However, when a chelate complex is formed using all three carboxylate groups, the chelate rings have 7 and 8 members, which are generally less stable thermodynamically than smaller chelate rings. Consequently, it forms complexes even with alkali metal cations. The stability constants for the formation of these complexes are quite large because of the chelate effect. The citrate ion forms complexes with metallic cations. The pH of fruit juices from citrus fruits like oranges and lemons depends on the citric acid concentration, with a higher concentration of citric acid resulting in a lower pH.Īcid salts of citric acid can be prepared by careful adjustment of the pH before crystallizing the compound. On the other hand, the pH of a 1 mM solution of citric acid will be about 3.2. Tables compiled for biochemical studies are available. The SSC 20X hybridization buffer is an example in common use. In biological systems around pH 7, the two species present are the citrate ion and mono-hydrogen citrate ion. The speciation diagram shows that solutions of citric acid are buffer solutions between about pH 2 and pH 8. The pK a of the hydroxyl group has been found, by means of 13C NMR spectroscopy, to be 14.4. ![]() It decomposes with loss of carbon dioxide above about 175 ☌.Ĭitric acid is a tribasic acid, with pK a values, extrapolated to zero ionic strength, of 3.128, 4.761, and 6.396 at 25 ☌. Citric acid also dissolves in absolute (anhydrous) ethanol (76 parts of citric acid per 100 parts of ethanol) at 15 ☌. ![]() The monohydrate can be converted to the anhydrous form at about 78 ☌. The anhydrous form crystallizes from hot water, while the monohydrate forms when citric acid is crystallized from cold water. Speciation diagram for a 10-millimolar solution of citric acidĬitric acid can be obtained as an anhydrous (water-free) form or as a monohydrate. More than 50% was used as an acidity regulator in beverages, some 20% in other food applications, 20% for detergent applications, and 10% for applications other than food, such as cosmetics, pharmaceuticals, and in the chemical industry. More than 50% of this volume was produced in China. Global production was in excess of 2,000,000 tons in 2018. In 1977, a patent was granted to Lever Brothers for the chemical synthesis of citric acid starting either from aconitic or isocitrate/alloisocitrate calcium salts under high pressure conditions this produced citric acid in near quantitative conversion under what appeared to be a reverse, non-enzymatic Krebs cycle reaction. After the mold is filtered out of the resulting solution, citric acid is isolated by precipitating it with calcium hydroxide to yield calcium citrate salt, from which citric acid is regenerated by treatment with sulfuric acid, as in the direct extraction from citrus fruit juice. The source of sugar is corn steep liquor, molasses, hydrolyzed corn starch, or other inexpensive, sugary solution. ![]() niger are fed on a sucrose or glucose-containing medium to produce citric acid. In this production technique, which is still the major industrial route to citric acid used today, cultures of A. In 1917, American food chemist James Currie discovered certain strains of the mold Aspergillus niger could be efficient citric acid producers, and the pharmaceutical company Pfizer began industrial-level production using this technique two years later, followed by Citrique Belge in 1929. However, microbial production of citric acid did not become industrially important until World War I disrupted Italian citrus exports. Wehmer discovered Penicillium mold could produce citric acid from sugar. Industrial-scale citric acid production first began in 1890 based on the Italian citrus fruit industry, where the juice was treated with hydrated lime ( calcium hydroxide) to precipitate calcium citrate, which was isolated and converted back to the acid using diluted sulfuric acid. The concentrations of citric acid in citrus fruits range from 0.005 mol/L for oranges and grapefruits to 0.30 mol/L in lemons and limes these values vary within species depending upon the cultivar and the circumstances in which the fruit was grown.Ĭitric acid was first isolated in 1784 by the chemist Carl Wilhelm Scheele, who crystallized it from lemon juice. Lemons and limes have particularly high concentrations of the acid it can constitute as much as 8% of the dry weight of these fruits (about 47 g/L in the juices ). Lemons, oranges, limes, and other citrus fruits possess high concentrations of citric acidĬitric acid exists in a variety of fruits and vegetables, most notably citrus fruits.
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