BE358033A - - Google Patents

Info

Publication number

BE358033A

BE358033A BE358033DA BE358033A BE 358033 A BE358033 A BE 358033A BE 358033D A BE358033D A BE 358033DA BE 358033 A BE358033 A BE 358033A

Authority

BE

Belgium

Prior art keywords

hydrogen

cobalt

alcohols

aldehydes

mixture

Prior art date

Links

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• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 15
• 239000003054 catalyst Substances 0.000 claims description 13
• 239000000203 mixture Substances 0.000 claims description 13
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 10
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
• 229910017052 cobalt Inorganic materials 0.000 claims description 8
• 239000010941 cobalt Substances 0.000 claims description 8
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
• 229910052802 copper Inorganic materials 0.000 claims description 8
• 239000010949 copper Substances 0.000 claims description 8
• -1 aliphatic aldehydes Chemical class 0.000 claims description 5
• 238000009833 condensation Methods 0.000 claims description 5
• 230000005494 condensation Effects 0.000 claims description 5
• 150000003138 primary alcohols Chemical class 0.000 claims description 5
• 239000011787 zinc oxide Substances 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 3
• 238000003786 synthesis reaction Methods 0.000 claims description 3
• WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 2
• 230000003197 catalytic effect Effects 0.000 claims description 2
• 229910000423 chromium oxide Inorganic materials 0.000 claims 1
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
• 150000001299 aldehydes Chemical class 0.000 description 11
• 235000019441 ethanol Nutrition 0.000 description 11
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
• 150000001298 alcohols Chemical class 0.000 description 8
• 238000006243 chemical reaction Methods 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
• 229910000831 Steel Inorganic materials 0.000 description 5
• 239000010959 steel Substances 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
• 239000007789 gas Substances 0.000 description 4
• 229910052725 zinc Inorganic materials 0.000 description 4
• UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 3
• 229910001981 cobalt nitrate Inorganic materials 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 229910052759 nickel Inorganic materials 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
• 239000010425 asbestos Substances 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 229910052804 chromium Inorganic materials 0.000 description 2
• 239000011651 chromium Substances 0.000 description 2
• 239000004927 clay Substances 0.000 description 2
• XTUHPOUJWWTMNC-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)chromium Chemical compound [Co+2].[O-][Cr]([O-])(=O)=O XTUHPOUJWWTMNC-UHFFFAOYSA-N 0.000 description 2
• 229940116318 copper carbonate Drugs 0.000 description 2
• GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 2
• 229910052748 manganese Inorganic materials 0.000 description 2
• 239000011572 manganese Substances 0.000 description 2
• 229910052895 riebeckite Inorganic materials 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 2
• OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
• DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 150000001241 acetals Chemical class 0.000 description 1
• 239000000956 alloy Substances 0.000 description 1
• 229910045601 alloy Inorganic materials 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 229910002090 carbon oxide Inorganic materials 0.000 description 1
• 238000006555 catalytic reaction Methods 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000001627 detrimental effect Effects 0.000 description 1
• NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 125000005909 ethyl alcohol group Chemical group 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 238000004508 fractional distillation Methods 0.000 description 1
• AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• 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 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 150000002828 nitro derivatives Chemical class 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000007086 side reaction Methods 0.000 description 1
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
• 239000006104 solid solution Substances 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1