CN1130181A - 生产酰胺及己内酰胺的方法 - Google Patents
生产酰胺及己内酰胺的方法 Download PDFInfo
- Publication number
- CN1130181A CN1130181A CN 95117244 CN95117244A CN1130181A CN 1130181 A CN1130181 A CN 1130181A CN 95117244 CN95117244 CN 95117244 CN 95117244 A CN95117244 A CN 95117244A CN 1130181 A CN1130181 A CN 1130181A
- Authority
- CN
- China
- Prior art keywords
- carboxylic acid
- oxime
- acid
- hexanolactam
- rearrangement
- 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.)
- Pending
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- -1 amide acetate Chemical class 0.000 title description 3
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical group ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 34
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 10
- 238000010930 lactamization Methods 0.000 claims description 9
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 9
- 230000008707 rearrangement Effects 0.000 claims description 9
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 19
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract description 10
- 235000011130 ammonium sulphate Nutrition 0.000 abstract description 10
- 239000012530 fluid Substances 0.000 abstract description 2
- 230000017105 transposition Effects 0.000 abstract 2
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000012423 maintenance Methods 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 27
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001959A/94 | 1994-09-27 | ||
| ITMI941959A IT1270090B (it) | 1994-09-27 | 1994-09-27 | Procedimento per l'uso di acidi carbossilici nella trasportazione di beckmann con oleum delle chetossime ad ammidi e per la produzione di caprolattame per trasposizione della cicloesanonossima in presenza di acido cicloesilcarbossilico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1130181A true CN1130181A (zh) | 1996-09-04 |
Family
ID=11369602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 95117244 Pending CN1130181A (zh) | 1994-09-27 | 1995-09-26 | 生产酰胺及己内酰胺的方法 |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN1130181A (ru) |
| IT (1) | IT1270090B (ru) |
| RU (1) | RU2125556C1 (ru) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101168524B (zh) * | 2007-11-01 | 2010-05-26 | 湘潭大学 | 一种低磺化的己内酰胺制备方法 |
| WO2024000848A1 (zh) * | 2022-06-29 | 2024-01-04 | 中国天辰工程有限公司 | 一种不副产硫酸铵的己内酰胺合成方法 |
-
1994
- 1994-09-27 IT ITMI941959A patent/IT1270090B/it active IP Right Grant
-
1995
- 1995-09-26 RU RU95116368A patent/RU2125556C1/ru active
- 1995-09-26 CN CN 95117244 patent/CN1130181A/zh active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101168524B (zh) * | 2007-11-01 | 2010-05-26 | 湘潭大学 | 一种低磺化的己内酰胺制备方法 |
| WO2024000848A1 (zh) * | 2022-06-29 | 2024-01-04 | 中国天辰工程有限公司 | 一种不副产硫酸铵的己内酰胺合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI941959A1 (it) | 1996-03-27 |
| RU2125556C1 (ru) | 1999-01-27 |
| ITMI941959A0 (it) | 1994-09-27 |
| IT1270090B (it) | 1997-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |