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2-Butoxyethanol


is a colorless, high-boiling liquid with the molecular formula C₆H₁₄O₂ and a mild -like , classified as a glycol that functions as a where one methyl of is substituted by a butoxy group. Its physical properties include a of 171 °C, a of -70 °C, and miscibility with and many organic , enabling its role in dissolving both hydrophilic and hydrophobic substances. Industrially produced via the reaction of with n-butanol, it serves primarily as a versatile in applications such as water-based paints, varnishes, household cleaners, inks, and , where it enhances product stability and efficacy by coupling with oil-dissolving power. However, empirical data from toxicological studies indicate moderate , with inhalation or dermal exposure at high levels causing , reduced , irritation to eyes and , and potential liver and damage, though it lacks evidence of carcinogenicity or mutagenicity in humans. Regulatory bodies have established exposure limits, such as OSHA's permissible exposure level of 50 ppm, to mitigate occupational risks while preserving its industrial utility.

History

Discovery and Early Development

2-Butoxyethanol emerged from early 20th-century advancements in glycol ether synthesis, pioneered by Carbide and Carbon Chemicals Corporation (predecessor to ) as part of efforts to develop superior industrial . The compound, synthesized via the reaction of with n-butanol, followed the 1920s patenting of analogous ethyl cellosolve by Dr. Charles O. Young, which established the foundational process for monoalkyl ether derivatives of . These developments addressed limitations of conventional alcohols, providing a solvent with enhanced solvency for resins, oils, and in lacquers and coatings. Commercialization accelerated in and as demand grew for versatile, high-boiling-point solvents in paints, inks, and cleaning formulations, where 2-butoxyethanol demonstrated superior coupling and penetration properties over or derivatives. By the mid-20th century, industrial production had scaled, reflecting its integration into expanding sectors. U.S. output reached 130 million pounds annually by 1972, underscoring its role in broadening applications beyond traditional options. This growth paralleled the petrochemical boom, with 2-butoxyethanol becoming a key E-series glycol by the .

Properties

Physical Characteristics

2-Butoxyethanol is a colorless with a mild, ether-like . Its molecular is C₆H₁₄O₂. The has a of 171 °C at standard . Its density is 0.90 g/cm³ at 20 °C, making it less dense than . The is approximately 0.8 mmHg at 20 °C, which corresponds to moderate volatility suitable for applications. 2-Butoxyethanol is fully miscible with and most solvents due to its amphiphilic featuring both hydrophobic butyl and hydrophilic ethoxyhydroxy groups.
Physical PropertyValueReference Conditions
Melting Point-75 °CLiterature value
67 °CClosed cup

Chemical Behavior and Solubility

2-Butoxyethanol demonstrates infinite with , forming homogeneous solutions in all proportions due to its polar hydroxyl group facilitating hydrogen bonding. This property distinguishes it from many non-polar ethers, which exhibit limited solubility, and enables its role in aqueous-based formulations. It is also fully miscible with organic solvents such as , , and acetone, enhancing its versatility as a co-solvent. The amphiphilic structure of 2-butoxyethanol, featuring a hydrophobic butyl chain and a hydrophilic hydroxyethoxy moiety, imparts surfactant-like properties that lower interfacial tension between immiscible phases. This dual nature allows it to bridge hydrophilic and hydrophobic substances, promoting stability in mixed solvent systems without forming traditional micelles at low concentrations. Under standard ambient conditions, 2-butoxyethanol remains chemically stable with minimal reactivity, showing no tendency for hazardous decomposition or polymerization. In biological environments, however, it is metabolized primarily through oxidation of the terminal alcohol group to form 2-butoxyacetic acid, reflecting its susceptibility to enzymatic .

Production

Industrial Synthesis Methods

The primary industrial method for synthesizing 2-butoxyethanol is the of anhydrous n-butanol with in the presence of a . This reaction proceeds via nucleophilic attack of the ion derived from n-butanol on the ring of , yielding the desired monoether product under controlled conditions of temperature (typically 120–180°C) and pressure (1–5 ) to ensure high conversion rates exceeding 90%. The process is highly efficient for large-scale operations, with raw material inputs dominated by petrochemical-derived and n-butanol, enabling cost-effective production due to the simplicity and scalability of the reactor systems employed. To optimize selectivity and minimize byproducts, the to n-butanol molar ratio is strictly controlled near 1:1, preventing excessive oligomerization that would form diethylene glycol monobutyl ether (up to 0.2% impurity) or higher analogs. Post-reaction purification involves under vacuum to separate the target compound ( 171.2°C), achieving technical-grade purity >99% while rejecting unreacted alcohols, , and trace glycols. This purification step is critical for downstream applications, as residual byproducts can affect performance, and modern processes incorporate of excess n-butanol to enhance overall and reduce waste. Less commonly, 2-butoxyethanol can be produced via the variant, alkylating or ethylene chlorohydrin with dibutyl sulfate under basic conditions using , though this route generates more inorganic salts and is disadvantaged by lower compared to the dominant . By 1983, U.S. production volumes exceeded 230 million pounds annually, reflecting the method's entrenched role in high-volume glycol .

Applications

Solvents in Coatings and Paints

2-Butoxyethanol functions as a key in protective surface coatings, including spray lacquers, quick-dry lacquers, enamels, varnishes, and paints, where it dissolves resins such as and synthetic polymers to achieve uniform formulations. Typical concentrations range from 1% to 30% by volume in these coatings, depending on the system, with 2–5% common in aqueous formulations to maintain stability and performance. Its high solvency power stems from a balance of hydrophilic and hydrophobic groups, allowing effective dissolution of both water-soluble and components while providing complete in and many solvents at . This enables superior control compared to some alternatives, reducing solution thickness for smoother application and improved flow during brushing or spraying. In quick-dry lacquers and enamels, 2-butoxyethanol's moderate evaporation rate supports enhanced drying characteristics and film leveling, promoting even surface formation without defects like orange peel or sagging. These properties contribute to its preference in industrial coatings for wood finishes and metal surfaces, where empirical testing shows better resin compatibility and application efficiency than faster-evaporating solvents alone.

Cleaning and Household Products

2-Butoxyethanol serves as a key in household and industrial formulations, enabling the dissolution of organic residues such as oils, greases, and dirt that are not readily water-soluble. Its amphiphilic properties allow it to couple hydrophobic soils with aqueous solutions, facilitating emulsification and removal during rinsing. This makes it particularly effective in products like cleaners, all-purpose spray cleaners, liquid soaps, floor strippers, and degreasers, where it enhances against stubborn contaminants. The compound's utility in these applications stems from its ability to dissolve greases and oils at low concentrations, typically sufficient for performance without requiring high dosages that could compromise formulation stability or cost. For instance, it improves the emulsifying action of soaps when incorporated as a mutual for mineral oils, allowing cleaners to handle both water-based and oil-based soils effectively. Historical data indicate its presence in over 430 cleaning products in as of , including general surface cleaners and spot removers, underscoring its widespread adoption in systems. , surveys from reported it in more than 740 products overall, with nearly half designated for household use, reflecting its role in enabling versatile, high-performance cleaners.

Petroleum Industry Uses

In the , 2-butoxyethanol serves primarily as a in fluids and hydraulic fracturing operations, where it reduces to enhance wettability and improve the of additives, thereby facilitating better penetration into formations. This property contributes to by minimizing loss to the formation and stabilizing emulsions in water-based systems. The compound also plays a role in (EOR) techniques, particularly in shale-rich reservoirs, acting as a mutual when combined with diluted to alter rock wettability and mobilize residual oil, with laboratory studies demonstrating increased recovery yields through processes. In pipeline and wellbore , 2-butoxyethanol is incorporated into cleaning compositions to dissolve scales and organic deposits, enabling effective removal without excessive mechanical intervention, as evidenced in formulations targeting FeS accumulation. These applications persist due to demonstrated benefits in yield optimization and , outweighing concerns in controlled settings.

Toxicology

Acute Exposure Effects

Acute inhalation exposure to 2-butoxyethanol vapors primarily causes irritation to the mucous membranes of the eyes, nose, and upper respiratory tract, often accompanied by symptoms such as headache, nausea, dizziness, and a metallic taste in the mouth. Human studies indicate that mild ocular and nasal irritation may occur at concentrations around 25 ppm for short durations (10-120 minutes), while more pronounced effects, including throat irritation and belching, have been reported at levels up to 50 ppm. The odor threshold is detectable at 0.1-0.4 ppm, but sensory irritation thresholds are higher, with a no-observed-adverse-effect level (NOAEL) for discomfort and respiratory irritation established at 20 ppm in controlled human exposures. Recovery from these effects is typically rapid and complete upon cessation of exposure and removal to fresh air. Dermal contact with undiluted 2-butoxyethanol or concentrated solutions results in moderate , characterized by redness, dryness, and potential defatting of the , though it is not a severe sensitizer. Direct ocular causes immediate severe , including , redness, and possible corneal damage, as evidenced by animal data corroborated by case reports. In a documented incident involving seven clerical workers, acute led to severe immediate eye and upper respiratory , presyncope, and , resolving without long-term sequelae after prompt intervention. Hemolytic effects, a hallmark of acute high-dose exposure in rodents (observed at oral doses >100 mg/kg due to the metabolite butoxyacetic acid), are far less pronounced in humans owing to differences in red blood cell sensitivity and faster metabolic clearance of the metabolite. In vitro assessments confirm that human erythrocytes exhibit sub-hemolytic responses to butoxyacetic acid at concentrations that lyse rat cells, and clinical hemolysis remains rare in human acute exposures, even at levels causing systemic symptoms. Erythrocyte osmotic fragility does not significantly alter in humans following controlled inhalation exposures up to 87 ppm for 4 hours.

Chronic and Long-Term Risks

Chronic exposure to 2-butoxyethanol via or dermal routes in occupational settings has not demonstrated conclusive evidence of carcinogenicity in humans, with epidemiological studies showing no increased cancer incidence among exposed workers. , including National Toxicology Program (NTP) experiments at doses up to 250 ppm for two years, reported hemangiosarcomas in male mice and forestomach squamous cell carcinomas, but equivocal hepatocellular adenomas in female rats; however, these findings exhibit limited relevance to humans due to species-specific metabolic differences, such as greater susceptibility to in and absence of a forestomach in humans. The International Agency for Research on Cancer (IARC) classifies 2-butoxyethanol as Group 3 (not classifiable as to carcinogenicity to humans), citing inadequate human data and limited mechanistic concordance with rodent outcomes. High-dose animal models reveal potential liver and effects from repeated , with intermediate-duration studies in s showing increased weights and histopathological changes at airborne concentrations exceeding 100 , often secondary to and metabolite accumulation like butoxyacetic acid. In contrast, human occupational data from controlled environments with indicate minimal incidence of such organ toxicity; for instance, Agency for Toxic Substances and Disease Registry (ATSDR) reviews of worker cohorts exposed below 25 report no consistent liver elevations or renal dysfunction, attributing lower risk to humans' reduced hemolytic sensitivity—human erythrocytes require over threefold higher concentrations for compared to cells. Dose-response analyses confirm a below occupational limits (e.g., ACGIH TLV of 20 ), where no-observed-adverse-effect levels (NOAELs) in translate to margins of exceeding 10-fold for humans after pharmacokinetic adjustments. The Expert Panel's 2025 amended assessment reaffirms the safety of butoxyethanol in at typical low concentrations (up to 5% in products, lower elsewhere), finding insufficient evidence to warrant revised restrictions despite re-examination of animal carcinogenicity data, as human dermal absorption and systemic exposure remain negligible under diluted use conditions. This counters claims of inherent long-term hazard by emphasizing empirical dose-response gaps between exaggerated animal models and real-world dilute applications, with no substantiated reproductive or developmental chronic risks beyond acute thresholds in either species.

Comparative Human and Animal Data

2-Butoxyethanol (2-BE) demonstrates marked differences in , largely attributable to variations in the and handling of its primary , butoxyacetic acid (BAA). In rats and mice, BAA accumulates systemically and exerts direct hemolytic effects on erythrocytes by altering integrity and osmotic fragility, leading to at relatively low doses. Humans, however, exhibit faster conjugation and of BAA via pathways producing and , which substantially attenuates erythrocyte damage and systemic . In vitro assessments of hemolytic potential confirm this disparity: , , and red blood cells undergo rapid when exposed to BAA concentrations as low as 1-2 mM, whereas human erythrocytes require concentrations exceeding 5 mM for comparable effects, with and cells displaying intermediate sensitivity. These findings align with in vivo observations where develop pronounced following oral or inhalation exposures, while non-human like rhesus monkeys tolerate chronic inhalation of 100-210 ppm for 30-90 days without hemolytic changes or respiratory distress. Acute toxicity metrics further illustrate these differences; the oral LD50 in rats is approximately 470-700 mg/kg, eliciting and secondary organ effects, compared to higher thresholds in less sensitive species. No human LD50 data exist due to ethical constraints, but controlled human exposures and pharmacokinetic modeling predict minimal hemolytic risk at occupational levels below 25 ppm, supported by the absence of blood dyscrasias in analogs. Epidemiological data from occupational cohorts exposed dermally or via to 2-BE in industrial settings (e.g., painting, cleaning) show no consistent evidence of or chronic hematological abnormalities, even at airborne concentrations up to 10-20 over years, contrasting sharply with precautionary extrapolations from models that overestimate vulnerability. This underscores the necessity of prioritizing and higher data over rodent-derived endpoints for causal risk evaluation, as metabolic and physiological divergences render direct interspecies scaling unreliable without adjustment.

Environmental Impact

Fate and Degradation

2-Butoxyethanol undergoes primary degradation through aerobic microbial processes in environmental compartments such as and . Under aerobic conditions, it is readily biodegradable, with studies demonstrating substantial breakdown by adapted microbial populations within standard testing periods. The estimated half-life for follows , ranging from 1 to 4 weeks in and environments. In specifically, the biodegradation extends from 14 days to 8 weeks, reflecting variations in microbial activity and substrate availability. Bioaccumulation potential remains low due to its high water (miscible with water) and low (log Kow ≈ 0.83), which limit partitioning into lipid tissues and favor rapid in organisms. This compound does not meet criteria for under regulatory frameworks like those from the . Volatilization contributes minimally to attenuation, as indicated by its low Henry's law constant (≈ 2.4 × 10^{-8} atm-m³/mol), resulting in negligible from moist or dry soils and limited transfer from water to air. occurs slowly or not at all under environmental pH conditions, with no significant direct hydrolytic breakdown reported. Overall, aerobic dominates natural removal, supporting its classification as environmentally attenuating without persistent accumulation.

Ecological Toxicity

2-Butoxyethanol exhibits moderate acute toxicity to aquatic organisms, with 96-hour LC50 values for species such as (Oncorhynchus mykiss) ranging from 560 mg/L to 1,474 mg/L under static test conditions following Test Guideline 203. Similar results have been observed for and , indicating low to moderate sensitivity across primary trophic levels, with no pronounced effects at sublethal concentrations in standard ecotoxicity assays. Environmental monitoring data reveal typical surface and concentrations of 2-butoxyethanol in the per liter (µg/L) range or below, often orders of magnitude lower than thresholds; for instance, effluents from sources have measured approximately 0.03 mg/L, while predicted environmental concentrations from modeled releases remain far below LC50 values. This disparity underscores minimal risk to ecosystems under diffuse release scenarios, as rapid dilution and — with half-lives of 1–4 weeks in and —limit persistence. 2-Butoxyethanol demonstrates low potential, with a low (log Kow ≈ 0.83) and no evidence of through food chains, as partitioning favors aqueous phases over lipid tissues in . Ecotoxicological impacts are thus primarily associated with acute high-concentration events, such as spills, rather than chronic accumulation or trophic transfer, rendering widespread ecological disruption unlikely absent containment failures.

Regulations

United States Standards

The Occupational Safety and Health Administration (OSHA) establishes a permissible exposure limit (PEL) for 2-butoxyethanol in workplace air of 50 parts per million (ppm) as an 8-hour time-weighted average (TWA), with a skin notation indicating potential significant absorption through the skin, intact or abraded, which must be considered in exposure assessments. This limit, derived from earlier evaluations of acute toxicity data including hemolysis risks at higher concentrations, prioritizes controlling inhalation and dermal routes based on empirical evidence from animal and limited human studies showing reversible effects below this threshold. The National Institute for Occupational Safety and Health (NIOSH) recommends a more stringent REL of 5 ppm TWA (skin), reflecting cautious interpretation of data on respiratory irritation and potential systemic effects, though OSHA's PEL remains enforceable. Under the Toxic Substances Control Act (TSCA), 2-butoxyethanol is listed on the TSCA Chemical Substance Inventory as an active substance, subjecting it to reporting and recordkeeping requirements for manufacturers and importers exceeding certain thresholds, but without prohibitions on production, import, or use, indicating regulatory determination of manageable risks through existing exposure controls rather than outright restriction. The Environmental Protection Agency (EPA) previously included 2-butoxyethanol (as monobutyl ether) on the Clean Air Act's list of hazardous air pollutants but removed it in November 2004 following review of toxicological data, including low carcinogenic potential and adequate margins of safety from environmental exposures, emphasizing evidence-based delisting over precautionary persistence on the list. In hydraulic fracturing operations, federal and state disclosure requirements—such as those under the Bureau of Land Management's rules for and various state registries—mandate reporting of 2-butoxyethanol when used as a reducer or in fracturing fluids, without imposing a nationwide ban, as empirical monitoring has not demonstrated widespread uncontrollable releases necessitating prohibition. This approach aligns with TSCA and Clean Air Act frameworks, focusing on transparency and site-specific informed by data and low potential rather than uniform curtailment.

Canadian and International Frameworks

In Canada, the 2-Butoxyethanol Regulations (SOR/2006-347), which established concentration limits for 2-butoxyethanol in products such as automobile cleaners (up to 10% w/w) and rug or carpet cleaners (up to 6% w/w), were repealed in 2025 and integrated into the broader Certain Products Containing Toxic Substances Regulations (SOR/2025-36). This consolidation, effective following publication in the Canada Gazette on March 12, 2025, streamlines oversight of toxic substances under the Canadian Environmental Protection Act, 1999, by maintaining product-specific concentration caps—such as limits below 6% w/w in general cleaning products—to mitigate health risks from dermal and inhalation exposure while permitting industrial applications with proper controls. The approach emphasizes risk-based exposure management over outright prohibition, aligning with assessments that tolerable concentrations (e.g., 11 mg/m³ in air) can safeguard public health when adhered to. Internationally, 2-butoxyethanol is regulated under the European Union's REACH framework (Regulation (EC) No 1907/2006), which classifies it as an irritant to and eyes (H315, H319) and acutely toxic via oral, dermal, and routes (Acute Tox. 3/4 categories), requiring registration, assessments, and controls for manufacturers and importers without authorizing unrestricted high-volume use in products like (limited to 4% in certain hair dyes). Harmonized classification under the (EU) No 1272/2008, updated in 2022 to include specific hazard entries for 2-butoxyethanol, supports global consistency via the Globally Harmonized System (GHS) for labeling and safety data sheets, focusing on protective measures like ventilation and rather than substance bans. The International Agency for Research on Cancer (IARC) classifies 2-butoxyethanol as Group 3 (not classifiable as to its carcinogenicity to humans), based on limited evidence in animals and inadequate data in humans, reinforcing regulatory emphasis on acute and irritancy hazards over oncogenic s.

Industrial Significance

Economic Role and Benefits

The global market for 2-butoxyethanol was valued at approximately $1.2 billion in 2024, with projections estimating to $1.85 billion by 2033, reflecting its role in solvent-dependent industries such as coatings, products, and inks. This expansion is driven by demand for versatile solvents that enhance and performance, supporting downstream manufacturing sectors with reliable supply chains for chemical intermediates derived from and n-butanol. In applications, 2-butoxyethanol provides superior for both water-soluble and oil-based systems, enabling the creation of concentrated formulations that require lower overall volumes compared to less efficient alternatives, thereby reducing and transportation costs. Its compatibility with diverse resins and improves product efficacy, such as faster drying times in lacquers and enhanced grease removal in cleaners, which translates to higher productivity in and operations without necessitating higher concentrations that could elevate expenses. These attributes position it as a cost-effective option over traditional solvents, which often demand greater quantities or additional additives to achieve equivalent dissolution power. The chemical's high production scale underpins in petrochemical synthesis and facilities, with its widespread adoption in household and industrial products sustaining ancillary jobs in distribution and across global supply networks. At regulated exposure levels, these gains from optimized outweigh potential handling costs, affirming its economic viability in compliant industrial practices.

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