Sebacic acid
[CAS# 111-20-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Acyclic carboxylic acid
• Name: Sebacic acid
• Synonyms: 1,8-Octanedicarboxylic acid; Decanedioic acid
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.25
• CAS Registry Number: 111-20-6
• EC Number: 203-845-5
• SMILES: C(CCCCC(=O)O)CCCC(=O)O

Properties

• Density: 1.21
• Melting point: 131-134 °C
• Boiling point: 294.4 °C (100 mmHg)
• Flash point: 220 °C
• Water solubility: 1 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Sebacic acid, a dicarboxylic acid with the chemical formula C10H18O4, is a key compound in the field of organic chemistry and materials science. Its discovery can be traced back to the early 19th century when it was first isolated from the fat of the sperm whale by the French chemist Michel Eugène Chevreul in 1818. The name "sebacic" is derived from the Latin word "sebacus," meaning "fat." Over the years, various methods for synthesizing sebacic acid have been developed, including the oxidation of castor oil, which is a renewable resource.

Sebacic acid is most commonly produced through the oxidation of ricinoleic acid, a component of castor oil. This process typically involves the use of oxidizing agents, such as potassium permanganate, to convert ricinoleic acid into sebacic acid. The resulting sebacic acid can be further purified through crystallization, yielding a white crystalline solid that is soluble in alcohol and ether but only slightly soluble in water.

One of the primary applications of sebacic acid is in the production of polyamides, specifically nylon 6,10. The incorporation of sebacic acid into nylon provides enhanced flexibility, durability, and resistance to chemicals and heat compared to other nylon types. This makes nylon 6,10 ideal for use in applications such as automotive parts, textiles, and various consumer goods. The ability to incorporate sebacic acid into polymeric materials has significantly broadened the scope of potential applications, leading to the development of high-performance materials that meet diverse industry needs.

Sebacic acid is also used as a plasticizer in the production of flexible PVC (polyvinyl chloride) products. As a plasticizer, it improves the workability, durability, and softness of PVC, making it suitable for a wide range of applications, including electrical cables, flooring, and medical devices. The addition of sebacic acid as a plasticizer enhances the overall performance of PVC, making it a preferred choice in many industries.

In the field of cosmetics and personal care, sebacic acid is utilized as an emollient and thickening agent in formulations. Its ability to impart a smooth texture to creams and lotions makes it a valuable ingredient in skincare products. Additionally, sebacic acid is used in the production of esters, which serve as fragrances and flavoring agents in the food and cosmetic industries.

Sebacic acid has found applications in the pharmaceutical sector as well, where it is used in the synthesis of various drug compounds. Its role as a building block in organic synthesis allows for the creation of more complex molecules, enhancing the potential for drug development. The versatility of sebacic acid makes it an important compound in medicinal chemistry, particularly in the design of new therapeutic agents.

The growing interest in biodegradable materials has led to the exploration of sebacic acid as a potential building block for bio-based polymers. Research into the use of sebacic acid in the formulation of biodegradable polyesters and polyurethanes aims to create sustainable alternatives to traditional petroleum-based plastics. These bio-based materials could significantly reduce environmental impact while providing the desired mechanical properties for various applications.

Sebacic acid's multifunctional properties and renewable sourcing make it a valuable compound in numerous industries. Ongoing research and development in the fields of materials science, pharmaceuticals, and environmental sustainability continue to uncover new applications and potential for sebacic acid, solidifying its role as a key ingredient in modern chemistry.

References

2024. 10‐hydroxy decanoic acid, trans‐10‐hydroxy‐2‐decanoic acid, and sebacic acid: Source, metabolism, and potential health functionalities and nutraceutical applications. Journal of Food Science.
DOI: 10.1111/1750-3841.17143

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

1947. High Molecular Weight Hydrocarbons. II. Five New Hydrocarbons Derived from Sebacic Acid. Journal of the American Chemical Society.
DOI: 10.1021/ja01199a035