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Acetylacetone

Acetylacetone structure

Acetylacetone 

structure
  • CAS No:

    123-54-6

  • Formula:

    C5H8O2

  • Chemical Name:

    Acetylacetone

  • Synonyms:

    2,4-Pentanedione;Acetylacetone;Diacetylmethane;2-Propanone,acetyl-;2,4-Dioxopentane;Acetoacetone;2,4-Pentadione;ACAC;Pentan-2,4-dione;NSC 139614;NSC 2679;NSC 2927;NSC 52336;NSC 54069;NSC 5575;NSC 77075;NSC 78795;2,4-Pentandione;81235-32-7

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Acetylacetone is an organic compound that exists in two tautomeric forms that interconvert rapidly and are treated as a single compound in most applications. Although the compound is formally named as the diketone form, pentane-2,4-dione, the enol form forms a substantial component of the material and is actually the favored form in many solvents. It is a colourless liquid that is a precursor to acetylacetonate (acac), a common bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.


Pentane-2,4-dione appears as a colorless or yellow colored liquid. Less dense than water. Vapors are heavier than air. Used as a solvent in paints and varnishes.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.|A colorless or yellow colored liquid.


Pentane-2,4-dione appears as a colorless or yellow colored liquid. Less dense than water. Vapors are heavier than air. Used as a solvent in paints and varnishes.|Acetylacetone is a beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups. It is a conjugate acid of an acetylacetonate.

Acetylacetone Basic Attributes

100.11600

100.12

204-634-0

46R950BP4J

0533

5575

2310

DTXSID4021979

Colorless or slightly yellow liquid|Mobile, colorless or yellowish liquid; when cooled, solidifies to lustrous, pearly spangles. The liquid is affected by light, turning brown and forming resins.

2914190090

Characteristics

34.14000

0.55450

Pentane-2,4-dione appears as a colorless or yellow colored liquid. Less dense than water. Vapors are heavier than air. Used as a solvent in paints and varnishes.

0.9721 g/cm3 @ Temp: 25 °C

-23 °C

140 °C

35.5ºC

1.451-1.453

H2O: 16 g/100 mL (20 ºC)

2-8ºC

6 mm Hg ( 20 °C)

3.5 (vs air)

Lower flammable limit in air: 2.4%; Upper flammable limit in air: 11.6%

vol% in air: 2.41.6

Pleasant odor

Henry's Law constant = 2.35X10-6 atm-cu m/mol at 25 °C (est)

1.15e-12 cm3/molecule*sec

pKa = 8.93

Specific gravity: 0.9753 at 20 °C/20 °C|Heat of solution: -11.5 Btu/lg = -6.4 cal/g; Ratio of specific heats of vapor (gas) = 1.072 (est)|The enol form predominates (70-90%) in the pure liquid state, the vapor state, and when dissolved in most organic solvents. In water, only 12% of the enol is present at equilibrium|Hydroxyl radical reaction rate constant = 9.05X10-11 cu cm/molec-sec at 25 °C (enol-form)

Highly flammable. Soluble in water.

Ketones

Highly Flammable

Ketones, such as PENTANE-2,4-DIONE, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. May dissolve plastics (USCG, 1999).

644 °F (USCG, 1999)|644 °F (340 °C)|340 °C

-11,070 Btu/lb = -6,150 cal/g = -257X10+5 J/kg

The vapour is heavier than air.

36.55 kJ/mol at 101.3 kPa

Safety Information

III

3

UN 2310

1

R10; R22

S21-S23-S24/25

SA1925000

Xn

Fireproof. Separated from strong oxidants. Keep in the dark.

Stable under recommended storage conditions.

P261-P280-P311

H226-H302-H311-H331

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Product: Contact a licensed professional waste disposal service to dispose of this material. Offer surplus and non-recyclable solutions to a licensed disposal company. Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable; Contaminated packaging: Dispose of as unused product.|Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Incompatible materials: Strong oxidizing agents, reducing agents, strong bases, metals.|Incompatibilities: Oxidizing material, bases, reducing agents, halogens, aliphatic amines, alkanolamines, organic acids, isocyanates. Light may cause polymerization.

2,4-Pentanedione is an indirect food additive for use only as a component of adhesives.

UN 2310

P261; P280; P311

Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back. (USCG, 1999)|Flammable. Above 34 °C explosive vapour/air mixtures may be formed.|Flammable - 3rd degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, and P501|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 1141 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P311, P312, P321, P322, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P311, P312, P321, P322, P330, P337+P313, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. SMALL SPILL: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Safety glasses; eye bath and safety shower; air-supplied mask for concentrations above 2% (USCG, 1999)|Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. Flame retardant antistatic protective clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Wear protective gloves and clothing to prevent any reasonable probability of skin contact. ... All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. ... Wear splash-proof chemical goggles and face shield unless full face-piece respiratory protection is worn.

Flammable liquid when exposed to heat or flame.|Moderate fire risk.

Explosive limits , vol% in air: 2.4-11.6

Suitable extinguishing media: Dry powder, dry sand. Unsuitable extinguishing media: Do NOT use water jet.|Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Use water spray to cool unopened containers.|Use dry chemical, carbon dioxide, alcohol foam, or polymer foam extinguishers. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.|To fight fire, use alcohol foam, /carbon dioxide/, or dry chemical.

Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with non-combustible absorbent material, (e.g. sand, earth, diatomaceous earth, vermiculite) and place in container for disposal according to local/national regulations.|Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the buildup of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.|Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|For more Preventive Measures (Complete) data for Acetyl acetone (7 total), please visit the HSDB record page.

/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind, uphill and/or upstream. Ventilate closed spaces before entering.|/GUIDE 131 FLAMMABLE LIQUIDS - TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for Acetyl acetone (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. Pentane-2,4-dione is included on the dangerous goods list.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. Pentane-2,4-dione is included on the dangerous goods list.

Mild irritant to skin, mucous membranes.|A skin and severe eye irritant.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Ventilation. Collect leaking liquid in sealable containers. Wash away remainder with plenty of water.

Fireproof. Separated from strong oxidants. Keep in the dark.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system. This may result in tissue lesions.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the thymus, lungs, central nervous system and nasal passage.

NO open flames, NO sparks and NO smoking. Above 34 °C use a closed system, ventilation and explosion-proof electrical equipment.

STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or face shield.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Acetyl acetone was identified, not quantified in ozone treated sludge press liquors from a waste water treatment facility in Kent, England(1). The compound was identified in an odor profiling study of a confined animal (swine) feeding operation in north western Texas. It was not identified as a major odorant from a beef operation(2).

Acetyl acetone was found at 6% weight/weight in one of 29 different types of printing inks(1). The compound has been identified in tobacco and tobacco substitute smoke(2).

Toxicity

IDENTIFICATION AND USE: Acetyl acetone is a colorless or slightly yellow liquid. It forms organometallic complexes which are used as gasoline additives, lubricant additives, driers for varnishes and printer's inks. HUMAN STUDIES: Acetly acetone (2 to 14 ppm) was reported to produce nausea and headaches in several persons. A case was reported involving an individual who had developed contact dermatitis to Cu(II)-acetyl acetonate and who also showed a cross reaction to acetyl acetone. The skin sensitizing properties of acetyl acetate were examined in a human patch test. Of the 12 persons tested three showed no reaction, seven doubtful, and two had a positive reaction after an exposure period of 24 hr. No skin reactions were evident after 48 and 72 hr, respectively. The results observed in the human patch test were interpreted as an irritating rather than a sensitizing effect. ANIMAL STUDIES: Acetyl acetone was not irritating to the skin of rabbits. In a rabbits eye irritation test, exposure to acetyl acetone resulted in minor transient irritation with no corneal involvement. After oral administration to rats, signs of toxicity were characterized by sluggishness, tremors, kyphosis, lacrimation, unsteady gait, comatose appearance and prostration. In another oral study, doses given by gavage to rats were 0, 100, 500 and 1,000 mg/kg bw given for 1 to 15 days in 1 to 11 applications. In the highest dose group all animals died within 1 hour after dosing. In the 500 mg/kg bw group 3/5 animals died and 2/5 were sacrificed due to poor condition after four applications. Various substance related systemic effects were observable in this dose group such as distended bladder, congested lungs, clouding of cornea, thymic necrosis, hepatocyte swelling and congestion, nephrosis, lymphadenitis of mesenteric lymph nodes and inflammation of the heart. After inhalation in rats (4 hr; 628, 919, 1231 and 1508 ppm) mortalities were observed in animals of the two highest dose groups. Signs of toxicity included reduced reflexes, respiratory difficulties, tremor as well as periocular, perioral and perinasal wetness and encrustation. Acetyl acetate was neurotoxic in rats. In rat developmental test reduced fetal body weight per litter was seen at 398 ppm and 202 ppm. Partial fetal atelectasis was increased at 398 ppm, and the increased incidence of 17 skeletal variants (out of 79 observed) indicated a consistent pattern of fetotoxicity at 398 ppm. Acetylacetone demonstrated a strong mutagenic effect on Salmonella typhimurium (TA-104). In Chinese hamster ovary cells acetyl acetate produced a statistically significant increase in the number of sister chromatid exchanges per cell in the presence and absence of a metabolic activation system.

When 2,4-pentanedione was incubated with yeast cells, no chromosome loss occurred even at a concentration of 1.96% (v/v) and cold shock, but the addition of propionitrile to the incubation mixture stimulated chromosomal loss.|... Acetylacetone inhibited the mutagenicity of 2-naphthohydroxamic acid.

LC50 Rat inhalation 1000 ppm/4 hr|LD50 Rat (male) oral 760 mg/kg|LD50 Rat (female) oral 570 mg/kg|LD50 Rat oral 1000 mg/kg|For more Non-Human Toxicity Values (Complete) data for Acetyl acetone (13 total), please visit the HSDB record page.

Acetyl acetone's production and use as gasoline additives, lubricant additives, driers for varnishes and printer inks, and dyes(1) may result in its release to the environment through various waste streams(SRC). Acetyl acetone's former use as a fungicide(1), bactericide(2), wood preservative(2) and insecticide(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.40(2) and a regression-derived equation(3), indicates that acetyl acetone is expected to have very high mobility in soil(SRC). Volatilization of acetyl acetone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.96 mm Hg(4), and water solubility, 166,000 mg/L(5). Acetyl acetone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 4 weeks(6), suggesting that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 34(SRC), determined from a log Kow of 0.40(2) and a regression-derived equation(3), indicates that acetyl acetone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.96 mm Hg(5), and water solubility, 166,000 mg/L(6). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 16 days and 120 days, respectively(SRC). The aquatic oxidation rate for acetyl acetone has been experimentally determined to be 9.9X10-9 L/mol-s at pH 6.4(7). Based on this rate and a hydroxyl radical concentration of 1X10-17 mol/L in water under continuous sunlight(8), the half-life for the aquatic oxidation of acetyl acetone can be estimated to be 81 days(SRC). According to a classification scheme(9), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 83% of the Theoretical BOD was reached in 4 weeks(10), suggesting that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetyl acetone, which has a vapor pressure of 2.96 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetyl acetone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 days(SRC), calculated from its rate constant of 9.05X10-11 cu cm/molecule-sec at 25 °C(3). Acetyl acetone absorbs UV light at wavelengths >314 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of acetyl acetone (enol form) with photochemically-produced hydroxyl radicals has been measured as 9.05X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 22 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The aquatic oxidation rate for acetyl acetone has been experimentally determined to be 9.9X10-9 L/mol-s at pH 6.4(2). Based on this rate and a hydroxyl radical concentration of 1X10-17 mol/L in water under continuous sunlight(3), the half-life for the aquatic oxidation of acetyl acetone can be estimated to be 81 days(SRC). Acetyl acetone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Acetyl acetone absorbs UV light at wavelengths >314 nm(5) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for acetyl acetone(SRC), using a log Kow of 0.40(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of acetyl acetone is estimated as 34(SRC), using a log Kow of 0.40(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that acetyl acetone is expected to have very high mobility in soil(SRC).

The Henry's Law constant for acetyl acetone is estimated as 2.4X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 2.96 mm Hg(1), and water solubility, 166,000 mg/L(2). This Henry's Law constant indicates that acetyl acetone is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 16 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 120 days(SRC). Acetyl acetone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of acetyl acetone from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).

Acetyl acetone has been identified, not quantified in chicken(1).

According to the 2016 TSCA Inventory Update Reporting data, 12 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of acetyl acetone in the United States may be as low as 10 workers and as high as 500 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 6,173 workers (1,577 of these are female) are potentially exposed to acetyl acetone in the US(1). Occupational exposure to acetyl acetone may occur through inhalation and dermal contact with this compound at workplaces where acetyl acetone is produced or used. Limited monitoring data indicate that the general population may be exposed to acetyl acetone via use of tobacco products and via inhalation in localized areas near confined animal feeding operations(SRC).

Drug Information

2,4-Pentanedione (2,4-PD; CAS No. 123-54-6) ... was investigated for its comparative pharmacokinetics in male Fischer 344 rats by a single intravenous (i.v.) injection of (4.3, 43, 148.5, and 430 mg/kg), or a 6-hr nose-only inhalation exposure (400 ppm) to (14)C-2,4-PD. For the i.v. route, the plasma concentration of (14)C-2,4-PD-derived radioactivity declined in a biexponential fashion. The overall form of the (14)C plasma concentration-time curves and derived pharmacokinetic parameters indicated that dose-linear kinetics occurred in the i.v. dose range 4.3-148.5 mg/kg, but not with 430 mg/kg. Metabolism of 2,4-PD was rapid to undetectable after 8 hr. (14)C-2,4-PD derived radioactivity was eliminated mainly as (14)CO2 and in urine. For the 4.3, 43 and 148.5 mg/kg doses (14)CO2 elimination was relatively constant (36.8, 38.8 and 42.3% in 48 hr samples respectively) and greater than urinary excretion (17.9, 14.3 and 29.6%; 48 hr specimens). At 430 mg/kg i.v. there was a reversal of the excretion pattern, with urine (14)C excretion (54.7%) becoming greater than that for (14)CO2 (27.3%). Excretion in expired volatiles and feces was small. Radiochromatograms of urine showed free 2,4-PD in the 12 hr sample, together with 7 other metabolites. Free 2,4-PD and 6 of the metabolites decreased or were not detectable in a 24 or 48 hr urine sample, but one peak (retention 7.9 min) increased progressively to become the major fraction (97%). Nose-only exposure to 400 ppm (14)C-2, 4-PD produced a mean decrease in breathing rate of 20.1%, which was constant and sustained throughout exposure, due to a lengthening of the expiratory phase of the respiratory cycle. (14)C-2,4-PD was rapidly absorbed during the first 3 hr of exposure, then began to plateau, but did not reach a steady state. Postexposure elimination of (14)C from plasma followed a biexponential form with a t1/2 for the terminal disposition phase of 30.72 hr. ... Postexposure, plasma unmetabolized 2,4-PD declined rapidly to undetectable concentrations by 12 hr. Radiolabel excretion was approximately equivalent in urine (37.6%) and expired (14)CO2 (36.3%). Urine radiochromatograms showed a minor 2,4-PD contaminant (0.6-5.9% over 48 hr), along with 7 other peaks probably representing metabolites. The major metabolite peak was at 7.8 min retention, increasing from 41.1% (12 hr) to 62.8% (48 hr). Immediately postexposure, radioactivity was present in all tissues examined, but on a concentration basis (microgram equiv/g) there was no preferential accumulation of (14)C in any tissue or organ. ...

The purity of the substance exceeds 99%. Known impurities are water (0.1%), hexane-2,5-dione (0.1%), acetic acid (0.05%) and isopropenyl acetate (0.03%).

Inhalation causes dizziness, headache, nausea, vomiting and loss of consciousness. Contact with liquid irritates eyes. (USCG, 1999)

INHALATION: remove to fresh air; if victim is not breathing, give artificial respiration and then oxygen; call a physician. EYES or SKIN: flush with water. (USCG, 1999)


Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

If /acetyl acetone/ gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention.|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Ketones and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . For contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Ketones and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ketones and related compounds/

/HUMAN EXPOSURE STUDIES/ The skin sensitizing properties of 2,4-pentanedione were examined in ... a human patch test consisting of 12 volunteers. In the patch test study with human volunteers no information was available concerning gender and health status as well as a possible allergic predisposition of the test persons. Of the 12 persons tested three of them showed no, seven doubtful and two a positive reaction after an exposure period of 24 hr. No skin reactions were evident after 48 and 72 hr, respectively. The results observed in the human patch test were interpreted as an irritating rather than a sensitizing effect and it was concluded ... that sensitization might occur more frequently due to prolonged and close skin contact of pads containing the substance|/SIGNS AND SYMPTOMS/ 2,4-Pentanedione (2 to 14 ppm) has been reported to produce nausea and headaches in several persons ... .|/CASE REPORTS/ ... A case /was reported/ involving an individual who had developed contact dermatitis to Cu(II)-acetyl acetonate and who also showed a cross reaction to 2,4-pentanedione.

2,4-pentanedione

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

Incoordination. Dizziness. Drowsiness. Headache. Laboured breathing. Nausea. Vomiting. Ataxia


MAY BE ABSORBED! Redness.


Redness. Pain.

Acetylacetone Use and Manufacturing

Methods of Manufacturing

2,4-Pentanedione is produced by thermal or metal-catalyzed rearrangement of isopropenyl acetate (obtained from acetone and ketene). Isopropenyl acetate vapor is fed at atmospheric pressure through a V2A steel tube with an inner temperature of 520 °C. The hot reaction gases are quenched, condensed, and cooled to 20 °C, whereby the gaseous byproducts carbon monoxide, carbon dioxide, methane, and ketene are separated. The product is purified by fractional distillation. Other industrially less important processes for the production of 2,4-pentanedione, include the Claisen ester condensation of ethyl acetate with acetone using sodium ethoxide as condensation agent and the acetylation of acetoacetic acid esters with acetic anhydride in the presence of magnesium salts.|Made by the action of sodium on ethyl acetate and acetone or by the action of anhydrous aluminum chloride on acetyl chloride in the presence of an inert solvent.|Condensation of acetone and acetic anhydride with a boron trifluoride catalyst; reaction of acetone and ethyl acetate in the presence of sodium ethoxide.

Uses

Acetylacetone is an organic compound that exists in two tautomeric forms that interconvert rapidly and are treated as a single compound in most applications. Although the compound is formally named as the diketone form, pentane-2,4-dione, the enol form forms a substantial component of the material and is actually the favored form in many solvents. It is a colourless liquid that is a precursor to acetylacetonate (acac), a common bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.


Adhesives and sealant chemicals


Paints and coatings

Production

1,000,000 - 10,000,000 lb|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 9.08X10+5 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3823]|Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2,4-Pentanedione:

Adhesive manufacturing|2,4-Pentanedione: ACTIVE|SP - indicates a substance that is identified in a proposed Significant New Use Rule.

Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]|Fire Hazards -> Flammable - 3rd degree

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, isothermal Capillary DB-5 786.6 130. isothermal 60. m/0.321 mm/0.25 μm, N2 Mijin, D.Z.Antonovic, D.G.Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary columnJ. Serb. Chem. Soc.2004, 69, 10, 759-767.
Kovats' RI, non-polar column, isothermal Capillary DB-5 787.25 150. isothermal 60. m/0.321 mm/0.25 μm, N2 Mijin, D.Z.Antonovic, D.G.Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary columnJ. Serb. Chem. Soc.2004, 69, 10, 759-767.
Kovats' RI, non-polar column, isothermal Capillary DB-5 763.43 170. isothermal 60. m/0.321 mm/0.25 μm, N2 Mijin, D.Z.Antonovic, D.G.Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary columnJ. Serb. Chem. Soc.2004, 69, 10, 759-767.
Kovats' RI, non-polar column, isothermal Capillary DB-5 791. 190. isothermal 60. m/0.321 mm/0.25 μm, N2 Mijin, D.Z.Antonovic, D.G.Temperature dependence of the Kovats retention indices for alkyl 1,3-diketones on a DB-5 capillary columnJ. Serb. Chem. Soc.2004, 69, 10, 759-767.
Kovats' RI, non-polar column, isothermal Packed SE-30 775. 150. isothermal Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m Tiess, D.Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe1984, 33, 6-9.

Computed Properties

Molecular Weight:100.12
XLogP3:0.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:100.052429494
Monoisotopic Mass:100.052429494
Topological Polar Surface Area:34.1
Heavy Atom Count:7
Complexity:82.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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  • Data: 2025-03-27
  • Price: 16000.00Yuan/mt
  • Change: 0

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