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Dibutyl ether

Dibutyl ether, also known as di-n-butyl ether or n-butyl ether, is an organic compound with the molecular formula C₈H₁₈O and the structural formula (CH₃(CH₂)₃)₂O.^[1]^[2] It appears as a clear, colorless liquid with a mild ethereal odor, characterized by low water solubility (0.113 g/L at 20 °C) and a density of 0.764 g/mL at 25 °C.^[1]^[2] Key physical properties include a boiling point of 142–143 °C, a melting point of -98 °C, and a flash point of 25–28 °C, making it volatile and highly flammable.^[1]^[3] Chemically, it is stable under normal conditions but can form explosive peroxides upon prolonged exposure to air and reacts violently with strong oxidizing agents.^[1]^[3] Dibutyl ether is primarily utilized as a solvent in organic synthesis, particularly for Grignard, Wittig, and alkyl lithium reactions, due to its ability to dissolve resins, oils, fats, hydrocarbons, and various natural and synthetic materials.^[1]^[2] It serves as an extracting agent in chemical processes and has applications in analytical chemistry, laboratory synthesis, and industrial formulations such as coatings and fuel additives.^[4]^[2] Emerging research explores its potential as a biofuel component or diesel blend due to its high cetane number, energy content, and non-miscibility with water, though commercial adoption remains limited.^[2] Safety considerations for dibutyl ether include its classification as a flammable liquid (Category 3) that poses risks of skin and eye irritation, respiratory effects, and environmental harm to aquatic life.^[1]^[2] Proper handling requires ventilation, protective equipment, and storage away from ignition sources and oxidizers to prevent peroxide formation.^[3]

Properties

Physical properties

Dibutyl ether, with the molecular formula C₈H₁₈O (or (CH₃CH₂CH₂CH₂)₂O), has a molar mass of 130.23 g/mol. It appears as a clear, colorless liquid at room temperature. The compound exhibits a mild, ethereal odor, often described as pleasant or fruity in character. Dibutyl ether has a density of 0.767 g/cm³ at 20 °C, making it lighter than water. Its melting point is -98 °C, and the boiling point is 142 °C at standard pressure. The vapor density is 4.48 relative to air, indicating that its vapors are heavier than air and may accumulate in low-lying areas.

Property	Value	Conditions/Source
Solubility in water	0.113 g/L	20 °C [Sigma-Aldrich]
Solubility in organic solvents	Highly soluble (e.g., in acetone)	General solvent behavior [Sigma-Aldrich]
Vapor pressure	4.8 mmHg	20 °C [Sigma-Aldrich]
Flash point	25 °C	Closed cup [ChemicalBook]
Autoignition temperature	185 °C	[Sigma-Aldrich]

As a volatile liquid, dibutyl ether is flammable, with a low flash point that necessitates careful handling to prevent ignition sources. It tends to form peroxides upon prolonged exposure to air, which can affect its stability during storage.

Chemical properties

Dibutyl ether is classified as a symmetric dialkyl ether, featuring two n-butyl groups attached to the oxygen atom, which imparts it with characteristic ether functionality.^[4] As a low-polarity, aprotic solvent, dibutyl ether exhibits minimal ability to form hydrogen bonds, rendering it unsuitable as a hydrogen bond donor and favoring interactions with nonpolar substances.^[5]^[6] It demonstrates high miscibility with nonpolar organic solvents while showing immiscibility with water due to its limited solubility, typically below 0.2 g/100 mL.^[5]^[4] Dibutyl ether maintains stability under reducing conditions and basic environments, resisting degradation from common reducing agents or bases.^[7]^[8] However, it is susceptible to oxidation, particularly forming explosive peroxides upon prolonged exposure to oxygen, light, or heat, necessitating storage precautions such as the addition of stabilizers like butylated hydroxytoluene (BHT) or maintenance under an inert atmosphere to mitigate autoxidation risks.^[5]^[4]^[9] This aprotic character also enables its use as a solvent for reactive organometallics, such as phenyllithium.^[5]

Synthesis

Industrial production

Dibutyl ether is primarily produced on an industrial scale through the acid-catalyzed dehydration of 1-butanol, utilizing sulfuric acid as a homogeneous catalyst at elevated temperatures typically ranging from 100 to 140 °C.^[4]^[10] The overall reaction involves the condensation of two molecules of 1-butanol to form the ether and water, represented by the equation:

$2 \ce{C4H9OH} \rightarrow \ce{(C4H9)2O} + \ce{H2O}

This process achieves high yields, often exceeding 80%, depending on reaction conditions and catalyst concentration, with sulfuric acid facilitating protonation of the alcohol to promote ether formation over competing side reactions like alkene production.^[11]^[10] An alternative industrial method employs heterogeneous catalysis, such as dehydration over alumina or other solid acids like ferric chloride or copper sulfate, conducted in the vapor phase at approximately 140–300 °C to enhance selectivity and ease of catalyst handling.^[4]^[12] This approach allows for continuous operation and reduces corrosion issues associated with liquid acids, though it requires precise temperature control to minimize butene byproducts.^[11] Butanol feedstocks for these processes are sourced from both petrochemical routes, such as the oxo-process from propylene, and renewable pathways via fermentation of biomass-derived sugars, enabling sustainable production with yields maintained through dry butanol purification to prevent water inhibition.^[13] Byproduct water is efficiently removed via distillation or azeotropic separation, while scale-up challenges, including catalyst regeneration for heterogeneous systems through calcination or washing, are addressed to ensure economic viability and long-term operation.^[13]^[10] The development of dibutyl ether production emerged in the early 20th century, driven by growing demand for inert solvents in organic synthesis and extractions, with modern processes incorporating bio-based butanol to align with sustainability goals and reduce reliance on fossil feedstocks.^[14]^[13]

Laboratory preparation

Dibutyl ether can be prepared in the laboratory via a variant of the Williamson ether synthesis, involving the SN2 reaction of sodium butoxide with 1-bromobutane under reflux conditions in an anhydrous solvent such as dry ethanol or diethyl ether.^[15] Sodium butoxide is first generated by treating 1-butanol with sodium metal or sodium hydride to form the alkoxide ion, which then acts as a nucleophile to displace the bromide ion.^[15] The reaction proceeds as follows:

\text{C}_4\text{H}_9\text{ONa} + \text{C}_4\text{H}_9\text{Br} \rightarrow (\text{C}_4\text{H}_9)_2\text{O} + \text{NaBr}

This method is preferred for symmetrical ethers like dibutyl ether due to the use of a primary alkyl halide, which minimizes elimination side products.^[15] An alternative laboratory approach involves acid-catalyzed dehydration of 1-butanol using concentrated sulfuric acid at controlled temperatures around 130–140°C, adapting industrial conditions for smaller scales.^[15] The reaction mechanism entails protonation of one alcohol molecule, followed by nucleophilic attack from a second alcohol molecule to form the ether and water.^[15] This method is suitable for primary alcohols but requires careful temperature control to favor ether formation over alkene production.^[15] Following synthesis, the crude product is purified by fractional distillation under an inert atmosphere, such as nitrogen, to isolate the ether (boiling point 142°C) and prevent peroxide formation from exposure to air and light.^[16] Drying agents like calcium chloride or molecular sieves are employed to remove residual water.^[15] Laboratory yields for these methods typically range from 70% to 90%, depending on reaction scale and purity of reagents.^[17] Precautions include maintaining anhydrous conditions throughout the Williamson synthesis to avoid quenching the alkoxide with moisture, which would reduce yields through side reactions forming butanol.^[15] In both methods, all glassware must be dried, and reactions conducted in a well-ventilated fume hood due to the volatility and flammability of the reagents.^[15]

Reactions

Cleavage reactions

Dibutyl ether, as a symmetrical dialkyl ether with primary alkyl groups, undergoes cleavage primarily through acid-catalyzed reactions that sever the C-O bond, producing alkyl halides or alcohols depending on the reagent and conditions. The reaction with hydrogen halides such as HI or HBr, typically under heating, yields 1-butanol and the corresponding butyl halide. With excess HI at 130 °C, complete cleavage occurs, converting the intermediate alcohol to 1-iodobutane and yielding two equivalents of the alkyl iodide overall.^[18]^[19] The mechanism initiates with protonation of the ether oxygen by the acid, generating an oxonium ion intermediate that enhances the electrophilicity of the carbon atoms attached to oxygen. This is followed by nucleophilic displacement of the alcohol by the halide ion via an SN2 pathway, favored for primary alkyl groups like butyl, which minimizes steric hindrance and prevents carbocation formation or rearrangement. Under forcing conditions with excess halide, the resulting alcohol undergoes a second SN2 substitution to form the additional alkyl halide.^[20]^[18] A representative equation for the initial cleavage step is:

(C_4H_9)_2O + HI \rightarrow C_4H_9I + C_4H_9OH

The primary butyl chains ensure high selectivity for SN2 products, with no preference between the two identical groups in this symmetrical ether. Partial cleavage to the alcohol-halide pair predominates with one equivalent of HI at lower temperatures, while excess reagent and heat drive full conversion to dihalide.^[19]^[18] Alternative cleaving agents include hot concentrated H₂SO₄, which protonates the oxygen and leads to hydrolysis, forming 1-butanol and butyl hydrogen sulfate. Boron tribromide (BBr₃) also effects cleavage by coordinating to the oxygen and facilitating bromide attack, ultimately yielding alkyl bromides after aqueous workup, though it is often employed for more selective transformations in complex molecules.^[21]^[22]

Oxidation reactions

Dibutyl ether undergoes autoxidation in the presence of air, leading to the slow formation of hydroperoxides and dialkyl peroxides such as dibutyl peroxide.^[23] This process is a radical chain reaction initiated by hydrogen abstraction, primarily at the alpha C-H bonds adjacent to the oxygen atom, followed by oxygen addition to form peroxy radicals.^[24] The reaction can be represented simplistically as:

(\ce{C4H9})_2\ce{O} + \ce{O2} \rightarrow (\ce{C4H9O2})_2 \quad \text{or related hydroperoxides}

Autoxidation is accelerated by exposure to light, elevated temperatures, and trace metal impurities, which act as catalysts for radical initiation.^[16] The resulting peroxides pose significant risks due to their explosive nature, particularly when concentrated or distilled, as they can detonate upon shock or heating.^[23] Peroxides in dibutyl ether can be detected using potassium iodide-starch test paper, where a color change to blue or black indicates their presence through iodide oxidation to iodine.^[25] For safe handling, accumulated peroxides are decomposed by treatment with reducing agents such as sodium thiosulfate or ferrous sulfate solutions.^[16] Under controlled conditions with common oxidants, dibutyl ether exhibits limited reactivity due to the stability of the ether linkage; for instance, it does not undergo significant oxidation with potassium permanganate (KMnO₄) under standard aqueous conditions, as saturated ethers lack readily oxidizable functional groups like double bonds or secondary alcohols.^[26]

Applications

Solvent uses

Dibutyl ether serves as an effective aprotic solvent in organometallic chemistry, particularly for stabilizing reactive species such as organolithium compounds. It is commonly employed to prepare phenyllithium solutions at concentrations around 1.9 M, where its non-protic nature prevents protonation and maintains reagent integrity during storage and use.^[27] This application leverages the solvent's ability to solvate organometallics without interfering in their reactivity, as demonstrated in the synthesis of pharmaceutical precursors like sulfonamides.^[28] In liquid-liquid extraction processes, dibutyl ether functions as a selective solvent for nonpolar organic compounds, including hydrocarbons, fats, and oils, owing to its low water solubility of approximately 0.11 g/L at 20°C.^[4] This property facilitates efficient partitioning of target solutes from aqueous phases, making it suitable for recovering nonpolar extracts in purification workflows. As a reaction medium, dibutyl ether supports Grignard reagent formations and subsequent alkylations, where its chemical stability under basic conditions is crucial. Early investigations confirmed its efficacy in Grignard syntheses, yielding comparable results to diethyl ether while offering greater thermal stability for elevated temperatures.^[29] The solvent's low reactivity with strong bases ensures minimal side reactions, enabling clean conversions in processes like the alkylation of carbonyl compounds.^[30] Key advantages of dibutyl ether include its high boiling point of 140°C, which allows for reflux operations without excessive volatility. Although it can form peroxides upon exposure to air, it is often considered safer than diethyl ether due to lower volatility, but peroxide testing is recommended. These traits are particularly beneficial in pharmaceutical intermediate synthesis, such as the production of heterocyclic compounds and aromatic derivatives, where high yields and process safety are prioritized.^[31]^[32]^[33]

Other applications

Dibutyl ether serves as an oxygenate additive in diesel fuel blends, enhancing combustion efficiency and reducing particulate emissions such as soot and carbon monoxide. Studies indicate that blending dibutyl ether with diesel can lower soot and CO emissions while slightly increasing NOx due to its oxygen content of 12.3% by weight.^[34]^[35] However, its adoption remains limited primarily due to higher production costs compared to conventional additives like methyl tert-butyl ether.^[36] As of 2024, ongoing research explores its potential in sustainable biofuel blends. In nuclear fuel reprocessing, dibutyl ether functions as an extractant for separating actinides, including uranium and thorium, from aqueous solutions in early solvent extraction processes. Historical investigations explored its use alongside tributyl phosphate for purifying uranium in nitrate media, leveraging its ability to form complexes with metal ions during reprocessing of spent fuel. This application highlights its role in specialized hydrometallurgical contexts, though modern processes favor more selective organophosphorus extractants.^[37] Dibutyl ether finds minor application in perfumery and flavor formulations owing to its characteristic fruity, sweet, and alcoholic odor profile, with fruity notes comprising about 76% of its sensory attributes. Its ethereal, winey undertones contribute to natural fruity accords in low concentrations, complying with IFRA standards for use in fine fragrances and other cosmetic products without concentration restrictions.^[38] Although less common than traditional peroxides, dibutyl ether participates in certain free-radical polymerization processes as a component in initiator systems, particularly when complexed with Lewis acids like AlCl3 to promote cationic initiation in non-polar solvents. For instance, AlCl3/dibutyl ether complexes have been employed to polymerize isobutylene, yielding polyisobutylene with controlled vinyl end-groups, though such systems are niche compared to standard radical initiators.^[39] Global production of dibutyl ether is modest, primarily directed toward specialty chemical applications rather than bulk solvents.

Safety and toxicity

Health hazards

Dibutyl ether demonstrates low acute toxicity overall, with an oral LD50 of 7,400 mg/kg in rats, indicating it is not highly lethal via ingestion.^[5] However, it acts as an irritant to the skin, eyes, and respiratory tract upon contact or exposure.^[40] Direct skin contact may cause mild irritation, while eye exposure leads to moderate irritation, potentially resulting in redness and discomfort.^[5] Respiratory exposure irritates the nose, throat, and lungs, causing coughing and wheezing.^[40] Inhalation of dibutyl ether vapors poses risks of dizziness, headache, and lightheadedness at elevated concentrations, with narcotic effects akin to those of other ethers, including weakness and potential unconsciousness.^[41] The 4-hour LC50 for inhalation in rats is 21.6 mg/L, underscoring moderate inhalation toxicity.^[5] These effects are exacerbated by the compound's ability to be absorbed through the skin, amplifying systemic exposure during handling.^[40] Dibutyl ether can form explosive peroxides when exposed to air over time, particularly during prolonged storage or distillation without stabilizers, leading to risks of violent decomposition or explosion upon disturbance.^[41] Chronic exposure data are limited, with no specific animal studies demonstrating reproductive toxicity; however, repeated inhalation or skin contact may contribute to ongoing irritation and central nervous system effects based on acute profiles of similar ethers.^[14] No specific occupational exposure limits, such as a TLV from the American Conference of Governmental Industrial Hygienists (ACGIH) or PEL from OSHA, have been established.^[42] Appropriate handling requires good ventilation to minimize airborne concentrations, along with personal protective equipment such as chemical-resistant gloves (e.g., Viton or nitrile), safety goggles, and flame-retardant clothing.^[5] In case of inhalation or ingestion, immediate medical attention is essential: move affected individuals to fresh air, provide oxygen if breathing is difficult, and do not induce vomiting for ingestion; for skin or eye contact, rinse thoroughly with water for at least 15 minutes and seek medical evaluation if irritation persists.^[8]

Environmental impact

Dibutyl ether demonstrates low bioaccumulation potential in aquatic organisms, characterized by an octanol-water partition coefficient (log Kow) of 3.35 and bioconcentration factors (BCF) ranging from 47 to 83, as measured in fish according to OECD Test Guideline 305C.^[14]^[43] These values indicate minimal tendency to concentrate in the food chain, classifying it as having low environmental persistence through biomagnification.^[42] In terms of biodegradability, dibutyl ether is not considered readily biodegradable under standard aerobic conditions, with only 5% degradation observed over 28 days in an OECD TG 301 D closed bottle test.^[14] However, it undergoes atmospheric degradation via reaction with photochemically produced hydroxyl radicals, contributing to its overall environmental fate.^[42] Aquatic toxicity assessments reveal a moderate hazard to water organisms, exemplified by an acute LC50 of 32.3 mg/L for fathead minnow (Pimephales promelas) in a 96-hour flow-through test following OECD Test Guideline 203.^[44] This aligns with its classification as harmful to aquatic life with long-lasting effects (H412).^[45] Dibutyl ether is registered under the EU REACH regulation as a substance of low concern, not meeting the criteria for persistent, bioaccumulative, and toxic (PBT) or very persistent and very bioaccumulative (vPvB) classification per Annex XIII. As a volatile organic compound (VOC) with 100% VOC content, its emissions are subject to regulation under air quality directives, including the Industrial Emissions Directive, to mitigate atmospheric contributions to smog formation. Waste management practices for dibutyl ether emphasize incineration in controlled industrial facilities to ensure complete combustion and minimize releases, while recycling is feasible for uncontaminated streams through distillation processes.^[9] Spill cleanup involves the use of inert absorbents to contain the liquid, followed by collection and disposal as hazardous waste to prevent soil and water contamination.

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