CZ2007622A3 - Zpusob výroby kaprolaktamu - Google Patents
Zpusob výroby kaprolaktamu Download PDFInfo
- Publication number
- CZ2007622A3 CZ2007622A3 CZ20070622A CZ2007622A CZ2007622A3 CZ 2007622 A3 CZ2007622 A3 CZ 2007622A3 CZ 20070622 A CZ20070622 A CZ 20070622A CZ 2007622 A CZ2007622 A CZ 2007622A CZ 2007622 A3 CZ2007622 A3 CZ 2007622A3
- Authority
- CZ
- Czechia
- Prior art keywords
- reaction zone
- reaction
- aminocapronitrile
- final
- water
- Prior art date
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 128
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 170
- KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 claims abstract description 102
- 238000001816 cooling Methods 0.000 claims abstract description 28
- 238000004821 distillation Methods 0.000 claims abstract description 27
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 23
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 21
- 239000012808 vapor phase Substances 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 79
- 239000003054 catalyst Substances 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 40
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 26
- 230000008569 process Effects 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000007848 Bronsted acid Substances 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- SCHOATXEWOOTHN-UHFFFAOYSA-N 3-aminohexanenitrile Chemical compound CCCC(N)CC#N SCHOATXEWOOTHN-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract description 10
- 150000003951 lactams Chemical class 0.000 abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011973 solid acid Substances 0.000 description 5
- 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 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000013529 heat transfer fluid Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- -1 lactam sulfate Chemical class 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- YIJFIIXHVSHQEN-UHFFFAOYSA-N 3-Aminocaproic acid Chemical compound CCCC(N)CC(O)=O YIJFIIXHVSHQEN-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000013404 process transfer Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002699 waste material 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
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cable Accessories (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
- Sealing Battery Cases Or Jackets (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/083,728 US7060820B1 (en) | 2005-03-18 | 2005-03-18 | Process for making caprolactam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ2007622A3 true CZ2007622A3 (cs) | 2008-07-02 |
Family
ID=36576434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20070622A CZ2007622A3 (cs) | 2005-03-18 | 2006-03-15 | Zpusob výroby kaprolaktamu |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7060820B1 (enExample) |
| EP (1) | EP1858843B1 (enExample) |
| JP (1) | JP5302672B2 (enExample) |
| KR (1) | KR101141912B1 (enExample) |
| CN (1) | CN101142179B (enExample) |
| AT (1) | ATE452878T1 (enExample) |
| BR (1) | BRPI0609846A2 (enExample) |
| CA (1) | CA2600770A1 (enExample) |
| CZ (1) | CZ2007622A3 (enExample) |
| DE (1) | DE602006011286D1 (enExample) |
| MX (1) | MX2007011228A (enExample) |
| MY (1) | MY142413A (enExample) |
| PL (1) | PL383762A1 (enExample) |
| SK (1) | SK51082007A3 (enExample) |
| TW (1) | TW200643010A (enExample) |
| WO (1) | WO2006101871A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8167490B2 (en) | 2009-04-22 | 2012-05-01 | Reynolds Consumer Products Inc. | Multilayer stretchy drawstring |
| FR2944791B1 (fr) | 2009-04-27 | 2012-02-10 | Rhodia Operations | Procede de preparation de lactames. |
| CN102952075A (zh) * | 2011-08-30 | 2013-03-06 | 中国科学院大连化学物理研究所 | 一种己内酰胺的合成方法 |
| CN102399363B (zh) * | 2011-10-11 | 2013-11-06 | 上海焦耳蜡业有限公司 | 一种利用回收尼龙生产热熔胶的方法 |
| CN113087641B (zh) * | 2021-04-14 | 2023-10-24 | 江苏扬农化工集团有限公司 | 一种由环己酮肟制备6-氨基己腈的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2301964A (en) | 1941-09-12 | 1942-11-17 | Du Pont | Method of preparing lactams |
| US2357484A (en) | 1941-09-12 | 1944-09-05 | Du Pont | Process for producing compounds containing an n-substituted amide group |
| US4625023A (en) * | 1985-09-03 | 1986-11-25 | Allied Corporation | Selective conversion of aliphatic and aromatic aminonitriles and/or dinitriles into lactams |
| 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 |
| DE19753301A1 (de) | 1997-12-01 | 1999-06-02 | Basf Ag | Verfahren zur Herstellung von Lactamen |
| FR2781393B1 (fr) * | 1998-07-22 | 2000-08-25 | Rhone Poulenc Fibres | Procede de regeneration d'un catalyseur d'hydrolyse cyclisante d'un aminonitrile en lactame et utilisation du catalyseur regenere pour la fabrication de lactames |
| US6686465B2 (en) * | 2000-05-03 | 2004-02-03 | Basf Aktiengesellschaft | Preparation of cyclic lactams |
| JP2004298768A (ja) * | 2003-03-31 | 2004-10-28 | Jgc Corp | 気相反応装置の運転方法 |
| US6716977B1 (en) * | 2003-06-17 | 2004-04-06 | E. I. Du Pont De Nemours And Company | Method for making caprolactam from impure ACN wherein ammonia and water are removed from crude caprolactam in a simple separation step and then THA is removed from the resulting caprolactam melt |
-
2005
- 2005-03-18 US US11/083,728 patent/US7060820B1/en not_active Expired - Fee Related
-
2006
- 2006-03-15 MX MX2007011228A patent/MX2007011228A/es active IP Right Grant
- 2006-03-15 CN CN2006800087225A patent/CN101142179B/zh not_active Expired - Fee Related
- 2006-03-15 WO PCT/US2006/009232 patent/WO2006101871A1/en not_active Ceased
- 2006-03-15 CA CA002600770A patent/CA2600770A1/en not_active Abandoned
- 2006-03-15 PL PL383762A patent/PL383762A1/pl unknown
- 2006-03-15 BR BRPI0609846-0A patent/BRPI0609846A2/pt not_active IP Right Cessation
- 2006-03-15 DE DE602006011286T patent/DE602006011286D1/de active Active
- 2006-03-15 CZ CZ20070622A patent/CZ2007622A3/cs unknown
- 2006-03-15 KR KR1020077021278A patent/KR101141912B1/ko not_active Expired - Fee Related
- 2006-03-15 EP EP06738306A patent/EP1858843B1/en not_active Not-in-force
- 2006-03-15 SK SK5108-2007A patent/SK51082007A3/sk unknown
- 2006-03-15 AT AT06738306T patent/ATE452878T1/de not_active IP Right Cessation
- 2006-03-15 JP JP2008501986A patent/JP5302672B2/ja not_active Expired - Fee Related
- 2006-03-17 TW TW095109264A patent/TW200643010A/zh unknown
- 2006-03-17 MY MYPI20061186A patent/MY142413A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7060820B1 (en) | 2006-06-13 |
| PL383762A1 (pl) | 2008-05-12 |
| JP5302672B2 (ja) | 2013-10-02 |
| SK51082007A3 (sk) | 2008-10-07 |
| EP1858843A1 (en) | 2007-11-28 |
| MX2007011228A (es) | 2007-10-17 |
| BRPI0609846A2 (pt) | 2010-05-04 |
| MY142413A (en) | 2010-11-30 |
| CA2600770A1 (en) | 2006-09-28 |
| DE602006011286D1 (de) | 2010-02-04 |
| JP2008533160A (ja) | 2008-08-21 |
| ATE452878T1 (de) | 2010-01-15 |
| CN101142179B (zh) | 2012-05-30 |
| TW200643010A (en) | 2006-12-16 |
| KR101141912B1 (ko) | 2012-05-03 |
| CN101142179A (zh) | 2008-03-12 |
| KR20080016530A (ko) | 2008-02-21 |
| WO2006101871A1 (en) | 2006-09-28 |
| EP1858843B1 (en) | 2009-12-23 |
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