1,11-Undecanediol
[CAS# 765-04-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1,11-Undecanediol
• Synonyms: Undecane-1,11-diol
• Molecular Formula: C₁₁H₂₄O₂
• Molecular Weight: 188.31
• CAS Registry Number: 765-04-8
• EC Number: 212-135-4
• SMILES: C(CCCCCO)CCCCCO

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Boiling point: 318.7±10.0 °C 760 mmHg (Calc.)^*
• Flash point: 146.4±13.6 °C (Calc.)^*
• Index of refraction: 1.459 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

1,11-Undecanediol is a linear aliphatic diol composed of an eleven-carbon hydrocarbon chain with hydroxyl groups located at both terminal carbons. Its molecular formula is C₁₁H₂₄O₂. As an α,ω-diol, it contains two primary alcohol groups separated by a flexible alkyl chain, making it a valuable intermediate in polymer chemistry and specialty chemical synthesis.

The synthesis of 1,11-undecanediol is typically achieved through catalytic hydrogenation of undecanedioic acid or its derivatives such as esters or acid chlorides. Catalysts like Raney nickel or copper chromite are used under elevated temperatures and pressures to reduce carboxyl groups to primary alcohols. Alternative synthetic routes involve multi-step sequences beginning with shorter-chain precursors followed by carbon chain extension.

1,11-Undecanediol’s bifunctional alcohol groups allow its use as a monomer or intermediate in producing polyesters, polyurethanes, and other polymers. The eleven-carbon alkyl chain imparts flexibility, moderate hydrophobicity, and thermal stability to polymer chains. Polymers synthesized using 1,11-undecanediol often exhibit favorable mechanical strength and elasticity, suitable for applications in coatings, adhesives, fibers, and biodegradable plastics.

Besides polymer production, 1,11-undecanediol is employed in manufacturing surfactants, plasticizers, and lubricant additives. Its chemical modification through esterification or etherification leads to amphiphilic molecules useful in detergents, emulsifiers, and personal care products. The combination of hydrophilic hydroxyl groups and hydrophobic alkyl chain facilitates interactions with both polar and nonpolar phases.

Physically, 1,11-undecanediol is generally a colorless to pale yellow liquid or solid depending on purity and temperature. It has limited water solubility but dissolves well in organic solvents such as alcohols, ethers, and hydrocarbons. The compound is chemically stable under normal storage conditions but may react with strong oxidizing agents or undergo hydrolysis under acidic or basic environments.

Toxicological evaluations indicate low acute toxicity and good biodegradability, supporting its use in environmentally friendly chemical processes. It can also be produced from renewable feedstocks, aligning with sustainable chemistry practices.

In summary, 1,11-undecanediol is a bifunctional diol featuring terminal hydroxyl groups on an eleven-carbon alkyl chain. Its chemical properties and structural features make it an important intermediate for polymer synthesis and specialty chemical applications.

References

2023. Synthesis of covalent organic pillars as molecular nanotubes with precise length, diameter and chirality. Nature Synthesis, 2(2).
DOI: 10.1038/s44160-022-00235-w

2022. Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth. Chemistry of Natural Compounds, 58(3).
DOI: 10.1007/s10600-022-03668-z

1999. 1,11-Undecanediol. Acta Crystallographica Section C Crystal Structure Communications, 55(5).
DOI: 10.1107/s0108270198018253