CA2146903C - Reductive amination catalysts for the selective production of aminoethylethanolamine - Google Patents
Reductive amination catalysts for the selective production of aminoethylethanolamine Download PDFInfo
- Publication number
- CA2146903C CA2146903C CA002146903A CA2146903A CA2146903C CA 2146903 C CA2146903 C CA 2146903C CA 002146903 A CA002146903 A CA 002146903A CA 2146903 A CA2146903 A CA 2146903A CA 2146903 C CA2146903 C CA 2146903C
- Authority
- CA
- Canada
- Prior art keywords
- grams
- nickel
- catalyst
- alumina
- reductive amination
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
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- 239000003054 catalyst Substances 0.000 title claims abstract description 81
- 238000006268 reductive amination reaction Methods 0.000 title claims abstract 8
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 title claims abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 84
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 65
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 22
- 239000002184 metal Substances 0.000 claims abstract description 22
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 24
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052725 zinc Inorganic materials 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- 239000011777 magnesium Substances 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000000969 carrier Substances 0.000 abstract description 23
- 150000002739 metals Chemical class 0.000 abstract description 12
- 125000004122 cyclic group Chemical group 0.000 abstract description 5
- UJRJCSCBZXLGKF-UHFFFAOYSA-N nickel rhenium Chemical compound [Ni].[Re] UJRJCSCBZXLGKF-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000463 material Substances 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000001354 calcination Methods 0.000 description 21
- 230000000694 effects Effects 0.000 description 14
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- 239000000908 ammonium hydroxide Substances 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 229910052796 boron Inorganic materials 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 5
- 229940069446 magnesium acetate Drugs 0.000 description 5
- 239000011654 magnesium acetate Substances 0.000 description 5
- 235000011285 magnesium acetate Nutrition 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- -1 rh~)dium Chemical compound 0.000 description 4
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 235000010338 boric acid Nutrition 0.000 description 3
- 229960002645 boric acid Drugs 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000002734 clay mineral Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 3
- 229910001701 hydrotalcite Inorganic materials 0.000 description 3
- 229960001545 hydrotalcite Drugs 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910001679 gibbsite Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- QSHYGLAZPRJAEZ-UHFFFAOYSA-N 4-(chloromethyl)-2-(2-methylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC=C1C1=NC(CCl)=CS1 QSHYGLAZPRJAEZ-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 241001233887 Ania Species 0.000 description 1
- 241000370685 Arge Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102100033029 Carbonic anhydrase-related protein 11 Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 101000867841 Homo sapiens Carbonic anhydrase-related protein 11 Proteins 0.000 description 1
- 101001075218 Homo sapiens Gastrokine-1 Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 101001069962 Mus musculus Golgi apparatus protein 1 Proteins 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 108010039491 Ricin Proteins 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 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
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 101150010487 are gene Proteins 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910001593 boehmite Inorganic materials 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-M hydroxide;hydrate Chemical compound O.[OH-] JEGUKCSWCFPDGT-UHFFFAOYSA-M 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 1
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 229940078487 nickel acetate tetrahydrate Drugs 0.000 description 1
- OINIXPNQKAZCRL-UHFFFAOYSA-L nickel(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Ni+2].CC([O-])=O.CC([O-])=O OINIXPNQKAZCRL-UHFFFAOYSA-L 0.000 description 1
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- QQFIANJVEURFOA-UHFFFAOYSA-N tetraazanium dicarbonate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[O-]C([O-])=O.[O-]C([O-])=O QQFIANJVEURFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/14—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
-
- 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
- B01J23/007—Mixed salts
-
- 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
- B01J23/8896—Rhenium
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69512381T DE69512381T2 (de) | 1993-12-22 | 1995-04-12 | Reduktive Aminierung zur selektiven Herstellung von Aminoethylethanolamin |
| EP95302456A EP0737669B1 (en) | 1993-12-22 | 1995-04-12 | Reductive amination processes for the selective production of aminoethylethanolamine |
| CA002146903A CA2146903C (en) | 1993-12-22 | 1995-04-12 | Reductive amination catalysts for the selective production of aminoethylethanolamine |
| MX9501842A MX9501842A (es) | 1993-12-22 | 1995-04-19 | Procesos de aminacion reductivos para la produccion selectiva de aminoetiletanolamina. |
| KR1019950009689A KR100216935B1 (ko) | 1993-12-22 | 1995-04-25 | 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 |
| JP7125620A JP2876464B2 (ja) | 1993-12-22 | 1995-04-27 | アミノエチルエタノールアミンを選択的に製造するための還元アミノ化方法 |
| US08/465,186 US5891820A (en) | 1993-12-22 | 1995-06-05 | Reductive amination processes for the selective production of amino-ethyylethanolamine |
| US08/461,549 US5600000A (en) | 1993-12-22 | 1995-06-05 | Reductive amination processes for the selective production of amino-ethylethanolamine |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17153993A | 1993-12-22 | 1993-12-22 | |
| EP95302456A EP0737669B1 (en) | 1993-12-22 | 1995-04-12 | Reductive amination processes for the selective production of aminoethylethanolamine |
| CA002146903A CA2146903C (en) | 1993-12-22 | 1995-04-12 | Reductive amination catalysts for the selective production of aminoethylethanolamine |
| MX9501842A MX9501842A (es) | 1993-12-22 | 1995-04-19 | Procesos de aminacion reductivos para la produccion selectiva de aminoetiletanolamina. |
| KR1019950009689A KR100216935B1 (ko) | 1993-12-22 | 1995-04-25 | 아미노에틸에탄올아민을 선택적으로 제조하기 위한 환원 아민화 반응 촉매 및 이를 사용하는 환원 아민화 반응법 |
| JP7125620A JP2876464B2 (ja) | 1993-12-22 | 1995-04-27 | アミノエチルエタノールアミンを選択的に製造するための還元アミノ化方法 |
| US08/465,186 US5891820A (en) | 1993-12-22 | 1995-06-05 | Reductive amination processes for the selective production of amino-ethyylethanolamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2146903A1 CA2146903A1 (en) | 1996-10-13 |
| CA2146903C true CA2146903C (en) | 2000-01-25 |
Family
ID=32097192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002146903A Expired - Fee Related CA2146903C (en) | 1993-12-22 | 1995-04-12 | Reductive amination catalysts for the selective production of aminoethylethanolamine |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5891820A (OSRAM) |
| EP (1) | EP0737669B1 (OSRAM) |
| JP (1) | JP2876464B2 (OSRAM) |
| KR (1) | KR100216935B1 (OSRAM) |
| CA (1) | CA2146903C (OSRAM) |
| DE (1) | DE69512381T2 (OSRAM) |
| MX (1) | MX9501842A (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19706876A1 (de) * | 1997-02-21 | 1998-08-27 | Basf Ag | Verfahren zur Herstellung von Carbonsäuren oder deren Estern durch Carbonylierung von Olefinen |
| 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 |
| DE10028432A1 (de) * | 2000-06-13 | 2001-12-20 | Basell Polyolefine Gmbh | Auf calciniertes Hydrotalcit geträgerter Katalysatorfeststoff zur Olefinpolymerisation |
| DE10349059A1 (de) * | 2003-10-17 | 2005-05-19 | Basf Ag | Verfahren zur destillativen Auftrennung von Gemischen enthaltend Ethylenamine |
| JP4972315B2 (ja) * | 2005-12-28 | 2012-07-11 | 花王株式会社 | 含窒素化合物の製造方法 |
| CN101910107B (zh) | 2008-01-03 | 2013-03-13 | 阿克佐诺贝尔股份有限公司 | 制备亚乙基胺的方法 |
| US8383860B2 (en) | 2008-10-06 | 2013-02-26 | Union Carbide Chemicals & Plastics Technology Llc | Process to selectively manufacture diethylenetriamine (DETA) or other desirable ethyleneamines via continuous transamination of ethylenediamine (EDA), and other ethyleneamines over a heterogeneous catalyst system |
| 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 |
| WO2010042164A2 (en) | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Transalkoxylation of nucleophilic compounds |
| EP2346810B1 (en) | 2008-10-06 | 2015-08-19 | Dow Global Technologies LLC | Methods for making ethanolamine(s) and ethyleneamine(s) from ethylene oxide and ammonia, and related methods |
| CN102227413B (zh) | 2008-10-06 | 2014-11-05 | 联合碳化化学品及塑料技术公司 | 制备环状n-氨基官能化三胺的方法 |
| WO2010042161A1 (en) * | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Low metal (nickel and rhenium) catalyst compositions including acidic mixed metal oxide as support |
| BRPI0914054A2 (pt) | 2008-10-06 | 2015-11-03 | Union Carbide Chem Plastic | método para produzir etilenoaminas |
| WO2013095810A1 (en) * | 2011-12-22 | 2013-06-27 | Dow Global Technologies Llc | Reductive amination of diethanolamine and resulting product mixture |
| US9644066B2 (en) | 2011-12-29 | 2017-05-09 | Dow Global Technologies Llc | Cyclic amine compounds, compositions, and polyurethane foams made therefrom |
| EP2797901B1 (en) * | 2011-12-29 | 2017-05-10 | Dow Global Technologies Llc | Formation of higher molecular weight cyclic polyamine compounds from cyclic polyamine compounds |
| JP6401059B2 (ja) | 2011-12-29 | 2018-10-03 | ダウ グローバル テクノロジーズ エルエルシー | 環状アミン化合物から製造されたアミンポリエーテルポリオールおよびポリウレタンフォーム組成物 |
| CN105745251B (zh) | 2013-12-02 | 2019-04-23 | 陶氏环球技术有限责任公司 | 高分子量的、支化的、无环多亚烷基胺及其混合物的制备 |
| PL3189019T3 (pl) | 2014-09-03 | 2018-11-30 | Corning Incorporated | Korpus o strukturze plastra miodu z warstwowymi zatyczkami i sposób jego produkcji |
| CN114315613B (zh) * | 2021-12-27 | 2024-03-19 | 江苏康恒化工有限公司 | 一种羟乙基乙二胺的合成工艺 |
| CN118253311A (zh) * | 2024-04-08 | 2024-06-28 | 卫星化学股份有限公司 | 一种用于乙二胺和哌嗪制备的催化剂及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123462A (en) * | 1976-01-07 | 1978-10-31 | Union Carbide Corporation | Amination process using nickel-rhenium catalysts |
| GB8707304D0 (en) * | 1987-03-26 | 1987-04-29 | Bp Chem Int Ltd | Chemical process |
| US4973692A (en) | 1987-09-30 | 1990-11-27 | Union Carbide Chemicals And Plastics Company Inc. | Aminoethylethanolamine producers composition and method for producing same |
| US5202490A (en) * | 1987-09-30 | 1993-04-13 | Union Carbide Chemicals & Plastics Technology Corporation | Process for thr manufacture of diethylenetriamine and aminoethylethanolamine |
| US5352835A (en) * | 1993-02-08 | 1994-10-04 | Texaco Chemical Company | Supported catalysts for amination |
| US5340466A (en) * | 1993-04-19 | 1994-08-23 | Texaco Inc. | Hydrodesulfurization of cracked naphtha with hydrotalcite-containing catalyst |
-
1995
- 1995-04-12 DE DE69512381T patent/DE69512381T2/de not_active Expired - Lifetime
- 1995-04-12 CA CA002146903A patent/CA2146903C/en not_active Expired - Fee Related
- 1995-04-12 EP EP95302456A patent/EP0737669B1/en not_active Expired - Lifetime
- 1995-04-19 MX MX9501842A patent/MX9501842A/es unknown
- 1995-04-25 KR KR1019950009689A patent/KR100216935B1/ko not_active Expired - Fee Related
- 1995-04-27 JP JP7125620A patent/JP2876464B2/ja not_active Expired - Lifetime
- 1995-06-05 US US08/465,186 patent/US5891820A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR960037640A (ko) | 1996-11-19 |
| MX197579B (OSRAM) | 2000-07-18 |
| EP0737669A1 (en) | 1996-10-16 |
| KR100216935B1 (ko) | 1999-10-01 |
| JP2876464B2 (ja) | 1999-03-31 |
| JPH08319261A (ja) | 1996-12-03 |
| DE69512381T2 (de) | 2000-04-06 |
| CA2146903A1 (en) | 1996-10-13 |
| US5891820A (en) | 1999-04-06 |
| DE69512381D1 (de) | 1999-10-28 |
| EP0737669B1 (en) | 1999-09-22 |
| MX9501842A (es) | 1997-04-30 |
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