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Stearyl alcohol
Stearyl alcohol
Stearyl alcohol
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from Wikipedia
Stearyl alcohol[1]
Simplified structural formula
Simplified structural formula
Names
Preferred IUPAC name
Octadecan-1-ol
Other names
1-octadecanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.652 Edit this at Wikidata
UNII
  • InChI=1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3 checkY
    Key: GLDOVTGHNKAZLK-UHFFFAOYSA-N checkY
  • InChI=1/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3
    Key: GLDOVTGHNKAZLK-UHFFFAOYAZ
  • OCCCCCCCCCCCCCCCCCC
Properties
C18H38O
Molar mass 270.49 g/mol
Appearance White solid
Density 0.812 g/cm3
Melting point 59.4 to 59.8 °C (138.9 to 139.6 °F; 332.5 to 332.9 K)
Boiling point 210 °C (410 °F; 483 K) at 15 mmHg (2.0 kPa)
1.1×10−3 mg/L
Hazards
Flash point 185 °C (365 °F; 458 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form of white granules or flakes, which are insoluble in water. It has a wide range of uses as an ingredient in lubricants, resins, perfumes, and cosmetics. It is used as an emollient, emulsifier, and thickener in ointments, and is widely used as a hair coating in shampoos and hair conditioners. Stearyl heptanoate, the ester of stearyl alcohol and heptanoic acid (enanthic acid), is found in most cosmetic eyeliners. Stearyl alcohol has also found application as an evaporation suppressing monolayer when applied to the surface of water.[2]

Stearyl alcohol is prepared from stearic acid or certain fats by the process of catalytic hydrogenation. It has low toxicity.[3]

References

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Stearyl alcohol

View on Grokipedia
from Grokipedia
Stearyl alcohol, also known as 1-octadecanol or octadecan-1-ol (CAS 112-92-5), is a straight-chain, saturated with the chemical formula C₁₈H₃₈O and a molecular weight of 270.5 g/mol. It appears as a white, waxy solid at and is derived from natural sources such as or through reduction processes. This compound is insoluble in but highly soluble in organic solvents like , , and , making it valuable in formulations requiring emulsification and stabilization. Stearyl alcohol is widely used as an emollient, emulsifier, and thickener in and , as well as in pharmaceuticals and industrial applications. It has low and is generally regarded as safe for use, though environmental impacts are considered in regulations.

Properties

Physical properties

Stearyl alcohol, also known as 1-octadecanol, is a straight-chain saturated with the molecular formula C18H38O and the CH3(CH2)16CH2OH. It appears as a white, waxy solid in the form of hard pieces, flakes, or granules, exhibiting a mild, characteristic fatty . The compound undergoes a from solid to liquid at a ranging from 56 to 60 °C, with precise literature values reported between 59.4 and 59.8 °C. Its is approximately 336 °C at , though it distills at around 210 °C under reduced pressure (10–15 mmHg). The of stearyl alcohol is about 0.81 g/cm³ when measured in the liquid state near 60 °C. Stearyl alcohol demonstrates low solubility in water, approximately 1.1 × 10−3 mg/L at 25 °C, attributable to its long hydrophobic hydrocarbon chain. In contrast, it is readily soluble in organic solvents such as ethanol, ether, benzene, acetone, chloroform, and vegetable oils. Additional physical characteristics include a refractive index of approximately 1.438 at 60 °C and a flash point exceeding 170 °C (closed cup). These properties render stearyl alcohol stable and suitable for handling in solid or molten forms under typical laboratory and industrial conditions.

Chemical properties

Stearyl alcohol, also known as 1-octadecanol, is classified as a saturated characterized by a long, unbranched 18-carbon chain with a hydroxyl group (-OH) attached to the terminal (C-1) carbon. This structure enables typical reactivity associated with aliphatic alcohols, including the formation of hydrogen bonds due to the polar -OH group and susceptibility to esterification reactions where the hydroxyl acts as a . Under ambient conditions, stearyl alcohol demonstrates high stability and remains largely non-reactive toward acids and alkalis, resisting common in unsaturated compounds. However, it can undergo oxidation in the presence of strong oxidizing agents, first forming an intermediate (octadecanal) and further proceeding to the corresponding , stearic acid (octadecanoic acid). Additionally, under acidic conditions and elevated temperatures, it participates in dehydration reactions, eliminating water to yield alkenes such as octadecene. The molecule's amphiphilic nature arises from the polar hydroxyl head group and the non-polar aliphatic tail, resulting in a of 20.2 Ų and a high (XLogP3 of 8.4), which allows it to adsorb at oil-water interfaces and reduce interfacial . This behavior promotes emulsification by lowering the energy barrier for droplet formation and coalescence prevention in biphasic systems, though stearyl alcohol typically serves as a co-emulsifier rather than a standalone . The pKa of the hydroxyl group is approximately 15.2, reflecting its weak acidity and limited proton donation capacity in neutral or basic environments. In terms of compatibility, stearyl alcohol readily forms esters with carboxylic acids through acid-catalyzed processes like Fischer esterification, yielding compounds such as stearyl stearate, and can be converted to ethers using the Williamson synthesis, involving of the alcohol followed by reaction with an . These reactions highlight its versatility in synthetic chemistry while maintaining overall chemical inertness in standard storage conditions.

Production

Natural sources

Stearyl alcohol occurs naturally as a component of various animal fats, particularly in and oils, including from the head cavity, where it forms part of the mixtures alongside other fatty alcohols like . In these , stearyl alcohol contributes to the overall composition of long-chain alcohols derived from the of esters, historically recognized as a key natural source before synthetic production dominated. It is also found in smaller amounts in plant-derived materials, as a in like () and in algal species, underscoring its broad biological distribution. Historically, extraction from these natural sources involved of animal fats or plant waxes using to hydrolyze esters into free fatty acids and alcohols, followed by acidification and to isolate the stearyl alcohol fraction; this method was prevalent in the 19th and early 20th centuries prior to the rise of petrochemical alternatives. In biological systems, stearyl alcohol functions as a in lipid assemblies, contributing to formation that provides protective barriers against environmental stresses like and invasion in plants and algae, while in animals, it supports specialized structures such as those in oils for and thermal regulation.

Industrial synthesis

Stearyl alcohol is primarily produced industrially through the catalytic hydrogenation of stearic acid (C17_{17}H35_{35}COOH), a process that converts the carboxylic acid group to an alcohol under high temperature and pressure conditions. This method employs copper chromite (Adkins-type Cu-Cr catalysts) or nickel-based catalysts to achieve high selectivity, typically operating at temperatures of 200–300°C and pressures of 50–200 atm in a continuous flow reactor system. The reaction proceeds via hydrodeoxygenation, where hydrogen gas reduces the acid to the corresponding alcohol, yielding stearyl alcohol with greater than 95% purity directly from the reactor effluent. Today, the primary feedstock for is vegetable oils such as and . Alternative synthetic routes include the reduction of methyl stearate esters, which are first derived from via esterification with . These esters can be reduced using sodium or aluminum hydride in laboratory settings, though industrial applications favor catalytic of the esters with or catalysts under similar high-pressure conditions to produce stearyl alcohol. Another pathway involves the Ziegler process, where undergoes oligomerization with triethylaluminum to form aluminum alkyls, followed by controlled oxidation to alcohols and subsequent , yielding straight-chain even-numbered alcohols like stearyl alcohol. This route provides a fully synthetic alternative independent of natural feedstocks. Following synthesis, the crude product undergoes purification primarily via to remove unreacted , shorter-chain byproducts such as palmitic alcohol (C16_{16}), and other impurities. This step operates under reduced pressure (typically 1–10 mmHg) to lower the and prevent , achieving separation based on differences in volatility and resulting in high-purity stearyl alcohol suitable for commercial use. The industrial production of stearyl alcohol shifted dramatically from natural sources after the , driven by the decline in availability due to and international conservation laws, such as the International Whaling Commission's regulations that curtailed commercial . By the 1980s, synthetic methods had fully replaced whale-derived feedstocks, with global production relying entirely on vegetable oils, animal fats, or routes to meet demand. Typical industrial yields for these processes range from 90–98%, reflecting efficient catalyst performance and minimal side reactions.

Uses

Cosmetics and personal care

Stearyl alcohol serves as a primary emulsifier and co-emulsifier in oil-in-water emulsions for creams and lotions, where it stabilizes formulations to prevent phase separation and enhance product consistency. Reported use concentrations range from less than 0.1% to over 50%, though commonly under 25%. As a viscosity builder, it contributes to thicker, more luxurious textures in these products by increasing the overall rheology without compromising spreadability. Its amphiphilic nature allows it to bridge oil and water phases effectively, supporting stable emulsions common in personal care formulations. In specific beauty and hygiene products, stearyl alcohol is incorporated into shampoos at 0.5–2% to act as a booster, improving lather stability and creaminess during use. In conditioners, it provides slip and detangling benefits by the shaft, reducing and enhancing manageability. For lip balms, it functions as an emollient, delivering a smooth application and protective layer on the lips. These applications leverage its ability to integrate seamlessly into diverse product matrices. Key benefits include its non-comedogenic profile, with a comedogenic rating of 2, making it suitable for acne-prone without pore clogging. It forms an occlusive barrier that promotes retention by reducing , while avoiding a greasy feel due to its lightweight emolliency. This enhances spreadability in many emulsified , improving through even distribution. Stearyl alcohol exhibits strong compatibility when paired with , creating synergistic thickening effects in blended forms like cetearyl alcohol for optimized in emulsions. Historically, it has been used in cold creams since to provide emollient and stabilizing properties in early moisturizing formulations. Concentration guidelines typically range from 1–5% in leave-on products like lotions and creams, and up to 10% in rinse-off items such as shampoos, aligning with safety assessments for cosmetic use.

Industrial and other applications

Stearyl alcohol finds extensive use in industrial sectors beyond personal care, leveraging its waxy texture and emollient properties to enhance product performance in processes. In lubricants and antifoams, it is incorporated into fluids to reduce and improve efficiency, while in detergents, it functions as a to control foam formation during cleaning operations. Within the , stearyl alcohol serves as a key in ointments and suppositories, where it can constitute up to 20% of the formulation to provide for the base and facilitate controlled drug release. As a , stearyl alcohol holds (GRAS) status and is approved for multipurpose applications, including as a component in flavors and a in confections, with usage limited to less than 0.5% to ensure safety and functionality. In other applications, it acts as a retarder in formulations to prevent excessive absorption and maintain material integrity, and as a softener in finishing processes to reduce and enhance fabric . As of 2023, global stearyl alcohol production exceeded 400,000 tons for chemical grade alone, contributing significantly to the market, estimated at around 4 million tons in 2025. The stearyl alcohol market was valued at approximately USD 7.7 billion in 2024.

Safety and regulation

Health and toxicity

Stearyl alcohol exhibits low acute toxicity. The oral LD50 in rats exceeds 5 g/kg, indicating minimal risk from ingestion. Dermal LD50 values in rabbits are greater than 3 g/kg, further supporting its low toxicity profile via skin exposure. It causes minimal eye and skin irritation, with Draize scores below 1 for skin (0.4–1.5/4) and low ocular scores (maximum 5/110, resolving within days) in rabbit studies. Chronic exposure studies show no evidence of carcinogenicity; stearyl alcohol is unclassified by the International Agency for Research on Cancer (IARC). It also demonstrates no in animal studies, including dietary exposures up to 1% with no adverse effects observed. Allergic reactions to stearyl alcohol are rare, with incidence around 0.5% in clinical patch tests involving over 3,700 subjects. It is not considered a sensitizer based on assays and repeat insult patch tests (HRIPT), where no was induced. In vivo, stearyl alcohol is rapidly metabolized in the liver, first oxidized to and then undergoing beta-oxidation to shorter-chain fatty acids for energy production or elimination. to this efficient and its long carbon chain, it does not bioaccumulate in tissues. There is no specific (PEL) established by the (OSHA) for stearyl alcohol. However, the Cosmetic Ingredient Review (CIR) Expert Panel has deemed it safe for cosmetic use at concentrations up to 25%, based on the assessment.

Environmental and regulatory aspects

Stearyl alcohol is considered inherently biodegradable in environmental compartments, with degradation rates of 43–69% within 28 days under aerobic conditions as per Guideline 301B and 301D tests, primarily through microbial beta-oxidation pathways that break down the fatty alcohol chain into and . Its low aquatic toxicity profile supports minimal ecological risk, with LC50 values greater than 0.4 mg/L for fish species such as ( mykiss), indicating it does not pose acute hazards to aquatic organisms at environmentally relevant concentrations. Upon environmental release, stearyl alcohol exhibits minimal persistence, with a of less than 10 days—often as short as 5.7 hours in surface waters via photolysis and —preventing long-term accumulation in or aquatic systems. Despite a high (log Kₒₓ of 7.19–8.22), it shows low bioaccumulation potential, with a (BCF) of 56 in , attributed to rapid metabolic transformation rather than buildup in tissues. Regulatory frameworks classify stearyl alcohol as non-hazardous for environmental purposes. It is registered under the European Union's REACH regulation (EC 1907/2006) with no classification for environmental hazards, reflecting its low persistence and toxicity. In the United States, the FDA has affirmed its Generally Recognized as Safe (GRAS) status for use in food as a texturizer at levels up to 10%, with no objections raised. The Cosmetic Ingredient Review (CIR) Expert Panel has deemed it safe for use in cosmetics at concentrations up to 25%, with no concerns for environmental release from rinse-off products. However, it may be restricted or banned under certain eco-labeling schemes, such as the EU Ecolabel, if derived from non-sustainable (e.g., non-renewable petroleum) sources rather than certified vegetable feedstocks. Sustainability efforts in stearyl alcohol production have shifted toward vegetable-derived routes, such as of from palm or oils, which significantly reduce the compared to historical petroleum-based synthesis via processes. In the , global production and import volumes are monitored under the Toxic Substances Control Act (TSCA), where it holds active status as a low-priority substance for further risk evaluation. For waste management, stearyl alcohol-containing wastes are recommended for disposal via in systems or at controlled facilities, leveraging its inherent biodegradability to minimize reliance. It poses no , as it is not listed under Regulation (EC) 1005/2009 on substances that deplete the .

References

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