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Citric acid

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(Redirected from Citrate)
Properties

General

Name Citric acid

image:citricacidstructure.png

Chemical formula C6H8O7, or alternatively:

CH2(COOH).COH(COOH).CH2(COOH)

Formula weight 192.13 amu
Synonyms 2-hydroxy-1,2,3-propanetricarboxylic acid
CAS number 77-92-9

Phase behavior

Melting point 426 K (153 °C)
Thermal decomposition temperature 448 K (175°C)

Acid-base properties

pKa1 3.15
pKa2 4.77
pKa3 5.19

Solid properties

ΔfH0 -1543.8 kJ/mol
S0 252.1 J/mol·K
Cp 226.5 J/mol·K
Density 1.665 ×103 kg/m3

Safety

Acute effects Skin and eye irritant.
Chronic effects None.

More info

Properties NIST WebBook (http://webbook.nist.gov/cgi/cbook.cgi?ID=C77929&Units=SI)
MSDS Hazardous Chemical Database (http://ull.chemistry.uakron.edu/erd/chemicals1/7/6308.html)

SI units were used where possible. Unless otherwise stated, standard conditions were used.

Disclaimer and references

Citric acid is a weak organic acid found in citrus fruits. It is a good, natural preservative and is also used to add an acidic (sour) taste to foods and soft drinks. In biochemistry, it is important as an intermediate in the citric acid cycle and therefore occurs in the metabolism of almost all living things. It also serves as an environmentally friendly cleaning agent and acts as an antioxidant.

Citric acid exists in a variety of fruits and vegetables, but it is most concentrated in lemons and limes, where it can comprise as much as 8% of the dry weight of the fruit.

Citric acid's chemical formula is C6H8O7 and its structure is shown at right. This structure is reflected in its IUPAC name 2-Hydroxy-1,2,3-propanetricarboxylic acid.

Contents

Properties

The physical properties of citric acid are summarized in the table at right. The acidity of citric acid results from the three carboxy groups COOH which can lose a proton in solution. If this happens, the resulting ion is the citrate ion. Citrates make excellent buffers for controlling the pH of acidic solutions.

Citrate ions form salts called citrates with many metal ions. An important one is calcium citrate or "sour salt", which is commonly used in the preservation and flavoring of food. Additionally, citrates can chelate metal ions, which gives them use as preservatives and water softeners.

At room temperature, citric acid is a white crystalline powder. It can exist either in an anhydrous (water-free) form, or as a monohydrate that contains one water molecule for every molecule of citric acid. The anhydrous form crystallizes from hot water, while the monohydrate forms when citric acid is crystallized from cold water. The monohydrate can be converted to the anhydrous form by heating it above 74°C.

Chemically, citric acid shares the properties of other carboxylic acids. When heated above 175°C, it decomposes through the loss of carbon dioxide and water.

History

The discovery of citric acid has been credited to the 8th century Arab-Yemeni (Iranian-born) alchemist Jabir Ibn Hayyan (Geber). Medieval scholars in Europe were aware of the acidic nature of lemon and lime juices; such knowledge is recorded in the 13th century encyclopedia Speculum Majus (The Great Mirror), compiled by Vincent of Beauvais. Citric acid was first isolated in 1784 by the Swedish chemist Carl Wilhelm Scheele, who crystallized it from lemon juice. Industrial-scale citric acid production began in 1860, based on the Italian citrus fruit industry.

In 1893, C. Wehmer discovered that Penicillium mold could produce citric acid from sugar. However, microbial production of citric acid did not become industrially important until World War I disrupted Italian citrus exports. In 1917, the American food chemist James Currie discovered that certain strains of the mold Aspergillus niger could be efficient citric acid producers, and Pfizer began industrial-level production using this technique two years later.

Production

In this production technique, which is still the major industrial route to citric acid used today, cultures of Aspergillus niger are fed on sucrose to produce citric acid. After the mold is filtered out of the resulting solution, citric acid is isolated by precipitating it with lime (calcium hydroxide) to yield calcium citrate salt, from which citric acid is regenerated by treatment with sulfuric acid.

Alternatively, citric acid is sometimes isolated from the fermentation broth by extraction with a hydrocarbon solution of the organic base trilaurylamine, followed by re-extraction from the organic solution by water.

Uses

Most citric acid is used as a flavoring and preservative in food and beverages, especially soft drinks; it is denoted by E Number E330. Citrate salts of various metals are used to deliver those minerals in a biologically available form in many dietary supplements. The buffering properties of citrates are used to control pH in household cleaners and pharmaceuticals.

Citric acid's ability to chelate metals gives it use in soaps and laundry detergents. By chelating the metals in hard water, it lets these cleaners produce foam and work better without need for water softening. Similarly, citric acid is used to regenerate the ion exchange materials used in water softeners by stripping off the accumulated metal ions as citrate complexes.

It is used in the biotechnology and pharmaceutical industry to passivate high purity process piping in lieu of using nitric acid, since nitric is a hazardous disposal issue once it is used for this purpose, while citric is not.

In the United Kingdom, pharmacies control the sale of Citric acid. Citric acid is a popular buffer used to increase the solubility of street heroin in Scotland. Single-use citric acid sachets have been used as an inducement to get heroin users to exchange their dirty needles for clean needles in an attempt to decrease the spread of AIDS and hepatitis. See the .pdf article here (http://www.drugmisuse.isdscotland.org/eiu/pdfs/citric_acid_full.pdf). Other acidifiers used for brown heroin are ascorbic acid, acetic acid, and lactic acid: in their absence, the drug abuser will often substitute lemon juice or vinegar.

Safety

Citric acid is recognized as safe for use in food by all major national and international food regulatory agencies. It is naturally present in almost all forms of life, and excess citric acid is readily metabolized and eliminated from the body.

Contact with dry citric acid or with concentrated solutions can result in skin and eye irritation, so protective clothing should be worn when handling these materials.de:Zitronensure es:cido ctrico fr:Acide citrique it:Acido citrico nl:Citroenzuur ja:クエン酸 nn:Sitronsyre pl:Kwas cytrynowy pt:cido ctrico ru:Лимонная кислота

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