CN1036583C - 肟转化成相应酰胺的方法 - Google Patents
肟转化成相应酰胺的方法 Download PDFInfo
- Publication number
- CN1036583C CN1036583C CN93107880A CN93107880A CN1036583C CN 1036583 C CN1036583 C CN 1036583C CN 93107880 A CN93107880 A CN 93107880A CN 93107880 A CN93107880 A CN 93107880A CN 1036583 C CN1036583 C CN 1036583C
- Authority
- CN
- China
- Prior art keywords
- group
- oxime
- phenyl ring
- organic
- alkyl
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 7
- 150000002923 oximes Chemical class 0.000 title abstract description 16
- 150000001408 amides Chemical class 0.000 title abstract description 4
- 230000008569 process Effects 0.000 title abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 238000006277 sulfonation reaction Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 2
- 239000003456 ion exchange resin Substances 0.000 claims 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims 2
- 239000003054 catalyst Substances 0.000 abstract description 14
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 4
- 239000002638 heterogeneous catalyst Substances 0.000 abstract description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 butene-1-ketoxime Chemical compound 0.000 description 6
- 229910052799 carbon Inorganic materials 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
- 229920001429 chelating resin Polymers 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- KTPUHSVFNHULJH-UHFFFAOYSA-N n-cyclooctylidenehydroxylamine Chemical compound ON=C1CCCCCCC1 KTPUHSVFNHULJH-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 1
- WHXCGIRATPOBAY-VOTSOKGWSA-N (ne)-n-hexan-2-ylidenehydroxylamine Chemical compound CCCC\C(C)=N\O WHXCGIRATPOBAY-VOTSOKGWSA-N 0.000 description 1
- IFDZZSXEPSSHNC-ONEGZZNKSA-N (ne)-n-propylidenehydroxylamine Chemical compound CC\C=N\O IFDZZSXEPSSHNC-ONEGZZNKSA-N 0.000 description 1
- HQSMEHLVLOGBCK-UHFFFAOYSA-N 1-ethenylsulfinylethene Chemical compound C=CS(=O)C=C HQSMEHLVLOGBCK-UHFFFAOYSA-N 0.000 description 1
- DMJZWFZICOEEAJ-UHFFFAOYSA-N 2-(4-bromothiophen-3-yl)sulfanylpropanoic acid Chemical compound OC(=O)C(C)SC1=CSC=C1Br DMJZWFZICOEEAJ-UHFFFAOYSA-N 0.000 description 1
- ZNNSPZOSKINXHF-UHFFFAOYSA-N 5-sulfinylcyclohexa-1,3-diene Chemical compound O=S=C1CC=CC=C1 ZNNSPZOSKINXHF-UHFFFAOYSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 150000001941 cyclopentenes Chemical class 0.000 description 1
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BNVLIKHTHIFMNV-UHFFFAOYSA-N n-cyclopropylidenehydroxylamine Chemical compound ON=C1CC1 BNVLIKHTHIFMNV-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000001291 vacuum drying 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/13—Nucleic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/606—Nucleosides; Nucleotides; Nucleic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Mycology (AREA)
- Dermatology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Testing Of Coins (AREA)
- Purification Treatments By Anaerobic Or Anaerobic And Aerobic Bacteria Or Animals (AREA)
- Saccharide Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL9201160A NL9201160A (nl) | 1992-06-30 | 1992-06-30 | Werkwijze voor de omzetting van oximen in de overeenkomstige amides. |
| NL9201160 | 1992-06-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1083807A CN1083807A (zh) | 1994-03-16 |
| CN1036583C true CN1036583C (zh) | 1997-12-03 |
Family
ID=19860992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93107880A Expired - Fee Related CN1036583C (zh) | 1992-06-30 | 1993-06-29 | 肟转化成相应酰胺的方法 |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0577203B1 (enExample) |
| JP (1) | JPH07300454A (enExample) |
| KR (1) | KR100291352B1 (enExample) |
| CN (1) | CN1036583C (enExample) |
| AT (1) | ATE148097T1 (enExample) |
| BR (1) | BR9302701A (enExample) |
| CZ (1) | CZ287271B6 (enExample) |
| DE (1) | DE69307608T2 (enExample) |
| DK (1) | DK0577203T3 (enExample) |
| ES (1) | ES2097968T3 (enExample) |
| GE (1) | GEP19971109B (enExample) |
| GR (1) | GR3023169T3 (enExample) |
| HU (1) | HU213633B (enExample) |
| MX (1) | MX9303897A (enExample) |
| NL (1) | NL9201160A (enExample) |
| PL (1) | PL173841B1 (enExample) |
| RU (1) | RU2101278C1 (enExample) |
| SG (1) | SG48178A1 (enExample) |
| TW (1) | TW223055B (enExample) |
| UA (1) | UA43307C2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1095461C (zh) * | 1999-04-30 | 2002-12-04 | 中国科学院上海有机化学研究所 | 三氟乙酰基苯乙酮肟及其衍生物的合成方法 |
| FR2803197B1 (fr) * | 1999-12-30 | 2002-03-15 | Oreal | Composition pour la teinture d'oxydation des fibres keratiniques comprenant un polymere epaississant comportant au moins une chaine grasse et un alcool gras ayant plus de vingt atomes de carbone |
| CN100389107C (zh) * | 2003-06-30 | 2008-05-21 | 中国石油化工股份有限公司 | 一种制备己内酰胺的方法 |
| CN1312133C (zh) * | 2004-03-15 | 2007-04-25 | 中国石油化工股份有限公司 | 一种从离子液体中分离贝克曼重排反应产物的方法 |
| CN101250148B (zh) * | 2008-03-14 | 2010-08-25 | 湘潭大学 | 一种环己酮肟液相重排制取己内酰胺的方法 |
| CN102863385B (zh) * | 2012-10-09 | 2014-01-01 | 清华大学 | 一种由环己酮直接合成己内酰胺的方法 |
| CN108080027B (zh) * | 2017-12-23 | 2021-05-28 | 中国天辰工程有限公司 | 一种液相贝克曼重排制己内酰胺的树脂催化剂处理工艺 |
| CN119192453B (zh) * | 2024-08-28 | 2025-11-18 | 华东理工大学 | 具有纳米球结构的树脂型催化剂及其制备方法和应用、己内酰胺的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1029201A (en) * | 1962-01-13 | 1966-05-11 | Inventa Ag | Process for the rearrangement of cyclic oximes |
| US3944542A (en) * | 1971-05-15 | 1976-03-16 | Stamicarbon, B.V. | Conversion of ketoximes into lactams in organic sulfoxide solvents |
| CN1058588A (zh) * | 1990-07-06 | 1992-02-12 | Dsm有限公司 | 处理酰胺的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL162374C (nl) * | 1971-05-15 | 1980-05-16 | Stamicarbon | Werkwijze voor de omlegging van alicyclische ketoximen in de overeenkomstige lactamen. |
-
1992
- 1992-06-30 NL NL9201160A patent/NL9201160A/nl not_active Application Discontinuation
-
1993
- 1993-06-08 TW TW082104548A patent/TW223055B/zh active
- 1993-06-11 UA UA93002178A patent/UA43307C2/uk unknown
- 1993-06-21 GE GEAP1993912A patent/GEP19971109B/en unknown
- 1993-06-23 KR KR1019930011444A patent/KR100291352B1/ko not_active Expired - Fee Related
- 1993-06-25 DK DK93201841.9T patent/DK0577203T3/da active
- 1993-06-25 SG SG1996007654A patent/SG48178A1/en unknown
- 1993-06-25 DE DE69307608T patent/DE69307608T2/de not_active Expired - Fee Related
- 1993-06-25 ES ES93201841T patent/ES2097968T3/es not_active Expired - Lifetime
- 1993-06-25 AT AT93201841T patent/ATE148097T1/de not_active IP Right Cessation
- 1993-06-25 EP EP93201841A patent/EP0577203B1/en not_active Expired - Lifetime
- 1993-06-28 JP JP5156825A patent/JPH07300454A/ja active Pending
- 1993-06-28 CZ CZ19931290A patent/CZ287271B6/cs not_active IP Right Cessation
- 1993-06-29 CN CN93107880A patent/CN1036583C/zh not_active Expired - Fee Related
- 1993-06-29 BR BR9302701A patent/BR9302701A/pt not_active IP Right Cessation
- 1993-06-29 RU RU93034459A patent/RU2101278C1/ru active
- 1993-06-29 PL PL93299511A patent/PL173841B1/pl unknown
- 1993-06-29 MX MX9303897A patent/MX9303897A/es not_active IP Right Cessation
- 1993-06-29 HU HU9301895A patent/HU213633B/hu not_active IP Right Cessation
-
1997
- 1997-04-18 GR GR970400826T patent/GR3023169T3/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1029201A (en) * | 1962-01-13 | 1966-05-11 | Inventa Ag | Process for the rearrangement of cyclic oximes |
| US3944542A (en) * | 1971-05-15 | 1976-03-16 | Stamicarbon, B.V. | Conversion of ketoximes into lactams in organic sulfoxide solvents |
| CN1058588A (zh) * | 1990-07-06 | 1992-02-12 | Dsm有限公司 | 处理酰胺的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ129093A3 (en) | 1994-01-19 |
| BR9302701A (pt) | 1994-02-08 |
| HUT65116A (en) | 1994-04-28 |
| EP0577203B1 (en) | 1997-01-22 |
| DK0577203T3 (da) | 1997-07-14 |
| PL173841B1 (pl) | 1998-05-29 |
| HU213633B (en) | 1997-08-28 |
| EP0577203A1 (en) | 1994-01-05 |
| KR100291352B1 (ko) | 2001-09-17 |
| KR940000411A (ko) | 1994-01-03 |
| TW223055B (enExample) | 1994-05-01 |
| NL9201160A (nl) | 1994-01-17 |
| PL299511A1 (en) | 1994-01-10 |
| MX9303897A (es) | 1993-12-01 |
| RU2101278C1 (ru) | 1998-01-10 |
| CN1083807A (zh) | 1994-03-16 |
| DE69307608T2 (de) | 1997-09-04 |
| GEP19971109B (en) | 1997-10-10 |
| GR3023169T3 (en) | 1997-07-30 |
| DE69307608D1 (de) | 1997-03-06 |
| ES2097968T3 (es) | 1997-04-16 |
| CZ287271B6 (en) | 2000-10-11 |
| HU9301895D0 (en) | 1993-09-28 |
| JPH07300454A (ja) | 1995-11-14 |
| SG48178A1 (en) | 1998-04-17 |
| UA43307C2 (uk) | 2001-12-17 |
| ATE148097T1 (de) | 1997-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1036583C (zh) | 肟转化成相应酰胺的方法 | |
| CN1176906C (zh) | N-甲基吡咯烷酮的制备方法 | |
| CN1762985A (zh) | 一种非均相肟化重排制备酰胺的方法 | |
| CN1171772A (zh) | 5－氯－2,3－二氢－1h－茚－1－酮的制备方法 | |
| US4094907A (en) | Process for the preparation of polyamines | |
| US3393220A (en) | Process for the preparation of high purity phthalonitriles | |
| US3944542A (en) | Conversion of ketoximes into lactams in organic sulfoxide solvents | |
| CN116120189B (zh) | 一种含仲氨基和伯氨基的液态芳香族胺类固化剂的制备方法 | |
| CN1166378A (zh) | 氨氧化法制2，6-二氯苯腈的新型催化剂 | |
| CN1781908A (zh) | 催化环己酮肟重排制备ε－己内酰胺的方法 | |
| US5571913A (en) | Process for preparing a lactam | |
| CN1287110A (zh) | 用添加剂制备氧代异佛尔酮的方法 | |
| CN114507169B (zh) | O-烷基己内酰亚胺转化成己内酰胺的方法及其应用 | |
| CN116832860B (zh) | 一种高分子担载nhpi和磺酸基双功能催化剂的制备方法及其应用 | |
| CN115872824B (zh) | 一种对叔丁基乙苯的制备方法 | |
| EP3083558A2 (en) | Process for the production of phthalimides | |
| KR920009789B1 (ko) | 에틸비페닐류의 제조방법 | |
| CN1188109A (zh) | 含硫巯基羧酸及其酯的生产方法 | |
| CN87105264A (zh) | 氢过氧化物混合物的处理 | |
| KR100960050B1 (ko) | 이온교환된 제올라이트 촉매를 이용한1,5-디메틸테트랄린의 제조방법 | |
| CN120987878A (zh) | 一种甲基丙烯酸缩水甘油酯及其制备方法 | |
| GB2077723A (en) | Process for the production of acrylamide | |
| CN102464628B (zh) | 一种环状α,β-不饱和磺酰胺衍生物的制备方法 | |
| WO2023003058A1 (ko) | 프탈로니트릴계 화합물의 제조방법 | |
| CN114436847A (zh) | 2,5-二甲氧基-β-硝基苯乙烯的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |