CN1762985A - 一种非均相肟化重排制备酰胺的方法 - Google Patents
一种非均相肟化重排制备酰胺的方法 Download PDFInfo
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- CN1762985A CN1762985A CN 200510032184 CN200510032184A CN1762985A CN 1762985 A CN1762985 A CN 1762985A CN 200510032184 CN200510032184 CN 200510032184 CN 200510032184 A CN200510032184 A CN 200510032184A CN 1762985 A CN1762985 A CN 1762985A
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- 238000000034 method Methods 0.000 title claims abstract description 62
- 238000006146 oximation reaction Methods 0.000 title claims abstract description 36
- 230000008707 rearrangement Effects 0.000 title claims abstract description 31
- 150000001408 amides Chemical class 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 37
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000012442 inert solvent Substances 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 24
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims abstract description 10
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 48
- 239000012071 phase Substances 0.000 claims description 39
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 25
- 238000000605 extraction Methods 0.000 claims description 18
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 14
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000006462 rearrangement reaction Methods 0.000 claims description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 5
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000008365 aromatic ketones Chemical class 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- HIGZEFHDFAMPND-UHFFFAOYSA-N azepan-2-one;sulfuric acid Chemical group OS(O)(=O)=O.O=C1CCCCCN1 HIGZEFHDFAMPND-UHFFFAOYSA-N 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 238000007210 heterogeneous catalysis Methods 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 26
- 239000000047 product Substances 0.000 abstract description 14
- 239000006227 byproduct Substances 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000007062 hydrolysis Effects 0.000 abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- LPBIYXNPXGJEFN-UHFFFAOYSA-N n-(dicyclohexylmethylidene)hydroxylamine Chemical compound C1CCCCC1C(=NO)C1CCCCC1 LPBIYXNPXGJEFN-UHFFFAOYSA-N 0.000 abstract 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005516 engineering process Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 150000002923 oximes Chemical class 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- -1 ammonium carboxylate salt Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000002309 gasification Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 2
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
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- 230000007423 decrease Effects 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
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- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000007034 nitrosation reaction Methods 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical class ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Description
Claims (14)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2005100321840A CN100386307C (zh) | 2005-09-23 | 2005-09-23 | 一种非均相肟化重排制备酰胺的方法 |
PCT/CN2006/002434 WO2007033582A1 (fr) | 2005-09-23 | 2006-09-18 | Procede de preparation d'amides par oxymation heterogene et reagencement |
JP2008531513A JP5249033B2 (ja) | 2005-09-23 | 2006-09-18 | 不均一系オキシム化および転位によるアミドを生産する方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2005100321840A CN100386307C (zh) | 2005-09-23 | 2005-09-23 | 一种非均相肟化重排制备酰胺的方法 |
Publications (2)
Publication Number | Publication Date |
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CN1762985A true CN1762985A (zh) | 2006-04-26 |
CN100386307C CN100386307C (zh) | 2008-05-07 |
Family
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CNB2005100321840A Active CN100386307C (zh) | 2005-09-23 | 2005-09-23 | 一种非均相肟化重排制备酰胺的方法 |
Country Status (3)
Country | Link |
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JP (1) | JP5249033B2 (zh) |
CN (1) | CN100386307C (zh) |
WO (1) | WO2007033582A1 (zh) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101891681A (zh) * | 2010-07-09 | 2010-11-24 | 清华大学 | 一种由环己酮肟制备己内酰胺的贝克曼重排新方法 |
CN103384660A (zh) * | 2011-12-20 | 2013-11-06 | 住友化学株式会社 | 高品质ε-己内酰胺的制造方法 |
CN104910071A (zh) * | 2015-05-08 | 2015-09-16 | 河北美邦工程科技股份有限公司 | 一种制备己内酰胺的方法 |
CN105315211A (zh) * | 2014-08-01 | 2016-02-10 | 中国石油化工股份有限公司 | 高浓度发烟硫酸催化环己酮肟制备己内酰胺的方法 |
CN105837507A (zh) * | 2015-01-15 | 2016-08-10 | 湖北金湘宁化工科技有限公司 | 一种己内酰胺的制备方法 |
CN110809571A (zh) * | 2017-07-07 | 2020-02-18 | 维生源知识产权有限责任公司 | 一种长链氨基酸和二元酸的生产工艺 |
CN112479925A (zh) * | 2020-11-30 | 2021-03-12 | 中国天辰工程有限公司 | 一种大环烷酮氨肟化的方法 |
CN114671808A (zh) * | 2022-04-28 | 2022-06-28 | 武亚梅 | 一种己内酰胺的制备方法 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106831486B (zh) | 2017-03-03 | 2019-03-29 | 山东省化工研究院 | 一种合成酮肟的工艺方法 |
CN111751471A (zh) * | 2020-07-09 | 2020-10-09 | 山东方明化工股份有限公司 | 一种己内酰胺贝克曼重排液中杂质含量的检测方法 |
CN114471699B (zh) * | 2020-10-28 | 2023-09-19 | 万华化学集团股份有限公司 | 一种用于环十二酮氨肟化反应的催化剂组合物及其应用 |
CN114436889A (zh) | 2020-11-02 | 2022-05-06 | 湖北金湘宁化工科技有限公司 | 一种氨肟化反应与分离集成的方法及其装置 |
CN115215307B (zh) * | 2021-04-15 | 2024-03-29 | 华东师范大学 | 一种羟胺溶液的合成方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2845019A1 (de) * | 1978-10-16 | 1980-04-30 | Basf Ag | Verfahren zur kontinuierlichen herstellung von epsilon -caprolactam durch beckmann'sche umlagerung |
DE3538859A1 (de) * | 1985-11-02 | 1987-05-07 | Huels Chemische Werke Ag | Verfahren zum herstellen von lactamen mit 8 bis 15 kohlenstoffatomen aus den entsprechenden oximen |
IT1244680B (it) * | 1991-01-23 | 1994-08-08 | Montedipe Srl | Processo a piu' stadi per l'ammossimazione in fase liquida dei composti carbonilici |
DE10158352A1 (de) * | 2001-11-28 | 2003-06-12 | Degussa | Zweiphasige Ammoximierung |
CN1234683C (zh) * | 2002-01-10 | 2006-01-04 | 中国石油化工股份有限公司 | 一种环己酮氨肟化方法 |
CN1242988C (zh) * | 2002-12-13 | 2006-02-22 | 中国石油化工股份有限公司 | 一种己内酰胺的制备方法 |
-
2005
- 2005-09-23 CN CNB2005100321840A patent/CN100386307C/zh active Active
-
2006
- 2006-09-18 WO PCT/CN2006/002434 patent/WO2007033582A1/zh active Application Filing
- 2006-09-18 JP JP2008531513A patent/JP5249033B2/ja active Active
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101891681A (zh) * | 2010-07-09 | 2010-11-24 | 清华大学 | 一种由环己酮肟制备己内酰胺的贝克曼重排新方法 |
CN103384660A (zh) * | 2011-12-20 | 2013-11-06 | 住友化学株式会社 | 高品质ε-己内酰胺的制造方法 |
CN103384660B (zh) * | 2011-12-20 | 2015-11-25 | 住友化学株式会社 | 高品质ε-己内酰胺的制造方法 |
CN105315211A (zh) * | 2014-08-01 | 2016-02-10 | 中国石油化工股份有限公司 | 高浓度发烟硫酸催化环己酮肟制备己内酰胺的方法 |
CN105315211B (zh) * | 2014-08-01 | 2018-01-09 | 中国石油化工股份有限公司 | 高浓度发烟硫酸催化环己酮肟制备己内酰胺的方法 |
CN105837507A (zh) * | 2015-01-15 | 2016-08-10 | 湖北金湘宁化工科技有限公司 | 一种己内酰胺的制备方法 |
CN104910071A (zh) * | 2015-05-08 | 2015-09-16 | 河北美邦工程科技股份有限公司 | 一种制备己内酰胺的方法 |
CN110809571A (zh) * | 2017-07-07 | 2020-02-18 | 维生源知识产权有限责任公司 | 一种长链氨基酸和二元酸的生产工艺 |
CN110809571B (zh) * | 2017-07-07 | 2022-11-18 | 维生源知识产权有限责任公司 | 一种长链氨基酸和二元酸的生产工艺 |
CN112479925A (zh) * | 2020-11-30 | 2021-03-12 | 中国天辰工程有限公司 | 一种大环烷酮氨肟化的方法 |
CN112479925B (zh) * | 2020-11-30 | 2023-01-20 | 中国天辰工程有限公司 | 一种大环烷酮氨肟化的方法 |
CN114671808A (zh) * | 2022-04-28 | 2022-06-28 | 武亚梅 | 一种己内酰胺的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP5249033B2 (ja) | 2013-07-31 |
CN100386307C (zh) | 2008-05-07 |
WO2007033582A1 (fr) | 2007-03-29 |
JP2009508884A (ja) | 2009-03-05 |
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