SK77397A3 - Process for preparing aliphatic alpha,omega-aminonitriles - Google Patents

Process for preparing aliphatic alpha,omega-aminonitriles Download PDF

Info

Publication number: SK77397A3
Authority: SK; Slovakia
Prior art keywords: catalyst; ruthenium; group; omega; iron
Prior art date: 1994-12-27

Application number

SK773-97A

Other languages

English (en)

Slovak (sk)

Inventor

Johann-Peter Melder

Werner Schnurr

Klemens Flick

Klaus Ebel

Tom Witzel

Rolf Fischer

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.)

1994-12-27

Filing date

1995-12-16

Publication date

1998-01-14

1995-12-16 Application filed by Basf Ag filed Critical Basf Ag

1998-01-14 Publication of SK77397A3 publication Critical patent/SK77397A3/sk

Links

125000001931 aliphatic group Chemical group 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title claims description 11
239000003054 catalyst Substances 0.000 claims abstract description 85
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 41
229910052742 iron Inorganic materials 0.000 claims abstract description 20
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 19
229910052751 metal Inorganic materials 0.000 claims abstract description 18
239000002184 metal Substances 0.000 claims abstract description 18
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 15
229910017052 cobalt Inorganic materials 0.000 claims abstract description 13
239000010941 cobalt Substances 0.000 claims abstract description 13
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 12
239000010948 rhodium Substances 0.000 claims abstract description 12
229910052703 rhodium Inorganic materials 0.000 claims abstract description 11
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 9
229910052759 nickel Inorganic materials 0.000 claims abstract description 9
239000002904 solvent Substances 0.000 claims abstract description 9
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052804 chromium Inorganic materials 0.000 claims abstract description 8
239000011651 chromium Substances 0.000 claims abstract description 8
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 claims abstract description 8
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 7
239000011733 molybdenum Substances 0.000 claims abstract description 7
229910052719 titanium Inorganic materials 0.000 claims abstract description 7
239000010936 titanium Substances 0.000 claims abstract description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052802 copper Inorganic materials 0.000 claims abstract description 5
239000010949 copper Substances 0.000 claims abstract description 5
229910052709 silver Inorganic materials 0.000 claims abstract description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 4
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052782 aluminium Inorganic materials 0.000 claims abstract description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052741 iridium Inorganic materials 0.000 claims abstract description 4
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
239000011574 phosphorus Substances 0.000 claims abstract description 4
229910052702 rhenium Inorganic materials 0.000 claims abstract description 4
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 4
239000004332 silver Substances 0.000 claims abstract description 4
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052721 tungsten Inorganic materials 0.000 claims abstract description 4
239000010937 tungsten Substances 0.000 claims abstract description 4
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 3
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052787 antimony Inorganic materials 0.000 claims abstract description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052785 arsenic Inorganic materials 0.000 claims abstract description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052797 bismuth Inorganic materials 0.000 claims abstract description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052793 cadmium Inorganic materials 0.000 claims abstract description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052737 gold Inorganic materials 0.000 claims abstract description 3
239000010931 gold Substances 0.000 claims abstract description 3
229910052762 osmium Inorganic materials 0.000 claims abstract description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052763 palladium Inorganic materials 0.000 claims abstract description 3
229910052697 platinum Inorganic materials 0.000 claims abstract description 3
229910052761 rare earth metal Inorganic materials 0.000 claims abstract description 3
150000002910 rare earth metals Chemical class 0.000 claims abstract description 3
229910052718 tin Inorganic materials 0.000 claims abstract description 3
229910052725 zinc Inorganic materials 0.000 claims abstract description 3
239000011701 zinc Substances 0.000 claims abstract description 3
229910052726 zirconium Inorganic materials 0.000 claims abstract description 3
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 46
238000000034 method Methods 0.000 claims description 26
238000005984 hydrogenation reaction Methods 0.000 claims description 17
KBMSFJFLSXLIDJ-UHFFFAOYSA-N 6-aminohexanenitrile Chemical compound NCCCCCC#N KBMSFJFLSXLIDJ-UHFFFAOYSA-N 0.000 claims description 6
239000000725 suspension Substances 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 3
229910052710 silicon Inorganic materials 0.000 claims description 2
239000010703 silicon Substances 0.000 claims description 2
239000011949 solid catalyst Substances 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 2
150000001342 alkaline earth metals Chemical class 0.000 abstract description 2
239000004411 aluminium Substances 0.000 abstract 1
239000011133 lead Substances 0.000 abstract 1
239000011135 tin Substances 0.000 abstract 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 36
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 24
229910052739 hydrogen Inorganic materials 0.000 description 22
239000001257 hydrogen Substances 0.000 description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
229910021529 ammonia Inorganic materials 0.000 description 15
239000000203 mixture Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 12
239000000395 magnesium oxide Substances 0.000 description 8
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Substances [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 7
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 7
239000011572 manganese Substances 0.000 description 7
229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000011734 sodium Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 5
239000000292 calcium oxide Substances 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910052748 manganese Inorganic materials 0.000 description 5
150000002823 nitrates Chemical class 0.000 description 5
239000002243 precursor Substances 0.000 description 5
-1 4-aminobutyric acid nitrile Chemical class 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
229910000428 cobalt oxide Inorganic materials 0.000 description 4
230000000977 initiatory effect Effects 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
230000004913 activation Effects 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000003841 chloride salts Chemical class 0.000 description 3
150000004675 formic acid derivatives Chemical class 0.000 description 3
UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
229910000480 nickel oxide Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FHKPTEOFUHYQFY-UHFFFAOYSA-N 2-aminohexanenitrile Chemical compound CCCCC(N)C#N FHKPTEOFUHYQFY-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
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000001354 calcination Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000012018 catalyst precursor Substances 0.000 description 2
238000003181 co-melting Methods 0.000 description 2
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-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
229910052744 lithium Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
238000002161 passivation Methods 0.000 description 2
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 2
229910001950 potassium oxide Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003623 transition metal compounds Chemical class 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
125000005219 aminonitrile group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000006227 byproduct Substances 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
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
239000003795 chemical substances by application Substances 0.000 description 1
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
229910001981 cobalt nitrate Inorganic materials 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000007423 decrease Effects 0.000 description 1
JJMDCOVWQOJGCB-UHFFFAOYSA-N delta-aminovaleric acid Natural products [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutanoic acid Natural products NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 description 1
LLEVMYXEJUDBTA-UHFFFAOYSA-N heptanedinitrile Chemical compound N#CCCCCCC#N LLEVMYXEJUDBTA-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
MIVBAHRSNUNMPP-UHFFFAOYSA-N manganese(2+);dinitrate Chemical compound [Mn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MIVBAHRSNUNMPP-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
238000007873 sieving Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910052566 spinel group Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8898—Manganese, technetium or rhenium containing also molybdenum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Catalysts (AREA)
Peptides Or Proteins (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK773-97A 1994-12-27 1995-12-16 Process for preparing aliphatic alpha,omega-aminonitriles SK77397A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4446893A DE4446893A1 (de)	1994-12-27	1994-12-27	Verfahren zur Herstellung von aliphatischen alpha,omega-Aminonitrilen
PCT/EP1995/004985 WO1996020166A1 (de)	1994-12-27	1995-12-16	Verfahren zur herstellung von aliphatischen alpha,omega-aminonitrilen

Publications (1)

Publication Number	Publication Date
SK77397A3 true SK77397A3 (en)	1998-01-14

Family

ID=6537318

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK773-97A SK77397A3 (en)	1994-12-27	1995-12-16	Process for preparing aliphatic alpha,omega-aminonitriles

Country Status (25)

Country	Link
US (2)	US5527946A (cs)
EP (1)	EP0800508B1 (cs)
JP (1)	JP4017023B2 (cs)
KR (1)	KR100404399B1 (cs)
CN (1)	CN1075492C (cs)
AT (1)	ATE191463T1 (cs)
AU (1)	AU701523B2 (cs)
BG (1)	BG63299B1 (cs)
BR (1)	BR9510109A (cs)
CA (1)	CA2208775C (cs)
CZ (1)	CZ288943B6 (cs)
DE (2)	DE4446893A1 (cs)
DK (1)	DK0800508T3 (cs)
ES (1)	ES2145941T3 (cs)
FI (1)	FI972762A0 (cs)
GR (1)	GR3033456T3 (cs)
HU (1)	HU223965B1 (cs)
MY (1)	MY113215A (cs)
NO (1)	NO307781B1 (cs)
NZ (1)	NZ297803A (cs)
PL (1)	PL181432B1 (cs)
PT (1)	PT800508E (cs)
RU (1)	RU2154630C2 (cs)
SK (1)	SK77397A3 (cs)
WO (1)	WO1996020166A1 (cs)

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DE69413560T2 (de) *	1993-12-28	1999-04-22	Rhodia Fiber & Resin Intermediates, Courbevoie	Verfahren zur herstellung eines katalysators für die hydrierung von nitrilen in aminen und verwendung dieses katalysators in der hydrierung
FR2738757B1 (fr) *	1995-09-15	1997-10-31	Rhone Poulenc Fibres	Nouveaux composes metalliques utilisables comme catalyseurs
DE19636768A1 (de) *	1996-09-10	1998-03-12	Basf Ag	Für die Herstellung von aliphatischen alpha, omega-Aminonitrilen durch partielle Hydrierung von aliphatischen Dinitrilen geeignete Katalysatoren
WO1998011059A1 (de)	1996-09-10	1998-03-19	Basf Aktiengesellschaft	Verfahren zur herstellung von aliphatischen alpha, omega-aminonitrilen
DE19704614A1 (de)	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Abtrennnung eines Imins aus einer Mischung enthaltend ein Amin und ein Imin
DE19704615A1 (de) *	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Hydrierung von Verbindungen aus der Gruppe der Imine oder Enamine
DE19704612A1 (de) *	1997-02-07	1998-08-13	Basf Ag	Verfahren zur Gewinnung von Hexamethylendiamin aus Hexamethylendiamin enthaltenden Mischungen
US6127310A (en) *	1997-02-27	2000-10-03	Phillips Petroleum Company	Palladium containing hydrogenation catalysts
DE19742221A1 (de) *	1997-09-24	1999-03-25	Basf Ag	Verfahren zur Herstellung von aliphatischen alpha,omega-Aminonitrilen
DE19809687A1 (de) *	1998-03-06	1999-09-09	Basf Ag	Hydrierkatalysator
US5986127A (en) *	1999-03-15	1999-11-16	E. I. Du Pont De Nemours And Company	Aminonitrile production
ES2232121T3 (es) *	1998-03-20	2005-05-16	Invista Technologies S.A.R.L.	Produccion de aminonitrilo.
US6080884A (en) *	1998-03-20	2000-06-27	E. I. Du Pont De Nemours And Company	Aminonitrile production
FR2777562B1 (fr) *	1998-04-16	2002-07-19	Rhone Poulenc Fibres	Procede de purification d'aminonitriles aliphatiques
FR2778661B1 (fr) *	1998-05-15	2000-06-16	Rhone Poulenc Fibres	Procede de preparation d'aminonitrile et de diamine
DE19830598A1 (de)	1998-07-09	2000-01-13	Basf Ag	Verfahren zur Reduzierung des Gehalts an einem ungesättigten cyclischen Imin in einer Mischung enthaltend Hexamethylendiamin und dieses Imin
US6346641B1 (en)	1998-07-20	2002-02-12	Basf Aktiengesellschaft	Method for simultaneous production of 6-aminocapronitrile and hexamethylenediamine
DE19839338A1 (de)	1998-08-28	2000-03-02	Basf Ag	Verbessertes Verfahren zur gleizeitigen Herstellung von 6-Aminocapronitril und Hexamethylendiamin
US6129774A (en) *	1998-09-24	2000-10-10	Clean Air Flow, Inc.	Clean air flow catalyst
FR2785608B1 (fr) *	1998-11-05	2000-12-29	Rhone Poulenc Fibres	Procede d'hemihydrogenation de dinitriles
US6258745B1 (en)	1999-04-28	2001-07-10	E. I. Du Pont De Nemours And Company	Aminonitrile production
US6841507B2 (en) *	1999-11-30	2005-01-11	Invista North America S.A.R.L.	Aminonitrile production
US6680403B1 (en)	1999-11-30	2004-01-20	E. I. Du Pont De Nemours And Company	Process for hydrogenating dinitriles in aminonitriles
US6569802B1 (en)	1999-11-30	2003-05-27	E. I. Du Pont De Nemours And Company	Catalyst for selective hydrogenation of dinitriles
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
US6566297B2 (en)	2000-03-10	2003-05-20	E. I. Du Pont De Nemours And Company	Aminonitrile production
US6686465B2 (en)	2000-05-03	2004-02-03	Basf Aktiengesellschaft	Preparation of cyclic lactams
RU2278731C2 (ru) *	2000-09-29	2006-06-27	Чайна Петролеум Энд Кемикал Корпорейшн	Катализатор селективного гидрирования ненасыщенных олефинов, способ получения и применения катализатора
US6776606B2 (en)	2001-03-02	2004-08-17	Emmissions Technology, Llc	Method for oxidizing mixtures
FR2826363B1 (fr) *	2001-06-22	2005-01-14	Rhodia Polyamide Intermediates	Procede d'hemihydrogenation de dinitriles en aminonitriles
US6506927B1 (en)	2001-10-02	2003-01-14	E. I. Du Pont De Nemours And Company	Aminonitrile production
US6710201B2 (en)	2001-10-02	2004-03-23	E. I. Du Pont De Nemours And Company	Aminonitrile production
US6455723B1 (en)	2001-10-02	2002-09-24	E. I. Du Pont De Nemours And Company	Aminonitrile production
US6455724B1 (en)	2001-10-02	2002-09-24	E. I. Du Pont De Nemours And Company	Aminonitrile production
DE10151558A1 (de) *	2001-10-23	2003-04-30	Basf Ag	Als Katalysatorvorstufe geeignete oxidische Masse
DE10151559A1 (de) *	2001-10-23	2003-04-30	Basf Ag	Als Katalysator geeignete Masse
EP1449825B1 (en) *	2003-02-20	2009-01-14	Mitsubishi Gas Chemical Company, Inc.	High-selective production method of di(aminomethyl)-substituted aromatic compound
JP2008522969A (ja) *	2004-12-07	2008-07-03	インヴィスタテクノロジーエスアエルエル	ジニトリル水素化方法における調節剤の使用
UA100025C2 (ru) *	2007-08-02	2012-11-12	Сейсол Текнолоджи (Пти) Лимитед	Способ изготовления катализатора синтеза углеводородов и его использование в процессе синтеза углеводородов
EP2506965B1 (de) *	2009-12-03	2016-11-09	Basf Se	Katalysator und verfahren zur herstellung eines amins
BR112021010590A2 (pt) *	2018-12-03	2021-08-24	Basf Corporation	Catalisadores de hidrogenação, métodos de preparação de um catalisador de hidrogenação calcinado, de hidrogenação de uma cetona ou aldeído, de síntese de butanodiol e de hidrogenação de um éster e catalisador do método

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US2257814A (en) *	1940-05-02	1941-10-07	Du Pont	Preparation of omega-amino nitriles
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BE757761R (fr) *	1969-10-27	1971-04-20	Ici Ltd	Procede de production de diamines
US4389348A (en) *	1981-10-26	1983-06-21	Allied Corporation	Selective hydrogenation of dinitrile to omega-aminonitrile and supported rhodium-containing catalyst therefor
US4601859A (en) *	1984-05-04	1986-07-22	Allied Corporation	Selective hydrogenation of aliphatic dinitriles to omega-aminonitriles in ammonia with supported, finely dispersed rhodium-containing catalyst
US5151543A (en) *	1991-05-31	1992-09-29	E. I. Du Pont De Nemours And Company	Selective low pressure hydrogenation of a dinitrile to an aminonitrile
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US5296628A (en) *	1992-02-13	1994-03-22	E. I. Du Pont De Nemours And Company	Preparation of 6-aminocapronitrile
DE4235466A1 (de) *	1992-10-21	1994-04-28	Bayer Ag	Verfahren zur Herstellung von (cyclo)aliphatischen Aminonitrilen

1994
- 1994-12-27 DE DE4446893A patent/DE4446893A1/de not_active Withdrawn
1995
- 1995-01-18 US US08/375,573 patent/US5527946A/en not_active Expired - Lifetime
- 1995-12-16 CN CN95197137A patent/CN1075492C/zh not_active Expired - Lifetime
- 1995-12-16 DK DK95941718T patent/DK0800508T3/da active
- 1995-12-16 AU AU43047/96A patent/AU701523B2/en not_active Ceased
- 1995-12-16 AT AT95941718T patent/ATE191463T1/de not_active IP Right Cessation
- 1995-12-16 NZ NZ297803A patent/NZ297803A/xx unknown
- 1995-12-16 RU RU97112897/04A patent/RU2154630C2/ru not_active IP Right Cessation
- 1995-12-16 PL PL95321064A patent/PL181432B1/pl not_active IP Right Cessation
- 1995-12-16 PT PT95941718T patent/PT800508E/pt unknown
- 1995-12-16 EP EP95941718A patent/EP0800508B1/de not_active Expired - Lifetime
- 1995-12-16 CZ CZ19971976A patent/CZ288943B6/cs not_active IP Right Cessation
- 1995-12-16 CA CA002208775A patent/CA2208775C/en not_active Expired - Fee Related
- 1995-12-16 HU HU9702137A patent/HU223965B1/hu not_active IP Right Cessation
- 1995-12-16 ES ES95941718T patent/ES2145941T3/es not_active Expired - Lifetime
- 1995-12-16 SK SK773-97A patent/SK77397A3/sk unknown
- 1995-12-16 WO PCT/EP1995/004985 patent/WO1996020166A1/de not_active Ceased
- 1995-12-16 BR BR9510109A patent/BR9510109A/pt not_active IP Right Cessation
- 1995-12-16 JP JP52017596A patent/JP4017023B2/ja not_active Expired - Fee Related
- 1995-12-16 DE DE59508153T patent/DE59508153D1/de not_active Expired - Lifetime
- 1995-12-16 KR KR1019970704415A patent/KR100404399B1/ko not_active Expired - Fee Related
- 1995-12-19 MY MYPI95003931A patent/MY113215A/en unknown
1997
- 1997-06-17 BG BG101631A patent/BG63299B1/bg unknown
- 1997-06-26 FI FI972762A patent/FI972762A0/fi not_active IP Right Cessation
- 1997-06-26 NO NO972997A patent/NO307781B1/no unknown
1998
- 1998-07-24 US US09/122,102 patent/US6114567A/en not_active Expired - Lifetime
2000
- 2000-05-19 GR GR20000401145T patent/GR3033456T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
BG101631A (en)	1998-02-27
DE4446893A1 (de)	1996-07-04
FI972762A7 (fi)	1997-06-26
EP0800508B1 (de)	2000-04-05
MX9704756A (es)	1997-10-31
HU223965B1 (hu)	2005-03-29
KR980700960A (ko)	1998-04-30
KR100404399B1 (ko)	2004-04-29
BR9510109A (pt)	1997-11-25
PL321064A1 (en)	1997-11-24
CN1075492C (zh)	2001-11-28
ATE191463T1 (de)	2000-04-15
MY113215A (en)	2001-12-31
CZ288943B6 (cs)	2001-10-17
CA2208775A1 (en)	1996-07-04
CA2208775C (en)	2005-07-05
NO307781B1 (no)	2000-05-29
WO1996020166A1 (de)	1996-07-04
AU4304796A (en)	1996-07-19
PT800508E (pt)	2000-07-31
DK0800508T3 (da)	2000-07-17
NO972997D0 (no)	1997-06-26
EP0800508A1 (de)	1997-10-15
AU701523B2 (en)	1999-01-28
JP4017023B2 (ja)	2007-12-05
NO972997L (no)	1997-06-26
BG63299B1 (bg)	2001-09-28
CZ197697A3 (cs)	1998-03-18
GR3033456T3 (en)	2000-09-29
RU2154630C2 (ru)	2000-08-20
FI972762A0 (fi)	1997-06-26
HUT77021A (hu)	1998-03-02
JPH10511372A (ja)	1998-11-04
PL181432B1 (pl)	2001-07-31
DE59508153D1 (de)	2000-05-11
ES2145941T3 (es)	2000-07-16
NZ297803A (en)	1999-08-30
CN1171776A (zh)	1998-01-28
US6114567A (en)	2000-09-05
US5527946A (en)	1996-06-18

Publication	Publication Date	Title
SK77397A3 (en)	1998-01-14	Process for preparing aliphatic alpha,omega-aminonitriles
US6265602B1 (en)	2001-07-24	Method for hydrogenating aliphatic alpha-, omega-dinitriles
KR100938300B1 (ko)	2010-01-22	이소포론디아민(ｉｐｄａ,3-아미노메틸-3,5,5-트리메틸시클로헥실아민)의 제조 방법
CZ81099A3 (cs)	1999-06-16	Způsob současné výroby nitrilu kyseliny 6-aminokapronové a hexamethylendiaminu
KR100502606B1 (ko)	2005-07-22	지방족 디니트릴의 부분 수소화에 의한 지방족 알파-, 오메가-아미노니트릴의 제조에 적합한 촉매
US6815388B1 (en)	2004-11-09	Method for activating passivated iron
KR100468184B1 (ko)	2005-01-26	지방족 알파,오메가-아미노 니트릴의 제조 방법
US5801268A (en)	1998-09-01	Preparation of aliphatic alpha omega-aminonitriles
KR20040045897A (ko)	2004-06-02	수소화 촉매로서 사용하는데 적합한 철 함유 물질
MXPA97004756A (en)	1998-07-03	Preparation of alpha, w- aminonitrilos alifati
MXPA00001787A (en)	2001-03-05	Method for producing aliphatic alpha, omega-amino nitriles
MXPA00008229A (en)	2001-07-09	Method for hydrogenating aliphatic alpha-, omega-dinitriles