NO115740B - - Google Patents
Download PDFInfo
- Publication number
- NO115740B NO115740B NO157788A NO15778865A NO115740B NO 115740 B NO115740 B NO 115740B NO 157788 A NO157788 A NO 157788A NO 15778865 A NO15778865 A NO 15778865A NO 115740 B NO115740 B NO 115740B
- Authority
- NO
- Norway
- Prior art keywords
- chloride
- reaction
- oxime
- temperature
- per cent
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
- 150000003951 lactams Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 150000002923 oximes Chemical class 0.000 description 8
- 238000006462 rearrangement reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- FSDCOFYXQALRJL-UHFFFAOYSA-N 1-chloroaziridine-2,3-dione Chemical compound ClN1C(=O)C1=O FSDCOFYXQALRJL-UHFFFAOYSA-N 0.000 description 2
- VGQNLFXKGSKQNA-UHFFFAOYSA-N 1-chloroaziridine-2,3-dione hydrochloride Chemical compound Cl.C1(C(N1Cl)=O)=O VGQNLFXKGSKQNA-UHFFFAOYSA-N 0.000 description 2
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AVSUHTJHZKMHNZ-UHFFFAOYSA-N 1-chloroazepane-2,7-dione Chemical compound ClN1C(=O)CCCCC1=O AVSUHTJHZKMHNZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 101800000021 N-terminal protease Proteins 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- NJNQUTDUIPVROZ-UHFFFAOYSA-N nitrocyclohexane Chemical compound [O-][N+](=O)C1CCCCC1 NJNQUTDUIPVROZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- -1 trichloromethylene Chemical compound 0.000 description 1
- 239000012808 vapor phase 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
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6404371A NL6404371A (fr) | 1964-04-22 | 1964-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115740B true NO115740B (fr) | 1968-11-25 |
Family
ID=19789884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157788A NO115740B (fr) | 1964-04-22 | 1965-04-21 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3365443A (fr) |
| AT (1) | AT252203B (fr) |
| BE (1) | BE662844A (fr) |
| CH (1) | CH452533A (fr) |
| DE (1) | DE1620470C3 (fr) |
| DK (1) | DK109515C (fr) |
| ES (1) | ES312068A1 (fr) |
| GB (1) | GB1090044A (fr) |
| IL (1) | IL23356A (fr) |
| NL (1) | NL6404371A (fr) |
| NO (1) | NO115740B (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL147425B (nl) * | 1965-04-06 | 1975-10-15 | Stamicarbon | Werkwijze voor het bereiden van omega-aminododecadieenzuurlactam uit cyclododeca-4,8-dienonoxime. |
| NL6910429A (fr) * | 1969-07-08 | 1971-01-12 | ||
| US7834618B2 (en) | 2007-06-27 | 2010-11-16 | Brooks Automation, Inc. | Position sensor system |
| CN110862329B (zh) * | 2019-11-18 | 2022-09-27 | 山东省化工研究院 | 一种7-氨基庚酸盐酸盐的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2221369A (en) * | 1940-11-12 | Process foe producing lactams | ||
| US2234566A (en) * | 1938-07-23 | 1941-03-11 | Du Pont | Catalytic process for the production of caprolactam, amino-capronitrile and hexamethylene diamine |
-
1964
- 1964-04-22 NL NL6404371A patent/NL6404371A/xx unknown
-
1965
- 1965-04-13 IL IL23356A patent/IL23356A/xx unknown
- 1965-04-14 GB GB16080/65A patent/GB1090044A/en not_active Expired
- 1965-04-15 AT AT351365A patent/AT252203B/de active
- 1965-04-15 DE DE1620470A patent/DE1620470C3/de not_active Expired
- 1965-04-15 CH CH532765A patent/CH452533A/de unknown
- 1965-04-19 US US449301A patent/US3365443A/en not_active Expired - Lifetime
- 1965-04-21 ES ES0312068A patent/ES312068A1/es not_active Expired
- 1965-04-21 BE BE662844D patent/BE662844A/xx unknown
- 1965-04-21 DK DK200865AA patent/DK109515C/da active
- 1965-04-21 NO NO157788A patent/NO115740B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620470C3 (de) | 1975-05-28 |
| GB1090044A (en) | 1967-11-08 |
| BE662844A (fr) | 1965-10-21 |
| NL6404371A (fr) | 1965-10-25 |
| DE1620470B2 (de) | 1974-10-03 |
| DK109515C (da) | 1968-05-06 |
| IL23356A (en) | 1968-12-26 |
| ES312068A1 (es) | 1966-02-01 |
| AT252203B (de) | 1967-02-10 |
| DE1620470A1 (de) | 1970-04-09 |
| CH452533A (de) | 1968-03-15 |
| US3365443A (en) | 1968-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2221369A (en) | Process foe producing lactams | |
| US3485821A (en) | Process for preparing caprolactam and its alkyl substituted derivatives | |
| US3462417A (en) | Refinements in the distillation of lactams from solutions thereof | |
| US2351381A (en) | Process for the conversion of | |
| NO157788B (no) | Fremgangsmte for redusering av mengden av partikkelformig materiale som dannes under forbrenning av en brennolje som inneholder et zirkoniumadditiv. | |
| NO115740B (fr) | ||
| US3437655A (en) | Lactams from cyclo-aliphatic ketoximes by the beckmann rearrangement employing hci as catalyst | |
| US2721199A (en) | Production of amides or lactams from oximes | |
| US3544562A (en) | Process for the manufacture of omega-decalactam using epsilon-caprolactam as a solvent therefor | |
| US2883377A (en) | Production of lactams from oxime | |
| RU1834885C (ru) | Способ очистки амидов, получаемых из оксимов при перегруппировке Бекмана | |
| US3063986A (en) | Process for the production of a | |
| NO153247B (no) | Tralle. | |
| DE69717976T2 (de) | Gewinnung von epsilon-caprolactam aus wässrigen gemischen | |
| US3428625A (en) | Process for the continuous manufacture of laurolactam in the liquid phase | |
| US3404148A (en) | Preparation of omega-laurinolactam | |
| US2737511A (en) | Extraction of lactam | |
| US3186984A (en) | Xanhydrous a ammonia | |
| US4170592A (en) | Purification of ε-caprolactam | |
| US2763686A (en) | Production of oximes | |
| US3127395A (en) | Process of separating lactams from beckmann | |
| US3265733A (en) | Production of oximes of cyclo- aliphatic ketones | |
| US3733317A (en) | Method for the preparation of omega-lactams and their lactamizable precursors | |
| US2447419A (en) | Preparation of diphenylacetonitrile | |
| US2569114A (en) | Their hydkolytic products |