CA1282421C - Process for preparing triacetoxysilanes from tris(amino)silanes - Google Patents
Process for preparing triacetoxysilanes from tris(amino)silanesInfo
- Publication number
- CA1282421C CA1282421C CA000499750A CA499750A CA1282421C CA 1282421 C CA1282421 C CA 1282421C CA 000499750 A CA000499750 A CA 000499750A CA 499750 A CA499750 A CA 499750A CA 1282421 C CA1282421 C CA 1282421C
- Authority
- CA
- Canada
- Prior art keywords
- silane
- tris
- amino
- reaction
- acetic anhydride
- 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
- DDSWIYVVHBOISO-UHFFFAOYSA-N ctk0i1982 Chemical class N[SiH](N)N DDSWIYVVHBOISO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 81
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- FHBURLBCXNMPJX-UHFFFAOYSA-N n-[bis(dimethylamino)-ethylsilyl]-n-methylmethanamine Chemical group CC[Si](N(C)C)(N(C)C)N(C)C FHBURLBCXNMPJX-UHFFFAOYSA-N 0.000 claims description 5
- AHKKZIUZTWZKDR-UHFFFAOYSA-N n-[bis(dimethylamino)-methylsilyl]-n-methylmethanamine Chemical group CN(C)[Si](C)(N(C)C)N(C)C AHKKZIUZTWZKDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- WBVXRXLWILVPMX-UHFFFAOYSA-N n-[bis(dimethylamino)-ethenylsilyl]-n-methylmethanamine Chemical group CN(C)[Si](C=C)(N(C)C)N(C)C WBVXRXLWILVPMX-UHFFFAOYSA-N 0.000 claims description 2
- GIRKRMUMWJFNRI-UHFFFAOYSA-N tris(dimethylamino)silicon Chemical group CN(C)[Si](N(C)C)N(C)C GIRKRMUMWJFNRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Chemical group 0.000 claims description 2
- -1 AMINO Chemical class 0.000 description 33
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000376 reactant Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 229910000077 silane Inorganic materials 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- UQMGAWUIVYDWBP-UHFFFAOYSA-N silyl acetate Chemical class CC(=O)O[SiH3] UQMGAWUIVYDWBP-UHFFFAOYSA-N 0.000 description 4
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 description 3
- KXJLGCBCRCSXQF-UHFFFAOYSA-N [diacetyloxy(ethyl)silyl] acetate Chemical compound CC(=O)O[Si](CC)(OC(C)=O)OC(C)=O KXJLGCBCRCSXQF-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical group CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical group C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 1
- 238000006137 acetoxylation reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
- C07F7/1896—Compounds having one or more Si-O-acyl 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
- C07F7/025—Silicon compounds without C-silicon linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/694,307 US4556725A (en) | 1985-01-24 | 1985-01-24 | Process for preparing triacetoxysilanes from tris(amino)silanes |
| US694,307 | 1985-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1282421C true CA1282421C (en) | 1991-04-02 |
Family
ID=24788279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000499750A Expired - Lifetime CA1282421C (en) | 1985-01-24 | 1986-01-16 | Process for preparing triacetoxysilanes from tris(amino)silanes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4556725A (enExample) |
| EP (1) | EP0189839B1 (enExample) |
| JP (1) | JPS61172886A (enExample) |
| AT (1) | ATE41426T1 (enExample) |
| AU (1) | AU585306B2 (enExample) |
| BR (1) | BR8600260A (enExample) |
| CA (1) | CA1282421C (enExample) |
| DE (1) | DE3662398D1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4112650A1 (de) * | 1991-04-18 | 1992-10-22 | Huels Chemische Werke Ag | Verfahren zur gleichzeitigen und kontinuierlichen herstellung von carbonoyloxysilanen und carbonsaeurechloriden |
| JPH05220600A (ja) * | 1992-02-10 | 1993-08-31 | Japan Steel Works Ltd:The | 摩擦クランプ装置の滑り予知方法およびその装置 |
| US5902892A (en) * | 1996-10-17 | 1999-05-11 | Sivento Inc. | Preparation of acyloxysilanes |
| WO2004056837A1 (en) * | 2002-12-20 | 2004-07-08 | Sigma Coatings B.V. | Process for the production of hydrocarbyl silyl carboxylate compounds |
| US8318966B2 (en) * | 2006-06-23 | 2012-11-27 | Praxair Technology, Inc. | Organometallic compounds |
| US10287490B2 (en) | 2012-10-25 | 2019-05-14 | Lumileds Llc | PDMS-based ligands for quantum dots in silicones |
| US10035952B2 (en) | 2012-10-25 | 2018-07-31 | Lumileds Llc | PDMS-based ligands for quantum dots in silicones |
| KR20250019125A (ko) | 2022-06-02 | 2025-02-07 | 젤리스트 인코퍼레이티드 | 고순도 알킬 주석 화합물 및 이의 제조 방법 |
| TW202413383A (zh) | 2022-08-12 | 2024-04-01 | 美商蓋列斯特股份有限公司 | 含不飽和取代基之高純度錫化合物及其製造方法 |
| US12606577B2 (en) | 2022-09-28 | 2026-04-21 | Gelest, Inc. | Iodoalkyl tin compounds and preparation methods thereof |
| CN119998302A (zh) | 2022-10-04 | 2025-05-13 | 盖列斯特有限公司 | 环状氮杂锡烷和环状氧杂锡烷化合物及其制备方法 |
| WO2025115332A1 (ja) | 2023-12-01 | 2025-06-05 | 三菱ケミカル株式会社 | スズ化合物およびそれを用いたレジスト溶液、パターン形成方法、薄膜、パターン化された薄膜、並びにスズ化合物の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623832A (en) * | 1946-09-20 | 1952-12-30 | Montclair Res Corp | Polymerizing silicon acylates |
| US2634285A (en) * | 1947-03-27 | 1953-04-07 | Montclair Res Corp | Acyloxy silanes |
| US2866800A (en) * | 1951-01-08 | 1958-12-30 | Montclair Res Corp | Substituted silicon acylates |
| FR1541542A (fr) * | 1966-10-20 | 1968-10-04 | Gen Electric | Acyloxyaminosilanes |
| DE2801780A1 (de) * | 1978-01-17 | 1979-07-19 | Wacker Chemie Gmbh | Verfahren zum herstellen von acyloxysilanen und gegebenenfalls acyloxysiloxanen |
| US4360686A (en) * | 1981-09-03 | 1982-11-23 | The Dow Chemical Company | Silylation of organic compounds |
-
1985
- 1985-01-24 US US06/694,307 patent/US4556725A/en not_active Expired - Fee Related
-
1986
- 1986-01-16 CA CA000499750A patent/CA1282421C/en not_active Expired - Lifetime
- 1986-01-23 BR BR8600260A patent/BR8600260A/pt unknown
- 1986-01-23 DE DE8686100853T patent/DE3662398D1/de not_active Expired
- 1986-01-23 AU AU52675/86A patent/AU585306B2/en not_active Ceased
- 1986-01-23 EP EP86100853A patent/EP0189839B1/en not_active Expired
- 1986-01-23 AT AT86100853T patent/ATE41426T1/de not_active IP Right Cessation
- 1986-01-23 JP JP61011220A patent/JPS61172886A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6357434B2 (enExample) | 1988-11-11 |
| EP0189839A1 (en) | 1986-08-06 |
| AU585306B2 (en) | 1989-06-15 |
| EP0189839B1 (en) | 1989-03-15 |
| BR8600260A (pt) | 1986-10-07 |
| JPS61172886A (ja) | 1986-08-04 |
| ATE41426T1 (de) | 1989-04-15 |
| AU5267586A (en) | 1986-07-31 |
| DE3662398D1 (en) | 1989-04-20 |
| US4556725A (en) | 1985-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |