MXPA00001339A - Process for preparing l-ascorbic acid - Google Patents
Process for preparing l-ascorbic acidInfo
- Publication number
- MXPA00001339A MXPA00001339A MXPA/A/2000/001339A MXPA00001339A MXPA00001339A MX PA00001339 A MXPA00001339 A MX PA00001339A MX PA00001339 A MXPA00001339 A MX PA00001339A MX PA00001339 A MXPA00001339 A MX PA00001339A
- Authority
- MX
- Mexico
- Prior art keywords
- acid
- keto
- gulonic
- ascorbic acid
- preparing
- Prior art date
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims abstract description 17
- 229960005070 ascorbic acid Drugs 0.000 title claims abstract description 17
- CIWBSHSKHKDKBQ-DUZGATOHSA-N (+)-Ascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 title claims abstract description 14
- 239000002211 L-ascorbic acid Substances 0.000 title claims abstract description 14
- 235000000069 L-ascorbic acid Nutrition 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims abstract description 18
- VBUYCZFBVCCYFD-NUNKFHFFSA-N 2-dehydro-L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-NUNKFHFFSA-N 0.000 claims abstract description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 14
- 239000011707 mineral Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VBUYCZFBVCCYFD-YVZJFKFKSA-N 2-dehydro-L-gluconic acid Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-YVZJFKFKSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Abstract
A process is disclosed for preparing L-ascorbic acid by reaction of 2-keto-L-gulonic acid with concentrated mineral acid at temperatures of between 40 and 80°C.
Description
PROCESS FOR PREPARING L-ASCORBIC ACID PBSCRIPCIQff PB frft INVENTION The object of the invention is a process for preparing L-ascorbic acid by reacting 2-keto-L-glulonic acid with a concentrated mineral acid at temperatures between 40 and 80 ° C. A particular subject of the invention is a process for preparing L-ascorbic acid, characterized in that the reaction is carried out at temperatures between 50 and 70 ° C. The known methods of preparing ascorbic acid are carried out in a single step and by reacting 2-keto-L-gulonic acid with an acid. US Pat. No. 2,185,383 describes the reaction of 2-keto-L-gulonic acid with concentrated hydrochloric acid, using acetic acid as the solvent. In the unexamined Japanese Patent Application No. 58-177986 a method is described for preparing L-ascorbic acid in which a solution of sodium 2-keto-L-gulonate in ethanol and acetone with hydrochloric acid is first neutralized. In the Japanese Patent Examined Application No. 48-15931, the reaction of 2-keto-L-gulonic acid with a mineral acid in an inert solvent and in the presence of a surfactant substance is described. In World Patent No. 87/00839, the preparation of L-ascorbic acid from 2-keto-L-gulonic anhydride and in the presence of a REF .: 32,365 surfactant is also described. European Patent No. 0 324 261 in British Patent 2,205,567 describes the reaction of 2-keto-L-gulonic acid with an acid in a mixture of inert solvents and in the presence of a surfactant substance. The reaction of 2-cets-L-gulonic acid with 36% hydrochloric acid is described in German Patent No.
2939052. In this document, L-ascorbic acid is obtained with a yield of 87% after a reaction at 100 ° C and distillation of hydrochloric acid. During investigations on the synthesis of ascorbic acid it was surprisingly discovered that high yields are obtained when the reaction is carried out at temperatures between 40 and 80 ° C, in particular between 50 and 70 ° C. It has been shown that the particularly preferred temperature range for the reaction is between 57 and 63 ° C. The novel process of the invention makes it possible to obtain high yields of L-ascorbic acid by lactonizing 2-keto-gulonic acid with a concentrated mineral acid. It is particularly advantageous that at low temperatures the ascorbic acid obtained decomposes considerably more slowly than in processes known from the state of the art (for example, that of German patent No. 2939052 which elapses at 100 ° C). From this last one derives the advantage of a lower consumption of energy and a minor contamination of the environment. In contrast to the processes of the prior art, the process of the invention also has the advantage that it can be worked in the absence of organic solvents.
It has been shown that in the process of the invention it is convenient to use 2-keto-L-gulonic acid and hydrochloric acid in a 1: 3 ratio. Therefore, a subject of the invention is also a process in which 2-keto-L-gluconic acid and mineral acid are used in a ratio of 1: 3. However, the concentration can vary within wide margins. The process can be carried out in concentrated or diluted form. The weight ratio between 2-keto-L-gulonic acid and the concentrated mineral acid can be, for example, between 10: 1 to 1:10. The range of 1: 2 is preferred to
1: 4, the ratio of 1: 3 being particularly convenient. Mineral acid is understood, for example, as hydrochloric, phosphoric or sulfuric acid. The concentrated mineral acids are preferred. Another object of the invention is a process as described, characterized in that the concentrated hydrochloric acid is used as the mineral acid.
It is also an object of the invention a method, as described, characterized in that a mixture consisting of 2-keto-L-gulonic acid and concentrated mineral acid is heated to the desired reaction temperature. The reaction time is usually between 1 and 5 hours, in particular between 2 and 4 hours, especially a reaction time of about 3 hours is preferred.
The preparation is carried out by methods known per se, such as, for example, treatment with active carbon, filtering, removal of the solvent and crystallization. Corresponding to the process according to the invention are the yields of L-ascorbic acid usually above 90%, so that the expendable purification steps can be omitted. Above and below all temperatures are given in ° C. EXAMPLE 1 100 g of 2-keto-L-gulonic acid are added to 300 g of 37% hydrochloric acid. The reaction mixture is then heated to 58 ° C and this temperature is maintained for 3 hours. After removing hydrochloric acid and working the mixture in the usual way, L-ascorbic acid is obtained with a yield of 91.4% of theory.
EXAMPLE 2 100 g of 2-keto-L-gulonic acid are added to 300 g of 37% hydrochloric acid. The reaction mixture is then heated to 59-60 ° and this temperature is maintained for 3 hours. After removing the hydrochloric acid and working the mixture in the usual way, the L-ascorbic acid is obtained with a yield of 90.2% of theory. EXAMPLE 3 100 g of 2-keto-L-gulonic acid are added to 300 g of 37% hydrochloric acid. The reaction mixture is then heated to 59-60 ° and this temperature is maintained for 1.5 hours. After removing the hydrochloric acid and working the mixture in the usual way, the L-ascorbic acid is obtained with a yield of 88.4% of theory. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.
Having described the invention as above, property is claimed as contained in the following:
Claims (5)
1. - Process for preparing L-ascorbic acid, characterized in that the 2-keto-L-gulonic acid is reacted with a concentrated mineral acid at a temperature comprised between 40 and 80 ° C.
2. Method according to claim 1, characterized in that the reaction is carried out at temperatures between 50 and 70 ° C.
3. Method according to claim 1 or 2, characterized in that the ratio between 2-keto-L-gulonic acid and mineral acid is 1: 3.
4. Process according to one of claims 1 to 3, characterized in that the concentrated hydrochloric acid is used as the mineral acid.
5. Method according to one of claims 1 to 4, characterized in that a mixture composed of acid is carried 2-keto-L-gulonic and concentrated mineral acid at the desired reaction temperature.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734086.5 | 1997-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00001339A true MXPA00001339A (en) | 2001-05-07 |
Family
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