SE524126C2 - Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiamin - Google Patents
Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiaminInfo
- Publication number
- SE524126C2 SE524126C2 SE0102590A SE0102590A SE524126C2 SE 524126 C2 SE524126 C2 SE 524126C2 SE 0102590 A SE0102590 A SE 0102590A SE 0102590 A SE0102590 A SE 0102590A SE 524126 C2 SE524126 C2 SE 524126C2
- Authority
- SE
- Sweden
- Prior art keywords
- weight
- catalyst
- process according
- alumina
- ethylenediamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- -1 polyethylene Polymers 0.000 title claims abstract description 21
- 230000008569 process Effects 0.000 title claims abstract description 20
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000005891 transamination reaction Methods 0.000 title claims abstract description 18
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000004698 Polyethylene Substances 0.000 title claims description 13
- 229920000573 polyethylene Polymers 0.000 title claims description 13
- 229920000768 polyamine Polymers 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000377 silicon dioxide Substances 0.000 claims description 17
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052702 rhenium Inorganic materials 0.000 claims description 8
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 12
- 125000002015 acyclic group Chemical group 0.000 abstract description 7
- 229910052759 nickel Inorganic materials 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000007306 turnover Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000295 complement effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000004157 Nitrosyl chloride Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001260 acyclic compounds Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PNPIRSNMYIHTPS-UHFFFAOYSA-N nitroso nitrate Chemical compound [O-][N+](=O)ON=O PNPIRSNMYIHTPS-UHFFFAOYSA-N 0.000 description 1
- YLPJWCDYYXQCIP-UHFFFAOYSA-N nitroso nitrate;ruthenium Chemical compound [Ru].[O-][N+](=O)ON=O YLPJWCDYYXQCIP-UHFFFAOYSA-N 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical group 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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)
- Catalysts (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102590A SE524126C2 (sv) | 2001-07-24 | 2001-07-24 | Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiamin |
| RU2004105150/04A RU2281936C2 (ru) | 2001-07-24 | 2002-07-05 | Способ получения диэтилентриамина и других линейных полиэтиленполиаминов |
| JP2003515486A JP4979877B2 (ja) | 2001-07-24 | 2002-07-05 | ジエチレントリアミンおよび高級ポリエチレンポリアミンの製造のための方法 |
| EP02749479A EP1409447B1 (de) | 2001-07-24 | 2002-07-05 | Verfahren zur herstellung von diethylentriamin und höheren polyethylenpolyaminen |
| DE60237610T DE60237610D1 (de) | 2001-07-24 | 2002-07-05 | Verfahren zur herstellung von diethylentriamin und höheren polyethylenpolyaminen |
| BR0211260-4A BR0211260A (pt) | 2001-07-24 | 2002-07-05 | Processo de preparação de dietilenotriamina e polietilenopoliaminas superiores |
| US10/484,323 US7053247B2 (en) | 2001-07-24 | 2002-07-05 | Process for the manufacture of diethylenetriamine and higher polyethylenepolyamines |
| CA2446989A CA2446989C (en) | 2001-07-24 | 2002-07-05 | A process for the manufacture of diethylenetriamine and higher polyethylenepolyamines |
| KR1020047000634A KR100847283B1 (ko) | 2001-07-24 | 2002-07-05 | 디에틸렌트리아민 및 고급 폴리에틸렌폴리아민의 제조 방법 |
| CNB028130855A CN1243718C (zh) | 2001-07-24 | 2002-07-05 | 生产二亚乙基三胺和更高级的聚亚乙基多胺的方法 |
| PCT/SE2002/001351 WO2003010125A1 (en) | 2001-07-24 | 2002-07-05 | A process for the manufacture of diethylenetriamine and higher polyethylenepolyamines |
| AT02749479T ATE480514T1 (de) | 2001-07-24 | 2002-07-05 | Verfahren zur herstellung von diethylentriamin und höheren polyethylenpolyaminen |
| MXPA04000399A MXPA04000399A (es) | 2001-07-24 | 2002-07-05 | Un proceso para la elaboracion de dietilentriamina y polietilenpoliaminas superiores. |
| TW091115200A TWI284121B (en) | 2001-07-24 | 2002-07-09 | A process for the manufacture of diethylenetriamine and higher polyethylenepolyamines |
| ARP020102742A AR034834A1 (es) | 2001-07-24 | 2002-07-22 | Un proceso para la manufactura de dietilentriamina y polietilenpoliaminas superiores. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102590A SE524126C2 (sv) | 2001-07-24 | 2001-07-24 | Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiamin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE0102590D0 SE0102590D0 (sv) | 2001-07-24 |
| SE0102590L SE0102590L (sv) | 2003-01-25 |
| SE524126C2 true SE524126C2 (sv) | 2004-06-29 |
Family
ID=20284920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0102590A SE524126C2 (sv) | 2001-07-24 | 2001-07-24 | Förfarande för framställning av dietylentriamin och högre polyetylenpolyaminer genom transaminering av etylendiamin |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7053247B2 (de) |
| EP (1) | EP1409447B1 (de) |
| JP (1) | JP4979877B2 (de) |
| KR (1) | KR100847283B1 (de) |
| CN (1) | CN1243718C (de) |
| AR (1) | AR034834A1 (de) |
| AT (1) | ATE480514T1 (de) |
| BR (1) | BR0211260A (de) |
| CA (1) | CA2446989C (de) |
| DE (1) | DE60237610D1 (de) |
| MX (1) | MXPA04000399A (de) |
| RU (1) | RU2281936C2 (de) |
| SE (1) | SE524126C2 (de) |
| TW (1) | TWI284121B (de) |
| WO (1) | WO2003010125A1 (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1654215B1 (de) | 2003-08-01 | 2006-11-02 | Basf Aktiengesellschaft | Verfahren zur herstellung von ethylenaminen |
| DE10335991A1 (de) | 2003-08-01 | 2005-02-24 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
| EP1934166B1 (de) * | 2005-09-30 | 2009-11-11 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| CN101277922B (zh) | 2005-09-30 | 2011-08-17 | 巴斯夫欧洲公司 | 生产亚乙基胺的方法 |
| JP5124486B2 (ja) | 2006-02-14 | 2013-01-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 触媒の存在でモノエチレングリコール及びアンモニアの水素化アミノ化によるエチレンアミン及びエタノールアミンの製造方法 |
| JP4938802B2 (ja) | 2006-02-14 | 2012-05-23 | ビーエーエスエフ ソシエタス・ヨーロピア | モノエチレングリコール(meg)からのエチレンアミン及びエタノールアミンの製造方法 |
| EP2346602B1 (de) * | 2008-09-19 | 2014-03-19 | Basf Se | Verfahren zur kontinuierlichen herstellung eines amins unter verwendung eines aluminium-kupfer-katalysators |
| US8187997B2 (en) * | 2008-10-06 | 2012-05-29 | Union Carbide Chemicals & Technology LLC | Low metal loaded, catalyst compositions including acidic mixed metal oxide as support |
| EP2346810B1 (de) * | 2008-10-06 | 2015-08-19 | Dow Global Technologies LLC | Verfahren zur herstellung von ethanolamin(en) und ethylenamin(en) aus ethylenoxid und ammoniak, und verwandte verfahren |
| US8124808B2 (en) * | 2008-10-06 | 2012-02-28 | Union Carbide Chemicals & Plastics Technology Llc | Transalkoxylation of nucleophilic compounds |
| CN102171178B (zh) * | 2008-10-06 | 2015-07-29 | 联合碳化化学品及塑料技术公司 | 乙二胺和其它乙撑胺的连续氨基转移 |
| CN102239002B (zh) | 2008-10-06 | 2013-10-30 | 联合碳化化学品及塑料技术公司 | 低金属负载的氧化铝载体的催化剂组合物和氨基化方法 |
| WO2010042159A1 (en) | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Methods of making cyclic, n-amino functional triamines |
| ES2561362T3 (es) * | 2008-10-06 | 2016-02-25 | Union Carbide Chemicals & Plastics Technology Llc | Método de fabricación de etilenaminas |
| CA2785949A1 (en) * | 2010-01-04 | 2011-07-07 | Rhodia Operations | Polyamine and method for producing thereof |
| JP6006222B2 (ja) * | 2010-11-10 | 2016-10-12 | ダウ グローバル テクノロジーズ エルエルシー | 環状ポリアミン及び環状/非環状ポリアミン混合物を製造するための窒素含有化合物のアミノ基転移 |
| CN103261147B (zh) | 2010-11-10 | 2016-11-23 | 陶氏环球技术有限责任公司 | 含氮化合物转氨基为高分子量聚亚烷基胺 |
| ES2628884T3 (es) | 2011-12-29 | 2017-08-04 | Dow Global Technologies Llc | Composiciones que contienen compuestos de amina cíclica, y espumas de poliuretano elaboradas con ellos |
| US9611351B2 (en) | 2011-12-29 | 2017-04-04 | Dow Global Technologies Llc. | Amine polyether polyols and polyurethane foam compositions made from cyclic amine compounds |
| EP2797901B1 (de) | 2011-12-29 | 2017-05-10 | Dow Global Technologies Llc | Herstellung von höhermolekularen cyclischen polyaminverbindungen aus cyclischen polyaminverbindungen |
| WO2014131649A1 (de) * | 2013-02-28 | 2014-09-04 | Basf Se | Polyamine und verfahren zu deren herstellung |
| US8987518B2 (en) | 2013-02-28 | 2015-03-24 | Basf Se | Polyamines and process for preparation thereof |
| EP3077444B1 (de) | 2013-12-02 | 2018-04-25 | Dow Global Technologies LLC | Herstellung von hochmolekularen, verzweigten, acyclischen polyalkylenaminen und mischungen davon |
| US10189946B2 (en) | 2014-02-26 | 2019-01-29 | Basf Se | Process for preparing polyamines |
| CN108772074B (zh) * | 2018-05-31 | 2021-01-05 | 西安近代化学研究所 | 一种乙二胺加氢制二乙烯三胺的催化剂及其制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2439275B2 (de) * | 1974-08-16 | 1978-09-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Diäthylentriamin und Triäthylentetramin aus Äthylendiamin |
| US4568746A (en) | 1982-12-29 | 1986-02-04 | Union Carbide Corporation | Catalytic preparation of diethylenetriamine |
| JPS6398355A (ja) * | 1986-10-16 | 1988-04-28 | Kazumitsu Maruta | 動物用飼料 |
| DE3811038A1 (de) * | 1988-03-31 | 1989-10-12 | Ruhrchemie Ag | Verfahren zur herstellung nickel, aluminiumoxid und zirkondioxid enthaltender katalysatorzusammensetzungen |
| US5243078A (en) * | 1989-06-23 | 1993-09-07 | Air Products And Chemicals, Inc. | Production of noncyclic polyalkylene polyamines |
| US5410086A (en) | 1989-06-27 | 1995-04-25 | Burgess; Lloyd M. | Selective preparation of diethylenetriamine |
| US5817593A (en) * | 1995-06-02 | 1998-10-06 | The Dow Chemical Company | Catalyst and process for producing amines |
| DE19645047A1 (de) | 1996-10-31 | 1998-05-07 | Basf Ag | Katalysatoren für die Aminierung von Alkylenoxiden, Alkoholen, Aldehyden und Ketonen |
| SE513250C2 (sv) * | 1997-11-11 | 2000-08-07 | Akzo Nobel Nv | Amineringsförfarande för framställning av polyaminer |
| US6534441B1 (en) | 1999-03-06 | 2003-03-18 | Union Carbide Chemicals & Plastics Technology Corporation | Nickel-rhenium catalyst for use in reductive amination processes |
| SE9903993L (sv) * | 1999-11-03 | 2001-05-04 | Satsafe Mls Ab | System för positionsbestämning av fordon och lastbärare |
-
2001
- 2001-07-24 SE SE0102590A patent/SE524126C2/sv not_active IP Right Cessation
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2002
- 2002-07-05 CN CNB028130855A patent/CN1243718C/zh not_active Expired - Fee Related
- 2002-07-05 CA CA2446989A patent/CA2446989C/en not_active Expired - Fee Related
- 2002-07-05 KR KR1020047000634A patent/KR100847283B1/ko not_active Expired - Fee Related
- 2002-07-05 US US10/484,323 patent/US7053247B2/en not_active Expired - Fee Related
- 2002-07-05 RU RU2004105150/04A patent/RU2281936C2/ru not_active IP Right Cessation
- 2002-07-05 BR BR0211260-4A patent/BR0211260A/pt active Search and Examination
- 2002-07-05 MX MXPA04000399A patent/MXPA04000399A/es active IP Right Grant
- 2002-07-05 AT AT02749479T patent/ATE480514T1/de not_active IP Right Cessation
- 2002-07-05 DE DE60237610T patent/DE60237610D1/de not_active Expired - Lifetime
- 2002-07-05 WO PCT/SE2002/001351 patent/WO2003010125A1/en not_active Ceased
- 2002-07-05 EP EP02749479A patent/EP1409447B1/de not_active Expired - Lifetime
- 2002-07-05 JP JP2003515486A patent/JP4979877B2/ja not_active Expired - Fee Related
- 2002-07-09 TW TW091115200A patent/TWI284121B/zh not_active IP Right Cessation
- 2002-07-22 AR ARP020102742A patent/AR034834A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR0211260A (pt) | 2004-07-27 |
| SE0102590D0 (sv) | 2001-07-24 |
| SE0102590L (sv) | 2003-01-25 |
| JP2004536866A (ja) | 2004-12-09 |
| MXPA04000399A (es) | 2004-03-18 |
| AR034834A1 (es) | 2004-03-17 |
| US20040171884A1 (en) | 2004-09-02 |
| KR100847283B1 (ko) | 2008-07-21 |
| RU2281936C2 (ru) | 2006-08-20 |
| JP4979877B2 (ja) | 2012-07-18 |
| DE60237610D1 (de) | 2010-10-21 |
| CN1522240A (zh) | 2004-08-18 |
| KR20040029367A (ko) | 2004-04-06 |
| US7053247B2 (en) | 2006-05-30 |
| EP1409447A1 (de) | 2004-04-21 |
| TWI284121B (en) | 2007-07-21 |
| CA2446989A1 (en) | 2003-02-06 |
| CA2446989C (en) | 2010-09-14 |
| ATE480514T1 (de) | 2010-09-15 |
| CN1243718C (zh) | 2006-03-01 |
| RU2004105150A (ru) | 2005-08-10 |
| WO2003010125A1 (en) | 2003-02-06 |
| EP1409447B1 (de) | 2010-09-08 |
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