CN105026383A - 用于制备2,5-呋喃二甲酸的方法 - Google Patents
用于制备2,5-呋喃二甲酸的方法 Download PDFInfo
- Publication number
- CN105026383A CN105026383A CN201480010774.0A CN201480010774A CN105026383A CN 105026383 A CN105026383 A CN 105026383A CN 201480010774 A CN201480010774 A CN 201480010774A CN 105026383 A CN105026383 A CN 105026383A
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- Prior art keywords
- hmf
- fdca
- aqueous solution
- catalyst
- metal salt
- Prior art date
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- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 49
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 19
- 239000002184 metal Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 150000002402 hexoses Chemical class 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical group Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052684 Cerium Inorganic materials 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 91
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 88
- 239000000047 product Substances 0.000 description 32
- 239000000126 substance Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- 229930091371 Fructose Natural products 0.000 description 10
- 239000005715 Fructose Substances 0.000 description 10
- 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 10
- 239000002253 acid Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000000346 sugar Nutrition 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000001720 carbohydrates Chemical class 0.000 description 7
- 235000014633 carbohydrates Nutrition 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000013459 approach Methods 0.000 description 5
- 239000002663 humin Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- 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 3
- -1 HMF ester Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000011973 solid acid Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 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 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000002803 fossil fuel Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 238000007172 homogeneous catalysis Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical class OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- AHIXHWRUDZFHEZ-UHFFFAOYSA-N furan-2,3-dicarbaldehyde Chemical class O=CC=1C=COC=1C=O AHIXHWRUDZFHEZ-UHFFFAOYSA-N 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical class OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical group O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000001238 wet grinding 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
- C07D307/56—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 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
- C07D307/56—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 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
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361782589P | 2013-03-14 | 2013-03-14 | |
| US61/782,589 | 2013-03-14 | ||
| PCT/US2014/020482 WO2014158838A1 (en) | 2013-03-14 | 2014-03-05 | Process for making 2,5-furandicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105026383A true CN105026383A (zh) | 2015-11-04 |
Family
ID=51625063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480010774.0A Pending CN105026383A (zh) | 2013-03-14 | 2014-03-05 | 用于制备2,5-呋喃二甲酸的方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9562028B2 (enExample) |
| EP (1) | EP2970170B1 (enExample) |
| JP (1) | JP6208321B2 (enExample) |
| KR (1) | KR102046210B1 (enExample) |
| CN (1) | CN105026383A (enExample) |
| AU (1) | AU2014241870B2 (enExample) |
| BR (1) | BR112015022795B1 (enExample) |
| CA (1) | CA2902493C (enExample) |
| ES (1) | ES2663375T3 (enExample) |
| HU (1) | HUE038483T2 (enExample) |
| MX (1) | MX354925B (enExample) |
| RU (1) | RU2640203C2 (enExample) |
| WO (1) | WO2014158838A1 (enExample) |
| ZA (1) | ZA201507571B (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107739354A (zh) * | 2017-10-09 | 2018-02-27 | 中国科学院过程工程研究所 | 一锅一步法由果糖制备2,5‑呋喃二甲酸的方法 |
| CN108299357A (zh) * | 2017-01-12 | 2018-07-20 | 中国科学院宁波材料技术与工程研究所 | 一种双取代呋喃化合物的制备方法 |
| CN110452192A (zh) * | 2018-05-07 | 2019-11-15 | 中国科学院宁波材料技术与工程研究所 | 一种制备5-羟甲基-2-呋喃甲醛的方法 |
| CN113117705A (zh) * | 2019-12-31 | 2021-07-16 | 中国石油化工股份有限公司 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
| CN115772143A (zh) * | 2021-09-08 | 2023-03-10 | 中国石油化工股份有限公司 | 一种制备2,5-呋喃二甲酸的方法 |
| CN117362251A (zh) * | 2022-06-30 | 2024-01-09 | 中国石油化工股份有限公司 | 一种2,5-呋喃二甲酸的提纯方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112017022224B1 (pt) | 2015-04-14 | 2022-05-03 | E I Du Pont De Nemours | Processo integrado para produzir ácido 2,5-furanodicarboxílico e/ou um derivado do mesmo |
| KR101715169B1 (ko) * | 2015-05-21 | 2017-03-10 | 한국생산기술연구원 | 2,5-푸란디카르복실산의 제조 방법 |
| CN108368076B (zh) * | 2015-12-10 | 2021-08-06 | 安尼基有限责任公司 | 制备2,5-呋喃二甲酸（fdca）的方法 |
| BR112018014278B1 (pt) | 2016-01-13 | 2022-07-12 | Stora Enso Oyj | Processos para a preparação de ácido 2,5-furandicarboxílico e intermediários e derivados dos mesmos |
| CN109195961A (zh) | 2016-03-24 | 2019-01-11 | 孟山都技术公司 | 用于制备杂芳基羧酸的方法 |
| JP2017190316A (ja) * | 2016-04-15 | 2017-10-19 | 三菱ケミカル株式会社 | ２，５−フランジカルボン酸の精製方法 |
| US10495130B2 (en) * | 2016-11-11 | 2019-12-03 | The Boeing Company | Fasteners having enhanced electrical energy dispersion properties |
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| CN108299357A (zh) * | 2017-01-12 | 2018-07-20 | 中国科学院宁波材料技术与工程研究所 | 一种双取代呋喃化合物的制备方法 |
| CN108299357B (zh) * | 2017-01-12 | 2025-08-12 | 中国科学院宁波材料技术与工程研究所 | 一种双取代呋喃化合物的制备方法 |
| CN107739354A (zh) * | 2017-10-09 | 2018-02-27 | 中国科学院过程工程研究所 | 一锅一步法由果糖制备2,5‑呋喃二甲酸的方法 |
| CN107739354B (zh) * | 2017-10-09 | 2020-08-07 | 中国科学院过程工程研究所 | 一锅一步法由果糖制备2,5-呋喃二甲酸的方法 |
| CN110452192A (zh) * | 2018-05-07 | 2019-11-15 | 中国科学院宁波材料技术与工程研究所 | 一种制备5-羟甲基-2-呋喃甲醛的方法 |
| CN113117705A (zh) * | 2019-12-31 | 2021-07-16 | 中国石油化工股份有限公司 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
| CN113117705B (zh) * | 2019-12-31 | 2024-05-07 | 中国石油化工股份有限公司 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
| CN115772143A (zh) * | 2021-09-08 | 2023-03-10 | 中国石油化工股份有限公司 | 一种制备2,5-呋喃二甲酸的方法 |
| CN115772143B (zh) * | 2021-09-08 | 2024-06-11 | 中国石油化工股份有限公司 | 一种制备2,5-呋喃二甲酸的方法 |
| CN117362251A (zh) * | 2022-06-30 | 2024-01-09 | 中国石油化工股份有限公司 | 一种2,5-呋喃二甲酸的提纯方法 |
Also Published As
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| CA2902493A1 (en) | 2014-10-02 |
| BR112015022795A2 (pt) | 2017-07-18 |
| HUE038483T2 (hu) | 2018-10-29 |
| WO2014158838A1 (en) | 2014-10-02 |
| MX354925B (es) | 2018-03-23 |
| RU2015139511A (ru) | 2017-04-17 |
| EP2970170B1 (en) | 2017-12-20 |
| CA2902493C (en) | 2019-12-24 |
| KR20150127182A (ko) | 2015-11-16 |
| AU2014241870B2 (en) | 2017-06-08 |
| EP2970170A1 (en) | 2016-01-20 |
| RU2640203C2 (ru) | 2017-12-27 |
| JP6208321B2 (ja) | 2017-10-04 |
| ES2663375T3 (es) | 2018-04-12 |
| ZA201507571B (en) | 2017-01-25 |
| KR102046210B1 (ko) | 2019-11-18 |
| AU2014241870A1 (en) | 2015-08-27 |
| BR112015022795B1 (pt) | 2021-05-18 |
| MX2015011912A (es) | 2015-12-01 |
| US9562028B2 (en) | 2017-02-07 |
| EP2970170A4 (en) | 2016-04-27 |
| JP2016513641A (ja) | 2016-05-16 |
| US20160016926A1 (en) | 2016-01-21 |
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