DEF0008772MA - - Google Patents
Info
- Publication number
- DEF0008772MA DEF0008772MA DEF0008772MA DE F0008772M A DEF0008772M A DE F0008772MA DE F0008772M A DEF0008772M A DE F0008772MA
- Authority
- DE
- Germany
- Prior art keywords
- crotonaldehyde
- butyraldehyde
- nickel
- carried out
- hydrogenation
- 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.)
- Active
Links
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 20
- MLUCVPSAIODCQM-NSCUHMNNSA-N Crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 229910000480 nickel oxide Inorganic materials 0.000 claims description 11
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 claims description 11
- 238000005984 hydrogenation reaction Methods 0.000 claims description 8
- 239000005751 Copper oxide Substances 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QPLDLSVMHZLSFG-UHFFFAOYSA-N copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000008262 pumice Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N Nickel(II) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 load Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- -1 silicon-oxygen compounds Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2628987C3 (de) | Verfahren zur Herstellung von C↓3↓-C↓5↓-Alkanolen | |
| EP0071787B1 (de) | Neue Ruthenium/Kohle-Hydrierkatalysatoren, deren Herstellung und Verwendung zur selektiven Hydrierung von ungesättigten Carbonylverbindungen | |
| DE2525506C2 (de) | Verfahren zur Herstellung eines Nickel und/oder Kobalt und Zinkoxid enthaltenden Katalysators | |
| DE69005777T2 (de) | Hydrogenation von Citral. | |
| DE2431929A1 (de) | Katalysator zur partiellen hydrierung | |
| EP0008022B1 (de) | Verfahren zur Herstellung von gesättigten aliphatischen, cycloaliphatischen und araliphatischen Aldehyden | |
| EP0024648B1 (de) | Verfahren zur Herstellung von ungesättigten Alkoholen | |
| EP0922687B1 (de) | Verfahren zur Herstellung von Alkoholen | |
| DE2926641C2 (de) | Molybdän enthaltender Raney-Nickel-Katalysator und seine Verwendung zur katalytischen Hydrierung von Butindiol | |
| EP1106597A1 (de) | Verfahren zur Herstellung von Ketonen, insbesondere von 6-Methylheptan-2-On | |
| EP0013385B1 (de) | Verfahren zur Herstellung von aliphatischen Carbonylverbindungen | |
| EP0082935A1 (de) | Verfahren zur kontinuierlichen Herstellung von n-Butyraldehyd durch selektive Hydrierung von Crotonaldehyd in flüssiger Phase in Gegenwart eines Palladium-Aluminiumoxid-Katalysators | |
| DE3103268C2 (de) | 2-Methylen-3-benzyl-butanal, 2-Methyl-3-benzyl-butanal, 2-Methyl-3-benzyl-butanol und ihre Verwendung als Riechstoffe | |
| DEF0008772MA (US07923587-20110412-C00001.png) | ||
| EP0767769A1 (de) | Verfahren zur herstellung von 1,4-butandiol | |
| DE3246978A1 (de) | Verfahren zur herstellung von aminen | |
| EP0211205B1 (de) | Verfahren zur Herstellung von 2-Methyl-2-alkenalen | |
| DE950908C (de) | Verfahren zur Herstellung von Butyraldehyd | |
| DE2327510B2 (de) | Verfahren zur Herstellung von Dimethylalkylaminen aus Aldehyd-Ammoniak-Verbindungen | |
| DE1280835B (de) | Verfahren zur Herstellung von Dihydrozimtaldehyden | |
| DE1518991A1 (de) | Verfahren zur Herstellung von Carbonylverbindungen | |
| DE858247C (de) | Verfahren zur Herstellung von ungesaettigten Alkoholen aus ungesaettigten Aldehyden oder Ketonen durch Hydrierung in Gegenwart von Cadmium unter erhoehtem Druck | |
| DE898739C (de) | Verfahren zum Herstellen von ungesaettigten Aldehyden | |
| DE862016C (de) | Verfahren zur Herstellung von Tetrahydropyranderivaten | |
| DE1115232B (de) | Verfahren zur Herstellung von Alkoholen durch Hydrierung von Aldehyden |
