CS232647B1 - Preparation method of d-arabinose by means of oxidative degradation of d-calcium gluconate - Google Patents
Preparation method of d-arabinose by means of oxidative degradation of d-calcium gluconate Download PDFInfo
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- CS232647B1 CS232647B1 CS836749A CS674983A CS232647B1 CS 232647 B1 CS232647 B1 CS 232647B1 CS 836749 A CS836749 A CS 836749A CS 674983 A CS674983 A CS 674983A CS 232647 B1 CS232647 B1 CS 232647B1
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- arabinose
- calcium
- preparation
- oxidative degradation
- gluconate
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- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000010525 oxidative degradation reaction Methods 0.000 title claims description 7
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 title 1
- 229960004494 calcium gluconate Drugs 0.000 title 1
- 239000004227 calcium gluconate Substances 0.000 title 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims abstract description 19
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims abstract description 19
- SRBFZHDQGSBBOR-OWMBCFKOSA-N L-ribopyranose Chemical compound O[C@H]1COC(O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-OWMBCFKOSA-N 0.000 claims abstract description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 10
- NEEHYRZPVYRGPP-IYEMJOQQSA-L calcium gluconate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O NEEHYRZPVYRGPP-IYEMJOQQSA-L 0.000 claims abstract description 7
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims abstract description 4
- 235000011092 calcium acetate Nutrition 0.000 claims abstract description 4
- 239000001639 calcium acetate Substances 0.000 claims abstract description 4
- 229960005147 calcium acetate Drugs 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 229950006191 gluconic acid Drugs 0.000 description 4
- 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 3
- 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 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 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000012208 gluconic acid Nutrition 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 229910001447 ferric ion Inorganic materials 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 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 description 1
- 241001517013 Calidris pugnax Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- -1 D-glucose dithioacetal Chemical class 0.000 description 1
- 238000006994 Koenigs-Knorr glycosidation reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Vynález sa týká sposobu přípravy D-arabinózy z D-glukomátu vápenatého. Podstata vynálezu spočívá v tom, že D-glukonát vápenatý sa odbúrava na D-arabinózu dvomi ekvivalentami peroxidu vodíka vo vodnom roztoku octanu vápenatého o koncentrácii 0 až 0,3 mol. 1_1 za přítomnosti katalytických množstiev meďmatých iónov pri teplote 20 až 30 °C po dobu 5 až 7 hodin. Vynález má použitie v chemickom priemysle a biochémii.The present invention relates to a process for preparing D-arabinose from calcium D-glucomate. Essence of the invention is that calcium D-gluconate is degraded to D-arabinose by two equivalents of hydrogen peroxide in water calcium acetate solution 0 to 0.3 mol. 11 in the presence of catalytic amounts of copper ions at temperature 20 to 30 ° C for 5 to 7 hours. The invention has utility in the chemical industry and biochemistry.
Description
Vynález sa týká přípravy D-arabinózy oxidačným odbúraním D-glukonátu vápenatého.The invention relates to the preparation of D-arabinose by oxidative degradation of calcium D-gluconate.
Metódy přípravy D-arabinózy sú hlavně založené na skracovaní uhlíkatého reťazca kyseliny D-glukónovej, připadne D-glukózy, resp. vhodných derivátov týchto zlúčenín. Najčastejsie sa pre tento účel využívá Ruffovo odbúranie a odbúranie ditioacetálov D-glukózy, menej často Wohlovo odbúranie, Wermanovo odbúranie a Hunsdickerová reakcia [J. Staněk, M. Černý, J. Kocourek, J. Pacák: Monosacharidy, Nakl. ČSAV, Praha 1960, s. 88]. Využívá sa tiež alkalický rozklad peroxozlúčenín připravených Koenigs-Knorrovou reakciou terc.butylperoxidu s hrómacetyl D-glukózou, resp. acetylchloridom kyseliny per-O-acetyl-D-glukónovej [M. Schulz, P. Berlin: Angew,. Chem. 79, 940 (1967)] a pre přípravu D-5(U-14C jarabinózy oxidačně odbúranie 4-nitrofenylhydrazónu D-(U-14C)-glukózy [V. Bílik, P. Biely, M. Matulová: Chem. zvěsti 33, 782 (1979)]. Praktické uplatnenie přípravy D-arabinózy vo váčších množstvách je založené na oxidačnom odbúraní sodnej soli kyseliny D-glukónovej kyselinou chlórnou [R. L. Whistler, J. N. BeMiller: Methods in Carbohydrate Chemistry, Academie Press, New York — London 1962, s. 71] a oxidačným odbúraním vápenatej soli kyseliny D-glukónovej ekvivalentným množstvom peroxidu vodíka za katalytického účinku železitých iónov [H. C. Fletcher, H. W. Diehl, C. S. Hudson: J. Amer. Chem. Soc. 72, 4546 (1950)].Methods for the preparation of D-arabinose are mainly based on shortening the carbon chain of D-gluconic acid, respectively D-glucose, respectively. suitable derivatives of these compounds. The most commonly used for this purpose are Ruff's degradation and D-glucose dithioacetal degradation, less frequently Wohn's degradation, Werman's degradation and Hunsdicker reaction [J. Stanek, M. Cerny, J. Kocourek, J. Pacak: Monosaccharides, Nakl. ČSAV, Praha 1960, p. 88]. Alkaline decomposition of the peroxy compounds prepared by Koenigs-Knorr reaction of tert-butyl peroxide with chromoacetyl D-glucose, respectively, is also utilized. acetyl chloride per-O-acetyl-D-gluconic acid [M. Schulz, P. Berlin: Angew ,. Chem. 79, 940 (1967)] and for the preparation of D-5 (U- 14 C jarabinose by oxidative degradation of 4-nitrophenylhydrazone D- (U- 14 C) -glucose [V. Bilik, P. Biely, M. Matulova: Chem. 33, 782 (1979)] The practical application of the preparation of D-arabinose in larger amounts is based on the oxidative degradation of the sodium salt of D-gluconic acid with hypochlorous acid [RL Whistler, JN BeMiller: Methods in Carbohydrate Chemistry, Academic Press, New York - London 1962 71] and oxidative degradation of the calcium salt of D-gluconic acid with an equivalent amount of hydrogen peroxide under the catalytic action of ferric ions [HC Fletcher, HW Diehl, CS Hudson: J. Amer. Chem. Soc., 72, 4546 (1950)].
Podstata vynálezu spočívá v tom, že D-glukonát vápenatý sa odbúrava na D-arabinózu dvomi ekvivalentami peroxidu vodíka vo vodnom roztoku octanu vápenatého o koncentrácii 0 až 0,3 mol. 1_1 za přítomnosti katalytických množstiev meďnatých iónov pri teplote 20 až 30 °C po dobu 5 až 7 hodin.SUMMARY OF THE INVENTION Calcium D-gluconate is degraded to D-arabinose by two equivalents of hydrogen peroxide in an aqueous solution of calcium acetate having a concentration of 0 to 0.3 mol. 1 _1 in the presence of catalytic amounts of copper ions at a temperature of 20-30 ° C for 5-7 hours.
Výhodou navrhovaného' sposobu přípravy D-arabinózy je, že konverzia D-glukonátu vápenatého na D-arabinózu oproti oxidačnému odbúraniu katalyzovaného železitými iónmi je až 0' 1/3 vyššia. Vypracovaný postup je velmi jednoduchý, nenáročný na technologické zariadenia a všetky potřebné chemikálie sú bežne dostupné.An advantage of the proposed process for the preparation of D-arabinose is that the conversion of calcium D-gluconate to D-arabinose over ferric ion catalyzed oxidative degradation is up to 0 1/3. The elaborated procedure is very simple, it does not require any technological equipment and all necessary chemicals are commercially available.
Příklad 1Example 1
Vo vodě (2000 ml) sa rozpustí D-glukonát vápenatý (220 g), octan vápenatý (60 g), síran meďnatý (3 g) a potom sa do roztoku pri teplote 20 až 30 °C postupné přidává (v priebehu 1 až 2 hodin) 30 % peroxid vodí647 ka (220 ml). Reakčná zmes sa nechá stát pri teplote miestnosti 5 hodin a nakoniec sa přidá kyselina sírová (800 ml) o koncentrácii 1 mol. I-1 a nechá ďalej stát najmenej 2 hodiny. Vylúčený síran vápenatý sa odfiltruje, filtrát zahustí a destilačný zvyšok sa prevarí metanolem (1000 ml). Metanolový roztok sa přefiltruje, primerane zahustí (na 1/3 objem) a nechá kryštalizovať pri teplote miestnosti 24 až 48 hodin, čím sa získá prvý kryštalický podiel D-arabinózy (48 g, t. j. 32 %). Matečný roztok sa deionizuje prídavkom iónmeniča katexu (400 ml silné kyslý katex — Ostion KS 0210) a po jeho odstránení prídavkom iónomeniča anexu (400 ml silné bázicky anex — Ostion AT 0209). Premývacie roztoky sa zahustia a destilačný zvyšok sa kryštalizuje z metanolu (200 ml), čím sa získá druhý kryštalický podiel D-arabinózy (28 g, t. j. 18 %). Matečný roztok sa zahustí a chromatografuje na stípci 2,5 x 120 cm iónomeniča Dowex 50 W, X-8, 75 až 150 μτη v Ca-cykle elúciou vodou o prietoku 30 ml/h, pričom sa získá třetí podiel D-arabinózy (33 g, t. j. 22 % v elúčnom objeme 500 až 900 ml).Calcium D-gluconate (220 g), calcium acetate (60 g), copper sulphate (3 g) are dissolved in water (2000 ml) and then gradually added to the solution at 20 to 30 ° C (over 1 to 2 hours). hours) 30% hydrogen peroxide 647 ka (220 mL). The reaction mixture was allowed to stand at room temperature for 5 hours and finally 1 mol of sulfuric acid (800 mL) was added. I -1 and allow to stand for at least 2 hours. The precipitated calcium sulfate is filtered off, the filtrate is concentrated and the distillation residue is boiled with methanol (1000 ml). The methanol solution is filtered, appropriately concentrated (to 1/3 volume) and allowed to crystallize at room temperature for 24 to 48 hours to give a first crystalline fraction of D-arabinose (48 g, ie 32%). The mother liquor is deionized by addition of a cation exchange ion exchanger (400 ml strong acid cation exchanger - Ostion KS 0210) and after removal by addition of an anion exchanger (400 ml strong basic anion exchanger - Ostion AT 0209). The washings were concentrated and the distillation residue was crystallized from methanol (200 mL) to give a second crystalline portion of D-arabinose (28 g, ie 18%). The mother liquor is concentrated and chromatographed on a 2.5 x 120 cm Dowex 50 W, X-8 ion exchange column, 75-150 μτη in a Ca-cycle, eluting with water at a flow rate of 30 ml / h to give a third crop of D-arabinose (33 g, ie 22% in an elution volume of 500 to 900 ml).
Příklad 2Example 2
Postupuje sa ako je uvedené v příklade 1 s tým rozdielom, že namiesto síranu meďnatého sa používá octan meďnatý. Pri ďalšom spracovaní po odstránení síranu vápenatého sa filtrát deionizuje prídavkom iónomeniča katexu a potom anexu. Premývacie roztoky sa zahustia a destilačný zvyšok kryštalizuje z metanolu (300 ml), čím sa získá prvý podiel kryštalickej D-arabinózy (86 g, t. j. 57 percent). Matečný roztok sa zahustí a chromatografie na stípci iónomeniča Dowex 50 W ako je opísané v příklade 1, Čím sa získá druhý podiel D-arabinózy (21 g, t. j. 14 %).The procedure is as described in Example 1 except that copper acetate is used instead of copper sulfate. For further processing after removal of the calcium sulfate, the filtrate is deionized by the addition of an ion exchange resin and then an anion exchange resin. The washings were concentrated and the distillation residue was crystallized from methanol (300 mL) to give a first crop of crystalline D-arabinose (86 g, i.e. 57 percent). The mother liquor was concentrated and chromatographed on a Dowex 50 W ion exchange column as described in Example 1 to give a second crop of D-arabinose (21 g, i.e. 14%).
Chromatograf icky čistá (S-D-arabinóza (získaná rozpuštěním A g D-arabinózy v A ml vody a A ml metanolu) má t. t. 159 až 160° Celsia a [or]D 23 —153° ± 2° (3 min.] —103° ± 1° (c 2, voda). Literatúra [J.Chromatographically pure (SD-arabinose (obtained by dissolving A g of D-arabinose in A ml of water and A ml of methanol) has a melting point of 159-160 ° C and [ .alpha. ] D @ 23 -153 ± 2 [deg.] ° ± 1 ° (c 2, water) Literature [J.
Staněk et al. Monosacharidy, Nakl. ČSAV, Praha 1960, s. 79] pre β,D-arabinózu udává t. t. 158 až 159 °C a [a]D —175° -> —105° (voda).Stanek et al. Monosaccharides, Nakl. ČSAV, Praha 1960, p. 79] for β, D-arabinose gives tt 158-159 ° C and [α] D -175 ° -> -105 ° (water).
Vynález má využitie pre přípravu D-arabinózy, ktorá sa vo velkých množstvách využívá na přípravu D-ribózy a tá ďalej na přípravu riboflavínu. Súčasne D-arabinóza sa využívá ako východisková zlúčenina pre rad dalších syntéz a tiež pri štúdiu biochemických premien sacharidov.The invention has utility for the preparation of D-arabinose, which is used in large quantities for the preparation of D-ribose, and further for the preparation of riboflavin. At the same time, D-arabinose is used as a starting compound for a number of other syntheses and also for the study of carbohydrate biochemical transformations.
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| CS836749A CS232647B1 (en) | 1983-09-16 | 1983-09-16 | Preparation method of d-arabinose by means of oxidative degradation of d-calcium gluconate |
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| CS836749A CS232647B1 (en) | 1983-09-16 | 1983-09-16 | Preparation method of d-arabinose by means of oxidative degradation of d-calcium gluconate |
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| CS232647B1 true CS232647B1 (en) | 1985-02-14 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012167012A2 (en) | 2011-06-03 | 2012-12-06 | Dynamic Food Ingredients Corporation | Methods for the electrolytic production of erythritol |
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1983
- 1983-09-16 CS CS836749A patent/CS232647B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012167012A2 (en) | 2011-06-03 | 2012-12-06 | Dynamic Food Ingredients Corporation | Methods for the electrolytic production of erythritol |
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| Publication number | Publication date |
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| CS674983A1 (en) | 1984-06-18 |
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