JP2009526131A5 - - Google Patents
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- Publication number
- JP2009526131A5 JP2009526131A5 JP2008554231A JP2008554231A JP2009526131A5 JP 2009526131 A5 JP2009526131 A5 JP 2009526131A5 JP 2008554231 A JP2008554231 A JP 2008554231A JP 2008554231 A JP2008554231 A JP 2008554231A JP 2009526131 A5 JP2009526131 A5 JP 2009526131A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- solution
- erythrose
- arabinonic
- electrolytic
- 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
- 239000002253 acid Substances 0.000 claims description 35
- 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 24
- 238000000034 method Methods 0.000 claims description 24
- 238000006114 decarboxylation reaction Methods 0.000 claims description 16
- YTBSYETUWUMLBZ-UHFFFAOYSA-N D-Erythrose Natural products OCC(O)C(O)C=O YTBSYETUWUMLBZ-UHFFFAOYSA-N 0.000 claims description 15
- YTBSYETUWUMLBZ-IUYQGCFVSA-N D-erythrose Chemical compound OC[C@@H](O)[C@@H](O)C=O YTBSYETUWUMLBZ-IUYQGCFVSA-N 0.000 claims description 15
- 206010056474 Erythrosis Diseases 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 12
- 239000004386 Erythritol Substances 0.000 claims description 12
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 12
- 229940009714 erythritol Drugs 0.000 claims description 12
- 235000019414 erythritol Nutrition 0.000 claims description 12
- 229910002804 graphite Inorganic materials 0.000 claims description 10
- 239000010439 graphite Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- 239000003729 cation exchange resin Substances 0.000 claims description 5
- 230000000911 decarboxylating effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 239000011888 foil Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 229930091371 Fructose Natural products 0.000 claims 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 3
- 239000005715 Fructose Substances 0.000 claims 3
- 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 claims 3
- 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 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims 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 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-VSOAQEOCSA-N L-altropyranose Chemical compound OC[C@@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-VSOAQEOCSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000005868 electrolysis reaction Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000005895 oxidative decarboxylation reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 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 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000007770 graphite material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 230000037427 ion transport Effects 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002296 pyrolytic carbon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77154906P | 2006-02-08 | 2006-02-08 | |
| US60/771,549 | 2006-02-08 | ||
| US11/482,214 | 2006-07-07 | ||
| US11/482,214 US7955489B2 (en) | 2006-02-08 | 2006-07-07 | Methods for the electrolytic production of erythrose or erythritol |
| PCT/US2006/047610 WO2007092079A2 (en) | 2006-02-08 | 2006-12-13 | Methods for the electrolytic production of erythrose or erythritol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009526131A JP2009526131A (ja) | 2009-07-16 |
| JP2009526131A5 true JP2009526131A5 (https=) | 2012-05-10 |
| JP5579990B2 JP5579990B2 (ja) | 2014-08-27 |
Family
ID=38332884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008554231A Active JP5579990B2 (ja) | 2006-02-08 | 2006-12-13 | エリスロースまたはエリスリトールの電解製造法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7955489B2 (https=) |
| EP (1) | EP1982005B1 (https=) |
| JP (1) | JP5579990B2 (https=) |
| KR (1) | KR101367233B1 (https=) |
| CN (1) | CN101336313B (https=) |
| BR (1) | BRPI0621312A2 (https=) |
| CA (1) | CA2642127C (https=) |
| DK (1) | DK1982005T3 (https=) |
| RU (1) | RU2433211C2 (https=) |
| WO (1) | WO2007092079A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9133554B2 (en) | 2006-02-08 | 2015-09-15 | Dynamic Food Ingredients Corporation | Methods for the electrolytic production of erythritol |
| US9169571B2 (en) * | 2008-08-08 | 2015-10-27 | Dynamic Food Ingredients Corporation | Methods for the electrolytic production of xylo-pent-1,5-diose |
| WO2011011492A2 (en) * | 2009-07-23 | 2011-01-27 | Ceramatec, Inc. | Decarboxylation cell for production of coupled radical products |
| US8506789B2 (en) | 2009-07-23 | 2013-08-13 | Ceramatec, Inc. | Method of producing coupled radical products |
| US9051656B2 (en) | 2009-07-23 | 2015-06-09 | Ceramatec, Inc. | Electrochemical synthesis of aryl-alkyl surfacant precursor |
| US9957622B2 (en) | 2009-07-23 | 2018-05-01 | Field Upgrading Limited | Device and method of obtaining diols and other chemicals using decarboxylation |
| US9206515B2 (en) | 2009-07-23 | 2015-12-08 | Ceramatec, Inc. | Method of producing coupled radical products via desulfoxylation |
| WO2011133906A2 (en) * | 2010-04-23 | 2011-10-27 | Ceramatec, Inc. | Electrochemical synthesis of aryl-alkyl surfactant precursor |
| US9493882B2 (en) | 2010-07-21 | 2016-11-15 | Ceramatec, Inc. | Custom ionic liquid electrolytes for electrolytic decarboxylation |
| US9057137B2 (en) | 2010-08-05 | 2015-06-16 | Ceramatec, Inc. | Method and device for carboxylic acid production |
| US8821710B2 (en) | 2011-01-25 | 2014-09-02 | Ceramatec, Inc. | Production of fuel from chemicals derived from biomass |
| EP2964814B1 (en) * | 2013-03-08 | 2020-08-19 | Enlighten Innovations Inc. | Method of obtaining dienes using decarboxylation |
| CN105283585B (zh) * | 2013-03-12 | 2019-01-18 | Dfi 美国有限责任公司 | 糖类电解脱羧方法 |
| MX371528B (es) * | 2013-08-16 | 2020-01-31 | Dfi Usa Llc | Metodos para la descarboxilacion y reduccion electrolitica simultanea de azucares. |
| CN104558063B (zh) * | 2014-12-30 | 2017-12-01 | 复旦大学 | 一种利用生物质糖制备d‑赤藓糖的方法 |
| WO2016210281A1 (en) | 2015-06-25 | 2016-12-29 | Dynamic Food Ingredients Corporation | Method for the production of 2,4-dihydroxybutyric acid |
| TWI631218B (zh) * | 2017-02-16 | 2018-08-01 | 義守大學 | 麥芽糖醇的製造方法 |
| CN109778222B (zh) * | 2017-11-13 | 2020-08-28 | 万华化学集团股份有限公司 | 一种成对电极同时制备醛类物质和芳香酯的方法及所使用的电极 |
| CN109368761A (zh) * | 2018-10-25 | 2019-02-22 | 苏州浩波科技股份有限公司 | 一种用于去除安赛蜜水溶液中koh的装置 |
| CN109748403B (zh) * | 2018-12-08 | 2021-10-08 | 上海电力学院 | 一种用于抑止硫酸钙垢形成的高分子阻垢剂及其制备方法 |
| CN109778221B (zh) * | 2018-12-08 | 2020-09-01 | 上海电力学院 | 一种由柠檬酸及其钠盐制备的聚羧酸及其制备方法 |
| CA3142054A1 (en) * | 2019-05-28 | 2020-12-03 | The Charlotte Mecklenburg Hospital Authority D/B/A Atrium Health | Compositions and methods of making ribitol |
| KR20230058095A (ko) * | 2020-08-28 | 2023-05-02 | 디에프아이 유에스에이, 엘엘씨. | L-크실론산으로부터 l-트레온산 염을 생산하는 방법 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3632802A (en) | 1968-12-06 | 1972-01-04 | Univ Southern Illinois | Oxidation of carbohydrates |
| DE2628056A1 (de) * | 1976-06-23 | 1978-01-05 | Basf Ag | Verfahren zur herstellung von alkalisalzen der arabonsaeure |
| US4457813A (en) * | 1983-03-04 | 1984-07-03 | Monsanto Company | Electrolysis cells and electrolytic processes |
| JPH01116091A (ja) * | 1987-10-28 | 1989-05-09 | Bridgestone Corp | 炭素電極 |
| CS271428B1 (en) * | 1987-12-03 | 1990-09-12 | Vladimir Ing Csc Jiricny | Method of d-arabinose production |
| 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 |
| RU2050422C1 (ru) * | 1992-04-14 | 1995-12-20 | Акционерное общество закрытого типа "Деко" | Способ получения лимонной кислоты |
| WO1994029498A1 (en) * | 1993-06-10 | 1994-12-22 | Daikin Industries, Ltd. | Process for producing 1,4-dihydroperfluorobutane |
| CA2114492C (en) * | 1994-01-28 | 2000-09-05 | Wu Li | Aqueous electrochemical preparation of insertion compounds and use in non-aqueous rechargeable batteries |
| RU2086654C1 (ru) * | 1995-01-17 | 1997-08-10 | Дагестанский Государственный Университет Им.В.И.Ленина | Способ получения сахарата кальция |
| DE19620861A1 (de) * | 1996-05-23 | 1997-11-27 | Basf Ag | Verfahren zur elektrochemischen Reduktion organischer Verbindungen |
| FI102962B (fi) * | 1996-06-24 | 1999-03-31 | Xyrofin Oy | Menetelmä ksylitolin valmistamiseksi |
| FR2753451B1 (fr) * | 1996-09-16 | 1998-11-27 | Roquette Freres | Procede de fabrication de d-erythrose |
| JPH10298192A (ja) * | 1997-04-30 | 1998-11-10 | Ajinomoto Co Inc | エリスロースの製造法 |
| FR2769314B1 (fr) * | 1997-10-07 | 2000-02-11 | Roquette Freres | Procede de fabrication d'un aldose ou d'un derive d'aldose |
| FR2784382B1 (fr) | 1998-10-13 | 2002-01-18 | Roquette Freres | Procede de conversion de sucres oxydes en sucres hydrogenes par hydrogenation catalytique |
| FI106853B (fi) | 1998-11-18 | 2001-04-30 | Xyrofin Oy | Menetelmä polyolien valmistamiseksi arabinoksylaania sisältävästä materiaalista |
| JP2001203007A (ja) * | 2000-01-20 | 2001-07-27 | Matsushita Electric Ind Co Ltd | 電極、その製造方法、およびそれを用いた電池 |
| EP1727778A4 (en) | 2004-03-26 | 2010-11-17 | Purdue Research Foundation | PROCESSES FOR PRODUCING XYLITOL |
-
2006
- 2006-07-07 US US11/482,214 patent/US7955489B2/en active Active
- 2006-12-13 KR KR1020087021799A patent/KR101367233B1/ko active Active
- 2006-12-13 RU RU2008135977/07A patent/RU2433211C2/ru active
- 2006-12-13 CN CN2006800524320A patent/CN101336313B/zh active Active
- 2006-12-13 WO PCT/US2006/047610 patent/WO2007092079A2/en not_active Ceased
- 2006-12-13 BR BRPI0621312-0A patent/BRPI0621312A2/pt active Search and Examination
- 2006-12-13 CA CA2642127A patent/CA2642127C/en active Active
- 2006-12-13 JP JP2008554231A patent/JP5579990B2/ja active Active
- 2006-12-13 EP EP06845367.9A patent/EP1982005B1/en active Active
- 2006-12-13 DK DK06845367.9T patent/DK1982005T3/da active
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