GB627700A - Improvements in processes for the preparation of laevo-ascorbic acid and related compounds - Google Patents
Improvements in processes for the preparation of laevo-ascorbic acid and related compoundsInfo
- Publication number
- GB627700A GB627700A GB13243/46A GB1324346A GB627700A GB 627700 A GB627700 A GB 627700A GB 13243/46 A GB13243/46 A GB 13243/46A GB 1324346 A GB1324346 A GB 1324346A GB 627700 A GB627700 A GB 627700A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- keto
- distillation
- arrangement
- gulonic
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/16—Preventing evaporation or oxidation of non-metallic liquids by applying a floating layer, e.g. of microballoons
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Furan Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
l-Ascorbic acid or its analogues is prepared by re-arranging 2-keto-l-gulonic acid or an analogue or derivative thereof by heating with concentrated aqueous hydrohalide acid and an inert organic solvent immiscible with the concentrated aqueous acid. By " concentrated " is meant 20 per cent concentration or more. Preferably the mixture is distilled azeotropically under atmospheric or reduced pressure to remove a part of the organic solvent, which is added continuously or periodically to maintain a constant volume, and to remove substantially all other volatile components. The re-arranged product is recovered from the resulting crystalline suspension or slurry by filtration. The re-arrangement may take place concurrently with distillation in a continuous process. Non-polar solvents such as benzene, toluene, xylene, " Solvesso " (Registered Trade Mark), chlorbenzene and tetrachlorethane are used although polar solvents such as butyl or amyl alcohol may be admixed to dissolve tarry substances and to ensure that the solvent layer floats on the acid solution to prevent foaming and air oxidation. The polar solvent may be admixed before or during the re-arrangement or distillation or used to wash the crystalline product. In an example diacetone 2-keto-l-gulonic acid dissolved in an equal weight of 38 per cent hydrochloric acid is fed continuously to a distillation apparatus containing boiling toluene at atmospheric pressure. Acetone is liberated and re-arrangement is completed in the 2 to 3 minute interval required for azeotropic removal of hydrochloric acid. The hydrochloric acid solution is added at approximately one-fifth of the distillation rate of the azeotropic mixture and the volume of distilland maintained constant by continuous addition of toluene, preferably hot or in the vapour state and the continuous removal of crystalline slurry. The crude l-ascorbic acid obtained by filtration is washed with n-butyl alcohol to remove coloured impurities. In other examples, the initial materials are 2-keto-l-gulonic acid, methyl 2-keto-l-gulonic acid, 2-keto-l-galactonic acid and diacetone-2-keto-d-gluconic acid-the lastnamed yielding d-arascorbic acid-and the organic solvents are xylene, benzene, chlorbenzene and a mixture of tetrachlorethane and isobutyl alcohol.ALSO:l-Ascorbic acid or its analogues is prepared by re-arranging 2-keto-l-gulonic acid or an analogue or derivative thereof by heating with concentrated aqueous hydrohalide acid and an inert organic solvent immiscible with the conconcentrated aqueous acid. By "concentrated" is meant 20 per cent concentration or more. Preferably the mixture is distilled azeotropically under atmospheric or reduced pressure to remove a part of the organic solvent, which is added continuously or periodically to maintain a constant volume, and to remove substantially all other volatile components. The re-arranged product is recovered from the resulting crystalline suspension or slurry by filtration. The re-arrangement may take place concurrently with distillation in a continuous process. Non-polar solvents such as benzene, toluene, xylene, "Solvesso" (Registered Trade Mark), chlorbenzene and tetrachlorethane are used although polar solvents such as butyl or amyl alcohol may be admixed to dissolve tarry substances and to ensure that the solvent layer floats on the acid solution to prevent foaming and air oxidation. The polar solvent may be admixed before or during the re-arrangement or distillation or used to wash the crystalline product. In an example, diacetone 2-keto-l-gulonic acid dissolved in an equal weight of 38 per cent hydrochloric acid is fed continuously to a distillation apparatus containing boiling toluene at atmospheric pressure. Acetone is liberated and re-arrangement is completed in the 2 to 3 minute interval required for azeotropic removal of hydrochloric acid. The hydrochloric acid solution is added at approximately one-fifth of the distillation rate of the azeotropic mixture and the volume of distilland maintained constant by continuous addition of toluene, preferably hot or in the vapour state and the continuous removal of crystalline slurry. The crude l-ascorbic acid obtained by filtration is washed with n-butyl alcohol to remove coloured impurities. In other examples, the initial materials are 2-keto-l-gulonic acid, methyl 2-keto-l-gulonic acid, 2-keto-l-galactonic acid and diacetone-2-keto-d-gluconic acid, the last-named yielding d-arascorbic acid, and the organic solvents are xylene, benzene, chlorbenzene and a mixture of tetrachlorethane and isobutyl alcohol.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US627700XA | 1945-05-16 | 1945-05-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB627700A true GB627700A (en) | 1949-08-15 |
Family
ID=22044681
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB13243/46A Expired GB627700A (en) | 1945-05-16 | 1946-05-01 | Improvements in processes for the preparation of laevo-ascorbic acid and related compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB627700A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0950897A1 (en) * | 1996-12-20 | 1999-10-20 | Daiichi Pure Chemicals Co., Ltd. | Method for stabilizing liquid reagent and reagent unit |
-
1946
- 1946-05-01 GB GB13243/46A patent/GB627700A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0950897A1 (en) * | 1996-12-20 | 1999-10-20 | Daiichi Pure Chemicals Co., Ltd. | Method for stabilizing liquid reagent and reagent unit |
EP0950897A4 (en) * | 1996-12-20 | 2000-06-14 | Daiichi Pure Chemicals Co Ltd | Method for stabilizing liquid reagent and reagent unit |
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