DE1953263C2 - Trägerkatalysator und seine Verwendung zur hydrierenden Aminierung von Alkoholen - Google Patents
Trägerkatalysator und seine Verwendung zur hydrierenden Aminierung von AlkoholenInfo
- Publication number
- DE1953263C2 DE1953263C2 DE19691953263 DE1953263A DE1953263C2 DE 1953263 C2 DE1953263 C2 DE 1953263C2 DE 19691953263 DE19691953263 DE 19691953263 DE 1953263 A DE1953263 A DE 1953263A DE 1953263 C2 DE1953263 C2 DE 1953263C2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- catalyst
- nickel
- alcohols
- cobalt
- 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 description 39
- 150000001298 alcohols Chemical class 0.000 title claims description 11
- 238000005576 amination reaction Methods 0.000 title claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 239000010941 cobalt Substances 0.000 claims description 9
- 229910017052 cobalt Inorganic materials 0.000 claims description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 35
- 150000001412 amines Chemical class 0.000 description 17
- 229910021529 ammonia Inorganic materials 0.000 description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 6
- 239000005751 Copper oxide Substances 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- 229910000428 cobalt oxide Inorganic materials 0.000 description 6
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 6
- 229910000431 copper oxide Inorganic materials 0.000 description 6
- 229910000480 nickel oxide Inorganic materials 0.000 description 6
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- -1 hexanolamine Chemical compound 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QSXLBISEYIUNMB-UHFFFAOYSA-N 2-[(2-methylphenyl)methylamino]-1-[3-(trifluoromethyl)phenyl]ethanol Chemical compound CC1=CC=CC=C1CNCC(O)C1=CC=CC(C(F)(F)F)=C1 QSXLBISEYIUNMB-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- KIVGCURBFFRTJN-UHFFFAOYSA-N 3-[2-[[[2-(4-bromothiophen-2-yl)-2-hydroxyethyl]amino]methyl]phenoxy]-n-[2-(methylamino)-2-oxoethyl]propanamide Chemical compound CNC(=O)CNC(=O)CCOC1=CC=CC=C1CNCC(O)C1=CC(Br)=CS1 KIVGCURBFFRTJN-UHFFFAOYSA-N 0.000 description 1
- DWMVUWJLTQPBBS-UHFFFAOYSA-N 4-(2-cyclohexylpropan-2-yl)cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCCCC1 DWMVUWJLTQPBBS-UHFFFAOYSA-N 0.000 description 1
- QFJYBVLPFAIGBY-UHFFFAOYSA-N 6-(azepan-1-yl)hexan-1-amine Chemical compound NCCCCCCN1CCCCCC1 QFJYBVLPFAIGBY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
-
- 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
- B01J23/72—Copper
-
- 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
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/185—Phosphorus; Compounds thereof with iron group metals or platinum group metals
- B01J27/1853—Phosphorus; Compounds thereof with iron group metals or platinum group metals with iron, cobalt or nickel
-
- 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
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
-
- 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
- B01J23/90—Regeneration or reactivation
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE757840D BE757840A (fr) | 1969-10-23 | Procede de preparation d'amines a partir d'alcools | |
| DE19691953263 DE1953263C2 (de) | 1969-10-23 | 1969-10-23 | Trägerkatalysator und seine Verwendung zur hydrierenden Aminierung von Alkoholen |
| CA095680A CA918678A (en) | 1969-10-23 | 1970-10-15 | Production of amines from alcohols |
| FR7037604A FR2066157A5 (https=) | 1969-10-23 | 1970-10-19 | |
| GB5011870A GB1319495A (en) | 1969-10-23 | 1970-10-22 | Production of amines from alcohols |
| NL7015579A NL7015579A (https=) | 1969-10-23 | 1970-10-23 | |
| US05/391,828 US4014933A (en) | 1969-10-23 | 1973-08-27 | Production of amines from alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691953263 DE1953263C2 (de) | 1969-10-23 | 1969-10-23 | Trägerkatalysator und seine Verwendung zur hydrierenden Aminierung von Alkoholen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1953263A1 DE1953263A1 (de) | 1972-02-17 |
| DE1953263C2 true DE1953263C2 (de) | 1987-01-22 |
Family
ID=5748915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691953263 Expired DE1953263C2 (de) | 1969-10-23 | 1969-10-23 | Trägerkatalysator und seine Verwendung zur hydrierenden Aminierung von Alkoholen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE757840A (https=) |
| CA (1) | CA918678A (https=) |
| DE (1) | DE1953263C2 (https=) |
| FR (1) | FR2066157A5 (https=) |
| GB (1) | GB1319495A (https=) |
| NL (1) | NL7015579A (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2646379C3 (de) * | 1976-10-14 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von N-Alkylanilinen |
| DE2928742A1 (de) * | 1979-07-17 | 1981-02-05 | Bayer Ag | Verfahren zur herstellung von neopentylamin |
| DE3238931A1 (de) * | 1982-10-21 | 1984-04-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 1,3-diamino-2,2-dialkylpropanen |
| JPS62149648A (ja) * | 1985-12-25 | 1987-07-03 | Kao Corp | 第２級アミンの製造方法 |
| DE3605005A1 (de) * | 1986-02-18 | 1987-08-20 | Basf Ag | Verfahren zur herstellung von n-methylpiperazin |
| DE3903367A1 (de) | 1989-02-04 | 1990-08-16 | Basf Ag | Katalysator und verfahren zur hydrierenden aminierung von alkoholen |
| DE4139607A1 (de) * | 1991-11-30 | 1993-06-03 | Basf Ag | Verfahren zur herstellung von n-substituierten lactamen |
| DE4140259A1 (de) * | 1991-12-06 | 1993-06-09 | Basf Ag, 6700 Ludwigshafen, De | Verfahren zur herstellung tertiaerer aminoxide |
| DE4428004A1 (de) | 1994-08-08 | 1996-02-15 | Basf Ag | Verfahren zur Herstellung von Aminen |
| DE4429547A1 (de) * | 1994-08-19 | 1996-02-22 | Basf Ag | Verfahren zur Herstellung von Aminen |
| FR2727679B1 (fr) * | 1994-12-05 | 1997-01-03 | Rhone Poulenc Rorer Sa | Nouveaux agents de transfection et leurs applications pharmaceutiques |
| DE19516940A1 (de) * | 1995-05-09 | 1996-11-14 | Rwe Dea Ag | Herstellung von primären Guerbetaminen |
| DE19742911A1 (de) * | 1997-09-29 | 1999-04-01 | Basf Ag | Verfahren zur Herstellung von Aminen |
| DE19905837A1 (de) * | 1999-02-12 | 2000-08-17 | Basf Ag | Verfahren zur Racemisierung von optisch aktiven Aminen |
| DE50007278D1 (de) | 1999-12-06 | 2004-09-09 | Basf Ag | Verfahren zur Herstellung von Aminen |
| EP1106601B1 (de) | 1999-12-06 | 2004-02-25 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Monoisopropylamin |
| DE10361503A1 (de) | 2003-12-23 | 2005-07-28 | Basf Ag | Verfahren zur Herstellung eines Ethylamins |
| DE102005019373A1 (de) * | 2005-04-26 | 2006-11-02 | Basf Ag | Verfahren zur Herstellung von Ethylenaminen |
| DE102005029932A1 (de) | 2005-06-28 | 2007-01-11 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Polyetheraminen |
| 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 |
| 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 |
| 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 |
| DE102006036220A1 (de) | 2006-08-03 | 2008-02-07 | Clariant International Limited | Polyetheramin-Makromonomere mit zwei benachbarten Hydroxylgruppen und ihre Verwendung zur Herstellung von Polyurethanen |
| MX2009006053A (es) | 2006-12-06 | 2009-06-16 | Clariant Finance Bvi Ltd | Procedimiento para preparar polietetaminas. |
| WO2008138833A1 (de) * | 2007-05-11 | 2008-11-20 | Basf Se | Verfahren zur herstellung von aminen |
| EP2506966B1 (de) | 2009-12-03 | 2017-08-16 | Basf Se | Katalysator und verfahren zur herstellung eines amins |
| WO2011067200A1 (de) | 2009-12-03 | 2011-06-09 | Basf Se | Katalysator und verfahren zur herstellung eines amins |
| US8637668B2 (en) | 2010-06-15 | 2014-01-28 | Basf Se | Process for preparing a cyclic tertiary methylamine |
| US8466322B2 (en) | 2010-06-30 | 2013-06-18 | Basf Se | Process for preparing tri-n-propylamine (TPA) |
| EP2588442B1 (de) | 2010-06-30 | 2014-04-16 | Basf Se | Verfahren zur herstellung von tri-n-propylamin (tpa) |
| DE102010040427A1 (de) | 2010-09-08 | 2012-03-08 | Basf Se | Verfahren zur Herstellung von Mono-n-Octylamin (MOA) |
| US8933223B2 (en) | 2010-10-14 | 2015-01-13 | Basf Se | Process for preparing a cyclic tertiary amine |
| US8766009B2 (en) | 2011-11-21 | 2014-07-01 | Basf Se | Process for preparing ethylamines and monoisopropylamine (MIPA) |
| EP2782898B1 (de) | 2011-11-21 | 2015-10-21 | Basf Se | Verfahren zur herstellung von ethylaminen und mono-iso-propylamin (mipa) |
| US8884015B2 (en) | 2012-06-01 | 2014-11-11 | Basf Se | Process for the preparation of a mono-N-alkypiperazine |
| ES2579088T3 (es) | 2012-06-01 | 2016-08-04 | Basf Se | Proceso para preparar una mono-n-alquil-piperazina |
| WO2013182465A1 (de) | 2012-06-06 | 2013-12-12 | Basf Se | Verfahren zur herstellung von piperazin |
| US8981093B2 (en) | 2012-06-06 | 2015-03-17 | Basf Se | Process for preparing piperazine |
| EP2858978A1 (de) | 2012-06-06 | 2015-04-15 | Basf Se | Verfahren zur herstellung von piperazin |
| CN109678734B (zh) * | 2018-12-27 | 2021-12-21 | 浙江工业大学 | 一种由乙二醇单甲醚直接催化胺化制备2-甲氧基乙胺的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB833589A (en) * | 1956-09-25 | 1960-04-27 | Jefferson Chem Co Inc | Preparation of piperazine |
| US3151115A (en) * | 1961-05-26 | 1964-09-29 | Jefferson Chem Co Inc | Method for the simultaneous production of acyclic and polycyclic amines |
| DE1172268B (de) * | 1962-02-21 | 1964-06-18 | Basf Ag | Verfahren zur Herstellung von Diaminen |
| US3390184A (en) * | 1965-06-01 | 1968-06-25 | Jefferson Chem Co Inc | Production of primary amines by ammonolysis |
| DE1266736B (de) * | 1965-06-19 | 1968-04-25 | Basf Ag | Verfahren zur Herstellung von kobalthaltigen Katalysatoren |
| FR1542024A (fr) * | 1966-10-28 | 1968-10-11 | Basf Ag | Production d'amines |
-
0
- BE BE757840D patent/BE757840A/xx not_active IP Right Cessation
-
1969
- 1969-10-23 DE DE19691953263 patent/DE1953263C2/de not_active Expired
-
1970
- 1970-10-15 CA CA095680A patent/CA918678A/en not_active Expired
- 1970-10-19 FR FR7037604A patent/FR2066157A5/fr not_active Expired
- 1970-10-22 GB GB5011870A patent/GB1319495A/en not_active Expired
- 1970-10-23 NL NL7015579A patent/NL7015579A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1319495A (en) | 1973-06-06 |
| BE757840A (fr) | 1971-04-22 |
| CA918678A (en) | 1973-01-09 |
| FR2066157A5 (https=) | 1971-08-06 |
| DE1953263A1 (de) | 1972-02-17 |
| NL7015579A (https=) | 1971-04-27 |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
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