GB443901A - Improvements in or relating to the manufacture of ascorbic acid and its analogues - Google Patents
Improvements in or relating to the manufacture of ascorbic acid and its analoguesInfo
- Publication number
- GB443901A GB443901A GB2520534A GB2520534A GB443901A GB 443901 A GB443901 A GB 443901A GB 2520534 A GB2520534 A GB 2520534A GB 2520534 A GB2520534 A GB 2520534A GB 443901 A GB443901 A GB 443901A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- keto
- water
- ascorbic acid
- methyl
- 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.)
- Expired
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
Abstract
In the preparation of ascorbic acid and its analogues from ketose sugars, the intermediate 2-keto-acids are prepared by oxidizing the ketose sugars with hot aqueous nitric acid, as such or prepared in situ. When the required stage of oxidation is attained, the reaction is stopped by rapid cooling, dilution if necessary and neutralization with a weak alkali. The keto-acid is isolated in a purified form by precipitating the clarified solution with organic solvents, extracting with water and liberating the acid by acidification. For conversion into ascorbic acid and its analogues, the keto-acid is esterified and treated in known manner, e.g. with an alkali alkoxide (cf. Specification 430,264). According to the examples: (1) l-sorbose, prepared from l-sorbitol by the action of B-xylinum, is heated on the water bath for a few minutes with dilute nitric acid and the solution then poured into ice water, neutralized with barium carbonate, and the clarified solution diluted with methyl alcohol and extracted with water; after liberation of the acid with sulphuric acid, methyl alcohol is added to the concentrated solution, which is then distilled under reduced pressure, whereby simultaneous removal of water and esterification is effected; the anhydrous syrup containing methyl-2-keto-l-gulonate is then heated with sodium methoxide in methyl alcohol solution and acidified with methyl alcoholic hydrogen chloride and l-ascorbic acid isolated by extraction with and crystallization from ethyl alcohol; (2) the same procedure as in (1) is followed, except that the syrup of the ester is allowed to crystallize out before the treatment with sodium methoxide; the syrupy mother liquid is then further esterified and treated with sodium methoxide; (3) fructose is heated with dilute aqueous nitric acid on a water bath for a few minutes and the procedure of (2) carried out, with intermediate isolation of methyl-2-keto-d-gluconate prior to its conversion into d-arabo-ascorbic acid (3-keto-d-glucono-lactone).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2520534A GB443901A (en) | 1934-09-01 | 1934-09-01 | Improvements in or relating to the manufacture of ascorbic acid and its analogues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2520534A GB443901A (en) | 1934-09-01 | 1934-09-01 | Improvements in or relating to the manufacture of ascorbic acid and its analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB443901A true GB443901A (en) | 1936-03-02 |
Family
ID=10223929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2520534A Expired GB443901A (en) | 1934-09-01 | 1934-09-01 | Improvements in or relating to the manufacture of ascorbic acid and its analogues |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB443901A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1142861B (en) * | 1957-05-31 | 1963-01-31 | Miles Lab | Process for the production of isoascorbic acid |
| US4202942A (en) | 1978-07-20 | 1980-05-13 | Pfizer Inc. | Destruction by fermentation of 2-ketogluconate in the presence of 2-ketogulonate |
-
1934
- 1934-09-01 GB GB2520534A patent/GB443901A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1142861B (en) * | 1957-05-31 | 1963-01-31 | Miles Lab | Process for the production of isoascorbic acid |
| US4202942A (en) | 1978-07-20 | 1980-05-13 | Pfizer Inc. | Destruction by fermentation of 2-ketogluconate in the presence of 2-ketogulonate |
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