SK84097A3 - Process for continuously cleaning raw caprolactam made from 6-amino capronitrile - Google Patents

Process for continuously cleaning raw caprolactam made from 6-amino capronitrile Download PDF

Info

Publication number: SK84097A3
Authority: SK; Slovakia
Prior art keywords: caprolactam; mixture; range; solvent; water
Prior art date: 1995-01-03

Application number

SK840-97A

Other languages

English (en)

Slovak (sk)

Inventor

Josef Ritz

Rolf Fischer

Werner Schnurr

Gunther Achhammer

Hermann Luyken

Eberhard Fuchs

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1995-01-03

Filing date

1995-12-22

Publication date

1998-05-06

1995-12-22 Application filed by Basf Ag filed Critical Basf Ag

1998-05-06 Publication of SK84097A3 publication Critical patent/SK84097A3/sk

Links

JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 180
KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 title claims abstract description 34
238000000034 method Methods 0.000 title claims description 20
238000004140 cleaning Methods 0.000 title abstract 2
239000000203 mixture Substances 0.000 claims abstract description 39
239000003054 catalyst Substances 0.000 claims abstract description 36
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
229910001868 water Inorganic materials 0.000 claims abstract description 32
239000002904 solvent Substances 0.000 claims abstract description 29
238000004821 distillation Methods 0.000 claims abstract description 28
238000009835 boiling Methods 0.000 claims abstract description 17
238000006243 chemical reaction Methods 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 16
238000000746 purification Methods 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 9
230000036571 hydration Effects 0.000 abstract 2
238000006703 hydration reaction Methods 0.000 abstract 2
235000011149 sulphuric acid Nutrition 0.000 abstract 2
239000001117 sulphuric acid Substances 0.000 abstract 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 19
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 18
150000002500 ions Chemical class 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000002585 base Substances 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000012071 phase Substances 0.000 description 11
239000007791 liquid phase Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004448 titration Methods 0.000 description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
229910052759 nickel Inorganic materials 0.000 description 8
239000004408 titanium dioxide Substances 0.000 description 8
229910021529 ammonia Inorganic materials 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000006237 Beckmann rearrangement reaction Methods 0.000 description 5
229910017052 cobalt Inorganic materials 0.000 description 5
239000010941 cobalt Substances 0.000 description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000012535 impurity Substances 0.000 description 5
150000003951 lactams Chemical class 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
230000008033 biological extinction Effects 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
229910052742 iron Inorganic materials 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000012286 potassium permanganate Substances 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
230000000737 periodic effect Effects 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
229910052707 ruthenium Inorganic materials 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
239000011787 zinc oxide Substances 0.000 description 3
GWCFTYITFDWLAY-UHFFFAOYSA-N 1-ethylazepan-2-one Chemical compound CCN1CCCCCC1=O GWCFTYITFDWLAY-UHFFFAOYSA-N 0.000 description 2
FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-UHFFFAOYSA-N 0.000 description 2
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
229960002684 aminocaproic acid Drugs 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
-1 cyclic nitriles Chemical class 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
239000011552 falling film Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000002638 heterogeneous catalyst Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
229910001928 zirconium oxide Inorganic materials 0.000 description 2
BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
SKJCKYVIQGBWTN-UHFFFAOYSA-N (4-hydroxyphenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(O)C=C1 SKJCKYVIQGBWTN-UHFFFAOYSA-N 0.000 description 1
PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001192924 Parna Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
239000005083 Zinc sulfide Substances 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
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 1
150000007513 acids Chemical class 0.000 description 1
229910052768 actinide Inorganic materials 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 description 1
229910000149 boron phosphate Inorganic materials 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
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 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
229910000423 chromium oxide Inorganic materials 0.000 description 1
DBULDCSVZCUQIR-UHFFFAOYSA-N chromium(3+);trisulfide Chemical compound [S-2].[S-2].[S-2].[Cr+3].[Cr+3] DBULDCSVZCUQIR-UHFFFAOYSA-N 0.000 description 1
RYTYSMSQNNBZDP-UHFFFAOYSA-N cobalt copper Chemical compound [Co].[Cu] RYTYSMSQNNBZDP-UHFFFAOYSA-N 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
RPYFZMPJOHSVLD-UHFFFAOYSA-N copper vanadium Chemical compound [V][V][Cu] RPYFZMPJOHSVLD-UHFFFAOYSA-N 0.000 description 1
230000001351 cycling effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229910052747 lanthanoid Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
239000011133 lead Substances 0.000 description 1
150000002611 lead compounds Chemical class 0.000 description 1
238000011068 loading method Methods 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
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910000484 niobium oxide Inorganic materials 0.000 description 1
URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
238000006146 oximation reaction Methods 0.000 description 1
150000002923 oximes 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
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
MMKQUGHLEMYQSG-UHFFFAOYSA-N oxygen(2-);praseodymium(3+) Chemical compound [O-2].[O-2].[O-2].[Pr+3].[Pr+3] MMKQUGHLEMYQSG-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000012466 permeate Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
229910003447 praseodymium oxide Inorganic materials 0.000 description 1
RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229910001954 samarium oxide Inorganic materials 0.000 description 1
229940075630 samarium oxide Drugs 0.000 description 1
FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003346 selenoethers Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229910052566 spinel group Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
150000004763 sulfides Chemical class 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000004772 tellurides Chemical class 0.000 description 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 description 1
229910003452 thorium oxide Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052984 zinc sulfide Inorganic materials 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1
IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 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
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Polyamides (AREA)

SK840-97A 1995-01-03 1995-12-22 Process for continuously cleaning raw caprolactam made from 6-amino capronitrile SK84097A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19500041A DE19500041A1 (de)	1995-01-03	1995-01-03	Verfahren zur kontinuierlichen Reinigung von aus 6-Aminocapronitril hergestelltem Roh-Caprolactam
PCT/EP1995/005103 WO1996020923A1 (de)	1995-01-03	1995-12-22	Verfahren zur kontinuierlichen reinigung von aus 6-aminocapronitril hergestelltem roh-caprolactam

Publications (1)

Publication Number	Publication Date
SK84097A3 true SK84097A3 (en)	1998-05-06

Family

ID=7750939

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK840-97A SK84097A3 (en)	1995-01-03	1995-12-22	Process for continuously cleaning raw caprolactam made from 6-amino capronitrile

Country Status (18)

Country	Link
US (1)	US5496941A (pt)
EP (1)	EP0801643B1 (pt)
JP (1)	JPH10511668A (pt)
KR (1)	KR100388869B1 (pt)
CN (1)	CN1068311C (pt)
AU (1)	AU4389396A (pt)
BG (1)	BG63387B1 (pt)
BR (1)	BR9510187A (pt)
CA (1)	CA2209336C (pt)
CZ (1)	CZ288217B6 (pt)
DE (2)	DE19500041A1 (pt)
ES (1)	ES2160729T3 (pt)
MY (1)	MY113742A (pt)
PL (1)	PL186443B1 (pt)
RU (1)	RU2159234C2 (pt)
SK (1)	SK84097A3 (pt)
TW (1)	TW283705B (pt)
WO (1)	WO1996020923A1 (pt)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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
US5877314A (en) *	1997-02-14	1999-03-02	Dsm N.V.	Process to continuously prepare an aqueous mixture of episilon caprolactum and episilon caprolactum precursors
EP0943608A1 (en) *	1998-03-20	1999-09-22	Dsm N.V.	Process for the continuous purification of crude epsilon--caprolactam
FR2781796B1 (fr) †	1998-07-28	2000-09-22	Rhone Poulenc Fibres	Procede de deshydratation de lactame
FR2786180B1 (fr) *	1998-11-19	2001-11-23	Rhone Poulenc Fibres	Procede de traitement de lactames et procede de purification d'un lactame
DE10080450T1 (de) *	1999-02-10	2001-05-17	Toshiba Kawasaki Kk	Kohlenmonoxidumwandlungsvorrichtung für eine Brennstoffzelle und Brennstoffzellen-Energiegewinnungssystem
DE19910504A1 (de)	1999-03-10	2000-09-14	Basf Ag	Verfahren zur Reinigung von N-substituierten Lactamen
FR2803296B1 (fr) *	1999-12-30	2002-02-15	Rhodia Polyamide Intermediates	Procede de purification de lactames
DE10021192A1 (de)	2000-05-03	2001-11-08	Basf Ag	Verfahren zur Herstellung von Caprolactam
DE10021191A1 (de)	2000-05-03	2001-11-08	Basf Ag	Verfahren zur Herstellung eines Polymers unter Verwendung von Caprolactam
DE10021199A1 (de) *	2000-05-03	2001-11-08	Basf Ag	Verfahren zur Herstellung von Caprolactam
FR2809395B1 (fr) *	2000-05-26	2002-07-19	Rhodia Polyamide Intermediates	Procede de purification de lactames
JP4182273B2 (ja) *	2000-06-27	2008-11-19	住友化学株式会社	ε−カプロラクタムの製造方法
DE10033518A1 (de) *	2000-07-11	2002-01-24	Basf Ag	Verfahren zur Abtrennung von Ammoniak
EP1423369B1 (en)	2001-08-27	2013-07-17	DSM IP Assets B.V.	Process for distilling alkaline caprolactam product at reduced pressure
US7022844B2 (en)	2002-09-21	2006-04-04	Honeywell International Inc.	Amide-based compounds, production, recovery, purification and uses thereof
DE10253094A1 (de)	2002-11-13	2004-05-27	Basf Ag	Verfahren zur Reinigung von Caprolactam
DE10253095A1 (de) *	2002-11-13	2004-06-17	Basf Ag	Verfahren zur Reinigung von Caprolactam
US6858728B2 (en) *	2003-06-17	2005-02-22	Invista North America S.A.R.L.	Method for making caprolactam from impure ACN in which THA is not removed until after caprolactam is produced
US7390897B2 (en) *	2005-03-18	2008-06-24	Invista North America S.A.R.L.	Method for making caprolactam from impure 6-aminocapronitrile
WO2007099029A2 (de) *	2006-02-24	2007-09-07	Basf Aktiengesellschaft	Verfahren zur reinigung von caprolactam, hergestellt aus lysin
JP5708637B2 (ja)	2010-03-15	2015-04-30	宇部興産株式会社	アミド化合物の製造方法
EP2572109B1 (en) *	2010-05-21	2020-09-02	Exxonmobil Upstream Research Company	Parallel dynamic compressor apparatus and method related thereto
US20130150591A1 (en) *	2011-12-07	2013-06-13	Rolf Pinkos	Method for purifying n-alkyl-substituted pyrrolidones by hydrogenation
TWI520944B (zh)	2015-02-13	2016-02-11	中國石油化學工業開發股份有限公司	己內醯胺之製造方法及其系統
CN111153825A (zh) *	2019-06-19	2020-05-15	浙江大学	利用负载型金属氧化物催化材料制备酰胺类化合物的方法
CN111122720B (zh) *	2019-12-11	2022-09-02	湖北三宁碳磷基新材料产业技术研究院有限公司	己内酰胺、6-氨基己酰胺和6-氨基己腈的分析方法
CN111635330B (zh) *	2020-06-24	2023-01-24	江苏扬农化工集团有限公司	一种己二胺关键中间体反应残渣回收利用并联产羧酸的方法
CN114210361A (zh) *	2021-12-27	2022-03-22	于向真	一种从环己酮肟或己内酰胺一步合成6－氨基己腈的催化剂及其制备方法

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2692878A (en) *		1954-10-26		Method forithe continuous produc-
US2786052A (en) *		1957-03-19		Process of purifying caprolactam
US2828307A (en) *		1958-03-25		Karl h
DD75083A (pt) *
US3145198A (en) *		1964-08-18		piija
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
GB560100A (en) *	1941-09-12	1944-03-20	Ici Ltd	Improvements in or relating to the manufacture of n-substituted amides
JPS4821958B1 (pt) *	1969-01-28	1973-07-02
DE2926279A1 (de) *	1979-06-29	1981-01-08	Basf Ag	Verfahren zur reinigung von caprolactam
EP0150295A3 (en) *	1983-12-19	1988-03-30	Allied Corporation	Selective production of n-substituted amides by use of cu(o)/metallic oxides catalyst compositions
DE3735054A1 (de) *	1987-10-16	1989-04-27	Basf Ag	Verfahren zur gewinnung von caprolactam aus leichtsiedern oder schwersiedern der caprolactamdestillation oder gemischen derselben
DE3925575A1 (de) *	1989-08-02	1991-02-07	Basf Ag	Verfahren zur kontinuierlichen reinigung von caprolactam
DE4319134A1 (de) *	1993-06-09	1994-12-15	Basf Ag	Verfahren zur Herstellung von Caprolactam
DE4339648A1 (de) *	1993-11-20	1995-05-24	Basf Ag	Verfahren zur Herstellung von Caprolactam
FR2714379B1 (fr) *	1993-12-23	1996-02-02	Rhone Poulenc Chimie	Procédé de préparation de lactame.
DE4441962A1 (de) *	1994-11-25	1996-05-30	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

1995
- 1995-01-03 DE DE19500041A patent/DE19500041A1/de not_active Withdrawn
- 1995-01-18 US US08/375,410 patent/US5496941A/en not_active Expired - Fee Related
- 1995-02-09 TW TW084101076A patent/TW283705B/zh active
- 1995-12-22 WO PCT/EP1995/005103 patent/WO1996020923A1/de not_active Ceased
- 1995-12-22 CN CN95197241A patent/CN1068311C/zh not_active Expired - Fee Related
- 1995-12-22 KR KR1019970704568A patent/KR100388869B1/ko not_active Expired - Fee Related
- 1995-12-22 PL PL95321162A patent/PL186443B1/pl not_active IP Right Cessation
- 1995-12-22 JP JP8520713A patent/JPH10511668A/ja not_active Ceased
- 1995-12-22 AU AU43893/96A patent/AU4389396A/en not_active Abandoned
- 1995-12-22 BR BR9510187A patent/BR9510187A/pt not_active IP Right Cessation
- 1995-12-22 CA CA002209336A patent/CA2209336C/en not_active Expired - Fee Related
- 1995-12-22 DE DE59509451T patent/DE59509451D1/de not_active Expired - Fee Related
- 1995-12-22 SK SK840-97A patent/SK84097A3/sk unknown
- 1995-12-22 ES ES95942729T patent/ES2160729T3/es not_active Expired - Lifetime
- 1995-12-22 EP EP95942729A patent/EP0801643B1/de not_active Expired - Lifetime
- 1995-12-22 CZ CZ19971972A patent/CZ288217B6/cs not_active IP Right Cessation
- 1995-12-22 RU RU97113722/04A patent/RU2159234C2/ru not_active IP Right Cessation
- 1995-12-26 MY MYPI95004086A patent/MY113742A/en unknown
1997
- 1997-06-25 BG BG101672A patent/BG63387B1/bg unknown

Also Published As

Publication number	Publication date
BR9510187A (pt)	1997-12-23
KR100388869B1 (ko)	2003-10-04
CN1068311C (zh)	2001-07-11
DE59509451D1 (de)	2001-08-30
BG63387B1 (bg)	2001-12-29
EP0801643B1 (de)	2001-07-25
KR980700966A (ko)	1998-04-30
CN1171781A (zh)	1998-01-28
RU2159234C2 (ru)	2000-11-20
AU4389396A (en)	1996-07-24
CZ288217B6 (en)	2001-05-16
CA2209336C (en)	2004-02-24
MY113742A (en)	2002-05-31
CA2209336A1 (en)	1996-07-11
MX9704864A (es)	1997-10-31
CZ197297A3 (cs)	1998-03-18
EP0801643A1 (de)	1997-10-22
US5496941A (en)	1996-03-05
BG101672A (en)	1998-02-27
JPH10511668A (ja)	1998-11-10
PL321162A1 (en)	1997-11-24
ES2160729T3 (es)	2001-11-16
PL186443B1 (pl)	2004-01-30
TW283705B (pt)	1996-08-21
WO1996020923A1 (de)	1996-07-11
DE19500041A1 (de)	1996-07-04

Publication	Publication Date	Title
SK84097A3 (en)	1998-05-06	Process for continuously cleaning raw caprolactam made from 6-amino capronitrile
EP0876341B1 (de)	2000-08-09	Verfahren zur gleichzeitigen herstellung von caprolactam und hexamethylendiamin
EP0912508B2 (de)	2005-12-07	Verfahren zur herstellung von caprolactam aus 6-aminocapronitril
KR100386706B1 (ko)	2003-08-21	카프로락탐및헥사메틸렌디아민의동시제조방법
RU2154058C2 (ru)	2000-08-10	Способ получения капролактама
US6677449B2 (en)	2004-01-13	Preparation of caprolactam
US5502185A (en)	1996-03-26	Preparation of lactams
US7501047B2 (en)	2009-03-10	Method for purifying caprolactam
US7217818B2 (en)	2007-05-15	Purification of caprolactam
KR100447767B1 (ko)	2005-01-15	ε-카프로락탐의정제방법
MXPA97004864A (en)	1998-07-03	Process for the continuous purification of capillactama impura prepared from 6-amicapronitr
CA2194189C (en)	2005-11-29	Process for producing cyclic lactames