1,10-Decanediol
[CAS# 112-47-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 1,10-Decanediol
• Synonyms: Decamethylene glycol
• Molecular Formula: C₁₀H₂₂O₂
• Molecular Weight: 174.28
• CAS Registry Number: 112-47-0
• EC Number: 203-975-2
• SMILES: C(CCCCCO)CCCCO

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*, 1.08 g/mL (Expl.)
• Melting point: 71 - 74 ºC (Expl.)
• Boiling point: 305.4±10.0 ºC 760 mmHg (Calc.)^*, 297 ºC (Expl.)
• Flash point: 141.7±13.6 ºC (Calc.)^*, 152 ºC (Expl.)
• Solubility: water: insoluble (Expl.)
• Index of refraction: 1.458 (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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

1,10-Decanediol is a linear aliphatic diol with the molecular formula C₁₀H₂₂O₂. It consists of a ten-carbon straight chain bearing a hydroxyl group at each terminal carbon, making it a symmetric α,ω-diol. It is also known by the name decamethylene glycol and is part of a broader family of long-chain diols used in the synthesis of polymers, lubricants, and surfactants.

The compound was first synthesized and characterized in the early 20th century as part of systematic studies on aliphatic polyols. Its synthesis typically involves hydrogenation of sebacic acid or sebacoyl derivatives, such as sebacoyl chloride or esters. Catalytic hydrogenation using metal catalysts such as Raney nickel or copper chromite facilitates the reduction of the carboxylic acid groups to primary alcohols, yielding 1,10-decanediol in high purity. Alternatively, it can be obtained by the reduction of esters with lithium aluminum hydride or through the oxidation of terminal alkenes followed by reduction.

1,10-Decanediol is widely used as a monomer in the production of polyesters and polyurethanes. Its symmetrical structure and long hydrocarbon chain contribute to the flexibility, hydrophobicity, and low glass transition temperatures of the resulting polymers. When reacted with dicarboxylic acids, such as terephthalic acid or adipic acid, it forms linear polyesters with applications in thermoplastics, fibers, and biodegradable materials. In polyurethane synthesis, it serves as a chain extender that enhances the mechanical properties and thermal stability of elastomeric materials.

In the field of cosmetics and personal care, 1,10-decanediol is utilized for its antimicrobial properties and its ability to improve skin moisture retention. It has been incorporated into formulations such as creams, lotions, and deodorants, where it contributes both to texture and functional performance. Studies have shown that this diol exhibits inhibitory effects against certain gram-positive bacteria and yeasts, making it a useful ingredient in dermatological applications.

Due to its amphiphilic nature—possessing both hydrophilic hydroxyl groups and a hydrophobic alkyl chain—1,10-decanediol has also found use in surfactant chemistry. It serves as a precursor to nonionic surfactants and emulsifiers, particularly when modified with ethylene oxide or esterified with fatty acids. These derivatives are valued for their low toxicity and biodegradability and are used in detergents, emulsions, and agricultural formulations.

In materials science, 1,10-decanediol has been explored in the modification of surfaces and nanostructures. Its bifunctional nature enables covalent attachment to a variety of substrates, and its long chain helps to control spacing or orientation in self-assembled monolayers and multilayer films. In certain cases, it has been used in the preparation of functionalized nanoparticles or as a linker in supramolecular architectures.

The physical properties of 1,10-decanediol include a high melting point near 75 °C and low volatility. It is a white crystalline solid at room temperature, soluble in alcohols and glycols, but only slightly soluble in water. It is thermally stable under typical processing conditions, which makes it compatible with melt-polymerization and extrusion techniques.

Toxicological evaluations have indicated that 1,10-decanediol has low acute toxicity and is generally regarded as safe for industrial and cosmetic use at typical concentrations. It is biodegradable and considered environmentally benign, aligning with current trends in green chemistry and sustainable materials development.

Overall, 1,10-decanediol is a well-established chemical intermediate and additive with applications across polymer science, personal care, and surface engineering. Its symmetric structure, chemical stability, and functional versatility ensure its continued relevance in both established and emerging areas of industrial chemistry.

References

2020. Synthesis and properties of poly(ethylene terephthalate) modified with a small amount of 1,10-decanediamine and hydrogen bonds. Journal of Materials Science, 56(11).
DOI: 10.1007/s10853-020-05590-7

2019. Synthesis and Properties of Poly(butylene carbonate-co-spirocyclic carbonate). Chemical Research in Chinese Universities, 35(3).
DOI: 10.1007/s40242-019-8355-7

1906. Darstellung des Chlorhydrins, des Oxyds und eines ungesättigten Alkohols aus dem normalen biprimären Dekamethylenglykol (Dekan-1, 10-diol). Monatshefte f�r Chemie und verwandte Teile anderer Wissenschaften.
DOI: 10.1007/bf01527177