DE1545800C3 - Verfahren zur Herstellung von 4 Alkyl 2,2 dimethyl 2 silamorpholinen - Google Patents
Verfahren zur Herstellung von 4 Alkyl 2,2 dimethyl 2 silamorpholinenInfo
- Publication number
- DE1545800C3 DE1545800C3 DE1545800A DE1545800A DE1545800C3 DE 1545800 C3 DE1545800 C3 DE 1545800C3 DE 1545800 A DE1545800 A DE 1545800A DE 1545800 A DE1545800 A DE 1545800A DE 1545800 C3 DE1545800 C3 DE 1545800C3
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- mol
- silamorpholinen
- dimethyl
- benzene
- 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 description 14
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 title 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical class C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 50
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- -1 B. ether Chemical compound 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GGPLWEZGITVTJX-UHFFFAOYSA-N 2,2,4-trimethyl-1,4,2-oxazasilinane Chemical compound CN1CCO[Si](C)(C)C1 GGPLWEZGITVTJX-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- PWGDSJHHIZNBKL-UHFFFAOYSA-N 1,4,2-oxazasilinane Chemical compound C1CO[SiH2]CN1 PWGDSJHHIZNBKL-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- CNTRZROSTQPQPP-UHFFFAOYSA-N bromomethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CBr CNTRZROSTQPQPP-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- CAURZYXCQQWBJO-UHFFFAOYSA-N bromomethyl-chloro-dimethylsilane Chemical compound C[Si](C)(Cl)CBr CAURZYXCQQWBJO-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QLUIJRRNPIJBLV-UHFFFAOYSA-N 2,2-dimethyl-1,4,2-oxazasilinane Chemical compound C[Si]1(C)CNCCO1 QLUIJRRNPIJBLV-UHFFFAOYSA-N 0.000 description 1
- ALRZIDZLNAJGMX-UHFFFAOYSA-N 2,2-dimethyl-4-propyl-1,4,2-oxazasilinane Chemical compound C[Si]1(CN(CCO1)CCC)C ALRZIDZLNAJGMX-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- AZEHWRUKRREOQS-UHFFFAOYSA-N C[Si]1(CN(CCO1)CC)C Chemical compound C[Si]1(CN(CCO1)CC)C AZEHWRUKRREOQS-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- KPNPHFUAQXMPST-UHFFFAOYSA-N [C].N1CCOCC1 Chemical class [C].N1CCOCC1 KPNPHFUAQXMPST-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- ZZRGHKUNLAYDTC-UHFFFAOYSA-N ethoxy(methyl)silane Chemical compound CCO[SiH2]C ZZRGHKUNLAYDTC-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical class [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004448 titration Methods 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
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0045715 | 1965-04-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1545800A1 DE1545800A1 (de) | 1969-07-31 |
| DE1545800B2 DE1545800B2 (de) | 1973-05-17 |
| DE1545800C3 true DE1545800C3 (de) | 1973-12-13 |
Family
ID=7100628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1545800A Expired DE1545800C3 (de) | 1965-04-03 | 1965-04-03 | Verfahren zur Herstellung von 4 Alkyl 2,2 dimethyl 2 silamorpholinen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3448137A (en18) |
| BE (1) | BE678852A (en18) |
| DE (1) | DE1545800C3 (en18) |
| GB (1) | GB1071309A (en18) |
| NL (1) | NL147738B (en18) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2032186A1 (de) * | 1970-06-30 | 1972-01-13 | Bayer | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen mit Hilfe von modifizierten Silamorpholinen |
| US4208408A (en) * | 1978-03-06 | 1980-06-17 | Sandoz, Inc. | Substituted 1-oxa-4-aza-2,6-disilacyclohexanes |
| JPS6172077A (ja) * | 1984-09-14 | 1986-04-14 | Shin Etsu Chem Co Ltd | 接着促進剤 |
| US4794192A (en) * | 1987-07-06 | 1988-12-27 | General Electric Company | Cyclic aminoalkylsilanes and their use as adhesion promoters in room temperature vulcanizable polydiorganosiloxane compositions |
| JP5835116B2 (ja) * | 2012-06-15 | 2015-12-24 | 信越化学工業株式会社 | アミノ基と保護された水酸基を有する有機ケイ素化合物及びその製造方法 |
-
1965
- 1965-04-03 DE DE1545800A patent/DE1545800C3/de not_active Expired
-
1966
- 1966-03-15 GB GB11278/66A patent/GB1071309A/en not_active Expired
- 1966-03-18 NL NL666603595A patent/NL147738B/xx not_active IP Right Cessation
- 1966-03-24 US US536985A patent/US3448137A/en not_active Expired - Lifetime
- 1966-04-01 BE BE678852D patent/BE678852A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1545800A1 (de) | 1969-07-31 |
| DE1545800B2 (de) | 1973-05-17 |
| BE678852A (en18) | 1966-09-10 |
| NL147738B (nl) | 1975-11-17 |
| US3448137A (en) | 1969-06-03 |
| NL6603595A (en18) | 1966-10-04 |
| GB1071309A (en) | 1967-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |