JP4961209B2 - テトラヒドロアゼピンを含む不純な6−アミノカプロニトリルからカプロラクタムを製造する方法 - Google Patents
テトラヒドロアゼピンを含む不純な6−アミノカプロニトリルからカプロラクタムを製造する方法 Download PDFInfo
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- JP4961209B2 JP4961209B2 JP2006517368A JP2006517368A JP4961209B2 JP 4961209 B2 JP4961209 B2 JP 4961209B2 JP 2006517368 A JP2006517368 A JP 2006517368A JP 2006517368 A JP2006517368 A JP 2006517368A JP 4961209 B2 JP4961209 B2 JP 4961209B2
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- acn
- tha
- water
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- impure
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 122
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 title claims description 3
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 title claims 15
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 11
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000010574 gas phase reaction Methods 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims 2
- -1 unreacted THA Chemical compound 0.000 claims 2
- HTXLVBCGHGHRHL-UHFFFAOYSA-N 5-aminohexanenitrile Chemical compound CC(N)CCCC#N HTXLVBCGHGHRHL-UHFFFAOYSA-N 0.000 description 34
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 238000012856 packing Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000013529 heat transfer fluid Substances 0.000 description 4
- 239000006200 vaporizer Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- YHGJECVSSKXFCJ-KUBAVDMBSA-N (6Z,9Z,12Z,15Z,18Z,21Z)-tetracosahexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O YHGJECVSSKXFCJ-KUBAVDMBSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005669 hydrocyanation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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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
Description
Claims (2)
- アジポニトリルの部分水素化によって得られる不純な6−アミノカプロニトリル(ACN)からカプロラクタム(CL)を製造する方法であって、前記不純な6−アミノカプロニトリルがACNと、最低500ppmのテトラヒドロアゼピンおよびその誘導体(THA)との両方を含むものであり、
(1)前記不純なACNと水との両方が気相中にある状態で、ACNとTHAとの両方を含む前記不純なACNを、脱水触媒の存在下で高温で前記水と接触させて、CL、アンモニア、水、ACN、およびTHAを含む気相反応生成物を生成する工程と、
(2)前記アンモニア、および前記水の大部分を前記気相反応生成物から分離して、未反応ACN、未反応THA、CLおよび少量の前記水を含む溶液を生成し、次いで前記水を前記溶液から分離して、CL、ACN、およびTHAを含む溶融物を生成する工程と、
(3)前記溶融物を低沸点物質除去蒸留塔に導入し、前記THAと前記ACNとの両方の大部分を留出液として除去し、CL、高沸点物質、および多くとも前記THAと前記ACNとの両方の少量部分を塔底物として除去する工程と、
(4)前記塔底物を高沸点物質除去蒸留塔に導入し、CL、および多くとも少量部分の高沸点物質を留出液生成物として除去し、前記高沸点物質の大部分を塔底物として除去する工程と
を含むことを特徴とする方法。 - 工程(2)において、前記気相反応生成物を部分凝縮することによって前記アンモニア、および前記水の大部分を前記気相反応生成物から分離し、アンモニア、および水を含む蒸気流、ならびに水、CL、未反応のACN、およびTHAを含む液化流を生成し、前記蒸気流を蒸留塔の所定の段階に導入し、前記液体流を前記蒸留塔の所定の段階より低い段階に導入し、塔底物として、未反応ACN、未反応THA、CL、および少量部分の水を含む溶液を取り出すことを特徴とする請求項1に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/464,104 | 2003-06-17 | ||
US10/464,104 US6858728B2 (en) | 2003-06-17 | 2003-06-17 | Method for making caprolactam from impure ACN in which THA is not removed until after caprolactam is produced |
PCT/US2004/019442 WO2005000808A1 (en) | 2003-06-17 | 2004-06-17 | Method for making caprolactam from impure 6-amino-capronitrile containing tetrahydroazepine |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007520438A JP2007520438A (ja) | 2007-07-26 |
JP4961209B2 true JP4961209B2 (ja) | 2012-06-27 |
Family
ID=33517216
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006517368A Expired - Fee Related JP4961209B2 (ja) | 2003-06-17 | 2004-06-17 | テトラヒドロアゼピンを含む不純な6−アミノカプロニトリルからカプロラクタムを製造する方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US6858728B2 (ja) |
EP (1) | EP1636179B1 (ja) |
JP (1) | JP4961209B2 (ja) |
CN (1) | CN100395232C (ja) |
TW (1) | TW200519083A (ja) |
WO (1) | WO2005000808A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7214227B2 (en) * | 2004-03-22 | 2007-05-08 | Innovative Spinal Technologies | Closure member for a medical implant device |
CN109665996B (zh) * | 2017-10-17 | 2021-04-06 | 中国石油化工股份有限公司 | 己内酰胺的精制方法和装置 |
CN112827200A (zh) * | 2019-11-25 | 2021-05-25 | 南京延长反应技术研究院有限公司 | 一种己二酸氨化制备己二腈的合成系统及方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2357484A (en) * | 1941-09-12 | 1944-09-05 | Du Pont | Process for producing compounds containing an n-substituted amide group |
US2301964A (en) * | 1941-09-12 | 1942-11-17 | Du Pont | Method of preparing lactams |
US4628085A (en) * | 1985-09-03 | 1986-12-09 | Allied Corporation | Use of silica catalyst for selective production of lactams |
US5192399A (en) * | 1991-01-30 | 1993-03-09 | E. I. Du Pont De Nemours And Company | Purification of aminonitriles or diamines |
US5162567A (en) * | 1992-02-27 | 1992-11-10 | E. I. Du Pont De Nemours And Company | Purification of 6-aminocapronitrile |
DE4441962A1 (de) * | 1994-11-25 | 1996-05-30 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
DE4443125A1 (de) * | 1994-12-03 | 1996-06-05 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
DE19500041A1 (de) * | 1995-01-03 | 1996-07-04 | Basf Ag | Verfahren zur kontinuierlichen Reinigung von aus 6-Aminocapronitril hergestelltem Roh-Caprolactam |
DE19517823A1 (de) * | 1995-05-18 | 1996-11-21 | Basf Ag | Verfahren zur Herstellung von Caprolactam |
FR2735471B1 (fr) * | 1995-06-16 | 1997-08-22 | Rhone Poulenc Chimie | Procede de preparation de lactames |
DE19628805A1 (de) * | 1996-07-17 | 1998-01-22 | Basf Ag | Verfahren zur Herstellung von Caprolactam aus 6-Aminocapronitril |
FR2751962B1 (fr) * | 1996-08-02 | 1998-09-11 | Rhone Poulenc Fibres | Procede de purification de lactames |
FR2755132B1 (fr) * | 1996-10-24 | 1998-11-27 | Rhone Poulenc Fibres | Procede de traitement de lactames |
DE19704613A1 (de) * | 1997-02-07 | 1998-08-13 | Basf Ag | Verfahren zur Abtrennung von 6-Aminocapronsäurenitril aus Mischungen, die 6-Aminocapronsäurenitril und ein Imin enthalten |
FR2781480B1 (fr) * | 1998-07-22 | 2001-06-01 | Rhone Poulenc Fibres | Procede d'hydrolyse cyclisante d'un compose aminonitrile en 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 |
-
2003
- 2003-06-17 US US10/464,104 patent/US6858728B2/en not_active Expired - Fee Related
-
2004
- 2004-06-17 TW TW093117501A patent/TW200519083A/zh unknown
- 2004-06-17 JP JP2006517368A patent/JP4961209B2/ja not_active Expired - Fee Related
- 2004-06-17 EP EP04785751A patent/EP1636179B1/en not_active Expired - Fee Related
- 2004-06-17 CN CNB2004800171283A patent/CN100395232C/zh not_active Expired - Fee Related
- 2004-06-17 WO PCT/US2004/019442 patent/WO2005000808A1/en active Search and Examination
Also Published As
Publication number | Publication date |
---|---|
JP2007520438A (ja) | 2007-07-26 |
TW200519083A (en) | 2005-06-16 |
WO2005000808A1 (en) | 2005-01-06 |
CN1809533A (zh) | 2006-07-26 |
EP1636179A1 (en) | 2006-03-22 |
CN100395232C (zh) | 2008-06-18 |
US6858728B2 (en) | 2005-02-22 |
EP1636179B1 (en) | 2012-01-04 |
US20040260087A1 (en) | 2004-12-23 |
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