JPS6047253B2 - ε−カプロラクタムの回収方法 - Google Patents
ε−カプロラクタムの回収方法Info
- Publication number
- JPS6047253B2 JPS6047253B2 JP52006685A JP668577A JPS6047253B2 JP S6047253 B2 JPS6047253 B2 JP S6047253B2 JP 52006685 A JP52006685 A JP 52006685A JP 668577 A JP668577 A JP 668577A JP S6047253 B2 JPS6047253 B2 JP S6047253B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfuric acid
- ammonium
- caprolactam
- mixture
- tube
- 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
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 22
- 238000011084 recovery Methods 0.000 title claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 40
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 38
- 150000003951 lactams Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical group N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 16
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 238000006386 neutralization reaction Methods 0.000 claims description 15
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 claims description 14
- 150000003863 ammonium salts Chemical class 0.000 claims description 14
- 239000007789 gas Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 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 claims description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 239000000047 product 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
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 4
- 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
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000011593 sulfur Substances 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
- 238000006237 Beckmann rearrangement reaction Methods 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 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
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002367 phosphate rock Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Inorganic materials S=O XTQHKBHJIVJGKJ-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)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Removal Of Specific Substances (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 (2)
| Publication Number | Publication Date |
|---|---|
| JPS5295686A JPS5295686A (en) | 1977-08-11 |
| JPS6047253B2 true JPS6047253B2 (ja) | 1985-10-21 |
Family
ID=19825559
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP52006685A Expired JPS6047253B2 (ja) | 1976-02-03 | 1977-01-24 | ε−カプロラクタムの回収方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4081442A (https=) |
| JP (1) | JPS6047253B2 (https=) |
| AR (1) | AR210197A1 (https=) |
| BE (1) | BE850374A (https=) |
| BR (1) | BR7700655A (https=) |
| CA (1) | CA1084919A (https=) |
| CH (1) | CH626063A5 (https=) |
| DE (1) | DE2704561A1 (https=) |
| ES (1) | ES455523A1 (https=) |
| FR (1) | FR2351959A1 (https=) |
| GB (1) | GB1506139A (https=) |
| IT (1) | IT1083460B (https=) |
| MX (1) | MX144993A (https=) |
| NL (1) | NL7601061A (https=) |
| SU (1) | SU712023A3 (https=) |
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 (https=) * | 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 (https=) * | 1964-04-08 | 1965-10-11 | ||
| NL7008837A (https=) * | 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 |
| CA989830A (en) * | 1971-05-07 | 1976-05-25 | Abraham H. De Rooij | Process for preparing and recovering lactams |
| FR2138545B1 (https=) * | 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 (https=) * | 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 CH CH119977A patent/CH626063A5/de not_active IP Right Cessation
- 1977-02-01 ES ES455523A patent/ES455523A1/es not_active Expired
- 1977-02-02 BR BR7700655A patent/BR7700655A/pt unknown
- 1977-02-02 US US05/765,102 patent/US4081442A/en not_active Expired - Lifetime
- 1977-02-03 DE DE19772704561 patent/DE2704561A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| MX144993A (es) | 1981-12-10 |
| SU712023A3 (ru) | 1980-01-25 |
| BE850374A (nl) | 1977-07-14 |
| FR2351959A1 (fr) | 1977-12-16 |
| CA1084919A (en) | 1980-09-02 |
| BR7700655A (pt) | 1977-10-11 |
| JPS5295686A (en) | 1977-08-11 |
| DE2704561A1 (de) | 1977-08-04 |
| CH626063A5 (https=) | 1981-10-30 |
| NL7601061A (nl) | 1977-08-05 |
| AR210197A1 (es) | 1977-06-30 |
| ES455523A1 (es) | 1978-01-16 |
| GB1506139A (en) | 1978-04-05 |
| IT1083460B (it) | 1985-05-21 |
| FR2351959B1 (https=) | 1981-12-24 |
| US4081442A (en) | 1978-03-28 |
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