DE2223643C3 - Verfahren zu der Umlagerung alicyclischer Ketoxime in die entsprechenden Lactame - Google Patents
Verfahren zu der Umlagerung alicyclischer Ketoxime in die entsprechenden LactameInfo
- Publication number
- DE2223643C3 DE2223643C3 DE19722223643 DE2223643A DE2223643C3 DE 2223643 C3 DE2223643 C3 DE 2223643C3 DE 19722223643 DE19722223643 DE 19722223643 DE 2223643 A DE2223643 A DE 2223643A DE 2223643 C3 DE2223643 C3 DE 2223643C3
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- lactam
- rearrangement
- solvent
- ion exchanger
- 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
- 150000003951 lactams Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 15
- 230000008707 rearrangement Effects 0.000 title claims description 13
- 125000002723 alicyclic group Chemical group 0.000 title claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 34
- 150000002923 oximes Chemical class 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 230000002378 acidificating effect Effects 0.000 claims description 24
- 239000011949 solid catalyst Substances 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 16
- 150000001768 cations Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000001166 ammonium sulphate Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052810 boron oxide Inorganic materials 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- SCRFXJBEIINMIC-UHFFFAOYSA-N n-cyclododecylidenehydroxylamine Chemical compound ON=C1CCCCCCCCCCC1 SCRFXJBEIINMIC-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 Amberlyst 15 ion Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation 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
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- MOWNZPNSYMGTMD-UHFFFAOYSA-N oxidoboron Chemical class O=[B] MOWNZPNSYMGTMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
-
- H—ELECTRICITY
- H03—ELECTRONIC CIRCUITRY
- H03K—PULSE TECHNIQUE
- H03K17/00—Electronic switching or gating, i.e. not by contact-making and –breaking
- H03K17/94—Electronic switching or gating, i.e. not by contact-making and –breaking characterised by the way in which the control signals are generated
- H03K17/945—Proximity switches
- H03K17/95—Proximity switches using a magnetic detector
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7106705A NL162374C (nl) | 1971-05-15 | 1971-05-15 | Werkwijze voor de omlegging van alicyclische ketoximen in de overeenkomstige lactamen. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2223643A1 DE2223643A1 (de) | 1972-11-30 |
| DE2223643B2 DE2223643B2 (de) | 1980-09-25 |
| DE2223643C3 true DE2223643C3 (de) | 1981-08-20 |
Family
ID=19813175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722223643 Expired DE2223643C3 (de) | 1971-05-15 | 1972-05-15 | Verfahren zu der Umlagerung alicyclischer Ketoxime in die entsprechenden Lactame |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5139233B1 (OSRAM) |
| BE (1) | BE783491A (OSRAM) |
| CH (1) | CH572033A5 (OSRAM) |
| DE (1) | DE2223643C3 (OSRAM) |
| FR (1) | FR2137887B1 (OSRAM) |
| GB (1) | GB1342550A (OSRAM) |
| IT (1) | IT957844B (OSRAM) |
| NL (1) | NL162374C (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0461779B1 (en) * | 1990-06-15 | 1995-08-16 | Yusuke Izumi | Reaction accelerator for rearrangement of oxime to amide and process for producing amides by rearrangement of oximes |
| NL9201160A (nl) * | 1992-06-30 | 1994-01-17 | Dsm Nv | Werkwijze voor de omzetting van oximen in de overeenkomstige amides. |
| BE1007409A3 (nl) * | 1993-08-20 | 1995-06-06 | Dsm Nv | Werkwijze voor het bereiden van een lactam. |
-
1971
- 1971-05-15 NL NL7106705A patent/NL162374C/xx not_active IP Right Cessation
-
1972
- 1972-05-12 GB GB2243072A patent/GB1342550A/en not_active Expired
- 1972-05-13 IT IT5023472A patent/IT957844B/it active
- 1972-05-15 JP JP47048013A patent/JPS5139233B1/ja active Pending
- 1972-05-15 BE BE783491A patent/BE783491A/xx unknown
- 1972-05-15 DE DE19722223643 patent/DE2223643C3/de not_active Expired
- 1972-05-15 FR FR7217243A patent/FR2137887B1/fr not_active Expired
- 1972-05-15 CH CH719572A patent/CH572033A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1342550A (en) | 1974-01-03 |
| CH572033A5 (OSRAM) | 1976-01-30 |
| BE783491A (fr) | 1972-11-16 |
| NL162374B (nl) | 1979-12-17 |
| NL162374C (nl) | 1980-05-16 |
| JPS5139233B1 (OSRAM) | 1976-10-26 |
| NL7106705A (OSRAM) | 1972-11-17 |
| FR2137887A1 (OSRAM) | 1972-12-29 |
| DE2223643B2 (de) | 1980-09-25 |
| IT957844B (it) | 1973-10-20 |
| DE2223643A1 (de) | 1972-11-30 |
| FR2137887B1 (OSRAM) | 1979-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |