HU220356B - 6-Amino-kapronitril titán-dioxiddal katalizált ciklizálása kaprolaktámmá folyékony fázisban - Google Patents
6-Amino-kapronitril titán-dioxiddal katalizált ciklizálása kaprolaktámmá folyékony fázisban Download PDFInfo
- Publication number
- HU220356B HU220356B HU9801131A HUP9801131A HU220356B HU 220356 B HU220356 B HU 220356B HU 9801131 A HU9801131 A HU 9801131A HU P9801131 A HUP9801131 A HU P9801131A HU 220356 B HU220356 B HU 220356B
- Authority
- HU
- Hungary
- Prior art keywords
- titanium dioxide
- weight
- acid nitrile
- caprolactam
- liquid phase
- Prior art date
Links
- -1 6-amino-caproic acid nitrile Chemical class 0.000 title claims abstract description 28
- 239000007791 liquid phase Substances 0.000 title claims abstract description 6
- 229960002684 aminocaproic acid Drugs 0.000 title claims description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title description 14
- 239000010936 titanium Substances 0.000 title description 2
- 229910052719 titanium Inorganic materials 0.000 title description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 4
- 239000003791 organic solvent mixture Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 1
- GWCFTYITFDWLAY-UHFFFAOYSA-N 1-ethylazepan-2-one Chemical compound CCN1CCCCCC1=O GWCFTYITFDWLAY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CEKXZSQLUFQAOG-UHFFFAOYSA-N barium(2+) oxygen(2-) titanium(4+) Chemical compound [O--].[O--].[Ti+4].[Ba++] CEKXZSQLUFQAOG-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006454 non catalyzed reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C07D201/02—Preparation of lactams
- C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Polyamides (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19517821A DE19517821A1 (de) | 1995-05-18 | 1995-05-18 | Verfahren zur Herstellung von Caprolactam |
| PCT/EP1996/001891 WO1996036600A1 (de) | 1995-05-18 | 1996-05-07 | Titandioxidkatalysierte cyclisierung in flüssiger phase von 6-aminocapronsäurenitril zu caprolactam |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9801131A2 HUP9801131A2 (hu) | 1998-08-28 |
| HUP9801131A3 HUP9801131A3 (en) | 1999-05-28 |
| HU220356B true HU220356B (hu) | 2001-12-28 |
Family
ID=7761968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9801131A HU220356B (hu) | 1995-05-18 | 1996-05-07 | 6-Amino-kapronitril titán-dioxiddal katalizált ciklizálása kaprolaktámmá folyékony fázisban |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0815077A1 (cs) |
| JP (1) | JPH11505230A (cs) |
| KR (1) | KR19990014859A (cs) |
| CN (1) | CN1075810C (cs) |
| AU (1) | AU700098B2 (cs) |
| BG (1) | BG102027A (cs) |
| BR (1) | BR9608470A (cs) |
| CA (1) | CA2218132A1 (cs) |
| CZ (1) | CZ289460B6 (cs) |
| DE (1) | DE19517821A1 (cs) |
| EA (1) | EA199700402A1 (cs) |
| HU (1) | HU220356B (cs) |
| MX (1) | MX9708676A (cs) |
| NO (1) | NO307964B1 (cs) |
| NZ (1) | NZ308485A (cs) |
| PL (1) | PL323389A1 (cs) |
| SK (1) | SK154897A3 (cs) |
| TR (1) | TR199701385T1 (cs) |
| TW (1) | TW340840B (cs) |
| WO (1) | WO1996036600A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19738463C2 (de) * | 1997-09-03 | 1999-09-23 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
| DE19738464A1 (de) * | 1997-09-03 | 1999-03-04 | Basf Ag | Verwendung von Formkörpern als Katalysator zur Herstellung von Caprolactam |
| CN101890370B (zh) * | 2010-08-05 | 2012-05-30 | 上海交通大学 | 基于纳米二氧化钛和聚膦腈的复合光催化剂及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2029540A (en) * | 1935-10-01 | 1936-02-04 | Porteous William | Trailer |
| US2301964A (en) * | 1941-09-12 | 1942-11-17 | Du Pont | Method of preparing lactams |
| JPS4821958B1 (cs) * | 1969-01-28 | 1973-07-02 | ||
| US4625023A (en) * | 1985-09-03 | 1986-11-25 | Allied Corporation | Selective conversion of aliphatic and aromatic aminonitriles and/or dinitriles into lactams |
| US4628085A (en) * | 1985-09-03 | 1986-12-09 | Allied Corporation | Use of silica catalyst for selective production of lactams |
| JP2969779B2 (ja) * | 1990-05-01 | 1999-11-02 | 株式会社明電舎 | 濃淡画像処理装置 |
| DE4339648A1 (de) * | 1993-11-20 | 1995-05-24 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
-
1995
- 1995-05-18 DE DE19517821A patent/DE19517821A1/de not_active Withdrawn
-
1996
- 1996-05-02 TW TW085105277A patent/TW340840B/zh active
- 1996-05-07 MX MX9708676A patent/MX9708676A/es unknown
- 1996-05-07 EA EA199700402A patent/EA199700402A1/ru unknown
- 1996-05-07 JP JP8534516A patent/JPH11505230A/ja active Pending
- 1996-05-07 NZ NZ308485A patent/NZ308485A/xx unknown
- 1996-05-07 CZ CZ19973578A patent/CZ289460B6/cs not_active IP Right Cessation
- 1996-05-07 HU HU9801131A patent/HU220356B/hu not_active IP Right Cessation
- 1996-05-07 CN CN96194001A patent/CN1075810C/zh not_active Expired - Fee Related
- 1996-05-07 CA CA002218132A patent/CA2218132A1/en not_active Abandoned
- 1996-05-07 WO PCT/EP1996/001891 patent/WO1996036600A1/de not_active Application Discontinuation
- 1996-05-07 TR TR97/01385T patent/TR199701385T1/xx unknown
- 1996-05-07 BR BR9608470A patent/BR9608470A/pt unknown
- 1996-05-07 EP EP96919687A patent/EP0815077A1/de not_active Withdrawn
- 1996-05-07 KR KR1019970708204A patent/KR19990014859A/ko not_active Ceased
- 1996-05-07 PL PL96323389A patent/PL323389A1/xx unknown
- 1996-05-07 SK SK1548-97A patent/SK154897A3/sk unknown
- 1996-05-07 AU AU58147/96A patent/AU700098B2/en not_active Ceased
-
1997
- 1997-11-06 BG BG102027A patent/BG102027A/xx unknown
- 1997-11-17 NO NO975268A patent/NO307964B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9801131A2 (hu) | 1998-08-28 |
| CZ289460B6 (cs) | 2002-01-16 |
| BR9608470A (pt) | 1998-12-29 |
| CN1184467A (zh) | 1998-06-10 |
| NO975268D0 (no) | 1997-11-17 |
| TR199701385T1 (xx) | 1998-04-21 |
| DE19517821A1 (de) | 1996-11-21 |
| JPH11505230A (ja) | 1999-05-18 |
| HUP9801131A3 (en) | 1999-05-28 |
| SK154897A3 (en) | 1998-07-08 |
| CZ357897A3 (cs) | 1998-04-15 |
| CN1075810C (zh) | 2001-12-05 |
| NO307964B1 (no) | 2000-06-26 |
| NO975268L (no) | 1997-11-17 |
| MX9708676A (es) | 1998-02-28 |
| PL323389A1 (en) | 1998-03-30 |
| CA2218132A1 (en) | 1996-11-21 |
| NZ308485A (en) | 2000-01-28 |
| TW340840B (en) | 1998-09-21 |
| AU700098B2 (en) | 1998-12-24 |
| KR19990014859A (ko) | 1999-02-25 |
| WO1996036600A1 (de) | 1996-11-21 |
| AU5814796A (en) | 1996-11-29 |
| EP0815077A1 (de) | 1998-01-07 |
| EA199700402A1 (ru) | 1999-06-24 |
| BG102027A (en) | 1998-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100310508B1 (ko) | 카프로락탐의 제조 방법 | |
| HU220356B (hu) | 6-Amino-kapronitril titán-dioxiddal katalizált ciklizálása kaprolaktámmá folyékony fázisban | |
| AU705339B2 (en) | Preparation of caprolactam | |
| MXPA97008676A (en) | Caprolact preparation | |
| RU2199528C2 (ru) | Способ циклизирующего гидролиза аминонитрила в лактам | |
| JPH026414A (ja) | イソブチレンの製造法 | |
| US7217818B2 (en) | Purification of caprolactam | |
| JP4465731B2 (ja) | ε−カプロラクタムの製造方法 | |
| AU718411B2 (en) | Preparation of polycaprolactam | |
| HU192998B (en) | Process for producing 5-vinyl-7-pyrrolydinone with decomposing n-oxide of their 5-dimethyl-aminoetyl-derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |