Decanoic acidCanadian Journal of Chemistry, 43 6: The limiting conductances have been obtained from the measurements in the usual way. Tren ace veins effect of increasing chain length on mobility is discussed. From a consideration of the experimental and the theoretical values of the slopes of the sodiuj of equivalent conductance against the square root of the concentration, it is concluded that some sort of interaction, possibly a reversible dimerization of anions, occurs, even in sodium decanoate dilute region, and this could account for the lower experimental values of the slope. This phenomenon has been observed with other long chain electrolytes, however, sodium decanoate the hypothesis of dimerization is not sodium decanoate only possible one.
Sodium decanoate | CAS | SCBT - Santa Cruz Biotechnology
Similarly, according to part CFR free fatty acids e. As noted by Dimitrijevic eta! W discloses that medium-chain fatty acids and their metal salts especially capric acid, caprylic acid and their sodium salts are able to induce hematopoiesis.
The sodium salts of capric acid and caprylic acid, in comparison to the respective free acids, possess superior water solubility. Typically, the reaction of an acid with base in an aqueous medium is rapid and straightforward, as long as the acid and base are water-soluble.
The limited water-solubility of medium-chain fatty acids makes the large-scale, high-yield preparation of the metal salts of fatty acids more difficult.
Emulsions and suspensions can form, with excessive frothing and foam if carbon dioxide is a byproduct of the reaction e. At least one free fatty acid of the appropriate length i. The solvent may comprise one or more alcohols. Free fatty acid is reacted with at least one metal salt to produce the metal salt of the medium-chain fatty acid.
The metal salt may comprise a monovalent cation e. Preferred metal fatty acid salts are sodium or potassium caprylate, and sodium or potassium caprate.
Further aspects of the invention will be apparent to a person skilled in the art from the following description and claims, and generalizations thereto. The metal salt products must be conveniently prepared on large scale in high purity and high yield at a reasonable cost.
It has been found surprisingly that, when a concentrated solution of medium-chain fatty acid dissolved in ethanol e. As shown in the following Examples, purification is achieved by filtration and washing with volatile organic solvents. The novel process comprises reacting the precursor free fatty acid, dissolved in a suitable solvent, with the appropriate bicarbonate or carbonate salt.
The process uses a relatively high concentration of free fatty acid as a soluble reactant with a consequently small amount of foam arising from the formation of carbon dioxide. Therefore, the process allows for the convenient large-scale preparation of fatty acid salt products. Medium-chain fatty acids refer to those monocarboxylic fatty adds having carbon chain lengths of 6 caproic add, hexanoic acid , 8 caprylic add, octanoic acid , 10 capric acid, decanoic acid and 12 lauric add, dodecanoic acid.
While even-numbered carbon atom chain lengths, and the preparation of their metal salts, constitute a preferred embodiment of this invention, it is not limited to even-numbered carbon atom chains. Odd- numbered carbon atom chains include 7 carbons heptanoic acid , 9 carbons nonanoic acid and 11 carbons undecanoic acid. A concentration of free fatty add reactant of at least 0.
The solubility of medium-chain fatty acid is typically no more than 1. In particularly preferred embodiments, the metal salt of a medium-chain fatty acid refers to the sodium or potassium salt of capric acid or caprylic acid. Temperatures of less than 50 C are less desirable since they reduce the speed of the reaction and result in a reduced yield of metal salt product relative to free fatty acid reactant.
The following Examples are presented to illustrate the invention but are not intended to limit the invention. The mixture was stirred vigorously for minutes. The clear solution was then diluted with water ml.
Solid sodium bicarbonate g, 2. At the end of the reaction the pH was observed to be neutral. The clear solution was then cooled slowly during 3 hours to 42 C under vigorous stirring. The resulting mixture was diluted with tert-butyl methyl ether 1. The temperature dropped to 30 C. The white precipitate was filtered under suction water aspirator using a polypropylene coarse glass funnel 7 L and the wet solid was air-dried for 1.
The product was broken up into small pieces using a spatula and kept under high vacuum at 20 C for 16 hours. The pure acid sodium salt was isolated as a white solid. Purity of sodium decanoate was assessed by HPLC analysis. The mobile phase is a mixture of 2. The pH of the final solution is adjusted to 8. The decanoate salt peak appears at a retention time of 17 minutes.
A calibration curve was used to calculate the purity of the decanoate salt in the final product. The sodium cation peak appears at a retention time of 4 minutes. A calibration curve was used to calculate the sodium in the decanoate salt in the final product. The mobile phase was prepared by mixing acetonitrile with tetrahydrofuran and water in a ratio of 5: The unreacted capric acid peak appeared at a retention time of 7 minutes.
A calibration curve was used to calculate unreacted capric acid present in the final sodium decanoate salt product. The mixture was stirred vigorously for 5 minutes. The clear solution was then diluted with water 30 ml. Solid calcium carbonate 5. Water 10 ml was added to the reaction each day except the last one. On the last day, excess water ml was added to complete the reaction. The mixture was cooled to 45 C water bath and filtered through a coarse glass funnel.
This gave a white solid which was washed with absolute ethanol 50 ml , tert-butyl methyl ether 2 x 50 ml and air-dried for 2 hours. The solid was then dissolved in boiling methanol 1. The clear filtrate was cooled and concentrated to ml. The white precipitate was filtered under suction water aspirator using a coarse glass funnel 1 L and air-dried for 3 hours. The resulting solid was kept under high vacuum at 20 C for 18 hours.
The pure acid calcium salt was isolated as a snow-white solid. Claims having "comprising" allow the inclusion of other elements to be within the scope of the claim; the invention may also be described by such claims having the transitional phrase "consisting essentially or i. Any of these three transitions can be used to claim the invention. A process for the preparation of metal salts of a medium-chain length monocarboxylic fatty acid comprises reacting the precursor free fatty acid, dissolved in a suitable solvent, with the appropriate metal salt.
The process uses a relatively high concentration of free fatty acid as a soluble reactant and produces metal fatty acid salts at high purity and high yield at a reasonable cost. A method of preparing a metal salt of a medium-chain fatty acid, wherein the method comprises solubilizing at least one free fatty acid in solvent, wherein said free fatty acid has a chain length from six to twelve carbons; and reacting said free fatty acid with at least one metal salt, to produce a metal fatty acid salt.
The method according to claim 1, wherein the solvent comprises an alcohol. The method according to claim 1 or claim 2, wherein the metal salt comprises a monovalent cation or a divalent cation.
The method according to claim 3, wherein the metal salt comprises sodium or potassium. The method according to claim 3, wherein the metal salt comprises calcium or magnesium.
The method according to any one of claims 1 to 5, wherein the free fatty acid is reacted with at least one metal bicarbonate or at least one metal carbonate. The method according to any one of claims 1 to 6, wherein the metal fatty acid salt is sodium or potassium caprylate.
The method according to claim 7, wherein the metal fatty acid salt is sodium caprylate. The method according to any one of claims 1 to 6, wherein the metal fatty acid salt is sodium or potassium caprate. The method according to claim 9, wherein the metal fatty acid salt is sodium caprate. The method according to any one of claims 1 to 10, wherein the concentration of the free fatty acid in solvent is at least 0.
The method according to any one of claims 1 to 11, further comprising recovering the metal fatty acid salt by precipitation and filtration. The method according to any one of claims 1 to 12, further comprising quantifying the purity of the produced metal fatty acid salt by separating product from reactants by High Pressure Liquid Chromatography HPLC.
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