UA75358C2 - A method for purifying lactams - Google Patents
A method for purifying lactams Download PDFInfo
- Publication number
- UA75358C2 UA75358C2 UA2002119376A UA2002119376A UA75358C2 UA 75358 C2 UA75358 C2 UA 75358C2 UA 2002119376 A UA2002119376 A UA 2002119376A UA 2002119376 A UA2002119376 A UA 2002119376A UA 75358 C2 UA75358 C2 UA 75358C2
- Authority
- UA
- Ukraine
- Prior art keywords
- lactam
- distillation
- column
- compounds
- fact
- Prior art date
Links
- 150000003951 lactams Chemical class 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 78
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 111
- 238000004821 distillation Methods 0.000 claims abstract description 105
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 238000000746 purification Methods 0.000 claims abstract description 29
- 230000007062 hydrolysis Effects 0.000 claims abstract description 23
- 238000001704 evaporation Methods 0.000 claims abstract description 16
- 230000008020 evaporation Effects 0.000 claims abstract description 16
- 239000012429 reaction media Substances 0.000 claims abstract description 16
- 125000005219 aminonitrile group Chemical group 0.000 claims abstract description 7
- 238000011282 treatment Methods 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 208000005156 Dehydration Diseases 0.000 claims description 14
- 238000006297 dehydration reaction Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 230000018044 dehydration Effects 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 11
- 238000011084 recovery Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 8
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 5
- 239000012808 vapor phase Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000004679 hydroxides Chemical class 0.000 claims 2
- 101100338312 Clostridium botulinum C phage HA-17 gene Proteins 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004064 recycling Methods 0.000 abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 45
- 239000002585 base Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000009434 installation Methods 0.000 description 10
- 239000012535 impurity Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- -1 yarn Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical class NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/90—Particular type of heating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0006784A FR2809395B1 (fr) | 2000-05-26 | 2000-05-26 | Procede de purification de lactames |
PCT/FR2001/001644 WO2001090065A1 (fr) | 2000-05-26 | 2001-05-28 | Procede de purification de lactames |
Publications (1)
Publication Number | Publication Date |
---|---|
UA75358C2 true UA75358C2 (en) | 2006-04-17 |
Family
ID=8850676
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA2002119376A UA75358C2 (en) | 2000-05-26 | 2001-05-28 | A method for purifying lactams |
Country Status (19)
Country | Link |
---|---|
US (2) | US7384518B2 (ru) |
EP (2) | EP1289948B1 (ru) |
JP (1) | JP4234928B2 (ru) |
KR (1) | KR100546988B1 (ru) |
CN (1) | CN100372835C (ru) |
AR (1) | AR028636A1 (ru) |
AT (1) | ATE516267T1 (ru) |
AU (1) | AU2001274137A1 (ru) |
BR (1) | BR0111347B1 (ru) |
CA (1) | CA2409984A1 (ru) |
FR (1) | FR2809395B1 (ru) |
HU (1) | HUP0302039A2 (ru) |
MX (1) | MXPA02011471A (ru) |
PL (1) | PL359094A1 (ru) |
RU (1) | RU2230059C1 (ru) |
SK (1) | SK16592002A3 (ru) |
TW (1) | TWI286543B (ru) |
UA (1) | UA75358C2 (ru) |
WO (1) | WO2001090065A1 (ru) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3667140B2 (ja) * | 1999-03-04 | 2005-07-06 | パイオニア株式会社 | ディスクチェンジャ装置 |
EP1423361B8 (en) † | 2001-08-27 | 2018-05-23 | Cap Iii B.V. | Process for recovering caprolactam from aqueous caprolactam product using in situ prepared alkali amino caproate |
DE10253094A1 (de) * | 2002-11-13 | 2004-05-27 | Basf Ag | Verfahren zur Reinigung von Caprolactam |
RU2458052C1 (ru) * | 2011-04-15 | 2012-08-10 | Открытое акционерное общество "КуйбышевАзот" | Способ управления процессом дистилляции капролактама |
EP2602276B1 (de) * | 2011-12-08 | 2015-07-29 | PE Polymer Engineering Plant Construction GmbH | Verfahren und Vorrichtung zur Aufbereitung von hoch wasserhaltigem Recyclingcaprolactam bei der kontinuierlichen Herstellung von Polyamid 6 |
KR101573569B1 (ko) * | 2012-12-27 | 2015-12-01 | 롯데케미칼 주식회사 | 분리막 세정 시스템 및 이를 이용한 분리막 세정 방법 |
DE102013107238A1 (de) * | 2013-07-09 | 2015-01-15 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Verfahren zur Rückgewinnung von Epsilon-Caprolactam aus Extraktwasser |
KR102551766B1 (ko) * | 2017-12-28 | 2023-07-06 | 한화솔루션 주식회사 | 라우로락탐의 정제 방법 및 이의 정제 장치 |
CN111747878A (zh) * | 2020-07-14 | 2020-10-09 | 中国石油化工股份有限公司 | 一种己内酰胺减压蒸馏新方法 |
CN111848515A (zh) * | 2020-07-14 | 2020-10-30 | 中国石油化工股份有限公司 | 一种己内酰胺产品的新型精馏方法 |
CN114478343B (zh) * | 2022-02-24 | 2024-07-23 | 江苏扬农化工集团有限公司 | 己内酰胺的精制提纯方法 |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE226560C (ru) | ||||
DE226561C (ru) | ||||
DE226562C (ru) | ||||
DE152914C (ru) | ||||
DE267729C (ru) | ||||
US2208598A (en) | 1938-09-24 | 1940-07-23 | Du Pont | Aliphatic amino-nitriles and process of producing them |
US2357484A (en) | 1941-09-12 | 1944-09-05 | Du Pont | Process for producing compounds containing an n-substituted amide group |
US2762835A (en) | 1953-03-12 | 1956-09-11 | Celanese Corp | Preparation of amino nitriles |
JPS4821958B1 (ru) | 1969-01-28 | 1973-07-02 | ||
US3931308A (en) * | 1973-06-07 | 1976-01-06 | Allied Chemical Corporation | Process for conversion of lysine dihydrochloride to lysine monohydrochloride |
DE2920436A1 (de) * | 1979-05-19 | 1980-12-04 | Bayer Ag | Verfahren zur herstellung von epsilon -caprolacton |
DE2926279A1 (de) * | 1979-06-29 | 1981-01-08 | Basf Ag | Verfahren zur reinigung von caprolactam |
IT8020902A0 (it) * | 1980-03-25 | 1980-03-25 | Snia Viscosa | Procedimento ed apparecchiatura per la separazione continua per via termica di miscele liquide dicomposti termolabili. |
DD152914A1 (de) * | 1980-09-05 | 1981-12-16 | Wolfgang Gruendel | Verfahren zum destillativen reinigen von caprolactam |
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 |
US4767503A (en) * | 1983-08-29 | 1988-08-30 | Allied Corporation | Removal of light impurities from caprolactam by distillation with water |
US4601859A (en) | 1984-05-04 | 1986-07-22 | Allied Corporation | Selective hydrogenation of aliphatic dinitriles to omega-aminonitriles in ammonia with supported, finely dispersed rhodium-containing catalyst |
DD226562A1 (de) * | 1984-09-07 | 1985-08-28 | Leuna Werke Veb | Verfahren zur destillativen und rektifikativen reinigung von caprolactam |
DD226560A1 (de) * | 1984-09-07 | 1985-08-28 | Leuna Werke Veb | Verfahren zum reinigen von caprolactam |
DD226561A1 (de) * | 1984-09-07 | 1985-08-28 | Leuna Werke Veb | Verfahren zur reinigung von caprolactam |
DE3729853A1 (de) * | 1987-09-05 | 1989-03-23 | Basf Ag | Verfahren zur aufarbeitung von destillationsrueckstaenden, die bei der reinigung von caprolactam anfallen |
DE3735054A1 (de) | 1987-10-16 | 1989-04-27 | Basf Ag | Verfahren zur gewinnung von caprolactam aus leichtsiedern oder schwersiedern der caprolactamdestillation oder gemischen derselben |
DD267729A1 (de) * | 1987-12-03 | 1989-05-10 | Leuna Werke Veb | Verfahren zur aufarbeitung von reaktionsgemischen aus der synthese von n-methyl-epsilon-caprolactam |
GB9012453D0 (en) * | 1990-06-05 | 1990-07-25 | Ucb Sa | Process for the manufacture of n-phenylmaleimide |
US5241066A (en) * | 1992-06-25 | 1993-08-31 | Basf Corporation | Method of recovering caprolactam from mixed waste |
DE4235466A1 (de) | 1992-10-21 | 1994-04-28 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Aminonitrilen |
DE4407222A1 (de) * | 1994-03-04 | 1995-09-07 | Basf Ag | Verfahren zur Rückgewinnung von Caprolactam aus Oliogo- und/oder Polymeren des Caprolactams |
US5458740A (en) * | 1994-03-04 | 1995-10-17 | Basf Corporation | Process for the purification of crude caprolactam |
DE4443125A1 (de) * | 1994-12-03 | 1996-06-05 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
FR2728259B1 (fr) | 1994-12-14 | 1997-03-14 | Rhone Poulenc Chimie | Procede d'hemihydrogenation de dinitriles en aminonitriles |
DE19500041A1 (de) | 1995-01-03 | 1996-07-04 | Basf Ag | Verfahren zur kontinuierlichen Reinigung von aus 6-Aminocapronitril hergestelltem Roh-Caprolactam |
DE19548289A1 (de) * | 1995-12-22 | 1997-06-26 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von Caprolactam und Hexamethylendiamin |
FR2751962B1 (fr) * | 1996-08-02 | 1998-09-11 | Rhone Poulenc Fibres | Procede de purification de lactames |
US5990306A (en) * | 1997-09-03 | 1999-11-23 | Alliedsignal Inc. | Process for the purification of caprolactam obtained from the depolymerization of polyamide-containing carpet |
CN1210851A (zh) * | 1997-09-08 | 1999-03-17 | 中国科学院成都有机化学研究所 | 一种提纯乙酸乙酯的方法 |
FR2781796B1 (fr) * | 1998-07-28 | 2000-09-22 | Rhone Poulenc Fibres | Procede de deshydratation de lactame |
DE10029187A1 (de) * | 2000-06-19 | 2001-12-20 | Basf Ag | Verfahren zur Abtrennung von 6-Aminocapronitril aus Gemischen, die 6-Aminocapronitril, Adipodinitril und Hexamethylendiamin enthalten |
-
2000
- 2000-05-26 FR FR0006784A patent/FR2809395B1/fr not_active Expired - Fee Related
-
2001
- 2001-05-28 WO PCT/FR2001/001644 patent/WO2001090065A1/fr active IP Right Grant
- 2001-05-28 JP JP2001586254A patent/JP4234928B2/ja not_active Expired - Fee Related
- 2001-05-28 EP EP01940616A patent/EP1289948B1/fr not_active Expired - Lifetime
- 2001-05-28 UA UA2002119376A patent/UA75358C2/uk unknown
- 2001-05-28 AR ARP010102530A patent/AR028636A1/es unknown
- 2001-05-28 AT AT01940616T patent/ATE516267T1/de not_active IP Right Cessation
- 2001-05-28 MX MXPA02011471A patent/MXPA02011471A/es not_active Application Discontinuation
- 2001-05-28 HU HU0302039A patent/HUP0302039A2/hu unknown
- 2001-05-28 EP EP07023115.4A patent/EP1903032B1/fr not_active Expired - Lifetime
- 2001-05-28 CA CA002409984A patent/CA2409984A1/fr not_active Abandoned
- 2001-05-28 KR KR1020027016054A patent/KR100546988B1/ko not_active IP Right Cessation
- 2001-05-28 SK SK1659-2002A patent/SK16592002A3/sk unknown
- 2001-05-28 PL PL01359094A patent/PL359094A1/xx unknown
- 2001-05-28 AU AU2001274137A patent/AU2001274137A1/en not_active Abandoned
- 2001-05-28 CN CNB018114873A patent/CN100372835C/zh not_active Expired - Fee Related
- 2001-05-28 BR BRPI0111347-0A patent/BR0111347B1/pt not_active IP Right Cessation
- 2001-05-28 TW TW090112812A patent/TWI286543B/zh not_active IP Right Cessation
- 2001-05-28 US US10/296,512 patent/US7384518B2/en not_active Expired - Fee Related
- 2001-05-28 RU RU2002135089/04A patent/RU2230059C1/ru not_active IP Right Cessation
-
2008
- 2008-05-29 US US12/155,065 patent/US8231765B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20040014965A1 (en) | 2004-01-22 |
WO2001090065A1 (fr) | 2001-11-29 |
PL359094A1 (en) | 2004-08-23 |
CA2409984A1 (fr) | 2001-11-29 |
MXPA02011471A (es) | 2004-01-26 |
AR028636A1 (es) | 2003-05-21 |
EP1903032B1 (fr) | 2013-08-14 |
HUP0302039A2 (hu) | 2003-09-29 |
BR0111347B1 (pt) | 2013-02-19 |
CN100372835C (zh) | 2008-03-05 |
US7384518B2 (en) | 2008-06-10 |
FR2809395A1 (fr) | 2001-11-30 |
EP1289948B1 (fr) | 2011-07-13 |
TWI286543B (en) | 2007-09-11 |
AU2001274137A1 (en) | 2001-12-03 |
EP1289948A1 (fr) | 2003-03-12 |
SK16592002A3 (sk) | 2003-07-01 |
KR20030013430A (ko) | 2003-02-14 |
US20080230368A1 (en) | 2008-09-25 |
RU2230059C1 (ru) | 2004-06-10 |
ATE516267T1 (de) | 2011-07-15 |
BR0111347A (pt) | 2003-04-29 |
US8231765B2 (en) | 2012-07-31 |
KR100546988B1 (ko) | 2006-01-26 |
JP2003534321A (ja) | 2003-11-18 |
CN1437582A (zh) | 2003-08-20 |
EP1903032A1 (fr) | 2008-03-26 |
JP4234928B2 (ja) | 2009-03-04 |
FR2809395B1 (fr) | 2002-07-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8231765B2 (en) | Process for the purification of lactams | |
US2971010A (en) | Production of dicarboxylic acid anhydrides | |
CN110835311A (zh) | 一种由环己酮肟制备6-氨基己腈的方法 | |
JP2020514350A (ja) | 有機溶媒抽出を伴わない粗カプロラクタムの溶液からのカプロラクタムの精製方法 | |
CN103864689B (zh) | 一种提纯含水硫酸铵相的蒸发结晶步骤中获得的冷凝液的方法 | |
US3496212A (en) | Process for purifying adiponitrile | |
JPH04187670A (ja) | カプロラクタム水溶液のイオン交換樹脂精製方法 | |
RU2002135089A (ru) | Способ очистки лактамов | |
JP2003519213A (ja) | ラクタムの精製方法 | |
KR102218342B1 (ko) | Hpo 추출 구역으로부터 배출된 무기 공정 액체의 스팀 스트리핑 및 응축 열의 이용 | |
CN111757865B (zh) | 腈系溶剂的纯化方法 | |
US4015946A (en) | Process for recovering ammonium sulphate from aqueous solutions of ammonium sulphate which contain organic compounds | |
US3009954A (en) | Process for the production of sarcosine and related alkylamino-acetic acids | |
US3859278A (en) | Process for separating lactams | |
US4293494A (en) | Method for the purification of raw caprolactam which contains amides and other by-products | |
JPS6026103B2 (ja) | ε−カプロラクタム及び硫安の回収方法 | |
JPH0149349B2 (ru) | ||
US20210198185A1 (en) | Process for recovering adiponitrile | |
US3084996A (en) | Method of regenerating the free and the used hydrochloric acid from aluminium etching baths | |
JPS63227538A (ja) | 1,1′−パ−オキシジシクロヘキシルアミンの熱分解反応混合液からシクロヘキサノンを回収する方法 | |
JP2002145863A (ja) | ε−カプロラクタムの精製方法 | |
JPS59144746A (ja) | メタクリロニトリルの精製方法 |