CA2937506C - Conversion of fructose-containing feedstocks to hmf-containing product - Google Patents
Conversion of fructose-containing feedstocks to hmf-containing product Download PDFInfo
- Publication number
- CA2937506C CA2937506C CA2937506A CA2937506A CA2937506C CA 2937506 C CA2937506 C CA 2937506C CA 2937506 A CA2937506 A CA 2937506A CA 2937506 A CA2937506 A CA 2937506A CA 2937506 C CA2937506 C CA 2937506C
- Authority
- CA
- Canada
- Prior art keywords
- fructose
- hmf
- solvent
- reaction zone
- combination
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 290
- 239000005715 Fructose Substances 0.000 title claims abstract description 247
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 title claims abstract description 247
- 229930091371 Fructose Natural products 0.000 title claims abstract description 247
- 239000002904 solvent Substances 0.000 claims abstract description 174
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 165
- 229910001868 water Inorganic materials 0.000 claims abstract description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 87
- 230000008569 process Effects 0.000 claims abstract description 79
- 239000003377 acid catalyst Substances 0.000 claims abstract description 19
- 239000006241 High Modulus Furnace Substances 0.000 claims description 142
- 239000000047 product Substances 0.000 claims description 89
- 239000012528 membrane Substances 0.000 claims description 74
- 239000000543 intermediate Substances 0.000 claims description 68
- 239000002663 humin Substances 0.000 claims description 42
- 238000001728 nano-filtration Methods 0.000 claims description 25
- 239000007787 solid Substances 0.000 claims description 25
- 239000012466 permeate Substances 0.000 claims description 24
- 238000000108 ultra-filtration Methods 0.000 claims description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 12
- 239000012465 retentate Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 235000011007 phosphoric acid Nutrition 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 47
- 238000011084 recovery Methods 0.000 abstract description 23
- 239000003054 catalyst Substances 0.000 description 82
- 239000000470 constituent Substances 0.000 description 52
- 239000000203 mixture Substances 0.000 description 27
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 25
- 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 22
- 239000008103 glucose Substances 0.000 description 22
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
- 238000000638 solvent extraction Methods 0.000 description 21
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- 238000005342 ion exchange Methods 0.000 description 15
- 239000002815 homogeneous catalyst Substances 0.000 description 13
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000000622 liquid--liquid extraction Methods 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 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 11
- 235000019253 formic acid Nutrition 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000007806 chemical reaction intermediate Substances 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 10
- 229940040102 levulinic acid Drugs 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 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 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000002638 heterogeneous catalyst Substances 0.000 description 8
- 235000019534 high fructose corn syrup Nutrition 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- 208000012839 conversion disease Diseases 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- -1 halide salt Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 238000010791 quenching Methods 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000011088 calibration curve Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000011027 product recovery Methods 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 3
- SSXJHQZOHUYEGD-UHFFFAOYSA-N 3,3',4',5,6,7,8-Heptamethoxyflavone Natural products C1=C(OC)C(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 SSXJHQZOHUYEGD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012527 feed solution Substances 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 150000002402 hexoses Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- DLVYTANECMRFGX-UHFFFAOYSA-N norfuraneol Natural products CC1=C(O)C(=O)CO1 DLVYTANECMRFGX-UHFFFAOYSA-N 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- PJVXUVWGSCCGHT-ZPYZYFCMSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(3s,4r,5r)-1,3,4,5,6-pentahydroxyhexan-2-one Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO PJVXUVWGSCCGHT-ZPYZYFCMSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 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
- 229910052726 zirconium Inorganic materials 0.000 description 2
- FZRJRIPXNVGOHZ-HSUXUTPPSA-N (2r,3s,4s)-2-(hydroxymethyl)-5-(hydroxymethylidene)oxolane-3,4-diol Chemical compound OC[C@H]1OC(=CO)[C@@H](O)[C@@H]1O FZRJRIPXNVGOHZ-HSUXUTPPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- LKDRXBCSQODPBY-ZXXMMSQZSA-N alpha-D-fructopyranose Chemical compound OC[C@]1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-ZXXMMSQZSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000012435 analytical chromatography Methods 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical class F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005112 continuous flow technique Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 238000009295 crossflow filtration Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005373 pervaporation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/02—Reverse osmosis; Hyperfiltration ; Nanofiltration
- B01D61/027—Nanofiltration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D61/00—Processes of separation using semi-permeable membranes, e.g. dialysis, osmosis or ultrafiltration; Apparatus, accessories or auxiliary operations specially adapted therefor
- B01D61/14—Ultrafiltration; Microfiltration
- B01D61/145—Ultrafiltration
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/02—Specific process operations before starting the membrane separation process
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2311/00—Details relating to membrane separation process operations and control
- B01D2311/25—Recirculation, recycling or bypass, e.g. recirculation of concentrate into the feed
- B01D2311/252—Recirculation of concentrate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Water Supply & Treatment (AREA)
- Nanotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461932185P | 2014-01-27 | 2014-01-27 | |
| US61/932,185 | 2014-01-27 | ||
| PCT/US2015/013130 WO2015113060A2 (en) | 2014-01-27 | 2015-01-27 | Conversion of fructose-containing feedstocks to hmf-containing product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2937506A1 CA2937506A1 (en) | 2015-07-30 |
| CA2937506C true CA2937506C (en) | 2022-12-20 |
Family
ID=52462483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2937506A Active CA2937506C (en) | 2014-01-27 | 2015-01-27 | Conversion of fructose-containing feedstocks to hmf-containing product |
Country Status (12)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10316009B2 (en) | 2015-08-21 | 2019-06-11 | Gfbiochemicals Ip Assets B.V. | Process to prepare hydroxymethylfurfural derivatives |
| AU2017207824B2 (en) | 2016-01-13 | 2021-05-20 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
| WO2017184545A1 (en) * | 2016-04-18 | 2017-10-26 | Rennovia, Inc. | Conversion of fructose-containing feedstocks to hmf-containing product |
| DE102016224073A1 (de) * | 2016-12-02 | 2018-06-07 | Südzucker AG | Verbessertes HMF-Herstellungsverfahren |
| US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| CN108250165B (zh) * | 2018-01-10 | 2021-03-26 | 南昌大学 | 一种利用生物质碳水化合物制备n-(5-甲基糠基)苯胺及衍生物的方法 |
| 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 |
| DE102018208510A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Salz- und Säuregemisch-katalysierte HMF-Herstellung |
| DE102018208507A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
| IT201800007204A1 (it) * | 2018-07-13 | 2020-01-13 | Processo per la produzione e la separazione di 5-idrossimetilfurfurale con sali ammonici quaternari” | |
| JP2022529935A (ja) * | 2019-04-15 | 2022-06-27 | ストラ エンソ オーユーイー | 溶媒の回収方法、腐植質の単離方法、および溶媒または腐植質からなる組成物 |
| EP4110510A1 (en) | 2020-02-28 | 2023-01-04 | The Procter & Gamble Company | Method to remove chemical contaminants |
| KR102420365B1 (ko) * | 2020-04-07 | 2022-07-14 | 주식회사 한솔케미칼 | 나노입자의 대량 정제 시스템 및 이를 이용한 나노입자의 대량 정제방법 |
| MX2023004204A (es) * | 2020-10-13 | 2023-05-19 | Archer Daniels Midland Co | Pretratamiento oxidativo de productos de deshidratacion de carbohidratos que comprenden huminas. |
| 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 |
| CN113861139B (zh) * | 2021-11-04 | 2023-12-12 | 浙江糖能科技有限公司 | 一种制备5-羟甲基糠醛的方法 |
| KR102735762B1 (ko) * | 2022-03-11 | 2024-11-28 | 경북대학교 산학협력단 | 전기화학적 환원반응을 통한 hmf으로부터 bhmf 생산용 촉매 전극 및 이의 제조방법 |
| KR20250064997A (ko) | 2023-11-03 | 2025-05-12 | 한국생산기술연구원 | 금속질산염 및 이온성 액체를 포함하는 촉매, 그리고 그를 이용한 글루코스 및 고과당 옥수수 시럽 유래 5-히드록시메틸푸르푸랄 생산 방법 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB591858A (en) | 1944-05-30 | 1947-09-01 | Walter Norman Haworth | Improvements relating to the manufacture of 5-hydroxy-methyl furfural or levulinic acid |
| GB600871A (en) | 1945-10-17 | 1948-04-21 | Walter Norman Haworth | Improvements relating to the manufacture of 5-hydroxymethyl 2-furfural |
| US2750394A (en) | 1952-05-22 | 1956-06-12 | Food Chemical And Res Lab Inc | Manufacture of 5-hydroxymethyl 2-furfural |
| US2754330A (en) | 1952-12-12 | 1956-07-10 | Du Pont | Manufacture of aliphatic diamines |
| US2929823A (en) | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| US2917520A (en) | 1957-09-11 | 1959-12-15 | Arthur C Cope | Production and recovery of furans |
| GB876463A (en) | 1959-02-25 | 1961-09-06 | Atlas Powder Co | Process for preparing hydroxymethyl furfural |
| US3118912A (en) | 1960-04-18 | 1964-01-21 | Rayonier Inc | Preparation of hydroxymethylfurfural |
| FR2464260A1 (fr) | 1979-09-05 | 1981-03-06 | Roquette Freres | Procede de fabrication du 5-hydroxymethylfurfural |
| US4400468A (en) | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
| FR2551754B1 (fr) | 1983-09-14 | 1988-04-08 | Roquette Freres | Procede de fabrication du 5-hydroxymethylfurfural |
| US4533743A (en) | 1983-12-16 | 1985-08-06 | Atlantic Richfield Company | Furfural process |
| DE3601281A1 (de) | 1986-01-17 | 1987-07-23 | Sueddeutsche Zucker Ag | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
| AT387247B (de) | 1987-05-12 | 1988-12-27 | Voest Alpine Ind Anlagen | Kombiniertes verfahren zur thermischen und chemischen behandlung von lignocellulosehaltiger biomasse und zur gewinnung von furfural |
| DE3842825A1 (de) | 1988-01-08 | 1989-07-20 | Krupp Gmbh | Verfahren und vorrichtung zur herstellung von furfural |
| FR2664273B1 (fr) | 1990-06-27 | 1994-04-29 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| FR2663933B1 (fr) | 1990-06-27 | 1994-06-17 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| FR2669635B1 (fr) | 1990-11-22 | 1994-06-10 | Furchim | Procede de fabrication d'hydroxymethylfurfural (hmf) du purete elevee. |
| KR920008374B1 (ko) | 1990-12-04 | 1992-09-26 | 일양약품 주식회사 | 항종양 면역증강효과가 있는 단백다당체(G 009)를 생성하는 가노데르마루시덤(Ganoderma lucidum) IY 009 |
| FR2670209B1 (fr) | 1990-12-07 | 1995-04-28 | Commissariat Energie Atomique | Procede de preparation d'hydroxymethyl-5 furfural par catalyse heterogene. |
| DE19905655A1 (de) | 1999-02-11 | 2000-08-17 | Karl Zeitsch | Verfahren zur Herstellung von Furfural durch verzögerte Entspannung |
| US6518440B2 (en) | 2001-03-05 | 2003-02-11 | Gene E. Lightner | Hydroxymethylfurfural derived from cellulose contained in lignocellulose solids |
| US7393963B2 (en) | 2004-12-10 | 2008-07-01 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
| US7317116B2 (en) | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| ATE473218T1 (de) | 2006-03-10 | 2010-07-15 | Furanix Technologies Bv | Verwendung organischer säureester von 5- hydroxymethylfurfural |
| WO2007146636A1 (en) | 2006-06-06 | 2007-12-21 | Wisconsin Alumni Research Foundation | Catalytic process for producing furan derivatives from carbohydrates in a biphasic reactor |
| BRPI0813534A2 (pt) * | 2007-07-18 | 2017-05-02 | Archer Daniels-Midland Company | método para produção de 5-hidroximetil-2-furfural a partir de frutose |
| CA2726126C (en) | 2008-06-17 | 2018-07-17 | Wisconsin Alumni Research Foundation | Chemical transformation of lignocellulosic biomass into fuels and chemicals |
| BRPI1010708B1 (pt) | 2009-06-13 | 2018-04-03 | Rennovia, Inc. | "processos para preparar um produto de ácido adípico, e ácido adípico ou derivado do mesmo" |
| BR112012024133A2 (pt) | 2010-04-07 | 2015-09-15 | Novozymes As | método para produzir 5-hidroximetilfurfural e para converter hmf, e, uso de ácido 2, 5-furanodicarboxílico |
| EP2390247A1 (en) | 2010-05-26 | 2011-11-30 | Netherlands Organisation for Scientific Research (Advanced Chemical Technologies for Sustainability) | Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde |
| FR2975396B1 (fr) | 2011-05-16 | 2013-12-27 | Centre Nat Rech Scient | Procede de preparation de 5-hydroxymethylfurfural |
| WO2013034763A1 (en) | 2011-09-09 | 2013-03-14 | Dsm Ip Assets B.V. | Process for the separation of a bio -based product by distillation and permeation |
| BR112014008911A2 (pt) | 2011-10-12 | 2017-05-09 | Novozymes As | processo para a produção de 5-hidroximetilfurfural |
| JP5846008B2 (ja) * | 2012-03-30 | 2016-01-20 | 王子ホールディングス株式会社 | バイオマスからの単糖類、オリゴ糖類及びフルフラール類の製造方法 |
| KR20140101850A (ko) * | 2011-12-13 | 2014-08-20 | 바스프 에스이 | (표준 압력에서) 60℃ 초과 내지 200℃ 미만의 비점을 갖는 용매 (간략히 저비점 물질이라 칭함)의 존재 하에 사카라이드 용액으로부터 5-히드록시메틸푸르푸랄 (hmf)을 제조하는 방법 |
| AU2012364787A1 (en) * | 2012-01-10 | 2014-07-03 | Archer Daniels Midland Company | Process for making HMF and HMF derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol |
| CN106008163B (zh) | 2012-01-18 | 2019-10-08 | 阿彻丹尼尔斯米德兰公司 | 从5-羟甲基糠醛产生六亚甲基二胺的方法 |
| KR101217137B1 (ko) | 2012-03-05 | 2012-12-31 | 한국생산기술연구원 | 프록토오스를 포함하는 옥수수시럽으로부터 5-히드록시메틸-2-푸르푸랄을 제조하는 방법 |
| US9090579B2 (en) | 2012-03-12 | 2015-07-28 | Archer Daniels Midland Co. | Processes for making sugar and/or sugar alcohol dehydration products |
| WO2014037560A1 (en) | 2012-09-10 | 2014-03-13 | Dsm Ip Assets B.V. | Process for the separation of levulinic acid from biomass |
| US8772515B2 (en) | 2012-10-11 | 2014-07-08 | Wisconsin Alumni Research Foundation | Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents |
| US9199957B2 (en) | 2012-12-21 | 2015-12-01 | Petroleo Brasileiro S.A.-Petrobras | 2.5-furandicarboxylic acid integrated production process |
| WO2014152366A1 (en) | 2013-03-14 | 2014-09-25 | Pronghorn Renewables Llc | Method and catalyst for the production of alcohols, diols, cyclic ethers and other products from pentose and hexose sugars |
-
2015
- 2015-01-27 CN CN201580009754.6A patent/CN106029642B/zh active Active
- 2015-01-27 CA CA2937506A patent/CA2937506C/en active Active
- 2015-01-27 US US14/606,789 patent/US9611241B2/en active Active
- 2015-01-27 EP EP15703214.5A patent/EP3099670A2/en not_active Withdrawn
- 2015-01-27 JP JP2016548180A patent/JP2017505310A/ja active Pending
- 2015-01-27 EA EA201691459A patent/EA201691459A1/ru unknown
- 2015-01-27 MX MX2016009657A patent/MX2016009657A/es unknown
- 2015-01-27 SG SG11201606169PA patent/SG11201606169PA/en unknown
- 2015-01-27 WO PCT/US2015/013130 patent/WO2015113060A2/en active Application Filing
- 2015-01-27 KR KR1020167022495A patent/KR20160111954A/ko not_active Withdrawn
- 2015-01-27 BR BR112016016751-1A patent/BR112016016751B1/pt active IP Right Grant
- 2015-01-27 AU AU2015209026A patent/AU2015209026A1/en not_active Abandoned
-
2017
- 2017-02-21 US US15/437,570 patent/US10017486B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| WO2015113060A3 (en) | 2015-11-12 |
| BR112016016751B1 (pt) | 2021-08-31 |
| WO2015113060A2 (en) | 2015-07-30 |
| US10017486B2 (en) | 2018-07-10 |
| CN106029642B (zh) | 2019-11-29 |
| JP2017505310A (ja) | 2017-02-16 |
| US20170158656A1 (en) | 2017-06-08 |
| KR20160111954A (ko) | 2016-09-27 |
| US9611241B2 (en) | 2017-04-04 |
| BR112016016751A2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2017-08-08 |
| SG11201606169PA (en) | 2016-08-30 |
| EA201691459A1 (ru) | 2016-12-30 |
| US20150210661A1 (en) | 2015-07-30 |
| MX2016009657A (es) | 2017-01-20 |
| CA2937506A1 (en) | 2015-07-30 |
| WO2015113060A9 (en) | 2016-11-10 |
| CN106029642A (zh) | 2016-10-12 |
| AU2015209026A1 (en) | 2016-07-28 |
| EP3099670A2 (en) | 2016-12-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2937506C (en) | Conversion of fructose-containing feedstocks to hmf-containing product | |
| US8048655B2 (en) | Recovery of organic acids | |
| WO2017217279A1 (ja) | イソプロピルアルコールの製造方法及び不純物が低減されたイソプロピルアルコール | |
| WO2017184545A1 (en) | Conversion of fructose-containing feedstocks to hmf-containing product | |
| CN110035999B (zh) | 羟甲基糠醛制备方法 | |
| EP2914601A1 (en) | Improved method of making internal dehydration products of sugar alcohols | |
| US20170015642A1 (en) | Conversion of fructose-containing feedstocks to hmf-containing product | |
| EP1351949B1 (en) | Continuous process for producing l-ascorbic acid | |
| AU2019276050B2 (en) | Salt and acid mixture catalyzed hmf production | |
| AU2019276047B2 (en) | Anolyte fraction-catalyzed hmf production | |
| Choi et al. | Separation of bio-based glucaric acid via antisolvent crystallization and azeotropic drying | |
| US20240391861A1 (en) | Process for the recovery of monopotassium glucarate and glucaric acid | |
| CA2969273C (en) | Process for manufacturing succinic acid from a fermentation broth using nano filtration to purify recycled mother liquor | |
| EA045367B1 (ru) | Получение hmf, катализируемое смесью соли и кислоты | |
| EA045455B1 (ru) | Получение hmf, катализируемое фракцией анолита |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20200123 |
|
| EEER | Examination request |
Effective date: 20200123 |
|
| EEER | Examination request |
Effective date: 20200123 |