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Hexadecanedioic acid
[CAS# 505-54-4]

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Identification
ClassificationChemical reagent >> Organic reagent >> Fatty acid
NameHexadecanedioic acid
SynonymsThapsic acid
Molecular StructureCAS # 505-54-4, Hexadecanedioic acid
Molecular FormulaC16H30O4
Molecular Weight286.41
CAS Registry Number505-54-4
EC Number208-013-5
SMILESC(CCCCCCCC(=O)O)CCCCCCC(=O)O
Properties
Density1.0±0.1 g/cm3, Calc.*
Melting point126 °C
Index of Refraction1.475, Calc.*
Boiling Point457.5±18.0 °C (760 mmHg), Calc.*
Flash Point244.6±17.7 °C, Calc.*
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol   GHS07 Warning  Details
Risk StatementsH315-H319-H335  Details
Safety StatementsP261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
SDSAvailable
up Discovery and Applications
Hexadecanedioic acid, commonly known as palmitic acid, is a dicarboxylic acid with the chemical formula C16H30O4. This compound belongs to the family of long-chain fatty acids and is recognized for its significance in various biological and industrial applications. The discovery of hexadecanedioic acid can be traced back to the early 20th century, during a period of extensive research into fatty acids and their derivatives, which were primarily derived from natural sources such as animal fats and vegetable oils.

Hexadecanedioic acid is synthesized through various methods, including the oxidation of fatty acids, especially palmitic acid. The production process typically involves the oxidation of fatty acids in the presence of oxidizing agents, resulting in the formation of dicarboxylic acids. Its structure consists of a straight-chain hydrocarbon backbone with two carboxylic acid functional groups at each end, making it a symmetrical dicarboxylic acid.

One of the primary applications of hexadecanedioic acid is in the production of polymers and polyamides. Due to its two carboxylic acid groups, hexadecanedioic acid can undergo condensation reactions to form polyamides, which are essential materials in the manufacture of fibers, plastics, and coatings. The unique properties imparted by hexadecanedioic acid, such as increased thermal stability and mechanical strength, make it a valuable component in engineering plastics and high-performance materials.

In addition to its role in polymer chemistry, hexadecanedioic acid is used as a building block in the synthesis of surfactants and detergents. Its amphiphilic nature, characterized by a hydrophilic carboxylic acid group and a hydrophobic hydrocarbon chain, enables it to function effectively in reducing surface tension, making it an important ingredient in cleaning products and personal care formulations. This property enhances the effectiveness of detergents, emulsifiers, and wetting agents, contributing to their ability to remove dirt and oil from surfaces.

Hexadecanedioic acid has also gained attention in the field of biochemistry and nutrition. Research has shown that dicarboxylic acids like hexadecanedioic acid can play a role in cellular metabolism and lipid biosynthesis. Additionally, studies indicate potential health benefits associated with dietary intake of long-chain fatty acids, including anti-inflammatory and cardioprotective effects. As a result, hexadecanedioic acid and its derivatives are being explored for their potential roles in functional foods and dietary supplements aimed at promoting health.

Moreover, hexadecanedioic acid has applications in the field of cosmetics and personal care products. Its moisturizing properties make it an appealing ingredient in formulations designed for skin and hair care. The compound’s ability to enhance product stability and texture has led to its incorporation into a variety of cosmetic formulations, including creams, lotions, and conditioners.

Recent advancements in the synthesis and application of hexadecanedioic acid emphasize its versatility and importance in various industries. Ongoing research continues to explore its potential applications in bioengineering, where its properties may be leveraged for the development of biodegradable materials and sustainable products.

In summary, hexadecanedioic acid is a significant compound with a rich history and diverse applications in polymers, surfactants, nutrition, and cosmetics. Its discovery has paved the way for advancements in material science and biochemistry, underscoring its importance in both industrial and health-related fields.

References

2023. 1,12-Dodecanediol-Based Polyesters Derived from Aliphatic Diacids with Even Carbons: Synthesis and Characterization. Journal of Polymers and the Environment, 31(6).
DOI: 10.1007/s10924-023-02884-0
Market Analysis Reports
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