1,12-Dodecanediol
[CAS# 5675-51-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 1,12-Dodecanediol
• Synonyms: Dodecamethylene glycol; Dodecane-1,12-diol
• Molecular Formula: C₁₂H₂₆O₂
• Molecular Weight: 202.34
• CAS Registry Number: 5675-51-4
• EC Number: 227-133-9
• SMILES: C(CCCCCCO)CCCCCO

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Melting point: 79 - 81 ºC (Expl.)
• Boiling point: 313.3 ºC 760 mmHg (Calc.)^*, 365.5 ºC (Expl.)
• Flash point: 151.1±13.6 ºC (Calc.)^*, 176 ºC (Expl.)
• Index of refraction: 1.46 (Calc.)^*

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

Safety Data

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

Discovory and Applicatios

1,12-Dodecanediol is an aliphatic diol consisting of a twelve-carbon linear hydrocarbon chain with hydroxyl groups attached at both terminal carbons. Its molecular formula is C₁₂H₂₆O₂. As an α,ω-diol, it features two primary alcohol functional groups separated by a flexible hydrocarbon chain, making it an important intermediate in polymer chemistry and specialty chemical synthesis.

The synthesis of 1,12-dodecanediol can be achieved through several methods, including catalytic hydrogenation of dodecanedioic 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 the carboxyl groups to primary alcohols. Other synthetic routes involve multi-step processes starting from shorter-chain precursors, followed by carbon chain extension.

1,12-Dodecanediol’s bifunctional alcohol groups make it a valuable monomer or intermediate in producing polyesters, polyurethanes, and other polymers. The twelve-carbon alkyl spacer contributes flexibility, hydrophobicity, and thermal stability to polymer chains. When incorporated into polyesters, it reacts with dicarboxylic acids to form materials with balanced mechanical strength and elasticity, suitable for fibers, coatings, adhesives, and biodegradable plastics.

Beyond polymer synthesis, 1,12-dodecanediol is used in the manufacture of surfactants, plasticizers, and lubricant additives. Its chemical modifications through esterification or etherification yield amphiphilic molecules useful in detergents, emulsifiers, and personal care products. The balance between hydrophilic hydroxyl groups and hydrophobic alkyl chain enables interactions with both polar and nonpolar environments.

Physically, 1,12-dodecanediol is typically a colorless to pale yellow solid with a melting point influenced by purity and chain length. It is sparingly soluble in water but dissolves well in organic solvents like alcohols, ethers, and hydrocarbons. The compound is chemically stable under normal conditions but may react with strong oxidizing agents or undergo acidic or basic hydrolysis.

Toxicological evaluations indicate low acute toxicity and favorable biodegradability, supporting its use in environmentally friendly chemical manufacturing. It can be produced from renewable feedstocks such as bio-based dicarboxylic acids, aligning with green chemistry principles.

In summary, 1,12-dodecanediol is a versatile bifunctional alcohol widely used in polymer chemistry, specialty chemicals, and materials science. Its structural and chemical properties make it a valuable intermediate for producing polymers and functional materials with diverse industrial applications.

References

2023. 1,12-Dodecanediol-Based Polyesters Derived from Aliphatic Diacids with Even Carbons: Synthesis and Characterization. Journal of Polymers and the Environment, 31(7).
DOI: 10.1007/s10924-023-02884-0

2023. Bio-Based Poly(Butylene succinate-co-dodecylene succinate) Derived from 1,12-Dodecanediol: Synthesis and Characterization. Journal of Polymers and the Environment, 31(8).
DOI: 10.1007/s10924-023-02916-9

2023. Synthesis, thermal and barrier properties of biodegradable aliphatic polycarbonates with different chain lengths. Journal of Thermal Analysis and Calorimetry, 148(14).
DOI: 10.1007/s10973-023-12352-5