Organic compounds are essential in various industries, including pharmaceuticals, food, and cosmetics. One of the organic compounds that have gained attention in recent years is pimelic acid. Pimelic acid, also known as heptanedioic acid, is a dicarboxylic acid with the chemical formula C7H12O4. It is a white crystalline solid that is soluble in water and ethanol. Pimelic acid is used in the production of nylon, plasticizers, and lubricants. It is also used as a precursor in the synthesis of various chemicals, such as adipic acid, azelaic acid, and 2,5-dimethylhexane-2,5-dicarboxylic acid. In this blog post, SACH BIOTECH will discuss the extraction of pimelic acid, including its properties, sources, and methods of extraction.
Properties of Pimelic Acid
Pimelic acid has a molecular weight of 160.17 g/mol and a melting point of 105-107°C. It is a weak acid with a pKa of 4.44. Pimelic acid is a dibasic acid, which means it has two carboxylic acid groups. It is a non-toxic and non-flammable compound that is stable under normal conditions. Pimelic acid is hygroscopic, which means it can absorb moisture from the air. It is also sensitive to light and can undergo photodegradation.
Sources of Pimelic Acid
Pimelic acid is a naturally occurring compound that can be found in various sources. It is present in the fatty acids of some plants and animals, such as coconut oil, milk, and cheese. Pimelic acid is also produced by some bacteria, such as Pseudomonas aeruginosa and Bacillus subtilis. However, the most common source of pimelic acid is through the chemical synthesis of adipic acid. Adipic acid is a dicarboxylic acid that is widely used in the production of nylon. It is produced by the oxidation of cyclohexane or cyclohexene with nitric acid. Pimelic acid is obtained by the hydrogenation of adipic acid using a catalyst, such as palladium on carbon.
Methods of Extraction
There are several methods of extracting pimelic acid, depending on the source and the intended use of the compound. The most common methods of extraction are chemical synthesis and microbial fermentation.
Chemical Synthesis
Chemical synthesis is the most common method of producing pimelic acid. As mentioned earlier, pimelic acid is obtained by the hydrogenation of adipic acid using a catalyst, such as palladium on carbon. The process involves the reduction of the carboxylic acid groups of adipic acid to form pimelic acid. The reaction is carried out under high pressure and temperature, typically at 100-150°C and 50-100 atm. The yield of pimelic acid depends on the purity of the starting material and the efficiency of the catalyst.
Microbial Fermentation
Microbial fermentation is another method of producing pimelic acid. It involves the use of microorganisms, such as bacteria and fungi, to convert organic substrates into pimelic acid. The process is carried out under controlled conditions, such as temperature, pH, and nutrient supply. The microorganisms produce enzymes that break down the organic substrates into simpler compounds, which are then converted into pimelic acid. The yield of pimelic acid depends on the type of microorganism used, the composition of the substrate, and the fermentation conditions.
Extraction of Pimelic Acid from Coconut Oil
Coconut oil is a rich source of pimelic acid. It contains about 7% pimelic acid, along with other fatty acids, such as lauric acid, myristic acid, and palmitic acid. The extraction of pimelic acid from coconut oil involves several steps, including saponification, acidification, and extraction.
Saponification
Saponification is the process of converting fats and oils into soap and glycerol. In the case of coconut oil, saponification is carried out using sodium hydroxide (NaOH) or potassium hydroxide (KOH). The fatty acids in coconut oil react with NaOH or KOH to form soap and glycerol. The soap is then separated from the glycerol by centrifugation or filtration.
Acidification
Acidification is the process of converting the soap into free fatty acids. In the case of coconut oil, acidification is carried out using hydrochloric acid (HCl) or sulfuric acid (H2SO4). The acid reacts with the soap to form free fatty acids and sodium chloride or potassium chloride. The free fatty acids are then separated from the salt by centrifugation or filtration.
Extraction
Extraction is the process of separating the pimelic acid from the other fatty acids in the coconut oil. In the case of pimelic acid, extraction is carried out using a solvent, such as ethyl acetate or hexane. The solvent is added to the free fatty acids and mixed thoroughly. The mixture is then allowed to settle, and the solvent layer is separated from the fatty acid layer. The solvent layer is then evaporated to obtain the pimelic acid.
Conclusion
Pimelic acid is a valuable organic compound that has various applications in different industries. It is a dicarboxylic acid that is used in the production of nylon, plasticizers, and lubricants. Pimelic acid is obtained through chemical synthesis or microbial fermentation. The extraction of pimelic acid from coconut oil involves saponification, acidification, and extraction. The yield of pimelic acid depends on the purity of the starting material and the efficiency of the extraction method. With the increasing demand for organic compounds, the extraction of pimelic acid is expected to become more important in the future.
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