DE102007041380A1 - Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen - Google Patents
Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen Download PDFInfo
- Publication number
- DE102007041380A1 DE102007041380A1 DE102007041380A DE102007041380A DE102007041380A1 DE 102007041380 A1 DE102007041380 A1 DE 102007041380A1 DE 102007041380 A DE102007041380 A DE 102007041380A DE 102007041380 A DE102007041380 A DE 102007041380A DE 102007041380 A1 DE102007041380 A1 DE 102007041380A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- mass
- barium
- catalyst
- nickel
- 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.)
- Withdrawn
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 89
- 239000003054 catalyst Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 51
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 26
- 150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 50
- 229910052751 metal Inorganic materials 0.000 claims abstract description 31
- 239000002184 metal Substances 0.000 claims abstract description 31
- 239000010949 copper Substances 0.000 claims abstract description 26
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 claims abstract description 23
- 239000011651 chromium Substances 0.000 claims abstract description 22
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 19
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 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 14
- 239000012876 carrier material Substances 0.000 claims abstract description 14
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 14
- 239000010941 cobalt Substances 0.000 claims abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052788 barium Inorganic materials 0.000 claims abstract description 12
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims abstract description 11
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 7
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 34
- 150000001299 aldehydes Chemical class 0.000 claims description 31
- 238000007037 hydroformylation reaction Methods 0.000 claims description 29
- 150000002739 metals Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000001553 barium compounds Chemical class 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001354 calcination Methods 0.000 claims description 5
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims description 4
- MMFCJPPRCYDLLZ-CMDGGOBGSA-N (2E)-dec-2-enal Chemical compound CCCCCCC\C=C\C=O MMFCJPPRCYDLLZ-CMDGGOBGSA-N 0.000 claims description 2
- MMFCJPPRCYDLLZ-UHFFFAOYSA-N dec-2-enal Natural products CCCCCCCC=CC=O MMFCJPPRCYDLLZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 229910052814 silicon oxide Inorganic materials 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- 150000001336 alkenes Chemical class 0.000 description 21
- 239000007791 liquid phase Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 239000007858 starting material Substances 0.000 description 11
- 239000007789 gas Substances 0.000 description 10
- 239000011148 porous material Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 9
- 239000002243 precursor Substances 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IWOUKMZUPDVPGQ-UHFFFAOYSA-N barium nitrate Chemical compound [Ba+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O IWOUKMZUPDVPGQ-UHFFFAOYSA-N 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 4
- -1 alcohol form enol ethers Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000004675 formic acid derivatives Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- JOSWYUNQBRPBDN-UHFFFAOYSA-P ammonium dichromate Chemical compound [NH4+].[NH4+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O JOSWYUNQBRPBDN-UHFFFAOYSA-P 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001845 chromium compounds Chemical class 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- ZCFOBLITZWHNNC-UHFFFAOYSA-N oct-3-en-2-one Chemical compound CCCCC=CC(C)=O ZCFOBLITZWHNNC-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005829 trimerization reaction Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- PYLMCYQHBRSDND-SOFGYWHQSA-N (E)-2-ethyl-2-hexenal Chemical compound CCC\C=C(/CC)C=O PYLMCYQHBRSDND-SOFGYWHQSA-N 0.000 description 1
- 239000001764 (E)-oct-3-en-2-one Substances 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical class CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical class CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 1
- JJMDTERTPNYIGZ-UHFFFAOYSA-N 2-cyclohexylacetaldehyde Chemical compound O=CCC1CCCCC1 JJMDTERTPNYIGZ-UHFFFAOYSA-N 0.000 description 1
- RCBGGJURENJHKV-UHFFFAOYSA-N 2-methylhept-1-ene Chemical compound CCCCCC(C)=C RCBGGJURENJHKV-UHFFFAOYSA-N 0.000 description 1
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical compound CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 1
- GADNZGQWPNTMCH-UHFFFAOYSA-N 2-propylhept-2-enal Chemical compound CCCCC=C(C=O)CCC GADNZGQWPNTMCH-UHFFFAOYSA-N 0.000 description 1
- QDMFTFWKTYXBIW-UHFFFAOYSA-N 3-Methyl-1-heptene Chemical compound CCCCC(C)C=C QDMFTFWKTYXBIW-UHFFFAOYSA-N 0.000 description 1
- PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- RITONZMLZWYPHW-UHFFFAOYSA-N 3-methylhex-1-ene Chemical compound CCCC(C)C=C RITONZMLZWYPHW-UHFFFAOYSA-N 0.000 description 1
- XZJZVNABSFJYOK-UHFFFAOYSA-N 3-methylidenenonane Chemical compound CCCCCCC(=C)CC XZJZVNABSFJYOK-UHFFFAOYSA-N 0.000 description 1
- GLUPFQMLFXGTNL-UHFFFAOYSA-N 3-methyloct-1-ene Chemical compound CCCCCC(C)C=C GLUPFQMLFXGTNL-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-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
- 238000007696 Kjeldahl method Methods 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000006668 aldol addition reaction Methods 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- PWHCIQQGOQTFAE-UHFFFAOYSA-L barium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ba+2] PWHCIQQGOQTFAE-UHFFFAOYSA-L 0.000 description 1
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 1
- QOWZHEWZFLTYQP-UHFFFAOYSA-K chromium(3+);triformate Chemical compound [Cr+3].[O-]C=O.[O-]C=O.[O-]C=O QOWZHEWZFLTYQP-UHFFFAOYSA-K 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- XEHUIDSUOAGHBW-UHFFFAOYSA-N chromium;pentane-2,4-dione Chemical compound [Cr].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O XEHUIDSUOAGHBW-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- PFQLIVQUKOIJJD-UHFFFAOYSA-L cobalt(ii) formate Chemical compound [Co+2].[O-]C=O.[O-]C=O PFQLIVQUKOIJJD-UHFFFAOYSA-L 0.000 description 1
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 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
- 239000000543 intermediate Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 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
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N propyl ethylene Natural products CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003284 rhodium compounds Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 150000003388 sodium compounds Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 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
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/26—Chromium
-
- 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
- B01J23/78—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 alkali- or alkaline earth metals
-
- 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
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0207—Pretreatment of the support
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
- C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- 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
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/866—Nickel and chromium
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/635—0.5-1.0 ml/g
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007041380A DE102007041380A1 (de) | 2007-08-31 | 2007-08-31 | Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen |
| US12/674,910 US20110060169A1 (en) | 2007-08-31 | 2008-07-07 | Hydrogenation catalyst and process for preparing alcohols by hydrogenation of carbonyl compounds |
| KR1020107004442A KR101518083B1 (ko) | 2007-08-31 | 2008-07-07 | 수소화 촉매 및 카르보닐 화합물의 수소화에 의한 알콜의 제조 방법 |
| PCT/EP2008/058780 WO2009027135A1 (de) | 2007-08-31 | 2008-07-07 | Hydrierkatalysator und verfahren zur herstellung von alkoholen durch hydrierung von carbonylverbindungen |
| EP08774833.1A EP2180947B1 (de) | 2007-08-31 | 2008-07-07 | Hydrierkatalysator und verfahren zur herstellung von alkoholen durch hydrierung von carbonylverbindungen |
| ES08774833.1T ES2476606T3 (es) | 2007-08-31 | 2008-07-07 | Procedimiento para la preparación de alcoholes por hidrogenación de compuestos carbon�licos |
| JP2010522280A JP5564714B2 (ja) | 2007-08-31 | 2008-07-07 | 水素化触媒、及びカルボニル化合物の水素化によるアルコールの製造法 |
| TW097132379A TWI503170B (zh) | 2007-08-31 | 2008-08-25 | 氫化觸媒及藉由羰基化合物之氫化而製造醇類的方法 |
| ARP080103756A AR068199A1 (es) | 2007-08-31 | 2008-08-29 | Catalizador de hidrogenacion y procedimiento para preparar alcoholes por hidrogenacion de compuestos de carbonilo |
| CN200810215488.4A CN101376104B (zh) | 2007-08-31 | 2008-08-29 | 氢化催化剂和通过氢化羰基化合物而制备醇的方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007041380A DE102007041380A1 (de) | 2007-08-31 | 2007-08-31 | Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102007041380A1 true DE102007041380A1 (de) | 2009-03-05 |
Family
ID=39817112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102007041380A Withdrawn DE102007041380A1 (de) | 2007-08-31 | 2007-08-31 | Hydrierkatalysator und Verfahren zur Herstellung von Alkoholen durch Hydrierung von Carbonylverbindungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20110060169A1 (https=) |
| EP (1) | EP2180947B1 (https=) |
| JP (1) | JP5564714B2 (https=) |
| KR (1) | KR101518083B1 (https=) |
| CN (1) | CN101376104B (https=) |
| AR (1) | AR068199A1 (https=) |
| DE (1) | DE102007041380A1 (https=) |
| ES (1) | ES2476606T3 (https=) |
| TW (1) | TWI503170B (https=) |
| WO (1) | WO2009027135A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011045102A1 (de) | 2009-10-15 | 2011-04-21 | Evonik Oxeno Gmbh | Verfahren zur herstellung von decanolen durch hydrierung von decenalen |
| DE102012105878A1 (de) | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Isopentanderivaten |
| DE102013113724A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten alpha, beta-ungesättigter Decenale aus Propylen |
| DE102013113719A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten α,β-ungesättigter Decenale |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
| DE102009001594A1 (de) | 2009-03-17 | 2010-09-30 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von alpha, beta-ungesättigten C10-Aldehyden |
| DE102009027406A1 (de) | 2009-07-01 | 2011-01-05 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von geruchsarmen n-Butan |
| DE102009028975A1 (de) | 2009-08-28 | 2011-03-03 | Evonik Oxeno Gmbh | Esterderivate der 2,5-Furandicarbonsäure und ihre Verwendung als Weichmacher |
| DE102009045139A1 (de) | 2009-09-30 | 2011-03-31 | Evonik Oxeno Gmbh | Herstellung von alpha,beta-ungesättigten Aldehyden mittels einer Reaktionsmischpumpe |
| DE102010029924A1 (de) | 2010-06-10 | 2011-12-15 | Evonik Oxeno Gmbh | Verfahren zur Regenerierung von gebrauchten Hydrierkatalysatoren |
| DE102011005608A1 (de) | 2011-03-16 | 2012-09-20 | Evonik Oxeno Gmbh | Mischoxidzusammensetzungen und Verfahren zur Herstellung von Isoolefinen |
| CN103030528B (zh) * | 2011-09-29 | 2015-08-12 | 中国石油化工股份有限公司 | 苯甲醛液相加氢制备苯甲醇 |
| US9233899B2 (en) | 2011-12-22 | 2016-01-12 | Celanese International Corporation | Hydrogenation catalysts having an amorphous support |
| US9000234B2 (en) | 2011-12-22 | 2015-04-07 | Celanese International Corporation | Calcination of modified support to prepare hydrogenation catalysts |
| US9333496B2 (en) | 2012-02-29 | 2016-05-10 | Celanese International Corporation | Cobalt/tin catalyst for producing ethanol |
| US9079172B2 (en) | 2012-03-13 | 2015-07-14 | Celanese International Corporation | Promoters for cobalt-tin catalysts for reducing alkanoic acids |
| US9024086B2 (en) | 2012-01-06 | 2015-05-05 | Celanese International Corporation | Hydrogenation catalysts with acidic sites |
| US8981164B2 (en) | 2012-01-06 | 2015-03-17 | Celanese International Corporation | Cobalt and tin hydrogenation catalysts |
| CN104039448B (zh) | 2012-01-06 | 2016-11-16 | 国际人造丝公司 | 具有钴改性载体的加氢催化剂 |
| US9050585B2 (en) | 2012-02-10 | 2015-06-09 | Celanese International Corporation | Chemisorption of ethyl acetate during hydrogenation of acetic acid to ethanol |
| US8772553B2 (en) | 2012-10-26 | 2014-07-08 | Celanese International Corporation | Hydrogenation reaction conditions for producing ethanol |
| US8853469B2 (en) | 2012-11-20 | 2014-10-07 | Celanese International Corporation | Combined column for separating products of different hydrogenation reactors |
| US8729318B1 (en) | 2012-11-20 | 2014-05-20 | Celanese International Corporation | Process for producing ethanol from methyl acetate |
| DE102013203117A1 (de) * | 2013-02-26 | 2014-08-28 | Evonik Industries Ag | Optimierte Trenntechnik zur Aufarbeitung von homogen katalysierten Hydroformylierungsmischungen |
| CN104513131B (zh) * | 2013-09-30 | 2017-08-22 | 中国石油化工股份有限公司 | 癸烯醛液相加氢制备癸醇的方法 |
| US9353035B2 (en) | 2014-04-28 | 2016-05-31 | Celanese International Corporation | Process for producing ethanol with zonal catalysts |
| US9073815B1 (en) | 2014-04-28 | 2015-07-07 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide and processes for producing ethanol |
| US9382177B2 (en) | 2014-04-28 | 2016-07-05 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide comprising a promoter metal |
| US9024088B1 (en) | 2014-04-28 | 2015-05-05 | Celanese International Corporation | Hydrogenation catalysts comprising a mixed oxide comprising nickel |
| EP3037400B1 (de) | 2014-12-23 | 2018-08-01 | Evonik Degussa GmbH | Chromfreie hydrierung von hydroformylierungsgemischen |
| CN106179373A (zh) * | 2015-05-07 | 2016-12-07 | 中国石油化工股份有限公司 | 一种用于癸烯醛液相加氢制异癸醇的催化剂及其制备方法 |
| CN106008156A (zh) * | 2016-05-19 | 2016-10-12 | 山东成泰化工有限公司 | 一种癸醇的制备方法 |
| CN105884575A (zh) * | 2016-05-24 | 2016-08-24 | 山东成泰化工有限公司 | 一种利用正戊醛制备戊醇的方法 |
| RU2625452C1 (ru) * | 2016-06-24 | 2017-07-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Иркутский государственный университет" (ФГБОУ ВО "ИГУ") | Никелевый катализатор гидрирования аренов |
| CN106083527A (zh) * | 2016-06-27 | 2016-11-09 | 山东成泰化工有限公司 | 一种戊醇的制备方法 |
| CN106111184A (zh) * | 2016-06-27 | 2016-11-16 | 山东成泰化工有限公司 | 一种异癸醇制备用催化剂及其制备方法 |
| CN106187682A (zh) * | 2016-06-27 | 2016-12-07 | 山东成泰化工有限公司 | 一种癸醇的制备方法 |
| US11673125B2 (en) | 2016-08-18 | 2023-06-13 | The University Of Chicago | Metal oxide-supported earth-abundant metal catalysts for highly efficient organic transformations |
| US10245578B2 (en) | 2016-11-09 | 2019-04-02 | Evonik Degussa Gmbh | Chromium- and nickel-free hydrogenation of hydroformylation mixtures |
| KR101884928B1 (ko) * | 2017-03-28 | 2018-08-30 | 금호석유화학 주식회사 | 금속산화물 촉매, 그 제조방법, 및 이를 이용한 알코올의 제조방법 |
| FR3065175A1 (fr) * | 2017-04-14 | 2018-10-19 | IFP Energies Nouvelles | Procede de transformation d'alcools par des catalyseurs solides a base de cuivre et d'un element choisi parmi na, ca, ba et k |
| CN107020102B (zh) * | 2017-04-26 | 2019-05-31 | 浙江大学 | 一种镍-铬酸镁催化剂及其制备方法以及在甘油制备乙醇中的应用 |
| CN107011107A (zh) * | 2017-05-16 | 2017-08-04 | 中国科学技术大学 | 一种采用负载型金属催化剂制备醇的方法 |
| RU2020123756A (ru) | 2017-12-20 | 2022-01-20 | Басф Се | Катализатор и способ получения диметилового эфира |
| GB201814682D0 (en) | 2018-09-10 | 2018-10-24 | Johnson Matthey Davy Technologies Ltd | Process for the activation of oxidised catalysts |
| CN111215081A (zh) * | 2018-11-26 | 2020-06-02 | 中国科学院大连化学物理研究所 | 一种醛类加氢制醇类催化剂及其制备方法 |
| EP4021885B1 (de) | 2019-08-30 | 2024-06-12 | Covestro Deutschland AG | Verfahren zur hydrierung von aromatischen nitroverbindungen |
| US20240157343A1 (en) | 2021-03-01 | 2024-05-16 | Covestro Deutschland Ag | Method for the hydrogenation of aromatic nitro compounds |
| CN112979416A (zh) * | 2021-03-09 | 2021-06-18 | 浙江建业化工股份有限公司 | 一种高选择性甲基异丁基醇的制备方法 |
| CN117800811A (zh) * | 2022-09-30 | 2024-04-02 | 中国科学院大连化学物理研究所 | 一种3-龙脑烯基-2-丁醇的制备方法 |
| CN117534541A (zh) * | 2023-11-14 | 2024-02-09 | 山东京博石油化工有限公司 | 一种c12醇及其制备方法 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809220A (en) | 1954-05-11 | 1957-10-08 | Exxon Research Engineering Co | Hydrogenation of oxo aldehydes in the presence of sulfactive catalysts and water |
| US4401834A (en) | 1982-06-01 | 1983-08-30 | Exxon Research & Engineering Co. | Process for producing alcohols |
| GB2142010A (en) | 1983-06-23 | 1985-01-09 | Exxon Research Engineering Co | Process for production of aliphatic alcohols |
| US5059710A (en) | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| DE19842370A1 (de) | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur selektiven Hydrierung von Hydroformylierungsgemischen |
| DE19933348A1 (de) | 1999-07-16 | 2001-02-08 | Oxeno Olefinchemie Gmbh | Verfahren zur Reduzierung oxidischer Hydrierkontakte |
| WO2001087809A1 (de) | 2000-05-18 | 2001-11-22 | Basf Aktiengesellschaft | Verfahren zur herstellung von gesättigten c3-c20-alkoholen |
| DE10062448A1 (de) | 2000-12-14 | 2002-06-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Hydroformylierungsgemischen |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795600A (en) * | 1954-06-25 | 1957-06-11 | Union Carbide & Carbon Corp | Production of nitriles |
| US3781406A (en) * | 1971-07-07 | 1973-12-25 | Monsanto Co | Process of treating auto exhaust with shrinkage resistant copper aluminaterare earth catalysts |
| US3894140A (en) * | 1973-05-09 | 1975-07-08 | Chemical Construction Corp | Stabilization of alumina catalyst supports |
| US4666879A (en) * | 1985-09-11 | 1987-05-19 | Harshaw/Filtrol Partnership | Extruded copper chromite-alumina hydrogenation catalyst |
| US5124295A (en) * | 1990-12-13 | 1992-06-23 | Engelhard Corporation | Copper chromite catalyst and process for preparation said catalyst |
| DE4243722A1 (de) * | 1992-12-23 | 1994-06-30 | Basf Ag | Verfahren zur Herstellung von Polyetherglykolen |
| CN1100029C (zh) * | 1994-05-19 | 2003-01-29 | 巴福斯股份公司 | 催化剂、其制备方法和应用 |
| US5962741A (en) * | 1996-11-19 | 1999-10-05 | Novartis Ag | Process for the production of aromatic halogen-amino compounds |
| DE19842369A1 (de) * | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur Hydrierung von Hydroformylierungsgemischen |
| DE19905838A1 (de) * | 1999-02-12 | 2000-08-17 | Basf Ag | Verfahren zur Racemisierung von optisch aktiven Aminen |
| US6255358B1 (en) * | 2000-03-17 | 2001-07-03 | Energy International Corporation | Highly active Fischer-Tropsch synthesis using doped, thermally stable catalyst support |
| DE10222850B4 (de) * | 2001-05-30 | 2013-07-18 | Daicel Chemical Industries, Ltd. | Verfahren zur Herstellung eines alicyclischen ungesättigten Alkohols |
| GB0119327D0 (en) * | 2001-08-08 | 2001-10-03 | Johnson Matthey Plc | Catalyst |
| DE10220799A1 (de) * | 2002-05-10 | 2003-12-11 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von C13-Alkoholgemischen |
| DE10225565A1 (de) * | 2002-06-10 | 2003-12-18 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| DE10232868A1 (de) * | 2002-07-19 | 2004-02-05 | Oxeno Olefinchemie Gmbh | Feinporiger Katalysator und Verfahren zur Hydrierung von aromatischen Verbindungen |
| WO2005041409A2 (en) * | 2003-10-23 | 2005-05-06 | Koninklijke Philips Electronics N.V. | Switch |
| DE102004021128A1 (de) * | 2004-04-29 | 2005-11-24 | Oxeno Olefinchemie Gmbh | Vorrichtung und Verfahren für die kontinuierliche Umsetzung einer Flüssigkeit mit einem Gas an einem festen Katalysator |
| DE102004055189B4 (de) * | 2004-11-16 | 2007-02-08 | Süd-Chemie AG | Verfahren zur Hydrierung von Acetophenon |
| DE102004059292A1 (de) * | 2004-12-09 | 2006-06-14 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Alkoholen aus Olefinen durch Hydroformylierung und Hydrierung |
| DE102004063673A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur kontinuierlichen katalytischen Hydrierung von hydrierbaren Verbindungen an festen, im Festbett angeordneten Katalysatoren mit einem wasserstoffhaltigen Gas |
| DE102004063637A1 (de) * | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
| DE102005035816A1 (de) * | 2005-07-30 | 2007-02-01 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Oxo-Aldehyden mit hohen Estergehalten |
| WO2007028411A1 (en) * | 2005-09-08 | 2007-03-15 | Evonik Degussa Gmbh | The production and use of supported activated base metal catalysts for organic transformation |
| DE102006040432A1 (de) * | 2006-08-29 | 2008-03-20 | Oxeno Olefinchemie Gmbh | Katalysator und Verfahren zur Herstellung von Isoolefinen |
-
2007
- 2007-08-31 DE DE102007041380A patent/DE102007041380A1/de not_active Withdrawn
-
2008
- 2008-07-07 EP EP08774833.1A patent/EP2180947B1/de not_active Not-in-force
- 2008-07-07 ES ES08774833.1T patent/ES2476606T3/es active Active
- 2008-07-07 KR KR1020107004442A patent/KR101518083B1/ko not_active Expired - Fee Related
- 2008-07-07 US US12/674,910 patent/US20110060169A1/en not_active Abandoned
- 2008-07-07 WO PCT/EP2008/058780 patent/WO2009027135A1/de not_active Ceased
- 2008-07-07 JP JP2010522280A patent/JP5564714B2/ja not_active Expired - Fee Related
- 2008-08-25 TW TW097132379A patent/TWI503170B/zh not_active IP Right Cessation
- 2008-08-29 AR ARP080103756A patent/AR068199A1/es unknown
- 2008-08-29 CN CN200810215488.4A patent/CN101376104B/zh not_active Expired - Fee Related
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2809220A (en) | 1954-05-11 | 1957-10-08 | Exxon Research Engineering Co | Hydrogenation of oxo aldehydes in the presence of sulfactive catalysts and water |
| US4401834A (en) | 1982-06-01 | 1983-08-30 | Exxon Research & Engineering Co. | Process for producing alcohols |
| GB2142010A (en) | 1983-06-23 | 1985-01-09 | Exxon Research Engineering Co | Process for production of aliphatic alcohols |
| US5059710A (en) | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| DE19842370A1 (de) | 1998-09-16 | 2000-03-23 | Oxeno Oelfinchemie Gmbh | Verfahren zur selektiven Hydrierung von Hydroformylierungsgemischen |
| DE19933348A1 (de) | 1999-07-16 | 2001-02-08 | Oxeno Olefinchemie Gmbh | Verfahren zur Reduzierung oxidischer Hydrierkontakte |
| WO2001087809A1 (de) | 2000-05-18 | 2001-11-22 | Basf Aktiengesellschaft | Verfahren zur herstellung von gesättigten c3-c20-alkoholen |
| DE10062448A1 (de) | 2000-12-14 | 2002-06-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Hydrierung von Hydroformylierungsgemischen |
Non-Patent Citations (3)
| Title |
|---|
| J. Falbe, a. a. O., Kirk-Othmer, a. a. O., 164, 175 |
| J. Falbe, New Syntheses with Carbon Monoxide, Springer-Verlag, Heidelberg-New York, 1980, Seite 99 ff. |
| Kirk-Othmer, Encyclopedia of Chemical Technology, Band 17, 4. Auflage, John Wiley & Sons, Seiten 902 bis 919 (1996) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011045102A1 (de) | 2009-10-15 | 2011-04-21 | Evonik Oxeno Gmbh | Verfahren zur herstellung von decanolen durch hydrierung von decenalen |
| DE102009045718A1 (de) | 2009-10-15 | 2011-04-21 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Decanolen durch Hydrierung von Decenalen |
| US8455701B2 (en) | 2009-10-15 | 2013-06-04 | Evonik Oxeno Gmbh | Method for producing decanols by means of hydrogenating decenals |
| DE102012105878A1 (de) | 2012-07-02 | 2014-01-02 | Oxea Gmbh | Verfahren zur Herstellung von Isopentanderivaten |
| WO2014005975A1 (de) | 2012-07-02 | 2014-01-09 | Oxea Gmbh | Verfahren zur herstellung von isopentanderivaten |
| DE102013113724A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten alpha, beta-ungesättigter Decenale aus Propylen |
| DE102013113719A1 (de) | 2013-12-09 | 2015-06-11 | Oxea Gmbh | Verfahren zur Herstellung von Pentanderivaten und Derivaten α,β-ungesättigter Decenale |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010536569A (ja) | 2010-12-02 |
| TWI503170B (zh) | 2015-10-11 |
| ES2476606T3 (es) | 2014-07-15 |
| CN101376104B (zh) | 2014-08-20 |
| EP2180947B1 (de) | 2014-04-23 |
| TW200927284A (en) | 2009-07-01 |
| WO2009027135A1 (de) | 2009-03-05 |
| JP5564714B2 (ja) | 2014-08-06 |
| EP2180947A1 (de) | 2010-05-05 |
| AR068199A1 (es) | 2009-11-11 |
| KR20100046234A (ko) | 2010-05-06 |
| CN101376104A (zh) | 2009-03-04 |
| KR101518083B1 (ko) | 2015-05-06 |
| US20110060169A1 (en) | 2011-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2180947B1 (de) | Hydrierkatalysator und verfahren zur herstellung von alkoholen durch hydrierung von carbonylverbindungen | |
| EP0987241B1 (de) | Verfahren zur selektiven Hydrierung von Hydroformylierungsgemischen | |
| EP3037400B1 (de) | Chromfreie hydrierung von hydroformylierungsgemischen | |
| EP1219584B1 (de) | Verfahren zur Hydrierung von Hydroformylierungsgemischen | |
| EP0987242B1 (de) | Verfahren zur Herstellung von höheren Oxo-Alkoholen aus Olefingemsichen | |
| EP1749572B1 (de) | Verfahren zur hydrierung von oxo-aldehyden mit hohen estergehalten | |
| EP0987243B1 (de) | Verfahren zur Herstellung von höheren Oxo-Alkoholen aus Olefingemischen durch zweistufige Hydroformylierung | |
| EP1669337B1 (de) | Verfahren zur Herstellung von Alkoholen aus Olefinen durch Hydroformylierung und Hydrierung | |
| EP1713749B1 (de) | Verfahren zur herstellung von olefinen mit 8 bis 12 kohlenstoffatomen | |
| EP1231194B1 (de) | Herstellung von 1-Olefinen | |
| DE102009045718A1 (de) | Verfahren zur Herstellung von Decanolen durch Hydrierung von Decenalen | |
| EP2872467B1 (de) | Isononylamine ausgehend von 2-ethylhexanol, verfahren zu ihrer herstellung | |
| DE102008007080A1 (de) | Verfahren zur Herstellung von C9-Alkohol aus C8-Olefinen | |
| DE102009027978A1 (de) | Verfahren zur Herstellung von Decancarbonsäuren | |
| EP2285488B1 (de) | Verfahren zur herstellung von gesättigten ethern durch hydrierung ungesättigter ether | |
| EP0888273B1 (de) | Verfahren zur dehydrierung von sekundären cyclischen alkoholen | |
| EP0295435A2 (de) | Verfahren zur Herstellung von Alkanolen aus Alkinolen | |
| DE10227995A1 (de) | Verfahren zur Hydroformylierung von Olefinen | |
| DE102008002201A1 (de) | Verfahren zur Herstellung von Alkoholen aus Hydroformylierungsgemischen | |
| DE1913198B2 (https=) | ||
| DE10326237A1 (de) | Verfahren zur Gewinnung von Alkoholen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R081 | Change of applicant/patentee |
Owner name: EVONIK DEGUSSA GMBH, DE Free format text: FORMER OWNER: EVONIK OXENO GMBH, 45772 MARL, DE Effective date: 20130905 |
|
| R005 | Application deemed withdrawn due to failure to request examination | ||
| R005 | Application deemed withdrawn due to failure to request examination |
Effective date: 20140902 |