WO2010132740A2 - Oxidation of furfural compounds - Google Patents
Oxidation of furfural compounds Download PDFInfo
- Publication number
- WO2010132740A2 WO2010132740A2 PCT/US2010/034856 US2010034856W WO2010132740A2 WO 2010132740 A2 WO2010132740 A2 WO 2010132740A2 US 2010034856 W US2010034856 W US 2010034856W WO 2010132740 A2 WO2010132740 A2 WO 2010132740A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- furan
- furfural
- reaction mixture
- hmf
- solvent
- Prior art date
Links
- 0 *OC(c1ccc(C(O)=O)[o]1)=O Chemical compound *OC(c1ccc(C(O)=O)[o]1)=O 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
- C07D307/56—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
Definitions
- the invention pertains to processes for oxidation of furan aldehydes such as 5-
- HMF hydroxymethylfurfural
- DFF 2,5-diformylfuran
- ether derivatives of HMF such as 5-(alkoxymethyl)furfural (AMF), 5- (aryloxymethyl)furfural, 5-(cycloalkoxymethyl)furfural and 5-(acyloxymethyl)furfural compounds to form ester-acid derivatives of HMF, particularly 5-(alkoxycarbonyl)furan-2- carboxyiic acids.
- the oxidations are done or in the presence of dissolved oxygen and a Co(II), Mn(II), Ce(III) salt catalyst or mixtures thereof with or without bromide and with or without an aliphatic ketone to selectively form the desired compounds.
- the products can be further oxidized for form 2,5 furandicarboxylic acid (FDCA).
- HMF is an important compound with many industrial applications such as use in polymers, solvents, surfactants, pharmaceuticals, and plant protection agents.
- the oxidation derivatives of HMF also have important commercial value.
- 2,5 diformylfuran (DFF) has various useful applications such as a monomer; as a starting material for the synthesis of drugs, antifungal agents, nematocides and ligands; in photography; and as a cross- linking agent for polyvinyl alcohol.
- DFF diformylfuran
- 2,5 furandicarboxylic acid a.k.a.
- furandiacid (FDCA a.k.a FDA) represents one key intermediate substance and is a suitable starting source for the formation of various furan monomers required for the preparation of non-petroleum-derived polymeric materials.
- FDCA a.k.a FDA furandiacid
- Many methods have been proposed for making DFF and FDCA. However, these reactions provide low yields, poor selectivity and are not environmentally friendly. For example, it is known that the synthesis of DFF from fructose can be done in a two step process, namely, by dehydration of fructose in a high boiling solvent such as dimethylsulfoxide (DMSO) to form HMF, followed by in situ catalytic air oxidation also in the presence of DMSO to form a mixture of DFF, FDCA and various other reaction side products.
- DMSO dimethylsulfoxide
- DFF or FDCA could be made from HMF by oxidation in the presence of dissolved oxygen at about 1000 psi, and a catalyst system containing Co(II), Mn(II), and a Br salt preferentially also including Zi (W. Partenhemier & V Grushin: Adv. Synth. Catal. (2001) 343, 102-11 1).
- the selectivity for DFF was at most 69% in a catalyst system of Co/Mn/Br, and at most 73%. in a catalyst system of Co/Mn/Br/Zr.
- the best selectivity for FDCA was 73% in a catalyst system of Co/Mn/Br/Zr and at most about 35% with the same catalyst system but without the Zr.
- the ability to convert HMF into one predominant oxidation product is difficult due to the reactivity of the aldehyde and alcohol moieties of the HMF molecule.
- selectivity between DFF and FDCA as the predominant product was affected by using lower reaction temperatures (50- 75 0 C) for making DFF, and higher reaction temperatures for making FDCA (typically 100- 125 0 C).
- FDCA is a difficult product to handle. It tends to precipitate in solvents used for oxidation when the temperature is raised and tends to co-precipitate with side products. It would be beneficial if an FDCA precursor could be made that is easy to separate and which could subsequently be converted to FDCA in a different reaction. Also it would be beneficial to find other routes to selective preparation of DFF versus FDCA by oxidative methods. The present invention provides for these and other needs that will be apparent from the description that follows.
- the present invention is based at least in-part, on the surprising discovery that 5-ethers of HMF can be simultaneously oxidized at the ether linkage and at aldehyde to form 5-ester furanic acids, (i.e., 5-alkoxycarbonylfurancarboxylic acids, furan-2,5-dicarboxylic acid monoesters, a.k.a. 5-alkoxycarbonylfuran 2-carboxylic acids) using a catalyst system comprised of Co(II), Mn(II) and Ce(III) salts.
- These ester compounds are easy to separate by conventional solvent extraction or distillation and can be subsequently converted to FDCA under mild hydrolysis conditions.
- HMF can be selectively converted to DFF by the inclusion of a aliphatic ketone, exemplified by methyl ethyl ketone (MEK).
- MEK methyl ethyl ketone
- FDCA can be selectively made from HMF at greater than 40% by the inclusion of bromide in the reaction mixture.
- selective production of FDCA can occur without need for a zirconium co- catalyst in the reaction mixture.
- HMF can be converted to FDCA using only cobalt, or only cerium salts in the presence of bromide, without the need for manganese or zirconium co-catalyst.
- the present invention provides methods of oxidizing furan aldehydes that includes heating the furan aldehyde in a reaction mixture comprising a solvent containing dissolved oxygen and at least one catalyst selected from the group consisting of Co(II), Mn(II) and Ce(III) salts. If the furan aldehyde is -5-(hydroxymethyl)furfural, the reaction mixture includes a aliphatic ketone which helps make the predominant reaction product of diformylfuran.
- the predominant reaction product is at least one of a 5- ester furan 2-acid and a 5-(alkoxycarbonyl)furfuraL Moreover, if the furan aldehyde is a 5-(alkoxycarbonyl)furfural the predominant reaction product is the 5- ester furan 2-carboxylic acid, meaning that under prolonged reaction conditions, even if 5-(alkoxycarbonyl)furfural or 5-(alkoxymethyl)furoic acid is made from the furan ether aldehyde, intermediate furan can further be oxidized to the ester - acid derivative.
- the 5-ether of the furan aldehyde can be any ether, especially including a 5- (alkoxymethyl)furfural, a 5-(aryloxymethyl)furfural, and a 5-(cycloalkoxymethyl)furfural. Examples are provided when the furan aldehyde is HMF, and where the 5-ether of the furan aldehyde is 5-(acetoxymethyl)furfural and 5-(butoxymethyl)furfural.
- the reaction mixture is heated to a temperature of between 80 0 C and 130 0 C at a pressure of oxygen or air of about 600-to about 1000 psi for a time sufficient to form the predominant reaction product.
- the temperature is between 100 0 C and 125 0 C, and most typically is about 120 0 C.
- Air or oxygen can be used under the pressure conditions to supply oxygen to the reaction mixture.
- the reaction mixture contains acetic acid as a principle solvent
- the predominant reaction product is at least 80% of the reaction products.
- the predominant reaction product is a 5- ester furan 2- carboxylic acid which can be collected by precipitation from, or evaporation of the reaction mixture in a first purification step.
- the precipitate is dissolved in a solvent in which the predominant product has higher solubility than FDCA. in a second purification step.
- Suitable solvents include, but are not limited to: ethyl acetate, dimethylformamide, dimethylacetate, tetrahydrofuran, dioxane, methyl ethyl ketone, methyl isobutyl ketone, acetonitrile, methyltetrahydrofuran, and C1-C6 alcohols.
- the catalyst salt can have any typical anion partner, such as acetate, acetate hydrate, bromide, chloride, fluoride, iodide, alkoxide, azide, oxalate, carbonate, carboxylate, hydroxide, nitrate, borate, oxide, acetylacetonate and mixtures thereof.
- anion partner such as acetate, acetate hydrate, bromide, chloride, fluoride, iodide, alkoxide, azide, oxalate, carbonate, carboxylate, hydroxide, nitrate, borate, oxide, acetylacetonate and mixtures thereof.
- the reaction mixture can include CO 2 expanded in the principle solvent of the reactions mixture, for example, CO 2 expanded acetic acid.
- the CO 2 should be expanded in the solvent at a pressure of at least 100 psi.
- the oxygen is provided by oxygen gas or air dissolved in the solvent at a pressure of at least 200 psi and CO 2 is expanded in the solvent at a pressure of at 100 psi, typically 100-200 psi.
- the reaction mixture may also include bromide when it is desirable to form FDCA as .a co- product of the oxidizing in which case, under prolonged conditions, FDCA can become the predominant product when HMF, or even the ether derivative of HMF is the reactant. Conversely, and the reaction mixture omits bromide, contains methyl ethyl ketone with HMF as the reactant, the predominant reaction product is DFF.
- the invention is directed to a low cost and environmentally friendly method for oxidation of a furfural compounds in the presence of oxygen in a reaction mixture containing at least one of Co(II), Mn(II), Ce(III) salt catalysts according to the following reaction scheme:
- R represents H, alkyl, aryl, acyl, cycloalkyl or alkylcarbonyl.
- derivatives of particular interest are the oxidized forms of HMF, in which HMF is selectively oxidized to form 2,5-diformylfuran (DFF) or 2,5-furandicarboxylic acid (FDCA).
- DFF 2,5-diformylfuran
- FDCA 2,5-furandicarboxylic acid
- oxidation of AMF can also readily be achieved using the same catalyst as used for oxidizing HMF.
- the major resulting product is surprisingly found to be ester derivative a 5 — (alkoxycarbonyl)furancarboxcylic acid (AcMF) where the alkoxymethyl ether linkage has been oxidized to an ester and while the furan aldehyde is oxidized to the acid shown at the right of the reaction below.
- ester derivative unlike FDCA, the ester derivative is readily soluble in a variety of organic compounds while FDCA is highly insoluble.
- the ester derivatives can readily be hydrolyzed in the presence of acid or base catalysts, or further oxidized to provide FDCA when FDCA is ultimately the desired product. Because the differential solubility and ease of handling, formation of the ester acid derivative can improve upstream purification processes and yields when it is desired to ultimately obtain FDCA.
- HMF (crude or pure) is heated in a solvent in the presence of Co(II) and/or Mn(II) salt catalysts with dissolved oxygen or air.
- the reaction can proceed to selectively form 2,5-diformylfuran (DFF) by inclusion of an aliphatic ketone, like methyl ethyl ketone and omission of a bromide promoter in the reaction mixture.
- DFF 2,5-diformylfuran
- FDCA 2,5-furandicarboxylic acid
- Higher reaction temperatures will drive the reaction to carboxylic acids.
- CXL CO 2 expanded liquid
- a CXL is generated by mixing nontoxic, nonflammable carbon dioxide with either a conventional organic solvent or a binary mixture of the organic solvent and water to form a single-phase liquid.
- the resulting CXL greatly reduces the potential for forming explosive vapors and possesses properties desirable as a medium for performing catalytic reactions.
- CXLs improve the solubility of liquid and gaseous reactants, as well as catalysts salts, and improve mass transfer compared to traditional pure liquid-phase reactions. Additionally, CXLs reduce the usage of organic solvents and thereby the emissions of organic vapors into the atmosphere. For these reasons, CXL solvents are attractive for many reactions.
- solvents are miscible and can be expanded with CO 2 .
- Preferred solvents for the reactions of the present invention are polar organic solvents, which include, but are not limited to, carboxylic acids such as acetic acid and alcohols such as ethanol and methanol, and organic solvents such as acetonitrile, acetone, n-methylpyrrolidinone, methylene chloride, methyl ethyl ketone, methyl isobutyl ketone or combinations thereof. Aqueous mixtures of these solvents may also be included. .
- the reaction includes one or more Co(II), Mn(II), Ce(III) salt catalysts.
- the anion of salts can be in many forms, typically those selected from the group consisting of an acetate, acetate hydrate, bromide, chloride, fluoride, iodide, alkoxide, azide, oxalate, carbonate, carboxylate, hydroxide, nitrate, borate, oxide, acetylacetonate salts of cobalt, cerium and manganese.
- the acetate salt of Co(II) in combination with Mn(II) are used in most of the exemplary embodiments disclosed herein, however, Co(II) alone or Ce(III) are also shown to work, and other slats of one or more of these metals in various combinations should also catalyze the oxidation reactions.
- zirconium is not required for selective oxidation to FDCA at high molar yields
- Catalyst systems containing only cobalt and bromide or only cerinium and bromide, or the combination of cobalt, manganese and bromide salts can all make FDCA at high molar yields.
- the mixture is heated, typically to between 100-130 0 C, more typically between 110-125 0 C, and most typically to about 120 0 C under mild pressure (typically 800- 1000 psi), and the reactions proceed rapidly.
- the oxidization to FDCA can be advantageously achieved by using dense CXLs.
- Dense CXLs refers to the production of CO 2 expanded liquids by condensing relatively large amounts of CO 2 into fixed amounts of a polar organic solvent. Typically the CO 2 is expanded into the principle solvent of the reaction mixture at 100-200 psi. The advantage is that a large amount of CO 2 favors oxygen solubility while polar organic solvents favor catalyst solubility. The combination of dense CO 2 and polar organic solvents enables mild conditions and reasonable reaction times. Thus, the method of present invention allows for a cost effective approach towards the synthesis of FDCA from HMF.
- the reaction should occur under milder conditions.
- conditions to form DFF from HMF without the use of CO 2 expanded acetic acid solvent uses pressures of at least about 800-1000 psi oxygen as shown in Examples 1-4.
- the pressure can be lowered to 100- 200 psi oxygen and 100-200 psi CO 2 .
- the amount of organic solvent is reduced leading to an environmentally friendly and efficient process.
- the solubility of oxygen in the CO 2 -expanded liquid is improved by the presence of CO 2 resulting in shorter reaction times.
- a sugar can be converted directly to DFF.
- HMF can be obtained from sugar sources including crystalline fructose and high fructose corn syrup.
- HMF is prepared by dehydrating a sugar in the presence of an sulfuric acid and a organic solvents such as acetonitrile, acetone, N-methylpyrrolidinone (NMP), methylene chloride, dimethylacetamide, and dimethylformamide for 1 to 3 hours at a temperature from about 170 to about 250 0 C and then oxidized to DFF in the presence of oxygen, methyl ethyl ketone and the Co/Mn catalysts as set forth in the reaction scheme (III) below:
- the starting material can be ethers of HMF including any of 5-(aryloxymethyl)furfural, 5-(cycloalkoxy-methyl)furfural and 5- (alkoxycarbonyl)furfural. These starting materials can be in a pure or crude form.
- the reaction conditions are substantially the same as those for the oxidation of HMF to FDCA and surprisingly proceeds to an ester acid derivative in accordance with the following reaction scheme.
- R represents H, alkyl, aryl, cycloalkyl or alkylcarbonyl.
- the resulting ester acids can be easily purified from the reaction mixture by precipitation from, or evaporation of the reaction mixture.
- the precipitation can be conducted by lowering the reaction mixture to room temperature or below for a time sufficient to precipitate the ester furan acid derivative in a first purification step. Any FDCA formed in the reaction mixture will tend to co precipitate with the ester furan acid derivative, however, FDCA is not as soluble in many solvents as the ester furan acid. Accordingly, a second purification step is to redissolve the precipitate in a solvent in which FDCA is less soluble than the ester furan acid derivative.
- Suitable solvents include, but are not limited to, ethyl acetate, dimethylformamide, dimethylacetate, tetrahydrofuran, dioxane, methyl ethyl ketone, methyl isobutyl ketone, acetonitrile, methyltetrahydrofuran, and C1-C6 alcohols.
- the recovered ester furan acid derivative can be subsequently hydrolyzed in the presence of a heterogenous or homogenous acid or base catalyst , or subsequently further oxidized to yield FDCA and the R-alcohol co- product, which can be recovered for reuse.
- a reaction mixture containing 97% purity HMF (5.0 g), acetic acid (50 mL), cobalt acetate (0.97 g), manganese acetate (0.98 g), and methyl ethyl ketone (1.90 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at 12O 0 C for 3.5 hours.
- the sample was spotted on TLC plates (K5F Whatman) and developed in 1 :1 EtOAc/hexane and visualized under UV light. Visual analysis indicated that after 3.5 hours, substantially all of the HMF was converted.
- the reaction mixture (58.58 g) was found to contain 46,356g/kg DFF (86%), 2,908 g/kg FFCA (5%), 4,201 g/kg HMF (8%) and 62 g/kg FDCA (1%) for a DFF selectivity of 86%.
- a reaction mixture containing 97% purity HMF (5.08 g), acetic acid (50 mL), cobalt acetate (0.973 g), manganese acetate (0.982 g), and methyl ethyl ketone (0.89 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at 120 0 C for 4.5 hours.
- the reaction mixture (49.76 g) contained 41,368 mg/kg DFF (87%), 3,344 mg/kg FFCA, 2,671 mg/kg HMF and 32 mg/kg FDCA.
- Product selectivity of DFF was 87%.
- Example 3 A reaction mixture containing 97% purity HMF (10.04 g), acetic acid (50 mL), cobalt acetate (1.94 g), manganese acetate (1.94 g), and methyl ethyl ketone (1.78 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at 12O 0 C for 4 hours. Samples were taken at 2 and 4 hours and analyzed by LCMS.
- a reaction mixture containing 97% purity HMF (5.0 g), acetic acid (50 mL), cobalt acetate (0.97 g) and methyl ethyl ketone (0.89 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at about 12O 0 C for 4 hours.
- Example 7 A reaction mixture containing 97% purity HMF (5.02 g), acetic acid (50 mL), cobalt acetate (0.97 g), manganese acetate (0.98 g), and methyl ethyl ketone (1.90 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at a temperature that varied between 120 - 14O 0 C for 3 hours.
- a reaction mixture containing 97% purity HMF (5.02 g), acetic acid (50 mL), cobalt acetate (0.97 g), manganese acetate (0.98 g), and methyl ethyl ketone (0.85 mL) was placed in a 100 mL reactor and subjected to 1000 psi oxygen that varied between 120 - 140 0 C for 6 hours.
- a reaction mixture containing 97% purity HMF (5 g), acetic acid (50 mL), cobalt acetate (0.165 g), cerium acetate (0.162 g), and sodium bromide (0.142 g) was placed in a 100 mL reactor and subjected to 400 psi oxygen at 100 0 C for 1.5 hours. A precipitate was formed. Samples of the liquid were taken every 30 minutes and subjected to LCMS analysis.
- a reaction mixture containing 97% purity HMF (5.00 g), acetic acid (50 mL), cobalt acetate (0.97 g), manganese acetate (0.97 g), and methyl ethyl ketone (0.89 mL) was placed in a 100 mL reactor and subjected to 1000 psi air at 115C for 4 hours.
- a sample taken at 4 hours was subjected to TLC analysis as described in example 1. Visual analysis indicated partial conversion of HMF to DFF and the AcHMF ether. The temperature was then increased to 125C for an additional 2 hours. The catalysts were removed by filtration and the solvent evaporated. The product was washed with water to give a cream colored solid.
- This example illustrates a simple method of DFF purification.
- a reaction mixture that was obtained from example 1 was allowed to evaporate.
- the resulting material was dissolved in diethyl ether with heating and the liquid was decanted from the black waxy material.
- the ether solution was cooled and a precipitate formed.
- the precipitate was removed by filtration and dried under vacuum.
- 1 H NMR analysis indicates substantially pure DFF.
- GC/MS: m/z 124..
- the reaction mixture contained 2292 mg/kg FDCA (2%), 27035 mg/kg FFCA (28%), 4151 mg/kg HMF (4%), and 64251 mg/kg DFF (66%).
- temperature was found to effect product selectivity.
- a reaction mixture containing 82% butoxymethylfurfural (6.12 g), acetic acid (70 mL), cobalt acetate (0.165 g), manganese acetate (0.169 g), and sodium bromide (0.142 g) was placed in a 100 mL reactor and subjected to 1000 psi oxygen at 100 0 C for 5 hours.
- a reaction mixture containing 80% butoxymethylfurfural (12.19 g), acetic acid (50 mL), cobalt acetate (0.165 g), manganese acetate (0.165 g), and sodium bromide (0.142 g) was placed in a 100 mL reactor and subjected to 600 psi oxygen at 100 0 C for 5 hours. Samples were taken at 0.5 and 1 h and analyzed by TLC as described in example 1. Visual analysis of TLC plate with UV light indicated that after 1 h, essentially all of the BMF was converted to 5-(butoxycarbonyl)furan-2-carboxylic acid. GC/MS analysis confirmed these results (m/z 157, 139, 56. After the reaction was completed, the precipitated solid was removed by filtration and analyzed by 1 H NMR. Substantially pure 5-(butoxycarbonyl)furan-2-carboxylic acid (1.88 g) was recovered.
- a reaction mixture containing acetoxymethylfurfural (5.0 g), acetic acid (50 mL), cobalt acetate (0.13 g), manganese acetate (0.13 g), and sodium bromide (0.11 g) was placed in a 100 mL reactor and subjected to 500 psi oxygen at IOOC for 2 hours.
- the solid (2.53 g) was removed by filtration to give a 54% molar yield of FDCA from AcFIMF and a 5- (xcetoxymethyl)furan-2-carboxylic acid (AcMFCA) by-product.
- a reaction mixture that was obtained from example 5, was allowed to evaporate. The resulting material was placed in a mixture of water (25 mL) and ethyl acetate (25mL). A solution of 4.0M HCl in dioxane was added dropwise to lower the pH to ⁇ 2. The two layers were allowed to separate. The aqueous layer was washed with ethyl acetate and the organic layers combined and dried over MgSO 4 . Following filtration of the MgS ⁇ 4 , the solvent was removed by rotary evaporation. 1 H NMR and GC/MS data revealed conversion of BMF to the ester/acid m/z 157, 139, 56 in high purity (>90%).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10775584.5A EP2430010B1 (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
EP14172600.0A EP2784069B2 (en) | 2009-05-14 | 2010-05-14 | Oxidation of 5-alkoxy-furfural to 5-(alkoxycarbonyl)furan-2-carboxylic acid |
ES10775584.5T ES2542972T3 (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
EP16177758.6A EP3133064B1 (en) | 2009-05-14 | 2010-05-14 | Process for the preparation of 2,5-furandicarboxylic acid (fdca) by oxidation of 5-(alkyloxymethyl)furfural (amf) with oxygen in the presence of a co(ii) or ce(iii) catalyst, a bromide salt and a solvent |
BRPI1007729-4A BRPI1007729A2 (en) | 2009-05-14 | 2010-05-14 | Oxidation Method of Furanic Villages |
PL10775584T PL2430010T3 (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
CN201080026027.8A CN102459214B (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
BR122017024876-6A BR122017024876B1 (en) | 2009-05-14 | 2010-05-14 | oxidation method of furan aldehydes |
US13/319,877 US8558018B2 (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17830109P | 2009-05-14 | 2009-05-14 | |
US61/178,301 | 2009-05-14 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2010132740A2 true WO2010132740A2 (en) | 2010-11-18 |
WO2010132740A3 WO2010132740A3 (en) | 2011-03-31 |
Family
ID=43085592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2010/034856 WO2010132740A2 (en) | 2009-05-14 | 2010-05-14 | Oxidation of furfural compounds |
Country Status (8)
Country | Link |
---|---|
US (1) | US8558018B2 (en) |
EP (5) | EP2862858A1 (en) |
CN (2) | CN104744414B (en) |
BR (2) | BRPI1007729A2 (en) |
ES (2) | ES2730100T3 (en) |
PL (1) | PL2430010T3 (en) |
TR (1) | TR201908177T4 (en) |
WO (1) | WO2010132740A2 (en) |
Cited By (71)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011043661A1 (en) * | 2009-10-07 | 2011-04-14 | 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 |
WO2012161970A2 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161972A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161968A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161973A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2013062408A1 (en) | 2011-10-24 | 2013-05-02 | Furanix Technologies B.V. | A process for preparing a polymer product having a 2,5-furandicarboxylate moiety within the polymer backbone to be used in bottle, film or fibre applications |
WO2013093322A1 (en) * | 2011-12-22 | 2013-06-27 | Roquette Freres | Improved method for selectively oxidizing 5-hydroxymethyl furaldehyde |
WO2014014979A1 (en) * | 2012-07-20 | 2014-01-23 | Eastman Chemical Company | An oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US8658810B2 (en) | 2012-06-22 | 2014-02-25 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate vapor |
WO2014035813A1 (en) * | 2012-08-30 | 2014-03-06 | Eastman Chemical Company | An oxidation process to produce a crude dry carboxylic acid product |
WO2012161971A3 (en) * | 2011-05-24 | 2014-05-08 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
US8748479B2 (en) | 2012-06-22 | 2014-06-10 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
WO2014102413A1 (en) * | 2012-12-26 | 2014-07-03 | Consejo Superior De Investigaciones Científicas (Csic) | Method for producing organic molecules used as novel surfactant agents |
EP2751060A2 (en) * | 2011-08-31 | 2014-07-09 | The University Of Kansas | Process for producing both biobased succinic acid and 2,5-furandicarboxylic acid |
WO2014140398A1 (en) * | 2013-03-12 | 2014-09-18 | Consejo Superior De Investigaciones Científias (Csic) | Preparation of organic molecules which can be used as surfactants |
NL2010572C2 (en) * | 2013-04-05 | 2014-10-07 | Furanix Technologies Bv | Process for the preaparation of 2,5-furan-dicarboxylic acid. |
US8859788B2 (en) | 2012-06-22 | 2014-10-14 | Eastman Chemical Company | Esterification of furan-2,5-dicarboxylic acid to a dialkyl-furan-2,5-dicarboxylate vapor with rectification |
US8912349B2 (en) | 2012-06-22 | 2014-12-16 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate separation and solid liquid separation |
US8916720B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
US8916719B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
WO2014204313A1 (en) | 2013-06-20 | 2014-12-24 | Furanix Technologies B.V. | Process for the preparation of a fiber, a fiber and a yarn made from such a fiber |
US8969404B2 (en) | 2012-06-22 | 2015-03-03 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
WO2015056270A1 (en) | 2013-10-17 | 2015-04-23 | Natco Pharma Limited | Process for the preparation of 2,5-furandicarboxylic acid |
US9029580B2 (en) | 2012-07-20 | 2015-05-12 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
WO2015137805A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Polyester and method for preparing such a polyester |
WO2015137804A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Method for preparing a polyester under specific esterification conditions |
WO2015137807A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Polyester and method for preparing such a polyester |
WO2015137806A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Process for enhancing the molecular weight of a polyester |
US9156805B2 (en) | 2012-11-20 | 2015-10-13 | Eastman Chemical Company | Oxidative purification method for producing purified dry furan-2,5-dicarboxylic acid |
WO2015155784A1 (en) | 2014-04-09 | 2015-10-15 | Natco Pharma Limited | Process for the preparation of 2,5-furandicarboxylic acid and its ester derivative |
US9199958B2 (en) | 2011-05-24 | 2015-12-01 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US9321744B1 (en) | 2015-06-26 | 2016-04-26 | Industrial Technology Research Institute | Method for preparing 2,5-furan dicarboxylic acid |
JP2016513641A (en) * | 2013-03-14 | 2016-05-16 | アーチャー−ダニエルズ−ミッドランド カンパニー | Method for producing 2,5-furandicarboxylic acid |
EP2784069B1 (en) | 2009-05-14 | 2016-07-06 | Archer-Daniels-Midland Company | Process for the oxidation of 5-(alkoxymethyl)furfural to 5-(alkoxycarbonyl)furan-2-carboxylic acid with dissolved oxygen and a catalyst of a Co(II), Mn(II) or Ce(III) salt |
US9504994B2 (en) | 2014-05-08 | 2016-11-29 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
WO2017023175A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Poly( alkylene furandicarboxylate)-comprising polyester |
WO2017023174A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Polyester composition |
WO2017023173A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Masterbatch polyester composition |
WO2018017382A1 (en) * | 2016-07-22 | 2018-01-25 | Eastman Chemical Company | A furan-2,5-dicarboxylic acid purge process |
US9944615B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation and a purge zone |
US9943834B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9982094B2 (en) | 2013-10-22 | 2018-05-29 | Empire Technology Development Llc | Compounds and methods for producing nylon 6 |
US9988491B2 (en) | 2013-10-22 | 2018-06-05 | Empire Technology Development Llc | Methods and compounds for producing nylon 6,6 |
US10010812B2 (en) | 2014-05-08 | 2018-07-03 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
WO2018134263A1 (en) | 2017-01-18 | 2018-07-26 | Basf Se | 1,6,7,12-tetra-(2-isopropylphenoxy)-substituted perylene tetracarboxylic acid diimides as color converters |
WO2018172523A1 (en) | 2017-03-24 | 2018-09-27 | Basf Se | Poly(ethylene furan-2,5-dicarboxylate) as matrix material for color converters |
US10131610B2 (en) | 2013-10-25 | 2018-11-20 | Empire Technology Development Llc | Methods of producing dicarbonyl compounds |
US10208006B2 (en) | 2016-01-13 | 2019-02-19 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
WO2019038354A1 (en) | 2017-08-24 | 2019-02-28 | Basf Se | Transmitter for transmitting data and for emitting electromagnetic radiation in the visible spectral range and data transmission system |
EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
WO2019121602A1 (en) | 2017-12-19 | 2019-06-27 | Basf Se | Cyanoaryl substituted benz(othi)oxanthene compounds |
US10344011B1 (en) | 2018-05-04 | 2019-07-09 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US10421736B2 (en) | 2017-07-20 | 2019-09-24 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
WO2019179981A1 (en) | 2018-03-20 | 2019-09-26 | Basf Se | Yellow light emitting device |
WO2019238532A1 (en) | 2018-06-11 | 2019-12-19 | Basf Se | Optical data communication system comprising para-phenylenevinylenes and specific para-phenylenevinylenes |
WO2019243286A1 (en) | 2018-06-22 | 2019-12-26 | Basf Se | Photostable cyano-substituted boron-dipyrromethene dye as green emitter for display and illumination applications |
US10526301B1 (en) | 2018-10-18 | 2020-01-07 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
WO2020053124A1 (en) | 2018-09-11 | 2020-03-19 | Basf Se | Receiver comprising a luminescent collector for optical data communication |
US10696645B2 (en) | 2017-07-20 | 2020-06-30 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate |
US10865190B2 (en) | 2015-07-24 | 2020-12-15 | E I Du Pont De Nemours And Company | Processes for preparing 2,5-furandicarboxylic acid and esters thereof |
WO2021089393A1 (en) | 2019-11-05 | 2021-05-14 | Furanix Technologies B.V. | Polyester composition |
CN112898251A (en) * | 2019-11-19 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 2, 5-furandicarboxylic acid |
CN112898250A (en) * | 2019-11-19 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Preparation method of 2, 5-furandicarboxylic acid |
US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
EP2486027B2 (en) † | 2009-10-07 | 2022-01-19 | Furanix Technologies B.V. | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof |
WO2022043500A1 (en) | 2020-08-27 | 2022-03-03 | Furanix Technologies B.V. | Process for producing polyester comprising 2,5-furandicarboxylate units |
WO2022106560A1 (en) | 2020-11-20 | 2022-05-27 | Furanix Technologies B.V. | Polyester composition with improved impact properties |
WO2022136332A1 (en) | 2020-12-23 | 2022-06-30 | Furanix Technologies B.V. | Process for producing a polyester comprising 2,5-furandicarboxylate units |
WO2022245623A1 (en) * | 2021-05-20 | 2022-11-24 | Eastman Chemical Company | Purge process for 5-(alkoxycarbonyl)furan-2-carboylic acid (acfc) |
WO2022245625A1 (en) * | 2021-05-20 | 2022-11-24 | Eastman Chemical Company | Purge process for 5-(methoxycarbonyl)furan-2-carboxylic acid (mcfc) |
WO2024089105A1 (en) | 2022-10-26 | 2024-05-02 | Furanix Technologies B.V. | Polyester of improved colour stability |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102731448B (en) * | 2012-06-27 | 2014-08-13 | 北京大学 | Preparation method for furan-2,5-dicarbaldehyde |
MX2015014835A (en) * | 2013-04-25 | 2016-03-11 | Archer Daniels Midland Co | Catalytic synthesis of reduced furan derivatives. |
JP2016520043A (en) * | 2013-04-29 | 2016-07-11 | アーチャー−ダニエルズ−ミッドランド カンパニー | 5- (Hydroxymethyl) furan-2-carbaldehyde (HMF) sulfonate and process for its synthesis |
CN105324030A (en) * | 2013-06-28 | 2016-02-10 | 阿彻丹尼尔斯米德兰德公司 | Tetrahydrofuran-2,5-dicarbaldehydes (diformyl-tetrahydrofuran, DFTHF) and process for making the same |
US20160304479A1 (en) * | 2013-12-19 | 2016-10-20 | Archer Daniels Midland Company | Sulfonates of furan-2,5-dimethanol and (tetrahydrofuran-2,5-diyl)dimethanol and derivatives thereof |
JP6575126B2 (en) * | 2014-05-08 | 2019-09-18 | 三菱ケミカル株式会社 | Method for producing furfural and method for producing furan |
ES2911178T3 (en) * | 2014-08-19 | 2022-05-18 | Archer Daniels Midland Co | Catalyst and procedure for preparing 2,5-furanedicarboxylic acid from hydroxymethylfurfural in water |
TWI564074B (en) * | 2014-12-16 | 2017-01-01 | 財團法人工業技術研究院 | Oxidation catalyst for furfural compound and applying method thereof |
CN105688988B (en) | 2014-12-16 | 2018-11-27 | 财团法人工业技术研究院 | Oxidation reaction catalyst for furfural compound and oxidation method for furfural compound |
DE112016001317T5 (en) * | 2015-03-20 | 2018-01-04 | Stanford University | Carbonate-assisted carboxylation reaction for the synthesis of valuable organic compounds |
DK3283470T3 (en) | 2015-04-14 | 2023-12-11 | Du Pont | PROCESSES FOR THE MANUFACTURE OF 2,5-FURANDICARBOXYLIC ACID AND DERIVATIVES THEREOF |
KR101715169B1 (en) | 2015-05-21 | 2017-03-10 | 한국생산기술연구원 | Method for preparing 2,5-furandicarboxylic acid |
JP6615230B2 (en) | 2015-06-05 | 2019-12-04 | センヴィナ・セー・フェー | Process for producing purified acid composition |
CN108349920A (en) * | 2015-09-17 | 2018-07-31 | 微麦德斯公司 | Oxidation chemistry on furan aldehydes |
CN108541276A (en) | 2015-12-18 | 2018-09-14 | 罗地亚经营管理公司 | Based on the alcohol of furans via the selective oxidation of electrification technique |
KR101835609B1 (en) * | 2016-03-07 | 2018-03-08 | 한국생산기술연구원 | Catalyst for producing 2,5- furandicarboxlic acid and method for producing 2,5- furandicarboxlic acid using the same |
CN105732551B (en) * | 2016-04-18 | 2017-12-15 | 张玲 | A kind of method for purifying the furandicarboxylic acid of bio-based 2,5 |
CN105906587B (en) * | 2016-04-25 | 2017-12-26 | 王琪宇 | A kind of method of 2,5 furyl dimethyl carbinol purifying |
CN105753819B (en) * | 2016-04-26 | 2018-06-08 | 张玲 | A kind of method of 5 hydroxymethyl furfural purifying |
CN105884721B (en) * | 2016-04-26 | 2017-11-24 | 张玲 | A kind of method of 2,5 furans dicarbaldehyde purifying |
CN108299357A (en) * | 2017-01-12 | 2018-07-20 | 中国科学院宁波材料技术与工程研究所 | A kind of preparation method of disubstituted furan compound |
CN107011296B (en) * | 2017-04-27 | 2019-04-19 | 广西科学院 | The method for preparing 2,5- furans dicarbaldehyde using saccharide compound degradation |
KR102009467B1 (en) | 2018-01-08 | 2019-08-09 | 한국화학연구원 | Heterogeneous catalyst for producing 2,5-furandicarboxylic acid based on Chitosan support and its preparation method |
KR102005344B1 (en) | 2018-01-23 | 2019-07-30 | 한국화학연구원 | NiCo2O4 catalyst for manufacturing 2,5-furandicarboxylic acid, method for producing the same, and electrode for manufacturing 2,5-furandicarboxylic acid containing the same |
US11655334B2 (en) * | 2018-06-25 | 2023-05-23 | Eastman Chemical Company | Oxidation process to produce 5 methyl 5-methylfuran-2-carboxylate (MMFC) |
US11440895B2 (en) | 2018-06-25 | 2022-09-13 | Eastman Chemical Company | Oxidation process to produce 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) |
US10544118B2 (en) | 2018-06-25 | 2020-01-28 | Eastman Chemical Company | Oxidation process to produce 5 methyl 5-methylfuran-2-carboxylate (MMFC) |
WO2021045927A1 (en) | 2019-09-05 | 2021-03-11 | Eastman Chemical Company | Efficient process for producing 5-(alkoxycarbonyl)-furan-2-carboxylic acids |
CN110746389A (en) * | 2019-10-18 | 2020-02-04 | 承德石油高等专科学校 | Method for preparing furoic acid |
CN112830915B (en) * | 2019-11-19 | 2021-11-23 | 中国科学院宁波材料技术与工程研究所 | Low-temperature preparation method of 2, 5-furandicarboxylic acid |
CN111087371A (en) * | 2019-12-17 | 2020-05-01 | 北京理工大学 | Photocatalytic synthesis method of 2, 5-furan dicarbaldehyde |
KR102347177B1 (en) * | 2020-02-13 | 2022-01-04 | 한국화학연구원 | Preparing method for 5-alkoxymethylfurfural |
ES2924086T3 (en) | 2020-05-15 | 2022-10-04 | Archer Daniels Midland Co | Co-production of monomers, including at least one bio-based monomer |
CN113198512B (en) * | 2021-05-11 | 2022-06-24 | 莆田达凯新材料有限公司 | Nitrogen-carbon-doped cobalt-based bimetallic catalyst, preparation method thereof and preparation method of dimethyl 2, 5-furandicarboxylate |
US11708343B2 (en) | 2021-07-16 | 2023-07-25 | Kse, Inc. | Method and integrated process for the carboxylation of furan derived carboxylic acids to 2,5-furandicarboxylic acid |
CN114213369A (en) * | 2021-12-27 | 2022-03-22 | 宏业生物科技股份有限公司 | Synthesis method of furoic acid |
WO2023166503A1 (en) | 2022-03-01 | 2023-09-07 | Celluflux Ltd. | Synthesis of 5-acetoxymethyl furfural in the presence of recyclable salt catalysts |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030055271A1 (en) | 2000-03-27 | 2003-03-20 | Vladimir Grushin | Oxidation of 5-(hydroxymethyl) furfural to 2,5-diformylfuran and subsequent decarbonylation to unsubstituted furan |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2917520A (en) | 1957-09-11 | 1959-12-15 | Arthur C Cope | Production and recovery of furans |
DE3826073A1 (en) | 1988-07-30 | 1990-02-01 | Hoechst Ag | METHOD FOR THE OXIDATION OF 5-HYDROXYMETHYLFURFURAL |
DE19615878A1 (en) | 1996-04-22 | 1997-10-23 | Episucres Sa | High yield selective production of furan-2,5-di:carboxaldehyde |
US6448454B1 (en) | 2000-04-07 | 2002-09-10 | The University Of Kansas | Catalytic oxidation of organic substrates by transition metal complexes in organic solvent media expanded by supercritical or subcritical carbon dioxide |
US6706900B2 (en) | 2001-09-17 | 2004-03-16 | E. I. Du Pont De Nemours And Company | Process for preparing 2,5-diformylfuran from carbohydrates |
US7317116B2 (en) | 2004-12-10 | 2008-01-08 | Archer-Daniels-Midland-Company | Processes for the preparation and purification of hydroxymethylfuraldehyde and derivatives |
JP2007261990A (en) | 2006-03-28 | 2007-10-11 | Canon Inc | Method for producing furan-2,5-dicarboxylic acid |
WO2008054804A2 (en) * | 2006-10-31 | 2008-05-08 | Battelle Memorial Institute | Hydroxymethyl furfural oxidation methods |
JP5207677B2 (en) * | 2007-07-17 | 2013-06-12 | キヤノン株式会社 | Process for producing 2,5-furandicarboxylic acid |
EP2197866B1 (en) † | 2007-09-07 | 2013-02-27 | Furanix Technologies B.V. | Hydroxymethylfurfural ethers from sugars and higher alcohols |
EP2862858A1 (en) | 2009-05-14 | 2015-04-22 | Archer-Daniels-Midland Company | Oxidation of a 5-formyl-2-furancarboxylic acid alkyl ester or of a 5-(alkoxymethyl)- 2-furancarboxylic acid to a 2,5-furandicarboxylic acid-2-alkyl monoester |
SG179041A1 (en) | 2009-10-07 | 2012-04-27 | Furanix Technologies Bv | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof |
-
2010
- 2010-05-14 EP EP20140188869 patent/EP2862858A1/en not_active Withdrawn
- 2010-05-14 CN CN201510079540.8A patent/CN104744414B/en active Active
- 2010-05-14 EP EP17179479.5A patent/EP3257845A1/en not_active Withdrawn
- 2010-05-14 US US13/319,877 patent/US8558018B2/en active Active
- 2010-05-14 BR BRPI1007729-4A patent/BRPI1007729A2/en not_active Application Discontinuation
- 2010-05-14 ES ES16177758T patent/ES2730100T3/en active Active
- 2010-05-14 BR BR122017024876-6A patent/BR122017024876B1/en active IP Right Grant
- 2010-05-14 PL PL10775584T patent/PL2430010T3/en unknown
- 2010-05-14 EP EP16177758.6A patent/EP3133064B1/en active Active
- 2010-05-14 EP EP14172600.0A patent/EP2784069B2/en active Active
- 2010-05-14 TR TR2019/08177T patent/TR201908177T4/en unknown
- 2010-05-14 ES ES10775584.5T patent/ES2542972T3/en active Active
- 2010-05-14 CN CN201080026027.8A patent/CN102459214B/en active Active
- 2010-05-14 EP EP10775584.5A patent/EP2430010B1/en not_active Revoked
- 2010-05-14 WO PCT/US2010/034856 patent/WO2010132740A2/en active Application Filing
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030055271A1 (en) | 2000-03-27 | 2003-03-20 | Vladimir Grushin | Oxidation of 5-(hydroxymethyl) furfural to 2,5-diformylfuran and subsequent decarbonylation to unsubstituted furan |
Non-Patent Citations (3)
Title |
---|
See also references of EP2430010A4 |
W. PARTENHEMIER; V GRUSHIN, ADV. SYNTH. CATAL., vol. 343, 2001, pages 102 - 111 |
W. PARTENHEMIER; V GRUSHIN, DV, SYNTH, CALAL., vol. 343, 2001, pages 102 - 111 |
Cited By (140)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2784069B1 (en) | 2009-05-14 | 2016-07-06 | Archer-Daniels-Midland Company | Process for the oxidation of 5-(alkoxymethyl)furfural to 5-(alkoxycarbonyl)furan-2-carboxylic acid with dissolved oxygen and a catalyst of a Co(II), Mn(II) or Ce(III) salt |
WO2011043661A1 (en) * | 2009-10-07 | 2011-04-14 | 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 |
EP3666764A1 (en) * | 2009-10-07 | 2020-06-17 | 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 |
US8865921B2 (en) | 2009-10-07 | 2014-10-21 | 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 |
EP2486027B2 (en) † | 2009-10-07 | 2022-01-19 | Furanix Technologies B.V. | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof |
US9199958B2 (en) | 2011-05-24 | 2015-12-01 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US8846960B2 (en) | 2011-05-24 | 2014-09-30 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
EP2714671B1 (en) | 2011-05-24 | 2016-09-07 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161968A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
EP3686192A1 (en) * | 2011-05-24 | 2020-07-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
EP2714672B1 (en) | 2011-05-24 | 2018-12-19 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
EP2714674B1 (en) | 2011-05-24 | 2019-03-13 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
US9428480B2 (en) | 2011-05-24 | 2016-08-30 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161971A3 (en) * | 2011-05-24 | 2014-05-08 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161972A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161967A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161973A1 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161970A3 (en) * | 2011-05-24 | 2014-05-01 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
US8791278B2 (en) | 2011-05-24 | 2014-07-29 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US8791277B2 (en) | 2011-05-24 | 2014-07-29 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
US8796477B2 (en) | 2011-05-24 | 2014-08-05 | Eastman Chemical Company | Oxidation process to produce a crude and/or purified carboxylic acid product |
WO2012161970A2 (en) * | 2011-05-24 | 2012-11-29 | Eastman Chemical Company | An oxidation process to produce a crude and/or purified carboxylic acid product |
US10350584B2 (en) | 2011-05-24 | 2019-07-16 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
EP2751060A2 (en) * | 2011-08-31 | 2014-07-09 | The University Of Kansas | Process for producing both biobased succinic acid and 2,5-furandicarboxylic acid |
EP2751060A4 (en) * | 2011-08-31 | 2015-04-08 | Univ Kansas | Process for producing both biobased succinic acid and 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 |
US9527954B2 (en) | 2011-10-24 | 2016-12-27 | Furanix Technologies B.V. | Process for preparing a polymer product having a 2,5-furandicarboxylate moiety within the polymer backbone to be used in bottle, film or fibre applications |
WO2013062408A1 (en) | 2011-10-24 | 2013-05-02 | Furanix Technologies B.V. | A process for preparing a polymer product having a 2,5-furandicarboxylate moiety within the polymer backbone to be used in bottle, film or fibre applications |
US10030097B2 (en) | 2011-10-24 | 2018-07-24 | Furanix Technologies B.V. | Polyester-containing object made from melt-processing poly(ethylene-2,5-furandicarboxylate) |
EP3327061A1 (en) | 2011-10-24 | 2018-05-30 | Synvina C.V. | Polymer product having a 2,5-furandicarboxylate moiety within the polymer backbone to be used in bottle, film or fibre applications |
US9365531B2 (en) | 2011-12-22 | 2016-06-14 | Roquette Freres | Method for selectively oxidizing 5-hydroxymethyl furaldehyde |
CN104011036A (en) * | 2011-12-22 | 2014-08-27 | 罗盖特公司 | Improved method for selectively oxidizing 5-hydroxymethyl furaldehyde |
WO2013093322A1 (en) * | 2011-12-22 | 2013-06-27 | Roquette Freres | Improved method for selectively oxidizing 5-hydroxymethyl furaldehyde |
FR2984889A1 (en) * | 2011-12-22 | 2013-06-28 | Roquette Freres | IMPROVED METHOD OF SELECTIVE OXIDATION OF 5-HYDROMETHYL FURALDEHYDE |
JP2015502972A (en) * | 2011-12-22 | 2015-01-29 | ロケット・フルーレ | Improved method for selectively oxidizing 5-hydroxymethylfuraldehyde |
US9029581B2 (en) | 2012-06-22 | 2015-05-12 | Eastman Chemical Company | Esterification of furan-2,5-dicarboxylic acid to a dialkyl-furan-2,5-dicarboxylate vapor with rectification |
US8912349B2 (en) | 2012-06-22 | 2014-12-16 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate separation and solid liquid separation |
EP2864306B1 (en) | 2012-06-22 | 2018-01-10 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
US8658810B2 (en) | 2012-06-22 | 2014-02-25 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate vapor |
US9169229B2 (en) | 2012-06-22 | 2015-10-27 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate by physical separation and solid liquid separation |
US8859788B2 (en) | 2012-06-22 | 2014-10-14 | Eastman Chemical Company | Esterification of furan-2,5-dicarboxylic acid to a dialkyl-furan-2,5-dicarboxylate vapor with rectification |
US8748479B2 (en) | 2012-06-22 | 2014-06-10 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
US9458122B2 (en) | 2012-06-22 | 2016-10-04 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
EP2864307B1 (en) | 2012-06-22 | 2018-03-07 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
US9156806B2 (en) | 2012-06-22 | 2015-10-13 | Eastman Chemical Company | Process for purifying crude furan 2,5-dicarboxylic acid using hydrogenation |
US8969404B2 (en) | 2012-06-22 | 2015-03-03 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
US9249118B2 (en) | 2012-06-22 | 2016-02-02 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation |
US9266850B2 (en) | 2012-07-20 | 2016-02-23 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US8809556B2 (en) | 2012-07-20 | 2014-08-19 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US10011579B2 (en) | 2012-07-20 | 2018-07-03 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
EP3578552A1 (en) * | 2012-07-20 | 2019-12-11 | Eastman Chemical Company | An oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US9029580B2 (en) | 2012-07-20 | 2015-05-12 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US10882032B2 (en) | 2012-07-20 | 2021-01-05 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9676740B2 (en) | 2012-07-20 | 2017-06-13 | Eastman Chemical Company | Oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
WO2014014979A1 (en) * | 2012-07-20 | 2014-01-23 | Eastman Chemical Company | An oxidation process to produce a purified carboxylic acid product via solvent displacement and post oxidation |
US8772513B2 (en) | 2012-08-30 | 2014-07-08 | Eastman Chemical Company | Oxidation process to produce a crude dry carboxylic acid product |
WO2014035813A1 (en) * | 2012-08-30 | 2014-03-06 | Eastman Chemical Company | An oxidation process to produce a crude dry carboxylic acid product |
US9206149B2 (en) | 2012-08-30 | 2015-12-08 | Eastman Chemical Company | Oxidation process to produce a crude dry carboxylic acid product |
US8916719B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
US9156805B2 (en) | 2012-11-20 | 2015-10-13 | Eastman Chemical Company | Oxidative purification method for producing purified dry furan-2,5-dicarboxylic acid |
US8916720B2 (en) | 2012-11-20 | 2014-12-23 | Eastman Chemical Company | Process for producing dry purified furan-2,5-dicarboxylic acid with oxidation off-gas treatment |
WO2014102413A1 (en) * | 2012-12-26 | 2014-07-03 | Consejo Superior De Investigaciones Científicas (Csic) | Method for producing organic molecules used as novel surfactant agents |
WO2014140398A1 (en) * | 2013-03-12 | 2014-09-18 | Consejo Superior De Investigaciones Científias (Csic) | Preparation of organic molecules which can be used as surfactants |
JP2016513641A (en) * | 2013-03-14 | 2016-05-16 | アーチャー−ダニエルズ−ミッドランド カンパニー | Method for producing 2,5-furandicarboxylic acid |
NL2010572C2 (en) * | 2013-04-05 | 2014-10-07 | Furanix Technologies Bv | Process for the preaparation of 2,5-furan-dicarboxylic acid. |
US9643945B2 (en) | 2013-04-05 | 2017-05-09 | Furanix Technologies B.V. | Process for the preparation of 2,5-furan-dicarboxylic acid |
WO2014163500A1 (en) | 2013-04-05 | 2014-10-09 | Furanix Technologies B.V. | Process for the preparation of 2,5-furan-dicarboxylic acid |
US10351973B2 (en) | 2013-06-20 | 2019-07-16 | Furanix Technologies B.V. | Process for the preparation of a fiber, a fiber and a yarn made from such a fiber |
WO2014204313A1 (en) | 2013-06-20 | 2014-12-24 | Furanix Technologies B.V. | Process for the preparation of a fiber, a fiber and a yarn made from such a fiber |
WO2015056270A1 (en) | 2013-10-17 | 2015-04-23 | Natco Pharma Limited | Process for the preparation of 2,5-furandicarboxylic acid |
US9988491B2 (en) | 2013-10-22 | 2018-06-05 | Empire Technology Development Llc | Methods and compounds for producing nylon 6,6 |
US9982094B2 (en) | 2013-10-22 | 2018-05-29 | Empire Technology Development Llc | Compounds and methods for producing nylon 6 |
US10131610B2 (en) | 2013-10-25 | 2018-11-20 | Empire Technology Development Llc | Methods of producing dicarbonyl compounds |
US9890242B2 (en) | 2014-03-11 | 2018-02-13 | Synvina C.V. | Polyester and method for preparing such a polyester |
WO2015137806A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Process for enhancing the molecular weight of a polyester |
WO2015137805A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Polyester and method for preparing such a polyester |
US9908968B2 (en) | 2014-03-11 | 2018-03-06 | Synvina C.V. | Polyester and method for preparing such a polyester |
US9840582B2 (en) | 2014-03-11 | 2017-12-12 | Furanix Technologies B.V. | Method for preparing a polyester under specific esterification conditions |
WO2015137804A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Method for preparing a polyester under specific esterification conditions |
WO2015137807A1 (en) | 2014-03-11 | 2015-09-17 | Furanix Technologies B.V. | Polyester and method for preparing such a polyester |
US10072119B2 (en) | 2014-03-11 | 2018-09-11 | Synvina C.V. | Process for enhancing the molecular weight of a polyester |
WO2015155784A1 (en) | 2014-04-09 | 2015-10-15 | Natco Pharma Limited | Process for the preparation of 2,5-furandicarboxylic acid and its ester derivative |
US10010812B2 (en) | 2014-05-08 | 2018-07-03 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US10406454B2 (en) | 2014-05-08 | 2019-09-10 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US10611743B2 (en) | 2014-05-08 | 2020-04-07 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation and a purge zone |
US11027219B2 (en) | 2014-05-08 | 2021-06-08 | Eastman Chemical Company | Furan-2, 5-dicarboxylic acid purge process |
US9573120B2 (en) | 2014-05-08 | 2017-02-21 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9604202B2 (en) | 2014-05-08 | 2017-03-28 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9944615B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation and a purge zone |
US11027263B2 (en) | 2014-05-08 | 2021-06-08 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US10695755B2 (en) | 2014-05-08 | 2020-06-30 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9943834B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9504994B2 (en) | 2014-05-08 | 2016-11-29 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
US9321744B1 (en) | 2015-06-26 | 2016-04-26 | Industrial Technology Research Institute | Method for preparing 2,5-furan dicarboxylic acid |
US10865190B2 (en) | 2015-07-24 | 2020-12-15 | E I Du Pont De Nemours And Company | Processes for preparing 2,5-furandicarboxylic acid and esters thereof |
WO2017023174A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Polyester composition |
WO2017023175A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Poly( alkylene furandicarboxylate)-comprising polyester |
WO2017023173A1 (en) | 2015-08-04 | 2017-02-09 | Furanix Technologies B.V. | Masterbatch polyester composition |
US10442780B2 (en) | 2016-01-13 | 2019-10-15 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
US11613523B2 (en) | 2016-01-13 | 2023-03-28 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
US11891370B2 (en) | 2016-01-13 | 2024-02-06 | Stora Enso Ojy | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
US10208006B2 (en) | 2016-01-13 | 2019-02-19 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
US10851074B2 (en) | 2016-01-13 | 2020-12-01 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
US10654819B2 (en) | 2016-01-13 | 2020-05-19 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
WO2018017382A1 (en) * | 2016-07-22 | 2018-01-25 | Eastman Chemical Company | A furan-2,5-dicarboxylic acid purge process |
US11279829B2 (en) | 2017-01-18 | 2022-03-22 | Basf Se | 1,6,7,12-tetra-(2-isopropylphenoxy)-substituted perylene tetracarboxylic acid diimides as color converters |
WO2018134263A1 (en) | 2017-01-18 | 2018-07-26 | Basf Se | 1,6,7,12-tetra-(2-isopropylphenoxy)-substituted perylene tetracarboxylic acid diimides as color converters |
WO2018172523A1 (en) | 2017-03-24 | 2018-09-27 | Basf Se | Poly(ethylene furan-2,5-dicarboxylate) as matrix material for color converters |
US11192872B2 (en) | 2017-07-12 | 2021-12-07 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
US10421736B2 (en) | 2017-07-20 | 2019-09-24 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
US10696645B2 (en) | 2017-07-20 | 2020-06-30 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate |
US11655227B2 (en) | 2017-07-20 | 2023-05-23 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
US10954207B2 (en) | 2017-07-20 | 2021-03-23 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
US10723712B2 (en) | 2017-07-20 | 2020-07-28 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
US11603360B2 (en) | 2017-07-20 | 2023-03-14 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate |
US11496223B2 (en) | 2017-08-24 | 2022-11-08 | Basf Se | Transmitter for transmitting data and for emitting electromagnetic radiation in the visible spectral range and data transmission system |
WO2019038354A1 (en) | 2017-08-24 | 2019-02-28 | Basf Se | Transmitter for transmitting data and for emitting electromagnetic radiation in the visible spectral range and data transmission system |
EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
WO2019121602A1 (en) | 2017-12-19 | 2019-06-27 | Basf Se | Cyanoaryl substituted benz(othi)oxanthene compounds |
US11236101B2 (en) | 2017-12-19 | 2022-02-01 | Basf Se | Cyanoaryl substituted benz(othi)oxanthene compounds |
WO2019179981A1 (en) | 2018-03-20 | 2019-09-26 | Basf Se | Yellow light emitting device |
US11898075B2 (en) | 2018-03-20 | 2024-02-13 | Basf Se | Yellow light emitting device |
US10344011B1 (en) | 2018-05-04 | 2019-07-09 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
WO2019238532A1 (en) | 2018-06-11 | 2019-12-19 | Basf Se | Optical data communication system comprising para-phenylenevinylenes and specific para-phenylenevinylenes |
WO2019243286A1 (en) | 2018-06-22 | 2019-12-26 | Basf Se | Photostable cyano-substituted boron-dipyrromethene dye as green emitter for display and illumination applications |
US12018192B2 (en) | 2018-09-11 | 2024-06-25 | Basf Se | Receiver comprising a luminescent collector for optical data communication |
WO2020053124A1 (en) | 2018-09-11 | 2020-03-19 | Basf Se | Receiver comprising a luminescent collector for optical data communication |
US11066376B2 (en) | 2018-10-18 | 2021-07-20 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
US10526301B1 (en) | 2018-10-18 | 2020-01-07 | Eastman Chemical Company | Production of purified dialkyl-furan-2,5-dicarboxylate (DAFD) in a retrofitted DMT plant |
WO2021089393A1 (en) | 2019-11-05 | 2021-05-14 | Furanix Technologies B.V. | Polyester composition |
CN112898251A (en) * | 2019-11-19 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Method for preparing 2, 5-furandicarboxylic acid |
CN112898250B (en) * | 2019-11-19 | 2023-01-13 | 宁波华呋新材料科技有限公司 | Preparation method of 2, 5-furandicarboxylic acid |
CN112898250A (en) * | 2019-11-19 | 2021-06-04 | 中国科学院宁波材料技术与工程研究所 | Preparation method of 2, 5-furandicarboxylic acid |
WO2022043501A1 (en) | 2020-08-27 | 2022-03-03 | Furanix Technologies B.V. | Preparing polyester comprising 2,5-furandicarboxylate units with germanium catalyst |
WO2022043500A1 (en) | 2020-08-27 | 2022-03-03 | Furanix Technologies B.V. | Process for producing polyester comprising 2,5-furandicarboxylate units |
WO2022106560A1 (en) | 2020-11-20 | 2022-05-27 | Furanix Technologies B.V. | Polyester composition with improved impact properties |
WO2022136332A1 (en) | 2020-12-23 | 2022-06-30 | Furanix Technologies B.V. | Process for producing a polyester comprising 2,5-furandicarboxylate units |
WO2022245625A1 (en) * | 2021-05-20 | 2022-11-24 | Eastman Chemical Company | Purge process for 5-(methoxycarbonyl)furan-2-carboxylic acid (mcfc) |
WO2022245623A1 (en) * | 2021-05-20 | 2022-11-24 | Eastman Chemical Company | Purge process for 5-(alkoxycarbonyl)furan-2-carboylic acid (acfc) |
WO2024089105A1 (en) | 2022-10-26 | 2024-05-02 | Furanix Technologies B.V. | Polyester of improved colour stability |
Also Published As
Publication number | Publication date |
---|---|
ES2542972T3 (en) | 2015-08-13 |
CN102459214A (en) | 2012-05-16 |
EP2430010A4 (en) | 2012-10-03 |
EP2430010A2 (en) | 2012-03-21 |
EP2862858A1 (en) | 2015-04-22 |
BRPI1007729A2 (en) | 2015-09-01 |
US20120059178A1 (en) | 2012-03-08 |
EP2784069A1 (en) | 2014-10-01 |
EP3133064B1 (en) | 2019-03-20 |
PL2430010T3 (en) | 2015-10-30 |
TR201908177T4 (en) | 2019-06-21 |
EP2784069B2 (en) | 2019-05-01 |
WO2010132740A3 (en) | 2011-03-31 |
CN104744414B (en) | 2017-04-12 |
EP2430010B1 (en) | 2015-04-29 |
BR122017024876B1 (en) | 2020-11-10 |
CN104744414A (en) | 2015-07-01 |
CN102459214B (en) | 2015-01-21 |
ES2730100T3 (en) | 2019-11-08 |
US8558018B2 (en) | 2013-10-15 |
EP3133064A1 (en) | 2017-02-22 |
EP2784069B1 (en) | 2016-07-06 |
EP3257845A1 (en) | 2017-12-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8558018B2 (en) | Oxidation of furfural compounds | |
EP2246340B1 (en) | Preparation of 2,5-furandialdehyde from 2,5-(hydroxymethyl)furanaldehyde in the presence of 2,2,6,6-tetramethyl-i-piperidinyloxyl | |
US8785667B2 (en) | Processes for preparing diacids, dialdehydes and polymers | |
KR101769455B1 (en) | Method for the preparation of 2,5-furandicarboxylic acid and for the preparation of the dialkyl ester of 2,5-furandicarboxylic acid | |
CA2773640C (en) | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof | |
CN109574962B (en) | Method for preparing 2, 5-furandicarboxylic acid from sugar | |
US9562028B2 (en) | Process for making 2,5-furandicarboxylic acid | |
CN114262312A (en) | Process for producing 2, 5-furandicarboxylic acid and derivatives thereof and polymers made therefrom | |
JP2011506478A (en) | Conversion of carbohydrates to hydroxymethylfurfural (HMF) and derivatives | |
WO2017076947A1 (en) | Process for preparing furan-2,5-dicarboxylic acid | |
CN111194311A (en) | Process for the preparation of furan-2, 5-dicarboxylic acid | |
CN117964583A (en) | Preparation method of Engliclazide chiral intermediate | |
JP3610483B2 (en) | 5-Formyl-3-hydroxymethylcyclohexane-1-carboxylic acid compounds and methods for producing them | |
SU249388A1 (en) | METHOD OF OBTAINING BROMOMETIMEANTHE ZN-p-HININDINES | |
CN117946039A (en) | Chiral synthesis process of englitz intermediate | |
CN117164497A (en) | Synthesis method of pyrrole-2-ketone compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201080026027.8 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10775584 Country of ref document: EP Kind code of ref document: A2 |
|
REEP | Request for entry into the european phase |
Ref document number: 2010775584 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010775584 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13319877 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
REG | Reference to national code |
Ref country code: BR Ref legal event code: B01A Ref document number: PI1007729 Country of ref document: BR |
|
ENP | Entry into the national phase |
Ref document number: PI1007729 Country of ref document: BR Kind code of ref document: A2 Effective date: 20111111 |