JP2008515769A - 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 - Google Patents
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 Download PDFInfo
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- JP2008515769A JP2008515769A JP2007519537A JP2007519537A JP2008515769A JP 2008515769 A JP2008515769 A JP 2008515769A JP 2007519537 A JP2007519537 A JP 2007519537A JP 2007519537 A JP2007519537 A JP 2007519537A JP 2008515769 A JP2008515769 A JP 2008515769A
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- Prior art keywords
- acid
- aldaric
- lactone
- mixture
- aldonic
- 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.)
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- 238000010533 azeotropic distillation Methods 0.000 title claims abstract description 9
- 230000015572 biosynthetic process Effects 0.000 title claims description 8
- 238000003786 synthesis reaction Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 164
- 238000000034 method Methods 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000002596 lactones Chemical class 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 150000007513 acids Chemical class 0.000 claims description 29
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 19
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 19
- 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 description 17
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 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 description 15
- 238000009835 boiling Methods 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 239000011877 solvent mixture Substances 0.000 claims description 12
- 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 description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- QXKAIJAYHKCRRA-UHFFFAOYSA-N D-lyxonic acid Natural products OCC(O)C(O)C(O)C(O)=O QXKAIJAYHKCRRA-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 235000012208 gluconic acid Nutrition 0.000 claims description 9
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 8
- -1 sulfonate ester Chemical class 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 7
- 239000000174 gluconic acid Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 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 description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 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 description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 3
- OIYFAQRHWMVENL-UHFFFAOYSA-N 2-(4-oxopyran-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC1=O OIYFAQRHWMVENL-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 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
- 238000001816 cooling Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 6
- 230000018044 dehydration Effects 0.000 abstract description 4
- 238000006297 dehydration reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- QRFNDAVXJCGLFB-GJPGBQJBSA-N (3r,3ar,6s,6ar)-3,6-dihydroxy-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione Chemical compound O1C(=O)[C@H](O)[C@H]2OC(=O)[C@@H](O)[C@H]21 QRFNDAVXJCGLFB-GJPGBQJBSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 229950006191 gluconic acid Drugs 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 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 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- SXZYCXMUPBBULW-TXICZTDVSA-N D-glucono-1,4-lactone Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-TXICZTDVSA-N 0.000 description 4
- 235000014633 carbohydrates Nutrition 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RGHNJXZEOKUKBD-QMKXCQHVSA-N (2r,3r,4s,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-QMKXCQHVSA-N 0.000 description 3
- SXZYCXMUPBBULW-UHFFFAOYSA-N 1,4-gluconolactone Natural products OCC(O)C1OC(=O)C(O)C1O SXZYCXMUPBBULW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- ZQWFSIZRQANUDA-WQMSYZFBSA-L calcium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate;tetrahydrate Chemical compound O.O.O.O.[Ca+2].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O ZQWFSIZRQANUDA-WQMSYZFBSA-L 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BSPZKKBWTBYQOH-LAMMAJBHSA-N (2s,3r,4s)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound O[C@@H]1[C@H](O)C(=O)O[C@@H]1C(O)=O BSPZKKBWTBYQOH-LAMMAJBHSA-N 0.000 description 2
- SXZYCXMUPBBULW-KLVWXMOXSA-N (3r,4s,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-KLVWXMOXSA-N 0.000 description 2
- SXZYCXMUPBBULW-SQOUGZDYSA-N (3s,4r,5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-SQOUGZDYSA-N 0.000 description 2
- CUOKHACJLGPRHD-HZLVTQRSSA-N (3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one Chemical compound OC[C@@H]1OC(=O)[C@@H](O)[C@H]1O CUOKHACJLGPRHD-HZLVTQRSSA-N 0.000 description 2
- SXZYCXMUPBBULW-MBMOQRBOSA-N (3s,4r,5s)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-MBMOQRBOSA-N 0.000 description 2
- SXZYCXMUPBBULW-MGCNEYSASA-N (3s,4s,5r)-5-[(1r)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@@H](O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-MGCNEYSASA-N 0.000 description 2
- SXZYCXMUPBBULW-FCAWWPLPSA-N (3s,4s,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-FCAWWPLPSA-N 0.000 description 2
- SXZYCXMUPBBULW-GHWWWWGESA-N (5r)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one Chemical compound OCC(O)[C@H]1OC(=O)C(O)C1O SXZYCXMUPBBULW-GHWWWWGESA-N 0.000 description 2
- BSPZKKBWTBYQOH-UHFFFAOYSA-N 3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound OC1C(O)C(=O)OC1C(O)=O BSPZKKBWTBYQOH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- SXZYCXMUPBBULW-LECHCGJUSA-N D-(-)-Gulono-gamma-lactone Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-LECHCGJUSA-N 0.000 description 2
- DSLZVSRJTYRBFB-YCAKELIYSA-N D-altraric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-YCAKELIYSA-N 0.000 description 2
- CUOKHACJLGPRHD-JJYYJPOSSA-N D-arabinono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@@H](O)[C@@H]1O CUOKHACJLGPRHD-JJYYJPOSSA-N 0.000 description 2
- SXZYCXMUPBBULW-AIHAYLRMSA-N D-galactono-1,4-lactone Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-AIHAYLRMSA-N 0.000 description 2
- RGHNJXZEOKUKBD-KKQCNMDGSA-N D-gulonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-KKQCNMDGSA-N 0.000 description 2
- CUOKHACJLGPRHD-UZBSEBFBSA-N D-lyxono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@@H](O)[C@H]1O CUOKHACJLGPRHD-UZBSEBFBSA-N 0.000 description 2
- CUOKHACJLGPRHD-BXXZVTAOSA-N D-ribono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H]1O CUOKHACJLGPRHD-BXXZVTAOSA-N 0.000 description 2
- CUOKHACJLGPRHD-FLRLBIABSA-N D-xylono-1,4-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@H]1O CUOKHACJLGPRHD-FLRLBIABSA-N 0.000 description 2
- 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 2
- DSLZVSRJTYRBFB-GJPGBQJBSA-N L-altraric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-GJPGBQJBSA-N 0.000 description 2
- QXKAIJAYHKCRRA-YVZJFKFKSA-N L-arabinonic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-YVZJFKFKSA-N 0.000 description 2
- CUOKHACJLGPRHD-YVZJFKFKSA-N L-arabinono-1,4-lactone Chemical compound OC[C@@H]1OC(=O)[C@H](O)[C@H]1O CUOKHACJLGPRHD-YVZJFKFKSA-N 0.000 description 2
- SXZYCXMUPBBULW-NEEWWZBLSA-N L-galactono-1,4-lactone Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-NEEWWZBLSA-N 0.000 description 2
- DSLZVSRJTYRBFB-AJSXGEPRSA-N L-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-AJSXGEPRSA-N 0.000 description 2
- DSLZVSRJTYRBFB-ORZLYADOSA-N L-idaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-ORZLYADOSA-N 0.000 description 2
- QXKAIJAYHKCRRA-NUNKFHFFSA-N L-xylonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-NUNKFHFFSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 0 O[C@@]([C@](*C(C1)=O)[C@@]1O)C(O)=O Chemical compound O[C@@]([C@](*C(C1)=O)[C@@]1O)C(O)=O 0.000 description 2
- 150000001299 aldehydes Chemical group 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 235000012209 glucono delta-lactone Nutrition 0.000 description 2
- 229960003681 gluconolactone Drugs 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000007273 lactonization reaction Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XECPAIJNBXCOBO-ZNIBRBMXSA-N (2R)-2-[(2R,3R,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound O=C([C@H](O)[C@H]1[C@H](O)[C@@H](O)C(=O)O1)O XECPAIJNBXCOBO-ZNIBRBMXSA-N 0.000 description 1
- XECPAIJNBXCOBO-KXMYSMCESA-N (2R)-2-[(2S,3S,4R)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound C1([C@H](O)[C@H](O)[C@@H]([C@@H](O)C(=O)O)O1)=O XECPAIJNBXCOBO-KXMYSMCESA-N 0.000 description 1
- BSPZKKBWTBYQOH-ADNNCPOWSA-N (2R,3R,4R)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound C1([C@H](O)[C@@H](O)[C@H](C(=O)O)O1)=O BSPZKKBWTBYQOH-ADNNCPOWSA-N 0.000 description 1
- XECPAIJNBXCOBO-CMPLKCRRSA-N (2S)-2-[(2R,3R,4S)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound O=C([C@@H](O)[C@H]1[C@H](O)[C@H](O)C(=O)O1)O XECPAIJNBXCOBO-CMPLKCRRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-NRXMZTRTSA-N (2r,3r,4r,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NRXMZTRTSA-N 0.000 description 1
- KSJDOQFYNPUQDU-JJKGCWMISA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic acid;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O KSJDOQFYNPUQDU-JJKGCWMISA-N 0.000 description 1
- RGHNJXZEOKUKBD-NEEWWZBLSA-N (2r,3s,4s,5s)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-NEEWWZBLSA-N 0.000 description 1
- NPTTZSYLTYJCPR-MZJVJLTCSA-N (2r,4s)-2,3,4-trihydroxypentanedioic acid Chemical compound OC(=O)[C@@H](O)C(O)[C@@H](O)C(O)=O NPTTZSYLTYJCPR-MZJVJLTCSA-N 0.000 description 1
- RGHNJXZEOKUKBD-LECHCGJUSA-N (2s,3r,4s,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-LECHCGJUSA-N 0.000 description 1
- BSPZKKBWTBYQOH-ZPAAKOCQSA-N (2s,3s,4s)-3,4-dihydroxy-5-oxooxolane-2-carboxylic acid Chemical compound O[C@H]1[C@H](O)C(=O)O[C@@H]1C(O)=O BSPZKKBWTBYQOH-ZPAAKOCQSA-N 0.000 description 1
- RGHNJXZEOKUKBD-STGXQOJASA-N (2s,3s,4s,5r)-2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-STGXQOJASA-N 0.000 description 1
- SXZYCXMUPBBULW-RSJOWCBRSA-N (3r,4r,5s)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@@H]1OC(=O)[C@H](O)[C@H]1O SXZYCXMUPBBULW-RSJOWCBRSA-N 0.000 description 1
- SXZYCXMUPBBULW-QMKXCQHVSA-N (3r,4s,5r)-5-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-one Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-QMKXCQHVSA-N 0.000 description 1
- CUOKHACJLGPRHD-PZGQECOJSA-N (3r,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one Chemical compound OC[C@@H]1OC(=O)[C@H](O)[C@@H]1O CUOKHACJLGPRHD-PZGQECOJSA-N 0.000 description 1
- CQWFJIVHGWJYKB-UHNVWZDZSA-N (3s,4r)-3,4-dihydro-2h-pyran-3,4-diol Chemical compound O[C@H]1COC=C[C@H]1O CQWFJIVHGWJYKB-UHNVWZDZSA-N 0.000 description 1
- SXZYCXMUPBBULW-VRUJNKQUSA-N (3s,4s,5r)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one Chemical compound OCC(O)[C@H]1OC(=O)[C@@H](O)[C@@H]1O SXZYCXMUPBBULW-VRUJNKQUSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NPTTZSYLTYJCPR-UHFFFAOYSA-N 2,3,4-trihydroxypentanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)C(O)=O NPTTZSYLTYJCPR-UHFFFAOYSA-N 0.000 description 1
- BUBVLQDEIIUIQG-UHFFFAOYSA-N 3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one Chemical compound C=1C=CC=CC=1COC1C(OCC=2C=CC=CC=2)C(OCC=2C=CC=CC=2)C(=O)OC1COCC1=CC=CC=C1 BUBVLQDEIIUIQG-UHFFFAOYSA-N 0.000 description 1
- QXKAIJAYHKCRRA-BXXZVTAOSA-N D-ribonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-BXXZVTAOSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- RGHNJXZEOKUKBD-RSJOWCBRSA-N L-galactonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-RSJOWCBRSA-N 0.000 description 1
- RGHNJXZEOKUKBD-KLVWXMOXSA-N L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-KLVWXMOXSA-N 0.000 description 1
- SXZYCXMUPBBULW-SKNVOMKLSA-N L-gulono-1,4-lactone Chemical compound OC[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O SXZYCXMUPBBULW-SKNVOMKLSA-N 0.000 description 1
- QXKAIJAYHKCRRA-PZGQECOJSA-N L-lyxonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)C(O)=O QXKAIJAYHKCRRA-PZGQECOJSA-N 0.000 description 1
- CUOKHACJLGPRHD-NUNKFHFFSA-N L-xylono-1,4-lactone Chemical compound OC[C@@H]1OC(=O)[C@@H](O)[C@@H]1O CUOKHACJLGPRHD-NUNKFHFFSA-N 0.000 description 1
- PCDUPQLMRPKEJS-URVZRBSTSA-N OC(C1)[C@H](C(O)=O)OC1=O Chemical compound OC(C1)[C@H](C(O)=O)OC1=O PCDUPQLMRPKEJS-URVZRBSTSA-N 0.000 description 1
- QRFNDAVXJCGLFB-CMSHZVMTSA-N O[C@@H](C(C([C@@H]1O)O2)OC1=O)C2=O Chemical compound O[C@@H](C(C([C@@H]1O)O2)OC1=O)C2=O QRFNDAVXJCGLFB-CMSHZVMTSA-N 0.000 description 1
- PJXZKSXXRQMJKR-MFQBSIDQSA-N O[C@@H](C([C@@H](C1)O)OC1=O)C(O)=O Chemical compound O[C@@H](C([C@@H](C1)O)OC1=O)C(O)=O PJXZKSXXRQMJKR-MFQBSIDQSA-N 0.000 description 1
- BSPZKKBWTBYQOH-GJBJXMDJSA-N O[C@@H]([C@H](C(O)=O)OC1=O)[C@@H]1O Chemical compound O[C@@H]([C@H](C(O)=O)OC1=O)[C@@H]1O BSPZKKBWTBYQOH-GJBJXMDJSA-N 0.000 description 1
- QRFNDAVXJCGLFB-YCQGKDFPSA-N O[C@@H]([C@H](C([C@@H]1O)O2)OC1=O)C2=O Chemical compound O[C@@H]([C@H](C([C@@H]1O)O2)OC1=O)C2=O QRFNDAVXJCGLFB-YCQGKDFPSA-N 0.000 description 1
- SJXPYYVWFUOQSD-YQWWZGPCSA-N O[C@@H]([C@H](C([C@H]1C=O)O2)OC1=O)C2=O Chemical compound O[C@@H]([C@H](C([C@H]1C=O)O2)OC1=O)C2=O SJXPYYVWFUOQSD-YQWWZGPCSA-N 0.000 description 1
- XECPAIJNBXCOBO-QTHOGDSYSA-N O[C@H]([C@@H](C([C@@H]1O)O)OC1=O)C(O)=O Chemical compound O[C@H]([C@@H](C([C@@H]1O)O)OC1=O)C(O)=O XECPAIJNBXCOBO-QTHOGDSYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical group OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- CUOKHACJLGPRHD-UHFFFAOYSA-N gamma-Lacton der l-Arabonsaeure Natural products OCC1OC(=O)C(O)C1O CUOKHACJLGPRHD-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005406 washing Methods 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Furan Compounds (AREA)
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 true JP2008515769A (ja) | 2008-05-15 |
| JP2008515769A5 JP2008515769A5 (enExample) | 2008-06-26 |
Family
ID=35058776
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
Family Applications After (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) | EP1773839A1 (enExample) |
| JP (2) | JP2008515769A (enExample) |
| CA (2) | CA2571060A1 (enExample) |
| WO (2) | WO2006005071A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008505122A (ja) * | 2004-06-30 | 2008-02-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 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 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102803194B (zh) | 2009-06-13 | 2016-01-20 | 莱诺维亚公司 | 由含碳水化合物的物质生产戊二酸和衍生物 |
| BRPI1010708B1 (pt) | 2009-06-13 | 2018-04-03 | Rennovia, Inc. | "processos para preparar um produto de ácido adípico, e ácido adípico ou derivado do mesmo" |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1830618A (en) * | 1930-04-12 | 1931-11-03 | Pfizer Charles & Co | Production of lactones |
| JP2008508122A (ja) * | 2004-07-28 | 2008-03-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 封入金型アセンブリおよび交換可能カートリッジ |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2001264807A1 (en) * | 2000-05-26 | 2001-12-11 | E.I. Du Pont De Nemours And Company | Process for the manufacture of anhydro sugar alcohols with the assistance of a gas purge |
| KR100407758B1 (ko) * | 2001-08-27 | 2003-12-01 | 씨제이 주식회사 | 스타틴의 제조에 있어서 락톤화 방법 |
| WO2006005071A1 (en) * | 2004-06-30 | 2006-01-12 | E.I. Dupont De Nemours And Company | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using azeotrophic distillation |
-
2005
- 2005-06-30 WO PCT/US2005/023816 patent/WO2006005071A1/en not_active Ceased
- 2005-06-30 CA CA002571060A patent/CA2571060A1/en not_active Abandoned
- 2005-06-30 EP EP05787937A patent/EP1773839A1/en not_active Withdrawn
- 2005-06-30 JP JP2007519537A patent/JP2008515769A/ja active Pending
- 2005-06-30 WO PCT/US2005/023815 patent/WO2006005070A1/en not_active Ceased
- 2005-06-30 JP JP2007519536A patent/JP2008505122A/ja active Pending
- 2005-06-30 CA CA002571774A patent/CA2571774A1/en not_active Abandoned
- 2005-06-30 EP EP05769130A patent/EP1773838A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1830618A (en) * | 1930-04-12 | 1931-11-03 | Pfizer Charles & Co | Production of lactones |
| JP2008508122A (ja) * | 2004-07-28 | 2008-03-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 封入金型アセンブリおよび交換可能カートリッジ |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008505122A (ja) * | 2004-06-30 | 2008-02-21 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1773838A1 (en) | 2007-04-18 |
| CA2571774A1 (en) | 2006-01-12 |
| EP1773839A1 (en) | 2007-04-18 |
| JP2008505122A (ja) | 2008-02-21 |
| WO2006005071A1 (en) | 2006-01-12 |
| CA2571060A1 (en) | 2006-01-12 |
| WO2006005070A1 (en) | 2006-01-12 |
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