RU2352574C1 (ru) * | 2007-09-24 | 2009-04-20 | Открытое акционерное общество "Химпром" | Способ получения октилтриэтоксисилана |
| RU2565675C1 (ru) * | 2014-05-30 | 2015-10-20 | Федеральное государственное бюджетное учреждение науки Институт синтетических полимерных материалов им. Ениколопова Российской Академии Наук (ИСПМ РАН) | Способ получения метилбензилалкоксисиланов |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701803A (en) * | 1948-10-20 | 1955-02-08 | Socony Vacuum Oil Co Inc | Synthetic lubricants |
| BE814011A (en) * | 1971-11-03 | 1974-08-16 | Organosilanes prepn. from halo- or aminosilanes - by reaction with hydroxy or carboxy cpds. in pentane | |
| DE2409731C2 (de) * | 1974-03-01 | 1983-05-26 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Veresterung von Trichlorsilan |
-
1975
- 1975-07-23 DE DE2532887A patent/DE2532887C2/de not_active Expired
-
1976
- 1976-07-19 BE BE169028A patent/BE844278A/xx not_active IP Right Cessation
- 1976-07-21 GB GB3047276A patent/GB1549009A/en not_active Expired
- 1976-07-21 PL PL19133676A patent/PL103000B1/pl unknown
- 1976-07-21 IT IT5054076A patent/IT1066001B/it active
- 1976-07-22 DD DD19401576A patent/DD125707A5/xx unknown
- 1976-07-22 JP JP8770776A patent/JPS5949228B2/ja not_active Expired
- 1976-07-22 CA CA257,515A patent/CA1067090A/en not_active Expired
- 1976-07-22 CH CH942676A patent/CH606038A5/xx not_active IP Right Cessation
- 1976-07-22 NL NL7608134A patent/NL7608134A/xx not_active Application Discontinuation
- 1976-07-22 FR FR7622413A patent/FR2318873A1/fr active Granted
-
1980
- 1980-09-10 SU SU802979302A patent/SU1233802A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1549009A (en) | 1979-08-01 |
| SU1233802A3 (ru) | 1986-05-23 |
| FR2318873B1 (cs) | 1982-11-19 |
| CH606038A5 (cs) | 1978-10-13 |
| JPS5214728A (en) | 1977-02-03 |
| NL7608134A (nl) | 1977-01-25 |
| DD125707A5 (cs) | 1977-05-11 |
| IT1066001B (it) | 1985-03-04 |
| BE844278A (fr) | 1976-11-16 |
| PL103000B1 (pl) | 1979-05-31 |
| DE2532887B1 (de) | 1976-07-01 |
| JPS5949228B2 (ja) | 1984-12-01 |
| DE2532887C2 (de) | 1982-10-14 |
| FR2318873A1 (fr) | 1977-02-18 |
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