CA1084919A - 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
- CA1084919A CA1084919A CA269,877A CA269877A CA1084919A CA 1084919 A CA1084919 A CA 1084919A CA 269877 A CA269877 A CA 269877A CA 1084919 A CA1084919 A CA 1084919A
- Authority
- CA
- Canada
- Prior art keywords
- caprolactam
- sulphuric acid
- ammonia
- epsilon
- 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 27
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 9
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract 5
- 239000001117 sulphuric acid Substances 0.000 title claims description 21
- 235000011149 sulphuric acid Nutrition 0.000 title claims description 21
- 238000011084 recovery Methods 0.000 title claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 53
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 19
- 150000003951 lactams Chemical class 0.000 claims description 21
- 239000004291 sulphur dioxide Substances 0.000 claims description 12
- 235000010269 sulphur dioxide Nutrition 0.000 claims description 12
- 239000007789 gas Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 239000000155 melt Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000008246 gaseous mixture Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 12
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 10
- 239000001166 ammonium sulphate Substances 0.000 description 10
- 235000011130 ammonium sulphate Nutrition 0.000 description 10
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000005864 Sulphur Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001323490 Colias gigantea Species 0.000 description 1
- 241000282326 Felis catus Species 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
- 239000002253 acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- -1 oxime lactam Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 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)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Removal Of Specific Substances (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7601061A NL7601061A (nl) | 1976-02-03 | 1976-02-03 | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuur-reac- tiemengsel. |
| NL7601061 | 1976-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084919A true CA1084919A (en) | 1980-09-02 |
Family
ID=19825559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,877A Expired CA1084919A (en) | 1976-02-03 | 1977-01-17 | PROCESS FOR THE RECOVERY OF .epsilon.-CAPROLACTAM FROM A REACTION MIXTURE OF .epsilon.-CAPROLACTAM AND SULPHURIC ACID |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4081442A (en, 2012) |
| JP (1) | JPS6047253B2 (en, 2012) |
| AR (1) | AR210197A1 (en, 2012) |
| BE (1) | BE850374A (en, 2012) |
| BR (1) | BR7700655A (en, 2012) |
| CA (1) | CA1084919A (en, 2012) |
| CH (1) | CH626063A5 (en, 2012) |
| DE (1) | DE2704561A1 (en, 2012) |
| ES (1) | ES455523A1 (en, 2012) |
| FR (1) | FR2351959A1 (en, 2012) |
| GB (1) | GB1506139A (en, 2012) |
| IT (1) | IT1083460B (en, 2012) |
| MX (1) | MX144993A (en, 2012) |
| NL (1) | NL7601061A (en, 2012) |
| SU (1) | SU712023A3 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7700882A (nl) * | 1977-01-28 | 1978-08-01 | Stamicarbon | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuurreac- tiemengsel. |
| DE2900426A1 (de) * | 1978-01-10 | 1979-07-12 | Inst Francais Du Petrol | Verfahren zur umwandlung von ammonium- imidodisulfat, ammoniumsulfamat und ammoniumdithionat in schwefeldioxid und ammoniak |
| US4677074A (en) * | 1984-06-21 | 1987-06-30 | The Lubrizol Corporation | Process for reducing sulfur-containing contaminants in sulfonated hydrocarbons |
| FR2786180B1 (fr) * | 1998-11-19 | 2001-11-23 | Rhone Poulenc Fibres | Procede de traitement de lactames et procede de purification d'un lactame |
| TWI520944B (zh) * | 2015-02-13 | 2016-02-11 | 中國石油化學工業開發股份有限公司 | 己內醯胺之製造方法及其系統 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3264060A (en) * | 1966-08-02 | Simultaneous recovery of pure ammoni- um sulfate and pure lactams from re- arrangement mixtures of alicyclic ketoximes | ||
| DE850746C (de) * | 1944-12-17 | 1952-09-29 | Basf Ag | Verfahren zum Aufarbeiten von durch Basen verunreinigten Lactamen |
| US2723266A (en) * | 1952-05-15 | 1955-11-08 | British Celanese | Process for producing amides and lactams |
| NL132894C (en, 2012) * | 1961-08-30 | 1900-01-01 | ||
| DE1220398B (de) * | 1962-11-15 | 1966-07-07 | Roehm & Haas Gmbh | Gewinnung von Ammoniak und Schwefeldioxyd aus Ammoniumbisulfat enthaltenden Abfallschwefelsaeuren |
| GB1040807A (en) * | 1963-07-03 | 1966-09-01 | Toyo Rayon Co Ltd | Process for refining crude lactams |
| NL6403701A (en, 2012) * | 1964-04-08 | 1965-10-11 | ||
| NL7008837A (en, 2012) * | 1970-06-17 | 1971-12-21 | ||
| US3725391A (en) * | 1970-11-30 | 1973-04-03 | Toray Industries | Process for the preparation of lactams from cycloalkanone oximes |
| US3852273A (en) * | 1971-05-07 | 1974-12-03 | Stamicarbon | Process for preparing and recovering lactams |
| FR2138545B1 (en, 2012) * | 1971-05-27 | 1973-05-25 | Inst Francais Du Petrole | |
| 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 |
| US3859278A (en) * | 1972-12-11 | 1975-01-07 | Stamicarbon | Process for separating lactams |
| CH593934A5 (en, 2012) * | 1974-09-03 | 1977-12-30 | Inventa Ag |
-
1976
- 1976-02-03 NL NL7601061A patent/NL7601061A/xx unknown
-
1977
- 1977-01-14 BE BE174071A patent/BE850374A/xx not_active IP Right Cessation
- 1977-01-17 CA CA269,877A patent/CA1084919A/en not_active Expired
- 1977-01-18 GB GB1935/77A patent/GB1506139A/en not_active Expired
- 1977-01-21 MX MX167779A patent/MX144993A/es unknown
- 1977-01-24 JP JP52006685A patent/JPS6047253B2/ja not_active Expired
- 1977-01-24 IT IT47772/77A patent/IT1083460B/it active
- 1977-01-28 AR AR266345A patent/AR210197A1/es active
- 1977-01-28 SU SU772444805A patent/SU712023A3/ru active
- 1977-01-31 FR FR7702580A patent/FR2351959A1/fr active Granted
- 1977-02-01 ES ES455523A patent/ES455523A1/es not_active Expired
- 1977-02-01 CH CH119977A patent/CH626063A5/de not_active IP Right Cessation
- 1977-02-02 US US05/765,102 patent/US4081442A/en not_active Expired - Lifetime
- 1977-02-02 BR BR7700655A patent/BR7700655A/pt unknown
- 1977-02-03 DE DE19772704561 patent/DE2704561A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| BE850374A (nl) | 1977-07-14 |
| CH626063A5 (en, 2012) | 1981-10-30 |
| SU712023A3 (ru) | 1980-01-25 |
| BR7700655A (pt) | 1977-10-11 |
| DE2704561A1 (de) | 1977-08-04 |
| US4081442A (en) | 1978-03-28 |
| JPS5295686A (en) | 1977-08-11 |
| FR2351959A1 (fr) | 1977-12-16 |
| NL7601061A (nl) | 1977-08-05 |
| FR2351959B1 (en, 2012) | 1981-12-24 |
| IT1083460B (it) | 1985-05-21 |
| JPS6047253B2 (ja) | 1985-10-21 |
| ES455523A1 (es) | 1978-01-16 |
| AR210197A1 (es) | 1977-06-30 |
| MX144993A (es) | 1981-12-10 |
| GB1506139A (en) | 1978-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |