Chemical of the Week: CITRIC ACID Systematic Name: 2-hydroxypropane-1,2,3-tricarboxylic acid (IUPAC Name) Common Name: citric acid,

hydrogen citrate Chemical Formula: C6H8O7 Molecular Structure:

Legend: red- oxygen Structural Formula Ball and Stick Model white- hydrogen black- carbon Imagery/Picture:

* Citric acid is a natural acid found in fruits such as lemons, limes, peaches, plums, grapefruit and oranges* Classification: organic compound, specifically carboxylic Properties: Physical properties: At room temperature, citric acid is a white crystalline powder. It has a density of 1.665 g/cm3(1.5g/cm3 for monohydrate It melts at 153 C, and boils at 175 C

Has a solubility of 73 g/100 ml (20 C)

Chemical Properties: Citric acid shares the properties of other carboxylic acid Has a pH of 2.2 (0.1 N sol) It is a slightly stronger acid than typical carboxylic acid Will corrode copper, zinc, aluminum and their alloys It is stable under ordinary conditions

Sources/Synthesis: The discovery of citric acid has been credited to the 8th century alchemist Jabir Ibn Hayyan (Geber). Medieval scholars in Europe were aware of the acidic nature of lemon and lime juices. 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 1890 based on the Italian citrus fruit industry. Citric acid can be extracted from the juice of citrus fruits by adding calcium oxide (lime) to form calcium citrate, an insoluble precipitate that can be collected by filtration; the citric acid can be recovered from its calcium salt by adding sulfuric acid. Citric acid is obtained also by fermentation of glucose with the aid of the mold Aspergillus niger Citric acid exists in greater than trace amounts in a variety of fruits and vegetables, most notably citrus fruits. 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 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: Industrial: Air-cured tobacco smoke is often alkaline, giving harsh and irritating flavors. Citric acid and other components are added to balance the flavors. Citric acid is also used in cigarette paper to control the burn rate. This ensures the tobacco and paper burn at the same rate.

Citric acid is added to concrete formulations to retard the set rate and reduce the amount of water required. In the retarding the set rate, the Citrate interferes with the hydration of Portland cement. In its role as a water reducer, citrate acts as a dispersants, reducing the viscosity of the cement slurry so less water is needed to make a workable mixture.

In the paint industry citric acid is used to retard the setting of titanium dioxide, the most common pigment used in paints and other coatings.

Citric acid is added to the pulp slurry prior to bleaching to control paper staining by sequestering metal ions.

Citric acid can be used in food coloring to balance the pH level of a normally basic dye. It is used as an odorless alternative to white vinegar for home dyeing with acid dyes.

Citric acid can be used as a lower-odor stop bath as part of the process for developing photographic film. Photographic developers are alkaline, so a mild acid is used to neutralize and stop their action quickly, but commonly used acetic acid leaves a strong vinegar odor in the darkroom. Medical/Food:

Citric acid is used as one of the active ingredients in the production of antiviral tissues. Citric acid is widely used as a flavoring and stabilizing agent in pharmaceutical preparations. It is used in liquid preparations to enhance fruit flavors and to impart a desirable tart taste that helps mask medicinal flavors.

Citric acid help maintain stability of the active ingredients by buffering aqueous solutions, sequestering trace metals, and assisting in the dispersion of suspensions.

Citric acid in syrups, elixirs, of suspensions and solutions is considered a well established market.

The largest use of citric acid in the pharmaceutical industry is for the effervescent effect it produces when combine with bicarbonates or carbonates in antacids and dentrifices. Effervescence, besides improving palatability, can greatly improve the solubility of coconstituents.

Citric acid in the form of calcium citrate is used as a dietary calcium supplement. Studies have shown that calcium citrate is more bio-available than calcium carbonate.

Citric acid used in jams and jellies to provide tartness and to control the product pH for optimum gelation. Household:

Citric Acid is used to chelate copper in formulations used to kill algae in reservoirs and natural waters. The citric acid chelates the copper, then slowly releases it resulting in extended time of effectiveness.

Citric acid is the active ingredient in some bathroom and kitchen cleaning solutions. A solution with a 6% concentration of citric acid will remove hard water stains from glass without scrubbing.

Citric acid is used in liqued hard surface (floor). Citrate acts as a scale-dissolver, buffer and as an anti-redeposition agent.

In bilge cleaning, citric acid is used for rust removal.

Hazards: Human 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. Causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath. Causes irritation to the gastrointestinal tract. Symptoms may include nausea, vomiting and diarrhea. Extremely large oral dosages may produce gastrointestinal disturbances. Calcium deficiency in blood may result in severe cases of ingestion. Chronic or heavy acute ingestion may cause tooth enamel erosion. Environmental: As with most organic solids, fire is possible at elevated temperatures or by contact with an ignition source.

References: 1. Citric Acid. Wikipedia. Online. Accessed on February 25, 2012. http://en.wikipedia.org/wiki/Citric_acid 2. Citric Acid. Material Safety Sheet Data. Online. Accessed on February 25, 2012. http://www.hvchemical.com/msds/ciac.htm 3. Citric Acid. APAC Chemical Corporation. Online. Accessed on February 25, 2012. http://www.apacchemical.com/CitricAcid.htm#TOP 4. Citric Acid. Online. Accessed on February 25, 2012. http://www.raysahelian.com/citric.html 5. Citric Acid Photos. Online. Accessed on February 26, 2012. http://www.solarnavigator.net/solar_cola/citric_acid.htm