DE2803657A1 - Verfahren zur gewinnung von epsilon- caprolactam aus einem epsilon-caprolactam- schwefelsaeure-reaktionsgemisch - Google Patents
Verfahren zur gewinnung von epsilon- caprolactam aus einem epsilon-caprolactam- schwefelsaeure-reaktionsgemischInfo
- Publication number
- DE2803657A1 DE2803657A1 DE19782803657 DE2803657A DE2803657A1 DE 2803657 A1 DE2803657 A1 DE 2803657A1 DE 19782803657 DE19782803657 DE 19782803657 DE 2803657 A DE2803657 A DE 2803657A DE 2803657 A1 DE2803657 A1 DE 2803657A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfuric acid
- lactam
- caprolactam
- ammonium
- line
- 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.)
- Withdrawn
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 69
- 239000011541 reaction mixture Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 48
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
- 239000007789 gas Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- 150000003951 lactams Chemical class 0.000 claims description 22
- 238000006386 neutralization reaction Methods 0.000 claims description 22
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 4
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 18
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 18
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 18
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 17
- 235000011130 ammonium sulphate Nutrition 0.000 description 17
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 230000008707 rearrangement Effects 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical group [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000001166 ammonium sulphate Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- -1 1-2-dichloroethane Chemical compound 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- HIGZEFHDFAMPND-UHFFFAOYSA-N azepan-2-one;sulfuric acid Chemical compound OS(O)(=O)=O.O=C1CCCCCN1 HIGZEFHDFAMPND-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 2
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Inorganic materials S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- LSQBSJGVGHPYAZ-UHFFFAOYSA-N triazanium;hydrogen sulfate;sulfate Chemical compound [NH4+].[NH4+].[NH4+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O LSQBSJGVGHPYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide 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
- C07D201/16—Separation or purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treating Waste Gases (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7700882A NL7700882A (nl) | 1977-01-28 | 1977-01-28 | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuurreac- tiemengsel. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2803657A1 true DE2803657A1 (de) | 1978-08-03 |
Family
ID=19827871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782803657 Withdrawn DE2803657A1 (de) | 1977-01-28 | 1978-01-27 | Verfahren zur gewinnung von epsilon- caprolactam aus einem epsilon-caprolactam- schwefelsaeure-reaktionsgemisch |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4133810A (en, 2012) |
| JP (1) | JPS5395990A (en, 2012) |
| AR (1) | AR217673A1 (en, 2012) |
| BE (1) | BE863012A (en, 2012) |
| BR (1) | BR7800529A (en, 2012) |
| CA (1) | CA1100961A (en, 2012) |
| CH (1) | CH632250A5 (en, 2012) |
| DE (1) | DE2803657A1 (en, 2012) |
| ES (1) | ES466424A1 (en, 2012) |
| FR (1) | FR2378769A1 (en, 2012) |
| GB (1) | GB1553358A (en, 2012) |
| IT (1) | IT1104146B (en, 2012) |
| MX (1) | MX5326E (en, 2012) |
| NL (1) | NL7700882A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010666A1 (de) * | 1978-10-16 | 1980-05-14 | BASF Aktiengesellschaft | Verfahren zur kontinuierlichen Herstellung von epsilon-Caprolactam durch Beckmann'sche Umlagerung |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7022844B2 (en) | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852272A (en) * | 1971-05-07 | 1974-12-03 | Stamicarbon | Process for removing lactams |
| US3879380A (en) * | 1971-12-11 | 1975-04-22 | Stamicarbon | Process for recovery of lactam |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2993889A (en) * | 1961-07-25 | Separation of a lactam from an acid | ||
| NL144600B (nl) * | 1964-03-07 | 1975-01-15 | Stamicarbon | Afscheiding van lactamen uit een sterk zwavelzuur milieu. |
| DE2130037B2 (de) * | 1971-06-18 | 1977-02-10 | Davy Powergas GmbH, 5000Köln | Verfahren zur herstellung von lactamen |
| DE2130036B2 (de) * | 1971-06-18 | 1977-02-10 | Davy Powergas GmbH, 5000 Köln | Verfahren zur herstellung von lactamen |
| BE790692A (fr) * | 1971-10-29 | 1973-04-27 | Stamicarbon | Procede d'obtention de lactames purs |
| US3852223A (en) * | 1972-07-03 | 1974-12-03 | Dow Chemical Co | Process for disposing of halogen-containing plastics |
| US3859278A (en) * | 1972-12-11 | 1975-01-07 | Stamicarbon | Process for separating lactams |
| NL7410450A (nl) * | 1974-08-05 | 1976-02-09 | Stamicarbon | Werkwijze voor het winnen van epsilon-capro- lactam uit een epsilon-caprolactamzwavelzuur reactiemengsel. |
| NL7601061A (nl) * | 1976-02-03 | 1977-08-05 | Stamicarbon | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuur-reac- tiemengsel. |
| NL7607047A (nl) * | 1976-06-28 | 1977-12-30 | Stamicarbon | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactam-zwavelzuur- -reactiemengsel. |
-
1977
- 1977-01-28 NL NL7700882A patent/NL7700882A/xx not_active Application Discontinuation
-
1978
- 1978-01-18 BE BE184395A patent/BE863012A/xx not_active IP Right Cessation
- 1978-01-20 US US05/871,005 patent/US4133810A/en not_active Expired - Lifetime
- 1978-01-20 CA CA295,417A patent/CA1100961A/en not_active Expired
- 1978-01-24 GB GB2834/78A patent/GB1553358A/en not_active Expired
- 1978-01-26 IT IT47809/78A patent/IT1104146B/it active
- 1978-01-26 FR FR7802190A patent/FR2378769A1/fr active Granted
- 1978-01-27 BR BR7800529A patent/BR7800529A/pt unknown
- 1978-01-27 JP JP821078A patent/JPS5395990A/ja active Pending
- 1978-01-27 ES ES466424A patent/ES466424A1/es not_active Expired
- 1978-01-27 MX MX786801U patent/MX5326E/es unknown
- 1978-01-27 DE DE19782803657 patent/DE2803657A1/de not_active Withdrawn
- 1978-01-27 CH CH94178A patent/CH632250A5/de not_active IP Right Cessation
- 1978-01-30 AR AR270905A patent/AR217673A1/es active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852272A (en) * | 1971-05-07 | 1974-12-03 | Stamicarbon | Process for removing lactams |
| US3879380A (en) * | 1971-12-11 | 1975-04-22 | Stamicarbon | Process for recovery of lactam |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0010666A1 (de) * | 1978-10-16 | 1980-05-14 | BASF Aktiengesellschaft | Verfahren zur kontinuierlichen Herstellung von epsilon-Caprolactam durch Beckmann'sche Umlagerung |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7847809A0 (it) | 1978-01-26 |
| GB1553358A (en) | 1979-09-26 |
| IT1104146B (it) | 1985-10-14 |
| FR2378769A1 (fr) | 1978-08-25 |
| BR7800529A (pt) | 1978-09-12 |
| MX5326E (es) | 1983-06-22 |
| FR2378769B1 (en, 2012) | 1983-02-04 |
| BE863012A (nl) | 1978-07-18 |
| US4133810A (en) | 1979-01-09 |
| JPS5395990A (en) | 1978-08-22 |
| ES466424A1 (es) | 1978-10-16 |
| CA1100961A (en) | 1981-05-12 |
| AR217673A1 (es) | 1980-04-15 |
| CH632250A5 (de) | 1982-09-30 |
| NL7700882A (nl) | 1978-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| 8136 | Disposal/non-payment of the fee for publication/grant |