Dicarboxylic acids

Dicarboxylic acids
Dicarboxylic_acid_structure.png
General structure of a dicarboxylic acid
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Properties
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References

Introduction

Dicarboxylic acids are organic compounds that contain two carboxyl functional groups (−COOH). They are a subset of the broader class of carboxylic acids, which are characterized by the presence of at least one carboxyl group. Dicarboxylic acids are important in various biological and industrial processes.

Structure and Properties

Dicarboxylic acids have the general formula HOOC-(CH₂)ₙ-COOH, where n can vary, leading to different dicarboxylic acids. The presence of two carboxyl groups influences their chemical properties, such as acidity and solubility.

Acidity

The acidity of dicarboxylic acids is influenced by the distance between the two carboxyl groups. The closer the groups, the stronger the acid, due to the inductive effect and hydrogen bonding. For example, oxalic acid (n=0) is a stronger acid than adipic acid (n=4).

Solubility

Dicarboxylic acids are generally more soluble in water than their monocarboxylic counterparts due to the presence of two polar carboxyl groups. However, solubility decreases with increasing chain length.

Biological Significance

Dicarboxylic acids play crucial roles in metabolism. They are intermediates in the citric acid cycle, which is essential for energy production in aerobic respiration.

Examples in Metabolism

• Oxaloacetic acid - An intermediate in the citric acid cycle, it is involved in the conversion of pyruvate to phosphoenolpyruvate in gluconeogenesis.
• Succinic acid - Another intermediate in the citric acid cycle, it is involved in the conversion of succinyl-CoA to fumarate.

Industrial Applications

Dicarboxylic acids are used in the production of polymers, plasticizers, and lubricants.

Polymer Production

• Adipic acid - Used in the production of nylon 6,6, a widely used synthetic polymer.
• Terephthalic acid - Used in the production of polyethylene terephthalate (PET), a common plastic used in bottles and textiles.

Other Uses

• Sebacic acid - Used in the production of nylon 6,10 and as a plasticizer.
• Azelaic acid - Used in the production of cosmetics and as a treatment for acne.

List of Common Dicarboxylic Acids

• Oxalic acid (C₂H₂O₄)
• Malonic acid (C₃H₄O₄)
• Succinic acid (C₄H₆O₄)
• Glutaric acid (C₅H₈O₄)
• Adipic acid (C₆H₁₀O₄)
• Pimelic acid (C₇H₁₂O₄)
• Suberic acid (C₈H₁₄O₄)
• Azelaic acid (C₉H₁₆O₄)
• Sebacic acid (C₁₀H₁₈O₄)

Conclusion

Dicarboxylic acids are versatile compounds with significant roles in both biological systems and industrial applications. Their unique properties, derived from the presence of two carboxyl groups, make them valuable in various chemical processes.