JP2008515769A5 - - Google Patents
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- Publication number
- JP2008515769A5 JP2008515769A5 JP2007519537A JP2007519537A JP2008515769A5 JP 2008515769 A5 JP2008515769 A5 JP 2008515769A5 JP 2007519537 A JP2007519537 A JP 2007519537A JP 2007519537 A JP2007519537 A JP 2007519537A JP 2008515769 A5 JP2008515769 A5 JP 2008515769A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- aldaric
- solvent mixture
- aldarolactone
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 claims 19
- 238000000034 method Methods 0.000 claims 11
- 239000011877 solvent mixture Substances 0.000 claims 6
- 150000002596 lactones Chemical class 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 2
- QXKAIJAYHKCRRA-UHFFFAOYSA-N D-lyxonic acid Natural products OCC(O)C(O)C(O)C(O)=O QXKAIJAYHKCRRA-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- 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 claims 1
- OIYFAQRHWMVENL-UHFFFAOYSA-N 2-(4-oxopyran-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC1=O OIYFAQRHWMVENL-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- RGHNJXZEOKUKBD-AIHAYLRMSA-N D-altronic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-AIHAYLRMSA-N 0.000 claims 1
- QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 claims 1
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 claims 1
- 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 claims 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims 1
- QXKAIJAYHKCRRA-UZBSEBFBSA-N D-lyxonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-UZBSEBFBSA-N 0.000 claims 1
- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 claims 1
- QXKAIJAYHKCRRA-FLRLBIABSA-N D-xylonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-FLRLBIABSA-N 0.000 claims 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 claims 1
- RGHNJXZEOKUKBD-SKNVOMKLSA-N L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SKNVOMKLSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 229910052792 caesium Inorganic materials 0.000 claims 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 229940095625 calcium glucarate Drugs 0.000 claims 1
- UGZVNIRNPPEDHM-SBBOJQDXSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical group [Ca+2].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O UGZVNIRNPPEDHM-SBBOJQDXSA-L 0.000 claims 1
- 239000003729 cation exchange resin Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 claims 1
- 239000000174 gluconic acid Substances 0.000 claims 1
- 235000012208 gluconic acid Nutrition 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58483504P | 2004-06-30 | 2004-06-30 | |
| US58483204P | 2004-06-30 | 2004-06-30 | |
| PCT/US2005/023816 WO2006005071A1 (en) | 2004-06-30 | 2005-06-30 | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using azeotrophic distillation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008515769A JP2008515769A (ja) | 2008-05-15 |
| JP2008515769A5 true JP2008515769A5 (cg-RX-API-DMAC7.html) | 2008-06-26 |
Family
ID=35058776
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519536A Pending JP2008505122A (ja) | 2004-06-30 | 2005-06-30 | ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
| JP2007519537A Pending JP2008515769A (ja) | 2004-06-30 | 2005-06-30 | 共沸蒸留を用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007519536A Pending JP2008505122A (ja) | 2004-06-30 | 2005-06-30 | ガススパージングを用いた、アルドノラクトン、アルダロラクトン、およびアルダロジラクトンの合成 |
Country Status (4)
| Country | Link |
|---|---|
| EP (2) | EP1773838A1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2008505122A (cg-RX-API-DMAC7.html) |
| CA (2) | CA2571060A1 (cg-RX-API-DMAC7.html) |
| WO (2) | WO2006005071A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2571060A1 (en) * | 2004-06-30 | 2006-01-12 | E.I. Du Pont De Nemours And Company | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using azeotrophic distillation |
| NZ596975A (en) | 2009-06-13 | 2014-04-30 | Rennovia Inc | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8785683B2 (en) | 2009-06-13 | 2014-07-22 | Rennovia, Inc. | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1830618A (en) * | 1930-04-12 | 1931-11-03 | Pfizer Charles & Co | Production of lactones |
| GB613444A (en) * | 1946-01-17 | 1948-11-29 | John George Mackay Bremner | Improvements in and relating to the production of heterocyclic compounds |
| US4581465A (en) * | 1984-03-16 | 1986-04-08 | The Dow Chemical Company | Preparation of 1,4-lactones of 3,6-anhydrohexanoic acids |
| FI92051C (fi) * | 1992-03-17 | 1994-09-26 | Amylum Nv | Menetelmä ksylitolin valmistamiseksi D-glukoosista ja D-glukoosin ja D-fruktoosin sekä D-glukoosin ja D-galaktoosin seoksista |
| US5312967A (en) * | 1992-08-12 | 1994-05-17 | Uab Research Foundation | Process for making activated aldarate esters, ester/lactones and lactones |
| US6049004A (en) * | 1998-12-11 | 2000-04-11 | Kiely; Donald E. | Nitric acid removal from oxidation products |
| JP2004501117A (ja) * | 2000-05-26 | 2004-01-15 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ガスパージ支援によるアンヒドロ糖アルコールの製造方法 |
| KR100407758B1 (ko) * | 2001-08-27 | 2003-12-01 | 씨제이 주식회사 | 스타틴의 제조에 있어서 락톤화 방법 |
| CA2571060A1 (en) * | 2004-06-30 | 2006-01-12 | E.I. Du Pont De Nemours And Company | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using azeotrophic distillation |
| KR20070058464A (ko) * | 2004-07-28 | 2007-06-08 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 캡슐식 주형 조립체와 교환 가능한 카트리지 |
-
2005
- 2005-06-30 CA CA002571060A patent/CA2571060A1/en not_active Abandoned
- 2005-06-30 WO PCT/US2005/023816 patent/WO2006005071A1/en not_active Ceased
- 2005-06-30 EP EP05769130A patent/EP1773838A1/en not_active Withdrawn
- 2005-06-30 EP EP05787937A patent/EP1773839A1/en not_active Withdrawn
- 2005-06-30 JP JP2007519536A patent/JP2008505122A/ja active Pending
- 2005-06-30 CA CA002571774A patent/CA2571774A1/en not_active Abandoned
- 2005-06-30 JP JP2007519537A patent/JP2008515769A/ja active Pending
- 2005-06-30 WO PCT/US2005/023815 patent/WO2006005070A1/en not_active Ceased
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