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1-Hexanol

1-Hexanol, also known as hexan-1-ol or hexyl alcohol, is a straight-chain primary alcohol with the molecular formula C₆H₁₄O (or C₆H₁₃OH), consisting of a six-carbon chain (hexane) substituted by a hydroxy group at the terminal position.^[1]^[2] It is classified as a fatty alcohol and occurs naturally as a plant metabolite with antibacterial properties.^[1]^[3] This compound appears as a clear, colorless liquid at room temperature, with a melting point of -44.6°C and a boiling point of 157°C.^[1] It has limited solubility in water (5,900 mg/L at 25°C) but is miscible with many organic solvents such as ethanol, acetone, and chloroform.^[1] Chemically, 1-hexanol is flammable (flash point 63°C) and can react with strong oxidizing agents, while it degrades relatively quickly in the environment under aerobic conditions (half-life approximately 1.3 days in air).^[1]^[4] 1-Hexanol finds wide industrial application as a solvent in paints, printing inks, textiles, and resistant coatings, as well as a flotation agent in mineral processing. It serves as an intermediate in the synthesis of plasticizers, lubricants, surfactants, and fragrances, and can be dehydrated to produce 1-hexene for polymer production.^[1]^[5] Additionally, it is used in pharmaceuticals, food flavoring, air care products, and as a lubricant additive, though its production often involves hydroformylation of pentenes followed by hydrogenation.^[1]^[2] From a safety perspective, 1-hexanol is harmful if swallowed or absorbed through the skin (oral LD50 in rats: 720 mg/kg), causes serious eye irritation, and is toxic to aquatic life, necessitating careful handling to avoid ignition sources due to its combustibility.^[1]^[6]

Chemical Identity and Properties

Molecular Structure and Nomenclature

1-Hexanol is a primary alcohol featuring a linear six-carbon chain with a hydroxyl group attached to the terminal carbon. Its condensed structural formula is \ce{CH3(CH2)5OH}, equivalently written as \ce{C6H13OH}, where the unbranched alkane chain derives from hexane and the -OH group is positioned at carbon 1.^[1] The molecular formula of 1-hexanol is \ce{C6H14O}, and its molar mass is 102.17 g/mol.^[1] The International Union of Pure and Applied Chemistry (IUPAC) designates it as hexan-1-ol, specifying the location of the functional group on the parent hexane chain.^[1] Alternative names include n-hexanol, hexyl alcohol, and 1-hexyl alcohol, reflecting its common usage in chemical literature and industry.^[1] This compound is the straight-chain isomer among several hexanol variants, differing from secondary alcohols like 2-hexanol (\ce{CH3CH(OH)(CH2)3CH3}), where the hydroxyl group attaches to a non-terminal carbon, or branched forms such as 2-methyl-1-pentanol.^[7]^[8] The linear primary structure of 1-hexanol distinguishes it in nomenclature and reactivity contexts within the family of C₆ alcohols.^[1]

Physical Characteristics

1-Hexanol is a clear, colorless liquid at room temperature, exhibiting a mild, fatty odor.^[1] This physical state persists under standard conditions, with the compound remaining liquid due to its relatively low melting point of -44.6 °C.^[1] Its boiling point is 157 °C at 760 mm Hg, indicating moderate volatility compared to shorter-chain alcohols.^[1] The density of 1-hexanol is 0.82 g/cm³ at 20 °C, making it less dense than water and prone to floating on aqueous surfaces.^[9] It has limited solubility in water, approximately 5.9 g/L at 20-25 °C, but is miscible with common organic solvents such as ethanol and diethyl ether.^[1] The vapor pressure is 0.928 mm Hg at 25 °C, and the flash point ranges from 59-63 °C (closed cup), highlighting its potential for vapor formation and flammability under elevated temperatures.^[1] Additional physicochemical parameters include a log Kow value of 2.03, reflecting moderate lipophilicity, and a Henry's Law constant of 1.71 × 10⁻⁵ atm-m³/mol, which suggests low tendency to partition into the gas phase from water.^[1]

Chemical Reactivity

As a primary alcohol, 1-hexanol exhibits characteristic reactivity centered on its hydroxyl (-OH) group, which can undergo substitution, oxidation, and elimination reactions under appropriate conditions.^[1] The molecule is relatively stable under ambient conditions, showing no significant decomposition at room temperature and pressure, but it becomes reactive in the presence of strong oxidants, acids, or bases that can protonate or abstract the hydroxyl group.^[4] This stability allows for safe handling in standard laboratory settings, though incompatible materials like alkali metals or strong reducing agents can lead to vigorous reactions producing flammable hydrogen gas.^[10] Oxidation of 1-hexanol proceeds stepwise: mild conditions yield the aldehyde hexanal (CH₃(CH₂)₄CHO), while stronger oxidants further convert it to the carboxylic acid hexanoic acid (CH₃(CH₂)₄COOH). For instance, treatment with potassium permanganate (KMnO₄) in acidic or neutral media directly affords hexanoic acid, as the primary alcohol is fully oxidized to the carboxylic acid derivative:

\ce{CH3(CH2)5OH ->[KMnO4] CH3(CH2)4COOH}

This reaction highlights the susceptibility of primary alcohols to complete oxidation, contrasting with secondary alcohols that stop at ketones.^[11] Esterification occurs readily with carboxylic acids in the presence of an acid catalyst, forming hexyl esters such as hexyl acetate when reacted with acetic acid; this equilibrium reaction releases water and is a key transformation for synthesizing flavor compounds.^[12] Dehydration under acidic conditions, typically with sulfuric acid at elevated temperatures (around 140–180 °C), eliminates water to produce 1-hexene (CH₃(CH₂)₃CH=CH₂) via an E1 mechanism, though isomerization to 2-hexene can occur depending on the catalyst.^[13] Halogenation involves nucleophilic substitution with hydrogen halides (HX, where X = Cl, Br, or I), converting 1-hexanol to the corresponding 1-halohexane, such as 1-chlorohexane (CH₃(CH₂)₅Cl), via an SN2 pathway facilitated by the primary carbon. This reaction requires concentrated HX and often heat, with zinc chloride as a catalyst to improve yields for chlorination.^[14] Overall, these reactions underscore 1-hexanol's versatility as a building block in organic synthesis, with reactivity modulated by reaction conditions to favor specific products.^[15]

Production Methods

Industrial Synthesis

The primary industrial synthesis of 1-hexanol employs the Ziegler process, also known as the Alfol process, which involves the oligomerization of ethylene using triethylaluminum as a catalyst to form trialkylaluminum compounds, followed by oxidation to aluminum alkoxides, hydrolysis to the corresponding alcohols, and fractional distillation to isolate 1-hexanol from the mixture of linear primary alcohols (C6-C12). This multi-stage process begins with the production of triethylaluminum from aluminum powder, hydrogen, and ethylene under controlled conditions (approximately 100°C and 2.5 MPa), followed by chain growth oligomerization in a flow reactor at around 120°C and 10-14 MPa ethylene pressure, yielding an exothermic reaction that builds carbon chains. The subsequent oxidation step uses dry air to convert the trialkylaluminum to alkoxides with high selectivity (85-91%), minimizing byproducts like aldehydes and esters, while hydrolysis with water produces the alcohol phase and aluminum hydroxide; final distillation achieves purities exceeding 98.5% for 1-hexanol, with water content below 1000 ppm.^[16]^[17] An alternative industrial route is the hydroformylation (oxo) process, where 1-pentene reacts with synthesis gas (CO/H₂) in the presence of a rhodium or cobalt catalyst to form hexanal, which is then hydrogenated to 1-hexanol, often using phosphine-modified catalysts to favor linear products over branched isomers. This method typically operates under moderate pressures (10-30 MPa) and temperatures (100-150°C), with the hydroformylation step achieving high conversion rates of the olefin feedstock derived from petroleum refining. The process is integrated into larger oxo-alcohol plants, where the hydrogenation follows immediately to yield the alcohol product suitable for downstream uses.^[18] Developed in the mid-20th century by Karl Ziegler as part of efforts to produce higher straight-chain alcohols from ethylene, these methods enable large-scale output, with global 1-hexanol production reaching approximately 200,000 metric tons annually as of 2020, serving primarily as a precursor for plasticizer esters and surfactants.^[17]^[19]

Alternative Preparations

One common laboratory method for preparing 1-hexanol involves the reduction of hexanal, an aldehyde with the formula CH₃(CH₂)₄CHO, using sodium borohydride (NaBH₄) as the reducing agent. This selective hydride transfer reduces the carbonyl group to a primary alcohol without affecting other functional groups, typically conducted in protic solvents like methanol or ethanol at room temperature, yielding 1-hexanol in high efficiency (often >90%). ^[20] The reaction proceeds via nucleophilic addition of hydride to the carbonyl carbon, followed by protonation. Catalytic hydrogenation provides another effective route for reducing hexanal to 1-hexanol, particularly suitable for larger-scale preparations. Using sulfided Ni-Mo catalysts supported on γ-Al₂O₃ under hydrogen pressure (e.g., 50-100 bar at 150-200°C), hexanal is converted to 1-hexanol with selectivities exceeding 95%, minimizing over-reduction to hydrocarbons. ^[21] This method leverages heterogeneous catalysis for efficient hydrogen transfer, contrasting with stoichiometric reductants like NaBH₄. A multi-step alternative synthesis utilizes aldol condensation followed by reduction, starting with n-butyraldehyde and acetaldehyde. The crossed aldol reaction forms 3-hydroxyhexanal as the initial β-hydroxy aldehyde intermediate, which undergoes dehydration to (E)-2-hexenal under acidic or basic conditions. Subsequent hydrogenation of the α,β-unsaturated aldehyde yields hexanal, and final reduction (e.g., via NaBH₄ or catalytic methods) affords 1-hexanol. This chain-extension approach is represented by:

\text{CH}_3(\text{CH}_2)_2\text{CHO} + \text{CH}_3\text{CHO} \rightarrow \text{intermediate (3-hydroxyhexanal)} \rightarrow \text{CH}_3(\text{CH}_2)_5\text{OH}

after dehydration, hydrogenation, and reduction steps. ^[22] While conceptually useful for building linear chains, this route often suffers from side products due to self-condensation of the aldehydes. From natural sources, 1-hexanol can be obtained on a small scale by reducing caproic acid (hexanoic acid, CH₃(CH₂)₄COOH), which is derivable from fermentation or lipid hydrolysis in plants like coconut oil. Lithium aluminum hydride (LiAlH₄) in ether, followed by aqueous workup, reduces the carboxylic acid to 1-hexanol with near-quantitative yields, though this requires two equivalents of hydride per molecule. Hydrolysis of naturally occurring esters, such as those in essential oils, can liberate 1-hexanol directly via saponification with base, but these methods are not scalable for commercial production due to low concentrations and purification challenges. Emerging alternative preparations include bio-based methods using microbial fermentation. For example, engineered strains of bacteria like Clostridium carboxidivorans can produce 1-hexanol from syngas (CO/H₂) or biomass-derived sugars through metabolic pathways extending from ethanol or butanol synthesis. These processes are still at the research and pilot scale as of 2025, offering potential for sustainable production with reduced carbon footprint.^[23]^[24]

Natural Occurrence

In Plants and Fruits

1-Hexanol is a naturally occurring volatile compound found in the essential oils and aromas of various plants and fruits, including apple, strawberry, tea, and guava.^[1] In guava fruit, it has been identified as a key volatile constituent, with concentrations reaching 3,019.8 µg/kg in mature fruit and 2,378.7 µg/kg in overripe fruit.^[1] These levels contribute to the overall flavor profile of such produce, where 1-hexanol is released alongside other C6 volatiles during fruit ripening and processing.^[25] In plants and fruits, 1-hexanol plays a significant role in sensory characteristics, imparting green, grassy, and fruity notes that evoke the aroma of freshly mown grass and enhance strawberry fragrance.^[26] For instance, it adds to the fresh, green undertones in strawberry and apple scents, complementing other alcohols like (Z)-3-hexen-1-ol in creating herbaceous profiles.^[27] These aroma contributions are particularly prominent in damaged or ripening plant tissues, where 1-hexanol helps define the "green leaf" odor typical of many fruits and vegetables.^[28] The biosynthesis of 1-hexanol in plants primarily derives from fatty acid metabolism through the lipoxygenase (LOX) pathway. Unsaturated fatty acids, such as linoleic acid, undergo peroxidation by LOX enzymes to form hydroperoxy fatty acids, which are then cleaved into aldehydes like hexanal; these can be subsequently reduced to 1-hexanol by alcohol dehydrogenases.^[29] This pathway is widespread in green plant tissues and is activated in response to mechanical damage or developmental cues, linking 1-hexanol production to broader plant stress responses and flavor development.^[30] Vegetation, including fruits like apples, releases 1-hexanol as a volatile emission, with rates varying by environmental conditions and harvest timing. For example, emissions from apples harvested in August-October ranged from 3.8 to 117.6 pico-L/kg-hr across different orchards.^[1] These emissions contribute to the atmospheric profile of plant-derived volatiles, influencing ecological interactions and the sensory quality of fresh produce.^[31]

In Animals and Other Sources

1-Hexanol serves as a component of the alarm pheromones in honey bees (Apis mellifera), contributing to defensive signaling by eliciting attraction and investigative behaviors among colony members during threats.^[32] This alcohol is released from the sting apparatus and other exocrine glands, forming part of a complex blend of over 40 volatile compounds that coordinate alarm responses.^[33] As a fatty alcohol, 1-hexanol occurs naturally in fats, oils, and waxes derived from animal, marine, and other non-plant sources through the breakdown of lipids.^[1] In marine environments, it appears in trace concentrations, such as 2.5–20.2 μg/kg in the tissues of Charybdis feriatus crabs, reflecting its role in lipid profiles of aquatic organisms.^[1] Similarly, it is present at trace levels in beeswax, where it arises from the metabolic processing of fatty acids in bee secretions.^[1] Microbial production of 1-hexanol occurs in certain bacteria, including soil-dwelling species, where it plays a minor role as an antibacterial agent, particularly inhibiting Gram-negative bacteria at vapor concentrations above 150 ppm.^[34]^[35] This volatile compound contributes to microbial defense mechanisms by disrupting bacterial growth without broadly affecting Gram-positive strains.^[35]

Applications

In Fragrances and Flavors

1-Hexanol serves as a key ingredient in perfumery, where it imparts green, leafy, and fresh notes reminiscent of freshly mowed grass and ripening fruit.^[36] Its ethereal, fruity, and slightly oily odor profile enhances floral, herbal, and fruity accords in perfumes, often contributing to compositions featuring lavender, violet, and strawberry nuances.^[37] Additionally, it is incorporated into antiseptic formulations for its mild, pleasant scent that masks harsher chemical odors.^[38] In food flavoring, 1-hexanol enhances fruity aromas, particularly in strawberry and apple products, by adding green, apple-skin, and oily undertones that mimic natural fruit profiles.^[1] It is recognized as generally recognized as safe (GRAS) by the FDA under 21 CFR 172.515 and by FEMA (No. 2567), allowing its use as a synthetic flavoring agent in beverages, ice cream, candies, and baked goods at levels up to 26 ppm in certain applications.^[1] The compound's sensory threshold, with detection as low as 0.007–0.01 ppm and recognition at 0.09 ppm, enables subtle enhancement without overpowering other flavors.^[1] Formulations typically employ 1-hexanol at concentrations of 0.1–1% in fragrance concentrates to leverage its mild, fatty odor for balanced sensory effects, as recommended by IFRA standards.^[36] Derivatives such as hexyl acetate and hexyl butyrate extend its utility, providing brighter, juicier, and green apple-like notes in broader fragrance and flavor applications.^[36] These esters are valued for their sweet, fruity profiles that complement citrus, tropical, and berry compositions in perfumery.^[39]

In Industrial Processes

1-Hexanol serves as a versatile solvent in various industrial applications due to its favorable solubility properties for both polar and non-polar substances. It is commonly employed in the formulation of paints and printing inks, where it aids in dissolving resins and pigments to achieve desired viscosity and flow characteristics. Additionally, 1-hexanol is utilized in extraction processes, such as reactive extractions for separating organic acids from aqueous solutions, leveraging its protic nature to enhance phase separation efficiency.^[40]^[41] It is also used as a flotation agent in mineral processing.^[1] In the production of plasticizers, 1-hexanol acts as a key precursor, particularly in the synthesis of isomeric C6-alcohol mixtures that form esters like phthalates, trimellitates, azelates, and adipates. These plasticizers are essential for softening polyvinyl chloride (PVC) and improving the flexibility and processability of PVC-based materials in applications such as films, coatings, and cables. The compound's straight-chain structure contributes to the stability and performance of these esters in industrial formulations.^[40]^[42] Beyond solvents and plasticizers, 1-hexanol finds niche roles as a defoamer in textile and leather processing, where it suppresses foam formation during dyeing and finishing operations to maintain process efficiency. It also functions as an emulsifier in pharmaceutical manufacturing, facilitating the incorporation of the hexyl group into active ingredients for hypnotics and antiseptics, thereby enhancing their solubility and bioavailability. In the oil and gas sector, it serves as an antifoaming agent in aqueous drilling muds.^[40]^[42] Commercially, 1-hexanol is produced as part of broader higher alcohol streams through processes like the oxo synthesis from pentenes, with global output integrated into high-volume categories exceeding thousands of tons annually. In the United States, it is classified as a high-production-volume (HPV) chemical, with annual production or import exceeding 1 million pounds.^[43]^[44]^[45] Recent research highlights its potential as a sustainable biofuel in diesel engines owing to its high cetane number and energy density.^[46]

Safety and Environmental Considerations

Health and Toxicity

1-Hexanol is classified under the Globally Harmonized System (GHS) as a warning substance due to its acute toxicity and irritant properties. It is harmful if swallowed (H302), harmful in contact with skin (H312), and causes serious eye irritation (H319). ^[6] Additionally, it poses a flammability risk as a liquid with explosive limits in air ranging from 1.2% to 7.7% by volume. ^[47] Primary exposure routes in occupational settings include inhalation of vapors and dermal contact during handling, with ingestion possible through accidental swallowing. The oral LD50 in rats is 720 mg/kg, indicating moderate acute toxicity via this route. ^[6] Dermal LD50 in rabbits is approximately 1,500–2,330 mg/kg, suggesting lower but still notable absorption through the skin. ^[48] ^[47] Acute effects from exposure include skin and eye irritation, with potential for severe eye damage, respiratory tract irritation, nausea, and central nervous system depression if inhaled in high concentrations. ^[6] Chronic exposure to 1-hexanol, as with other organic solvents, may contribute to solvent-induced encephalopathy, characterized by neurobehavioral dysfunction such as memory impairment and reduced cognitive function. First aid measures emphasize immediate action: for eye contact, rinse with water for at least 15 minutes and seek medical attention; for skin contact, wash with soap and water; in cases of inhalation, move to fresh air; and for ingestion, do not induce vomiting but seek professional medical help immediately. ^[6]

Ecological Impact

1-Hexanol enters the environment primarily through industrial effluents and waste streams associated with its production and use in perfumery, plasticizers, solvents, and food additives.^[2] As a volatile organic compound (VOC), it contributes to atmospheric emissions during manufacturing and handling processes.^[1] In environmental compartments, 1-hexanol demonstrates rapid biodegradation, mitigating its persistence. Under aerobic conditions, measured half-lives range from 0.36 to 1.7 days, with biochemical oxygen demand (BOD) reaching 28% to 83.6% over 5 days.^[2] Anaerobic degradation is also efficient, achieving 75% to 83% removal within 7 days at 37°C.^[2] These rates indicate that 1-hexanol is unlikely to accumulate in soil or water due to microbial breakdown. The compound exhibits high mobility in soil, with an organic carbon-water partition coefficient (Koc) of 10.2, suggesting it leaches readily into groundwater.^[2] Bioaccumulation potential is low, as evidenced by a bioconcentration factor (BCF) of 21, calculated using its octanol-water partition coefficient (log Kow) of 2.03; this value points to moderate lipophilicity but limited uptake in organisms.^[2]^[1] 1-Hexanol poses toxicity risks to aquatic ecosystems, with acute effects observed in standard test species. The 96-hour LC50 for fathead minnow (Pimephales promelas) is 97.5 mg/L, and the 24-hour EC50 for water flea (Daphnia magna) is 240 mg/L, classifying it as toxic to aquatic life.^[2] Its moderate log Kow further implies potential for bioaccumulation in lower trophic levels, though rapid degradation limits long-term ecosystem disruption.^[1]

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