CA2288156A1 - Process for recovering caprolactam from a neutralized rearrangement mixture - Google Patents
Process for recovering caprolactam from a neutralized rearrangement mixture Download PDFInfo
- Publication number
- CA2288156A1 CA2288156A1 CA002288156A CA2288156A CA2288156A1 CA 2288156 A1 CA2288156 A1 CA 2288156A1 CA 002288156 A CA002288156 A CA 002288156A CA 2288156 A CA2288156 A CA 2288156A CA 2288156 A1 CA2288156 A1 CA 2288156A1
- Authority
- CA
- Canada
- Prior art keywords
- caprolactam
- water
- phase
- process according
- organic solvent
- 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.)
- Abandoned
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000008707 rearrangement Effects 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012074 organic phase Substances 0.000 claims abstract description 29
- 239000008346 aqueous phase Substances 0.000 claims abstract description 28
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 19
- 239000001166 ammonium sulphate Substances 0.000 claims abstract description 19
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 19
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000012071 phase Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 5
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 238000005406 washing 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
- C07D201/16—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)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1005927 | 1997-04-29 | ||
| NL1005927A NL1005927C2 (nl) | 1997-04-29 | 1997-04-29 | Werkwijze voor het winnen van caprolactam uit een geneutraliseerd omlegmengsel. |
| PCT/NL1998/000216 WO1998049140A1 (en) | 1997-04-29 | 1998-04-20 | Process for recovering caprolactam from a neutralized rearrangement mixture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2288156A1 true CA2288156A1 (en) | 1998-11-05 |
Family
ID=19764875
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002288156A Abandoned CA2288156A1 (en) | 1997-04-29 | 1998-04-20 | Process for recovering caprolactam from a neutralized rearrangement mixture |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0980356A1 (id) |
| JP (1) | JP2001522371A (id) |
| KR (1) | KR20010020300A (id) |
| CN (1) | CN1253546A (id) |
| AU (1) | AU6856598A (id) |
| BG (1) | BG103833A (id) |
| BR (1) | BR9809420A (id) |
| CA (1) | CA2288156A1 (id) |
| CO (1) | CO5040159A1 (id) |
| EA (1) | EA199900982A1 (id) |
| ID (1) | ID23781A (id) |
| NL (1) | NL1005927C2 (id) |
| PL (1) | PL336476A1 (id) |
| SK (1) | SK148799A3 (id) |
| TW (1) | TW408109B (id) |
| WO (1) | WO1998049140A1 (id) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6849731B2 (en) * | 2001-03-01 | 2005-02-01 | Dsm Ip Assets B.V. | Process for recovering and purifying caprolactam from an organic solvent |
| TW200951112A (en) | 2008-06-13 | 2009-12-16 | China Petrochemical Dev Corp | System of recycle caprolactam form rearrangement mixture and method thereof |
| CN101613311B (zh) * | 2008-06-25 | 2013-01-02 | 中国石油化学工业开发股份有限公司 | 从重排混合物中回收己内酰胺的系统和方法 |
| KR101810704B1 (ko) | 2009-12-18 | 2017-12-19 | 캡 쓰리 비 브이 | 막 처리에 의한 카프로락탐 회수방법 |
| CN102212033B (zh) * | 2010-04-07 | 2013-02-27 | 中国科学院过程工程研究所 | 一种降低硫酸铵晶体夹带己内酰胺量的方法 |
| CN102234248A (zh) * | 2010-04-23 | 2011-11-09 | 中国石油化工股份有限公司 | 一种己内酰胺杂质萃取的方法 |
| CN105408313B (zh) * | 2013-07-26 | 2018-11-09 | Cap Iii 有限公司 | 一种工业规模回收己内酰胺和结晶硫酸铵的连续方法 |
| CN106316955A (zh) * | 2016-10-28 | 2017-01-11 | 湖北三宁化工股份有限公司 | 一种高纯度己内酰胺精制装置和净化方法 |
| CN108341763B (zh) * | 2018-04-24 | 2020-12-01 | 河北美邦工程科技股份有限公司 | 一种己内酰胺结晶纯化方法 |
| CN111471015B (zh) * | 2019-01-24 | 2024-01-30 | 中国石油化工股份有限公司 | 一种回收苯蒸残液中己内酰胺的装置和方法 |
| CN109942492A (zh) * | 2019-04-11 | 2019-06-28 | 江苏凌瑞化工科技有限公司 | 一种己内酰胺精制工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1031308B (de) * | 1956-11-10 | 1958-06-04 | Bayer Ag | Verfahren zur Gewinnung von reinem Caprolactam aus dem neutralisierten Reaktionsgemisch der Beckmannschen Umlagerung von Cyclohexanonoxim |
| DE3635363A1 (de) * | 1986-10-17 | 1988-04-21 | Basf Ag | Verfahren zur neutralisation von reaktionsgemischen, die durch beckmann'sche umlagerung von cyclohexanonoxim erhalten worden sind |
| 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 |
| BE1007298A3 (nl) * | 1993-07-19 | 1995-05-09 | Dsm Nv | Werkwijze voor het zuiveren van een water-epsilon-caprolactam mengsel. |
-
1997
- 1997-04-29 NL NL1005927A patent/NL1005927C2/nl not_active IP Right Cessation
-
1998
- 1998-04-20 AU AU68565/98A patent/AU6856598A/en not_active Abandoned
- 1998-04-20 SK SK1487-99A patent/SK148799A3/sk unknown
- 1998-04-20 BR BR9809420-3A patent/BR9809420A/pt not_active IP Right Cessation
- 1998-04-20 CN CN98804541A patent/CN1253546A/zh active Pending
- 1998-04-20 JP JP54684498A patent/JP2001522371A/ja active Pending
- 1998-04-20 EA EA199900982A patent/EA199900982A1/ru unknown
- 1998-04-20 WO PCT/NL1998/000216 patent/WO1998049140A1/en not_active Ceased
- 1998-04-20 CA CA002288156A patent/CA2288156A1/en not_active Abandoned
- 1998-04-20 ID IDW991289A patent/ID23781A/id unknown
- 1998-04-20 EP EP98914149A patent/EP0980356A1/en not_active Withdrawn
- 1998-04-20 PL PL98336476A patent/PL336476A1/xx unknown
- 1998-04-20 KR KR1019997009904A patent/KR20010020300A/ko not_active Withdrawn
- 1998-04-21 TW TW087106075A patent/TW408109B/zh not_active IP Right Cessation
- 1998-04-27 CO CO98023022A patent/CO5040159A1/es unknown
-
1999
- 1999-10-25 BG BG103833A patent/BG103833A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA199900982A1 (ru) | 2000-06-26 |
| KR20010020300A (ko) | 2001-03-15 |
| TW408109B (en) | 2000-10-11 |
| ID23781A (id) | 2000-05-11 |
| CN1253546A (zh) | 2000-05-17 |
| CO5040159A1 (es) | 2001-05-29 |
| NL1005927C2 (nl) | 1998-11-02 |
| BR9809420A (pt) | 2000-06-13 |
| SK148799A3 (en) | 2000-05-16 |
| JP2001522371A (ja) | 2001-11-13 |
| BG103833A (en) | 2000-06-30 |
| WO1998049140A1 (en) | 1998-11-05 |
| EP0980356A1 (en) | 2000-02-23 |
| AU6856598A (en) | 1998-11-24 |
| PL336476A1 (en) | 2000-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |