JP2005506984A5 - - Google Patents
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- JP2005506984A5 JP2005506984A5 JP2003528795A JP2003528795A JP2005506984A5 JP 2005506984 A5 JP2005506984 A5 JP 2005506984A5 JP 2003528795 A JP2003528795 A JP 2003528795A JP 2003528795 A JP2003528795 A JP 2003528795A JP 2005506984 A5 JP2005506984 A5 JP 2005506984A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction mixture
- diformylfuran
- temperature
- solvent
- fructose
- 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.)
- Pending
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- 238000000034 method Methods 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 11
- PXJJKVNIMAZHCB-UHFFFAOYSA-N 2,5-diformylfuran Chemical compound O=CC1=CC=C(C=O)O1 PXJJKVNIMAZHCB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 150000003682 vanadium compounds Chemical class 0.000 claims description 4
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 description 6
- 229930091371 Fructose Natural products 0.000 description 6
- 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 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 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
- 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
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 1
- LUYWGGWGYMURNR-UHFFFAOYSA-M [O-2].[O-2].[OH-].O.P.[V+5] Chemical compound [O-2].[O-2].[OH-].O.P.[V+5] LUYWGGWGYMURNR-UHFFFAOYSA-M 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32262901P | 2001-09-17 | 2001-09-17 | |
| PCT/US2002/029464 WO2003024947A1 (en) | 2001-09-17 | 2002-09-17 | Process for preparing 2,5-diformylfuran from carbohydrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005506984A JP2005506984A (ja) | 2005-03-10 |
| JP2005506984A5 true JP2005506984A5 (enExample) | 2006-01-05 |
Family
ID=23255706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003528795A Pending JP2005506984A (ja) | 2001-09-17 | 2002-09-17 | 炭水化物からの２，５−ジホルミルフランの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6706900B2 (enExample) |
| EP (1) | EP1427715B1 (enExample) |
| JP (1) | JP2005506984A (enExample) |
| KR (1) | KR20040044933A (enExample) |
| CN (1) | CN1555368A (enExample) |
| DE (1) | DE60211535T2 (enExample) |
| WO (1) | WO2003024947A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| TWI394537B (zh) * | 2006-10-06 | 2013-05-01 | Takasago Perfumery Co Ltd | 風味改善劑及含有該風味改善劑的飲食品 |
| US7700788B2 (en) * | 2006-10-31 | 2010-04-20 | Battelle Memorial Institute | Hydroxymethyl furfural oxidation methods |
| DE102008009933A1 (de) | 2008-02-18 | 2009-08-20 | Friedrich-Schiller-Universität Jena | Verfahren zur Herstellung von 5-Hydroxymethylfurfural mit Hilfe von ionischen Flüssigkeiten |
| CN101619050B (zh) * | 2008-07-04 | 2011-06-22 | 中国科学院大连化学物理研究所 | 催化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 |
| JP2010083850A (ja) * | 2008-10-02 | 2010-04-15 | Kri Inc | リグノセルロースの糖化及びエタノール発酵方法 |
| EP3257845A1 (en) | 2009-05-14 | 2017-12-20 | Archer Daniels Midland Company | Preparation of 2,5-furandicarboxylic acid by oxidation of 5-(acetoxymethyl)furfural in the presence of a bromide, oxygen and a cobalt(ii) or cerium(iii) catalyst |
| US8314267B2 (en) * | 2009-06-26 | 2012-11-20 | Uop Llc | Carbohydrate route to para-xylene and terephthalic acid |
| CN101987839B (zh) * | 2009-07-31 | 2012-11-14 | 中国科学院大连化学物理研究所 | 氧化5-羟甲基糠醛制备2，5-二甲酰基呋喃的方法 |
| CN101768142B (zh) * | 2010-01-18 | 2012-04-25 | 四川大学 | 一种由碳水化合物催化合成2,5-呋喃二甲醛的方法 |
| CN102844114B (zh) * | 2010-04-15 | 2016-06-08 | 韩国生产技术研究院 | 用于从木质类生物质原料物质制备糠醛衍生物的金属催化剂组合物及利用该金属催化剂组合物的糠醛衍生物的制备方法 |
| US8324409B2 (en) | 2010-04-23 | 2012-12-04 | The Board Of Trustees Of The University Of Illinois | Efficient method for preparing 2,5-dimethylfuran |
| CN101948452B (zh) * | 2010-08-13 | 2012-11-14 | 中国科学院山西煤炭化学研究所 | 一种含纤维素的生物质生产羟甲基糠醛的方法 |
| CN101941957B (zh) * | 2010-08-13 | 2012-11-14 | 中国科学院山西煤炭化学研究所 | 一种两相法生产羟甲基糠醛的方法 |
| WO2012073251A1 (en) | 2010-11-29 | 2012-06-07 | Ganapati Dadasaheb Yadav | Preparation of 2, 5 - diformylfuran from 5 - hmf with a heterogeneous mesoporous silver containing manganese catalyst |
| EP2557176A1 (en) * | 2011-06-15 | 2013-02-13 | Evonik Degussa GmbH | Enzymatic amination |
| FR2984889B1 (fr) * | 2011-12-22 | 2017-02-24 | Roquette Freres | Procede ameliore d'oxydation selective du 5-hydromethyl furaldehyde |
| KR101217137B1 (ko) * | 2012-03-05 | 2012-12-31 | 한국생산기술연구원 | 프록토오스를 포함하는 옥수수시럽으로부터 5-히드록시메틸-2-푸르푸랄을 제조하는 방법 |
| CN103113327B (zh) * | 2013-01-24 | 2015-06-03 | 四川大学 | 一种由碳水化合物一步催化合成2,5-呋喃二甲醛的方法 |
| WO2014121513A1 (en) * | 2013-02-08 | 2014-08-14 | Rhodia Operations | Oxydation of alcohol compounds via mesostructured vpo catalysts |
| CN104981462B (zh) * | 2013-02-08 | 2018-09-04 | 罗地亚经营管理公司 | 通过介观结构的vpo催化剂氧化醇化合物 |
| FR3008409B1 (fr) * | 2013-07-15 | 2016-02-12 | Ard Sa | Procede de fabrication de furane 2,5-dicarboxaldehyde a partir d'hydroxymethylfurfural et de ses derives halogenes n'utilisant pas de catalyseur metallique |
| CN103739573A (zh) * | 2014-02-11 | 2014-04-23 | 厦门大学 | 催化转化生物质葡萄糖制备2,5-二甲酰基呋喃的方法 |
| CN103755668A (zh) * | 2014-02-11 | 2014-04-30 | 厦门大学 | 负载型v2o5催化剂催化制备2,5-二甲酰基呋喃的方法 |
| CN103819431A (zh) * | 2014-02-11 | 2014-05-28 | 厦门大学 | 分子氧辅助CuCl+KVO3协同催化制备2,5-二甲酰基呋喃的方法 |
| CN103833694B (zh) * | 2014-03-11 | 2015-07-08 | 四川大学 | 一种从二甲亚砜溶液中分离2,5-呋喃二甲醛的方法 |
| CN104098533B (zh) * | 2014-07-28 | 2016-03-02 | 常州大学 | 一种用葡萄糖制备2,5-二甲酰基呋喃的方法 |
| CN104327019A (zh) * | 2014-11-24 | 2015-02-04 | 苏州乔纳森新材料科技有限公司 | 由碳水化合物催化合成2,5-呋喃二甲醛的方法 |
| FI3283470T3 (fi) * | 2015-04-14 | 2023-12-13 | Du Pont | Menetelmiä 2,5-furaanidikarboksyylihapon ja sen johdannaisten valmistamiseksi |
| CN105175367A (zh) * | 2015-09-09 | 2015-12-23 | 江苏大学 | 一种酸催化糖转化为5-羟甲基糠醛的方法 |
| CN106008416B (zh) * | 2016-07-04 | 2019-02-19 | 浙江大学 | 一种2,5-呋喃二甲醛的制备方法 |
| EP3630739B1 (en) | 2017-05-26 | 2025-03-05 | Council of Scientific and Industrial Research | A single step process for the synthesis of furan derivatives from carbohydrates |
| EP3656766B1 (en) | 2017-07-21 | 2021-09-15 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 2,5-bis(aminomethyl)furan |
| CN109293495B (zh) * | 2018-10-15 | 2022-02-08 | 南京大学 | 一种复合相vpo催化剂及其制法和应用 |
| CN109574962B (zh) * | 2018-12-06 | 2023-05-02 | 中国科学技术大学 | 一种由糖制备2，5呋喃二甲酸的方法 |
| JP2020143046A (ja) * | 2019-03-01 | 2020-09-10 | 国立研究開発法人産業技術総合研究所 | ５−ヒドロキシメチル−２−フルフラールおよび２，５−ジホルミルフランの合成方法 |
| CN111269202B (zh) * | 2020-02-26 | 2022-04-15 | 南京林业大学 | 一种光照条件下2,5-呋喃二甲醛的制备方法 |
| CN118908916A (zh) * | 2024-07-04 | 2024-11-08 | 南京林业大学 | 一种无tempo选择性氧化5-羟甲基糠醛制备2,5-二甲酰基呋喃的方法 |
| CN119977921A (zh) * | 2025-04-15 | 2025-05-13 | 中南大学 | 一种基于酸性硫酸氧钒溶液体系催化氧化5-羟甲基糠醛生成2,5-二甲酰呋喃的方法 |
| CN120590348B (zh) * | 2025-08-07 | 2025-10-21 | 中南大学 | 基于酸性磷钒多酸混合体系催化氧化hmf生成dff的方法与电解耦合制氢工艺 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS549260A (en) | 1977-06-24 | 1979-01-24 | Noguchi Kenkyusho | Production of 2*55 furandialdehyde |
| JPS5549368A (en) | 1978-10-06 | 1980-04-09 | Noguchi Kenkyusho | Production of 2, 5-furandicarboxyaldehyde |
| FR2464260A1 (fr) * | 1979-09-05 | 1981-03-06 | Roquette Freres | Procede de fabrication du 5-hydroxymethylfurfural |
| FR2551754B1 (fr) * | 1983-09-14 | 1988-04-08 | Roquette Freres | Procede de fabrication du 5-hydroxymethylfurfural |
| 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 |
| SU1342903A1 (ru) * | 1986-01-27 | 1987-10-07 | Институт Органического Синтеза Ан Латвсср | Способ получени фуран-2,5-диальдегида |
| DE3826073A1 (de) * | 1988-07-30 | 1990-02-01 | Hoechst Ag | Verfahren zur oxidation von 5-hydroxymethylfurfural |
| FR2669635B1 (fr) * | 1990-11-22 | 1994-06-10 | Furchim | Procede de fabrication d'hydroxymethylfurfural (hmf) du purete elevee. |
| FR2669636B1 (fr) | 1990-11-22 | 1994-05-20 | Furchim | Procede de fabrication de furane 2,5-dicarboxaldehyde. |
| FR2727966A1 (fr) * | 1994-12-07 | 1996-06-14 | Agrichimie Sa | Procede de fabrication selective de furanedicarboxaldehyde-2 ,5 a partir de l'hydroxymethyl-5 furane carboxaldehyde-2 |
| DE19615878A1 (de) | 1996-04-22 | 1997-10-23 | Episucres Sa | Verfahren zum selektiven Herstellen von Furandicarboxaldehyd-2,5 ausgehend von Hydroxymethyl-5-Furancarboxaldehyd 2 |
-
2002
- 2002-09-13 US US10/243,337 patent/US6706900B2/en not_active Expired - Fee Related
- 2002-09-17 KR KR10-2004-7003860A patent/KR20040044933A/ko not_active Withdrawn
- 2002-09-17 CN CNA028182065A patent/CN1555368A/zh active Pending
- 2002-09-17 JP JP2003528795A patent/JP2005506984A/ja active Pending
- 2002-09-17 WO PCT/US2002/029464 patent/WO2003024947A1/en not_active Ceased
- 2002-09-17 EP EP02763644A patent/EP1427715B1/en not_active Expired - Lifetime
- 2002-09-17 DE DE60211535T patent/DE60211535T2/de not_active Expired - Fee Related
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