JP2015536641A5 - - Google Patents
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- JP2015536641A5 JP2015536641A5 JP2015533235A JP2015533235A JP2015536641A5 JP 2015536641 A5 JP2015536641 A5 JP 2015536641A5 JP 2015533235 A JP2015533235 A JP 2015533235A JP 2015533235 A JP2015533235 A JP 2015533235A JP 2015536641 A5 JP2015536641 A5 JP 2015536641A5
- Authority
- JP
- Japan
- Prior art keywords
- ddg
- fdca
- derivative
- conversion
- acid
- 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.)
- Granted
Links
- 238000006243 chemical reaction Methods 0.000 claims description 88
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical class OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 150000007522 mineralic acids Chemical class 0.000 claims description 17
- 230000002194 synthesizing effect Effects 0.000 claims description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- IZSRJDGCGRAUAR-MROZADKFSA-M 5-dehydro-D-gluconate Chemical compound OCC(=O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IZSRJDGCGRAUAR-MROZADKFSA-M 0.000 description 25
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 22
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 20
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 18
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 18
- 235000012208 gluconic acid Nutrition 0.000 description 18
- 239000000174 gluconic acid Substances 0.000 description 18
- 230000002255 enzymatic effect Effects 0.000 description 17
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 description 16
- AEMOLEFTQBMNLQ-BZINKQHNSA-N D-Guluronic Acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-BZINKQHNSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 12
- 239000008103 glucose Substances 0.000 description 10
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 10
- AEMOLEFTQBMNLQ-CLQWQSTFSA-N l-iduronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@@H]1O AEMOLEFTQBMNLQ-CLQWQSTFSA-N 0.000 description 10
- KDOGLQUELUMIFG-UHFFFAOYSA-N 2,5-dioxohexanoic acid Chemical compound CC(=O)CCC(=O)C(O)=O KDOGLQUELUMIFG-UHFFFAOYSA-N 0.000 description 7
- XGGAWFDOIDZRPI-UHFFFAOYSA-N 4,6-Dihydroxy Natural products C1=C2OCOC2=CC(C2OC(C3C(OC(O)C32)C=2C=C3OCOC3=CC=2)O)=C1 XGGAWFDOIDZRPI-UHFFFAOYSA-N 0.000 description 7
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 4
- 230000037361 pathway Effects 0.000 description 4
- QUURPCHWPQNNGL-ZAFYKAAXSA-N 5-dehydro-4-deoxy-D-glucaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)CC(=O)C(O)=O QUURPCHWPQNNGL-ZAFYKAAXSA-N 0.000 description 3
- WTAHRPBPWHCMHW-PAKKCRSFSA-N 3-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)C(=O)[C@@H](O)C(O)=O WTAHRPBPWHCMHW-PAKKCRSFSA-N 0.000 description 2
- DSLZVSRJTYRBFB-LLEIAEIESA-L D-glucarate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O DSLZVSRJTYRBFB-LLEIAEIESA-L 0.000 description 2
- -1 guluronic acid lactone Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009483 enzymatic pathway Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261704408P | 2012-09-21 | 2012-09-21 | |
| US61/704,408 | 2012-09-21 | ||
| PCT/US2013/061036 WO2014047510A1 (en) | 2012-09-21 | 2013-09-20 | Compositions and methods for producing chemicals and derivatives thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017091072A Division JP2017195885A (ja) | 2012-09-21 | 2017-05-01 | 化学物質およびその誘導体を生成するための組成物および方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015536641A JP2015536641A (ja) | 2015-12-24 |
| JP2015536641A5 true JP2015536641A5 (https=) | 2016-10-27 |
| JP6163557B2 JP6163557B2 (ja) | 2017-07-12 |
Family
ID=50341985
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015533235A Expired - Fee Related JP6163557B2 (ja) | 2012-09-21 | 2013-09-20 | 化学物質およびその誘導体を生成するための組成物および方法 |
| JP2017091072A Pending JP2017195885A (ja) | 2012-09-21 | 2017-05-01 | 化学物質およびその誘導体を生成するための組成物および方法 |
| JP2018055638A Withdrawn JP2018139587A (ja) | 2012-09-21 | 2018-03-23 | 化学物質およびその誘導体を生成するための組成物および方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017091072A Pending JP2017195885A (ja) | 2012-09-21 | 2017-05-01 | 化学物質およびその誘導体を生成するための組成物および方法 |
| JP2018055638A Withdrawn JP2018139587A (ja) | 2012-09-21 | 2018-03-23 | 化学物質およびその誘導体を生成するための組成物および方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9506090B2 (https=) |
| EP (1) | EP2898083A4 (https=) |
| JP (3) | JP6163557B2 (https=) |
| CN (1) | CN104769122B (https=) |
| AU (1) | AU2013317782B2 (https=) |
| BR (1) | BR112015006255A2 (https=) |
| CA (1) | CA2885662A1 (https=) |
| SG (2) | SG10201702263QA (https=) |
| WO (1) | WO2014047510A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106414753A (zh) * | 2014-03-21 | 2017-02-15 | 合成基因组股份有限公司 | 用于生产化学品及其衍生物的组合物和方法 |
| WO2016057676A1 (en) * | 2014-10-09 | 2016-04-14 | Bp Corporation North America Inc. | Use of carboxylic acids in the production of 2,5-furandicarboxylic acid |
| CA2962614A1 (en) * | 2014-10-09 | 2016-04-14 | Bp Corporation North America Inc. | Use of reactants in the production of 2,5-furandicarboxylic acid |
| CA2962605A1 (en) * | 2014-10-09 | 2016-04-14 | Bp Corporation North America Inc. | Use of an acidic solvent and water in the production of 2,5-furandicarboxylic acid |
| CA2961585A1 (en) * | 2014-10-09 | 2016-04-14 | Bp Corporation North America Inc. | Use of bromine ions in the production of 2,5-furandicarboxylic acid |
| WO2016057687A1 (en) * | 2014-10-09 | 2016-04-14 | Bp Corporation North America Inc. | Use of halogens in the production of 2,5-furandicarboxylic acid |
| 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 |
| US10087161B2 (en) | 2015-08-20 | 2018-10-02 | Synthetic Genomics, Inc. | Synthesis of FDCA and FDCA precursors from gluconic acid derivatives |
| EP3402787A4 (en) | 2016-01-13 | 2019-11-27 | Stora Enso Oyj | PROCESS FOR THE PREPARATION OF 2,5-FURANDIC ACETIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF |
| US10927363B2 (en) | 2016-04-04 | 2021-02-23 | Mie University | DNA sequence and expression vector for alginate lyase |
| EP3458578A1 (en) * | 2016-05-20 | 2019-03-27 | Teknologian Tutkimuskeskus VTT OY | Improved meso-galactaric acid production from galacturonic acid with genetically modified fungal cells |
| CN107417651A (zh) * | 2017-06-20 | 2017-12-01 | 合肥利夫生物科技有限公司 | 一种制备2,5‑呋喃二甲酸及其衍生物的方法 |
| EP4071142B1 (en) | 2017-06-22 | 2023-10-04 | Archer Daniels Midland Company | Process for making esters of 2,5-furandicarboxylic acid |
| EP3652161A1 (en) | 2017-07-12 | 2020-05-20 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| EP3460067A1 (en) * | 2017-09-20 | 2019-03-27 | Technische Universität München | Process for enzymatic oxidation of linear carbohydrates |
| CN107954959A (zh) * | 2017-11-22 | 2018-04-24 | 南京工业大学 | 一种制备2,5-呋喃二甲酸及其前体物质的方法 |
| US20230272364A1 (en) * | 2019-07-11 | 2023-08-31 | Bp Corporation North America Inc. | Gluconate dehydratase enzymes and recombinant cells |
| CN115397977A (zh) * | 2020-03-06 | 2022-11-25 | 索鲁根公司 | 用于生产葡萄糖氧化产物的组合物和方法 |
| JP2023517621A (ja) * | 2020-03-12 | 2023-04-26 | ソリュゲン インコーポレーテッド | ２，５－フランジカルボン酸の製造のための組成物及び方法 |
| JP2024513175A (ja) * | 2021-03-26 | 2024-03-22 | アーチャー－ダニエルズ－ミッドランド カンパニー | 酒石酸塩による阻害に耐性のある熱安定性ｄ－グルカル酸デヒドラターゼ |
| US12295919B2 (en) | 2022-03-16 | 2025-05-13 | Mie University | Methods of treatment and prevention using 4-deoxy-L-erythro-5-hexoseulose uronic acid |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184479A (en) * | 1965-05-18 | Process for the preparation of | ||
| CH387656A (de) | 1961-03-07 | 1965-02-15 | Ciba Geigy | Verfahren zur Herstellung von 2,5-Furandicarbonsäure |
| US3203963A (en) | 1963-04-18 | 1965-08-31 | Atlas Chem Ind | Method of purifying dehydromucic acid |
| US3326944A (en) | 1964-03-09 | 1967-06-20 | Atlas Chem Ind | Method of producing dehydromucic acid |
| JP2850515B2 (ja) * | 1990-09-25 | 1999-01-27 | 東洋紡績株式会社 | グルコースデヒドロゲナーゼおよびその製造法 |
| FR2723946B1 (fr) * | 1994-08-24 | 1996-10-18 | Ard Sa | Procede de fabrication d'un diester de l'acide 2,5-furane dicarboxylique |
| JP4804187B2 (ja) | 2006-03-28 | 2011-11-02 | キヤノン株式会社 | フラン−２，５−ジカルボン酸の製造方法 |
| JP5051509B2 (ja) * | 2006-11-16 | 2012-10-17 | 独立行政法人産業技術総合研究所 | ２，５−フランジカルボン酸ジエステルの製造方法 |
| AU2008249370B2 (en) * | 2007-05-08 | 2013-09-05 | Ensuiko Sugar Refining Co., Ltd. | Method for producing glucuronic acid by glucuronic acid fermentation |
| US7385081B1 (en) | 2007-11-14 | 2008-06-10 | Bp Corporation North America Inc. | Terephthalic acid composition and process for the production thereof |
| CN102066551B (zh) | 2008-03-27 | 2013-10-09 | 基因组股份公司 | 用于产生己二酸和其他化合物的微生物 |
| US8835147B2 (en) | 2008-04-04 | 2014-09-16 | Massachusetts Institute Of Technology | Cellular production of glucaric acid through recombinant expression of uronate dehydrogenase and myo-inositol oxygenase |
| FI20086236A0 (fi) | 2008-12-23 | 2008-12-23 | Valtion Teknillinen | Heksuronihapon konversio heksarihapoksi |
| KR101769455B1 (ko) | 2009-10-07 | 2017-08-18 | 퓨라닉스 테크놀러지스 비.브이. | 2,5-퓨란다이카르복시산 및 2,5-퓨란다이카르복시산의 다이알킬 에스테르의 제조방법 |
| JP5550303B2 (ja) | 2009-10-19 | 2014-07-16 | キヤノン株式会社 | ２，５−フランジカルボン酸の製造方法 |
| WO2011081658A2 (en) * | 2009-12-15 | 2011-07-07 | Qteros, Inc. | Methods and compositions for producing chemical products from c. phytofermentants |
| NL2006359C2 (en) | 2011-03-08 | 2012-04-24 | Bird Engineering B V | Genetically modified cell and process for use of said cell. |
| EP2503003A1 (en) | 2011-03-24 | 2012-09-26 | Volker Sieber | Synthetic pathway for the production of alcohols or amines |
| US8953008B2 (en) * | 2011-09-20 | 2015-02-10 | U-Nica Technology Ag | Method and device for producing color images on substrates containing color bodies and products produced thereby |
| WO2013049711A1 (en) | 2011-09-29 | 2013-04-04 | Bio Architecture Lab, Inc. | Methods for preparing 2,5-furandicarboxylic acid |
| US9079844B2 (en) | 2012-04-04 | 2015-07-14 | Stichting Dienst Landbouwkundig Onderzoek | Catalytic oxidation of uronic acids to aldaric acids |
| CN105026548B (zh) | 2012-06-04 | 2019-06-18 | 盐水港精糖株式会社 | D-葡萄糖二酸生产菌及d-葡萄糖二酸的制造方法 |
| WO2014015256A2 (en) | 2012-07-20 | 2014-01-23 | Novozymes A/S | Enzymatic oxidation of 5-hydroxymethylfurfural and derivatives thereof |
-
2013
- 2013-09-20 BR BR112015006255A patent/BR112015006255A2/pt not_active Application Discontinuation
- 2013-09-20 AU AU2013317782A patent/AU2013317782B2/en not_active Ceased
- 2013-09-20 US US14/033,300 patent/US9506090B2/en not_active Expired - Fee Related
- 2013-09-20 WO PCT/US2013/061036 patent/WO2014047510A1/en not_active Ceased
- 2013-09-20 SG SG10201702263QA patent/SG10201702263QA/en unknown
- 2013-09-20 EP EP13838235.3A patent/EP2898083A4/en not_active Withdrawn
- 2013-09-20 JP JP2015533235A patent/JP6163557B2/ja not_active Expired - Fee Related
- 2013-09-20 CA CA2885662A patent/CA2885662A1/en not_active Abandoned
- 2013-09-20 CN CN201380056638.0A patent/CN104769122B/zh not_active Expired - Fee Related
- 2013-09-20 SG SG11201502143VA patent/SG11201502143VA/en unknown
-
2017
- 2017-05-01 JP JP2017091072A patent/JP2017195885A/ja active Pending
-
2018
- 2018-03-23 JP JP2018055638A patent/JP2018139587A/ja not_active Withdrawn
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