ES2642005T3 - Esterificación del ácido 2,5-furandicarboxílico - Google Patents
Esterificación del ácido 2,5-furandicarboxílico Download PDFInfo
- Publication number
- ES2642005T3 ES2642005T3 ES13866244.0T ES13866244T ES2642005T3 ES 2642005 T3 ES2642005 T3 ES 2642005T3 ES 13866244 T ES13866244 T ES 13866244T ES 2642005 T3 ES2642005 T3 ES 2642005T3
- Authority
- ES
- Spain
- Prior art keywords
- alcohol
- reaction
- fdca
- psi
- mixture
- 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.)
- Active
Links
- 238000005886 esterification reaction Methods 0.000 title claims description 43
- 230000032050 esterification Effects 0.000 title description 28
- 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 description 16
- DNXDYHALMANNEJ-UHFFFAOYSA-N furan-2,3-dicarboxylic acid Chemical class OC(=O)C=1C=COC=1C(O)=O DNXDYHALMANNEJ-UHFFFAOYSA-N 0.000 claims description 92
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 62
- 150000002148 esters Chemical class 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 25
- 241000894007 species Species 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 150000005690 diesters Chemical class 0.000 claims description 14
- 239000003377 acid catalyst Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 239000012298 atmosphere Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 238000012545 processing Methods 0.000 claims description 5
- 239000004367 Lipase Substances 0.000 claims description 4
- 102000004882 Lipase Human genes 0.000 claims description 4
- 108090001060 Lipase Proteins 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 235000019421 lipase Nutrition 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- SEUNICDWQTXURO-UHFFFAOYSA-N 2-methoxycarbonylfuran-3-carboxylic acid Chemical compound COC(=O)C=1OC=CC=1C(O)=O SEUNICDWQTXURO-UHFFFAOYSA-N 0.000 claims description 3
- 238000006911 enzymatic reaction Methods 0.000 claims description 3
- LVHVLAXPAFDNQF-UHFFFAOYSA-N 2-ethoxycarbonylfuran-3-carboxylic acid Chemical compound CCOC(=O)C=1OC=CC=1C(O)=O LVHVLAXPAFDNQF-UHFFFAOYSA-N 0.000 claims description 2
- OOXPHDJPHYPNNE-UHFFFAOYSA-N 2-propoxycarbonylfuran-3-carboxylic acid Chemical compound CCCOC(=O)C=1OC=CC=1C(O)=O OOXPHDJPHYPNNE-UHFFFAOYSA-N 0.000 claims description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000001569 carbon dioxide Substances 0.000 description 45
- 229910002092 carbon dioxide Inorganic materials 0.000 description 45
- 239000000047 product Substances 0.000 description 23
- 230000008569 process Effects 0.000 description 22
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
- -1 isononyl Chemical group 0.000 description 18
- 230000001476 alcoholic effect Effects 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- 239000007789 gas Substances 0.000 description 14
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 239000004576 sand Substances 0.000 description 8
- 239000002028 Biomass Substances 0.000 description 7
- 235000011089 carbon dioxide Nutrition 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 150000008163 sugars Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001263 acyl chlorides Chemical class 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- FXJUUMGKLWHCNZ-UHFFFAOYSA-N dimethyl furan-2,3-dicarboxylate Chemical compound COC(=O)C=1C=COC=1C(=O)OC FXJUUMGKLWHCNZ-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- 150000002402 hexoses Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011560 quantum fluid Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- SCTRJLCZKJRGCR-UHFFFAOYSA-N 2-(7-methyloctoxycarbonyl)furan-3-carboxylic acid Chemical compound CC(C)CCCCCCOC(=O)C1=C(C=CO1)C(=O)O SCTRJLCZKJRGCR-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 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 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910021386 carbon form Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LKHUWNGGFCYROX-UHFFFAOYSA-N diethyl furan-2,3-dicarboxylate Chemical compound CCOC(=O)C=1C=COC=1C(=O)OCC LKHUWNGGFCYROX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- PDSULNVJASBMLP-UHFFFAOYSA-N furan-2,5-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)O1 PDSULNVJASBMLP-UHFFFAOYSA-N 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261739761P | 2012-12-20 | 2012-12-20 | |
| US201261739761P | 2012-12-20 | ||
| PCT/US2013/073821 WO2014099438A2 (en) | 2012-12-20 | 2013-12-09 | Esterification of 2,5-furan-dicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2642005T3 true ES2642005T3 (es) | 2017-11-14 |
Family
ID=50979377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13866244.0T Active ES2642005T3 (es) | 2012-12-20 | 2013-12-09 | Esterificación del ácido 2,5-furandicarboxílico |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9765045B2 (https=) |
| EP (1) | EP2935229B1 (https=) |
| JP (1) | JP6370307B2 (https=) |
| KR (1) | KR101963478B1 (https=) |
| CN (1) | CN105246958B (https=) |
| AU (1) | AU2013363501B2 (https=) |
| BR (1) | BR112015014183B1 (https=) |
| CA (1) | CA2895186C (https=) |
| ES (1) | ES2642005T3 (https=) |
| MX (1) | MX362292B (https=) |
| SG (1) | SG11201503646TA (https=) |
| WO (1) | WO2014099438A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102038177B1 (ko) * | 2012-10-29 | 2019-10-29 | 아처 다니엘 미드랜드 캄파니 | 탄산염을 이용한 카복실산의 알코올 매개 에스테르화 |
| MX374703B (es) * | 2013-08-30 | 2025-03-06 | Furanix Technologies Bv | Proceso para purificar una composicion acida que comprende acido 2-formil-furan-5-carboxilico y acido 2,5-furandicarboxilico. |
| US9944615B2 (en) | 2014-05-08 | 2018-04-17 | Eastman Chemical Company | Purifying crude furan 2,5-dicarboxylic acid by hydrogenation and a purge zone |
| US9504994B2 (en) | 2014-05-08 | 2016-11-29 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
| US10010812B2 (en) | 2014-05-08 | 2018-07-03 | Eastman Chemical Company | Furan-2,5-dicarboxylic acid purge process |
| JP6452428B2 (ja) * | 2014-12-18 | 2019-01-16 | 花王株式会社 | ハロゲン系樹脂用可塑剤 |
| US10160740B2 (en) | 2015-03-20 | 2018-12-25 | The Board Of Trustees Of The Leland Stanford Junior University | Carbonate-promoted carboxylation reactions for the synthesis of valuable organic compounds |
| CN107848995B (zh) | 2015-04-14 | 2021-12-28 | 杜邦公司 | 用于生产2,5-呋喃二甲酸及其衍生物以及由其制成的聚合物的方法 |
| WO2017019431A1 (en) * | 2015-07-24 | 2017-02-02 | E I Du Pont De Nemours And Company | Process for producing 2,5-furandicarboxylic acid dialkyl ester |
| WO2017019441A1 (en) * | 2015-07-24 | 2017-02-02 | E I Du Pont De Nemours And Company | Processes for preparing 2,5-furandicarboxylic acid and esters thereof |
| WO2017091437A1 (en) * | 2015-11-24 | 2017-06-01 | Archer Daniels Midland Company | Organotin catalysts in esterification processes of furan-2,5-dicarboxylic acid (fdca) |
| JP7458147B2 (ja) | 2016-01-13 | 2024-03-29 | ストラ エンソ オーユーイー | ２，５－フランジカルボン酸ならびにその中間体および誘導体の製造方法 |
| WO2018187031A1 (en) * | 2017-04-05 | 2018-10-11 | Archer Daniels Midland Company | Novel esterification catalyst and uses thereof |
| BR112019027341A2 (pt) | 2017-06-22 | 2020-07-07 | Archer Daniels Midland Company | processo para produzir ésteres de fdca e processo para produzir ésteres de fdca a partir de dextrose |
| CA3069521A1 (en) | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| US20190023838A1 (en) | 2017-07-20 | 2019-01-24 | Eastman Chemical Company | Production of polyethylene furanoate in a retrofitted pet plant |
| WO2019214576A1 (zh) * | 2018-05-10 | 2019-11-14 | 中国科学院长春应用化学研究所 | 2，5-呋喃二甲酸的制备方法 |
| US20190389820A1 (en) * | 2018-06-25 | 2019-12-26 | Eastman Chemical Company | Process for producing 5-(alkoxycarbonyl)furan-2-carboxylic acids and compositions containing same |
| US11440895B2 (en) | 2018-06-25 | 2022-09-13 | Eastman Chemical Company | Oxidation process to produce 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC) |
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| CN112585123A (zh) * | 2018-08-31 | 2021-03-30 | 伊士曼化工公司 | 在改造的dmt设备中生产纯化呋喃-2,5-二甲酸二烷基酯（dafd） |
| 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 |
| WO2021045927A1 (en) * | 2019-09-05 | 2021-03-11 | Eastman Chemical Company | Efficient process for producing 5-(alkoxycarbonyl)-furan-2-carboxylic acids |
| US20230348410A1 (en) * | 2020-08-12 | 2023-11-02 | Archer Daniels Midland Company | Purification of 2,5-furandicarboxylic acid, dimethyl ester and other esterified products |
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| US5071754A (en) * | 1990-01-23 | 1991-12-10 | Battelle Memorial Institute | Production of esters of lactic acid, esters of acrylic acid, lactic acid, and acrylic acid |
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| DE102004008042A1 (de) * | 2004-02-19 | 2005-09-01 | Goldschmidt Gmbh | Verfahren zur Herstellung von Aminosäureestern und deren Säure-Additions-Salzen |
| DE102004047869A1 (de) * | 2004-10-01 | 2006-04-06 | Goldschmidt Gmbh | Verfahren zur enzymatischen Synthese von Pyroglutaminsäureestern |
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| CA2625511A1 (en) * | 2008-03-13 | 2009-09-13 | Dilum Dunuwila | Process for the direct production of esters of carboxylic acids from fermentation broths |
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| WO2010090965A2 (en) * | 2009-02-03 | 2010-08-12 | David Miller | Method of producing biodiesel with supercritical alcohol and apparatus for same |
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| US8519167B2 (en) * | 2009-10-07 | 2013-08-27 | Furanix Technologies B.V. | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof |
| JP5866290B2 (ja) * | 2009-10-07 | 2016-02-17 | フラニックス テクノロジーズ ベスローテン フェンノートシャップ | ２，５−フランジカルボン酸を調製する方法及び２，５−フランジカルボン酸のジアルキルエステルを調製する方法 |
| EP2481733A1 (en) * | 2011-01-28 | 2012-08-01 | Süd-Chemie AG | Process for manufacturing esters of 2,5-furandicarboxylic acid |
| US8658810B2 (en) * | 2012-06-22 | 2014-02-25 | Eastman Chemical Company | Method for producing purified dialkyl-furan-2,5-dicarboxylate vapor |
| 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 |
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| JP2016506407A (ja) | 2016-03-03 |
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| BR112015014183A2 (pt) | 2017-07-11 |
| CA2895186A1 (en) | 2014-06-26 |
| CN105246958A (zh) | 2016-01-13 |
| BR112015014183B1 (pt) | 2021-03-16 |
| US20150315166A1 (en) | 2015-11-05 |
| KR20150095931A (ko) | 2015-08-21 |
| EP2935229B1 (en) | 2017-06-28 |
| JP6370307B2 (ja) | 2018-08-08 |
| CN105246958B (zh) | 2018-02-02 |
| SG11201503646TA (en) | 2015-07-30 |
| KR101963478B1 (ko) | 2019-03-28 |
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