DE2628085C3 - Verfahren zur Herstellung eines Lactams - Google Patents
Verfahren zur Herstellung eines LactamsInfo
- Publication number
- DE2628085C3 DE2628085C3 DE2628085A DE2628085A DE2628085C3 DE 2628085 C3 DE2628085 C3 DE 2628085C3 DE 2628085 A DE2628085 A DE 2628085A DE 2628085 A DE2628085 A DE 2628085A DE 2628085 C3 DE2628085 C3 DE 2628085C3
- Authority
- DE
- Germany
- Prior art keywords
- lactam
- concentration
- sulfuric acid
- temperature
- concentrated
- 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
- 150000003951 lactams Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002351 wastewater Substances 0.000 claims description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 13
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002485 combustion reaction Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 230000008707 rearrangement Effects 0.000 claims description 6
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000000605 extraction Methods 0.000 description 17
- 239000003960 organic solvent Substances 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
- D04H1/74—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being orientated, e.g. in parallel (anisotropic fleeces)
-
- 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
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B7/00—Connections of rods or tubes, e.g. of non-circular section, mutually, including resilient connections
- F16B7/04—Clamping or clipping connections
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
- B23Q2701/00—Members which are comprised in the general build-up of a form of the machine
- B23Q2701/01—Frames or slideways for lathes; Frames for boring machines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
- B23Q2703/00—Work clamping
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W10/00—Technologies for wastewater treatment
- Y02W10/30—Wastewater or sewage treatment systems using renewable energies
- Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Physical Water Treatments (AREA)
- Treating Waste Gases (AREA)
- Heat Treatment Of Water, Waste Water Or Sewage (AREA)
- Treatment Of Water By Oxidation Or Reduction (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50079198A JPS523261A (en) | 1975-06-24 | 1975-06-24 | Purification method for polluted water |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2628085A1 DE2628085A1 (de) | 1977-01-27 |
| DE2628085B2 DE2628085B2 (de) | 1979-09-27 |
| DE2628085C3 true DE2628085C3 (de) | 1980-06-26 |
Family
ID=13683258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2628085A Expired DE2628085C3 (de) | 1975-06-24 | 1976-06-23 | Verfahren zur Herstellung eines Lactams |
Country Status (7)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4132498A1 (de) * | 1991-09-30 | 1993-04-01 | Basf Ag | Verfahren zur herstellung von caprolactam durch beckmann'sche umlagerung von cyclohexanonoxim |
| EP0826665A1 (en) * | 1996-09-02 | 1998-03-04 | Dsm N.V. | Recovery of epsilon-caprolactam from aqueous mixtures |
| TW420662B (en) * | 1996-02-17 | 2001-02-01 | Du Pont | Recovery of <epsilon>-caprolactam |
| NL1011936C2 (nl) * | 1999-04-29 | 2000-10-31 | Dsm Nv | Werkwijze voor het bereiden van caprolactam. |
| DE10113113A1 (de) * | 2001-03-16 | 2002-09-19 | Bayer Ag | Nitratreduktion durch SO¶2¶ |
| US7022844B2 (en) | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
| JP2013514335A (ja) | 2009-12-18 | 2013-04-25 | ディーエスエム アイピー アセッツ ビー．ブイ． | 膜処理でのカプロラクタムの回収 |
| EP3305957B1 (en) | 2015-05-29 | 2021-01-06 | Kuraray Co., Ltd. | Fiber sheet |
Family Cites Families (9)
| 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 | ||
| US2973355A (en) * | 1961-02-28 | Process for the production of pure x-caprolactim | ||
| CA557462A (en) * | 1958-05-13 | Schaffler Alfred | PROCESS AND PLANT FOR THE RECOVERY OF .epsilon.-CAPROLACTAM | |
| US3954955A (en) * | 1971-08-31 | 1976-05-04 | Davy Powergas Gmbh | Process for working up the wash solution obtained in the washing of SO2 -containing off-gases |
| GB1367241A (en) * | 1971-02-19 | 1974-09-18 | Zieren Chemiebau Gmbh Dr A | Process for the combustion of ammonium sulphate |
| CA989830A (en) * | 1971-05-07 | 1976-05-25 | Abraham H. De Rooij | Process for preparing and recovering lactams |
| NL164028C (nl) * | 1971-05-07 | 1980-11-17 | Stamicarbon | Werkwijze voor de afscheiding van lactamen. |
| US3992372A (en) * | 1974-04-02 | 1976-11-16 | Basf Aktiengesellschaft | Processing polycaprolactam extraction liquors |
| NL7505130A (nl) * | 1975-05-01 | 1976-11-03 | Stamicarbon | Werkwijze voor de winning van zuiver epsilon- -caprolactam uit een waterige oplossing hiervan. |
-
1975
- 1975-06-24 JP JP50079198A patent/JPS523261A/ja active Granted
-
1976
- 1976-06-18 GB GB25487/76A patent/GB1508942A/en not_active Expired
- 1976-06-21 NL NL7606726A patent/NL7606726A/xx not_active Application Discontinuation
- 1976-06-21 US US05/698,122 patent/US4072678A/en not_active Expired - Lifetime
- 1976-06-23 DE DE2628085A patent/DE2628085C3/de not_active Expired
- 1976-06-23 IT IT24642/76A patent/IT1062414B/it active
- 1976-06-24 FR FR7619199A patent/FR2315502A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56119B2 (US20100223739A1-20100909-C00025.png) | 1981-01-06 |
| JPS523261A (en) | 1977-01-11 |
| FR2315502A1 (fr) | 1977-01-21 |
| DE2628085A1 (de) | 1977-01-27 |
| NL7606726A (nl) | 1976-12-28 |
| GB1508942A (en) | 1978-04-26 |
| US4072678A (en) | 1978-02-07 |
| DE2628085B2 (de) | 1979-09-27 |
| IT1062414B (it) | 1984-10-10 |
| FR2315502B1 (US20100223739A1-20100909-C00025.png) | 1979-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |