CS214431B1 - The process of preparing D-mannos - Google Patents

The process of preparing D-mannos Download PDF

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Publication number
CS214431B1
CS214431B1 CS56181A CS56181A CS214431B1 CS 214431 B1 CS214431 B1 CS 214431B1 CS 56181 A CS56181 A CS 56181A CS 56181 A CS56181 A CS 56181A CS 214431 B1 CS214431 B1 CS 214431B1
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Czechoslovakia
Prior art keywords
mannose
aniline
preparing
phenyl
glucose
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CS56181A
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Czech (cs)
Slovak (sk)
Inventor
Jozef Kubala
Vojtech Bilik
Jan Caplovic
Frantisek Rendos
Milan Repas
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Jozef Kubala
Vojtech Bilik
Jan Caplovic
Frantisek Rendos
Milan Repas
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Application filed by Jozef Kubala, Vojtech Bilik, Jan Caplovic, Frantisek Rendos, Milan Repas filed Critical Jozef Kubala
Priority to CS56181A priority Critical patent/CS214431B1/en
Publication of CS214431B1 publication Critical patent/CS214431B1/en

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Abstract

Vynález sa týká sposobu přípravy D-manózy z epimerizačnej zmesi D-glukozy. Podstata vynálezu spočívá v tom, že zo zmesi D-manózy a D-glukozy sa D-manoza po reakcii e anilínom selektívne viaže vo formě krystalického N-fenyl manozylamínu, z ktorého sa D-manoza uvolňuje hydrolýzou a anilín sa odstráni destiláciou vodnou parou.The invention relates to a method for preparing D-mannose from an epimerization mixture of D-glucose. The essence of the invention lies in the fact that from a mixture of D-mannose and D-glucose, D-mannose, after reaction with aniline, is selectively bound in the form of crystalline N-phenyl mannosylamine, from which D-mannose is released by hydrolysis and aniline is removed by steam distillation.

Description

214 431 1214 431 1

Vynález sa týká sposobu přípravy D-manózy z epimerizačnej zmesi D-glukozy. D-manoza sa raože připravit hydrolýzou mananov zo semien palmy Phytelephae macrocar-pa - R. Rieass Ber. 22, 609, /1889/, z riasy Porthyra umbilicalls - C.S. Hudson, E.L.Jackson; Am.Chem. Soe. 56. 958, /1944/., buněčných stien kvasinlek Saccharomycescerevislae - J. šandula, A. Vojtková; Folia Mlcrobiol. 19. 94, /1974/., alebo oxidácioumanitolu B, Fischer, J. Hirschberger; Ber. 21. 1805, /1889/. V, Bílik čsl. patent 149051popisuje*přípravu D-manozy epimerizáciou D-glukozy za katalytického účinku molybdénovýchionov, kde z epiraerizáčnej zmesi sa čiastočne D-glukóza odstráni kryštalizáciou a potomsa D-raanóza izoluje vo formě fenylhydrazonu. Přípravy D-manozy hydrolýzou mananov resp.oxidáciou manitolu sú značné obtiažne a vyžadujú si špeciálne suroviny připadne enzýmy.Příprava D-manózy epimerizáciou D-glukózy je jednoduchšia, avšak nevýhodou tohoto sposobuje izolácia D-manozy cez jej fenylhydrazon. Spásob přípravy D-manozy sa stává komplikova-ný, náročný, taško realizovatelný v prevádzkovom meradle. Navrhovaný sposob přípravyD-manózy z izomerizačnej zmesi cez N-fenyl manozylamín je v porovnaní s uvedenými meto-dami přípravy podstatné jednoduchší.The present invention relates to a process for preparing D-mannose from an epimerizing mixture of D-glucose. D-mannose is prepared by hydrolysis of mannans from Phytelephae macrocar-pa - R. Rieass Ber. 22, 609, (1889), from Porthyra umbilicalls algae - C.S. Hudson, E. L. J. Jackson; Am.Chem. Soe. 56. 958, (1944), the cell walls of yeast Saccharomycescerevislae - J. shandula, A. Vojtkova; Folia Mlcrobiol. 19, 94, (1974), or oxidation of mannitol B, Fischer, J. Hirschberger; Ber. 21, 1805, (1889). V, Bilik CSL. No. 149051 discloses the preparation of D-mannos by epimerizing D-glucose under the catalytic effect of molybdenum, wherein the D-glucose is partially removed from the epiridization mixture by crystallization and then D-rane is isolated as phenylhydrazone. Preparations of D-mannos by the hydrolysis of mannans or by the oxidation of mannitol are very difficult and require special raw materials or enzymes. Preparation of D-mannose by epimerization of D-glucose is simpler, but the disadvantage of this is the isolation of D-mannose through its phenylhydrazone. The process of preparing D-mannose becomes complicated, demanding, and can be carried out on a commercial scale. The proposed process for the preparation of D-mannose from the isomerization mixture through N-phenyl manozylamine is substantially simpler compared to the said methods of preparation.

Podstata vynálezu spočívá v tom, že zo zmesi D-,-lukozy a D-manozy po reakcii s ani-línom selektívne viaže vo formě krystalického N-fenyl manozylamínu, z ktorého sa D-manozauvolňuje hydrolýzou a anilín odstráni destiláciou vodnou parou. Výhodou navrhovaného spSsobu přípravy D-manozy je*· regenerovatel’nost surovin, čím sa zlacňuje sposob výroby a zabraňuje znečistovaniuživotného prostredia, potřebné technologické zariadenie je jednoduché a chemikálie bežne dostupné,umožňuje pracovat s látkami zdraviu raenej škodlivými,poskytuje přípravu výrobku o vysokej čistotě. Příklad 1SUMMARY OF THE INVENTION The invention is based on the fact that it selectively binds from the mixture of D -, - Lukozy and D - mannose, in the form of crystalline N - phenyl manozylamine, from which D - mannose is liberated by hydrolysis and the aniline is removed by steam distillation. The advantage of the proposed method of preparing D-mannos is that the raw materials are regenerated, thereby making the production process less expensive and preventing the environment from being polluted, the equipment required is simple and the chemicals commonly available, allowing the handling of harmful substances, provides the preparation of a high purity product. Example 1

Vodná zmee 30 % roztoku D-glukózy a /0,06 %/ kyseliny molybdénovej sa zahrievá 2hodiny pri 90 °C. Roztok sa ochladí a deionizuje na koloně naplněněj ionomeničom SBW aAc“ formě. Perkolovaný roztok sa vyzráža prídavkom koncentrovanej kyseliny octovéj/0,4 %/, absolutného etanolu /5 %/ a anilínu /6,5 %/, Kryštalizácia N-fenyl manozylamínunastáva okamžité, podporuje sa miešaním a chladením. Krystalický N-fenyl manozylamín saodfiltruje na nuči a premyje studenou vodou. Příklad 2An aqueous solution of 30% D-glucose and (0.06%) molybdenic acid solution is heated at 90 ° C for 2 hours. The solution is cooled and deionized on a column packed with an SBW aAc ion exchanger. The percolated solution is precipitated by the addition of concentrated acetic acid (0.4%), absolute ethanol (5%) and aniline (6.5%). The crystallization of N-phenyl mannosylamine is instantaneous, supported by mixing and cooling. The crystalline N-phenyl manozylamine is filtered on a suction filter and washed with cold water. Example 2

Rozklad N-fenyl manozylamínuDecomposition of N-phenyl manozylamine

Vodná suspenzla /10 %/ N-fenyl manozylamínu sa destiluje vodnou parou za úplnéhouvol’nenia anilínu. Vzniklý roztok D-manózy sa odfarbí aktívnym uhlím, přefiltruje na vá-kuovej rotačnej odparka a zahustí na hustý sirup. Kryštalizácia sa uskutoční z absolutné-ho etanolu v pomere U5. Získá sa krystalická D-manóza v 20 % výtažku v přepočte na povod-nú surovinu.The aqueous suspension (10%) of N-phenyl manozylamine is distilled by steam to complete the elimination of the aniline. The resulting D-mannose solution was decolorized with charcoal, filtered on a vacuum rotary evaporator and concentrated to a thick syrup. The crystallization is carried out from absolute ethanol U5. Crystalline D-mannose is obtained in a 20% yield calculated as the flood raw material.

Vynález má rozsiahle použitie pri stúdiu biochemických procesov živej hmoty a vThe invention has extensive use in the study of biochemical processes in living matter and in the living environment

Claims (1)

2 214 431 praktickora živote v medicíně a potravinárakom priemyele. P R E D i« li T V Y N A L li / U Sposob přípravy D-manózy z jej epimerizačných zmeaí :;a vyznačuje tým, že aa D·aelektívne viaže anilínom vo formě krystalického N-fenyl manozylaminu, z kterého aaD-manóza uvolní hydrolýzou a anilín odstráni deatiláciou vodnou parou. manoza2 214 431 practitioner life in medicine and food industry industry. Although the method of preparing D-mannose from its epimerization mixtures is characterized in that aa D · aelectively binds aniline in the form of crystalline N-phenyl manozylamine, from which aaD-mannose is released by hydrolysis and aniline is removed by aqueous dehydration. steam. manoza
CS56181A 1981-01-26 1981-01-26 The process of preparing D-mannos CS214431B1 (en)

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