JP5757739B2 - 無機溶融塩水和物中で多糖類を転化する方法 - Google Patents
無機溶融塩水和物中で多糖類を転化する方法 Download PDFInfo
- Publication number
- JP5757739B2 JP5757739B2 JP2010550217A JP2010550217A JP5757739B2 JP 5757739 B2 JP5757739 B2 JP 5757739B2 JP 2010550217 A JP2010550217 A JP 2010550217A JP 2010550217 A JP2010550217 A JP 2010550217A JP 5757739 B2 JP5757739 B2 JP 5757739B2
- Authority
- JP
- Japan
- Prior art keywords
- molten salt
- inorganic
- inorganic molten
- hydrolysis
- salt hydrate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 86
- -1 salt hydrates Chemical class 0.000 title claims description 27
- 150000004676 glycans Chemical class 0.000 title claims description 17
- 229920001282 polysaccharide Polymers 0.000 title claims description 17
- 239000005017 polysaccharide Substances 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 claims description 165
- 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 claims description 65
- 230000007062 hydrolysis Effects 0.000 claims description 61
- 238000006460 hydrolysis reaction Methods 0.000 claims description 61
- 239000000600 sorbitol Substances 0.000 claims description 58
- 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 56
- 239000008103 glucose Substances 0.000 claims description 55
- 239000001913 cellulose Substances 0.000 claims description 51
- 229920002678 cellulose Polymers 0.000 claims description 51
- 238000005984 hydrogenation reaction Methods 0.000 claims description 51
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 229960002479 isosorbide Drugs 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- 229920005862 polyol Polymers 0.000 claims description 25
- 150000003077 polyols Chemical class 0.000 claims description 25
- 239000012978 lignocellulosic material Substances 0.000 claims description 19
- 229920002488 Hemicellulose Polymers 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 229910052723 transition metal Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 12
- 150000002772 monosaccharides Chemical class 0.000 claims description 11
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 10
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000007789 gas Substances 0.000 claims description 7
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000000811 xylitol Substances 0.000 claims description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 3
- 235000010447 xylitol Nutrition 0.000 claims description 3
- 229960002675 xylitol Drugs 0.000 claims description 3
- 229910021193 La 2 O 3 Inorganic materials 0.000 claims description 2
- 229910017493 Nd 2 O 3 Inorganic materials 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 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
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004760 silicates Chemical class 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 claims 1
- YKAVHPRGGAUFDN-JTQLBUQXSA-N 24464-30-0 Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]2(C)O[C@]3([C@@H]([C@H]2O)C)[C@H](C)C[C@](O3)(C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 YKAVHPRGGAUFDN-JTQLBUQXSA-N 0.000 claims 1
- 229910017119 AlPO Inorganic materials 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 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 79
- 229960002920 sorbitol Drugs 0.000 description 66
- 230000018044 dehydration Effects 0.000 description 64
- 238000006297 dehydration reaction Methods 0.000 description 64
- 208000005156 Dehydration Diseases 0.000 description 63
- 235000010356 sorbitol Nutrition 0.000 description 63
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- 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 description 51
- 239000000047 product Substances 0.000 description 47
- 239000002609 medium Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 36
- 235000000346 sugar Nutrition 0.000 description 30
- 239000000243 solution Substances 0.000 description 26
- 230000000694 effects Effects 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 229920005610 lignin Polymers 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- 239000002028 Biomass Substances 0.000 description 15
- 238000000926 separation method Methods 0.000 description 15
- 150000005846 sugar alcohols Chemical class 0.000 description 14
- 239000010949 copper Substances 0.000 description 13
- 238000004090 dissolution Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 239000012266 salt solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004517 catalytic hydrocracking Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 150000008163 sugars Chemical class 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 230000008901 benefit Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000008929 regeneration Effects 0.000 description 5
- 238000011069 regeneration method Methods 0.000 description 5
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 235000010355 mannitol Nutrition 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- KLDXJTOLSGUMSJ-KVTDHHQDSA-N (3r,3ar,6r,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-KVTDHHQDSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 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 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- MCHWWJLLPNDHGL-JGWLITMVSA-N (2s,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-JGWLITMVSA-N 0.000 description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 229920000875 Dissolving pulp Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 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 2
- 239000005715 Fructose Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 229910052776 Thorium Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 239000010905 bagasse Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 239000012738 dissolution medium Substances 0.000 description 2
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000002029 lignocellulosic biomass Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AAFJXZWCNVJTMK-KVTDHHQDSA-N (1S,2S)-1,2-bis[(2R)-oxiran-2-yl]ethane-1,2-diol Chemical compound C([C@@H]1[C@@H](O)[C@H](O)[C@@H]2OC2)O1 AAFJXZWCNVJTMK-KVTDHHQDSA-N 0.000 description 1
- JNYAEWCLZODPBN-SLPGGIOYSA-N (2r,3r,4r)-2-[(1s)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@H](O)[C@H]1OC[C@@H](O)[C@H]1O JNYAEWCLZODPBN-SLPGGIOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-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
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 1
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052773 Promethium Inorganic materials 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052767 actinium Inorganic materials 0.000 description 1
- QQINRWTZWGJFDB-UHFFFAOYSA-N actinium atom Chemical compound [Ac] QQINRWTZWGJFDB-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal 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
- 238000007796 conventional method Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000909 electrodialysis Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 150000008131 glucosides Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 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
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- XLROVYAPLOFLNU-UHFFFAOYSA-N protactinium atom Chemical compound [Pa] XLROVYAPLOFLNU-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 238000010850 salt effect Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000629 steam reforming Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
- A23L29/37—Sugar alcohols
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H8/00—Macromolecular compounds derived from lignocellulosic materials
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K1/00—Glucose; Glucose-containing syrups
- C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Food Science & Technology (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08152706.1 | 2008-03-13 | ||
| EP08152706A EP2100972A1 (en) | 2008-03-13 | 2008-03-13 | Process for converting polysaccharides in a molten salt hydrate |
| PCT/EP2009/053027 WO2009112588A1 (en) | 2008-03-13 | 2009-03-13 | Process for converting polysaccharides in an inorganic molten salt hydrate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011517552A JP2011517552A (ja) | 2011-06-16 |
| JP2011517552A5 JP2011517552A5 (enExample) | 2012-05-31 |
| JP5757739B2 true JP5757739B2 (ja) | 2015-07-29 |
Family
ID=39645536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010550217A Expired - Fee Related JP5757739B2 (ja) | 2008-03-13 | 2009-03-13 | 無機溶融塩水和物中で多糖類を転化する方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8445704B2 (enExample) |
| EP (2) | EP2100972A1 (enExample) |
| JP (1) | JP5757739B2 (enExample) |
| CN (1) | CN102027138B (enExample) |
| BR (1) | BRPI0909325A2 (enExample) |
| CA (1) | CA2718145A1 (enExample) |
| ES (1) | ES2542981T3 (enExample) |
| MY (1) | MY156012A (enExample) |
| RU (1) | RU2503722C2 (enExample) |
| WO (1) | WO2009112588A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2408782A1 (en) * | 2009-03-17 | 2012-01-25 | BIOeCON International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| WO2010106052A1 (en) * | 2009-03-17 | 2010-09-23 | Bioecon International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| EP2408937A1 (en) * | 2009-03-17 | 2012-01-25 | BIOeCON International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| ES2438180T3 (es) * | 2009-03-17 | 2014-01-16 | Bioecon International Holding N.V. | Procedimiento para convertir polisacáridos en una sal fundida inorgánica hidratada |
| DE102009023458A1 (de) * | 2009-06-02 | 2010-12-30 | Carl Freudenberg Kg | Lösung, umfassend Cellulose, Verfahren zu deren Herstellung sowie deren Verwendung |
| US8628623B2 (en) * | 2009-12-21 | 2014-01-14 | Andritz Technology And Asset Management Gmbh | Method and process for dry discharge in a pressurized pretreatment reactor |
| JP5823756B2 (ja) * | 2010-07-21 | 2015-11-25 | 国立大学法人北海道大学 | 糖アルコールの製造方法 |
| FR2963008B1 (fr) * | 2010-07-23 | 2013-01-04 | IFP Energies Nouvelles | Procede de production de sucres a partir de biomasse lignocellulosique pretraitee avec un melange de sels inorganiques hydrates et de sels metalliques |
| FR2963009B1 (fr) * | 2010-07-23 | 2013-01-04 | IFP Energies Nouvelles | Procede de production de sucres a partir de biomasse lignocellulosique pretraitee avec des sels inorganiques hydrates |
| EP2431394A1 (en) | 2010-09-17 | 2012-03-21 | BIOeCON International Holding N.V. | Simultaneous hydrolysis and hydrogenation of cellulose |
| CN102600640B (zh) * | 2012-01-09 | 2015-05-13 | 中德瑞生物炼制实验室(厦门)有限公司 | 一种木质纤维素水解物的糖、酸、盐分离方法 |
| EP2620442A1 (en) * | 2012-01-27 | 2013-07-31 | BIOeCON International Holding N.V. | Process for recovering saccharides from cellulose hydrolysis reaction mixture |
| JPWO2014007295A1 (ja) * | 2012-07-03 | 2016-06-02 | 昭和電工株式会社 | 植物性バイオマスの分解方法及びグルコースの製造方法 |
| EP2882755B1 (en) * | 2012-08-08 | 2019-02-06 | Roquette Freres | Method of synthesis of a composition containing at least one internal dehydration product of a hydrogenated sugar by heterogeneous catalysis |
| FR2999604B1 (fr) * | 2012-12-14 | 2017-01-13 | Ifp Energies Now | Procede de production de solutions de sucres et d'alcools a partir de biomasse lignocellulosique avec traitement complementaire du residu solide par un sel inorganique hydrate |
| CN103012065B (zh) * | 2012-12-27 | 2015-03-18 | 中国科学院广州能源研究所 | 一种生物质循环水解氢化制取高浓度多元醇的方法 |
| DE102014208368A1 (de) * | 2014-05-05 | 2015-11-05 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Gewinnung von aromatischen Verbindungen |
| WO2015198267A1 (en) * | 2014-06-27 | 2015-12-30 | Eni S.P.A. | Process for obtaining compounds useful for the production of biofuels starting from cellulose |
| CN104226131A (zh) * | 2014-09-16 | 2014-12-24 | 广州大学 | 一种溶解淀粉方法 |
| EP3230480B1 (en) | 2014-12-09 | 2018-10-03 | BIOeCON International Holding N.V. | Process for the isolation of monosaccharides |
| JP6521659B2 (ja) * | 2015-02-16 | 2019-05-29 | 株式会社日本触媒 | ポリオール類またはアルコール類の製造方法 |
| JP6725994B2 (ja) * | 2015-03-03 | 2020-07-22 | 株式会社豊田中央研究所 | 水蒸気改質触媒、それを用いた水蒸気改質方法、及び水蒸気改質反応装置 |
| WO2016139936A1 (ja) * | 2015-03-03 | 2016-09-09 | 株式会社デンソー | 水蒸気改質触媒、それを用いた水蒸気改質方法、及び水蒸気改質反応装置 |
| CN106938196A (zh) | 2015-12-10 | 2017-07-11 | 财团法人工业技术研究院 | 固体催化剂及应用该催化剂的醣类的制备方法 |
| EP3416740B1 (en) | 2016-02-19 | 2021-01-06 | Intercontinental Great Brands LLC | Processes to create multiple value streams from biomass sources |
| EP3213814A1 (en) * | 2016-03-01 | 2017-09-06 | Antecy B.V. | Novel sorbent and/or catalyst composition |
| US20190060820A1 (en) | 2016-03-01 | 2019-02-28 | Antecy B.V. | Shaped attrition resistant particles for co2 capturing and conversion |
| TWI653085B (zh) * | 2016-06-13 | 2019-03-11 | 鼎唐能源科技股份有限公司 | 從水解纖維素製程產物水溶液中分離醣類的方法 |
| US10781196B2 (en) | 2016-08-17 | 2020-09-22 | University Of Delaware | Integrated process for direct saccharification and dehydration of intact biomass to furfurals |
| CN108690039A (zh) * | 2018-06-26 | 2018-10-23 | 大连理工大学 | 一种山梨醇脱水制备异山梨醇的方法 |
| CN109569591A (zh) * | 2018-12-19 | 2019-04-05 | 武汉轻工大学 | 一种纤维素基Ru/C催化剂及其制备方法 |
| CN109879723B (zh) * | 2019-01-23 | 2020-10-20 | 厦门大学 | 从半纤维素直接制备木糖醇的方法 |
| CN109879721B (zh) * | 2019-01-23 | 2021-10-01 | 厦门大学 | 一种从半纤维素直接制备木糖醇的方法 |
| CN110183538A (zh) * | 2019-06-21 | 2019-08-30 | 大连工业大学 | 一种无机熔盐-微酸共促进体系制备纤维素纳米晶体的方法 |
| CN110894097B (zh) * | 2019-12-12 | 2022-04-12 | 山东理工大学 | 含叔丁醇废水的深度氧化处理方法 |
| CN111876454B (zh) * | 2020-08-14 | 2022-09-13 | 中国科学院青岛生物能源与过程研究所 | 采用熔盐水合物体系预处理木质纤维原料的方法 |
| US12163288B2 (en) | 2021-01-19 | 2024-12-10 | Solenis Technologies, L.P. | Treated substrates and methods of producing the same |
| WO2023104635A1 (en) | 2021-12-06 | 2023-06-15 | Heiq Materials Ag | Process for fabrication of regenerated cellulose yarns derived from recycled waste feedstocks |
| JPWO2024058256A1 (enExample) * | 2022-09-14 | 2024-03-21 | ||
| WO2024245773A1 (en) | 2023-05-26 | 2024-12-05 | HeiQ AeoniQ Holding AG | Oxidative process for fabrication of regenerated cellulose yarns derived from recycled waste feedstocks |
| WO2025162806A1 (en) | 2024-01-31 | 2025-08-07 | HeiQ AeoniQ Holding AG | Process for fabrication of cellulose yarns derived from cellulose feedstocks |
| CN118308684B (zh) * | 2024-04-01 | 2025-11-04 | 福州大学 | 一种热喷涂预处理木质素制氢催化剂的方法及其处理装置 |
| CN119016104B (zh) * | 2024-08-14 | 2025-05-13 | 北京石油化工学院 | 一种用于山梨醇脱水制异山梨醇反应的改性分子筛催化剂及其制备方法和应用 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US607091A (en) | 1898-07-12 | einar simonsen | ||
| US257607A (en) | 1882-05-09 | alexander paekes | ||
| US647805A (en) | 1900-01-29 | 1900-04-17 | Alexander Classen | Process of converting wood into fermentable sugars. |
| SU114200A1 (ru) * | 1957-09-26 | 1957-11-30 | А.М. Малков | Способ кислотного гидролиза целлюлозосодержащего сырь |
| US3538019A (en) * | 1968-03-07 | 1970-11-03 | Atlas Chem Ind | Nickel phosphate-promoted supported nickel catalyst |
| US3471580A (en) * | 1968-04-19 | 1969-10-07 | Hydrocarbon Research Inc | Production of glycerol from saccharides |
| US4018620A (en) | 1975-05-19 | 1977-04-19 | Biocel Corporation | Method of hydrolyzing cellulose to monosaccharides |
| US4313884A (en) | 1980-01-21 | 1982-02-02 | Uop Inc. | Use of metal ions in preparation of anhydropolyols |
| EP0091221B1 (en) | 1982-04-05 | 1987-09-09 | Imperial Chemical Industries Plc | Solubilisation and hydrolysis of carbohydrates |
| US4452640A (en) | 1982-05-11 | 1984-06-05 | Purdue Research Foundation | Quantitative hydrolysis of cellulose to glucose using zinc chloride |
| US4525218A (en) * | 1982-05-11 | 1985-06-25 | Purdue Research Foundation | Selective hydrolysis of cellulose to glucose without degradation of glucose using zinc chloride |
| US4694113A (en) * | 1986-06-04 | 1987-09-15 | Pfizer Inc. | Dual catalyst sequential method for production of sorbitol from hydrolyzed starch solution |
| JPH01202300A (ja) * | 1988-02-05 | 1989-08-15 | Agency Of Ind Science & Technol | セルロース類の糖化方法 |
| IL110126A (en) * | 1994-06-26 | 2001-01-28 | Gadot Biochemical Ind Ltd | Process for the manufacture of isomaltitol |
| FI102962B (fi) * | 1996-06-24 | 1999-03-31 | Xyrofin Oy | Menetelmä ksylitolin valmistamiseksi |
| JP4223579B2 (ja) * | 1996-11-18 | 2009-02-12 | 三菱商事フードテック株式会社 | キシロースおよびキシリトールの製造方法 |
| DE19749202C1 (de) | 1997-11-07 | 1999-05-27 | Degussa | Verfahren zur Herstellung von fünf- oder sechsgliedrigen cyclischen Ethern und Anhydrohexitgemische |
| DE19841032A1 (de) | 1998-09-09 | 2000-03-16 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Anhydrozuckeralkoholen |
| FI106853B (fi) * | 1998-11-18 | 2001-04-30 | Xyrofin Oy | Menetelmä polyolien valmistamiseksi arabinoksylaania sisältävästä materiaalista |
| AU2001264807A1 (en) | 2000-05-26 | 2001-12-11 | E.I. Du Pont De Nemours And Company | Process for the manufacture of anhydro sugar alcohols with the assistance of a gas purge |
| AU2001264848A1 (en) | 2000-05-26 | 2001-12-11 | E.I. Du Pont De Nemours And Company | Continuous process for the manufacture of anhydro sugar alcohols and reactor useful therefor |
| US6864378B2 (en) | 2002-04-17 | 2005-03-08 | E. I. Du Pont De Nemours And Company | Integrated continuous process for anhydro sugar alcohol manufacture |
| US6831181B2 (en) | 2002-04-17 | 2004-12-14 | E. I. Dupont De Nemours And Co. | High yield byproduct recycle process for anhydro sugar alcohols |
| JP4205963B2 (ja) * | 2003-02-03 | 2009-01-07 | 株式会社日本触媒 | 色相の優れた高純度トリエタノールアミンの製造方法 |
| JP4908218B2 (ja) * | 2003-05-06 | 2012-04-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された１，３−プロパンジオールの水素化 |
| US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| US7339007B2 (en) * | 2003-06-20 | 2008-03-04 | Infineum International Limited | Low sediment process for thermally reacting highly reactive polymers and enophiles |
| JP2005341924A (ja) * | 2004-06-07 | 2005-12-15 | Electric Power Dev Co Ltd | 植物性資源から糖類を製造する方法 |
| US7649099B2 (en) | 2006-01-26 | 2010-01-19 | Battelle Memorial Institute | Method of forming a dianhydrosugar alcohol |
| US7615652B2 (en) | 2006-01-26 | 2009-11-10 | Battelle Memorial Institute | Two-stage dehydration of sugars |
| US7772412B2 (en) | 2006-01-26 | 2010-08-10 | Battelle Memorial Institute | Methods for dehydration of sugars and sugar alcohols |
| US7728156B2 (en) | 2006-01-26 | 2010-06-01 | Battelle Memorial Institute | Method of performing sugar dehydration and catalyst treatment |
| NZ571184A (en) * | 2006-03-24 | 2011-06-30 | Wisconsin Alumni Res Found | Method for producing bio-fuel that integrates heat from carbon-carbon bond-forming reactions to drive biomass gasification reactions |
-
2008
- 2008-03-13 EP EP08152706A patent/EP2100972A1/en not_active Withdrawn
-
2009
- 2009-03-13 ES ES09720250.1T patent/ES2542981T3/es active Active
- 2009-03-13 EP EP09720250.1A patent/EP2283164B1/en not_active Not-in-force
- 2009-03-13 WO PCT/EP2009/053027 patent/WO2009112588A1/en not_active Ceased
- 2009-03-13 BR BRPI0909325-7A patent/BRPI0909325A2/pt not_active IP Right Cessation
- 2009-03-13 JP JP2010550217A patent/JP5757739B2/ja not_active Expired - Fee Related
- 2009-03-13 CA CA2718145A patent/CA2718145A1/en not_active Abandoned
- 2009-03-13 RU RU2010141854/13A patent/RU2503722C2/ru not_active IP Right Cessation
- 2009-03-13 MY MYPI2010004268A patent/MY156012A/en unknown
- 2009-03-13 CN CN200980117227.1A patent/CN102027138B/zh not_active Expired - Fee Related
-
2010
- 2010-09-13 US US12/880,241 patent/US8445704B2/en active Active
-
2013
- 2013-04-22 US US13/867,253 patent/US20140039208A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MY156012A (en) | 2015-12-31 |
| JP2011517552A (ja) | 2011-06-16 |
| EP2100972A1 (en) | 2009-09-16 |
| US20110060148A1 (en) | 2011-03-10 |
| RU2010141854A (ru) | 2012-04-20 |
| US20140039208A1 (en) | 2014-02-06 |
| WO2009112588A1 (en) | 2009-09-17 |
| ES2542981T3 (es) | 2015-08-13 |
| EP2283164B1 (en) | 2015-05-06 |
| US8445704B2 (en) | 2013-05-21 |
| CN102027138A (zh) | 2011-04-20 |
| BRPI0909325A2 (pt) | 2015-08-04 |
| EP2283164A1 (en) | 2011-02-16 |
| CA2718145A1 (en) | 2009-09-17 |
| RU2503722C2 (ru) | 2014-01-10 |
| CN102027138B (zh) | 2015-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5757739B2 (ja) | 無機溶融塩水和物中で多糖類を転化する方法 | |
| US8440845B2 (en) | Process for converting polysaccharides in an inorganic molten salt hydrate | |
| US8263792B2 (en) | Biomass refining by selective chemical reactions | |
| de Almeida et al. | Cellulose conversion to isosorbide in molten salt hydrate media | |
| US4476331A (en) | Two stage hydrogenolysis of carbohydrate to glycols using sulfide modified ruthenium catalyst in second stage | |
| EP2825543B1 (en) | Process for making sugar and/or sugar alcohol dehydration products | |
| WO2015004369A1 (fr) | Procede de transformation de biomasses lignocellulosiques en molecules mono ou poly-oxygenees | |
| KR20160143760A (ko) | 환원 당 알코올, 퓨란 유도체의 합성 | |
| WO2013102002A1 (en) | Processes for making furfurals | |
| EP2408782A1 (en) | Process for converting polysaccharides in an inorganic molten salt hydrate | |
| US10519124B2 (en) | Synthesis of R-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols | |
| WO2010106052A1 (en) | Process for converting polysaccharides in an inorganic molten salt hydrate | |
| CN107912039B (zh) | 用于制备糠醛衍生物的方法 | |
| WO2010106055A1 (en) | Process for converting polysaccharides in an inorganic molten salt hydrate | |
| US20170121258A1 (en) | Synthesis of r-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols | |
| De Almeida et al. | O'Connor et al | |
| CN107848996B (zh) | 包括中和酸性反应混合物的用于制备糖醛衍生物的方法 | |
| JP7659917B2 (ja) | ２，５－ジホルミルフランの合成方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120312 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120326 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130719 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130731 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131016 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131023 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131119 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131126 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20131210 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20131217 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140905 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141226 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20150312 |
|
| 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: 20150512 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150602 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5757739 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |