TW568793B - Process for recovering caprolactam from aqueous caprolactam product - Google Patents
Process for recovering caprolactam from aqueous caprolactam product Download PDFInfo
- Publication number
- TW568793B TW568793B TW091119258A TW91119258A TW568793B TW 568793 B TW568793 B TW 568793B TW 091119258 A TW091119258 A TW 091119258A TW 91119258 A TW91119258 A TW 91119258A TW 568793 B TW568793 B TW 568793B
- Authority
- TW
- Taiwan
- Prior art keywords
- caprolactam
- product
- alkali metal
- metal hydroxide
- added
- Prior art date
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 376
- 238000000034 method Methods 0.000 title claims abstract description 40
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000012535 impurity Substances 0.000 claims abstract description 24
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims abstract description 23
- 238000010924 continuous production Methods 0.000 claims abstract 3
- 238000004821 distillation Methods 0.000 claims description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 32
- 229910052783 alkali metal Inorganic materials 0.000 claims description 22
- 238000009835 boiling Methods 0.000 claims description 20
- 150000001340 alkali metals Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 12
- 238000011049 filling Methods 0.000 claims description 11
- 230000002079 cooperative effect Effects 0.000 claims description 9
- -1 hexamethylene Chemical group 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 7
- 201000006292 polyarteritis nodosa Diseases 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 6
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000002474 experimental method Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 150000003951 lactams Chemical class 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000011437 continuous method Methods 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- AKRJQFGOFJIQMW-UHFFFAOYSA-M NC(C(=O)[O-])CCCC.[Na+] Chemical compound NC(C(=O)[O-])CCCC.[Na+] AKRJQFGOFJIQMW-UHFFFAOYSA-M 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- 230000008033 biological extinction Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 claims 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 230000008707 rearrangement Effects 0.000 claims 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 238000004611 spectroscopical analysis Methods 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 1
- 229940113721 aminocaproate Drugs 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 102220097503 rs773841328 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000012085 test solution 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203217 | 2001-08-27 | ||
| EP01203215 | 2001-08-27 | ||
| EP01203214 | 2001-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW568793B true TW568793B (en) | 2004-01-01 |
Family
ID=27224307
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091119258A TW568793B (en) | 2001-08-27 | 2002-08-26 | Process for recovering caprolactam from aqueous caprolactam product |
| TW091119262A TWI311989B (en) | 2001-08-27 | 2002-08-26 | Process for distilling alkaline caprolactam product at reduced pressure |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091119262A TWI311989B (en) | 2001-08-27 | 2002-08-26 | Process for distilling alkaline caprolactam product at reduced pressure |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US20050029086A1 (enExample) |
| EP (2) | EP1423369B1 (enExample) |
| JP (2) | JP4351908B2 (enExample) |
| KR (2) | KR100907146B1 (enExample) |
| CN (2) | CN1252050C (enExample) |
| AT (1) | ATE498611T1 (enExample) |
| AU (2) | AU2002313611A1 (enExample) |
| BR (2) | BR0212067A (enExample) |
| CO (2) | CO5560549A2 (enExample) |
| CZ (1) | CZ2004296A3 (enExample) |
| DE (1) | DE60239205D1 (enExample) |
| EA (2) | EA006481B1 (enExample) |
| ES (1) | ES2429363T3 (enExample) |
| MX (1) | MX298589B (enExample) |
| MY (2) | MY144901A (enExample) |
| PL (2) | PL370035A1 (enExample) |
| TW (2) | TW568793B (enExample) |
| WO (2) | WO2003018550A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050029086A1 (en) * | 2001-08-27 | 2005-02-10 | Groot Zevert Louise A | Process for distilling alkaline caprolactam product at reduced pressure |
| US7022844B2 (en) | 2002-09-21 | 2006-04-04 | Honeywell International Inc. | Amide-based compounds, production, recovery, purification and uses thereof |
| JP6320413B2 (ja) * | 2012-12-19 | 2018-05-09 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | シクロヘキサノンオキシムのベックマン転位からの精製カプロラクタムの製造方法 |
| US8841445B2 (en) | 2012-12-19 | 2014-09-23 | Basf Se | Process for preparing purified caprolactam from the Beckmann rearrangement of cyclohexane oxime |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE202870C (enExample) | ||||
| CH549020A (de) * | 1970-12-22 | 1974-05-15 | Inventa Ag | Verfahren zur reinigung von lactamen. |
| NL7308100A (enExample) * | 1973-06-12 | 1974-12-16 | ||
| DE3030735A1 (de) * | 1980-08-14 | 1982-03-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung von caprolactam durch spaltung von oligomeren des caprolactams |
| NL8102280A (nl) * | 1981-05-09 | 1982-12-01 | Stamicarbon | Werkwijze voor het zuiveren van epsilon-caprolactam. |
| US4720328A (en) * | 1981-06-26 | 1988-01-19 | Akzona Incorporated | Method for removing impurities from caprolactam |
| DD202870A1 (de) * | 1981-09-29 | 1983-10-05 | Leuna Werke Veb | Destillative reinigung von epsilon-caprolactam |
| IT1222419B (it) * | 1987-07-31 | 1990-09-05 | Friuli Chim Spa | Procedimento di purificazione del caprolattame |
| DE3729853A1 (de) * | 1987-09-05 | 1989-03-23 | Basf Ag | Verfahren zur aufarbeitung von destillationsrueckstaenden, die bei der reinigung von caprolactam anfallen |
| US5496641A (en) * | 1991-06-13 | 1996-03-05 | Nippon Sheet Glass Co., Ltd. | Plastic lens |
| DE4407222A1 (de) * | 1994-03-04 | 1995-09-07 | Basf Ag | Verfahren zur Rückgewinnung von Caprolactam aus Oliogo- und/oder Polymeren des Caprolactams |
| DE19500041A1 (de) † | 1995-01-03 | 1996-07-04 | Basf Ag | Verfahren zur kontinuierlichen Reinigung von aus 6-Aminocapronitril hergestelltem Roh-Caprolactam |
| FR2809395B1 (fr) † | 2000-05-26 | 2002-07-19 | Rhodia Polyamide Intermediates | Procede de purification de lactames |
| JP2002145863A (ja) † | 2000-11-02 | 2002-05-22 | Mitsubishi Chemicals Corp | ε−カプロラクタムの精製方法 |
| DE60239191D1 (de) † | 2001-03-01 | 2011-03-31 | Dsm Ip Assets Bv | Verfahren zur rückgewinnung und aufreinigung von caprolactam aus einem organischem lösungsmittel |
| US20050029086A1 (en) * | 2001-08-27 | 2005-02-10 | Groot Zevert Louise A | Process for distilling alkaline caprolactam product at reduced pressure |
-
2002
- 2002-08-23 US US10/487,673 patent/US20050029086A1/en not_active Abandoned
- 2002-08-23 EA EA200400359A patent/EA006481B1/ru not_active IP Right Cessation
- 2002-08-23 KR KR1020047002816A patent/KR100907146B1/ko not_active Expired - Lifetime
- 2002-08-23 CZ CZ2004296A patent/CZ2004296A3/cs unknown
- 2002-08-23 DE DE60239205T patent/DE60239205D1/de not_active Expired - Lifetime
- 2002-08-23 US US10/486,727 patent/US7615137B2/en not_active Expired - Lifetime
- 2002-08-23 AU AU2002313611A patent/AU2002313611A1/en not_active Abandoned
- 2002-08-23 JP JP2003523225A patent/JP4351908B2/ja not_active Expired - Fee Related
- 2002-08-23 ES ES02753297T patent/ES2429363T3/es not_active Expired - Lifetime
- 2002-08-23 AT AT02753298T patent/ATE498611T1/de not_active IP Right Cessation
- 2002-08-23 CN CNB028166736A patent/CN1252050C/zh not_active Expired - Lifetime
- 2002-08-23 BR BR0212067-4A patent/BR0212067A/pt not_active IP Right Cessation
- 2002-08-23 WO PCT/NL2002/000559 patent/WO2003018550A1/en not_active Ceased
- 2002-08-23 EP EP02753297.7A patent/EP1423369B1/en not_active Expired - Lifetime
- 2002-08-23 PL PL02370035A patent/PL370035A1/xx not_active IP Right Cessation
- 2002-08-23 KR KR20047002830A patent/KR20040031007A/ko not_active Ceased
- 2002-08-23 MX MXPA04001793 patent/MX298589B/es active IP Right Grant
- 2002-08-23 WO PCT/NL2002/000558 patent/WO2003018562A1/en not_active Ceased
- 2002-08-23 CN CNB028208226A patent/CN1284774C/zh not_active Expired - Lifetime
- 2002-08-23 BR BR0212118-2A patent/BR0212118A/pt not_active IP Right Cessation
- 2002-08-23 EP EP02753298.5A patent/EP1423361B8/en not_active Expired - Lifetime
- 2002-08-23 JP JP2003523214A patent/JP4368197B2/ja not_active Expired - Fee Related
- 2002-08-23 AU AU2002313612A patent/AU2002313612A/xx not_active Withdrawn
- 2002-08-23 PL PL02367897A patent/PL367897A1/xx unknown
- 2002-08-23 EA EA200400360A patent/EA005831B1/ru not_active IP Right Cessation
- 2002-08-26 TW TW091119258A patent/TW568793B/zh not_active IP Right Cessation
- 2002-08-26 TW TW091119262A patent/TWI311989B/zh not_active IP Right Cessation
- 2002-08-27 MY MYPI20023186A patent/MY144901A/en unknown
- 2002-08-27 MY MYPI20023187A patent/MY144316A/en unknown
-
2004
- 2004-02-18 CO CO04013833A patent/CO5560549A2/es not_active Application Discontinuation
- 2004-03-09 CO CO04021423A patent/CO5560607A2/es not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |