BG63431B1 - Метод за едновременно получаване на капролактам ихексаметилендиамин - Google Patents

Метод за едновременно получаване на капролактам ихексаметилендиамин Download PDF

Info

Publication number: BG63431B1
Authority: BG; Bulgaria
Prior art keywords: column; distillation; range; adiponitrile; ammonia
Prior art date: 1995-01-05

Application number

BG101661A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG101661A (en

Inventor

Guenther Achhammer

Peter Bassler

Rolf Fischer

Eberhard Fuchs

Hermann Luyken

Werner Schnurr

Tom Witzel

Original Assignee

Basf Aktiengesellschaft

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.)

1995-01-05

Filing date

1997-06-24

Publication date

2002-01-31

1997-06-24 Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft

1998-02-27 Publication of BG101661A publication Critical patent/BG101661A/xx

2002-01-31 Publication of BG63431B1 publication Critical patent/BG63431B1/bg

Links

NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims abstract description 135
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 70
238000000034 method Methods 0.000 title claims description 42
238000004821 distillation Methods 0.000 claims abstract description 150
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 140
KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 claims abstract description 92
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims abstract description 77
229910021529 ammonia Inorganic materials 0.000 claims abstract description 70
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims abstract description 53
239000000203 mixture Substances 0.000 claims abstract description 52
150000001875 compounds Chemical class 0.000 claims abstract description 51
229940126062 Compound A Drugs 0.000 claims abstract description 34
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 34
238000002360 preparation method Methods 0.000 claims abstract description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
238000009835 boiling Methods 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 5
WDWDWGRYHDPSDS-UHFFFAOYSA-N methanimine Chemical compound N=C WDWDWGRYHDPSDS-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 description 60
239000000047 product Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 24
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229910001868 water Inorganic materials 0.000 description 24
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
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238000005984 hydrogenation reaction Methods 0.000 description 16
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239000010948 rhodium Substances 0.000 description 13
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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229910052759 nickel Inorganic materials 0.000 description 11
239000004408 titanium dioxide Substances 0.000 description 11
-1 6-aminocaproic acid nitrile Chemical class 0.000 description 10
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239000010941 cobalt Substances 0.000 description 10
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 10
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 10
238000007363 ring formation reaction Methods 0.000 description 10
229910052707 ruthenium Inorganic materials 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
230000003993 interaction Effects 0.000 description 9
239000000377 silicon dioxide Substances 0.000 description 9
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AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 6
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 6
239000000395 magnesium oxide Substances 0.000 description 6
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239000000969 carrier Substances 0.000 description 5
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239000010949 copper Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
239000002243 precursor Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000002823 nitrates Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
230000000737 periodic effect Effects 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
230000004913 activation Effects 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001342 alkaline earth metals Chemical class 0.000 description 3
229960002684 aminocaproic acid Drugs 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
150000004675 formic acid derivatives Chemical class 0.000 description 3
230000002262 irrigation Effects 0.000 description 3
238000003973 irrigation Methods 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
239000011133 lead Substances 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
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 3
150000002739 metals Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 3
150000003467 sulfuric acid derivatives Chemical class 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
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
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150000007513 acids Chemical class 0.000 description 2
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229910052782 aluminium Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001354 calcination Methods 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 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
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
238000010924 continuous production Methods 0.000 description 2
150000001924 cycloalkanes Chemical class 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
NJNQDCIAOXIFTB-UHFFFAOYSA-N ethyl 6-aminohexanoate Chemical compound CCOC(=O)CCCCCN NJNQDCIAOXIFTB-UHFFFAOYSA-N 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
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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
150000004679 hydroxides Chemical class 0.000 description 2
229910052741 iridium Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
150000002642 lithium compounds Chemical class 0.000 description 2
238000011068 loading method Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052750 molybdenum Inorganic materials 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
229910000480 nickel oxide Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 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
229910052762 osmium Inorganic materials 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
229910052698 phosphorus Inorganic materials 0.000 description 2
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238000001556 precipitation Methods 0.000 description 2
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239000011029 spinel Substances 0.000 description 2
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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
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229910000310 actinide oxide Inorganic materials 0.000 description 1
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229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
229910052810 boron oxide Inorganic materials 0.000 description 1
244000309464 bull Species 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 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
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
229910000420 cerium oxide Inorganic materials 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
DBULDCSVZCUQIR-UHFFFAOYSA-N chromium(3+);trisulfide Chemical class [S-2].[S-2].[S-2].[Cr+3].[Cr+3] DBULDCSVZCUQIR-UHFFFAOYSA-N 0.000 description 1
229910000428 cobalt oxide Inorganic materials 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
RPYFZMPJOHSVLD-UHFFFAOYSA-N copper vanadium Chemical compound [V][V][Cu] RPYFZMPJOHSVLD-UHFFFAOYSA-N 0.000 description 1
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
239000004914 cyclooctane Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
FZFYOUJTOSBFPQ-UHFFFAOYSA-M dipotassium;hydroxide Chemical compound [OH-].[K+].[K+] FZFYOUJTOSBFPQ-UHFFFAOYSA-M 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
229910000311 lanthanide oxide Inorganic materials 0.000 description 1
150000002602 lanthanoids Chemical class 0.000 description 1
150000002611 lead compounds Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium 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
239000011733 molybdenum Substances 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
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
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
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 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
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 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
238000002161 passivation Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
229910003447 praseodymium oxide Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
238000004064 recycling 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
MFIWAIVSOUGHLI-UHFFFAOYSA-N selenium;tin Chemical compound [Sn]=[Se] MFIWAIVSOUGHLI-UHFFFAOYSA-N 0.000 description 1
150000003346 selenoethers Chemical class 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052566 spinel group Inorganic materials 0.000 description 1
150000004763 sulfides Chemical class 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
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
239000010937 tungsten Substances 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
229910052726 zirconium Inorganic materials 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Polyamides (AREA)

BG101661A 1995-01-05 1997-06-24 Метод за едновременно получаване на капролактам ихексаметилендиамин BG63431B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19500222A DE19500222A1 (de)	1995-01-05	1995-01-05	Verfahren zur gleichzeitigen Herstellung von Caprolactam und Hexamethylendiamin
PCT/EP1995/005115 WO1996020931A1 (de)	1995-01-05	1995-12-22	Verfahren zur gleichzeitigen herstellung von caprolactam und hexamethylendiamin

Publications (2)

Publication Number	Publication Date
BG101661A BG101661A (en)	1998-02-27
BG63431B1 true BG63431B1 (bg)	2002-01-31

Family

ID=7751046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG101661A BG63431B1 (bg)	1995-01-05	1997-06-24	Метод за едновременно получаване на капролактам ихексаметилендиамин

Country Status (18)

Country	Link
EP (1)	EP0801647B1 (cs)
JP (1)	JP3708549B2 (cs)
KR (1)	KR100386706B1 (cs)
CN (1)	CN1064353C (cs)
AT (1)	ATE242217T1 (cs)
AU (1)	AU4347396A (cs)
BG (1)	BG63431B1 (cs)
BR (1)	BR9510133A (cs)
CZ (1)	CZ289886B6 (cs)
DE (2)	DE19500222A1 (cs)
ES (1)	ES2201127T3 (cs)
FI (1)	FI972839A7 (cs)
MY (1)	MY112196A (cs)
PL (1)	PL187887B1 (cs)
RU (1)	RU2153493C2 (cs)
SK (1)	SK84297A3 (cs)
TW (1)	TW340839B (cs)
WO (1)	WO1996020931A1 (cs)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19636765A1 (de) *	1996-09-10	1998-03-12	Basf Ag	Verfahren zur gleichzeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin
DE19636766A1 (de)	1996-09-10	1998-03-12	Basf Ag	Verfahren zur gleichzeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin
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
DE19704620A1 (de)	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Abtrennung von 6-Aminocapronitril aus Mischungen, die 6-Aminocapronitril und ein Imin enthalten
DE19704612A1 (de) *	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Gewinnung von Hexamethylendiamin aus Hexamethylendiamin enthaltenden Mischungen
DE19704616A1 (de) *	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Abtrennung von 2-Aminomethylcyclopentylamin aus einer Mischung enthaltend Hexamethylendiamin und 2-Aminomethylcyclopentylamin
DE19704614A1 (de)	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Abtrennnung eines Imins aus einer Mischung enthaltend ein Amin und ein Imin
DE19812427A1 (de) *	1998-03-20	1999-09-23	Basf Ag	Verfahren zur Abtrennung eines Azepin-Derivats aus einer Mischung enthaltend ein Amin und ein Azepin-Derivat
DE19842905A1 (de)	1998-09-18	2000-03-23	Basf Ag	Verfahren zur gleichzeitigen Herstellung eines cyclischen Lactams und eines cyclischen Amins
DE10010825A1 (de) *	2000-03-08	2001-09-13	Basf Ag	Verfahren zur Abtrennung eines Azepin-Derivats aus einer Mischung enthaltend ein Amin und ein Azepin-Derivat
MY127068A (en) *	2000-06-05	2006-11-30	Basf Ag	Removal of ammonia from solutions including caprolactam and ammonia
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
DE10223827A1 (de)	2002-05-28	2003-12-11	Basf Ag	Verfahren zur Reduzierung des Gehalts an einem ungesättigten Amin in einer Mischung enthaltend ein Aminonitril, ein Diamin, ein Dinitril oder deren Gemische
US7208632B2 (en) *	2004-09-10	2007-04-24	Invista North America S.A R.L.	Separation of 6-aminocapronitrile and hexamethylenediamine from a mixture comprising hexamethylenediamine, 6-aminocapronitrile and tetrahydroazepine
FR2892118B1 (fr)	2005-10-18	2010-12-10	Rhodia Recherches & Tech	Procede de fabrication d'hexamethylene diamine et d'aminocapronitrile.
FR2902425B1 (fr) *	2006-06-20	2008-07-18	Rhodia Recherches & Tech	Procede de fabrication de diamines primaires
CN112876381B (zh) *	2021-04-14	2024-01-26	江苏扬农化工集团有限公司	一种气相法制备6-氨基己腈的模拟移动床装置及方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2301964A (en) *	1941-09-12	1942-11-17	Du Pont	Method of preparing lactams
DE954416C (de) *	1952-11-04	1956-12-20	Basf Ag	Verfahren zur Herstellung von Aminonitrilen und Diaminen
GB1179706A (en) *	1966-07-22	1970-01-28	Ici Ltd	Organic Amines
DE2606364C3 (de) *	1976-02-18	1988-05-26	Basf Ag, 6700 Ludwigshafen	Verfahren zur Stofftrennung aus einem flüssigen Gemisch durch fraktionierte Kristallisation
US4628085A (en) *	1985-09-03	1986-12-09	Allied Corporation	Use of silica catalyst for selective production of lactams

1995
- 1995-01-05 DE DE19500222A patent/DE19500222A1/de not_active Withdrawn
- 1995-02-09 TW TW084101079A patent/TW340839B/zh active
- 1995-12-20 MY MYPI95003990A patent/MY112196A/en unknown
- 1995-12-22 EP EP95942198A patent/EP0801647B1/de not_active Expired - Lifetime
- 1995-12-22 AT AT95942198T patent/ATE242217T1/de not_active IP Right Cessation
- 1995-12-22 PL PL32126795A patent/PL187887B1/pl not_active IP Right Cessation
- 1995-12-22 CN CN95197256A patent/CN1064353C/zh not_active Expired - Fee Related
- 1995-12-22 JP JP52005596A patent/JP3708549B2/ja not_active Expired - Fee Related
- 1995-12-22 ES ES95942198T patent/ES2201127T3/es not_active Expired - Lifetime
- 1995-12-22 KR KR1019970704616A patent/KR100386706B1/ko not_active Expired - Fee Related
- 1995-12-22 BR BR9510133A patent/BR9510133A/pt not_active IP Right Cessation
- 1995-12-22 WO PCT/EP1995/005115 patent/WO1996020931A1/de not_active Ceased
- 1995-12-22 RU RU97113741/04A patent/RU2153493C2/ru not_active IP Right Cessation
- 1995-12-22 AU AU43473/96A patent/AU4347396A/en not_active Abandoned
- 1995-12-22 SK SK842-97A patent/SK84297A3/sk unknown
- 1995-12-22 CZ CZ19972027A patent/CZ289886B6/cs not_active IP Right Cessation
- 1995-12-22 DE DE59510717T patent/DE59510717D1/de not_active Expired - Fee Related
1997
- 1997-06-24 BG BG101661A patent/BG63431B1/bg unknown
- 1997-07-02 FI FI972839A patent/FI972839A7/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
CZ202797A3 (cs)	1998-02-18
BG101661A (en)	1998-02-27
CZ289886B6 (cs)	2002-04-17
JPH10511361A (ja)	1998-11-04
EP0801647B1 (de)	2003-06-04
JP3708549B2 (ja)	2005-10-19
EP0801647A1 (de)	1997-10-22
KR100386706B1 (ko)	2003-08-21
MX9704863A (es)	1997-10-31
ES2201127T3 (es)	2004-03-16
AU4347396A (en)	1996-07-24
RU2153493C2 (ru)	2000-07-27
FI972839A0 (fi)	1997-07-02
KR19980701227A (ko)	1998-05-15
CN1064353C (zh)	2001-04-11
DE19500222A1 (de)	1996-07-11
ATE242217T1 (de)	2003-06-15
PL187887B1 (pl)	2004-10-29
DE59510717D1 (de)	2003-07-10
CN1171782A (zh)	1998-01-28
MY112196A (en)	2001-04-30
FI972839A7 (fi)	1997-07-02
SK84297A3 (en)	1998-03-04
TW340839B (en)	1998-09-21
BR9510133A (pt)	1997-12-30
PL321267A1 (en)	1997-11-24
WO1996020931A1 (de)	1996-07-11

Publication	Publication Date	Title
US6147208A (en)	2000-11-14	Process for simultaneously preparing caprolactam and hexamethylene diamine
KR100388869B1 (ko)	2003-10-04	6-아미노카프로니트릴로부터제조된조카프롤락탐의연속정제방법
CA2342177C (en)	2008-12-23	Improved method for simultaneous preparation of 6-aminocapronitrile and hexamethylene diamine
US5371292A (en)	1994-12-06	Preparation of 3-aminomethyl-3,5,5-trimethyl-cyclohexylamine
KR100386706B1 (ko)	2003-08-21	카프로락탐및헥사메틸렌디아민의동시제조방법
JPH09505571A (ja)	1997-06-03	カプロラクタムの製造方法
JP2012522823A (ja)	2012-09-27	１，６−ヘキサンジオールおよびカプロラクトンの製造方法
US6207851B1 (en)	2001-03-27	Process for simultaneously preparing 6-aminocapronitrile and hexamethylene diamine
US5874575A (en)	1999-02-23	Preparation of caprolactam
US5717090A (en)	1998-02-10	Simultaneous preparation of caprolactam and hexamethylenediamine
TW467882B (en)	2001-12-11	Improved process for coproduction of 6-aminocapronitrile and hexamethylenediamine
EP1268402B1 (en)	2004-09-29	Process for preparing 6-aminocaproamide
MXPA97004863A (en)	1998-07-03	Simultaneous preparation of caprolactama yhexametilendiam
MXPA97003955A (en)	1998-07-03	Caprolact preparation