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Magic acid

Magic acid is a superacid composed of a 1:1 molar mixture of fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), with the overall formula F₆HO₃SSb and a molecular weight of 316.82 g/mol.^[1] Developed in the 1960s by Nobel laureate George A. Olah and his team at Case Western Reserve University, it earned its name from a striking demonstration in which a Christmas candle (made of paraffin wax) was dissolved in the acid at low temperature, forming a clear solution of the stable tert-butyl carbocation observable by NMR spectroscopy.^[2] This discovery highlighted its extraordinary ability to protonate even weakly basic hydrocarbons, which are typically inert to conventional acids.^[1] With a Hammett acidity function (H₀) of approximately -23, magic acid is about 10¹¹ times stronger than 100% sulfuric acid (H₂SO₄**, H₀ = -12), classifying it as a conjugate Brønsted-Lewis superacid system where SbF₅ acts as a Lewis acid to enhance proton donation. Its physical properties include a melting point of -89°C and a boiling point around 163°C, and it is highly viscous, fuming, and corrosive, requiring handling under inert conditions due to its reactivity with moisture and air. In chemical research, magic acid has been pivotal for generating and stabilizing elusive carbocations, such as the protonated methane ion (CH₅⁺) and polycondensed alkane species, enabling studies of electrophilic reactions and hydrogen exchange in alkanes that were previously inaccessible.^[1]^[2] These applications contributed to Olah's 1994 Nobel Prize in Chemistry for work on carbocation chemistry, underscoring magic acid's role in advancing organic synthesis and mechanistic understanding.^[2]

Discovery and History

Development of Superacids

The concept of superacids emerged in 1927 when James Bryant Conant, a chemist at Harvard University, coined the term to describe acid solutions exhibiting protonating power beyond that of conventional mineral acids, such as those capable of interacting with weak bases like carbonyl compounds. Collaborating with Norris F. Hall, Conant conducted pioneering studies on these superacid solutions using glacial acetic acid as a solvent, revealing their ability to maintain high acidity without the leveling effect of water. This work highlighted the need for non-aqueous media to explore extreme acidities, setting the stage for quantitative assessments of such systems. A key prerequisite for understanding superacidity is the Hammett acidity function, H₀, developed by Louis P. Hammett and A. J. Deyrup in 1932 to extend pH measurements to highly concentrated or non-aqueous strong acid solutions. Defined as H_0 = \mathrm{p}K_{\mathrm{BH^+}} + \log \frac{[\mathrm{B}]}{[\mathrm{BH^+}]}, where B is a neutral weak base indicator (e.g., a nitroaniline) and BH⁺ its protonated conjugate acid, H₀ quantifies proton activity based on indicator protonation equilibria rather than hydrogen ion concentration. For context, pure sulfuric acid achieves H₀ ≈ -12, establishing a benchmark; superacids are thus characterized by H₀ values below -12, enabling protonation of typically inert hydrocarbons and other weakly basic species.^[3] In the 1960s, Ronald J. Gillespie at McMaster University significantly advanced superacid development by seeking stable, highly acidic media to isolate and study elusive reactive species, particularly carbocations, which conventional solvents could not accommodate due to their leveling or reactivity.^[4] Focusing on fluorosulfuric acid (HSO₃F) combined with Lewis acids like antimony pentafluoride (SbF₅), Gillespie prepared initial mixtures in the early 1960s that achieved unprecedented acidities, as measured by the Hammett function.^[3] His publications, including determinations of H₀ for these systems, demonstrated acid strengths orders of magnitude greater than sulfuric acid, facilitating breakthroughs in studying short-lived intermediates and expanding the scope of acid-base chemistry.^[3] Gillespie collaborated with George A. Olah on superacid research, contributing to advancements in the field.

Naming and Experimental Milestones

The magic acid system, a conjugate Brønsted-Lewis superacid composed of fluorosulfuric acid and antimony pentafluoride, was developed in the 1960s by George A. Olah and his team at Case Western Reserve University as part of investigations into highly acidic media stronger than 100% sulfuric acid, building on earlier superacid concepts advanced by Gillespie.^[2] Independently and in collaboration, Olah explored similar fluorosulfuric acid-antimony pentafluoride mixtures in the early 1960s, applying them to organic chemistry and demonstrating their utility in stabilizing carbocations, work that underpinned his 1994 Nobel Prize in Chemistry for contributions to carbocation chemistry originating in that decade. Gillespie advanced the fundamental inorganic chemistry of such superacids.^[4] The name "magic acid" originated in Olah's laboratory around 1966, coined by postdoctoral fellow Joseph Lukas after an impromptu experiment following a Christmas party. Lukas placed remnants of a paraffin wax candle into a sample of the acid mixture, where it dissolved rapidly, yielding a clear solution that produced a sharp 1H-NMR spectrum characteristic of the tert-butyl carbocation (formed via extensive cleavage and isomerization of the long-chain paraffins to the stable tertiary species).^[2] This striking demonstration of the acid's ability to protonate and ionize seemingly inert hydrocarbons like wax inspired the "magical" moniker, highlighting its unprecedented reactivity. The observation not only popularized the system but also validated its use for spectroscopic studies of carbocations at low temperatures. A pivotal milestone came in 1968 when Olah and coworkers reported the protonation of methane in magic acid solution, observing the stable methanium ion (CH5+) as a key intermediate via hydrogen-deuterium exchange and polycondensation studies monitored by NMR. This occurred at 140°C under atmospheric pressure, marking the first direct evidence of alkane protonation to form a pentacoordinate carbonium ion and opening new avenues in the chemistry of saturated hydrocarbons previously considered unreactive.^[1] The CH5+ species, long hypothesized but elusive, confirmed the superacid's extreme protonating power and facilitated subsequent research into higher alkane transformations.^[1]

Composition and Preparation

Chemical Components

Magic acid is primarily composed of fluorosulfuric acid (HSO_3F) and antimony pentafluoride (SbF_5), mixed in a typical 1:1 molar ratio to form the complex HSO_3F \cdot SbF_5, which has a molar mass of 316.82 g/mol.^[5] Fluorosulfuric acid functions as the Brønsted acid component, capable of donating a proton due to its strong acidity, while antimony pentafluoride serves as the Lewis acid, enhancing the overall superacidic properties through its ability to accept electron pairs and coordinate with anions.^[6]^[7] The molecular structure of fluorosulfuric acid features a sulfur atom bonded to a hydroxyl group, two oxygen atoms, and a fluorine atom (HO-SO_2F), which contributes to its role in proton transfer within the mixture. In its pure form, antimony pentafluoride is a viscous, colorless liquid with a polymeric structure involving fluorine bridges between SbF_5 units, and it exhibits strong fluorinating capabilities that support the stabilization of carbocations in superacid media.^[8] The 1:1 ratio represents the standard composition for magic acid, though variations with different ratios have been reported to adjust acidity.^[6]

Synthesis Procedure

Magic acid is typically prepared by slowly adding antimony pentafluoride (SbF₅) to fluorosulfuric acid (HSO₃F) in a 1:1 molar ratio while maintaining anhydrous conditions to form the superacidic mixture. This standard procedure enhances the acidity through the formation of a conjugate Brønsted-Lewis acid system, with the reaction carried out at low temperatures, such as -78 °C using an acetone-dry ice bath, to control the exothermic nature of the mixing process and ensure safety. The 1:1 composition is most common for general applications, though variations with higher SbF₅ content can be used in related superacid systems for greater acidity. Due to the extreme corrosiveness of the components, the synthesis requires specialized equipment such as Teflon-lined or glass-lined vessels, often using a Schlenk tube or similar apparatus fitted with a magnetic stirrer for controlled addition and mixing. The addition of SbF₅ must be gradual under constant stirring to ensure uniform reaction and prevent localized overheating. An inert atmosphere, typically dry nitrogen, is essential throughout the process to exclude moisture, as even trace water can cause hydrolysis and violent fuming. The reaction presents several challenges, including significant heat evolution and the production of fumes, necessitating robust ventilation and cooling systems. Temperature control during preparation and use is important for safety and the stability of reactive intermediates. Yields of the preparation are generally quantitative, reflecting the straightforward mixing nature of the process, though purification via distillation or recrystallization is impractical due to the high reactivity. Instead, purity is evaluated through spectroscopic methods such as ¹H, ¹³C, or ¹⁹F NMR, or by measuring conductivity, ensuring the absence of impurities like unreacted components or hydrolysis products.

Properties

Molecular Structure and Equilibria

Magic acid exhibits a complex molecular structure arising from the interaction between fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), forming a conjugate Brønsted-Lewis superacid system rather than a discrete molecular compound. The primary bonding mechanism involves SbF₅ acting as a strong Lewis acid that accepts a fluoride ion from HSO₃F, promoting protonation and generating ionic species such as the fluorodihydroxyoxosulfonium cation (H₂SO₃F⁺) paired with complex fluoroantimonate anions like SbF₅(SO₃F)⁻ or SbF₆⁻. This fluoride abstraction enhances charge delocalization in the anion, stabilizing the protonated cation and increasing the system's overall acidity.^[9]^[10] The system is dominated by dynamic equilibria, with the key ionization represented as:

$2 \ce{HSO3F} + \ce{SbF5} \rightleftharpoons \ce{H2SO3F+} + \ce{SbF5(SO3F)-}

At low SbF₅ concentrations (e.g., below 25 mol%), this ionic equilibrium (Equilibrium I) predominates, comprising approximately 80% of the mixture, featuring H₂SO₃F⁺ and SbF₅(SO₃F)⁻. A minor component (about 20%) exists as Equilibrium II, involving the molecular adduct HSO₃F–SbF₅, which can further protonate to related ionic forms. These proportions reflect the balance between ionic dissociation and adduct formation in dilute conditions.^[9]^[11] Spectroscopic studies provide direct evidence for these structures and bonding interactions. Raman spectroscopy reveals characteristic vibrational modes, such as Sb–F stretches around 600–700 cm⁻¹ and S–O modes near 1000 cm⁻¹, indicative of fluoride bridging between SbF₅ units and the SO₃F group in the anions. Nuclear magnetic resonance (NMR) data further confirm the species: ¹⁹F NMR shows distinct signals for SbF₆⁻ (around -130 ppm) and more complex anions like FSO₃SbF₆⁻ (shifted by 10–20 ppm due to bridging), while ¹H NMR detects the delocalized proton in H₂SO₃F⁺ at approximately 10 ppm, with broadening from rapid exchange. These observations highlight proton delocalization across oxygen atoms in the cation and dynamic fluoride coordination in the anion.^[9]^[12] The equilibria shift with variations in SbF₅ concentration and temperature, influencing the structural composition. Increasing SbF₅ beyond 50 mol% favors formation of polynuclear anions, such as Sb₂F₁₁(SO₃F)⁻ or Sb₃F₁₆(SO₃F)⁻, through further fluoride bridging and polymerization of SbF₅ units, enhancing ionization. Temperature dependence is evident in NMR studies, where cooling to -70°C or lower slows proton exchange (reducing linewidths) and stabilizes transient species, allowing clear resolution of ionic forms that equilibrate rapidly at room temperature.^[9]^[12]

Acidity and Strength Metrics

The acidity of magic acid, a prototypical superacid, is most commonly measured using the Hammett acidity function (H_0), which provides a quantitative scale for the protonating ability of highly concentrated acid media beyond the limitations of the pH scale. This function is determined experimentally by observing the protonation equilibrium of weak base indicators in the acid solution. For magic acid (a 1:1 mixture of fluorosulfuric acid and antimony pentafluoride), the H_0 value is typically around -23, reflecting its capacity to protonate bases that are negligibly basic in conventional acids. In formulations with excess SbF5, the acidity increases further, achieving H_0 values up to approximately -25, as the additional Lewis acid component enhances proton transfer efficiency. The Hammett acidity function is defined by the equation:

H_0 = \mathrm{p}K(\mathrm{BH}^+) + \log \left( \frac{[\mathrm{B}]}{[\mathrm{BH}^+]} \right)

where \mathrm{B} represents the neutral form of a weak base indicator, \mathrm{BH}^+ its protonated conjugate acid, and \mathrm{p}K(\mathrm{BH}^+) the negative logarithm of the acid dissociation constant of \mathrm{BH}^+ in water. This logarithmic scale allows direct comparison of acid strengths; for instance, magic acid with H_0 \approx -23 is approximately $10^{11} times stronger than 100% sulfuric acid (H_0 = -12) and $10^{10} times stronger than perchloric acid (H_0 = -13), as each unit decrease in H_0 corresponds to a tenfold increase in protonating power. Measurements for magic acid employ indicators such as substituted nitroanilines (e.g., 2,4-dinitroaniline or p-nitroaniline derivatives), whose protonation ratios are determined spectroscopically in the superacid medium. This exceptional acidity stems from magic acid's ability to protonate extremely weak bases, such as alkanes or alkenes, and to stabilize elusive carbocations through the low nucleophilicity of its conjugate base, which minimizes back-reaction and ion-pairing. The structural features contributing to this low nucleophilicity, including the weakly coordinating nature of fluorosulfonate and pentafluoroantimonate anions, underpin the observed metrics but are detailed in discussions of molecular equilibria.

Applications

Carbocation Stabilization

Magic acid, a superacid composed of fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), plays a pivotal role in carbocation chemistry by providing a highly acidic medium that delivers protons (H⁺) while generating weakly coordinating anions such as SbF₆⁻, which minimize nucleophilic solvation and thereby stabilize otherwise fleeting carbocations.^[2] This low nucleophilicity of the counterions prevents rapid recombination or rearrangement, allowing carbocations to persist long enough for direct spectroscopic observation.^[13] Key examples of stabilized species include trivalent carbocations such as the tert-butyl cation ((CH₃)₃C⁺), generated from the protonation of isobutane in magic acid solutions at low temperatures.^[2] The tert-butyl cation exhibits characteristic ¹H NMR signals with methyl protons deshielded to approximately 4.3 ppm and a ¹³C NMR shift at 335.2 ppm, confirming its planar sp²-hybridized structure.^[2] Similarly, the ethyl cation (CH₃CH₂⁺) has been isolated and characterized, demonstrating stabilization through hyperconjugation in these superacidic conditions.^[2] Penta-coordinate (nonclassical) carbocations, such as the 2-norbornyl cation, are also stabilized, featuring bridged structures with three-center two-electron bonds that delocalize the positive charge.^[13] George A. Olah's pioneering work in the 1960s involved the first direct NMR observation of stable alkyl carbocations using magic acid, including the ethyl cation and various bridged ions, which resolved long-standing debates on carbocation structures and mechanisms.^[2] These advancements culminated in Olah's 1994 Nobel Prize in Chemistry for contributions to carbocation chemistry.^[13] Characterization relies on cryogenic techniques, often at temperatures around -60°C to -78°C or lower (down to -159°C in specialized solvents like SO₂ClF/SO₂F₂), employing ¹H and ¹³C NMR spectroscopy alongside IR and Raman methods to probe structures without decomposition.^[2] These conditions ensure the carbocations remain observable as long-lived species, facilitating detailed studies of their electronic and geometric properties.^[13]

Hydrocarbon Protonation and Reactions

Magic acid, a superacid composed of fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), enables the protonation of alkanes through the general mechanism RH + H⁺ → RH₂⁺, where the C-H bond is activated to form protonated species such as carbonium ions.^[1] This process involves two-electron, three-center (2e–3c) bonding, stabilizing pentacoordinate intermediates and allowing direct observation of otherwise elusive hydrocarbon ions.^[2] For methane, protonation yields the CH₅⁺ ion, while ethane forms C₂H₇⁺, with the latter preferring a C-C protonated structure due to charge delocalization.^[1] These reactions occur under controlled low-temperature conditions to prevent rapid decomposition, providing the first direct spectroscopic evidence of alkane protonation and fundamentally advancing the understanding of C-H bond activation.^[1] Experimental studies typically employ sealed NMR tubes to monitor the protonation and subsequent transformations, with temperatures ranging from -78°C to -160°C for primary alkanes to ensure stability of the RH₂⁺ species.^[9] Proton NMR spectra reveal deshielded protons in these ions, confirming their formation, while ¹³C NMR provides structural insights into fluxional behaviors, such as degenerate rearrangements in CH₅⁺.^[2] Hydrogen-deuterium exchange rates, for instance, reach approximately 3.2 × 10⁻⁴ s⁻¹ for methane in magic acid, serving as a diagnostic for protonation equilibrium.^[9] These conditions highlight the reversible nature of C-H protolysis, where the superacid's extreme strength (H₀ ≈ -23) overcomes the weak basicity of alkanes. Beyond initial protonation, alkanes undergo dynamic reactions including isomerization and cracking. Isomerization proceeds via hydride or alkyl 1,2-shifts in the protonated intermediates, often involving protonated cyclopropane structures, leading to more stable carbocation rearrangements.^[9] For neopentane ((CH₃)₄C), protonation facilitates conversion to the tert-pentyl cation ((CH₃)₂C⁺CH₂CH₃) through C-C bond cleavage and skeletal reorganization, exemplifying β-scission pathways.^[9] Cracking involves protolytic fragmentation of C-C bonds, yielding smaller carbenium ions under thermodynamic control at longer contact times or slightly elevated temperatures (e.g., +25°C).^[2] Additionally, polycondensation accompanies these processes in methane and higher alkanes, forming oligomeric species via successive protonations and eliminations.^[1] These reactions demonstrate magic acid's role in mimicking catalytic hydrocarbon transformations under ionic conditions, with high selectivity toward tertiary cations.^[9]

Catalytic Processes

Magic acid serves as a highly effective catalyst in the protolytic cleavage-rearrangement of tertiary alkyl hydroperoxides, enabling the transformation of these compounds under mild conditions. In particular, tert-butyl hydroperoxide undergoes cleavage in magic acid to yield acetone and methanol as primary products. The mechanism initiates with protonation of the O-O bond in the hydroperoxide, facilitating heterolytic cleavage and subsequent 1,2-methyl migration from the tertiary carbon to the adjacent oxygen, resulting in the formation of protonated acetone and neutral methanol. This reaction proceeds efficiently at low temperatures, typically around -78°C in sulfolane or sulfur dioxide solvents, demonstrating the superacid's ability to stabilize reactive intermediates without requiring harsh oxidants.^[14] A notable application involves magic acid's catalysis of alkane oxygenation using ozone, which allows selective functionalization of saturated hydrocarbons that are otherwise inert under standard conditions. For example, adamantane is converted to 1-adamantanol with high selectivity at the tertiary carbon position. The process employs stoichiometric amounts of ozone in superacid (such as HF-SbF₅) diluted with sulfur dioxide at low temperatures such as -78°C, achieving yields up to 80% for the desired alcohols. The mechanism proceeds via protonated ozone or Criegee-type intermediates, where the electrophilic oxygen species inserts into C-H bonds, forming hydroxyalkyl cations that are quenched to alcohols upon workup; a simplified representation is Alkane + O₃ → oxygenated products (e.g., R₃C-H + O₃ → R₃C-OH).^[15] These catalytic processes highlight magic acid's utility in synthetic organic chemistry by enabling oxygenation and rearrangement reactions under ambient conditions that would otherwise demand elevated temperatures or metal-based catalysts. The selectivity for tertiary sites in alkanes and the clean cleavage of hydroperoxides underscore its role in developing efficient routes to oxygenated fine chemicals, avoiding over-oxidation common in conventional methods.^[14]

Safety and Environmental Considerations

Health and Handling Hazards

Magic acid, a mixture of fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), presents extreme physical hazards due to its highly corrosive nature as a viscous, fuming liquid. Direct contact with skin causes immediate and severe chemical burns that penetrate deeply, leading to tissue necrosis and potential systemic fluoride poisoning from released hydrofluoric acid (HF).^[16]^[17] Additionally, it emits toxic vapors of HF and sulfur trioxide (SO₃) upon exposure to moisture or air, which can rapidly hydrolyze the acid and exacerbate risks in confined spaces.^[18]^[19] Exposure routes to magic acid result in profound health effects, with inhalation causing severe irritation of the respiratory tract, pulmonary edema, throat swelling, and potential asphyxiation or respiratory failure.^[20]^[21] Ingestion is invariably fatal, inducing immediate gastrointestinal corrosion, shock, and cardiovascular collapse due to the combined effects of HF and antimony toxicity.^[22]^[17] Eye contact leads to irreversible damage, including corneal ulceration and blindness from the acid's aggressive penetration and the fluoride ion's affinity for calcium in ocular tissues.^[16]^[18] Specific toxicity data for magic acid itself is limited, with no established LD50 values reported as of 2025; however, its hazards are analogous to those of HF, which has an acute oral LD50 in rats of approximately 120-250 mg/kg but can be lethal at doses as low as 20 mg/kg due to delayed systemic effects like hypocalcemia and cardiac arrhythmias.^[23] Antimony compounds in the mixture, such as SbF₅, contribute additional risks, including acute poisoning symptoms like nausea, vomiting, and convulsions. While trivalent antimony compounds are classified as probably carcinogenic to humans (IARC Group 2A) based on limited evidence of lung cancer in exposed workers, SbF₅ contains pentavalent antimony and is not specifically classified under this category.^[24]^[25] Safe handling of magic acid requires stringent protocols to mitigate these risks, mandating use exclusively in a well-ventilated chemical fume hood calibrated within the past 12 months, with a buddy system for monitoring.^[18]^[26] Personal protective equipment (PPE) must include chemical-resistant gloves (e.g., thick Viton or neoprene, 10-20 mil thickness), tight-fitting splash goggles, a full face shield (minimum 20 cm), a laboratory apron or coat made of acid-resistant material, closed-toe shoes, long pants, and a full-face respirator equipped with appropriate cartridges for acid gases and particulates.^[18]^[22] For spills or decontamination, neutralization should employ dilute weak bases such as sodium bicarbonate (NaHCO₃) or calcium hydroxide (Ca(OH)₂), applied cautiously from the spill's periphery inward, followed by pH testing to ensure neutrality (6-8) and thorough rinsing with water; all waste must be treated as hazardous.^[18] In case of exposure, immediate medical attention is critical, with calcium gluconate gel recommended for HF-related skin or eye contact to bind free fluoride ions.^[18] Due to the absence of mixture-specific safety data sheets as of 2025, handling protocols should be based on the known hazards of its components, HSO₃F and SbF₅.

Environmental Impact

Magic acid, composed of fluorosulfuric acid (HSO₃F) and antimony pentafluoride (SbF₅), poses significant risks to aquatic ecosystems primarily through its components' hydrolysis products and metal ions. Upon release into water, HSO₃F hydrolyzes rapidly and violently to form hydrogen fluoride (HF) and sulfuric acid, both of which are highly toxic to aquatic organisms; HF disrupts ion balance and causes acute mortality in fish and invertebrates at low concentrations, while sulfate can exacerbate acidification in sensitive habitats.^[27]^[28] SbF₅ dissociates to release antimony ions, which are toxic to algae, crustaceans, and fish, with EPA ambient water quality criteria setting a chronic freshwater limit of 74 µg/L to protect aquatic life.^[29] Additionally, antimony exhibits bioaccumulation potential in aquatic food chains, concentrating in primary producers and biomagnifying through higher trophic levels, leading to long-term adverse effects on ecosystem health.^[30] The persistence of magic acid in the environment contributes to prolonged contamination risks from its antimony component. Antimony compounds from SbF₅ are recalcitrant, resisting microbial degradation and leading to long-term soil accumulation from spills.^[31] This durability raises concerns for chronic groundwater pollution, as antimony can leach into aquifers over extended periods, potentially contaminating drinking water sources in accident-prone areas.^[32] Under U.S. Environmental Protection Agency (EPA) regulations, magic acid qualifies as hazardous waste due to its corrosivity (D002 code) and reactivity (D003 for SbF₅), with antimony wastes also falling under specific listings like K021 for spent catalysts.^[8]^[33] Given its primary laboratory use rather than large-scale industrial application, no specific discharge limits exist, but general prohibitions on hazardous waste releases apply, emphasizing proper containment and disposal to prevent environmental entry.^[34] Current knowledge on magic acid's environmental fate remains limited, with few dedicated studies post-2020; most research focuses on component toxicity rather than holistic mixture behavior, highlighting gaps in understanding long-term transport, transformation, and ecological interactions in real-world spill scenarios.^[35]

References

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[33]
[PDF] EPA HAZARDOUS WASTE CODES
EPA codes include D001 for ignitable waste, D002 for corrosive waste, D003 for reactive waste, and F001 for spent halogenated solvents used in degreasing.
[34]
Fate and toxicity of spilled chemicals in groundwater and soil ... - NIH
Once spilled, most hydrofluoric acid vaporizes; however, some remains in the soil environment and can negatively impact soil and groundwater quality [13].