CA1100961A - PROCESS FOR THE RECOVERY OF .epsilon.-CAPROLACTAM FROM A REACTION MIXTURE OF .epsilon.-CAPROLACTAM AND SULPHURIC ACID - Google Patents
PROCESS FOR THE RECOVERY OF .epsilon.-CAPROLACTAM FROM A REACTION MIXTURE OF .epsilon.-CAPROLACTAM AND SULPHURIC ACIDInfo
- Publication number
- CA1100961A CA1100961A CA295,417A CA295417A CA1100961A CA 1100961 A CA1100961 A CA 1100961A CA 295417 A CA295417 A CA 295417A CA 1100961 A CA1100961 A CA 1100961A
- Authority
- CA
- Canada
- Prior art keywords
- sulphuric acid
- lactam
- ammonium
- caprolactam
- 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.)
- Expired
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 230000008569 process Effects 0.000 title claims abstract description 9
- 238000011084 recovery Methods 0.000 title claims abstract description 9
- 239000001117 sulphuric acid Substances 0.000 title claims description 43
- 235000011149 sulphuric acid Nutrition 0.000 title claims description 43
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 51
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 50
- 150000003951 lactams Chemical class 0.000 claims abstract description 38
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 18
- 239000008246 gaseous mixture Substances 0.000 claims abstract description 17
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 16
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 9
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 claims abstract description 6
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000010269 sulphur dioxide Nutrition 0.000 claims description 21
- 239000004291 sulphur dioxide Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 7
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 23
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 21
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 15
- 239000001166 ammonium sulphate Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 14
- 235000011130 ammonium sulphate Nutrition 0.000 description 14
- 239000007789 gas Substances 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 238000009434 installation Methods 0.000 description 7
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 230000008707 rearrangement Effects 0.000 description 6
- -1 NH4 ions Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 150000001875 compounds Chemical class 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
- 230000000694 effects Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- NPCNOMATAMPYNV-UHFFFAOYSA-N S(=O)(=O)(O)[O-].[NH4+].[NH4+].[NH4+].S(=O)(=O)(O)[O-].S(=O)(=O)(O)[O-] Chemical compound S(=O)(=O)(O)[O-].[NH4+].[NH4+].[NH4+].S(=O)(=O)(O)[O-].S(=O)(=O)(O)[O-] NPCNOMATAMPYNV-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 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
- 239000003054 catalyst Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7700882 | 1977-01-28 | ||
| 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 |
|---|---|
| CA1100961A true CA1100961A (en) | 1981-05-12 |
Family
ID=19827871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,417A Expired CA1100961A (en) | 1977-01-28 | 1978-01-20 | PROCESS FOR THE RECOVERY OF .epsilon.-CAPROLACTAM FROM A REACTION MIXTURE OF .epsilon.-CAPROLACTAM AND SULPHURIC ACID |
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) |
Families Citing this family (2)
| 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 |
| US7022844B2 (en) | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
Family Cites Families (12)
| 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. |
| NL164028C (nl) * | 1971-05-07 | 1980-11-17 | Stamicarbon | Werkwijze voor de afscheiding van lactamen. |
| 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 |
| BE792559A (fr) * | 1971-12-11 | 1973-06-12 | Stamicarbon | Procede pour la separation de lactames |
| 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
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 |
| DE2803657A1 (de) | 1978-08-03 |
| 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 |
|---|---|---|---|
| MKEX | Expiry |