CS225538B3 - Regeneration of d-glucose from the epidermic mixture of d-glucose and d-mannose - Google Patents
Regeneration of d-glucose from the epidermic mixture of d-glucose and d-mannose Download PDFInfo
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- CS225538B3 CS225538B3 CS657082A CS657082A CS225538B3 CS 225538 B3 CS225538 B3 CS 225538B3 CS 657082 A CS657082 A CS 657082A CS 657082 A CS657082 A CS 657082A CS 225538 B3 CS225538 B3 CS 225538B3
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- Czechoslovakia
- Prior art keywords
- glucose
- mannose
- mixture
- regeneration
- aniline
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims 2
- 230000008929 regeneration Effects 0.000 title claims 2
- 238000011069 regeneration method Methods 0.000 title claims 2
- 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 title 2
- GZCGUPFRVQAUEE-KVTDHHQDSA-N aldehydo-D-mannose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O GZCGUPFRVQAUEE-KVTDHHQDSA-N 0.000 title 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 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001323 aldoses Chemical class 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000006345 epimerization reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Description
Vynález sa týká apdeobu regenerócie D-glukózy z epimerizačnej zmesi D-glukózy a D-manózy po odstránení D-manózy vo formě N-fanylglykozidu a je závislý na AO 196 996.The invention relates to an apdeob of D-glucose regeneration from an epimerization mixture of D-glucose and D-mannose after removal of D-mannose in the form of N-fanyl glycoside and is dependent on AO 196 996.
Epimerizáciou katalyzovanou molybdénanovými iónmi glukózy (D-glukózy/v. Bílik: Chám. zvěsti 26, 183 (1972)^/, D-(1-3H)glukózy/v. Bilik, L. Pat ruš, V. Farkaš: Chám. zvaeti 29, 690 (1975)7 D-/U-l4C/glukózy /V. Bilik, R. Sandtnarová, Z· Krátký, L. Pat ruš: Chem. zvěsti 34, 518 (1980)/,) resp. manózy /b-manózy/” V. Bilik: Chám. zvěsti 26, 183 (1972)/, L-manózy /V. Bilik: Chem. zveeti 26, 187 (1972)/) sa získá rovnovážná zmea glukózy a manózy v pomere 3:1«Molybdate ions catalyzed epimerization of glucose (D-glucose / in. Bílik Cham. Rumors 26, 183 (1972) ^ /, D (1-3H) glucose / in. Bilik, L. Pat Rus, V. Farkas Cham Zvaeti 29, 690 (1975) 7 D- (U- 14 C) glucose (V. Bilik, R. Sandtnarova, Z Kratky, L. Pat ruš: Chem. Rums 34, 518 (1980)), respectively. mannose / b-mannose / ”V. Bilik: Cham. rumors 26, 183 (1972)], L-mannose (V). Bilik: Chem. 26, 187 (1972)], a 3: 1 equilibrium glucose / mannose balance is obtained.
Z rovnovážnáj zmesi epimórnych aldóz sa 45 až 55 % glukózy zlska kryštalizáciou z alkoholických roztokov /V. Bilik: Chám. zvěsti 26, 183 (1972), ibidi 26, 187 (1972)/. Izolácia manózy ea uekutočňuja vo forma jej fenylhydrazónu V. Bilik: Chem. zvaati 26, 183 (1972)/ alebo N-fanylglykozylaminu/V. Bilik, K. Tihlárik: Chem. zvaati 28, 106 (1974)/, připadne chromatografickými metodami /V. Bilik et al.: Chám. zvaati 29, 690 (1975), ibidi 34, 518 (1980)/. Z N-fenylglykozidov sa aldózy uvolňujú vytěsňováním anilínu najčastajšie benzaldehydom /Ř.L. Whistler, 3.N, BeMiller: Methods Carbohyd. Chem·, Vol. I, p. 79, Academie Press, New York 19627, ala tiež formaldehydom /?. Fujita,From an equilibrium mixture of epimeric aldoses, 45 to 55% glucose is obtained by crystallization from alcoholic solutions / V. Bilik: I see. rumors 26, 183 (1972), ibid. 26, 187 (1972)]. The isolation of mannose ea takes place in the form of its phenylhydrazone V. Bilik: Chem. 26, 183 (1972)] or N-phanylglycosylamine (V). Bilik, K. Tihlárik: Chem. 28, 106 (1974)], optionally by chromatographic methods (V). Bilik et al .: Cham. 29, 690 (1975), ibid 34, 518 (1980)]. Of the N-phenylglycosides, aldoses are released by the displacement of aniline most commonly by benzaldehyde (RL). Whistler, 3.N, BeMiller: Methods Carbohyd. Chem., Vol. I, p. 79, Academic Press, New York 19627, and also formaldehyde. Fujita,
T. Sáto: Bull. Chem. Soc. Oapan 33, 353 (1960)/, připadne hydrolýzou kyselinou sirovou resp· kyselinou mravčou /í<· Butler, S, Laland, VV.G. Overend, M. Stacy: 3. Chem·T. Sato: Bull. Chem. Soc. Oapan 33, 353 (1960)], optionally by hydrolysis with sulfuric acid or formic acid (Butler, S, Laland, VV.G. Overend, M. Stacy: 3. Chem ·
Soc. 1433 (1950)/, alebo kyselinou octovou /F. Weygand,Soc. 1433 (1950)], or acetic acid (F). Weygand,
W* Parkow, P. Kuhner: Chám. Bar. 84, 594 (1951)/ a hydrolýzou technikou preháňania vodoou parou /V· Bilik et al.: Chem. zvěsti 27, 547 (1973), ibidi 28, 106 (1974), ibidi 30, 359 (1976)/. Navrhovaný spůsob využívá na hydrolýzu N-fenylglykozylaminov a odstraňovania anilínu z vodných roztokov silné kyslý iónomenič.W * Parkow, P. Kuhner: Cham. Bar. 84, 594 (1951)] and by hydrolysis by a water vapor sweep technique [Bilik et al., Chem. rumors 27, 547 (1973), ibid. 28, 106 (1974), ibid. 30, 359 (1976)]. The proposed method uses a strong acid ion exchanger for the hydrolysis of N-phenylglycosylamines and the removal of aniline from aqueous solutions.
Podstata vynálezu spočívá v tom, že po reakci! aldóz 8 anilinom sa 0-manóza odstréni vo forma krystalického N-fenyl-O-manozylaminu a z matečných vodných roztokov ea O-glukóza regeneruje hydrolýzou silná kyalým ionomaničom - kataxom v H+-cykle, pričom ea z roztoku aúčasne odstránia i zvyšky anilinu.The essence of the invention is that after the reaction! aldose 8 by aniline, O-mannose is removed in the form of crystalline N-phenyl-O-mannose amine and recovered from the mother liquors e and O-glucose by hydrolysis with a strong ionic ionic catax in the H + -cycle, ea also removing aniline residues from the solution.
i,and,
225 538225 538
Výhodou navrhovaného spósobu regenerácie D-glukózy z epimérizačných zmesi D-glukózy a D-manózy je, že D-glukózový roztok je vhodný pre další cyklus epimerizácie D-glu kozy zameranej na přípravu D-manózy, připadne na iné zúžitkovanle - skvasenie, při recyklizácii íónomenlčov minerálny ml kyselinami sa regeneruje tiež anilin a netoxické odpadové vody sú vhodné pre biologické čistenie·The advantage of the proposed method of D-glucose regeneration from epimerization mixtures of D-glucose and D-mannose is that the D-glucose solution is suitable for the next cycle of D-glucose epimerization aimed at the preparation of D-mannose, eventually other utilization - fermentation, aniline and non-toxic waste water are suitable for biological treatment
Příklad 1Example 1
Zmee D-glukózy (300 g), vody (900 ml), molybdénanu amonného (1,5 g), kyseliny octovej (6 ml) sa zahrieva na 95 až 100°C pó dobu 4 hodiny· Roztok sa zahustí a teplý sirupovitý zvyšok sa vleje do etanolického roztoku anilinu (900 ml 96 % etanolu a 120 ml anilínu). Roztok sa pramieša a nechá stáť pri teplote miestnosti 8 až 20 hodin· Vylúčený biely kryštalický N-fenyl-D-manozylamin (80 až 90 g) sa odfiltruje a D-manóza z něho uvolní hydrolýzou eilne kyslým iónomeničom podlá AO č. 196 996. Matečný roztok po odstráneni kryštalického N-fenyl-D-manozylaminu sa zahustí na polovičný objem, ktorý ea zriedi vodou (800 ml), potom sa přidá silné kyslý iónomenič (Ostion KS 0210) v H+-cykle (1000 ml) a zmes sa mieša pri teplote miestnosti 4 hodiny, iónomenič ea odfiltruje, premyje vodou, filtrát sa zahusti na 15 až 25 % obsah D-glukózy (refraktometrická kontrola), upraví ea kyselinou octovou na pH 4 až 6 a uskutočni sa další cyklus epimerizácie, izolácie D-manózy a regnerácia D-glukózy ako je už opisané.A mixture of D-glucose (300 g), water (900 ml), ammonium molybdate (1.5 g), acetic acid (6 ml) was heated to 95-100 ° C for 4 hours. · The solution was concentrated and a warm syrup residue Pour into ethanolic aniline solution (900 mL of 96% ethanol and 120 mL of aniline). The precipitated white crystalline N-phenyl-D-mannosylamine (80-90 g) is filtered off and D-mannose is liberated therefrom by hydrolysis with an acidic ion exchanger according to AO no. 196 996. After removal of the crystalline N-phenyl-D-manozylamine, the mother liquor is concentrated to half volume, which is diluted with water (800 ml), then a strong acid ion exchanger (Ostion KS 0210) in H + -cycle (1000 ml) is added. and the mixture is stirred at room temperature for 4 hours, the ion exchanger ea is filtered off, washed with water, the filtrate is concentrated to a 15-25% D-glucose content (refractometric control), adjusted to pH 4-6 with acetic acid and a further epimerization cycle is performed. isolating D-mannose and recovering D-glucose as described above.
Vynález má uplatnenie pri výrobě komerčně zaujímavej D-manózy, ktorá ea využívá v chémii a biochémii sacharidov.The invention has application in the production of commercially interesting D-mannose, which uses carbohydrate chemistry and biochemistry.
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS657082A CS225538B3 (en) | 1982-09-13 | 1982-09-13 | Regeneration of d-glucose from the epidermic mixture of d-glucose and d-mannose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS657082A CS225538B3 (en) | 1982-09-13 | 1982-09-13 | Regeneration of d-glucose from the epidermic mixture of d-glucose and d-mannose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS225538B3 true CS225538B3 (en) | 1984-02-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS657082A CS225538B3 (en) | 1982-09-13 | 1982-09-13 | Regeneration of d-glucose from the epidermic mixture of d-glucose and d-mannose |
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| CS (1) | CS225538B3 (en) |
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1982
- 1982-09-13 CS CS657082A patent/CS225538B3/en unknown
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