Hubbry Logo
Butyl acetateButyl acetateMain
Open search
Butyl acetate
Community hub
Butyl acetate
logo
8 pages, 0 posts
0 subscribers
Be the first to start a discussion here.
Be the first to start a discussion here.
Butyl acetate
Butyl acetate
Butyl acetate
View on Wikipedia
from Wikipedia
n-Butyl acetate
Skeletal formula of butyl acetate
Ball-and-stick model of the butyl acetate molecule
Names
Preferred IUPAC name
Butyl acetate
Systematic IUPAC name
Butyl ethanoate
Other names
n-Butyl acetate
Acetic acid n-butyl ester
Butile
Identifiers
3D model (JSmol)
Abbreviations BuAcO
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.236 Edit this at Wikidata
EC Number
  • 204-658-1
KEGG
RTECS number
  • AF7350000
UNII
UN number 1123
  • InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 checkY
    Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3
    Key: DKPFZGUDAPQIHT-UHFFFAOYAF
  • CCCCOC(=O)C
Properties
CH3CO2(CH2)3CH3
Molar mass 116.160 g·mol−1
Appearance Colorless liquid
Odor Fruity
Density 0.8825 g/cm3 (20 °C)[1]
Melting point −78 °C (−108 °F; 195 K)[1]
Boiling point 126.1 °C (259.0 °F; 399.2 K) at 760 mmHg[1]
0.68 g/100 mL (20 °C)[1]
Solubility Miscible in EtOH
Soluble in acetone, CHCl3[1]
log P 1.82[1]
Vapor pressure
  • 0.1 kPa (−19 °C)
  • 1.66 kPa (24 °C)[1]
  • 44.5 kPa (100 °C)[2]
0.281 L·atm/mol
−77.47·10−6 cm3/mol
Thermal conductivity
  • 0.143 W/m·K (0 °C)
  • 0.136 W/m·K (25 °C)
  • 0.130 W/m·K (50 °C)
  • 0.116 W/m·K (100 °C)[1]
1.3941 (20 °C)[1]
Viscosity
  • 1.002 cP (0 °C)
  • 0.685 cP (25 °C)
  • 0.5 cP (50 °C)
  • 0.305 cP (100 °C)[1]
Structure
1.87 D (24 °C)[1]
Thermochemistry
225.11 J/mol·K[2]
−609.6 kJ/mol[2]
3467 kJ/mol[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark[3]
Warning
H226, H336[3]
P261[3]
NFPA 704 (fire diamond)
[4]
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 22 °C (72 °F; 295 K)[4]
370 °C (698 °F; 643 K)[4]
150 ppm[1] (TWA), 200 ppm[1] (STEL)
Lethal dose or concentration (LD, LC):
10768 mg/kg (~10.8g/kg) (rats, oral)[4]
160 ppm (rat, 4 hr)
2000 ppm (rat, 4 hr)
391 ppm (rat, 4 hr)
1242 ppm (mouse, 2 hr)[6]
14,079 ppm (cat, 72 min)
13,872 ppm (guinea pig, 4 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 150 ppm (710 mg/m3)[4]
REL (Recommended)
 TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)[5]
IDLH (Immediate danger)
 1700 ppm[5]
Related compounds
Related acetates
 Ethyl acetate
Propyl acetate
Amyl acetate
Related compounds
 Butanol
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 ?)

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.[7]

The other three isomers (four, including stereoisomers) of butyl acetate are isobutyl acetate, tert-butyl acetate, and sec-butyl acetate (two enantiomers).

Production and use

[edit]

Butyl acetate is commonly manufactured by the Fischer esterification of n-butanol and acetic acid with the presence of sulfuric acid:[7]

Butyl acetate is mainly used as a solvent for coatings and inks.[7] It is a component of fingernail polish.[8]

Occurrence in nature

[edit]

Apples, especially of the "Red Delicious" variety, are flavored in part by this chemical. The alarm pheromones emitted by the Koschevnikov gland of honey bees contain butyl acetate.

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Butyl acetate

View on Grokipedia
from Grokipedia
Butyl acetate, chemically known as n-butyl acetate or butyl , is a colorless, with a sweet, fruity odor and the molecular formula C₆H₁₂O₂ (MW 116.16 g/mol). It serves primarily as an organic solvent due to its low volatility and ability to dissolve resins, oils, and other substances, making it a key ingredient in industrial formulations. Produced industrially through the esterification of n-butanol and acetic acid in the presence of a catalyst, butyl acetate occurs naturally in trace amounts in fruits like bananas and is synthesized on a large scale for commercial use. Its physical properties include a of 126°C, a of -78°C, a of 0.88 g/cm³ at 20°C, and limited in (approximately 0.68% by weight at 20°C), though it is miscible with alcohols, ethers, and hydrocarbons. These characteristics contribute to its role in applications such as nitrocellulose lacquers, high-polish varnishes, photographic films, removers, perfumes, and food flavorings, where it imparts without excessive . While generally of low , butyl acetate is an irritant to the eyes, , and at high concentrations, with an OSHA of 150 ppm (8-hour TWA) and a of 22°C, necessitating careful handling to prevent fire hazards and health effects like or . Environmentally, it volatilizes readily into the atmosphere, where it undergoes photochemical degradation, but it poses minimal persistence in soil or water due to its physicochemical properties.

Chemical Identity and Structure

Nomenclature and Isomers

Butyl acetate, referring primarily to the straight-chain n-butyl , is systematically named butyl acetate under the International Union of Pure and Applied Chemistry (IUPAC) recommendations for esters, where the from the alcohol precedes the name of the carboxylate anion. This compound is alternatively designated as butyl ethanoate, emphasizing its derivation from butan-1-ol and ethanoic in substitutive . The CAS for n-butyl acetate is 123-86-4. Common names for this include n-butyl acetate and normal butyl acetate, which distinguish it from branched variants and reflect its historical usage in industrial and chemical contexts. Butyl acetate features three primary structural , differing in the branching of the butyl group while maintaining the ester functional group (CH₃COO-):
  • sec-Butyl acetate: CH₃CH₂CH(CH₃)OCOCH₃, CAS 105-46-4
  • : (CH₃)₂CHCH₂OCOCH₃, CAS 110-19-0
  • : (CH₃)₃COCOCH₃, CAS 540-88-5
These isomers are classified based on the carbon atom attached to the oxygen in the linkage—primary for n-butyl, secondary for sec-butyl, and tertiary for tert-butyl—allowing precise differentiation in chemical databases and regulatory contexts.

Molecular Structure

n-Butyl acetate possesses the molecular formula C₆H₁₂O₂. Its is CH₃CO₂(CH₂)₃CH₃, characterized by an functional group where a carbonyl carbon (C=O) is linked to an alkoxy oxygen that connects to the n-butyl chain. X-ray crystallography of n-butyl acetate at 150 K reveals key bond lengths in the ester linkage: the carbonyl C=O bond measures 1.2037 , the adjacent C-O bond is 1.3411 , and the O-C (alkyl) bond is 1.4571 . Bond angles around the ester include 123.27° for O=C-O, 115.87° for C(carbonyl)-O-C, 111.16° for O-C-CH₃, and 125.57° for O=C-C-CH₃. These dimensions reflect partial double-bond character in the C-O bond due to , influencing the molecule's planarity and reactivity. In both solid and solution states, n-butyl acetate predominantly adopts the s-trans conformation for the group, where the carbonyl oxygen and alkyl oxygen are trans across the C-O , minimizing steric repulsion and optimizing alignment. The s-cis conformation, with the oxygens cis, is higher in energy. The rotational barrier for interconversion between s-trans and s-cis forms in esters is approximately 11-12 kcal/mol, permitting facile at ambient temperatures while maintaining the s-trans preference.

Physical and Chemical Properties

Physical Properties

n-Butyl acetate is a colorless liquid with a characteristic fruity, banana-like odor. Its molar mass is 116.16 g/mol, with a density of 0.882 g/cm³ at 20°C, a melting point of -78°C, and a boiling point of 126°C. The compound exhibits limited in , at 0.7 g/100 mL at 20°C, but is fully miscible with common organic solvents such as and acetone. Additional physical characteristics include a of 8 mmHg at 20°C and a of 1.395 at 20°C. Among the butyl acetate isomers, n-butyl acetate has the highest at 126°C, while boils at 118°C and sec-butyl acetate at 112°C; densities are similar, around 0.87–0.88 g/cm³ at 20°C. This banana-like odor also plays a role in its natural occurrence in fruits such as bananas.

Chemical Properties

n-Butyl acetate, as an , exhibits characteristic reactivity primarily through its ester functional group, which is susceptible to under both acidic and basic conditions, producing n-butanol and acetic acid. In acidic hydrolysis, the reaction is reversible and catalyzed by strong acids such as , following the mechanism. The equation for acid-catalyzed hydrolysis is: \ceCH3CO2C4H9+H2O⇌[H2SO4]CH3CO2H+C4H9OH\ce{CH3CO2C4H9 + H2O ⇌[H2SO4] CH3CO2H + C4H9OH} Under basic conditions, such as with , hydrolysis proceeds via , yielding the carboxylate salt and alcohol, and is irreversible due to the formation of the stable . n-Butyl acetate demonstrates good thermal stability under normal storage conditions but decomposes upon heating, releasing acrid smoke and irritating fumes. It resists oxidation more effectively than primary alcohols like n-butanol, which readily oxidize to aldehydes and carboxylic acids, whereas the linkage provides greater stability against mild oxidants. The carbonyl oxygen in n-butyl acetate is weakly basic, with the pKa of its protonated conjugate acid approximately -7, reflecting the low nucleophilicity typical of carbonyls due to delocalization. This basicity influences its coordination with Lewis acids in catalytic processes but limits reactivity with weaker electrophiles.

Synthesis and Production

Laboratory Synthesis

n-Butyl acetate, a common , was first synthesized in the during the using classical esterification techniques, with the method formalized by and Arthur Speier in 1895 through their description of acid-catalyzed ester formation. The standard laboratory preparation employs Fischer esterification, involving the reversible reaction of acetic acid and n-butanol in the presence of a concentrated catalyst under conditions. The balanced equation is: \ceCH3CO2H+C4H9OH⇌[H2SO4]CH3CO2C4H9+H2O\ce{CH3CO2H + C4H9OH ⇌[H2SO4] CH3CO2C4H9 + H2O} Typically, equimolar amounts or an excess of n-butanol (e.g., 30 mL n-butanol to 40 mL acetic acid) are mixed with 3-5% sulfuric acid by volume and heated to reflux for 1-2 hours to drive the equilibrium forward. Post-reaction, the mixture is cooled and transferred to a separatory funnel for washing with cold water, followed by extraction with sodium bicarbonate solution to neutralize acids and remove unreacted carboxylic acid, then with saturated sodium chloride to aid phase separation. The organic layer is dried over anhydrous magnesium sulfate or sodium sulfate and purified by simple distillation, collecting the fraction boiling at approximately 126°C. Yields are typically 70-80% when optimized by excess alcohol or water removal, though equilibrium limitations often cap theoretical conversion around 67-70% without such measures. Alternative laboratory methods include , where n-butyl acetate is prepared by reacting or with n-butanol, often facilitated by or base catalysts to exchange the alkoxy groups under milder heating than direct esterification. Enzymatic synthesis offers a greener approach, utilizing s such as Candida antarctica lipase B to catalyze the esterification of acetic and n-butanol at ambient temperatures (20-40°C) in non-aqueous media, achieving high selectivity and yields up to 90% while avoiding harsh acids. These methods are particularly useful in educational settings for demonstrating biocatalysis or in research requiring .

Industrial Production

The primary industrial production of n-butyl acetate involves the continuous esterification of n-butanol with acetic acid in the presence of acid catalysts, such as or ion-exchange resins like Amberlyst-15, conducted within reactive distillation columns to simultaneously facilitate the reaction and product separation. This reversible reaction, CH₃COOH + C₄H₉OH ⇌ C₄H₉OCOCH₃ + H₂O, relies on the removal of water to drive equilibrium toward the , achieving high conversion rates in a single that enhances process efficiency and reduces compared to batch methods. The feedstocks, primarily derived from petrochemical sources like for butanol and methanol for acetic acid, support large-scale operations. Global production of n-butyl acetate exceeds 1.8 million metric tons annually as of 2024, driven by demand in coatings and adhesives industries, with major producers located in regions leveraging integrated complexes. water, formed stoichiometrically during esterification, is managed through , often utilizing the product n-butyl acetate itself as an entrainer to form a heterogeneous (approximately 88.7 wt% butyl acetate and 11.3 wt% at 90.2°C), enabling effective separation in a and of unreacted components. This approach minimizes waste and recovers excess and acetic acid, contributing to overall process yields above 95%. Post-2010 advancements in energy efficiency have focused on heat integration strategies, such as thermally coupled reactive combined with membranes, reducing steam consumption by up to 40% and total demand to around 61 MJ/kg in optimized plants. These improvements, including feed preheating and multi-effect , have lowered operational costs and environmental footprints in commercial facilities. Recent developments by 2025 emphasize through bio-based feedstocks, particularly fermentation-derived n-butanol from renewable via acetone-butanol-ethanol (ABE) processes, enabling greener production of n-butyl acetate with reduced carbon emissions. of microorganisms like has also enabled direct one-pot biosynthesis of butyl acetate from glucose, offering potential scalability for bio-refineries and aligning with regulatory pressures for low-carbon solvents.

Applications and Uses

Solvent Applications

n-Butyl acetate is widely employed as a volatile in the paints and coatings industry, particularly in lacquers and varnishes, where it facilitates the dissolution of resins and promotes even film formation during application. Its moderate evaporation rate, standardized at 1.0 relative to n-butyl itself, enables quick drying times while minimizing defects such as blushing or solvent pop under typical conditions. This property makes it especially suitable for automotive topcoats and wooden furniture finishes, where controlled release ensures durable, high-gloss surfaces. It is also used in the production of photographic films due to its ability to dissolve . In printing inks and adhesives, n-butyl acetate excels at dissolving nitrocellulose and various resins, enhancing flow properties and strength in formulations. It is commonly incorporated as a key component, often comprising 20-50% of the mixture to achieve optimal and drying performance in flexographic, gravure, and processes. This solvency contributes to sharp color definition and efficient bonding in industrial adhesives without compromising substrate integrity. As a component in and nail polish removers, n-butyl acetate imparts a glossy finish and supports rapid drying by evaporating at a controlled rate, leaving behind a smooth on the nail surface. Its use in cosmetic formulations dates back to the , coinciding with the development of nitrocellulose-based lacquers adapted from automotive paints, and it remains a preferred alternative to more hazardous solvents like due to its milder odor and lower volatility. The advantages of n-butyl acetate as a solvent include its relatively low toxicity compared to aromatic alternatives such as , with acute exposure limits indicating low to moderate risk in occupational settings, and its strong solvency for cellulose esters like , attributed to a Hildebrand solubility parameter of approximately 8.5 cal1/2cm−3/28.5 \, \text{cal}^{1/2} \text{cm}^{-3/2}. These characteristics, combined with its pleasant fruity odor and compatibility with a range of polymers, position it as a versatile choice for industrial solvent applications requiring balanced performance and safety.

Other Industrial Uses

Beyond its primary role as a solvent, n-butyl acetate serves as a flavoring agent in the , where it imparts a characteristic banana-like aroma. It is approved by the U.S. (FDA) as a synthetic substance and adjuvant under 21 CFR 172.515, allowing its use in various products at low concentrations to enhance fruity . Typical maximum use levels, as evaluated by the Flavor and Extract Manufacturers Association (FEMA), reach up to 32 ppm in baked goods and 11 ppm in non-alcoholic beverages, contributing to synthetic banana flavors without altering the overall product profile. In the fragrance industry, n-butyl acetate is employed to provide sweet, fruity, and green in perfumes, leveraging its ethereal, banana-like odor to create complex scent compositions. n-Butyl acetate also functions as an extraction solvent in pharmaceutical processing and perfume production. In pharmaceuticals, it facilitates the separation and purification of active compounds due to its selective solvency for organic materials. For perfume oil extraction, it acts as a to isolate essential oils and resins from natural sources, aiding in the concentration of aromatic components while maintaining their integrity. Emerging research highlights the potential of n-butyl as a component and fuel additive. With a research number (RON) of approximately 101 for the neat compound, it offers high anti-knock properties suitable for blending into to enhance ratings. Studies on bio-based n-butyl , produced via microbial of , demonstrate its viability as a renewable blendstock, achieving titers up to 24.7 g/L and reducing by over 60% compared to petroleum-derived fuels. Ongoing research as of 2025, including studies on dynamics and phase equilibrium modeling published in August and September 2025, explores its integration into sustainable fuel formulations for improved engine performance and lower emissions. In miscellaneous applications, n-butyl acetate is incorporated into industrial agents for its ability to dissolve oils, greases, and residues on machinery and surfaces. Additionally, it serves as a reference standard in for analyzing solvents and volatile compounds in environmental and industrial samples.

Natural Occurrence

In Fruits and Foods

n-Butyl acetate occurs naturally in various plant-derived foods, where it plays a significant role in defining aroma profiles through its fruity, solvent-like scent reminiscent of . In apples, it is particularly abundant in the variety, serving as a primary responsible for the characteristic "red apple" aroma. Concentrations can reach up to 29.5 mg/kg in apple fruit, highlighting its contribution to the overall volatile composition that enhances sensory appeal during consumption. In bananas and other fruits such as grapes, mangoes, melons, and strawberries, n-butyl acetate contributes to the ripening scent, with levels typically increasing as the fruit matures due to enhanced ester production. For instance, during banana ripening, concentrations of acetates like n-butyl acetate rise, often reaching 0.03–0.09 mg/kg in mature fruit, which supports the development of the sweet, tropical aroma associated with ripeness. The U.S. Food and Drug Administration recognizes n-butyl acetate as generally recognized as safe (GRAS) for use as a flavoring agent or adjuvant in food products. It is commonly incorporated into confectionery, beverages, and other processed foods to impart artificial fruit flavors, mimicking its natural sensory contributions. In plants, the biosynthesis of n-butyl acetate proceeds via alcohol acyltransferases (AATs), enzymes that catalyze the esterification of butanol with acetyl-CoA, the latter derived from central metabolic pathways like glycolysis and the tricarboxylic acid cycle. Butanol itself arises from the reduction of butyraldehyde, often linked to amino acid catabolism or fatty acid derivatives, enabling the accumulation of this ester during fruit development and ripening.

In Biological Systems

n-Butyl acetate serves as a minor component in the alarm blend released by worker honeybees (Apis mellifera) from the Koschewnikov associated with the sting apparatus. This volatile contributes to eliciting defensive behaviors, such as of nestmates and attack responses, when bees perceive a threat. Bioassays have demonstrated its alarm activity, comparable to other acetate esters in the blend, by attracting and exciting workers at low concentrations applied to observation hives. The role of such acetate esters in insect alarm communication has been recognized since discoveries in the mid-20th century, highlighting their conservation across social hymenopteran species for coordinating colony defense. In microbial systems, n-butyl acetate is biosynthesized during by yeasts such as and certain , including species involved in production. This occurs through the esterification of n-butanol and acetic acid, generated as byproducts of glucose metabolism under anaerobic conditions. For instance, in wine fermentation, yeast strains produce n-butyl acetate as part of the volatile ester profile that influences aroma development, while in bioethanol processes, similar microbial pathways yield it alongside primary alcohols. These natural production routes underscore n-butyl acetate's integration into microbial metabolic networks for energy generation and stress response. Within mammalian , n-butyl acts as a transient intermediate in biotransformation pathways, primarily undergoing rapid to n-butanol and acetic acid. This is catalyzed by carboxylesterases, ubiquitous enzymes in liver, , and intestinal tissues that efficiently cleave short-chain esters like n-butyl . Studies in have shown high rates for n-butyl in respiratory and hepatic microsomes, facilitating quick elimination via and further oxidation to innocuous metabolites. Such metabolic handling prevents accumulation and supports the body's capacity to process environmental or dietary exposures.

Safety, Health, and Environmental Impact

Health and Toxicity Effects

n-Butyl acetate exhibits low via oral and routes. The oral LD50 in rats is approximately 10,760 mg/kg body weight, indicating minimal risk from ingestion under typical exposure scenarios. LC50 values in rats exceed 4,000 ppm over 4 hours, further demonstrating low systemic from vapor exposure. However, direct contact causes to the eyes and ; splashes can lead to severe eye , redness, and potential corneal , while prolonged exposure may result in defatting and . High airborne concentrations above occupational limits can induce , manifesting as narcosis, drowsiness, or . Chronic exposure to n-Butyl acetate at elevated doses may pose risks to reproductive health, including potential developmental toxicity observed in , such as reduced fetal weight in rats exposed to 1,500 ppm via . No evidence of carcinogenicity has been established; the International Agency for Research on Cancer (IARC) has not classified n-butyl acetate due to insufficient data, placing it in Group 3 (not classifiable as to its carcinogenicity to humans). Occupational exposure limits are set to prevent adverse effects: the OSHA (PEL) is 150 ppm as an 8-hour time-weighted average (TWA), while the NIOSH (REL) is 150 ppm TWA with a (STEL) of 200 ppm. Common symptoms from overexposure include , , , and irritation of the . Upon absorption, n-butyl acetate undergoes rapid metabolism primarily through hydrolysis by esterases in the blood and liver, yielding n-butanol and acetic acid as primary metabolites. The half-life in human blood is approximately 4 minutes, facilitating quick biotransformation and excretion, mainly via the lungs and urine as metabolites. This efficient metabolism contributes to its overall low toxicity profile in humans.

Flammability and Handling Hazards

n-Butyl acetate is a with a of 22°C, indicating that it can ignite at relatively low temperatures when exposed to an open flame, spark, or other ignition source. Its is 421°C, above which it can spontaneously combust in air. The flammable limits in air range from 1.7% to 7.6% by volume, meaning mixtures within this concentration range can form vapors, particularly in confined or poorly ventilated spaces. Under the Globally Harmonized System (GHS), n-butyl acetate is classified as a , Category 3, with the hazard statement H226: "Flammable liquid and vapour." Safe handling requires use in well-ventilated areas to prevent vapor buildup, and all potential ignition sources such as open flames, hot surfaces, sparks, and must be avoided. Grounding and bonding of containers during transfer is essential to mitigate static discharge risks. For storage, n-butyl acetate should be kept in cool, well-ventilated areas in tightly sealed, grounded metal containers to minimize evaporation and risks. It is incompatible with strong oxidizing agents, alkali metals, and certain plastics or rubber, which can lead to violent reactions or container degradation. Incidents involving n-butyl acetate are rare but notable, particularly prior to enhanced regulations in the , often resulting from vapor accumulation in industrial settings. For instance, in 1992, a at the Allied Colloids facility in the destroyed vehicles loaded with 16 tonnes of the substance due to ignition of accumulated vapors.

Environmental Fate and Regulation

n-Butyl acetate is classified as a (VOC) and, when released into the environment, tends to volatilize rapidly into the atmosphere due to its high . In the air, it primarily degrades through photochemical oxidation via reaction with hydroxyl radicals, with an estimated atmospheric of approximately 3-4 days under typical conditions. In aqueous environments, n-butyl acetate exhibits ready biodegradability. Using standard BOD dilution methods with inoculum, it achieves a theoretical BOD of about 56% over 5 days and up to 86% over 20 days, indicating efficient microbial degradation. Its biodegradability aligns with natural degradation processes in biological systems, where enzymatic contributes to breakdown. n-Butyl acetate has a low potential, characterized by an (log Kow) of 1.78, which suggests minimal uptake and retention in aquatic organisms. Due to its volatility and rapid , it does not persist in or , leaching minimally and degrading via microbial activity. Under the European Union's REACH regulation, n-butyl acetate is registered but does not require authorization, as it is not designated as a . In the United States, the Agency regulates it as a VOC under the to control contributions to formation through emissions limits and reporting requirements. n-Butyl acetate is not listed under California's Proposition 65. In the 2020s, regulatory and industry efforts have emphasized reducing n-butyl emissions in the coatings sector, promoting low-VOC formulations and advanced capture technologies to comply with air quality standards. Sustainability initiatives include shifting to bio-based production routes, utilizing renewable feedstocks such as bioethanol to lower the of global manufacturing.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/Butyl-Acetate
  2. https://www.tceq.texas.gov/downloads/toxicology/dsd/final/butylacetate.pdf
  3. https://www.nj.gov/health/eoh/rtkweb/documents/fs/1329.pdf
  4. https://www.chemspider.com/Chemical-Structure.29012.html
  5. https://www.inchem.org/documents/cicads/cicads/cicad64.htm
  6. https://www.sigmaaldrich.com/US/en/product/aldrich/b88209
  7. https://www.acgih.org/butyl-acetates-all-isomers/
  8. https://doi.org/10.1107/S1600536805000371
  9. https://pubs.acs.org/doi/10.1021/ja00254a006
  10. https://www.sciencedirect.com/science/article/abs/pii/S0167732219370394
  11. https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0399&p_version=2
  12. https://www.sigmaaldrich.com/US/en/product/mm/101974
  13. https://pubchem.ncbi.nlm.nih.gov/compound/Isobutyl-Acetate
  14. https://www.dir.ca.gov/dosh/DoshReg/5155-Meetings/sec-Butyl-acetate-2018-12-04.pdf
  15. https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/The_Basics_of_General_Organic_and_Biological_Chemistry_(Ball_et_al.)/15%3A_Organic_Acids_and_Bases_and_Some_of_Their_Derivatives/15.08%3A_Hydrolysis_of_Esters
  16. https://pubchem.ncbi.nlm.nih.gov/compound/Butyl-Acetate#section=Decomposition
  17. https://pubchem.ncbi.nlm.nih.gov/compound/Butyl-Acetate#section=Reactivity-Profile
  18. https://www.chem.indiana.edu/wp-content/uploads/2018/03/pka-chart.pdf
  19. https://www.chemistrylearner.com/fischer-esterification.html
  20. https://www.masterorganicchemistry.com/2022/11/16/fischer-esterification/
  21. https://ocw.mit.edu/courses/5-310-laboratory-chemistry-fall-2019/c264e7bace5b759650eea4debb3f1006_MIT5_310F19_Lab4.pdf
  22. https://people.chem.umass.edu/samal/269/ester.pdf
  23. https://pubmed.ncbi.nlm.nih.gov/31741085/
  24. https://www.sciencedirect.com/science/article/abs/pii/S0920586115001066
  25. https://www.chemicalbook.com/article/butyl-acetate-uses-and-commercial-manufacturing-method.htm
  26. https://www.irjet.net/archives/V3/i8/IRJET-V3I8323.pdf
  27. https://pubs.acs.org/doi/abs/10.1021/acs.iecr.3c01933
  28. https://www.esig.org/wp-content/uploads/2025/01/Eco-profile_OSPA_nButyl-Acetate__after_review_11.12.2024.pdf
  29. https://www.chemanalyst.com/industry-report/butyl-acetate-market-758
  30. https://www.sciencedirect.com/science/article/abs/pii/S0959152417302214
  31. https://www.sciencedirect.com/science/article/pii/S2666952823000237
  32. https://www.sciencedirect.com/science/article/abs/pii/S0255270118312121
  33. https://www.researchgate.net/publication/329255762_Improvement_of_the_Butyl_Acetate_Process_through_Heat_Integration_A_Sustainability-Based_Assessment
  34. https://www.sciencedirect.com/science/article/abs/pii/S0957582021007035
  35. https://www.globenewswire.com/news-release/2025/05/13/3080273/0/en/n-Butanol-Market-to-Reach-USD-9-02-Billion-by-2032-Driven-by-Bio-Based-Production-and-Pharmaceutical-Demand-Report-by-SNS-Insider.html
  36. https://www.procurementresource.com/reports/butanol-manufacturing-plant-project-report
  37. https://pmc.ncbi.nlm.nih.gov/articles/PMC8864926/
  38. https://biotechnologyforbiofuels.biomedcentral.com/articles/10.1186/s13068-021-02053-2
  39. https://www.univarsolutions.com/ca/en/20227
  40. https://download.basf.com/p1/000000000030034818_SDS_GEN_GB/en_GB/n-BUTYL__ACETATE_30034818_SDS_GEN_GB_en_15-0.pdf
  41. https://www.celanese.com/-/media/Intermediate-Chemistry/Files/Brochures/nButyl-Acetate-Brochure.pdf
  42. https://cen.acs.org/articles/86/i32/Nail-Polish.html
  43. https://bcgc.berkeley.edu/sites/default/files/copy_of_greener_solutions_nail_polish_final_report.pdf
  44. https://www.cosmeticsinfo.org/ingredient/butyl-acetate/
  45. https://www.hedinger.de/fileadmin/content/03_Geschaeftsbereiche/Industrie/n-Butyl_Acetate.pdf
  46. https://www.ecfr.gov/current/title-21/section-172.515
  47. https://www.thegoodscentscompany.com/data/rw1019351.html
  48. https://hansonchemicals.com/products/butyl-acetate/
  49. https://www.pnnl.gov/main/publications/external/technical_reports/PNNL-28713.pdf
  50. https://www.energy.gov/sites/default/files/2021-04/beto-11-peer-review-2021-cooptima-wang_r1.pdf
  51. https://pubs.rsc.org/en/content/articlehtml/2025/re/d5re00214a
  52. https://www.researchgate.net/publication/353805967_Combustion_of_n-butyl_acetate_synthesized_by_a_new_and_sustainable_biological_process_and_comparisons_with_an_ultrapure_commercial_n-butyl_acetate_produced_by_conventional_Fischer_esterification
  53. https://www.researchgate.net/publication/393402605_n-Butyl_alcohol_and_n-butyl_acetate_as_potential_fuel_components_experimental_phase_and_chemical_equilibrium_calculation_and_modeling
  54. https://riverlandtrading.com/news-detail?id=57
  55. https://www.sigmaaldrich.com/US/en/product/sial/73285
  56. https://pmc.ncbi.nlm.nih.gov/articles/PMC5253989/
  57. https://onlinelibrary.wiley.com/doi/10.1155/2019/7653154
  58. https://pmc.ncbi.nlm.nih.gov/articles/PMC6270112/
  59. https://cfsanappsexternal.fda.gov/scripts/fdcc/index.cfm?set=FoodSubstances&id=BUTYLACETATE
  60. https://pmc.ncbi.nlm.nih.gov/articles/PMC520758/
  61. https://link.springer.com/article/10.1007/BF00987794
  62. https://academic.oup.com/aesa/article/93/6/1329/161481
  63. https://www.frontiersin.org/journals/behavioral-neuroscience/articles/10.3389/neuro.08.005.2007/full
  64. https://pmc.ncbi.nlm.nih.gov/articles/PMC11353631/
  65. https://pubmed.ncbi.nlm.nih.gov/3576643/
  66. https://pmc.ncbi.nlm.nih.gov/articles/PMC6146386/
  67. https://www.dir.ca.gov/dosh/DoshReg/5155-Meetings/n-Butyl-acetate-2018-12-04.pdf
  68. https://louisville.edu/micronano/files/documents/safety-data-sheets-sds/butyl-acetate/
  69. https://haz-map.com/Agents/321
  70. https://www.canada.ca/en/health-canada/services/environmental-workplace-health/occupational-health-safety/workplace-hazardous-materials-information-system/hazardous-substance-assessments/n-butyl-acetate.html
  71. https://www.cdc.gov/niosh/npg/npgd0072.html
  72. https://www.univarsolutions.com/proxy/index/index/?e=1%253A3%253A8n6UFhOiZ0YbwAvtNswjBfiIbXnYGFiUVmOCepLNf6AhztwH3PPGr9mKYudwZtqNmtM1dI7r%252FG7Yj51Xuo3xJd1n5vu8czMzdc%252BemcDVmkcZ%252Ft0wlyWDT895W2UJ%252FcG%252BLJAARWs7JyjnxnwLpCouke05sZ78TENztqRBEsK2vRLKs6Jb%252Bg%253D%253D&srsltid=AfmBOoruCmBHkGJM_iUIYqEje9eKcb44x6_kmsDlQbIxs0gyoRsSvT2g
  73. https://www.dir.ca.gov/dosh/DoshReg/5155-Meetings/n-Butyl-acetate.pdf
  74. https://cameochemicals.noaa.gov/chris/BCN.pdf
  75. https://www.sigmaaldrich.com/US/en/sds/aldrich/w217409
  76. https://www.flinnsci.com/sds_883-butyl-acetate/sds_883/
  77. https://www.icheme.org/media/13703/the-fire-at-allied-colloids-limited.pdf
  78. https://www.ashland.com/file_source/Ashland/Documents/Sustainability/rc_n-butyl_acetate_pss.pdf
  79. https://www.epa.gov/ground-level-ozone-pollution/revision-regulatory-definition-volatile-organic-compounds
  80. https://pubs.rsc.org/en/content/articlehtml/2024/gc/d4gc01962h
Add your contribution
Related Hubs
User Avatar
No comments yet.