2-Dodecyloxypropanol
[CAS 9064-14-6]

Identification

• Classification: Organic raw materials >> Alcohols, phenols, phenolic compounds and derivatives
• Name: 2-Dodecyloxypropanol
• Synonyms: 2-dodecoxypropan-1-ol
• Molecular Formula: C₁₅H₃₂O₂
• Molecular Weight: 244.41
• CAS Registry Number: 9064-14-6
• EC Number: 689-976-2
• SMILES: CCCCCCCCCCCCOC(C)CO

Safety Data

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

2-Dodecyloxypropanol is a nonionic surfactant-like alcohol ether consisting of a three-carbon propanol backbone substituted with a long hydrophobic dodecyl (C₁₂) alkoxy chain. Its structure combines a hydrophilic hydroxyl group with a lipophilic alkyl ether chain, giving the molecule amphiphilic properties that are commonly associated with surfactant behavior and interfacial activity.

The molecular structure consists of a propanol unit in which one hydroxyl group remains free, while another position is etherified with a dodecyl group through an oxygen linkage (–O–C₁₂H₂₅). This arrangement creates a distinct polarity gradient within the molecule: the hydroxyl group can participate in hydrogen bonding with water or other polar species, while the long hydrocarbon chain provides strong hydrophobic interactions. As a result, 2-dodecyloxypropanol can associate with both aqueous and organic phases.

Compounds of this type are typically obtained through alkylation reactions involving propylene oxide or glycerol derivatives and long-chain alcohols. One common synthetic route involves the nucleophilic opening of an epoxide intermediate by dodecanol under acidic or basic catalysis, followed by selective functionalization to yield the mono-ether alcohol. Reaction conditions are chosen to control regioselectivity and minimize formation of di- or tri-substituted byproducts.

Historically, etherified glycerol and propanol derivatives have been studied as part of broader research into nonionic surfactants and emulsifiers. The development of such compounds expanded significantly during the 20th century with the growth of detergent chemistry and industrial formulation science. Researchers sought molecules that could stabilize emulsions without carrying a permanent ionic charge, leading to widespread investigation of alkyl ether alcohols and polyol derivatives.

2-Dodecyloxypropanol is primarily used in applications where interfacial activity and moderate polarity are required. It can function as a wetting agent, emulsifier, or solubilizing additive in formulations that combine hydrophobic and hydrophilic components. In industrial and laboratory settings, such compounds are often incorporated into mixtures designed for coatings, cleaning agents, or dispersion systems where control of surface tension is important.

In addition to surfactant-related uses, ether alcohols of this type are of interest as intermediates in organic synthesis. The hydroxyl group allows further chemical modification, such as esterification or oxidation, enabling the preparation of more complex derivatives. The hydrophobic chain length can also be varied to tune physical properties such as solubility, melting point, and interfacial behavior.

From a physicochemical perspective, the balance between hydrophilicity and hydrophobicity in 2-dodecyloxypropanol influences its aggregation behavior in solution. At sufficient concentrations, molecules of this type may form micelle-like assemblies or associate at interfaces between polar and nonpolar phases. This property underlies many of its functional roles in formulation chemistry.

Overall, 2-dodecyloxypropanol is a structurally simple but functionally versatile ether alcohol. Its combination of a hydrophilic hydroxyl group and a long hydrophobic alkyl chain gives it amphiphilic characteristics that are useful in emulsification, solubilization, and interfacial modification applications. Its development reflects broader advances in surfactant chemistry focused on designing molecules with controlled polarity and functional versatility.

References

Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118