BR112020020667B1 - Processo para sintetizar ácido tetra-hidrofurano-2,5-dicarboxílico (thfdca) - Google Patents
Processo para sintetizar ácido tetra-hidrofurano-2,5-dicarboxílico (thfdca) Download PDFInfo
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- BR112020020667B1 BR112020020667B1 BR112020020667-9A BR112020020667A BR112020020667B1 BR 112020020667 B1 BR112020020667 B1 BR 112020020667B1 BR 112020020667 A BR112020020667 A BR 112020020667A BR 112020020667 B1 BR112020020667 B1 BR 112020020667B1
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- Prior art keywords
- acid
- thfdca
- catalyst
- hto
- dihydroxyadipic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 54
- CWZQRDJXBMLSTF-UHFFFAOYSA-N oxolane-2,5-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)O1 CWZQRDJXBMLSTF-UHFFFAOYSA-N 0.000 title claims description 19
- 230000002194 synthesizing effect Effects 0.000 title abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 85
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 30
- 230000001590 oxidative effect Effects 0.000 claims abstract description 24
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 13
- AMXRXGOSEWMPEF-UHFFFAOYSA-N hexane-1,2,5,6-tetrol Chemical compound OCC(O)CCC(O)CO AMXRXGOSEWMPEF-UHFFFAOYSA-N 0.000 claims abstract description 12
- TVYABKWHFSGGMF-UHFFFAOYSA-N [2-(hydroxymethyl)oxolan-3-yl]methanol Chemical compound OCC1CCOC1CO TVYABKWHFSGGMF-UHFFFAOYSA-N 0.000 claims description 40
- SHCCNDIEMUQSCR-UHFFFAOYSA-N 2,5-dihydroxyhexanedioic acid Chemical compound OC(=O)C(O)CCC(O)C(O)=O SHCCNDIEMUQSCR-UHFFFAOYSA-N 0.000 claims description 30
- HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 23
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 10
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 6
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 19
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- 230000037361 pathway Effects 0.000 description 11
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- 238000006555 catalytic reaction Methods 0.000 description 9
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 230000008901 benefit Effects 0.000 description 8
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
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- 229940117916 cinnamic aldehyde Drugs 0.000 description 4
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- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
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- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- VBUYCZFBVCCYFD-YVZJFKFKSA-N 2-dehydro-L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-YVZJFKFKSA-N 0.000 description 1
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- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- YULHQOUNQSJZHT-UHFFFAOYSA-N oxolane-2,3-dicarboxylic acid Chemical compound OC(=O)C1CCOC1C(O)=O YULHQOUNQSJZHT-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical class [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
-
- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/644—Arsenic, antimony or bismuth
- B01J23/6447—Bismuth
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- 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862657277P | 2018-04-13 | 2018-04-13 | |
| US62/657,277 | 2018-04-13 | ||
| PCT/US2019/024493 WO2019199468A1 (en) | 2018-04-13 | 2019-03-28 | Conversion of 1,2,5,6-hexanetetrol (hto) to tetrahydrofuran dicarboxylic acid (thfdca) |
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| BR112020020667A2 BR112020020667A2 (pt) | 2021-01-12 |
| BR112020020667B1 true BR112020020667B1 (pt) | 2022-05-17 |
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| CN (1) | CN111971274B (https=) |
| BR (1) | BR112020020667B1 (https=) |
| ES (1) | ES2924952T3 (https=) |
| WO (1) | WO2019199468A1 (https=) |
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| CN113121477A (zh) * | 2021-06-02 | 2021-07-16 | 宁波国生科技有限公司 | 一种2,5-四氢呋喃二甲酸的制备方法 |
| CN116063258B (zh) * | 2021-10-29 | 2025-03-11 | 中国石油化工股份有限公司 | 一种连续生产5-羟甲基糠醛和2,5-呋喃二甲酸的方法 |
| EP4680600A1 (en) * | 2023-03-16 | 2026-01-21 | Specialty Operations France | Method for producing tetrahydrofuran-2-carboxylic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR3001970B1 (fr) | 2013-02-11 | 2015-02-27 | Centre Nat Rech Scient | Procede de preparation d'acide 2,5-furane dicarboxylique |
| MX2016000106A (es) | 2013-06-28 | 2016-03-01 | Archer Daniels Midland Co | Tetrahidrofuran-2,5-dicarbaldehidos (diformiltetrahidrofurano, dfthf) y procesos para su sintesis. |
| RU2016141809A (ru) | 2014-04-10 | 2018-05-10 | Арчер Дэниелс Мидлэнд Компани | Синтез R-глюкозидов сахароспиртов, восстановленных сахароспиртов и фурановых производных восстановленных сахароспиртов |
| US9593064B2 (en) * | 2014-05-01 | 2017-03-14 | Wisconsin Alumni Research Foundation | Conversion of alcohols to alkyl esters and carboxylic acids using heterogeneous palladium-based catalysts |
| ES2830174T3 (es) * | 2015-03-05 | 2021-06-03 | Bp Corp North America Inc | Síntesis de furanos a partir de azúcares a través de intermediarios ceto |
| WO2017061858A1 (en) | 2015-10-05 | 2017-04-13 | Avantium Knowledge Centre B.V. | Process for the manufacture of an adipic acid product |
| FR3053336B1 (fr) * | 2016-07-01 | 2018-09-21 | Centre National De La Recherche Scientifique | Procede de preparation de l'acide 2,5-furane dicarboxylique (fdca) a partir de derives de pentoses |
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2019
- 2019-03-28 KR KR1020207032605A patent/KR102448643B1/ko active Active
- 2019-03-28 BR BR112020020667-9A patent/BR112020020667B1/pt active IP Right Grant
- 2019-03-28 US US17/046,663 patent/US12024496B2/en active Active
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- 2019-03-28 EP EP19784331.1A patent/EP3774753B1/en active Active
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- 2019-03-28 WO PCT/US2019/024493 patent/WO2019199468A1/en not_active Ceased
- 2019-03-28 CN CN201980025526.6A patent/CN111971274B/zh active Active
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| KR20200135540A (ko) | 2020-12-02 |
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| KR102448643B1 (ko) | 2022-09-28 |
| EP3774753B1 (en) | 2022-07-27 |
| EP3774753A1 (en) | 2021-02-17 |
| BR112020020667A2 (pt) | 2021-01-12 |
| WO2019199468A1 (en) | 2019-10-17 |
| CN111971274B (zh) | 2023-04-11 |
| JP2021521117A (ja) | 2021-08-26 |
| JP7071534B2 (ja) | 2022-05-19 |
| EP3774753A4 (en) | 2021-05-19 |
| CN111971274A (zh) | 2020-11-20 |
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