CH187934A - Process for the production of 1-ascorbic acid (C vitamin). - Google Patents

Process for the production of 1-ascorbic acid (C vitamin).

Info

Publication number
CH187934A
CH187934A CH187934DA CH187934A CH 187934 A CH187934 A CH 187934A CH 187934D A CH187934D A CH 187934DA CH 187934 A CH187934 A CH 187934A
Authority
CH
Switzerland
Prior art keywords
ascorbic acid
acid
vitamin
production
keto
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH187934A publication Critical patent/CH187934A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/62—Three oxygen atoms, e.g. ascorbic acid

Description

  

  Verfahren zur Herstellung von     1-Ascorbinsäure        (C-Vitamin).       Die     physiologisch        wichtige        1-Ascorbin-          säure        ist    vor     kurzem    ,synthetisch aus     1-gy-          loson        (-        1-Lyxoson)    durch Einwirkung von  Blausäure und nachträgliche saure Versei  fung     bereitet    worden.

   Sie hat sich mit den  in der Natur aufgefundenen Körpern als  identisch und auch biologisch als     wirksames          C-Vitamin        erwiesen        (Helv.        Chim.    Acta 16,  1933, S. 1019).  



  Dieses erste Verfahren hat den     Vorteil     eines sehr allgemeinen Anwendungsbereiches;  es hat bisher in allen untersuchten Fällen die       entsprachenden        3-Ketosäuren,        bezw.    ihre An  hydride ergeben. Für die spezielle Berei  tung der     1-Ascorbinsäure    hat es dagegen den  Nachteil, dass das nötige     Ausgangsmaterial,     das     1-Xyloson,    nur     isehr    .schwierig und auf  kostspieligem Wege zu beschaffen ist. Auf  der Suche nach einer technisch besser brauch  baren Methode wurde ein weiterer Weg auf  gefunden.

   Nach diesem neuen Weg wird     1-          Ascorbinsäure    dadurch gewonnen,     ,dass        2-          Keto-l-gulonsäure    gegebenenfalls nach vor  heriger     Veresterung        zunächst    mit zur Enoli-         sierun,g    geeigneten     alkalischen        Mitteln,        .dann     mit starken Säuren     behandelt        .wird        (Patent     Nr. 174208).  



       Statt    durch     alkalische        Mittel    kann die  Umlagerung der     2-Keto-l-gulonsäure    oder  ihrer     mit    Säure leicht spaltbaren Derivate  auch durch     Erwärmung    bei saurer Reaktion  erfolgen (Patent Nr.     1.80810    und     Zusätze).     Dabei     wird    die     Erwärmung    der     2-Keto-1-          gulensäure    oder ihrer mit Säure leicht spalt  baren Derivate     in    wässeriger oder alkoholi  scher Lösung durchgeführt.  



  Es wurde nun gefunden,     dass    sich die  Umlagerung der     2-Keto-l-gulonsäure    beson  ders vorteilhaft gestaltet,     wenn    sie durch     Er-          wärmung    bei saurer     Reaktion    in Gegenwart  von indifferenten     Verdünnungsmitteln,    wie  zum     Beispiel    Chloroform,     Dioxan,    vorgenom  men     wird.     



  <I>Beispiel:</I>  40 g     2-Keto-1        :gulonsäure    werden in einem  Gemisch von 80     cma    Chloroform und 40     cmg          10%iger    alkoholischer Salzsäure 60 Stunden  unter Rühren am     Rückflusskühler    gekocht.      bann wird     abfiltriert    und     mit    einem Gemisch  von Chloroform und Alkohol gewaschen. Es  werden 27,13 g     1-Ascorbinsäure    erhalten, die  bei der     Titration    mit Jod     einen    Reinheits  grad von     9,8,6        %        zeigen.  



  Process for the production of 1-ascorbic acid (C vitamin). The physiologically important 1-ascorbic acid was recently prepared synthetically from 1-gyloson (- 1-lyxoson) by the action of hydrocyanic acid and subsequent acidic saponification.

   It has proven to be identical to the bodies found in nature and also to be biologically effective as a C vitamin (Helv. Chim. Acta 16, 1933, p. 1019).



  This first method has the advantage of being very general in scope; so far it has the corresponding 3-keto acids, respectively. their to hydride yield. For the special preparation of 1-ascorbic acid, on the other hand, it has the disadvantage that the necessary starting material, 1-xyloson, is very difficult and expensive to obtain. In the search for a technically more useful method, another way was found.

   According to this new way, 1-ascorbic acid is obtained by treating 2-keto-1-gulonic acid, if necessary after previous esterification, first with alkaline agents suitable for enolization, then with strong acids (patent no. 174208 ).



       Instead of using alkaline agents, the rearrangement of 2-keto-l-gulonic acid or its derivatives, which are easily cleaved with acid, can also be carried out by heating with an acidic reaction (Patent No. 1.80810 and additives). The 2-keto-1-gulenic acid or its derivatives, which can easily be cleaved with acid, are heated in an aqueous or alcoholic solution.



  It has now been found that the rearrangement of 2-keto-l-gulonic acid turns out to be particularly advantageous if it is carried out by heating in an acidic reaction in the presence of inert diluents, such as chloroform, dioxane, for example.



  <I> Example: </I> 40 g of 2-keto-1: gulonic acid are boiled in a mixture of 80 cma chloroform and 40 cm g of 10% alcoholic hydrochloric acid for 60 hours with stirring on the reflux condenser. It is then filtered off and washed with a mixture of chloroform and alcohol. 27.13 g of 1-ascorbic acid are obtained, which when titrated with iodine show a degree of purity of 9.6%.

Claims (1)

PATENTANSPRÜCii Verfahren zur Herstellung von 1-Ascor- binsäure, dadurch .gekennzeichnet, dass man 2-geto-l-bulonsäure in Gegenwart von indif- ferenten Verdünnungsmitteln bqi saurer Re- aktion erwärmt. PATENT APPLICATION Process for the production of 1-ascorbic acid, characterized in that 2-geto-l-bulonic acid is heated in the presence of indifferent diluents bqi acidic reaction.
CH187934D 1935-06-18 1935-11-26 Process for the production of 1-ascorbic acid (C vitamin). CH187934A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH180810T 1935-06-18
CH187934T 1935-11-26

Publications (1)

Publication Number Publication Date
CH187934A true CH187934A (en) 1936-11-30

Family

ID=25720464

Family Applications (1)

Application Number Title Priority Date Filing Date
CH187934D CH187934A (en) 1935-06-18 1935-11-26 Process for the production of 1-ascorbic acid (C vitamin).

Country Status (1)

Country Link
CH (1) CH187934A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987000839A1 (en) * 1985-08-09 1987-02-12 The Lubrizol Corporation Production of l-ascorbic acid from 2-keto-l-gulonic acid

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1987000839A1 (en) * 1985-08-09 1987-02-12 The Lubrizol Corporation Production of l-ascorbic acid from 2-keto-l-gulonic acid

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