JP2004501117A - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP2004501117A JP2004501117A JP2002500879A JP2002500879A JP2004501117A JP 2004501117 A JP2004501117 A JP 2004501117A JP 2002500879 A JP2002500879 A JP 2002500879A JP 2002500879 A JP2002500879 A JP 2002500879A JP 2004501117 A JP2004501117 A JP 2004501117A
- Authority
- JP
- Japan
- Prior art keywords
- zeolite
- dehydration catalyst
- reaction
- inert gas
- water
- 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.)
- Abandoned
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000010926 purge Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 25
- 230000018044 dehydration Effects 0.000 claims abstract description 23
- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 19
- 230000008569 process Effects 0.000 claims abstract description 13
- 239000011261 inert gas Substances 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 23
- 239000010457 zeolite Substances 0.000 claims description 19
- 229910021536 Zeolite Inorganic materials 0.000 claims description 16
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 16
- 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 15
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical group O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 15
- 239000000600 sorbitol Substances 0.000 claims description 14
- 229960002479 isosorbide Drugs 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229910044991 metal oxide Inorganic materials 0.000 claims description 6
- 150000004706 metal oxides Chemical class 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical group O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 3
- 229910001410 inorganic ion Inorganic materials 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229910052680 mordenite Inorganic materials 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 16
- 229960002920 sorbitol Drugs 0.000 description 14
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UNXHWFMMPAWVPI-UHFFFAOYSA-N butane-1,2,3,4-tetrol Chemical compound OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-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
- 150000007513 acids Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- HEBKCHPVOIAQTA-NGQZWQHPSA-N d-xylitol Chemical compound OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- MCHWWJLLPNDHGL-KVTDHHQDSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-KVTDHHQDSA-N 0.000 description 1
- MCHWWJLLPNDHGL-UNTFVMJOSA-N (2s,3s,4s,5s)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-UNTFVMJOSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 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
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 description 1
- 235000014755 Eruca sativa Nutrition 0.000 description 1
- 244000024675 Eruca sativa Species 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- 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 1
- -1 HCl (US Pat. No. 4 Chemical class 0.000 description 1
- 101100293261 Mus musculus Naa15 gene Proteins 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Images
Classifications
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20771500P | 2000-05-26 | 2000-05-26 | |
| PCT/US2001/016571 WO2001092266A2 (en) | 2000-05-26 | 2001-05-22 | Process for the manufacture of anhydro sugar alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004501117A true JP2004501117A (ja) | 2004-01-15 |
| JP2004501117A5 JP2004501117A5 (enExample) | 2008-07-10 |
Family
ID=22771700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002500879A Abandoned JP2004501117A (ja) | 2000-05-26 | 2001-05-22 | 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 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6689892B2 (enExample) |
| EP (1) | EP1283840B1 (enExample) |
| JP (1) | JP2004501117A (enExample) |
| CN (1) | CN1446221A (enExample) |
| AU (1) | AU2001264807A1 (enExample) |
| WO (1) | WO2001092266A2 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011516574A (ja) * | 2008-04-10 | 2011-05-26 | アイオワ・コーン・プロモーション・ボード | 二無水糖の製造方法 |
| WO2016009607A1 (ja) * | 2014-07-16 | 2016-01-21 | 国立大学法人北海道大学 | 糖アルコールの脱水用固体触媒、およびその触媒を使用する二無水糖アルコールの製造方法。 |
| JP2017141171A (ja) * | 2016-02-08 | 2017-08-17 | 三菱ケミカル株式会社 | アンヒドロ糖アルコールの製造方法 |
| JP2018034075A (ja) * | 2016-08-29 | 2018-03-08 | 国立大学法人北海道大学 | マンニトールの脱水用固体触媒、およびこの触媒を使用する2,5−ソルビタン及び/又はイソマンニドの製造方法 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8479251B2 (en) * | 1999-03-31 | 2013-07-02 | Microsoft Corporation | System and method for synchronizing streaming content with enhancing content using pre-announced triggers |
| US7129052B1 (en) * | 2000-07-12 | 2006-10-31 | The United States Of America As Represented By The Department Of Health And Human Services | Peptides and their utility in modulation of behavior of cells expressing α3β1 integrins |
| US20050247807A1 (en) * | 2004-03-15 | 2005-11-10 | Wen-Ben Liu | System for automatically recycling flat glass from workpiece and method of the same |
| WO2006005070A1 (en) * | 2004-06-30 | 2006-01-12 | E.I. Dupont De Nemours And Company | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using gas sparging |
| US20060084817A1 (en) * | 2004-06-30 | 2006-04-20 | Chenault Henry K | Synthesis of aldonolactones, aldarolactones, and aldarodilactones using gas sparging |
| US7772412B2 (en) * | 2006-01-26 | 2010-08-10 | Battelle Memorial Institute | Methods for dehydration of sugars and sugar alcohols |
| US7649099B2 (en) * | 2006-01-26 | 2010-01-19 | Battelle Memorial Institute | Method of forming a dianhydrosugar alcohol |
| US7615652B2 (en) * | 2006-01-26 | 2009-11-10 | Battelle Memorial Institute | Two-stage dehydration of sugars |
| US7728156B2 (en) * | 2006-01-26 | 2010-06-01 | Battelle Memorial Institute | Method of performing sugar dehydration and catalyst treatment |
| EP2146998B1 (en) * | 2007-04-06 | 2012-03-07 | Sud-Chemie, Inc. | Sorbitol conversion process |
| EP2100972A1 (en) | 2008-03-13 | 2009-09-16 | BIOeCON International Holding N.V. | Process for converting polysaccharides in a molten salt hydrate |
| US9765084B2 (en) * | 2008-04-10 | 2017-09-19 | Iowa Corn Promotion Board | Recovery and refining of dianhydrosugars |
| BRPI1009270A2 (pt) | 2009-03-17 | 2016-05-03 | Bioecon Int Holding Nv | processo para converter um material contendo polissacarídeo a um aditivo de combustível ou a um material substituto de combustível, e, uso de açúcares dianidro derivados |
| WO2010106052A1 (en) | 2009-03-17 | 2010-09-23 | Bioecon International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| WO2010106055A1 (en) | 2009-03-17 | 2010-09-23 | Bioecon International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| WO2010106057A1 (en) | 2009-03-17 | 2010-09-23 | Bioecon International Holding N.V. | Process for converting polysaccharides in an inorganic molten salt hydrate |
| WO2012083149A1 (en) * | 2010-12-17 | 2012-06-21 | Cargill, Incorporated | Reaction product from the dehydration of sorbitol |
| US9266898B2 (en) | 2010-12-17 | 2016-02-23 | Cargill, Incorporated | Reaction product from the co-dehydration of a sugar alcohol and a polyol |
| CN102603760A (zh) * | 2011-01-24 | 2012-07-25 | 华东理工大学 | 一种抗心绞痛药物单硝酸异山梨醇酯的合成方法 |
| AU2013338445B2 (en) * | 2012-10-31 | 2017-07-27 | Archer Daniels Midland Company | Improved method of making internal dehydration products of sugar alcohols |
| JP6267240B2 (ja) * | 2013-03-05 | 2018-01-24 | アーチャー−ダニエルズ−ミッドランド カンパニー | 糖アルコールの酸脱水のための方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3229412A1 (de) * | 1982-08-06 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von dianhydrohexitol-gemischen aus hexitolen, dianhydro-idit enthaltende dianhydro-hexitol-gemischen und ihre verwendung zur herstellung von polymeren |
| DE3703257A1 (de) * | 1987-02-04 | 1988-08-18 | Huels Chemische Werke Ag | Gezielt eingestellte polyolgemische auf basis von sorbit, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von sorbitanestern |
| DE19841032A1 (de) * | 1998-09-09 | 2000-03-16 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Anhydrozuckeralkoholen |
-
2001
- 2001-05-22 EP EP01939271A patent/EP1283840B1/en not_active Revoked
- 2001-05-22 AU AU2001264807A patent/AU2001264807A1/en not_active Abandoned
- 2001-05-22 JP JP2002500879A patent/JP2004501117A/ja not_active Abandoned
- 2001-05-22 CN CN01810093A patent/CN1446221A/zh active Pending
- 2001-05-22 WO PCT/US2001/016571 patent/WO2001092266A2/en not_active Ceased
- 2001-05-24 US US09/864,465 patent/US6689892B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011516574A (ja) * | 2008-04-10 | 2011-05-26 | アイオワ・コーン・プロモーション・ボード | 二無水糖の製造方法 |
| WO2016009607A1 (ja) * | 2014-07-16 | 2016-01-21 | 国立大学法人北海道大学 | 糖アルコールの脱水用固体触媒、およびその触媒を使用する二無水糖アルコールの製造方法。 |
| JP2016022400A (ja) * | 2014-07-16 | 2016-02-08 | 国立大学法人北海道大学 | 糖アルコールの脱水用固体触媒、およびその触媒を使用する二無水糖アルコールの製造方法。 |
| JP2017141171A (ja) * | 2016-02-08 | 2017-08-17 | 三菱ケミカル株式会社 | アンヒドロ糖アルコールの製造方法 |
| JP2018034075A (ja) * | 2016-08-29 | 2018-03-08 | 国立大学法人北海道大学 | マンニトールの脱水用固体触媒、およびこの触媒を使用する2,5−ソルビタン及び/又はイソマンニドの製造方法 |
| WO2018042932A1 (ja) * | 2016-08-29 | 2018-03-08 | 国立大学法人北海道大学 | マンニトールの脱水用固体触媒、およびこの触媒を使用する2,5-ソルビタン及び/又はイソマンニドの製造方法 |
| CN109475851A (zh) * | 2016-08-29 | 2019-03-15 | 国立大学法人北海道大学 | 甘露糖醇的脱水用固体催化剂及使用此催化剂的2,5-脱水山梨醇和/或去水甘露糖醇的制造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6689892B2 (en) | 2004-02-10 |
| CN1446221A (zh) | 2003-10-01 |
| AU2001264807A1 (en) | 2001-12-11 |
| US20020028959A1 (en) | 2002-03-07 |
| WO2001092266A2 (en) | 2001-12-06 |
| EP1283840A2 (en) | 2003-02-19 |
| EP1283840B1 (en) | 2005-02-09 |
| WO2001092266A3 (en) | 2002-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1283840B1 (en) | Process for the manufacture of anhydro sugar alcohols | |
| EP2271636B1 (en) | Dianhydrosugar production process | |
| US6407266B2 (en) | Continuous process for the manufacture of anhydro sugar alcohols and reactor useful therefor | |
| EP1999134B1 (en) | Process for the production of anhydrosugar alcohols | |
| EP2933256B1 (en) | Method for preparing an anhydrosugar alcohol using hydrol | |
| JP2005523325A (ja) | ジアンヒドロ糖アルコールを製造するための同時反応分離方法 | |
| JPH11209361A (ja) | 5員環式又は6員環式エーテルの製法及びアンヒドロヘキシトール混合物 | |
| EP2714696B1 (en) | A method for preparation of anhydrosugar alcohols | |
| KR101970853B1 (ko) | 헥소스 용액으로부터 스팀의 존재 하에 5-히드록시메틸푸르푸랄 (hmf)을 제조하는 방법 | |
| WO2020038592A1 (en) | Method for producing sclareolide | |
| KR20140101848A (ko) | 스팀 증류에 의한 반응 용액에서의 5-히드록시메틸푸르푸랄 (hmf) 분리 | |
| WO1992003439A1 (fr) | Procede de production de composes d'acetal | |
| JP6298816B2 (ja) | 不均一触媒反応による、水素化糖の少なくとも1種の分子内脱水生成物を含む組成物の合成方法 | |
| KR20180127342A (ko) | 박막 증발기 상에서의 증류 단계에 의해 디안하이드로헥시톨을 생산하기 위한 방법 | |
| JP2021127343A (ja) | アンヒドロ糖アルコールの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20080303 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080520 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080520 |
|
| RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20081127 |
|
| RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20081127 |
|
| RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20090221 |
|
| A762 | Written abandonment of application |
Free format text: JAPANESE INTERMEDIATE CODE: A762 Effective date: 20110218 |