1,14-Tetradecanediol
[CAS# 19812-64-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1,14-Tetradecanediol
• Synonyms: Tetradecane-1,14-diol
• Molecular Formula: C₁₄H₃₀O₂
• Molecular Weight: 230.39
• CAS Registry Number: 19812-64-7
• EC Number: 243-341-2
• SMILES: C(CCCCCCCO)CCCCCCO

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Melting point: 85 - 90 °C (Expl.)
• Boiling point: 356.1±10.0 °C 760 mmHg (Calc.)^*
• Flash point: 158.7±13.6 °C (Calc.)^*
• Index of refraction: 1.462 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Discovery and Applications

1,14-Tetradecanediol is a linear aliphatic diol consisting of a fourteen-carbon saturated hydrocarbon chain with hydroxyl groups attached to both terminal carbons, giving it the molecular formula C₁₄H₃₀O₂. As an α,ω-diol, it possesses two primary alcohol functionalities separated by a long methylene chain. This compound is part of the class of long-chain diols widely used as intermediates in polymer synthesis, surfactant production, and materials science.

The synthesis of 1,14-tetradecanediol is generally achieved by catalytic hydrogenation of the corresponding dicarboxylic acid, tetradecanedioic acid, or its esters. Commonly employed catalysts include Raney nickel or copper chromite under elevated temperature and pressure, facilitating the reduction of carboxyl groups to primary alcohols. Alternative synthetic routes involve hydride reductions or multi-step sequences starting from shorter-chain precursors with carbon chain extension.

Due to its bifunctional nature and long hydrophobic chain, 1,14-tetradecanediol is an important building block in the preparation of polyesters and polyurethanes. In polyester synthesis, it reacts with dicarboxylic acids to form linear or cross-linked polymers exhibiting enhanced flexibility, hydrophobicity, and thermal stability. The long methylene spacer between hydroxyl groups reduces crystallinity and influences the mechanical properties of the resulting materials. Similarly, in polyurethane production, it functions as a chain extender or soft segment, improving elasticity and chemical resistance.

1,14-Tetradecanediol is also employed in the synthesis of surfactants and emulsifiers. Chemical modification, such as esterification or ethoxylation, transforms the diol into amphiphilic molecules useful for stabilizing emulsions, detergents, and personal care products. Its long hydrophobic chain combined with polar end groups enables effective interaction with both aqueous and nonaqueous phases.

In materials chemistry, the diol is utilized for surface modification and functionalization. The two terminal hydroxyl groups facilitate covalent bonding to various substrates, enabling the design of self-assembled monolayers, polymer brushes, and nanostructured coatings. The hydrophobic alkyl chain influences surface wettability and molecular packing, important for applications in adhesives, lubricants, and protective films.

Physically, 1,14-tetradecanediol is typically a white crystalline solid with a melting point reflective of its long carbon chain. It exhibits limited solubility in water but dissolves readily in organic solvents such as alcohols, ethers, and hydrocarbons. The compound is chemically stable under normal laboratory conditions but can be sensitive to strong oxidants or acids.

Toxicological evaluations indicate low acute toxicity and good biodegradability, making 1,14-tetradecanediol suitable for applications aligned with green chemistry and sustainability goals. It can be produced from bio-based feedstocks, including fatty acid derivatives from renewable oils, supporting environmentally friendly chemical manufacturing.

In summary, 1,14-tetradecanediol is a valuable bifunctional intermediate with versatile applications in polymer synthesis, surfactant production, and materials engineering. Its combination of long hydrophobic chain and reactive hydroxyl termini offers chemical adaptability and functional utility across diverse industrial sectors.

References

2023. Synthesis and Characterization of Novel Hydrolytically Degradable Polyesters. Journal of Wuhan University of Technology-Mater. Sci. Ed., 38(4).
DOI: 10.1007/s11595-023-2720-6

1999. 1,14-Tetradecanediol. Acta Crystallographica Section C Crystal Structure Communications, 55(10).
DOI: 10.1107/s0108270199008112

2003. Enzymatic synthesis of multi-component copolymers and their structural characterization. Molecular Diversity, 7(2-4).
DOI: 10.1023/b:modi.0000006820.04426.97