1,13-Tridecanediol
[CAS# 13362-52-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1,13-Tridecanediol
• Synonyms: tridecane-1,13-diol
• Molecular Formula: C₁₃H₂₈O₂
• Molecular Weight: 216.36
• CAS Registry Number: 13362-52-2
• SMILES: C(CCCCCCO)CCCCCCO

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 343.9±10.0 ºC 760 mmHg (Calc.)^*
• Flash point: 154.8±13.6 ºC (Calc.)^*
• Index of refraction: 1.461 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H332-H335
• Precautionary Statements: P261-P280-P305+P351+P338

Discovory and Applicatios

1,13-Tridecanediol is a linear aliphatic diol consisting of a thirteen-carbon straight chain with hydroxyl groups attached to both terminal carbons, giving it the molecular formula C₁₃H₂₈O₂. It is classified as an α,ω-diol, characterized by the presence of two primary alcohol functional groups separated by an eleven-carbon methylene chain. This compound is part of a broader class of long-chain diols that are utilized in various chemical and industrial applications due to their bifunctional reactivity and hydrophobic alkyl segment.

The synthesis of 1,13-tridecanediol is commonly achieved by catalytic hydrogenation of the corresponding dicarboxylic acid, tridecanedioic acid, or its derivatives such as esters or acid chlorides. Typical hydrogenation catalysts include Raney nickel or copper chromite under elevated temperature and pressure conditions, enabling the reduction of carboxyl groups to primary alcohols. Alternative synthetic methods include reduction using powerful hydride reagents, though catalytic hydrogenation remains preferred for its scalability and efficiency.

Due to its long alkyl chain and terminal hydroxyl groups, 1,13-tridecanediol serves as an important monomer and intermediate in polymer synthesis. It is employed in the production of polyesters and polyurethanes, where its bifunctionality allows it to act as a chain extender or cross-linker. Incorporation of 1,13-tridecanediol into polymer chains typically imparts increased flexibility, hydrophobicity, and enhanced thermal stability to the resulting materials. The long methylene spacer between reactive groups reduces intermolecular interactions and crystallinity, influencing mechanical and physical properties.

In addition to polymer applications, 1,13-tridecanediol is valuable in the synthesis of specialty chemicals, surfactants, and lubricants. Its amphiphilic nature, with hydrophilic alcohol termini and a hydrophobic alkyl core, allows it to function as a precursor for nonionic surfactants when chemically modified by ethoxylation or esterification. These derivatives exhibit favorable biodegradability and low toxicity, making them suitable for use in detergents, emulsifiers, and personal care products.

The compound also finds use in surface chemistry and materials engineering. Its two hydroxyl groups enable covalent attachment to various substrates, facilitating the formation of self-assembled monolayers, surface coatings, and functionalized nanomaterials. The long alkyl chain provides hydrophobic spacing, influencing surface wettability, adhesion, and molecular organization in multilayer assemblies.

Physically, 1,13-tridecanediol is a solid at ambient temperature with a relatively high melting point reflective of its long carbon chain. It is sparingly soluble in water but soluble in many organic solvents such as alcohols and ethers. The compound exhibits chemical stability under standard storage conditions but can be sensitive to strong oxidizing agents or prolonged exposure to heat.

Toxicological data indicate that 1,13-tridecanediol has low acute toxicity and is generally regarded as safe for industrial applications. It is biodegradable and compatible with environmentally friendly manufacturing processes. These properties contribute to its increasing use as a renewable and sustainable chemical intermediate, especially when derived from bio-based feedstocks.

1,13-Tridecanediol continues to be of interest in both academic research and industrial production due to its multifunctionality, long hydrocarbon chain, and adaptability in chemical modification. Its role as a versatile building block supports the development of advanced polymers, surfactants, and functional materials across a wide range of sectors.

References

2010. Synthesis of omega-hydroxy carboxylic acids and alpha,omega-dimethyl ketones using alpha,omega-diols as alkylating agents. The Journal of Organic Chemistry, 75(3).
DOI: 10.1021/jo9027165

1997. 1,13-Tridecanediol. Acta Crystallographica Section C Crystal Structure Communications, 53(2).
DOI: 10.1107/s010827019601390x

1989. Liquid crystalline polyethers based on conformational isomerism. Polymer Bulletin, 22(5-6).
DOI: 10.1007/bf00718924