CA1083558A - Nickel-rhenium hydrogenation catalyst and methods of preparing same and using same - Google Patents
Nickel-rhenium hydrogenation catalyst and methods of preparing same and using sameInfo
- Publication number
- CA1083558A CA1083558A CA268,485A CA268485A CA1083558A CA 1083558 A CA1083558 A CA 1083558A CA 268485 A CA268485 A CA 268485A CA 1083558 A CA1083558 A CA 1083558A
- Authority
- CA
- Canada
- Prior art keywords
- nickel
- catalyst
- rhenium
- support material
- silica
- 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
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 206
- 238000000034 method Methods 0.000 title claims abstract description 93
- UJRJCSCBZXLGKF-UHFFFAOYSA-N nickel rhenium Chemical compound [Ni].[Re] UJRJCSCBZXLGKF-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000005984 hydrogenation reaction Methods 0.000 title description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 144
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 91
- 238000006243 chemical reaction Methods 0.000 claims abstract description 89
- 230000008569 process Effects 0.000 claims abstract description 66
- 229910052751 metal Inorganic materials 0.000 claims abstract description 61
- 239000002184 metal Substances 0.000 claims abstract description 61
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 58
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 56
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 31
- 125000004429 atom Chemical group 0.000 claims abstract description 18
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 68
- 238000005576 amination reaction Methods 0.000 claims description 58
- 239000000463 material Substances 0.000 claims description 51
- 239000000047 product Substances 0.000 claims description 45
- 230000000694 effects Effects 0.000 claims description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 41
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 38
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 26
- 230000003197 catalytic effect Effects 0.000 claims description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
- 229910052796 boron Inorganic materials 0.000 claims description 17
- 230000009467 reduction Effects 0.000 claims description 17
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 15
- 239000000377 silicon dioxide Substances 0.000 claims description 15
- 239000000376 reactant Substances 0.000 claims description 13
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 7
- 239000010941 cobalt Substances 0.000 claims description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 239000005909 Kieselgur Substances 0.000 claims 1
- 125000003916 ethylene diamine group Chemical group 0.000 claims 1
- 229940117927 ethylene oxide Drugs 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 229910001868 water Inorganic materials 0.000 description 35
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 31
- 229940093476 ethylene glycol Drugs 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229940012017 ethylenediamine Drugs 0.000 description 18
- 238000005470 impregnation Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 229960005141 piperazine Drugs 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 15
- 230000002829 reductive effect Effects 0.000 description 15
- 238000001035 drying Methods 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- 239000002002 slurry Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- -1 heterocyclic amines Chemical class 0.000 description 10
- 150000002739 metals Chemical class 0.000 description 9
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000001354 calcination Methods 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 229940031098 ethanolamine Drugs 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910020442 SiO2—TiO2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052681 coesite Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052906 cristobalite Inorganic materials 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910052682 stishovite Inorganic materials 0.000 description 3
- 229910052905 tridymite Inorganic materials 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 229910001203 Alloy 20 Inorganic materials 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- 241001072332 Monia Species 0.000 description 2
- 229910018590 Ni(NO3)2-6H2O Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003281 rhenium Chemical class 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- QQGISFDJEJMKIL-JAIQZWGSSA-N (5z)-5-[[3-(hydroxymethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1CO QQGISFDJEJMKIL-JAIQZWGSSA-N 0.000 description 1
- UXGRXJVMQSSUGS-UHFFFAOYSA-N 1,2-dinitroethane Chemical compound [O-][N+](=O)CC[N+]([O-])=O UXGRXJVMQSSUGS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KZEVSDGEBAJOTK-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[5-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CC=1OC(=NN=1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O KZEVSDGEBAJOTK-UHFFFAOYSA-N 0.000 description 1
- OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical class CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 description 1
- NPEIGRBGMUJNFE-UHFFFAOYSA-N 1-aminohexan-1-ol Chemical class CCCCCC(N)O NPEIGRBGMUJNFE-UHFFFAOYSA-N 0.000 description 1
- WGAOZGUUHIBABN-UHFFFAOYSA-N 1-aminopentan-1-ol Chemical class CCCCC(N)O WGAOZGUUHIBABN-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- 241000370685 Arge Species 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229910021094 Co(NO3)2-6H2O Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 241000353097 Molva molva Species 0.000 description 1
- 241001508687 Mustela erminea Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 241000282337 Nasua nasua Species 0.000 description 1
- 229910018054 Ni-Cu Inorganic materials 0.000 description 1
- 229910018481 Ni—Cu Inorganic materials 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- 229910010066 TiC14 Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005441 aurora Substances 0.000 description 1
- YIRLUIDCBMHRSU-UHFFFAOYSA-N azane;1,2-dichloroethane Chemical compound N.ClCCCl YIRLUIDCBMHRSU-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GMDNUWQNDQDBNQ-UHFFFAOYSA-L magnesium;diformate Chemical class [Mg+2].[O-]C=O.[O-]C=O GMDNUWQNDQDBNQ-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical class [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LVMODVWPPKTXBE-UHFFFAOYSA-N nickel;2-oxopropyl acetate Chemical compound [Ni].CC(=O)COC(C)=O LVMODVWPPKTXBE-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical compound [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000003870 refractory metal Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 229910052725 zinc 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
- B01J23/8896—Rhenium
-
- 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
- C07C209/28—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 other reducing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US647,065 | 1976-01-07 | ||
| US05/647,065 US4123462A (en) | 1976-01-07 | 1976-01-07 | Amination process using nickel-rhenium catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1083558A true CA1083558A (en) | 1980-08-12 |
Family
ID=24595557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,485A Expired CA1083558A (en) | 1976-01-07 | 1976-12-22 | Nickel-rhenium hydrogenation catalyst and methods of preparing same and using same |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4123462A (esLanguage) |
| JP (2) | JPS6038380B2 (esLanguage) |
| BE (1) | BE850144A (esLanguage) |
| CA (1) | CA1083558A (esLanguage) |
| DE (1) | DE2700339C3 (esLanguage) |
| FR (1) | FR2337585A1 (esLanguage) |
| GB (1) | GB1569714A (esLanguage) |
| IN (1) | IN145670B (esLanguage) |
| IT (1) | IT1082703B (esLanguage) |
| NL (1) | NL180914C (esLanguage) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11001774B2 (en) | 2016-05-11 | 2021-05-11 | Reg Synthetic Fuels, Llc | Biorenewable kerosene, jet fuel, jet fuel blendstock, and method of manufacturing |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002630B2 (fr) * | 1977-12-12 | 1986-04-16 | Societe Chimique De La Grande Paroisse, Azote Et Produits Chimiques | Catalyseur et procédé de fabrication d'amines à partir d'alcools |
| FR2411030A1 (fr) * | 1977-12-12 | 1979-07-06 | Azote & Prod Chim | Catalyseur et procede de fabrication d'amines a partir d'alcools |
| US4209424A (en) | 1977-12-12 | 1980-06-24 | Societe Chimique de la Grande Paroisse, Azote et Products Chimiques | Catalyst for manufacturing amines from alcohols |
| FR2430262A2 (fr) * | 1978-07-04 | 1980-02-01 | Azote & Prod Chim | Catalyseur et procede de fabrication d'amines a partir d'alcools |
| US4404405A (en) * | 1981-09-30 | 1983-09-13 | Union Carbide Corporation | Process for the preparation of polyethylene polyamines |
| US4400539A (en) * | 1981-09-30 | 1983-08-23 | Union Carbide Corporation | Process for the manufacture of ethylenediamine |
| US4929759A (en) * | 1983-07-27 | 1990-05-29 | Basf Aktiengesellschaft | Production of amines from an olefin and ammonia or a primary or secondary amine |
| SE461095B (sv) * | 1983-09-09 | 1990-01-08 | Berol Kemi Ab | Amineringsfoerfarande med anvaendning av en ruteniumdopad nickel och/eller kovoltkatalysator |
| US4647701A (en) * | 1984-05-23 | 1987-03-03 | Union Carbide Corporation | Processes for producing diethylenetriamine from monoethanolamine |
| US4625030A (en) * | 1984-05-23 | 1986-11-25 | Union Carbide Corporation | Potentiated nickel catalysts for amination |
| US4827037A (en) * | 1985-04-04 | 1989-05-02 | Union Carbide Corporation | Quality of catalytically prepared polyalkylene polyamines |
| US4772750A (en) * | 1985-06-14 | 1988-09-20 | The Dow Chemical Company | Method of producing amines |
| GB8519425D0 (en) * | 1985-08-01 | 1985-09-04 | Ici Plc | Amine production |
| US4709034A (en) * | 1986-02-14 | 1987-11-24 | Air Products And Chemicals, Inc. | Process for the synthesis of hydroxyalkyl amines and hydroxyalkyl piperazines |
| US4918233A (en) * | 1986-07-08 | 1990-04-17 | Air Products And Chemicals, Inc. | Production of ethylenediamine from monoethanolamine and ammonia |
| US4774336A (en) * | 1986-10-02 | 1988-09-27 | Texaco Inc. | Process for preparing N-substituted piperazines from ethylene glycol and amines |
| GB8707304D0 (en) * | 1987-03-26 | 1987-04-29 | Bp Chem Int Ltd | Chemical process |
| US4795733A (en) * | 1987-11-27 | 1989-01-03 | Gaf Corporation | Hydrogenation catalyst and process for its preparation |
| GB8819663D0 (en) * | 1988-08-18 | 1988-09-21 | Bp Chem Int Ltd | Chemical process |
| GB8918965D0 (en) * | 1989-08-19 | 1989-10-04 | Bp Chem Int Ltd | Chemical process |
| DE4006540A1 (de) * | 1990-03-02 | 1991-09-05 | Huels Chemische Werke Ag | Katalysatoren fuer die metathese von olefinen und funktionalisierten olefinen |
| US5321160A (en) * | 1991-07-31 | 1994-06-14 | Tosoh Corporation | Process for producing an ethylenamine |
| US5600000A (en) * | 1993-12-22 | 1997-02-04 | Union Carbide Chemicals & Plastics Technology Corporation | Reductive amination processes for the selective production of amino-ethylethanolamine |
| DE69512381T2 (de) * | 1993-12-22 | 2000-04-06 | Union Carbide Chemicals & Plastics Technology Corp., Danbury | Reduktive Aminierung zur selektiven Herstellung von Aminoethylethanolamin |
| CA2146906C (en) * | 1993-12-22 | 1999-03-16 | Stephen Wayne King | Reductive amination catalysts |
| US5475138A (en) * | 1994-07-07 | 1995-12-12 | Pharm-Eco Laboratories Incorporated | Method preparing amino acid-derived diaminopropanols |
| US5817593A (en) * | 1995-06-02 | 1998-10-06 | The Dow Chemical Company | Catalyst and process for producing amines |
| US6063963A (en) * | 1995-07-05 | 2000-05-16 | Pharm-Eco Laboratories, Inc. | Amino acid-derived diaminopropanols |
| KR19990063939A (ko) * | 1995-10-04 | 1999-07-26 | 그레이스 스티븐 에스. | 아민 캡핑된 폴리에테르 및 이의 제조방법 |
| US5679862A (en) * | 1996-03-25 | 1997-10-21 | Chemical Research & Licensing Company | Amination process |
| SE513250C2 (sv) * | 1997-11-11 | 2000-08-07 | Akzo Nobel Nv | Amineringsförfarande för framställning av polyaminer |
| AU5280999A (en) * | 1998-07-21 | 2000-02-14 | Lonza A.G. | Method for producing amines |
| US6534441B1 (en) * | 1999-03-06 | 2003-03-18 | Union Carbide Chemicals & Plastics Technology Corporation | Nickel-rhenium catalyst for use in reductive amination processes |
| US6309758B1 (en) * | 1999-05-06 | 2001-10-30 | W. R. Grace & Co.-Conn. | Promoted porous catalyst |
| DE10145119A1 (de) * | 2001-09-13 | 2003-04-03 | Basf Ag | Verfahren zur Herstellung von Aminen |
| TWI284200B (en) * | 2002-03-08 | 2007-07-21 | Sensys Medcial Inc | Compact apparatus for noninvasive measurement of glucose through near-infrared spectroscopy |
| US7022645B2 (en) * | 2003-08-04 | 2006-04-04 | Catalytic Distillation Technologies | Ni hydrogenation catalysts, manufacture and use |
| US7131446B2 (en) * | 2004-03-25 | 2006-11-07 | Tang Kenneth Y | Light-triggered tattoo process |
| US20080045749A1 (en) * | 2006-06-07 | 2008-02-21 | The Procter & Gamble Company | Process for the alternating conversion of glycerol to propylene glycol or amino alcohols |
| US7619118B2 (en) | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Process for the conversion of glycerol to propylene glycol and amino alcohols |
| US7619119B2 (en) * | 2006-06-07 | 2009-11-17 | The Procter & Gamble Company | Processes for converting glycerol to amino alcohols |
| WO2009083580A1 (en) * | 2008-01-03 | 2009-07-09 | Akzo Nobel N.V. | Process to prepare ethylene amines |
| US8728430B2 (en) | 2008-06-19 | 2014-05-20 | Honda Motor Co., Ltd. | Low temperature single-wall carbon nanotube synthesis |
| WO2010042164A2 (en) * | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Transalkoxylation of nucleophilic compounds |
| BRPI0914085A2 (pt) * | 2008-10-06 | 2015-10-27 | Dow Global Technologies Llc | processo para a produção de uma ou mais etanolaminas e uma ou mais etilenoaminas e processo para separar uma ou mais alquiletilenodiaminas de etilenodiamina |
| US8618108B2 (en) * | 2008-10-06 | 2013-12-31 | Union Carbide Chemicals & Plastics Technology Llc | Methods of making cyclic, N-amino functional triamines |
| 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 |
| WO2010042158A1 (en) * | 2008-10-06 | 2010-04-15 | Union Carbide Chemicals & Plastics Technology Llc | Method of manufacturing ethyleneamines |
| BRPI0914042A2 (pt) * | 2008-10-06 | 2015-11-03 | Union Carbide Chem Plastic | processo para a produção de uma ou mais etilenoaminas por uma reação de transaminação |
| BRPI0914040A2 (pt) | 2008-10-06 | 2015-11-03 | Union Carbide Chem Plastic | composição de catalisador e método para transaminar um composto reagente |
| CN101875014B (zh) * | 2009-11-17 | 2012-10-03 | 中国科学院大连化学物理研究所 | 一种在临氢条件下一乙醇胺和氨转化为乙二胺的催化剂 |
| US8735616B2 (en) | 2010-05-21 | 2014-05-27 | H R D Corporation | Process for upgrading low value renewable oils |
| DE102011004465A1 (de) | 2010-09-10 | 2012-03-15 | Evonik Degussa Gmbh | Verfahren zur direkten Aminierung sekundärer Alkohole mit Ammoniak zu primären Aminen |
| DE102011075162A1 (de) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Verfahren zur homogen-katalysierte, hochselektiven direkten Aminierung von primären Alkoholen mit Ammoniak zu primären Aminen bei hohem Volumenverhältnis von Flüssig- zu Gasphase und/oder hohen Drücken |
| DE102011003595B4 (de) * | 2011-02-03 | 2014-04-17 | Evonik Degussa Gmbh | Herstellung von in ihrer Hauptkette linearen primären Diaminen für Polyamidsynthesen |
| CA2826415A1 (en) | 2011-02-21 | 2012-08-30 | Evonik Degussa Gmbh | Process for the direct amination of alcohols by means of ammonia to primary amines using a xantphos catalyst system |
| JP6158831B2 (ja) * | 2011-12-22 | 2017-07-05 | ダウ グローバル テクノロジーズ エルエルシー | ジエタノールアミンの還元アミノ化および生じた生成物混合物 |
| US8952198B2 (en) | 2013-01-30 | 2015-02-10 | Ian Williams | Amination process for manufacturing amines using catalyst |
| 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 |
| US10844001B2 (en) | 2016-02-12 | 2020-11-24 | Nouryon Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| JP6671489B2 (ja) * | 2016-02-12 | 2020-03-25 | ヌーリオン ケミカルズ インターナショナル ベスローテン フェノーツハップＮｏｕｒｙｏｎ Ｃｈｅｍｉｃａｌｓ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｂ．Ｖ． | 高級エチレンアミンおよびエチレンアミン誘導体を調製する方法 |
| WO2017137530A1 (en) * | 2016-02-12 | 2017-08-17 | Akzo Nobel Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| CN109996781A (zh) * | 2016-11-30 | 2019-07-09 | 巴斯夫欧洲公司 | 使用沸石催化剂将乙二醇转化为乙二胺的方法 |
| EP3555040A1 (de) | 2016-12-15 | 2019-10-23 | Basf Se | Verfahren zur herstellung von ethanolaminen und/oder ethylenaminen |
| JP7105811B2 (ja) | 2017-06-09 | 2022-07-25 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| WO2018224315A1 (de) | 2017-06-09 | 2018-12-13 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| JP7105812B2 (ja) | 2017-06-09 | 2022-07-25 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| WO2019011708A1 (en) | 2017-07-10 | 2019-01-17 | Akzo Nobel Chemicals International B.V. | PROCESS FOR THE PRODUCTION OF SUPERIOR ETHYLENEAMINES |
| JP7277454B2 (ja) | 2017-10-27 | 2023-05-19 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| CN111278801B (zh) | 2017-10-27 | 2023-05-26 | 巴斯夫欧洲公司 | 从含eda的混合物中分离n-甲基乙二胺 |
| JP7268017B2 (ja) | 2017-10-27 | 2023-05-02 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンアミンの製造方法 |
| WO2019081285A1 (de) | 2017-10-27 | 2019-05-02 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| CN107913694A (zh) * | 2017-10-31 | 2018-04-17 | 山东玉皇化工有限公司 | 一种胺化催化剂载体的调变方法及其应用 |
| CN109734601B (zh) * | 2019-01-25 | 2021-11-12 | 浙江师范大学 | 一种制备1,3-丙二胺的方法 |
| WO2020178085A1 (en) | 2019-03-06 | 2020-09-10 | Basf Se | Method for the production of ethyleneamines |
| WO2021115907A1 (en) | 2019-12-13 | 2021-06-17 | Basf Se | Separation of n-methylethylenediamine from eda-containing mixtures |
| EP4463435A1 (en) | 2022-01-14 | 2024-11-20 | Basf Se | Method for the manufacture or conversion of alkanolamines |
| CN119486997A (zh) | 2022-06-29 | 2025-02-18 | 巴斯夫欧洲公司 | 用于制造亚乙基胺的方法 |
| CN119451938A (zh) | 2022-06-29 | 2025-02-14 | 巴斯夫欧洲公司 | 用于制造亚乙基胺的方法 |
| WO2025125094A1 (en) | 2023-12-14 | 2025-06-19 | Basf Se | Process for preparing diethylenetriamine and/or ethylene glycol |
| 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 |
| WO2026022226A1 (en) | 2024-07-23 | 2026-01-29 | Basf Se | Assistance in controlling a chemical reactor |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240782A (en) * | 1966-03-15 | Method of converting z-dehydro-isoeme tine into z-dehydro-emetine and inter- mediates therein | ||
| DE1034184B (de) * | 1957-01-23 | 1958-07-17 | Basf Ag | Verfahren zur Herstellung von 1, 3-Propylendiamin |
| US3022349A (en) * | 1957-12-30 | 1962-02-20 | Union Carbide Corp | Production of amines |
| NL248643A (esLanguage) * | 1959-02-27 | |||
| DE1172268B (de) * | 1962-02-21 | 1964-06-18 | Basf Ag | Verfahren zur Herstellung von Diaminen |
| FR1360740A (fr) * | 1963-02-12 | 1964-05-15 | British Petroleum Co | Perfectionnements relatifs à l'hydrogénation des paraffines |
| FR1368177A (fr) * | 1963-06-07 | 1964-07-31 | Comp Generale Electricite | Procédé de préparation d'un catalyseur d'hydrogénation, catalyseur ainsi obtenu et applications |
| US3387032A (en) * | 1965-06-08 | 1968-06-04 | Jackson D. Leonard | Process for the manufacture of methylamines |
| US3492314A (en) * | 1965-08-23 | 1970-01-27 | Mitsubishi Petrochemical Co | Process for catalytic hydrogenation of dicarboxylic acid anhydride and catalyst therefor |
| US3520933A (en) * | 1966-10-28 | 1970-07-21 | Basf Ag | Production of amines |
| US3666412A (en) * | 1968-10-21 | 1972-05-30 | Du Pont | Dispersed phase activated and stabilized metal catalysts |
| US3708539A (en) * | 1970-02-06 | 1973-01-02 | Union Oil Co | Condensation of ammonia or a primary or secondary amine with an alcohol |
| BE765482A (fr) * | 1970-04-20 | 1971-08-30 | Du Pont | Catalyseur de reforming modifie au rhenium |
| JPS4734181U (esLanguage) * | 1971-05-07 | 1972-12-16 | ||
| US3739029A (en) * | 1971-12-29 | 1973-06-12 | Shell Oil Co | N-alkyl amine production |
| FR2252330B1 (esLanguage) * | 1973-11-23 | 1978-06-16 | Ruhrchemie Ag | |
| US4036883A (en) * | 1974-11-27 | 1977-07-19 | Basf Aktiengesellschaft | Manufacture of isomer-free 3-methylbutylamine |
-
1976
- 1976-01-07 US US05/647,065 patent/US4123462A/en not_active Expired - Lifetime
- 1976-10-06 US US05/730,291 patent/US4111840A/en not_active Expired - Lifetime
- 1976-12-22 CA CA268,485A patent/CA1083558A/en not_active Expired
-
1977
- 1977-01-05 IT IT67020/77A patent/IT1082703B/it active
- 1977-01-05 DE DE2700339A patent/DE2700339C3/de not_active Expired
- 1977-01-06 FR FR7700256A patent/FR2337585A1/fr active Granted
- 1977-01-06 JP JP52000249A patent/JPS6038380B2/ja not_active Expired
- 1977-01-06 GB GB376/77A patent/GB1569714A/en not_active Expired
- 1977-01-06 BE BE173885A patent/BE850144A/xx not_active IP Right Cessation
- 1977-01-06 NL NLAANVRAGE7700084,A patent/NL180914C/xx not_active IP Right Cessation
- 1977-01-06 IN IN13/CAL/77A patent/IN145670B/en unknown
-
1980
- 1980-12-12 JP JP17480380A patent/JPS56108534A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11001774B2 (en) | 2016-05-11 | 2021-05-11 | Reg Synthetic Fuels, Llc | Biorenewable kerosene, jet fuel, jet fuel blendstock, and method of manufacturing |
| US11236280B2 (en) | 2016-05-11 | 2022-02-01 | Reg Synthetic Fuels, Llc | Biorenewable kerosene, jet fuel, jet fuel blendstock, and method of manufacturing |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6241064B2 (esLanguage) | 1987-09-01 |
| NL7700084A (nl) | 1977-07-11 |
| JPS56108534A (en) | 1981-08-28 |
| JPS6038380B2 (ja) | 1985-08-31 |
| BE850144A (fr) | 1977-07-06 |
| DE2700339C3 (de) | 1980-06-19 |
| GB1569714A (en) | 1980-06-18 |
| FR2337585A1 (fr) | 1977-08-05 |
| DE2700339A1 (de) | 1977-08-18 |
| US4123462A (en) | 1978-10-31 |
| IN145670B (esLanguage) | 1978-11-25 |
| IT1082703B (it) | 1985-05-21 |
| DE2700339B2 (esLanguage) | 1979-08-09 |
| US4111840A (en) | 1978-09-05 |
| JPS5285991A (en) | 1977-07-16 |
| FR2337585B1 (esLanguage) | 1983-10-07 |
| NL180914C (nl) | 1987-05-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1083558A (en) | Nickel-rhenium hydrogenation catalyst and methods of preparing same and using same | |
| CA1241629A (en) | Potentiated nickel catalysts for amination | |
| EP0828558B1 (en) | Catalyst and process for producing amines | |
| EP2340113B1 (en) | Low metal (nickel and rhenium) catalyst compositions including acidic mixed metal oxide as support | |
| US5958825A (en) | Catalysts for the amination of alkylene oxides, alcohols, aldehydes and ketones | |
| US5750790A (en) | Reductive amination catalysts | |
| EP2352585B1 (en) | Low metal loaded, alumina supported, catalyst compositions and amination process | |
| JP5124486B2 (ja) | 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 | |
| US7053247B2 (en) | Process for the manufacture of diethylenetriamine and higher polyethylenepolyamines | |
| US7468342B2 (en) | Catalysts and process for producing aromatic amines | |
| EP0737669B1 (en) | Reductive amination processes for the selective production of aminoethylethanolamine | |
| Barrault et al. | Synthesis of fatty amines. Selectivity control in presence of multifunctional catalysts | |
| JPH0518627B2 (esLanguage) | ||
| EP1385625A2 (en) | A nickel-rhenium catalyst for use in reductive amination processes | |
| CN112898163A (zh) | 一种环己亚胺氨化制备1,6-己二胺的方法 | |
| US4977266A (en) | Aminoethylethanolamine and ethylenediamine producers composition and method for producing same | |
| US5202490A (en) | Process for thr manufacture of diethylenetriamine and aminoethylethanolamine | |
| US5268509A (en) | Process for the preparation of an iron catalyst and a process for the preparation of primary amines by the hydrogenation of nitriles using said iron catalyst | |
| US5600000A (en) | Reductive amination processes for the selective production of amino-ethylethanolamine | |
| US5068329A (en) | Aminoethylethanolamine producers composition and method for producing same | |
| US5068330A (en) | Aminoethyethanolamine and ethylenediamine producers composition and method for producing same | |
| CN110270279B (zh) | 一种用于连续生产二异十三胺的固定床反应器及其应用 | |
| SK135899A3 (en) | Process for the preparation of dicycloaliphatic amines | |
| JPH0260375B2 (esLanguage) | ||
| JPH06182207A (ja) | ニッケル含有触媒の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |