DE591822C - Process for the production of gluconophosphoric acid esters - Google Patents
Process for the production of gluconophosphoric acid estersInfo
- Publication number
- DE591822C DE591822C DESCH95203D DESC095203D DE591822C DE 591822 C DE591822 C DE 591822C DE SCH95203 D DESCH95203 D DE SCH95203D DE SC095203 D DESC095203 D DE SC095203D DE 591822 C DE591822 C DE 591822C
- Authority
- DE
- Germany
- Prior art keywords
- gluconophosphoric
- acid
- production
- gluconic acid
- acid esters
- 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
- 239000002253 acid Substances 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 13
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 11
- 239000000174 gluconic acid Substances 0.000 claims description 11
- 235000012208 gluconic acid Nutrition 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- -1 alkaline earth metal salts Chemical class 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims 1
- 230000026731 phosphorylation Effects 0.000 claims 1
- 238000006366 phosphorylation reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
- C07F9/096—Compounds containing the structure P(=O)-O-C(=X)- (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Dairy Products (AREA)
Description
Verfahren zur Herstellung von Gluconphosphorsäureestern Bisher ist die Einführung des Phosphorsäureesters in die Gluconsäure nur dadurch gelungen, daß man bei Gegenwart säurebindender Substanzen Phosphoroxychlorid auf Gluconsäure bzw. gluconsauren Kalk einwirken ließ. Dieses Verfahren ist technisch deshalb nicht rationell, weil bei seiner Durchführung der Gluconphosphorsäureester vermischt mit Chlorcalcium erhalten wird, das nur außerordentlich schwierig und niemals vollständig von dem eigentlichen Reaktionsprodukt, dem Calciumsalz der Gluconphosphorsäureester, abzutrennen ist.Process for the preparation of gluconophosphoric acid esters So far is the introduction of the phosphoric acid ester into gluconic acid only succeeded that in the presence of acid-binding substances phosphorus oxychloride on gluconic acid or lime gluconic acid allowed to act. This process is therefore not technical Rational, because when it is carried out, the gluconophosphoric acid ester is mixed with it Calcium chloride is obtained, which is extremely difficult and never complete of the actual reaction product, the calcium salt of the gluconophosphoric acid ester, is to be separated.
So ist beispielsweise in der Patentschrift 247 8o9 bei der Herstellung der Gluconphosphorsäureester angegeben, daß man die Entfernung des Chlorcalciums durch mehrfaches Lösen in Wasser und Wiederausfällen mit Alkohol durchführt; in dem Beispiel ist eine 5- bis 6malige Wiederholung der Operation vorgesehen. Bei dem hohen Preis des Alkohols ist ein: solches Verfahren selbstverständlich für die Herstellung der Verbindung in größerem Umfang viel zu teuer.For example, in patent specification 247 8o9 during manufacture the gluconophosphoric acid ester indicated that the removal of calcium chloride carried out by repeated dissolving in water and reprecipitation with alcohol; in The example provides for the operation to be repeated 5 to 6 times. at the high price of alcohol is a: such a procedure taken for granted Much too expensive to make the connection on a large scale.
Demgegenüber wurde gefunden, daß man das Calciumsalz oder andere Erdalkalisalze der Gluconphosphorsäureester in außerordentlich einfacher Weise und völlig frei von Chloriden durch Umsetzung des gluconsauren Kalks oder anderer Erdalkalisalze der Gluconsäure. bzw. der freien Gluconsäure mit den Alkylestern der Phosphorsäure erhalten kann. Beispiel i qo Teile gluconsaurer Talk werden unter Zusatz etwa der gleichen Menge Calciumcarbonat mit etwas mehr als der berechneten Menge organischer Ester der Phosphorsäure (25 g des Reaktionsproduktes von Äther mit Phosphorpentoxyd) vermischt und sodann durch gründliches Verreiben und nachfolgendes Erwärmen zur Reaktion gebracht. Nach Vollendung der Reaktion, die etwa 5 Stunden beansprucht, wird mit ausgekochtem Wasser aufgenommen und durch mehrstündiges Rühren vollständige Neutralisation des Reaktionsproduktes herbeigeführt. Sollte die verwendete Menge Cälciumcarbonat nicht ausreichen, so wird Kalkmilch zugesetzt, so daß die Reaktionsmischung schließlich gerade auf Phenolphthalein anspricht. Nun wird kurz aufgekocht, 2q. Stunden stehengelassen und sodann abfiltriert. Die erhaltene blanke Lauge wird im Vakuum: zur Trockne verdampft. Die Verbindung zeigt alsdann einen Gehalt von etwa 20,5 °/o P2 O5. Die Ausbeute beträgt 6o Teile eines weißen feinen Pulvers, das sich in Wasser spielend leicht und ohne jede Trübung auflöst. Die Lösungen können sterilisiert werden.In contrast, it has been found that the calcium salt or other alkaline earth metal salts of gluconophosphoric acid esters can be obtained in an extremely simple manner and completely free of chlorides by reacting the gluconic acid lime or other alkaline earth metal salts of gluconic acid. or the free gluconic acid can be obtained with the alkyl esters of phosphoric acid. Example i qo parts of gluconic acid talc are mixed with the addition of about the same amount of calcium carbonate with slightly more than the calculated amount of organic esters of phosphoric acid (25 g of the reaction product of ether with phosphorus pentoxide) and then caused to react by thorough trituration and subsequent heating. After completion of the reaction, which takes about 5 hours, it is taken up with boiled water and complete neutralization of the reaction product is brought about by stirring for several hours. If the amount of calcium carbonate used is insufficient, milk of lime is added so that the reaction mixture finally responds to phenolphthalein. Now it is briefly boiled, 2q. Left to stand for hours and then filtered off. The bare lye obtained is evaporated to dryness in vacuo. The compound then shows a content of about 20.5 % P2 O5. The yield is 60 parts of a white, fine powder which dissolves easily in water and without any cloudiness. The solutions can be sterilized.
Beispiel a zo Teile Gluconsäure werden mit 15 Teilen Äthylmetaphosphat 48 Stundenerhitzt. Nach Beendigung der Reaktion wird mit Wasser aufgenommen und mit Kalkmilch alkalisch gemacht. Die weitere Aufarbeitung- erfolgt wie im Beispiel r.Example a zo parts of gluconic acid are heated with 15 parts of ethyl metaphosphate for 48 hours. When the reaction has ended, it is taken up with water and made alkaline with milk of lime. The further work-up takes place as in example r.
Beispiel 3 r kg kristallisierte, pulverisierte Gluconsäure wird mit 1,5 kg Metaphosphorsäureäthylester gut vermischt und unter öfterem Umrühren 48 Stunden auf dem Wasserbad erwärmt. Die gelbe Masse wird nach dem Erkalten in Wasser gelöst und mit Kalkmilch alkalisch gemacht. Dann werden etwa zo 1 Wasser zugegeben, zum Kochen erhitzt und die Lösung vom Rückstand getrennt. In die Lösung leitet man CO, ein, trennt vom Calciumcarbonat und dampft die Lösung, falls notwendig, nach Entfärben mit Kohle im Vakuum zur Trockne.EXAMPLE 3 R kg of crystallized, pulverized gluconic acid is mixed well with 1.5 kg of ethyl metaphosphorate and heated on a water bath for 48 hours with frequent stirring. After cooling, the yellow mass is dissolved in water and made alkaline with milk of lime. About zo 1 water is then added, the mixture is heated to the boil and the solution is separated from the residue. CO 2 is passed into the solution, separated from the calcium carbonate and, if necessary, the solution is evaporated to dryness after decolorization with charcoal in a vacuum.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH95203D DE591822C (en) | 1931-08-27 | 1931-08-27 | Process for the production of gluconophosphoric acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH95203D DE591822C (en) | 1931-08-27 | 1931-08-27 | Process for the production of gluconophosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE591822C true DE591822C (en) | 1934-01-27 |
Family
ID=7445572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH95203D Expired DE591822C (en) | 1931-08-27 | 1931-08-27 | Process for the production of gluconophosphoric acid esters |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE591822C (en) |
-
1931
- 1931-08-27 DE DESCH95203D patent/DE591822C/en not_active Expired
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