DE10212322A1 - Production of alkali salts of alpha-keto-carboxylic acids, for use e.g. in special diets, involves adding sodium carbonate to an aqueous suspension of the calcium salt and removing calcium carbonate by filtration - Google Patents
Production of alkali salts of alpha-keto-carboxylic acids, for use e.g. in special diets, involves adding sodium carbonate to an aqueous suspension of the calcium salt and removing calcium carbonate by filtrationInfo
- Publication number
- DE10212322A1 DE10212322A1 DE2002112322 DE10212322A DE10212322A1 DE 10212322 A1 DE10212322 A1 DE 10212322A1 DE 2002112322 DE2002112322 DE 2002112322 DE 10212322 A DE10212322 A DE 10212322A DE 10212322 A1 DE10212322 A1 DE 10212322A1
- Authority
- DE
- Germany
- Prior art keywords
- salt
- alkali
- keto
- ions
- calcium
- 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.)
- Withdrawn
Links
- 150000001447 alkali salts Chemical class 0.000 title claims abstract description 15
- 159000000007 calcium salts Chemical class 0.000 title claims abstract description 9
- 238000001914 filtration Methods 0.000 title claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000007900 aqueous suspension Substances 0.000 title abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 title description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 title description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 title description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 title description 2
- 235000005911 diet Nutrition 0.000 title 1
- 230000037213 diet Effects 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 17
- 150000007513 acids Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910001424 calcium ion Inorganic materials 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 3
- -1 α- Keto acid alkali salts Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000004715 keto acids Chemical class 0.000 description 2
- 238000009938 salting Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000017924 poor diet Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Das vorliegende Verfahren ist auf die Herstellung von α- Ketocarbonsäuren gerichtet. Insbesondere beschäftigt sich das Verfahren mit der Umsalzung von Calciumsalzen von α- Ketocarbonsäuren in Alkalisalze derselben. The present process is based on the production of α- Ketocarboxylic acids directed. In particular deals the process with the salting of calcium salts of α- Ketocarboxylic acids in alkali salts thereof.
α-Ketocarbonsäuren werden z. B. in der stickstoffarmen Ernährung bei Niereninsuffizienz eingesetzt, häufig in Form ihrer relativ gut wasserlöslichen Alkalisalze. Es ergibt sich aus dieser Anwendung, dass die eingesetzten α- Ketosäurealkalisalze äußerst rein sein müssen. α-Ketocarboxylic acids are e.g. B. in the nitrogen poor Diet used in renal failure, often in the form their relatively readily water-soluble alkali salts. It results from this application that the α- Keto acid alkali salts must be extremely pure.
In der US 4912255 ist ein ähnliches Verfahren bereits für die Verbindung Phenylpyruvat vorgeschlagen worden. In US 4912255 a similar method is already for the compound phenylpyruvate has been proposed.
Aufgabe der Erfindung war die Angabe eines weiteren Verfahrens zur Herstellung der Alkalisalze von α- Ketocarbonsäuren, mit dem auch die anderen physiologisch interessanten α-Ketocarbonsäuren in einem technischen Prozess nach ökonomischen wie ökologischen Gesichtspunkten erfolgreich hergestellt werden können. The object of the invention was to provide another Process for the preparation of the alkali salts of α- Ketocarboxylic acids, with which the other physiologically interesting α-ketocarboxylic acids in a technical Process according to economic and ecological aspects can be successfully manufactured.
Diese Aufgabe wird anspruchsgemäß gelöst. This task is solved according to the requirements.
Dadurch, dass man in einem Verfahren zur Herstellung von
Alkalisalzen von α-Ketocarbonsäuren folgendes Prozedere
anwendet:
- a) Suspendieren von Calciumsalzen von α-Ketocarbonsäuren in Wasser,
- b) Zugabe eines Salzes des gewünschten Alkimetalls, welches ein Anion besitzt, das mit Calciumionen in Wasser schwerlöslich ist,
- c) Abfiltrieren des gebildeten schwerlöslichen Calciumsalzes,
- d) Isolieren des Alkalisalzes der α-Ketocarbonsäure aus der wässrigen Lösung,
By using the following procedure in a process for the preparation of alkali salts of α-ketocarboxylic acids:
- a) suspending calcium salts of α-ketocarboxylic acids in water,
- b) adding a salt of the desired alkali metal which has an anion which is sparingly soluble in water with calcium ions,
- c) filtering off the poorly soluble calcium salt formed,
- d) isolating the alkali salt of the α-ketocarboxylic acid from the aqueous solution,
Als α-Ketcarbonsäuren werden dabei bevorzugt Keto-Leu,
Keto-Val, Keto-Phe oder Keto-Ile eingesetzt.
Keto-Leu, Keto-Val, Keto-Phe or Keto-Ile are preferably used as α-ketcarboxylic acids.
Im Prinzip ist der Fachmann in der Wahl der Alkaliionen frei, doch eignen sich aufgrund wirtschaftlicher Erwägungen am besten Natriumionen für das benannte Verfahren. In principle, the expert is in the choice of alkali ions free, but are suitable due to economic considerations preferably sodium ions for the named method.
Als Anionen dienen alle solche, die mit Calcium in Wasser schwer lösliche Salze bilden und keine physiologisch negativen Auswirkungen auf das zu generierende Produkt besitzen. Aus ökonomischen Gründen sind die Anionen Carbonationen, Hydrogencarbonationen, Sulfationen oder Phosphationen bevorzugt einzusetzen. All those containing calcium in water serve as anions form poorly soluble salts and not physiologically negative effects on the product to be generated have. For economic reasons, the anions are Carbonate ions, hydrogen carbonate ions, sulfate ions or Preferably use phosphate ions.
Die Isolierung des gebildeten Alkalisalzes der α- Ketocarbonsäure kann nach dem Fachmann bekannten Verfahren erfolgen. Ggf. engt man die wässrige Lösung etwas ein und gibt vorzugsweise ein wasserlösliches organisches Lösungsmittel, wie Ketone oder Alkohole wie z. B. Aceton oder Ethanol, zur Salzlösung hinzu, um das gewünschte Produkt auszufällen. The isolation of the alkali salt of the α- Ketocarboxylic acid can be prepared by methods known to those skilled in the art respectively. Possibly. the aqueous solution is concentrated a little and preferably gives a water-soluble organic Solvents such as ketones or alcohols such as. B. acetone or ethanol, to the saline solution to achieve the desired Precipitate product.
Alternativ kann das Alkalisalz der α-Ketocarbonsäure jedoch auch per Sprühtrocknung aus der wässrigen Lösung isoliert werden. Es ist mithin ein Vorteil des erfindungsgemäßen Verfahrens, dass es so reines α-Ketocarbonsäurealkalisalz zu genieren im Stande ist, dass direkt nach der Umsalzung eine Sprühtrocknung der Produkte angeschlossen werden kann. Alternatively, however, the alkali salt of the α-ketocarboxylic acid also isolated from the aqueous solution by spray drying become. It is therefore an advantage of the invention Process that it is so pure α-ketocarboxylic acid alkali salt able to be embarrassed is that immediately after the salting spray drying of the products can be connected.
Die Temperatur, bei der die Reaktion durchgeführt wird, soll vorteilhafterweise bei 20°C bis 150°C, bevorzugt 20°C bis 80°C und ganz besonders bevorzugt 40°C bis 60°C liegen. The temperature at which the reaction is carried out should advantageously at 20 ° C to 150 ° C, preferably 20 ° C. up to 80 ° C and very particularly preferably 40 ° C to 60 ° C.
Folgendes Beispiel soll die Erfindung erläutern, sie jedoch
nicht einschränken:
1 mol des Ketosäure Ca-Salzes werden in 200 ml Wasser
suspendiert. Es werden 10,6 g (0,1 mol) festes
Natriumcarbonat zugegeben. Es wird unter Rühren auf 40-60°C
erwärmt und 2 h bei dieser Temperatur gerührt. Nach
Abkühlen auf Raumtemperatur wird das gebildete
Calciumcarbonat abfiltriert.
- a) Das Filtrat, das das Ketosäure-Na-Salz enthält wird auf die Hälfte i. Vak. bei 40-50°C eingedampft. Zur resultierenden Lösung werden unter Rühren 100 ml Aceton gegeben. Das ausgefallene Natriumsalz wird abfiltriert und i. Vak. bei 50-80°C getrocknet.
- b) Das Filtrat wird auf die Hälfte i. Vak. eingedampft. Die resultierende Lösung wird direkt sprühgetrocknet.
1 mol of the keto acid Ca salt are suspended in 200 ml of water. 10.6 g (0.1 mol) of solid sodium carbonate are added. The mixture is heated to 40-60 ° C. with stirring and stirred at this temperature for 2 h. After cooling to room temperature, the calcium carbonate formed is filtered off.
- a) The filtrate, which contains the keto acid Na salt, is divided in half i. Vak. Evaporated at 40-50 ° C. 100 ml of acetone are added to the resulting solution with stirring. The precipitated sodium salt is filtered off and i. Vak. dried at 50-80 ° C.
- b) The filtrate is reduced to half i. Vak. evaporated. The resulting solution is spray dried directly.
Die Isolierausbeuten sind in allen Fällen nahezu
quantitativ.
The isolation yields are almost quantitative in all cases.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002112322 DE10212322A1 (en) | 2002-03-20 | 2002-03-20 | Production of alkali salts of alpha-keto-carboxylic acids, for use e.g. in special diets, involves adding sodium carbonate to an aqueous suspension of the calcium salt and removing calcium carbonate by filtration |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002112322 DE10212322A1 (en) | 2002-03-20 | 2002-03-20 | Production of alkali salts of alpha-keto-carboxylic acids, for use e.g. in special diets, involves adding sodium carbonate to an aqueous suspension of the calcium salt and removing calcium carbonate by filtration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10212322A1 true DE10212322A1 (en) | 2003-10-02 |
Family
ID=27797967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2002112322 Withdrawn DE10212322A1 (en) | 2002-03-20 | 2002-03-20 | Production of alkali salts of alpha-keto-carboxylic acids, for use e.g. in special diets, involves adding sodium carbonate to an aqueous suspension of the calcium salt and removing calcium carbonate by filtration |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE10212322A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2438181A2 (en) * | 2009-06-05 | 2012-04-11 | Evonik Degussa GmbH | A method for the preparation of 2-keto carboxylic acid |
| CN102584570A (en) * | 2012-01-30 | 2012-07-18 | 浙江新和成股份有限公司 | Alpha-ketone-benzol lactamine calcium- hydrate crystal and preparation method thereof |
| CN112062693A (en) * | 2020-09-23 | 2020-12-11 | 上海吉奉生物科技有限公司 | Synthetic method of 2- (9H-fluorene-9-methoxycarbonylamino) -3-methyl-2-butenoic acid |
-
2002
- 2002-03-20 DE DE2002112322 patent/DE10212322A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2438181A2 (en) * | 2009-06-05 | 2012-04-11 | Evonik Degussa GmbH | A method for the preparation of 2-keto carboxylic acid |
| CN102584570A (en) * | 2012-01-30 | 2012-07-18 | 浙江新和成股份有限公司 | Alpha-ketone-benzol lactamine calcium- hydrate crystal and preparation method thereof |
| CN102584570B (en) * | 2012-01-30 | 2015-01-14 | 浙江新和成股份有限公司 | Alpha-ketone-benzol lactamine calcium- hydrate crystal and preparation method thereof |
| CN112062693A (en) * | 2020-09-23 | 2020-12-11 | 上海吉奉生物科技有限公司 | Synthetic method of 2- (9H-fluorene-9-methoxycarbonylamino) -3-methyl-2-butenoic acid |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |