BR112016013316B1 - Método para a produção de furfural e uso de ácido metanossulfônico - Google Patents
Método para a produção de furfural e uso de ácido metanossulfônico Download PDFInfo
- Publication number
- BR112016013316B1 BR112016013316B1 BR112016013316-1A BR112016013316A BR112016013316B1 BR 112016013316 B1 BR112016013316 B1 BR 112016013316B1 BR 112016013316 A BR112016013316 A BR 112016013316A BR 112016013316 B1 BR112016013316 B1 BR 112016013316B1
- Authority
- BR
- Brazil
- Prior art keywords
- weight
- feed mixture
- aqueous feed
- xylose
- salts
- Prior art date
Links
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 200
- 238000000034 method Methods 0.000 title claims abstract description 77
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 23
- 239000002253 acid Substances 0.000 title claims description 19
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims abstract description 152
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 144
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims abstract description 79
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 79
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 70
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 claims abstract description 70
- 239000000126 substance Substances 0.000 claims abstract description 57
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 46
- 229920001542 oligosaccharide Polymers 0.000 claims abstract description 43
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 37
- 239000005017 polysaccharide Substances 0.000 claims abstract description 37
- 150000004676 glycans Chemical class 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 190
- 238000000605 extraction Methods 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 79
- 239000007788 liquid Substances 0.000 claims description 77
- 239000007791 liquid phase Substances 0.000 claims description 72
- 238000010438 heat treatment Methods 0.000 claims description 52
- 239000003960 organic solvent Substances 0.000 claims description 44
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 42
- 150000004804 polysaccharides Polymers 0.000 claims description 41
- 210000004027 cell Anatomy 0.000 claims description 39
- 239000002028 Biomass Substances 0.000 claims description 35
- 229920002678 cellulose Polymers 0.000 claims description 27
- 239000001913 cellulose Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 239000011780 sodium chloride Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 18
- 238000012545 processing Methods 0.000 claims description 17
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 claims description 17
- -1 tetrafluoroborate Chemical compound 0.000 claims description 15
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 12
- 238000011084 recovery Methods 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 238000007669 thermal treatment Methods 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 210000005253 yeast cell Anatomy 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 229960003487 xylose Drugs 0.000 description 70
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 55
- 150000002402 hexoses Chemical class 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 25
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 11
- 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 description 9
- 239000008103 glucose Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 206010049865 Achromotrichia acquired Diseases 0.000 description 8
- 229930091371 Fructose Natural products 0.000 description 8
- 239000005715 Fructose Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 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 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 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 7
- 230000008901 benefit Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000003929 acidic solution Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229920005610 lignin Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 229920001221 xylan Polymers 0.000 description 3
- 150000004823 xylans Chemical class 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002972 pentoses Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002910 solid waste Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 229920003043 Cellulose fiber Polymers 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
- 241000196324 Embryophyta Species 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 241000235344 Saccharomycetaceae Species 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001312 aldohexoses Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 150000002574 ketohexoses Chemical class 0.000 description 1
- 239000012978 lignocellulosic material Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000010850 salt effect Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13197237.4A EP2883871A1 (en) | 2013-12-13 | 2013-12-13 | Production of furfural from xylose |
| EP13197237.4 | 2013-12-13 | ||
| PCT/IB2014/066752 WO2015087248A1 (en) | 2013-12-13 | 2014-12-10 | Production of furfural from xylose |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BR112016013316A2 BR112016013316A2 (https=) | 2017-08-08 |
| BR112016013316A8 BR112016013316A8 (pt) | 2020-05-19 |
| BR112016013316B1 true BR112016013316B1 (pt) | 2020-10-06 |
Family
ID=49882812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112016013316-1A BR112016013316B1 (pt) | 2013-12-13 | 2014-12-10 | Método para a produção de furfural e uso de ácido metanossulfônico |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9944614B2 (https=) |
| EP (2) | EP2883871A1 (https=) |
| JP (1) | JP6529502B2 (https=) |
| KR (1) | KR102355640B1 (https=) |
| CN (1) | CN105980369B (https=) |
| BR (1) | BR112016013316B1 (https=) |
| CA (1) | CA2933308C (https=) |
| ES (1) | ES2701851T3 (https=) |
| MY (1) | MY189230A (https=) |
| WO (1) | WO2015087248A1 (https=) |
| ZA (1) | ZA201604586B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10138217B2 (en) | 2013-09-03 | 2018-11-27 | Virdia, Inc. | Methods for extracting and converting hemicellulose sugars |
| JP6447061B2 (ja) * | 2014-11-28 | 2019-01-09 | 三菱ケミカル株式会社 | フルフラール製造触媒の回収方法、フルフラール製造触媒、および該フルフラール製造触媒を用いたフルフラールの製造方法 |
| CN105597757B (zh) * | 2015-12-23 | 2018-01-02 | 北京林业大学 | 磁性氧化石墨烯催化剂及其制备方法及其应用 |
| JP6648545B2 (ja) * | 2016-02-08 | 2020-02-14 | 三菱ケミカル株式会社 | フルフラール製造原料用糖液の製造方法及びフルフラールの製造方法 |
| JP6961963B2 (ja) | 2016-04-01 | 2021-11-05 | 三菱ケミカル株式会社 | フルフラールの製造方法 |
| CN116529232A (zh) * | 2020-09-23 | 2023-08-01 | 博奥股份公司 | 用于生产乙酰丙酸的方法 |
| CN112337418B (zh) * | 2020-10-22 | 2021-08-10 | 华中科技大学 | 一种生物质连续制取呋喃和可燃气的反应系统及方法 |
| CN116529236A (zh) * | 2020-12-18 | 2023-08-01 | 国际壳牌研究有限公司 | 用于生产糠醛的方法和系统 |
| CN115894193B (zh) * | 2021-09-30 | 2024-05-03 | 中国石油化工股份有限公司 | 一种氢过氧化物酸分解的方法 |
| KR102752224B1 (ko) * | 2022-09-28 | 2025-01-10 | 한국화학연구원 | 전처리 단계를 수반하는 5-할로메틸푸르푸랄 제조방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4533743A (en) | 1983-12-16 | 1985-08-06 | Atlantic Richfield Company | Furfural process |
| EP2032550B1 (en) | 2006-06-06 | 2013-11-20 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives from carbohydrates in a biphasic reactor |
| AU2008310260A1 (en) * | 2007-10-10 | 2009-04-16 | Mascoma Canada Inc. | Enzymatic treatment under vacuum of lignocellulosic materials |
| US9024047B2 (en) | 2010-12-21 | 2015-05-05 | E I Du Pont De Nemours And Company | Methods for furfural production from branched non-fermentable sugars in stillage or syrup |
| US8524924B2 (en) * | 2010-12-21 | 2013-09-03 | E I Du Pont De Nemours And Company | Process for furfural production from biomass |
| US8389749B2 (en) * | 2011-05-25 | 2013-03-05 | Wisconsin Alumni Research Foundation | Method to produce, recover and convert furan derivatives from aqueous solutions using alkylphenol extraction |
| FR2979344B1 (fr) * | 2011-08-26 | 2014-01-24 | Centre Nat Rech Scient | Procede de preparation de furfural |
| CN102391218B (zh) | 2011-12-23 | 2013-12-25 | 吉林大学 | 一种固定床催化木糖脱水制备糠醛的方法 |
| CA2859996A1 (en) | 2011-12-28 | 2013-07-04 | Paul Joseph Fagan | Process for the production of furfural |
| KR102053293B1 (ko) * | 2012-03-12 | 2019-12-06 | 조지아-퍼시픽 엘엘씨 | 목질계 바이오매스로부터 레불린산을 제조하는 방법 |
-
2013
- 2013-12-13 EP EP13197237.4A patent/EP2883871A1/en not_active Withdrawn
-
2014
- 2014-12-10 US US15/103,336 patent/US9944614B2/en active Active
- 2014-12-10 MY MYPI2016001063A patent/MY189230A/en unknown
- 2014-12-10 ES ES14869955T patent/ES2701851T3/es active Active
- 2014-12-10 WO PCT/IB2014/066752 patent/WO2015087248A1/en not_active Ceased
- 2014-12-10 EP EP14869955.6A patent/EP3080094B1/en active Active
- 2014-12-10 BR BR112016013316-1A patent/BR112016013316B1/pt active IP Right Grant
- 2014-12-10 JP JP2016538575A patent/JP6529502B2/ja active Active
- 2014-12-10 CA CA2933308A patent/CA2933308C/en active Active
- 2014-12-10 CN CN201480075425.7A patent/CN105980369B/zh active Active
- 2014-12-10 KR KR1020167018352A patent/KR102355640B1/ko not_active Expired - Fee Related
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2016
- 2016-07-06 ZA ZA2016/04586A patent/ZA201604586B/en unknown
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|---|---|
| CA2933308A1 (en) | 2015-06-18 |
| EP2883871A1 (en) | 2015-06-17 |
| US9944614B2 (en) | 2018-04-17 |
| KR102355640B1 (ko) | 2022-01-26 |
| EP3080094B1 (en) | 2018-09-19 |
| US20160304481A1 (en) | 2016-10-20 |
| BR112016013316A2 (https=) | 2017-08-08 |
| BR112016013316A8 (pt) | 2020-05-19 |
| EP3080094A4 (en) | 2017-09-06 |
| CN105980369A (zh) | 2016-09-28 |
| ZA201604586B (en) | 2017-11-29 |
| JP6529502B2 (ja) | 2019-06-12 |
| CA2933308C (en) | 2022-10-25 |
| JP2016539999A (ja) | 2016-12-22 |
| ES2701851T3 (es) | 2019-02-26 |
| WO2015087248A1 (en) | 2015-06-18 |
| CN105980369B (zh) | 2019-01-15 |
| KR20160097293A (ko) | 2016-08-17 |
| EP3080094A1 (en) | 2016-10-19 |
| MY189230A (en) | 2022-01-31 |
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