DE1255110B - Verfahren zur Herstellung von Caprolactam - Google Patents
Verfahren zur Herstellung von CaprolactamInfo
- Publication number
- DE1255110B DE1255110B DEC25459A DEC0025459A DE1255110B DE 1255110 B DE1255110 B DE 1255110B DE C25459 A DEC25459 A DE C25459A DE C0025459 A DEC0025459 A DE C0025459A DE 1255110 B DE1255110 B DE 1255110B
- Authority
- DE
- Germany
- Prior art keywords
- caprolactam
- carbon tetrachloride
- acid
- production
- solvent
- 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 description 30
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 26
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkyl nitrites Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 229960003116 amyl nitrite Drugs 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SEOYNUHKXVGWFU-UHFFFAOYSA-N mu-oxidobis(oxidonitrogen) Chemical compound O=NON=O SEOYNUHKXVGWFU-UHFFFAOYSA-N 0.000 description 1
- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical compound OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005406 washing 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
- C07D201/10—Preparation of lactams from cycloaliphatic compounds by simultaneous nitrosylation and rearrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3843360A GB930006A (en) | 1960-11-09 | 1960-11-09 | Improvements relating to the manufacture of caprolactam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1255110B true DE1255110B (de) | 1967-11-30 |
Family
ID=10403398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC25459A Pending DE1255110B (de) | 1960-11-09 | 1961-11-08 | Verfahren zur Herstellung von Caprolactam |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE610129A (cs) |
| CH (1) | CH409970A (cs) |
| DE (1) | DE1255110B (cs) |
| ES (1) | ES271860A1 (cs) |
| GB (1) | GB930006A (cs) |
| NL (1) | NL271197A (cs) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1238981A (fr) * | 1958-09-18 | 1960-08-19 | Snia Viscosa | Procédé de préparation du caprolactame |
-
0
- NL NL271197D patent/NL271197A/xx unknown
-
1960
- 1960-11-09 GB GB3843360A patent/GB930006A/en not_active Expired
-
1961
- 1961-11-08 DE DEC25459A patent/DE1255110B/de active Pending
- 1961-11-08 CH CH1293561A patent/CH409970A/de unknown
- 1961-11-09 BE BE610129A patent/BE610129A/fr unknown
- 1961-11-09 ES ES0271860A patent/ES271860A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1238981A (fr) * | 1958-09-18 | 1960-08-19 | Snia Viscosa | Procédé de préparation du caprolactame |
Also Published As
| Publication number | Publication date |
|---|---|
| NL271197A (cs) | |
| ES271860A1 (es) | 1962-03-01 |
| GB930006A (en) | 1963-06-26 |
| CH409970A (de) | 1966-03-31 |
| BE610129A (fr) | 1962-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1255110B (de) | Verfahren zur Herstellung von Caprolactam | |
| DE2508247A1 (de) | Verfahren zur herstellung von cyclohexanonoxim | |
| DE68903213T2 (de) | Verfahren zur herstellung von nitrophenolen. | |
| DE1271711B (de) | Verfahren zur Herstellung von Cyclohexanonoxim | |
| DE2443341A1 (de) | Verfahren zur reinigung von caprolactam | |
| DE2410310A1 (de) | Verfahren zur herstellung von 1-aminoanthrachinon | |
| DE689191C (de) | Verfahren zur Herstellung von Aminoguanidinbicarbonat | |
| DE753046C (de) | Verfahren zur Umlagerung von Ketoximen | |
| DE972273C (de) | Verfahren zur Herstellung von Nitrierungsprodukten von Toluol | |
| DE877303C (de) | Verfahren zur Herstellung von Oximen | |
| AT229859B (de) | Verfahren zur Herstellung von Caprolactam | |
| DE630652C (de) | Verfahren zur Umsetzung von Alkalichloriden mit ueberschuessiger Salpetersaeure | |
| DE1166184B (de) | Verfahren zur gleichzeitigen Gewinnung von Methacrylsaeureamid und Ammoniumbisulfat | |
| DE636981C (de) | Verfahren zur Umsetzung von Alkalichloriden mit ueberschuessiger Salpetersaeure | |
| AT230865B (de) | Verfahren zur Herstellung von C-Alkyl-ɛ-caprolactamen | |
| DE671012C (de) | Verfahren zur Herstellung von Acetonperoxyd | |
| DE1024957B (de) | Verfahren zur Herstellung von ª‡, ª‰-Dichlor-ª‰-formylacrylsaeure (Mucochlorsaeure) | |
| DE939811C (de) | Verfahren zur Herstellung von ªÏ-Caprolactam und seinen Derivaten | |
| DE395490C (de) | Verfahren zur Herstellung von Alkalinitraten unter Benutzung von Alkalichloriden | |
| DE2126881A1 (de) | Verfahren zur Herstellung von Nitrilotriacetonitril | |
| AT239252B (de) | Verfahren zur partiellen oder vollständigen Carbamylierung von zweiwertigen Alkoholen oder von deren partiell O-substituierten Derivaten | |
| GB1126054A (en) | Improvements in or relating to the preparation of acrylamide | |
| DE1081018B (de) | Verfahren zur Herstellung von 2-Thiol-glucimidazolderivaten | |
| DE1205063B (de) | Verfahren zur Herstellung von Nitrosylschwefel-saeure | |
| DE1620476B2 (de) | Verfahren zur Herstellung von 3-Nitro-azacycloheptanon(2)-l-carbonsäure Chlorid |