HUE033363T2 - Process for the preparation of 5-hydroxymethylfurfurol (HMF) from hexose solutions in the presence of steam - Google Patents
Process for the preparation of 5-hydroxymethylfurfurol (HMF) from hexose solutions in the presence of steam Download PDFInfo
- Publication number
- HUE033363T2 HUE033363T2 HUE12808306A HUE12808306A HUE033363T2 HU E033363 T2 HUE033363 T2 HU E033363T2 HU E12808306 A HUE12808306 A HU E12808306A HU E12808306 A HUE12808306 A HU E12808306A HU E033363 T2 HUE033363 T2 HU E033363T2
- Authority
- HU
- Hungary
- Prior art keywords
- hmf
- hexose
- starting
- solution
- steam
- Prior art date
Links
- 150000002402 hexoses Chemical class 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title claims 2
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 17
- 238000009835 boiling Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000005715 Fructose Substances 0.000 claims description 11
- 229930091371 Fructose Natural products 0.000 claims description 11
- 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 description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 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 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 230000009261 transgenic effect Effects 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 239000011888 foil Substances 0.000 claims 1
- 239000003517 fume Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 39
- 239000000463 material Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002663 humin Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GCTNBVHDRFKLLK-UHFFFAOYSA-N thujane Natural products CC1CCC2(C(C)C)C1C2 GCTNBVHDRFKLLK-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11193157 | 2011-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUE033363T2 true HUE033363T2 (en) | 2017-11-28 |
Family
ID=47458896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HUE12808306A HUE033363T2 (en) | 2011-12-13 | 2012-12-11 | Process for the preparation of 5-hydroxymethylfurfurol (HMF) from hexose solutions in the presence of steam |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP2791126B1 (enExample) |
| JP (1) | JP6073363B2 (enExample) |
| KR (1) | KR101970853B1 (enExample) |
| CN (1) | CN104169263B (enExample) |
| BR (1) | BR112014014054B1 (enExample) |
| CA (1) | CA2856864C (enExample) |
| ES (1) | ES2626835T3 (enExample) |
| HU (1) | HUE033363T2 (enExample) |
| RU (1) | RU2014128460A (enExample) |
| WO (1) | WO2013087613A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9156802B2 (en) | 2011-12-13 | 2015-10-13 | Basf Se | Separating off 5-hydroxymethylfurfural (HMF) from reaction solutions by steam distillation |
| DE102016224073A1 (de) * | 2016-12-02 | 2018-06-07 | Südzucker AG | Verbessertes HMF-Herstellungsverfahren |
| CN113825745B (zh) * | 2019-04-15 | 2025-04-04 | 斯道拉恩索公司 | 用于回收溶剂和分离腐殖质材料及其组合物的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| US3201331A (en) * | 1962-10-17 | 1965-08-17 | Atlas Chem Ind | Purification of hydroxymethyl furfural |
| 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 |
| FR2663933B1 (fr) * | 1990-06-27 | 1994-06-17 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| EP1834950A1 (en) | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of 5-alkoxymethylfurfural ethers and their use |
| EP1834951A1 (en) | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of organic acid esters of 5-hydroxymethylfurfural and their use |
| EP2033958A1 (en) * | 2007-09-07 | 2009-03-11 | Furanix Technologies B.V | Hydroxymethylfurfural ethers from sugars and di- and triols |
| CN101456850A (zh) * | 2007-12-12 | 2009-06-17 | 中国科学院大连化学物理研究所 | 一种制备5-羟甲基糠醛的方法 |
| CN101812039B (zh) * | 2010-05-14 | 2012-09-26 | 天津大学 | 一种利用离子液体催化生成5－羟甲基糠醛的方法 |
| CN102399203B (zh) * | 2011-12-19 | 2014-05-07 | 浙江大学 | 一种离子液体降解碳水化合物制备5-羟甲基糠醛的方法 |
-
2012
- 2012-12-11 CA CA2856864A patent/CA2856864C/en not_active Expired - Fee Related
- 2012-12-11 BR BR112014014054-5A patent/BR112014014054B1/pt not_active IP Right Cessation
- 2012-12-11 ES ES12808306.0T patent/ES2626835T3/es active Active
- 2012-12-11 KR KR1020147019046A patent/KR101970853B1/ko not_active Expired - Fee Related
- 2012-12-11 HU HUE12808306A patent/HUE033363T2/en unknown
- 2012-12-11 WO PCT/EP2012/075055 patent/WO2013087613A1/de not_active Ceased
- 2012-12-11 RU RU2014128460A patent/RU2014128460A/ru not_active Application Discontinuation
- 2012-12-11 EP EP12808306.0A patent/EP2791126B1/de not_active Not-in-force
- 2012-12-11 JP JP2014546456A patent/JP6073363B2/ja not_active Expired - Fee Related
- 2012-12-11 CN CN201280059056.3A patent/CN104169263B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2791126A1 (de) | 2014-10-22 |
| CA2856864A1 (en) | 2013-06-20 |
| CA2856864C (en) | 2021-05-25 |
| BR112014014054B1 (pt) | 2019-03-19 |
| RU2014128460A (ru) | 2016-02-10 |
| EP2791126B1 (de) | 2017-03-01 |
| CN104169263B (zh) | 2016-06-15 |
| WO2013087613A1 (de) | 2013-06-20 |
| KR20140101849A (ko) | 2014-08-20 |
| JP2015500313A (ja) | 2015-01-05 |
| CN104169263A (zh) | 2014-11-26 |
| JP6073363B2 (ja) | 2017-02-01 |
| KR101970853B1 (ko) | 2019-04-19 |
| BR112014014054A2 (pt) | 2017-06-13 |
| ES2626835T3 (es) | 2017-07-26 |
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