DE2360406A1 - Herstellung von beta-alkoxy-omegalactamen - Google Patents
Herstellung von beta-alkoxy-omegalactamenInfo
- Publication number
- DE2360406A1 DE2360406A1 DE2360406A DE2360406A DE2360406A1 DE 2360406 A1 DE2360406 A1 DE 2360406A1 DE 2360406 A DE2360406 A DE 2360406A DE 2360406 A DE2360406 A DE 2360406A DE 2360406 A1 DE2360406 A1 DE 2360406A1
- Authority
- DE
- Germany
- Prior art keywords
- beta
- omega
- alkoxy
- amino
- grams
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 14
- -1 amino ester Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001916 cyano esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007363 ring formation reaction Methods 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- WMIMDERMRVSNPB-UHFFFAOYSA-N 4-methoxyazepan-2-one Chemical compound COC1CCCNC(=O)C1 WMIMDERMRVSNPB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- ZOGNPJHCXKAYAJ-UHFFFAOYSA-N 3-bromoazepan-2-one Chemical compound BrC1CCCCNC1=O ZOGNPJHCXKAYAJ-UHFFFAOYSA-N 0.000 description 1
- CGFGIKNLZTZJDE-UHFFFAOYSA-N 4-oxobutanenitrile Chemical compound O=CCCC#N CGFGIKNLZTZJDE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D227/00—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
- C07D227/02—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D227/06—Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D227/08—Oxygen atoms
- C07D227/087—One doubly-bound oxygen atom in position 2, e.g. lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7216662A NL7216662A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-12-08 | 1972-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2360406A1 true DE2360406A1 (de) | 1974-06-12 |
Family
ID=19817506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2360406A Pending DE2360406A1 (de) | 1972-12-08 | 1973-12-04 | Herstellung von beta-alkoxy-omegalactamen |
Country Status (8)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138400A (en) * | 1975-12-20 | 1979-02-06 | Hoechst Aktiengesellschaft | Omega-alkoxy derivatives of lactams |
| US4250093A (en) * | 1979-06-29 | 1981-02-10 | The Standard Oil Company (Ohio) | Process for the preparation of laotams |
| US4470928A (en) * | 1981-10-15 | 1984-09-11 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing cyanovaleric esters and caprolactam |
| JPS61113949A (ja) * | 1984-11-06 | 1986-05-31 | 松下電工株式会社 | 外装材 |
| JPS6385727U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1986-11-26 | 1988-06-04 | ||
| GB2418425B (en) * | 2004-08-11 | 2008-09-03 | Univ Cambridge Tech | Anti-inflammatory agents |
| US11061084B2 (en) | 2019-03-07 | 2021-07-13 | Allegro Microsystems, Llc | Coil actuated pressure sensor and deflectable substrate |
| FR3140107B1 (fr) | 2022-09-27 | 2025-03-28 | Psa Automobiles Sa | Procédé et dispositif d’ouverture motorisée automatique d’un ouvrant d’un véhicule automobile |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2071253A (en) * | 1935-01-02 | 1937-02-16 | Du Pont | Linear condensation polymers |
| FR1233177A (fr) * | 1958-06-14 | 1960-10-12 | Bombrini Parodi Delfino | Procédé pour préparer l'acide 2-hydroxy-6-amino-hexanoïque, son lactame et des copolymères polyamidiques de celui-ci, et produits obtenus par ce procédé |
| US3485821A (en) * | 1967-05-29 | 1969-12-23 | Techni Chem Co The | Process for preparing caprolactam and its alkyl substituted derivatives |
| US3562254A (en) * | 1969-04-24 | 1971-02-09 | Techni Chem Co The | Production of caprolactam starting with cyclohexanone |
-
1972
- 1972-12-08 NL NL7216662A patent/NL7216662A/xx unknown
-
1973
- 1973-12-04 DE DE2360406A patent/DE2360406A1/de active Pending
- 1973-12-05 US US422007A patent/US3919197A/en not_active Expired - Lifetime
- 1973-12-06 BE BE138599A patent/BE808316A/xx unknown
- 1973-12-06 GB GB5652873A patent/GB1390699A/en not_active Expired
- 1973-12-07 JP JP48137295A patent/JPS5029571A/ja active Pending
- 1973-12-07 FR FR7343701A patent/FR2209756B1/fr not_active Expired
- 1973-12-07 IT IT54152/73A patent/IT1000228B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| US3919197A (en) | 1975-11-11 |
| FR2209756A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-05 |
| JPS5029571A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-25 |
| IT1000228B (it) | 1976-03-30 |
| NL7216662A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-11 |
| FR2209756B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-12 |
| BE808316A (fr) | 1974-06-06 |
| GB1390699A (en) | 1975-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2207699A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2721264A1 (de) | Verfahren zur herstellung von di-n- propylessigsaeure | |
| DE1695753A1 (de) | Verbesserungen in der Herstellung von 4-Oxopiperidinverbindungen und gewisser neuer 4-Oxopiperidinverbindungen | |
| DE2505902C2 (de) | Verfahren zur Herstellung von 2,5- Dimethyl-3-(2H)-furanon | |
| DE2360406A1 (de) | Herstellung von beta-alkoxy-omegalactamen | |
| DE1493898B (de) | Verfahren zur Herstellung von omega, omega'-Diaminoalkanen | |
| DE2447824A1 (de) | Herstellung von c tief 1 -c tief 7 aliphatischen hydrocarbylestern von n- eckige klammer auf 2,6-di(c tief 1 -c tief 7 -alkyl)phenyl eckige klammer zu alpha-aminocarbonsaeuren | |
| DE1668571A1 (de) | Herstellung von 2-Methylpolycyclomethylaminen | |
| DE69519388T2 (de) | Verfahren zur herstellung von 2-(omega-alkoxycarbonylalkanoyl)-4-butanolid und langkettiger omega-hydroxycarbonsäure | |
| DE2163539C3 (de) | Herstellung von Epsilon-Caprolactam und O-Acetylcyclohexanonoxim | |
| DE2439947A1 (de) | Verfahren zur herstellung von antimonglykoloxyd | |
| DE2721265C2 (de) | Verfahren zur Herstellung von Di- n-propylacetonitril | |
| DE69414251T2 (de) | Verfahren zur herstellung von einer omega-funktionalisierten aliphatischen carbonsäure | |
| DE2831555C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE69606389T2 (de) | Tricyclocarboxylate, verfahren zur herstellung sowie darauf basierendes parfum | |
| CH378868A (de) | Verfahren zur Herstellung des w-Amino-caprylsäureamids | |
| DE1568383C3 (de) | Verfahren zur Herstellung von ungesättigten carbonylgruppenhaltigen Nitrilen | |
| DE2164662A1 (de) | Indanderivate und Verfahren zu ihrer Herstellung | |
| DE1593477A1 (de) | Verfahren zur herstellung von gammabrom-beta-alkoxycrotonaten | |
| DE2547223C3 (de) | Verfahren zur Herstellung von 2,6,6-Trimethyl-cyclohex-2-en-1 -on | |
| DE2360407A1 (de) | Herstellung von omega-amino-betaalkoxycarbonsauren estern | |
| DE960813C (de) | Verfahren zur Herstellung von ungesaettigten ª†- und ª€-Laktonen | |
| DE2142401C3 (de) | Verfahren zur Herstellung von epsilon-Caprolactam und O-Acetylcyclohexanonoxim | |
| DE2443080C3 (de) | Verfahren zur Herstellung von ' 2,4-Diamino-5-(3',4'3'-triinethoxybenzyl)-pyrhnidin | |
| DE2426863A1 (de) | Verfahren zur spaltung von cycloaliphatischen hdroperoxiden |