DE2252891A1 - Verfahren zur gewinnung reiner lactame - Google Patents
Verfahren zur gewinnung reiner lactameInfo
- Publication number
- DE2252891A1 DE2252891A1 DE2252891A DE2252891A DE2252891A1 DE 2252891 A1 DE2252891 A1 DE 2252891A1 DE 2252891 A DE2252891 A DE 2252891A DE 2252891 A DE2252891 A DE 2252891A DE 2252891 A1 DE2252891 A1 DE 2252891A1
- Authority
- DE
- Germany
- Prior art keywords
- lactam
- solution
- water
- organic solvent
- emulsion
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000003951 lactams Chemical class 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 47
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 22
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 22
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 14
- 239000000839 emulsion Substances 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000010349 pulsation Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 230000010355 oscillation Effects 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 21
- 239000012074 organic phase Substances 0.000 description 18
- 239000010410 layer Substances 0.000 description 15
- 238000002156 mixing Methods 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 238000000926 separation method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 239000001166 ammonium sulphate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- WYZDXEKUWRCKOB-YDSAWKJFSA-N Mestanolone Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@](C)(O)[C@@]2(C)CC1 WYZDXEKUWRCKOB-YDSAWKJFSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- -1 alicyclic oximes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005201 scrubbing 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
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7114904,A NL171893C (nl) | 1971-10-29 | 1971-10-29 | Werkwijze voor de winning van zuiver epsilon-aminocaprolactam. |
| NL7211586A NL7211586A (en) | 1972-08-25 | 1972-08-25 | High-purity epsilon-caprolactam prodn - by intramolecular rearrangement of cyclohexanone oxime with acid catalyst followed by |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2252891A1 true DE2252891A1 (de) | 1973-05-03 |
Family
ID=26644695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2252891A Ceased DE2252891A1 (de) | 1971-10-29 | 1972-10-27 | Verfahren zur gewinnung reiner lactame |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3850910A (enExample) |
| JP (1) | JPS5335079B2 (enExample) |
| AR (1) | AR193140A1 (enExample) |
| BE (1) | BE790692A (enExample) |
| CH (1) | CH574414A5 (enExample) |
| CS (1) | CS183671B2 (enExample) |
| DD (1) | DD101668A5 (enExample) |
| DE (1) | DE2252891A1 (enExample) |
| FR (1) | FR2158051B1 (enExample) |
| GB (1) | GB1399000A (enExample) |
| IT (1) | IT966829B (enExample) |
| PL (1) | PL82397B1 (enExample) |
| RO (1) | RO64765A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7505130A (nl) * | 1975-05-01 | 1976-11-03 | Stamicarbon | Werkwijze voor de winning van zuiver epsilon- -caprolactam uit een waterige oplossing hiervan. |
| NL7601061A (nl) * | 1976-02-03 | 1977-08-05 | Stamicarbon | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuur-reac- tiemengsel. |
| NL7700882A (nl) * | 1977-01-28 | 1978-08-01 | Stamicarbon | Werkwijze voor het winnen van epsilon-caprolac- tam uit een epsilon-caprolactamzwavelzuurreac- tiemengsel. |
| IT1173261B (it) * | 1984-02-08 | 1987-06-18 | Snia Bpd Spa | Procedimento di purificazione del caprolattame |
| JP2782919B2 (ja) * | 1990-06-12 | 1998-08-06 | 宇部興産株式会社 | ラクタム含有有機溶液の精製方法 |
| JP2601945B2 (ja) * | 1990-11-21 | 1997-04-23 | 宇部興産株式会社 | ラクタム油の精製方法 |
| JP2601946B2 (ja) * | 1990-11-21 | 1997-04-23 | 宇部興産株式会社 | ラクタム含有溶液の精製方法 |
| BE1011047A3 (nl) * | 1997-03-17 | 1999-04-06 | Dsm Nv | Werkwijze voor het zuiveren van caprolactam. |
| US7022844B2 (en) * | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1261891A (fr) * | 1959-10-09 | 1961-05-26 | Stamicarbon | Procédé pour séparer un lactame d'un mélange réactionnel acide |
-
0
- BE BE790692D patent/BE790692A/xx not_active IP Right Cessation
-
1972
- 1972-10-26 CH CH1568672A patent/CH574414A5/xx not_active IP Right Cessation
- 1972-10-27 DD DD166519A patent/DD101668A5/xx unknown
- 1972-10-27 GB GB4973372A patent/GB1399000A/en not_active Expired
- 1972-10-27 CS CS7200007250A patent/CS183671B2/cs unknown
- 1972-10-27 IT IT53686/72A patent/IT966829B/it active
- 1972-10-27 DE DE2252891A patent/DE2252891A1/de not_active Ceased
- 1972-10-28 PL PL1972158529A patent/PL82397B1/pl unknown
- 1972-10-28 JP JP10840072A patent/JPS5335079B2/ja not_active Expired
- 1972-10-30 AR AR244880A patent/AR193140A1/es active
- 1972-10-30 FR FR7238403A patent/FR2158051B1/fr not_active Expired
- 1972-10-30 US US00301726A patent/US3850910A/en not_active Expired - Lifetime
- 1972-10-30 RO RO7272673A patent/RO64765A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3850910A (en) | 1974-11-26 |
| IT966829B (it) | 1974-02-20 |
| CH574414A5 (enExample) | 1976-04-15 |
| GB1399000A (en) | 1975-06-25 |
| PL82397B1 (en) | 1975-10-31 |
| FR2158051A1 (enExample) | 1973-06-08 |
| FR2158051B1 (enExample) | 1976-05-21 |
| JPS5335079B2 (enExample) | 1978-09-25 |
| JPS4852785A (enExample) | 1973-07-24 |
| CS183671B2 (en) | 1978-07-31 |
| BE790692A (fr) | 1973-04-27 |
| RO64765A (ro) | 1980-01-15 |
| AR193140A1 (es) | 1973-03-30 |
| DD101668A5 (enExample) | 1973-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8131 | Rejection |