DE3601281A1 - Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel - Google Patents
Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittelInfo
- Publication number
- DE3601281A1 DE3601281A1 DE19863601281 DE3601281A DE3601281A1 DE 3601281 A1 DE3601281 A1 DE 3601281A1 DE 19863601281 DE19863601281 DE 19863601281 DE 3601281 A DE3601281 A DE 3601281A DE 3601281 A1 DE3601281 A1 DE 3601281A1
- Authority
- DE
- Germany
- Prior art keywords
- hmf
- fructose
- fractions
- solution
- water
- 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.)
- Granted
Links
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 83
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000002904 solvent Substances 0.000 title claims abstract description 12
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- 229930091371 Fructose Natural products 0.000 claims abstract description 36
- 239000005715 Fructose Substances 0.000 claims abstract description 36
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims abstract description 35
- 150000001720 carbohydrates Chemical class 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 235000014633 carbohydrates Nutrition 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 28
- 239000013078 crystal Substances 0.000 claims description 25
- 238000002425 crystallisation Methods 0.000 claims description 23
- 230000008025 crystallization Effects 0.000 claims description 23
- 238000004587 chromatography analysis Methods 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 229920001202 Inulin Polymers 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(OC[C@]2(OC[C@]3(OC[C@]4(OC[C@]5(OC[C@]6(OC[C@]7(OC[C@]8(OC[C@]9(OC[C@]%10(OC[C@]%11(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims description 9
- 229940029339 inulin Drugs 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000006188 syrup Substances 0.000 claims description 8
- 235000020357 syrup Nutrition 0.000 claims description 8
- 235000007542 Cichorium intybus Nutrition 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 150000002402 hexoses Chemical class 0.000 claims description 6
- 235000000346 sugar Nutrition 0.000 claims description 6
- 229930006000 Sucrose Natural products 0.000 claims description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 239000005720 sucrose Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 150000002482 oligosaccharides Chemical class 0.000 claims description 4
- 238000005342 ion exchange Methods 0.000 claims description 3
- 229920001542 oligosaccharide Polymers 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims 2
- 150000004676 glycans Chemical class 0.000 claims 2
- 229920001282 polysaccharide Polymers 0.000 claims 2
- 239000005017 polysaccharide Substances 0.000 claims 2
- 244000298479 Cichorium intybus Species 0.000 claims 1
- 240000008892 Helianthus tuberosus Species 0.000 claims 1
- 235000003230 Helianthus tuberosus Nutrition 0.000 claims 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 claims 1
- 238000005341 cation exchange Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000005445 natural material Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 10
- 239000003960 organic solvent Substances 0.000 abstract description 9
- 238000000926 separation method Methods 0.000 abstract description 9
- 230000018044 dehydration Effects 0.000 abstract description 6
- 238000006297 dehydration reaction Methods 0.000 abstract description 6
- 239000007858 starting material Substances 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 description 12
- 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 11
- 239000008103 glucose Substances 0.000 description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 241000723343 Cichorium Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000011575 calcium Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019534 high fructose corn syrup Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000008346 aqueous phase Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 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 2
- 235000021433 fructose syrup Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 2
- QAVITTVTXPZTSE-UHFFFAOYSA-N (5-formylfuran-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CC=C(C=O)O1 QAVITTVTXPZTSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling 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
- 239000000287 crude extract Substances 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 229930182479 fructoside Natural products 0.000 description 1
- 150000008132 fructosides Chemical class 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- -1 sucrose Chemical compound 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 238000010626 work up procedure 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863601281 DE3601281A1 (de) | 1986-01-17 | 1986-01-17 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
| US07/002,340 US4740605A (en) | 1986-01-17 | 1987-01-12 | Process for preparing pure 5-hydroxymethylfurfuraldehyde |
| EP87100311A EP0230250B1 (de) | 1986-01-17 | 1987-01-13 | Verfahren zur Herstellung von 5-Hydroxymethylfurfural einschliesslich eines kristallinen Produktes unter ausschliesslicher Verwendung von Wasser als Lösungsmittel |
| AT87100311T ATE62236T1 (de) | 1986-01-17 | 1987-01-13 | Verfahren zur herstellung von 5hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel. |
| DE8787100311T DE3768965D1 (de) | 1986-01-17 | 1987-01-13 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863601281 DE3601281A1 (de) | 1986-01-17 | 1986-01-17 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3601281A1 true DE3601281A1 (de) | 1987-07-23 |
| DE3601281C2 DE3601281C2 (OSRAM) | 1988-08-04 |
Family
ID=6292062
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863601281 Granted DE3601281A1 (de) | 1986-01-17 | 1986-01-17 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
| DE8787100311T Expired - Lifetime DE3768965D1 (de) | 1986-01-17 | 1987-01-13 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787100311T Expired - Lifetime DE3768965D1 (de) | 1986-01-17 | 1987-01-13 | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4740605A (OSRAM) |
| EP (1) | EP0230250B1 (OSRAM) |
| AT (1) | ATE62236T1 (OSRAM) |
| DE (2) | DE3601281A1 (OSRAM) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7317116B2 (en) | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| US7432382B2 (en) | 2004-12-10 | 2008-10-07 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
| EP2474235A2 (de) | 2007-07-06 | 2012-07-11 | Basf Se | Verfahren zur Gewinnung von Maisgluten |
| WO2013087613A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | Herstellung von 5-hydroxymethylfurfural (hmf) aus hexoselösungen in gegenwart von wasserdampf |
| WO2013087523A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | Abtrennung von 5-hydroxymethylfurfural (hmf) aus reaktionslösungen durch wasserdampf-destillation |
| WO2013087614A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | HERSTELLUNG VON 5-HYDROXYMETHYLFURFURAL (HMF) AUS SACCHARIDLÖSUNGEN IN GEGENWART EINES LÖSEMITTELS MIT EINEM SIEDEPUNKT GRÖßER 60°C UND KLEINER 200°C (BEI NORMALDRUCK, KURZ LEICHTSIEDER GENANNT) |
| EP2813494A1 (de) | 2013-06-12 | 2014-12-17 | Basf Se | Verfahren zur Herstellung von 5-Hydroxymethylfurfural (HMF) |
| US9156802B2 (en) | 2011-12-13 | 2015-10-13 | Basf Se | Separating off 5-hydroxymethylfurfural (HMF) from reaction solutions by steam distillation |
| US9162998B2 (en) | 2011-12-13 | 2015-10-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (HMF) from saccharide solutions in the presence of a solvent having a boiling point greater than 60° C. and less than 200° C. (at standard pressure, called low boiler for short) |
| US9169227B2 (en) | 2011-12-13 | 2015-10-27 | Basf Se | Production of 5 hydroxymethyulfurfural (HMF) from hexose solutions in the presence of steam |
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Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3936522A1 (de) * | 1989-11-02 | 1991-05-08 | Suedzucker Ag | 5-((alpha)-d-glucopyranosyloxymethyl)-furan-2-carboxaldehyd und dessen derivate und folgeprodukte sowie verfahren zur herstellung der verbindungen und deren verwendung |
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| KR102219915B1 (ko) | 2019-04-10 | 2021-02-23 | 부산대학교 산학협력단 | 가스-액체 계면 플라즈마 공정을 이용한 술폰화된 고체산 촉매의 제조방법 |
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| FR3097547B1 (fr) * | 2019-06-24 | 2023-04-28 | Ifp Energies Now | Procede de production de 5-hydroxymethylfurfural |
| CN116082278A (zh) * | 2021-11-05 | 2023-05-09 | 中国科学院宁波材料技术与工程研究所 | 一种提高制备5-羟甲基-2-呋喃甲醛选择性的方法 |
| CN114805254A (zh) * | 2022-04-11 | 2022-07-29 | 合肥利夫生物科技有限公司 | 一种5-羟甲基糠醛的制备方法 |
| WO2025043536A1 (zh) * | 2023-08-30 | 2025-03-06 | 乔璞科技股份有限公司 | 5-羟甲基糠醛的纯化方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| DE3033527A1 (de) * | 1979-09-05 | 1981-04-02 | Roquette Frères, Lestrem | Verfahren zur herstellung von 5-hydroxymethylfurfural |
| DE3309564A1 (de) * | 1983-03-17 | 1984-09-20 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 5-acetoxymethyl-furfural |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776948A (en) * | 1953-08-03 | 1957-01-08 | Dendrol Inc | Synthetic resins derived from hydroxymethylfurfural and phenols |
-
1986
- 1986-01-17 DE DE19863601281 patent/DE3601281A1/de active Granted
-
1987
- 1987-01-12 US US07/002,340 patent/US4740605A/en not_active Expired - Fee Related
- 1987-01-13 EP EP87100311A patent/EP0230250B1/de not_active Expired - Lifetime
- 1987-01-13 AT AT87100311T patent/ATE62236T1/de not_active IP Right Cessation
- 1987-01-13 DE DE8787100311T patent/DE3768965D1/de not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| DE3033527A1 (de) * | 1979-09-05 | 1981-04-02 | Roquette Frères, Lestrem | Verfahren zur herstellung von 5-hydroxymethylfurfural |
| DE3309564A1 (de) * | 1983-03-17 | 1984-09-20 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 5-acetoxymethyl-furfural |
Non-Patent Citations (6)
| Title |
|---|
| Carbohydr. Res. 122, 1983, S.59-68 * |
| Chem. Abstr. 100, 1984, Ref. 120 866 * |
| J. Chem. Soc., 1944, S.667 * |
| J. Chem. Soc., 1960, S.787-791 * |
| J. Chem. Tech. Biotechnol., 31, 1981, S.135-145 * |
| J. Chem. Tech. Biotechnol., 32, 1982, S.920-924 * |
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| US7317116B2 (en) | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| US7432382B2 (en) | 2004-12-10 | 2008-10-07 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
| US7579490B2 (en) | 2004-12-10 | 2009-08-25 | Archer-Daniels-Midland Company | Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor |
| US7579489B2 (en) | 2004-12-10 | 2009-08-25 | Archer-Daniels-Midland Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| US8058458B2 (en) | 2004-12-10 | 2011-11-15 | Archer Daniels Midland Company | Processes for the preparation and purification of hydroxymethylfuraldehyde derivatives |
| EP2474235A2 (de) | 2007-07-06 | 2012-07-11 | Basf Se | Verfahren zur Gewinnung von Maisgluten |
| US9156802B2 (en) | 2011-12-13 | 2015-10-13 | Basf Se | Separating off 5-hydroxymethylfurfural (HMF) from reaction solutions by steam distillation |
| WO2013087523A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | Abtrennung von 5-hydroxymethylfurfural (hmf) aus reaktionslösungen durch wasserdampf-destillation |
| WO2013087614A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | HERSTELLUNG VON 5-HYDROXYMETHYLFURFURAL (HMF) AUS SACCHARIDLÖSUNGEN IN GEGENWART EINES LÖSEMITTELS MIT EINEM SIEDEPUNKT GRÖßER 60°C UND KLEINER 200°C (BEI NORMALDRUCK, KURZ LEICHTSIEDER GENANNT) |
| WO2013087613A1 (de) | 2011-12-13 | 2013-06-20 | Basf Se | Herstellung von 5-hydroxymethylfurfural (hmf) aus hexoselösungen in gegenwart von wasserdampf |
| US9162998B2 (en) | 2011-12-13 | 2015-10-20 | Basf Se | Preparation of 5-hydroxymethylfurfural (HMF) from saccharide solutions in the presence of a solvent having a boiling point greater than 60° C. and less than 200° C. (at standard pressure, called low boiler for short) |
| US9169227B2 (en) | 2011-12-13 | 2015-10-27 | Basf Se | Production of 5 hydroxymethyulfurfural (HMF) from hexose solutions in the presence of steam |
| EP2813494A1 (de) | 2013-06-12 | 2014-12-17 | Basf Se | Verfahren zur Herstellung von 5-Hydroxymethylfurfural (HMF) |
| DE102016224073A1 (de) * | 2016-12-02 | 2018-06-07 | Südzucker AG | Verbessertes HMF-Herstellungsverfahren |
| US10662167B2 (en) | 2016-12-02 | 2020-05-26 | Sudzucker Ag | HMF production method |
| EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
| DE102018208507A1 (de) * | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
| DE102018208510A1 (de) * | 2018-05-29 | 2019-12-05 | Südzucker AG | Salz- und Säuregemisch-katalysierte HMF-Herstellung |
| US11548863B2 (en) | 2018-05-29 | 2023-01-10 | Südzucker AG | Preparation of HMF catalyzed by a mixture of salt and acid |
| US11697642B2 (en) | 2018-05-29 | 2023-07-11 | Südzucker AG | HMF preparation catalysed by anolyte fraction |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE62236T1 (de) | 1991-04-15 |
| US4740605A (en) | 1988-04-26 |
| EP0230250B1 (de) | 1991-04-03 |
| DE3601281C2 (OSRAM) | 1988-08-04 |
| DE3768965D1 (de) | 1991-05-08 |
| EP0230250A3 (en) | 1988-08-31 |
| EP0230250A2 (de) | 1987-07-29 |
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