DE69230989T2 - Durch anorganische Säure katalysierte Verfahren zur Silylierung - Google Patents
Durch anorganische Säure katalysierte Verfahren zur SilylierungInfo
- Publication number
- DE69230989T2 DE69230989T2 DE69230989T DE69230989T DE69230989T2 DE 69230989 T2 DE69230989 T2 DE 69230989T2 DE 69230989 T DE69230989 T DE 69230989T DE 69230989 T DE69230989 T DE 69230989T DE 69230989 T2 DE69230989 T2 DE 69230989T2
- Authority
- DE
- Germany
- Prior art keywords
- product
- colorless
- inorganic acid
- alcohol
- ammonia
- 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
- 150000007522 mineralic acids Chemical class 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 17
- 238000006884 silylation reaction Methods 0.000 title description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 8
- WGGNJZRNHUJNEM-UHFFFAOYSA-N 2,2,4,4,6,6-hexamethyl-1,3,5,2,4,6-triazatrisilinane Chemical compound C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N1 WGGNJZRNHUJNEM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 57
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 56
- 229910021529 ammonia Inorganic materials 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003377 acid catalyst Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 230000005587 bubbling Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 2,4,4-trimethylpentyl Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001139 pH measurement Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- JROMGTZTUZNJJY-UHFFFAOYSA-N 1,3,5-tris(ethenyl)-2,4,6-trimethyl-1,3,5,2,4,6-triazatrisilinane Chemical compound C(=C)N1[SiH](N([SiH](N([SiH]1C)C=C)C)C=C)C JROMGTZTUZNJJY-UHFFFAOYSA-N 0.000 description 1
- FIADVASZMLCQIF-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octamethyl-1,3,5,7,2,4,6,8-tetrazatetrasilocane Chemical compound C[Si]1(C)N[Si](C)(C)N[Si](C)(C)N[Si](C)(C)N1 FIADVASZMLCQIF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- VJFUNCKASZQOPO-UHFFFAOYSA-N N-dioctylsilyl-N-trimethylsilylmethanamine Chemical compound CCCCCCCC[SiH](N(C)[Si](C)(C)C)CCCCCCCC VJFUNCKASZQOPO-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- HIMXYMYMHUAZLW-UHFFFAOYSA-N [[[dimethyl(phenyl)silyl]amino]-dimethylsilyl]benzene Chemical compound C=1C=CC=CC=1[Si](C)(C)N[Si](C)(C)C1=CC=CC=C1 HIMXYMYMHUAZLW-UHFFFAOYSA-N 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- QYJHBNLRANFWHO-UHFFFAOYSA-N [ethenyl-[(ethenyl-methyl-phenylsilyl)amino]-methylsilyl]benzene Chemical compound C=1C=CC=CC=1[Si](C)(C=C)N[Si](C)(C=C)C1=CC=CC=C1 QYJHBNLRANFWHO-UHFFFAOYSA-N 0.000 description 1
- YFONAHAKNVIHPT-UHFFFAOYSA-N [methyl-[[methyl(diphenyl)silyl]amino]-phenylsilyl]benzene Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)N[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 YFONAHAKNVIHPT-UHFFFAOYSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SXSNZRHGAMVNJE-UHFFFAOYSA-N chloro-[[[chloromethyl(dimethyl)silyl]amino]-dimethylsilyl]methane Chemical compound ClC[Si](C)(C)N[Si](C)(C)CCl SXSNZRHGAMVNJE-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax 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
- C07F7/18—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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/770,376 US5157139A (en) | 1991-10-03 | 1991-10-03 | Inorganic acid catalysed silylation reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69230989D1 DE69230989D1 (de) | 2000-06-08 |
| DE69230989T2 true DE69230989T2 (de) | 2000-11-16 |
Family
ID=25088341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69230989T Expired - Lifetime DE69230989T2 (de) | 1991-10-03 | 1992-10-01 | Durch anorganische Säure katalysierte Verfahren zur Silylierung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5157139A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0535947B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH05247061A (cg-RX-API-DMAC7.html) |
| KR (1) | KR100242750B1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU648200B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2079542A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69230989T2 (cg-RX-API-DMAC7.html) |
| TW (1) | TW238311B (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326557A (en) * | 1993-04-06 | 1994-07-05 | Dow Corning Corporation | Moisturizing compositions containing organosilicon compounds |
| US5707550A (en) * | 1993-04-06 | 1998-01-13 | Dow Corning Corporation | Foam boosting of hair shampoo compositions |
| US6017546A (en) * | 1993-07-06 | 2000-01-25 | Dow Corning Corporation | Water-in-volatile silicone emulsion gel cosmetic |
| US5847179A (en) * | 1997-10-02 | 1998-12-08 | Pcr, Inc. | High purity alkoxytrimethylsilane fluids |
| JP2003252879A (ja) * | 2001-12-25 | 2003-09-10 | Nippon Shokubai Co Ltd | アルコキシシランの製造方法 |
| US9263769B2 (en) * | 2014-04-30 | 2016-02-16 | Uchicago Argonne, Llc | Process for the production of low flammability electrolyte solvents |
| BR112017008787A2 (pt) | 2014-10-28 | 2017-12-26 | 3M Innovative Properties Co | componentes de um sistema de aplicação de aspersões que compreende uma superfície repelente & métodos |
| CN108350290B (zh) | 2015-10-28 | 2021-10-15 | 3M创新有限公司 | 包括拒斥性表面的经历冰形成的制品 |
| AU2016346920B2 (en) | 2015-10-28 | 2020-04-30 | 3M Innovative Properties Company | Spray application system components comprising a repellent surface and methods |
| US10907070B2 (en) | 2016-04-26 | 2021-02-02 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface comprising a siloxane material |
| EP4190793B1 (en) * | 2020-07-31 | 2025-01-08 | Lg Chem, Ltd. | Method of manufacturing alkoxysilane compound |
| KR102763692B1 (ko) * | 2020-07-31 | 2025-02-07 | 주식회사 엘지화학 | 알콕시실란 화합물의 제조방법 |
| CN114524839B (zh) * | 2022-01-12 | 2024-06-25 | 湖北江瀚新材料股份有限公司 | 一种硬脂氧基三甲基硅烷的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1568558A1 (de) * | 1966-07-26 | 1970-03-19 | Bayer Ag | N-Methylolsilylaether |
| US3636026A (en) * | 1968-11-06 | 1972-01-18 | Bayer Ag | Benzoin-silyl-esters |
| US3664937A (en) * | 1968-11-06 | 1972-05-23 | Bayer Ag | Photosensitizing molding and coating compositions with benzoin-silyl-esters |
| GB2009193B (en) * | 1977-11-24 | 1982-03-17 | Dow Corning Ltd | Silylation process |
| DE3911917A1 (de) * | 1989-04-12 | 1990-10-18 | Hoechst Ag | Verfahren zur herstellung von alkoxysilanen, die praktisch frei sind von halogenverbindungen, verwendung dieser alkoxysilane und hydraulische fluessigkeiten, die diese alkoxysilane enthalten |
-
1991
- 1991-10-03 US US07/770,376 patent/US5157139A/en not_active Expired - Lifetime
-
1992
- 1992-09-30 CA CA002079542A patent/CA2079542A1/en not_active Abandoned
- 1992-10-01 DE DE69230989T patent/DE69230989T2/de not_active Expired - Lifetime
- 1992-10-01 EP EP92308942A patent/EP0535947B1/en not_active Expired - Lifetime
- 1992-10-02 KR KR1019920018063A patent/KR100242750B1/ko not_active Expired - Fee Related
- 1992-10-02 JP JP4264414A patent/JPH05247061A/ja active Pending
- 1992-10-02 TW TW081107846A patent/TW238311B/zh active
- 1992-10-02 AU AU26102/92A patent/AU648200B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05247061A (ja) | 1993-09-24 |
| EP0535947B1 (en) | 2000-05-03 |
| US5157139A (en) | 1992-10-20 |
| CA2079542A1 (en) | 1993-04-04 |
| TW238311B (cg-RX-API-DMAC7.html) | 1995-01-11 |
| AU2610292A (en) | 1993-04-08 |
| DE69230989D1 (de) | 2000-06-08 |
| KR930007957A (ko) | 1993-05-20 |
| AU648200B2 (en) | 1994-04-14 |
| EP0535947A1 (en) | 1993-04-07 |
| KR100242750B1 (ko) | 2000-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| R071 | Expiry of right |
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