JP6494795B2 - 炭水化物源からエチレングルコールを製造する方法 - Google Patents
炭水化物源からエチレングルコールを製造する方法 Download PDFInfo
- Publication number
- JP6494795B2 JP6494795B2 JP2017555202A JP2017555202A JP6494795B2 JP 6494795 B2 JP6494795 B2 JP 6494795B2 JP 2017555202 A JP2017555202 A JP 2017555202A JP 2017555202 A JP2017555202 A JP 2017555202A JP 6494795 B2 JP6494795 B2 JP 6494795B2
- Authority
- JP
- Japan
- Prior art keywords
- metal
- tungsten
- carbohydrate source
- catalyst system
- group
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 145
- 150000001720 carbohydrates Chemical class 0.000 title claims description 98
- 238000000034 method Methods 0.000 title claims description 60
- 235000014633 carbohydrates Nutrition 0.000 claims description 97
- 229910052751 metal Inorganic materials 0.000 claims description 69
- 239000002184 metal Substances 0.000 claims description 69
- 239000003054 catalyst Substances 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 54
- -1 tungstate compound Chemical class 0.000 claims description 50
- 239000003085 diluting agent Substances 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 28
- 150000003658 tungsten compounds Chemical class 0.000 claims description 28
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 26
- 229910052707 ruthenium Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 23
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052721 tungsten Inorganic materials 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000010937 tungsten Substances 0.000 claims description 21
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
- 150000002972 pentoses Chemical class 0.000 claims description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 15
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 15
- 239000008103 glucose Substances 0.000 claims description 15
- 150000002402 hexoses Chemical class 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 10
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 9
- 229920002472 Starch Polymers 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 235000019698 starch Nutrition 0.000 claims description 8
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 239000008107 starch Substances 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 238000010533 azeotropic distillation Methods 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 229910001848 post-transition metal Inorganic materials 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims description 3
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001887 tin oxide Inorganic materials 0.000 claims description 3
- 239000010457 zeolite Substances 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- XAYGUHUYDMLJJV-UHFFFAOYSA-Z decaazanium;dioxido(dioxo)tungsten;hydron;trioxotungsten Chemical compound [H+].[H+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].[NH4+].O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O.[O-][W]([O-])(=O)=O XAYGUHUYDMLJJV-UHFFFAOYSA-Z 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 150000002739 metals Chemical group 0.000 description 14
- 239000001913 cellulose Substances 0.000 description 12
- 229920002678 cellulose Polymers 0.000 description 12
- 235000010980 cellulose Nutrition 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000005470 impregnation Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 238000010924 continuous production Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000010948 rhodium Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920002488 Hemicellulose Polymers 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 150000004767 nitrides Chemical class 0.000 description 3
- 239000010893 paper waste Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- BQOFWKZOCNGFEC-UHFFFAOYSA-N carene Chemical compound C1C(C)=CCC2C(C)(C)C12 BQOFWKZOCNGFEC-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000004862 dioxolanes Chemical class 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 239000002803 fossil fuel Substances 0.000 description 2
- 235000001727 glucose Nutrition 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 229910052754 neon Inorganic materials 0.000 description 2
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 239000010955 niobium Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 150000004804 polysaccharides Chemical class 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- RLPGDEORIPLBNF-UHFFFAOYSA-N 2,3,4-trimethylpentane Chemical compound CC(C)C(C)C(C)C RLPGDEORIPLBNF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002299 Cellodextrin Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 244000088415 Raphanus sativus Species 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229930006737 car-3-ene Natural products 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002577 cryoprotective agent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000002029 lignocellulosic biomass Substances 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 239000010841 municipal wastewater Substances 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229910052699 polonium Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- GTCKPGDAPXUISX-UHFFFAOYSA-N ruthenium(3+);trinitrate Chemical compound [Ru+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O GTCKPGDAPXUISX-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical class [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000002916 wood waste Substances 0.000 description 1
- 229920001221 xylan Polymers 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1
Classifications
-
- 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
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/468—Iridium
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/626—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with tin
-
- 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
- B01J23/892—Nickel and noble 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
- B01J23/89—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
- B01J23/8926—Copper and noble 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
-
- 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
- B01J37/0236—Drying, e.g. preparing a suspension, adding a soluble salt and drying
-
- 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
- B01J37/16—Reducing
- B01J37/18—Reducing with gases containing free hydrogen
-
- 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
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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)
Description
水素、炭水化物源、液体希釈剤、及び触媒システムが、反応剤として、反応ゾーンに導入され;
触媒システムは、タングステン化合物、及び水素化分解金属としてルテニウム、さらには遷移金属及びポスト遷移金属から選択される少なくとも1つのプロモーター金属を含み;
炭水化物源は、その触媒システムの存在下で水素と反応させられて、エチレングリコール及びブチレングリコールを含む生成物の混合物を生じさせる。
試験は以下の手順にしたがって行った。100mgの量の原料及び1000μlの水を8mlのオートクレーブ反応器に添加した。ある量の水素化分解触媒及びタングステン化合物としてのH2WO4を反応器に添加した。原料の詳細及び触媒のタイプ及び量は、表に示されている。オートクレーブを密封し、N2、次にH2でパージし、最後に室温においてH2で50バールに加圧した。オートクレーブを約900rpmで一定の撹拌をしながら最高でも190℃まで加熱し、その温度に90分間保った。90分後、オートクレーブを室温まで冷やし、ガスクロマトグラフィーを使用して液体生成物を分析した。
表1に示した組成を有する水素化分解触媒を、タングステン酸とともに、上に記載した一般手順を用いて、水素によるグルコースの添加に用いた。触媒は、それぞれ水素化分解触媒上の金属として計算して0.1又は0.5質量%のプロモーター金属と4.9又は4.5質量%のルテニウムを含んでいた。金属の総量は各触媒について5質量%だった。水1L当たりのミリグラム金属として計算して、水素化分解触媒の量は、10mg/Lだった。各試験におけるタングステン酸の量は10mg/L水だった。結果は表1に示されている。
例1の試験に対するのと同様のやり方で一連の試験を実施し、唯一の違いは水1L当たりのミリグラム金属として計算した水素化分解触媒の量、及びタングステン酸の量が5mg/mlへと半分にされたことである。
結果は表2に示されている。
グルコース以外の炭水化物の転化のための触媒システムの適性を示すために、それ以外の試験におけるグルコースのものと同じ開始濃度、すなわち100mg/Lにおいて、一連の試験を、原料としてでんぷんを用いて行った。反応は、上述した一般手順にしたがって行った。水素化分解触媒の量は、全ての試験において、5mg金属/ml水だった。タングステン酸の量は各試験において10mg/mlだった。
触媒及び結果は表3に示されている。
Claims (18)
- 炭水化物源からエチレングリコールを製造するための方法であって、
水素、炭水化物源、液体希釈剤、及び触媒システムが、反応剤として、反応ゾーンに導入され;
前記触媒システムは、タングステン化合物、及び水素化分解金属としてルテニウム、さらには遷移金属及びポスト遷移金属から選択される少なくとも1つのプロモーター金属を含み;
前記炭水化物源は、前記触媒システムの存在下で水素と反応させられて、エチレングリコール及びブチレングリコールを含む生成物の混合物を生じさせ、
ここで、前記炭水化物源が、デンプン、グルコース、スクロース、グルコースのオリゴマー、及びそれらの組み合わせからなる群から選択され、
ルテニウムとプロモーター金属(1又は複数)の質量比が10:1〜70:1の範囲である、製造方法。 - ブチレングリコールが、連行剤を使用する共沸蒸留によって、生成物の混合物から選択的に除去される、請求項1に記載の方法。
- 触媒システムが、少なくとも+2の酸化状態を有するタングステン化合物を含む、請求項1又は2に記載の方法。
- 触媒システムが、タングステン酸(H2WO4)、タングステン酸アンモニウム、メタタングステン酸アンモニウム、パラタングステン酸アンモニウム、少なくとも1種の第1又は2族元素を含むタングステン酸塩化合物、少なくとも1種の第1又は2族元素を含むメタタングステン酸塩化合物、少なくとも1種の第1又は2族元素を含むパラタングステン酸塩化合物、酸化タングステン(WO3)、タングステンのヘテロポリ化合物、及びそれらの組み合わせからなる群から選択されるタングステン化合物を含む、請求項1〜3のいずれか一項に記載の方法。
- 触媒システムがタングステン酸を含む、請求項4に記載の方法。
- 少なくとも1種の他の遷移金属が、Cu、及び周期律表の第8、9、及び10族からのその他の水素化分解金属から選択される、請求項1〜5のいずれか一項に記載の方法。
- 周期律表の第8、9、及び10族からのその他の水素化分解金属が、Fe、Ni、Co、Pt、Pd、Rh、Ir、及びそれらの組み合わせからなる群から選択される、請求項6に記載の方法。
- ルテニウム及び少なくとも1つのプロモーター金属が、担体上に担持された触媒の形態で存在する、請求項1〜7のいずれか一項に記載の方法。
- 担体が、活性炭、シリカ、アルミナ、シリカ−アルミナ、ジルコニア、チタニア、ニオビア、酸化鉄、酸化スズ、酸化亜鉛、シリカ−ジルコニア、ゼオライトアルミノシリケート、チタノシリケート、マグネシア、炭化ケイ素、クレイ、及びそれらの組み合わせからなる群から選択される、請求項8に記載の方法。
- ルテニウムに対するタングステンのモル比が1〜25の範囲である、請求項1〜9のいずれか一項に記載の方法。
- タングステン化合物の濃度が、タングステンとして計算し、かつ炭水化物源の質量に基づいて1〜35質量%の範囲である、請求項1〜10のいずれか一項に記載の方法。
- 水素化分解金属としてのルテニウム及びプロモーター金属(1又は複数)の量は、金属として計算して、かつ反応ゾーンに導入される炭水化物源の量を基準にして、0.2〜1.0質量%の範囲である、請求項1〜10のいずれか一項に記載の方法。
- 炭水化物源が、少なくも1種のペントース含有炭水化物及び少なくとも1種のヘキソース含有炭水化物の組み合わせを含む、請求項1〜12のいずれか一項に記載の方法。
- 希釈剤がアルキレングリコールと水の混合物であり、アルキレングリコールの量が、水及びアルキレングリコールの体積を基準にして2〜25体積%の範囲である、請求項1〜13のいずれか一項に記載の方法。
- 希釈剤が、スルホキシド類、アルキレングリコール以外のアルコール類、アミド類、及びそれらの混合物からなる群から選択される1つ以上の化合物をさらに含む、請求項14に記載の方法。
- 反応ゾーン内の温度が120〜300℃の範囲にある、請求項1〜15のいずれか一項に記載の方法。
- 反応ゾーン内の水素分圧が1〜6MPaの範囲にある、請求項1〜16のいずれか一項に記載の方法。
- 反応ゾーン内での触媒システムの平均滞留時間が5分〜6時間の範囲にある、請求項1〜17のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL2014118 | 2015-01-13 | ||
NL2014118 | 2015-01-13 | ||
PCT/NL2016/050027 WO2016114659A1 (en) | 2015-01-13 | 2016-01-13 | Process for preparing ethylene glycol from a carbohydrate source |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018502920A JP2018502920A (ja) | 2018-02-01 |
JP6494795B2 true JP6494795B2 (ja) | 2019-04-03 |
Family
ID=52781243
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017555202A Active JP6494795B2 (ja) | 2015-01-13 | 2016-01-13 | 炭水化物源からエチレングルコールを製造する方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US10294180B2 (ja) |
EP (1) | EP3245180B1 (ja) |
JP (1) | JP6494795B2 (ja) |
CN (1) | CN107406359A (ja) |
CA (1) | CA2973437C (ja) |
LT (1) | LT3245180T (ja) |
PL (1) | PL3245180T3 (ja) |
WO (1) | WO2016114659A1 (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015179302A1 (en) | 2014-05-19 | 2015-11-26 | Iowa Corn Promotion Board | Process for the continuous production of ethylene glycol from carbohydrates |
CN107438591B (zh) | 2015-01-13 | 2020-10-16 | 阿凡田知识中心有限公司 | 从碳水化合物源制备乙二醇的工艺 |
US10138184B2 (en) | 2015-01-13 | 2018-11-27 | Avantium Knowledge Centre B.V. | Continuous process for preparing ethylene glycol from a carbohydrate source |
CA2973436C (en) | 2015-01-13 | 2019-06-11 | Avantium Knowledge Centre B.V. | Process for preparing ethylene glycol from a carbohydrate |
CA3001378C (en) * | 2015-10-20 | 2023-10-31 | Shell Internationale Research Maatschappij B.V. | Method for the production of glycols from a carbohydrate feed |
MY193158A (en) | 2016-06-03 | 2022-09-26 | Iowa Corn Promotion Board | Continuous processes for the highly selective conversion of aldohexose-yielding carbohydrate to ethylene glycol |
US10472310B2 (en) | 2016-06-03 | 2019-11-12 | Iowa Corn Promotion Board | Continuous processes for the highly selective conversion of sugars to propylene glycol or mixtures of propylene glycol and ethylene glycol |
CN110546123A (zh) | 2017-05-10 | 2019-12-06 | 沙特基础工业全球技术公司 | 用于异戊二烯纯化的系统和方法 |
CN111868018B (zh) * | 2018-03-14 | 2023-08-04 | 阿凡田知识中心有限公司 | 用于生产乙二醇的方法 |
CA3091470A1 (en) * | 2018-03-14 | 2019-09-19 | Avantium Knowledge Centre B.V. | Continuous or semi-continuous process for the preparation of ethylene glycol and catalyst system for use therein |
PL3765432T3 (pl) * | 2018-03-14 | 2023-01-02 | Avantium Knowledge Centre B.V. | Sposób wytwarzania glikolu etylenowego |
CN109053377A (zh) * | 2018-07-27 | 2018-12-21 | 合肥江新化工科技有限公司 | 一种提高煤或合成气制乙二醇产品质量的方法 |
CN111036277A (zh) * | 2018-10-15 | 2020-04-21 | 中国石油化工股份有限公司 | 负载型催化剂及其制备方法以及甘油加氢方法 |
CN111036287A (zh) * | 2018-10-15 | 2020-04-21 | 中国石油化工股份有限公司 | 负载型催化剂及其制备方法以及甘油加氢方法 |
JP2022548790A (ja) | 2019-09-24 | 2022-11-21 | アイオワ・コーン・プロモーション・ボード | 炭水化物からエチレングリコールへの連続的なプロセス |
CN112569958B (zh) * | 2019-09-27 | 2022-09-06 | 中国石油化工股份有限公司 | 用于生物质原料制备乙二醇的催化剂组合物及其制备方法和应用 |
CN112791737B (zh) * | 2019-10-28 | 2023-04-07 | 中国石油化工股份有限公司 | 负载型催化剂及制备方法和应用 |
CN112791723A (zh) * | 2019-10-28 | 2021-05-14 | 中国石油化工股份有限公司 | 负载型催化剂及其制备方法和应用 |
CN112791721B (zh) * | 2019-10-28 | 2023-02-17 | 中国石油化工股份有限公司 | 负载型催化剂前体、负载型催化剂及制备方法和活化方法 |
CN112717968B (zh) * | 2019-10-28 | 2022-09-27 | 中国石油化工股份有限公司 | 甘油制备1,2-丙二醇的系统和方法 |
US11319269B2 (en) | 2020-09-24 | 2022-05-03 | Iowa Corn Promotion Board | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
US11680031B2 (en) | 2020-09-24 | 2023-06-20 | T. EN Process Technology, Inc. | Continuous processes for the selective conversion of aldohexose-yielding carbohydrate to ethylene glycol using low concentrations of retro-aldol catalyst |
CN112473644B (zh) * | 2020-12-18 | 2022-08-23 | 云南森美达生物科技股份有限公司 | 负载型催化剂、制备方法及其用于γ-松油烯的制备方法 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2360685A (en) * | 1943-08-10 | 1944-10-17 | Du Pont | Azeotropic distillation |
US4430253A (en) * | 1982-02-11 | 1984-02-07 | Ethyl Corporation | Sulfide-modified ruthenium catalyst |
JPH01299239A (ja) * | 1988-05-25 | 1989-12-04 | Mitsubishi Gas Chem Co Inc | ネオペンチルグリコールの製造方法 |
US4966658A (en) * | 1989-12-27 | 1990-10-30 | Lloyd Berg | Recovery of ethylene glycol from butanediol isomers by azeotropic distillation |
US4935102A (en) * | 1989-12-27 | 1990-06-19 | Lloyd Berg | Separation of 2,3-butanediol from propylene glycol by azeotropic distillation |
US5423955A (en) | 1994-07-05 | 1995-06-13 | Lloyd Berg | Separation of propylene glycol from 1,2-butanediol by azeotropic |
CN1318043A (zh) * | 1999-07-14 | 2001-10-17 | 昭和电工株式会社 | 环己烷二甲醇化合物及其制备中间体的制备方法 |
US8143458B2 (en) | 2006-10-27 | 2012-03-27 | Archer Daniels Midland Company | Processes for isolating or purifying propylene glycol, ethylene glycol and products produced therefrom |
CN101723802B (zh) | 2008-10-24 | 2013-06-19 | 中国科学院大连化学物理研究所 | 一种纤维素制乙二醇的方法 |
CN101768050B (zh) | 2009-12-25 | 2012-12-05 | 北京大学 | 一种生产乙二醇和1,2-丙二醇的方法 |
CN102190562B (zh) * | 2010-03-17 | 2014-03-05 | 中国科学院大连化学物理研究所 | 一种多羟基化合物制乙二醇的方法 |
CN102643164B (zh) * | 2011-06-28 | 2014-07-02 | 中国科学院大连化学物理研究所 | 连续加氢裂解纤维素生产乙二醇及1,2-丙二醇的方法 |
CN102643165B (zh) | 2011-06-28 | 2014-07-02 | 中国科学院大连化学物理研究所 | 连续加氢裂解糖转化生产乙二醇及1,2-丙二醇的方法 |
US8222464B2 (en) | 2011-07-28 | 2012-07-17 | Uop Llc | Catalytic process for continuously generating polyols |
BR112013026705A2 (pt) | 2011-07-28 | 2016-12-27 | Uop Llc | processo para gerar pelo menos um poliol a partir de uma carga de alimentação, e, sistema de catalisador |
US8410319B2 (en) | 2011-07-28 | 2013-04-02 | Uop Llc | Continuous catalytic generation of polyols from cellulose with recycle |
US20110312488A1 (en) | 2011-07-28 | 2011-12-22 | Uop Llc | Catalyst system for generation of polyols from saccharide containing feedstock |
WO2013027766A1 (ja) * | 2011-08-23 | 2013-02-28 | 宇部興産株式会社 | 水素化分解用触媒及びその製造方法、並びに当該触媒を用いたヒドロキシ化合物の製造方法 |
CN102731253B (zh) * | 2011-12-20 | 2014-10-22 | 中国科学院大连化学物理研究所 | 一种抑制环醚醇生成的纤维素催化转化制乙二醇的方法 |
CN102731255B (zh) * | 2011-12-20 | 2014-10-22 | 中国科学院大连化学物理研究所 | 一种以玉米芯为原料制备乙二醇的方法 |
CN102731256B (zh) * | 2011-12-20 | 2014-10-22 | 中国科学院大连化学物理研究所 | 一种抑制环醚醇生成的纤维素转化制乙二醇的方法 |
CN103420798B (zh) * | 2012-05-18 | 2015-12-09 | 中国科学院大连化学物理研究所 | 一种高效催化转化纤维素类原料到二元醇的方法 |
CN103420797B (zh) | 2012-05-21 | 2015-04-08 | 中国科学院大连化学物理研究所 | 低金属负载量催化剂用于碳水化合物制备乙二醇的方法 |
CN102731258B (zh) * | 2012-05-21 | 2014-07-23 | 中国科学院大连化学物理研究所 | 一种碳水化合物内循环催化转化制备低碳多元醇的方法 |
US10131604B2 (en) * | 2012-08-15 | 2018-11-20 | Virent, Inc. | Catalysts for hydrodeoxygenation of oxygenated hydrocarbons |
WO2014161852A1 (en) | 2013-04-05 | 2014-10-09 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of glycols |
WO2014173973A1 (en) | 2013-04-26 | 2014-10-30 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of monoethylene glycol |
CN104370692B (zh) | 2013-08-13 | 2017-02-15 | 北京化工大学 | 一种葡萄糖氢解制备多元醇的方法 |
US9745234B2 (en) * | 2013-08-26 | 2017-08-29 | Shell Oil Company | Process for the preparation of glycols |
CN104694671B (zh) | 2013-12-10 | 2018-02-13 | 中国科学院大连化学物理研究所 | 一种木质纤维素生物质综合利用制备能源化学品的方法 |
-
2016
- 2016-01-13 EP EP16713121.8A patent/EP3245180B1/en active Active
- 2016-01-13 PL PL16713121T patent/PL3245180T3/pl unknown
- 2016-01-13 CN CN201680005604.2A patent/CN107406359A/zh active Pending
- 2016-01-13 US US15/543,091 patent/US10294180B2/en active Active
- 2016-01-13 WO PCT/NL2016/050027 patent/WO2016114659A1/en active Application Filing
- 2016-01-13 CA CA2973437A patent/CA2973437C/en active Active
- 2016-01-13 LT LTEP16713121.8T patent/LT3245180T/lt unknown
- 2016-01-13 JP JP2017555202A patent/JP6494795B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
CN107406359A (zh) | 2017-11-28 |
US20170362145A1 (en) | 2017-12-21 |
WO2016114659A1 (en) | 2016-07-21 |
PL3245180T3 (pl) | 2020-10-05 |
EP3245180B1 (en) | 2020-04-08 |
CA2973437A1 (en) | 2016-07-21 |
EP3245180A1 (en) | 2017-11-22 |
CA2973437C (en) | 2020-04-14 |
JP2018502920A (ja) | 2018-02-01 |
LT3245180T (lt) | 2020-07-27 |
US10294180B2 (en) | 2019-05-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6494795B2 (ja) | 炭水化物源からエチレングルコールを製造する方法 | |
JP6522155B2 (ja) | 炭水化物源からエチレングルコールを製造する方法 | |
JP6553743B2 (ja) | 炭水化物源からエチレングルコールを製造するための連続法 | |
JP6578376B2 (ja) | 炭水化物源からエチレングルコールを製造する方法 | |
NL2014119B1 (en) | Process for preparing alkylene glycol from a carbohydrate. | |
NL2014120B1 (en) | Process for preparing ethylene glycol from a carbohydrate. | |
CN115052851A (zh) | 一种对多元醇副产物选择性降低的从碳水化合物来源制备亚烷基二醇的方法 | |
CN115038684B (zh) | 一种对甘油选择性增加的从碳水化合物来源制备亚烷基二醇的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180608 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180709 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20181009 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190108 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190204 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190305 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6494795 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |