CA2956953C - Heterogeneous ruthenium-based catalyst and process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural in water - Google Patents
Heterogeneous ruthenium-based catalyst and process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural in water Download PDFInfo
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- CA2956953C CA2956953C CA2956953A CA2956953A CA2956953C CA 2956953 C CA2956953 C CA 2956953C CA 2956953 A CA2956953 A CA 2956953A CA 2956953 A CA2956953 A CA 2956953A CA 2956953 C CA2956953 C CA 2956953C
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- Prior art keywords
- hmf
- catalyst
- acid
- hydroxymethylfurfural
- oxidation
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- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract description 188
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 title claims abstract description 183
- 239000003054 catalyst Substances 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 79
- 230000008569 process Effects 0.000 title claims abstract description 68
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 title claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 31
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052707 ruthenium Inorganic materials 0.000 title claims abstract description 18
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 79
- 230000003647 oxidation Effects 0.000 claims abstract description 77
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000001301 oxygen Substances 0.000 claims abstract description 31
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- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 18
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- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 1
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- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- 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
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462038923P | 2014-08-19 | 2014-08-19 | |
| US62/038,923 | 2014-08-19 | ||
| PCT/US2015/043710 WO2016028488A1 (en) | 2014-08-19 | 2015-08-05 | Catalyst and process for producing 2,5-furandicarboxylic acid from hydromethylfurfural in water |
Publications (2)
| Publication Number | Publication Date |
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| CA2956953A1 CA2956953A1 (en) | 2016-02-25 |
| CA2956953C true CA2956953C (en) | 2021-06-29 |
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|---|---|---|---|
| CA2956953A Active CA2956953C (en) | 2014-08-19 | 2015-08-05 | Heterogeneous ruthenium-based catalyst and process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural in water |
Country Status (12)
| Country | Link |
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| EP (2) | EP4086243A1 (enExample) |
| JP (1) | JP6695322B2 (enExample) |
| KR (1) | KR102196777B1 (enExample) |
| CN (1) | CN106795130B (enExample) |
| AU (1) | AU2015303871B2 (enExample) |
| BR (1) | BR112017003159B1 (enExample) |
| CA (1) | CA2956953C (enExample) |
| ES (1) | ES2911178T3 (enExample) |
| HU (1) | HUE058236T2 (enExample) |
| MX (1) | MX391893B (enExample) |
| WO (1) | WO2016028488A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2017190316A (ja) * | 2016-04-15 | 2017-10-19 | 三菱ケミカル株式会社 | ２，５−フランジカルボン酸の精製方法 |
| 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 |
| CN106565647B (zh) * | 2016-10-29 | 2020-01-10 | 华东理工大学 | 一种催化氧化5-羟甲基糠醛制备2,5-呋喃二甲酸的方法 |
| EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
| CN112830915B (zh) * | 2019-11-19 | 2021-11-23 | 中国科学院宁波材料技术与工程研究所 | 一种2,5-呋喃二甲酸的低温制备方法 |
| IT201900025096A1 (it) | 2019-12-20 | 2021-06-20 | Novamont Spa | Processo per la sintesi di acido 2,5-furandicarbossilico |
| CN113117705B (zh) * | 2019-12-31 | 2024-05-07 | 中国石油化工股份有限公司 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
| CN113117706B (zh) * | 2019-12-31 | 2024-04-12 | 中国石油化工股份有限公司 | 一种金属改性的钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
| FR3109778A1 (fr) * | 2020-04-29 | 2021-11-05 | IFP Energies Nouvelles | Procede d’oxydation du 5-hydroxymethylfurfural |
| ES2924086T3 (es) * | 2020-05-15 | 2022-10-04 | Archer Daniels Midland Co | Producción conjunta de monómeros, incluyendo al menos un monómero de base biológica |
| CN116063258B (zh) * | 2021-10-29 | 2025-03-11 | 中国石油化工股份有限公司 | 一种连续生产5-羟甲基糠醛和2,5-呋喃二甲酸的方法 |
| CN117504932B (zh) * | 2023-11-10 | 2025-06-17 | 广东省科学院生物与医学工程研究所 | 一种多功能纳米碳催化剂及其催化碳水化合物合成2,5-呋喃二甲酸的方法 |
| CN117843596A (zh) * | 2023-12-20 | 2024-04-09 | 中科国生(杭州)科技有限公司 | 一种5-氯糠酸的制备方法 |
| CN118894822A (zh) * | 2024-06-17 | 2024-11-05 | 清华大学 | 5-羟甲基糠醛氧化制备2,5-呋喃二甲酸的方法及应用 |
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| GB621971A (en) | 1946-11-12 | 1949-04-25 | James Gordon Napier Drewitt | Improvements in polymers |
| JPH03130247A (ja) * | 1989-10-16 | 1991-06-04 | Mitsui Petrochem Ind Ltd | 芳香族カルボン酸の製造方法 |
| US5622655A (en) | 1995-04-10 | 1997-04-22 | Hydro-Thermal Corporation | Sanitary direct contact steam injection heater and method |
| US5842497A (en) | 1996-05-20 | 1998-12-01 | Hydro-Thermal Corporation | Adjustable shear direct contact steam injection heater |
| US6082712A (en) | 1998-07-09 | 2000-07-04 | Hydro-Thermal Corporation | Direct contact steam injection heater |
| US7317116B2 (en) | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
| US7152851B2 (en) | 2005-02-04 | 2006-12-26 | Hydro-Thermal Corporation | Steam injection heater with dual-sealing assembly |
| US7678950B2 (en) | 2005-12-16 | 2010-03-16 | Conocophillips Company | Process for converting carbohydrates to hydrocarbons |
| US7700788B2 (en) | 2006-10-31 | 2010-04-20 | Battelle Memorial Institute | Hydroxymethyl furfural oxidation methods |
| BRPI0813157B1 (pt) | 2007-06-18 | 2017-12-12 | Archer Daniels-Midland Company | Method of purification of hmf from a mixture containing reagents and products of the synthesis of hmf from fruit |
| JP5207677B2 (ja) | 2007-07-17 | 2013-06-12 | キヤノン株式会社 | ２，５−フランジカルボン酸の製造方法 |
| EP2944632A1 (en) | 2007-12-12 | 2015-11-18 | Archer Daniels Midland Co. | Oxidation of a mixture of 2-hydroxymethyl-5-furfuraldehyde (hmf) and an ester thereof to 2,5-furandicarboxylic acid (fdca) |
| US8558018B2 (en) * | 2009-05-14 | 2013-10-15 | Archer Daniels Midland Company | Oxidation of furfural compounds |
| DE102009028975A1 (de) | 2009-08-28 | 2011-03-03 | Evonik Oxeno Gmbh | Esterderivate der 2,5-Furandicarbonsäure und ihre Verwendung als Weichmacher |
| DE102009028976A1 (de) | 2009-08-28 | 2011-03-03 | Evonik Oxeno Gmbh | Ester der 2,5-Furandicarbonsäure mit isomeren Decanolen und ihre Verwendung |
| CA2775319C (en) | 2009-10-07 | 2018-08-28 | Furanix Technologies B.V. | Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicarboxylic acid |
| US20140343305A1 (en) * | 2011-08-31 | 2014-11-20 | The University Of Kansas | Process for producing both biobased succinic acid and 2,5-furandicarboxylic acid |
| PT2750789T (pt) | 2011-08-31 | 2018-10-30 | Archer Daniels Midland Co | Processo de oxidação em spray para produzir ácido 2,5- furandicarboxílico a partir de hidroxi-metilfurfural |
| CN104053649A (zh) | 2012-01-10 | 2014-09-17 | 阿彻丹尼尔斯米德兰德公司 | 从糖类制备hmf和hmf衍生物同时回收适合于直接发酵为乙醇的未反应糖类的方法 |
| JP2013203666A (ja) * | 2012-03-27 | 2013-10-07 | Kao Corp | ５−ヒドロキシメチルフルフラール酸化物の製造方法 |
| 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 |
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2015
- 2015-08-05 AU AU2015303871A patent/AU2015303871B2/en active Active
- 2015-08-05 ES ES15834376T patent/ES2911178T3/es active Active
- 2015-08-05 MX MX2017002188A patent/MX391893B/es unknown
- 2015-08-05 EP EP22161787.1A patent/EP4086243A1/en not_active Withdrawn
- 2015-08-05 BR BR112017003159-0A patent/BR112017003159B1/pt active IP Right Grant
- 2015-08-05 KR KR1020177007369A patent/KR102196777B1/ko active Active
- 2015-08-05 JP JP2017505641A patent/JP6695322B2/ja active Active
- 2015-08-05 HU HUE15834376A patent/HUE058236T2/hu unknown
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- 2015-08-05 EP EP15834376.4A patent/EP3183241B1/en active Active
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- 2015-08-05 WO PCT/US2015/043710 patent/WO2016028488A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| HUE058236T2 (hu) | 2022-07-28 |
| KR20170040807A (ko) | 2017-04-13 |
| CA2956953A1 (en) | 2016-02-25 |
| US9957244B2 (en) | 2018-05-01 |
| ES2911178T3 (es) | 2022-05-18 |
| MX391893B (es) | 2025-03-21 |
| US20170217917A1 (en) | 2017-08-03 |
| CN106795130A (zh) | 2017-05-31 |
| EP3183241B1 (en) | 2022-03-16 |
| BR112017003159B1 (pt) | 2021-10-05 |
| AU2015303871A1 (en) | 2017-02-23 |
| JP2017525689A (ja) | 2017-09-07 |
| AU2015303871B2 (en) | 2018-11-29 |
| KR102196777B1 (ko) | 2020-12-30 |
| JP6695322B2 (ja) | 2020-05-20 |
| CN106795130B (zh) | 2021-01-22 |
| EP3183241A4 (en) | 2018-01-24 |
| BR112017003159A2 (pt) | 2017-11-28 |
| WO2016028488A1 (en) | 2016-02-25 |
| EP3183241A1 (en) | 2017-06-28 |
| EP4086243A1 (en) | 2022-11-09 |
| MX2017002188A (es) | 2017-05-03 |
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