CH456605A - Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flüssiger Phase - Google Patents
Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flüssiger PhaseInfo
- Publication number
- CH456605A CH456605A CH111766A CH111766A CH456605A CH 456605 A CH456605 A CH 456605A CH 111766 A CH111766 A CH 111766A CH 111766 A CH111766 A CH 111766A CH 456605 A CH456605 A CH 456605A
- Authority
- CH
- Switzerland
- Prior art keywords
- solvent
- lactam
- sulfuric acid
- oxime
- stage
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 15
- 239000007791 liquid phase Substances 0.000 title claims description 9
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 title claims description 7
- 238000010924 continuous production Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 78
- 239000002904 solvent Substances 0.000 claims description 65
- 150000003951 lactams Chemical class 0.000 claims description 54
- 150000002923 oximes Chemical class 0.000 claims description 36
- 238000000605 extraction Methods 0.000 claims description 28
- 230000007062 hydrolysis Effects 0.000 claims description 26
- 238000006460 hydrolysis reaction Methods 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 20
- 230000008707 rearrangement Effects 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000012071 phase Substances 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 239000002253 acid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000006146 oximation reaction Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000013021 overheating Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- GMUJGUXGVJZHSK-UHFFFAOYSA-N 1,4-di(propan-2-yl)cyclohexane Chemical compound CC(C)C1CCC(C(C)C)CC1 GMUJGUXGVJZHSK-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- -1 B. cyclohexanone Chemical class 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC0035001 | 1965-02-03 | ||
| DEC0036809 | 1965-09-06 | ||
| DEC0036810 | 1965-09-06 | ||
| DE1966C0038810 DE1524614B2 (de) | 1965-04-23 | 1966-04-19 | Verfahren und vorrichtung zur ermittlung und erhebung von parkgebuehren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH456605A true CH456605A (de) | 1968-07-31 |
Family
ID=27436711
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH112066A CH462818A (de) | 1965-02-03 | 1966-01-27 | Verfahren zur Aufarbeitung von lactamhaltigen Lösungen durch Destillation und Anwendung des Verfahrens |
| CH111766A CH456605A (de) | 1965-02-03 | 1966-01-27 | Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flüssiger Phase |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH112066A CH462818A (de) | 1965-02-03 | 1966-01-27 | Verfahren zur Aufarbeitung von lactamhaltigen Lösungen durch Destillation und Anwendung des Verfahrens |
Country Status (6)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725391A (en) * | 1970-11-30 | 1973-04-03 | Toray Industries | Process for the preparation of lactams from cycloalkanone oximes |
| US4610768A (en) * | 1985-12-02 | 1986-09-09 | The Firestone Tire & Rubber Company | Lactam purification |
| DE4019167A1 (de) * | 1990-06-15 | 1991-12-19 | Henkel Kgaa | Verfahren zur herstellung von metallseifen |
| US8163899B2 (en) * | 2007-02-09 | 2012-04-24 | National University Corporation Nagoya University | Process for producing laurolactam |
| US8309714B2 (en) | 2007-11-29 | 2012-11-13 | Ube Industries, Ltd. | Process for producing laurolactam |
| EP2292599B1 (en) * | 2008-05-20 | 2016-01-06 | Ube Industries, Ltd. | Process for producing laurolactam |
| ES2522824T3 (es) | 2009-03-04 | 2014-11-18 | Ube Industries, Ltd. | Método para la producción de un compuesto amida |
| WO2011037208A1 (ja) | 2009-09-24 | 2011-03-31 | 宇部興産株式会社 | 新規化合物およびそれを用いたアミド化合物の製造方法 |
| DE102009046910A1 (de) * | 2009-11-20 | 2011-05-26 | Evonik Degussa Gmbh | Verfahren zur Aufarbeitung eines Laurinlactam enthaltenen Stoffstroms für die Rückgewinnung aller enthaltene Wertstoffkomponenten durch Kombination von Kristallisation mit nachgeschalteter Destillation |
| KR102500501B1 (ko) | 2017-12-28 | 2023-02-16 | 한화솔루션 주식회사 | 라우로락탐의 제조 방법 및 이의 합성 장치 |
| CN109481958B (zh) * | 2018-11-29 | 2021-04-20 | 万华化学集团股份有限公司 | 一种降低环十二酮肟在硫酸萃取过程中的水解率的方法 |
| KR102499747B1 (ko) | 2018-12-19 | 2023-02-15 | 한화솔루션 주식회사 | 신규한 라우로락탐 제조 방법 및 합성 장치 |
| CN112479964B (zh) * | 2020-11-17 | 2022-07-26 | 万华化学集团股份有限公司 | 一种环十二酮肟发生萃取重排反应制备十二内酰胺的方法 |
| CN113769683B (zh) * | 2021-08-24 | 2023-04-18 | 北京化工大学 | 一种十二内酰胺的短流程连续化制备系统及方法 |
| CN115260073B (zh) * | 2022-08-31 | 2024-09-20 | 中国天辰工程有限公司 | 一种无硫酸铵副产重排工艺制备月桂精内酰胺的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2573374A (en) * | 1951-10-30 | Method for producing lagtams | ||
| US2752336A (en) * | 1956-06-26 | For the pu | ||
| US2249177A (en) * | 1941-07-15 | Rearrangement reaction of oxevies | ||
| US2692878A (en) * | 1954-10-26 | Method forithe continuous produc- | ||
| US2313026A (en) * | 1939-02-13 | 1943-03-02 | Schlack Paul | Process for the manufacture of lactams from oximes of cyclic ketones |
| US3060173A (en) * | 1958-05-30 | 1962-10-23 | Basf Ag | Production of omega-amino dodecane acid lactam |
| NL133986C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-01-30 |
-
1965
- 1965-09-06 DE DE1545697A patent/DE1545697C3/de not_active Expired
- 1965-09-06 DE DE1545696A patent/DE1545696C3/de not_active Expired
-
1966
- 1966-01-27 CH CH112066A patent/CH462818A/de unknown
- 1966-01-27 CH CH111766A patent/CH456605A/de unknown
- 1966-02-01 JP JP41005459A patent/JPS5233118B1/ja active Pending
- 1966-02-02 US US524395A patent/US3431255A/en not_active Expired - Lifetime
- 1966-02-02 GB GB4530/66A patent/GB1088812A/en not_active Expired
- 1966-02-03 GB GB4739/66A patent/GB1128178A/en not_active Expired
- 1966-02-03 NL NL6601397A patent/NL6601397A/xx unknown
- 1966-09-06 US US577172A patent/US3462417A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3462417A (en) | 1969-08-19 |
| DE1545697B2 (de) | 1973-03-29 |
| DE1545697A1 (de) | 1969-06-26 |
| GB1128178A (en) | 1968-09-25 |
| DE1545696B2 (de) | 1973-03-29 |
| US3431255A (en) | 1969-03-04 |
| JPS5233118B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-26 |
| NL6601397A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-08-04 |
| GB1088812A (en) | 1967-10-25 |
| DE1545653A1 (de) | 1969-08-07 |
| DE1545697C3 (de) | 1973-11-08 |
| DE1545696C3 (de) | 1973-11-08 |
| DE1545696A1 (de) | 1969-06-26 |
| CH462818A (de) | 1968-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH456605A (de) | Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flüssiger Phase | |
| EP0010666A1 (de) | Verfahren zur kontinuierlichen Herstellung von epsilon-Caprolactam durch Beckmann'sche Umlagerung | |
| DE1194863B (de) | Verfahren zur gleichzeitigen Gewinnung von reinem Ammoniumsulfat und reinen Lactamen aus Gemischen, die durch Beckmannsche Umlagerung von cycloaliphatischen Ketoximen mit Schwefelsaeure oder Oleum erhalten worden sind | |
| DE4205633A1 (de) | Verfahren zur reinigung von cyclohexanon | |
| DE69717976T2 (de) | Gewinnung von epsilon-caprolactam aus wässrigen gemischen | |
| DE2161215B2 (de) | Verfahren zur Herstellung von 5-Vmylnorbornen-(2) | |
| DE2163259A1 (de) | Verfahren zur Reinigung von Lactamen | |
| DE2148717A1 (de) | Verfahren zur Reinigung von Lactamen | |
| DE3635363A1 (de) | Verfahren zur neutralisation von reaktionsgemischen, die durch beckmann'sche umlagerung von cyclohexanonoxim erhalten worden sind | |
| DE1300567C2 (de) | Verfahren zur reinigung von unzersetzt schmelzenden kristallisierbaren organischen stoffen | |
| EP0628544B1 (de) | Herstellung von beta-Jonon | |
| DE2111196A1 (de) | Verfahren zur Gewinnung von Adipinsaeure | |
| DE1545653C (de) | Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flussi ger Phase | |
| DE1695253A1 (de) | Verfahren zur Herstellung von omega-Dodecalactam | |
| DE2708388A1 (de) | Verfahren zur herstellung von 4,4'- dihydroxydiphenylsulfon | |
| DE2547025A1 (de) | Verfahren zur herstellung von epsilon-caprolactam | |
| DE2651195C3 (de) | Verfahren zur Gewinnung von grobkristallinem reinem Ammonsulfat | |
| DE1303091C2 (de) | Verfahren zur herstellung von epsilon-caprolactam | |
| DE2338479A1 (de) | Verfahren zur aufarbeitung von nitrierungsprodukte enthaltender salpetersaeure | |
| DE1545653B (de) | Verfahren zur kontinuierlichen Herstellung von Laurinlactam in flüssiger Phase | |
| DE1298977B (de) | Verfahren zur Gewinnung von Adipinsaeure | |
| DE1695262A1 (de) | Verfahren zur kontinuierlichen Herstellung von Lactamen | |
| DE1205966B (de) | Verfahren zur Herstellung von in Wasser schwer-loeslichen oder unloeslichen Cycloalkanonoximen | |
| DE2218316A1 (de) | Verfahren zur herstellung von anthrachinon | |
| DE2331250C3 (de) | Verfahren zur Trennung von Resorcin und Hydrochinon |