DE2107078C3 - Verfahren zur Herstellung von N-Formyl-Acetyl-oder Propionylcaprolactam - Google Patents
Verfahren zur Herstellung von N-Formyl-Acetyl-oder PropionylcaprolactamInfo
- Publication number
- DE2107078C3 DE2107078C3 DE19712107078 DE2107078A DE2107078C3 DE 2107078 C3 DE2107078 C3 DE 2107078C3 DE 19712107078 DE19712107078 DE 19712107078 DE 2107078 A DE2107078 A DE 2107078A DE 2107078 C3 DE2107078 C3 DE 2107078C3
- Authority
- DE
- Germany
- Prior art keywords
- oxime
- catalyst
- caprolactam
- yield
- reaction
- 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
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title description 26
- -1 propionyl caprolactam Chemical compound 0.000 title description 7
- 150000002923 oximes Chemical class 0.000 claims description 18
- WVHFJGDRUXQYGR-UHFFFAOYSA-N 3-propanoylazepan-2-one Chemical compound CCC(=O)C1CCCCNC1=O WVHFJGDRUXQYGR-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 48
- 239000003054 catalyst Substances 0.000 description 42
- ZXDUJBCPCXIAKU-UHFFFAOYSA-N 1-(2-hydroxyiminocyclohexyl)ethanone Chemical compound CC(=O)C1CCCCC1=NO ZXDUJBCPCXIAKU-UHFFFAOYSA-N 0.000 description 18
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 16
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 8
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 7
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QYFCFXUKOAMMQX-UHFFFAOYSA-N 1-(2-hydroxyiminocyclohexyl)propan-1-one Chemical compound C(CC)(=O)C1C(CCCC1)=NO QYFCFXUKOAMMQX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VGTSJKBOTYPCLW-UHFFFAOYSA-N 1-propanoylazepan-2-one Chemical compound CCC(=O)N1CCCCCC1=O VGTSJKBOTYPCLW-UHFFFAOYSA-N 0.000 description 2
- JXBZNUBZEPHBIC-UHFFFAOYSA-N 2-oxoazepane-1-carbaldehyde Chemical compound O=CN1CCCCCC1=O JXBZNUBZEPHBIC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011491 glass wool Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- WHXCGIRATPOBAY-VOTSOKGWSA-N (ne)-n-hexan-2-ylidenehydroxylamine Chemical compound CCCC\C(C)=N\O WHXCGIRATPOBAY-VOTSOKGWSA-N 0.000 description 1
- 241001214176 Capros Species 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010457 zeolite Substances 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1325970 | 1970-02-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2107078A1 DE2107078A1 (de) | 1971-09-02 |
| DE2107078B2 DE2107078B2 (de) | 1973-07-05 |
| DE2107078C3 true DE2107078C3 (de) | 1974-02-28 |
Family
ID=11828208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712107078 Expired DE2107078C3 (de) | 1970-02-16 | 1971-02-15 | Verfahren zur Herstellung von N-Formyl-Acetyl-oder Propionylcaprolactam |
Country Status (5)
| Country | Link |
|---|---|
| CA (1) | CA924317A (enExample) |
| DE (1) | DE2107078C3 (enExample) |
| FR (1) | FR2080999B1 (enExample) |
| GB (1) | GB1314778A (enExample) |
| NL (1) | NL7102046A (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB844267A (en) * | 1956-10-30 | 1960-08-10 | Merck & Co Inc | N-acyl-3-chlorocaprolactams and their conversion to 6-acylamino-2-chloro-hexanoic acids |
| GB881927A (en) * | 1959-06-16 | 1961-11-08 | British Petroleum Co | Improvements in or relating to the production of amides and lactams |
-
1971
- 1971-02-11 CA CA105300A patent/CA924317A/en not_active Expired
- 1971-02-15 DE DE19712107078 patent/DE2107078C3/de not_active Expired
- 1971-02-15 FR FR7105008A patent/FR2080999B1/fr not_active Expired
- 1971-02-16 NL NL7102046A patent/NL7102046A/xx not_active Application Discontinuation
- 1971-04-19 GB GB2186271A patent/GB1314778A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2107078B2 (de) | 1973-07-05 |
| NL7102046A (enExample) | 1971-08-18 |
| GB1314778A (en) | 1973-04-26 |
| FR2080999A1 (enExample) | 1971-11-26 |
| DE2107078A1 (de) | 1971-09-02 |
| FR2080999B1 (enExample) | 1974-02-15 |
| CA924317A (en) | 1973-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |