Acetophenone

Hazardous Air Pollutants (HAPs)

Other Classes -> Aromatic Ketones

Flammable agents - 2nd degree

Semi-Volatile Organic Compound (SVOC) and(or) Waste-water effluent contaminant

Fragrance Ingredient (Acetophenone) -> IFRA transparency List

Fragrance

log Kow = 1.58

1.58

1.58

1.71

Sweet pungent odor

Sweet, pungent and strong medicinal odor

Sweet almond-like smell

Sweet, pungent taste

Bitter, aromatic cherry branch taste

1.028 at 68 °F (USCG, 1999) - Denser than water; will sink

1.0281 g/cu cm at 20 °C

Density: 1.033 at 15 °C/15 °C

1.03 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1

1.022-1.028

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 2981) of reports.

Warning

H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Ethanone, 1-phenyl-

Hazard Traits - Dermatotoxicity; Hematotoxicity; Ocular Toxicity; Respiratory Toxicity

Regulation (EC) No 1831/2003 (amended)

Ethanone, 1-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanone, 1-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 08-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/14683

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Combustible. Above 77 °C explosive vapour/air mixtures may be formed.

Combustible.

Flammable liquid.

Acetophenone is used for fragrance in soaps and perfumes, as a flavoring agent in foods, and as a solvent for plastics and resins. Acute (short-term) exposure to acetophenone vapor may produce skin irritation and transient corneal injury in humans. No information is available on the chronic (long-term), reproductive, developmental, or carcinogenic effects of acetophenone in humans. EPA has classified acetophenone as a Group D, not classifiable as to human carcinogenicity.

A skin and eye irritant; Can cause CNS depression at high concentrations; [Olson, p. 661] Inhalation of high concentration can cause unconsciousness; [ICSC] In rats, the lethal concentration is >210 ppm for 8 hours; In mice, the lethal concentration (LC50) is 1200 mg/m3/4H (244 ppm/4H); [RTECS] TLV Basis: Irritation, CNS impairment; Pregnancy loss; [ACGIH]

Acetophenone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

BIBRA working group; TA:Toxicity profile. BIBRA Toxicology International: 4 (1991)

USEPA; Health and Environmental Effects Document for Acetophenone: ECAO-CIN-G001 (1987)

U004; As stipulated in 40 CFR 261.33, when acetophenone, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Residues of acetophenone are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: attractant. Limit: none.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use alcohol-resistant foam, powder, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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

Rinse mouth. Refer for medical attention .

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

To fight fire, use foam, /carbon dioxide/, dry chemical.

Use dry chemical, carbon dioxide, water spray, 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.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Light sensitive. Store under inert gas.

Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials. ... Before entering confined space where acetophenone may be present, check to make sure than an explosive concentration does not exist. Store in tightly closed containers in a cool, well-ventilated area. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard.

Separated from strong oxidants. Ventilation along the floor.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours 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 an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

Restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Use foam spray to reduce vapors. Absorb liquids in vermiculite, dry sand, earth, or similar material and deposit in sealed containers. Ventilate area of spill or leak after cleanup is complete. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Keep acetophenone out of a confined space, such as a sewer, because of the potential for 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.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U004, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

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: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material; Contaminated packaging: Dispose of as unused product.

A good candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds. A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

For more Disposal Methods (Complete) data for Acetophenone (6 total), please visit the HSDB record page.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

LC50; Species: /Pimephales promelas/ (fathead minnow); Conditions: freshwater, static bioassay in Lake Superior water, 18-22 °C; Concentration: >200 mg/L for 1 hr; >200 mg/L for 24 hr; 103 mg/L for 48 hr; 158 mg/L for 72 hr; 155 mg/L for 96 hr

LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 24.6 °C, dissolved oxygen 7.1 mg/L, hardness 40.7 mg/L calcium carbonate, alkalinity 35.0 mg/L calcium carbonate, pH 7.83; Concentration: 162 mg/L for 96 hr

EC50; Species: Pimephales promelas (fathead minnow); Conditions: flow-through bioassay with measured concentrations, 24.6 °C, dissolved oxygen 7.1 mg/L, hardness 40.7 mg/L calcium carbonate, alkalinity 35.0 mg/L calcium carbonate, pH 7.83; Concentration: 162 mg/L for 96 hr; Effect: loss of equilibrium

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 10-270(2-3) indicate that acetophenone is expected to have very high to moderate mobility in soil(SRC). Volatilization of acetophenone from moist soil surfaces is expected(SRC) given a Henry's Law constant of 1.04X10-5 atm-cu m/mole(4). Acetophenone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.397 mm Hg at 25 °C(5). Screening studies have indicated that acetophenone is readily biodegradable(6-8).

AQUATIC FATE: Based on a classification scheme(1), log Koc values in sediment of 1.23-1.98(2-3) indicate that acetophenone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.04X10-5 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 4 and 32 days, respectively(SRC). Acetophenone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). According to a classification scheme(6), an estimated BCF of 1(SRC), from its log Kow of 1.58(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation in water surfaces is expected based on half-lives of 32, 8, and 4.5 days in groundwater, river water and lake water, respectively(9-10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetophenone, which has a vapor pressure of 0.397 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acetophenone 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 6 days(SRC), calculated from its rate constant of 2.74X10-12 cu cm/molecule-sec at 25 °C(3). While acetophenone absorbs light at >290 nm(4), it is not expected to undergo direct photolysis in the environment because it donates its energy to other molecules instead of photodegrading(5).

Acetophenone was identified, not quantified, in the volatile components of filbert nut(1), clove essential oil(2), nectarines(3) and fish sauce(4). Acetophenone was detected in honey derived from yellow box (Eucalyptus melliodora) in the 1994-1995 season in Australia at 0.1-0.2 mg/kg(5). Acetophenone was detected at 110.5-188.5 ug/kg in nine honey samples derived from the honeydew of holm-oak, oak and forests of Spain(6). Acetophenone was not detected (detection limit 1 ppb) in fresh or frozen corn kernel, but was detected in canned kernel and canned cream corn at 5 and 10 ppb, respectively(7).

IDENTIFICATION AND USE: Acetophenone is a liquid, forming crystals at low temperature. It is used in perfumery to impart an orange blossom-like odor, as a catalyst for the polymerization of olefins, and in organic syntheses, especially as photosensitizer. HUMAN STUDIES: No skin sensitization was noted when 2% acetophenone in petrolatum was tested on humans. The substance is irritating to the eyes, and may cause effects on the central nervous system. Exposure at high levels could cause unconsciousness. After long-term or repeated exposure the liquid defats the skin. ANIMAL STUDIES: Application of acetophenone to the eyes of rabbits as two drops of saturated aqueous solution caused discomfort. In another study, 0.005 mL of a 15% solution (750 ug) produced severe corneal necrosis in the rabbit eye. Mice survived 0.7 g/kg of acetophenone injected intraperitoneally, but clear-cut hypnotic effects occurred rapidly at dosage levels of 0.4 to 0.5 g/kg. In a combined subchronic and reproduction/developmental screening study, groups of 10 male and 10 female rats received oral gavage administrations of 0, 75, 225 or 750 mg/kg/day acetophenone for 28 days in the toxicity phase of testing. No deaths were seen; signs of overt toxicity included increased salivation at 225 and 750 mg/kg/day. The neurological examination further indicated decreased motor activity and decreased forelimb grip at 750 mg/kg/day in males only. Other signs of overt toxicity included decreased body weight and food consumption with increased cholesterol levels for the high-dose group. In the developmental portion of the study there were no adverse effects on the mating or fertility indices or on gestation lengths. The live birth index was decreased at 750 mg/kg/day. Similarly, pup survival was decreased during lactation and mean pup weights were decreased at 750 mg/kg. There was no indication of a mutagenic activity with and without metabolic activation with the Salmonella typhimurium strains TA98, TA100 and TA1537.

Acetophenone comprised 9.6% of the ambient air around Pinus halepensis, measured June 1997 in El-Hamma Botanical Garden, Algiers, Algeria. It was not reported in air around Eucalyptus globulus or Cedrus atlantica(1).

Acetophenone occurrence in plants(1).[Table#2592]

Headache. Dizziness. Drowsiness.

Dry skin.

Redness. Pain.

Nausea. Further see Inhalation.

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of July 27, 2017: http://actor.epa.gov/dashboard/]

Acetophenone is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

U004; As stipulated in 40 CFR 261.33, when acetophenone, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Residues of acetophenone are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: attractant. Limit: none.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Acetophenone is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Acetophenone is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

... In rats acetophenone appears to be precursor of not only mandelic acid and benzoylformic acid but benzoic acid as well. ...

The reductive cleavage of hydroperoxides by purified p450 in a reconstituted system containing reduced nicotinamide adenine dinucleotide phosphate was studied. ... With cumyl hydroperoxide, acetophenone was produced, but not cumyl alcohol, indicating that a rearrangement had taken place, probably involving radical intermediates, with the formation of an additional 1-carbon product.

Early studies identified 1-phenylethanol, benzoic acid, and mandelic acid as urinary metabolites of acetophenone in rabbits and dogs. /It was/ found that rabbits administered acetophenone by gavage excreted 47% of the dose as glucuronide conjugates of 1-phenylethanol and about 20% as hippuric acid. /Another study/... reported that 1-phenylethanol and its glucuronide conjugate constituted only about 4% of the dose for rabbits treated by the ip route. ... m-Hydroxyacetophenone, p-hydroxyacetophenone, and w-hydroxyacetophenone as minor urinary metabolites of acetophenone (<1% of the dose) in rabbits.

...10% of a 100 mg/kg ip dose of radiolabeled acetophenone was excreted as /carbon dioxide/ after 4 hr and that the amount increased to 30% after 13 hr. ... Mendelic acid was present in the urine of rats treated ip with acetophenone and ... this metabolite most likely arose from w-hydroxyacetophenone.

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.

Acetophenone is used in perfumery as a fragrance ingredient in soaps, detergents, creams, lotions, and perfumes; as a flavoring agent in foods, nonalcoholic beverages, and tobacco; as a specialty solvent for plastics and resins; as a catalyst for the polymerization of olefins; and in organic syntheses as a photosensitizer.

Used in textile coatings; [Olson, p. 661] Used in perfumes for orange blossom odor; Also used in organic synthesis and as a polymerization catalyst for olefins; [Merck Index] Used in the past as an analgesic and anesthetic; [ACGIH] Used as a solvent in plastics and resins and a flavoring agent in foods; [HSDB]

Plastic Composites Manufacturing [Category: Industry]

For acetophenone (USEPA/OPP Pesticide Code: 129033) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Photosensitizing Agents

In perfumery to impart an orange-blossom-like odor; catalyst for the polymerization of olefins; in organic syntheses, esp. as photosensitizer.

(1983) 3.33X10+8 g /Tech grade/

(1983) 8.87X10+7 g /Fragrance grade/

2023: 10,000,000 - <25,000,000 lb

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethanone, 1-phenyl-. National Production Volume: 10,000,000 - 50,000,000 lb/yr.

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethanone, 1-phenyl-:

By-product from the oxidation of cumene.

Made from benzene and acetylchloride in presence of aluminum chloride; catalytically from acetic and benzoic acids. Preparation from benzene and acetic anhydride ... .

... By catalytic oxidation of ethyl benzene; also prepared by fractional distillation and crystallization from the essential oil of Stirlingia latifolia.

... oxidation of ethylbenzene with air or oxygen at 130 °C and 0.5 MPa. Catalysts used include cobalt salts or manganese salts of naphthenic or fatty acids. Conversion of ethylbenzene is limited to ca. 25% to minimize the byproducts 1-phenylethanol and benzoic acid.

Most methyl phenyl ketone originates from the Hock process for the production of phenol from isopropylbenzene; it is isolated from the residue of this process. In addition, acetophenone can be obtained as a main product by selective decomposition of cumene hydroperoxide in the presence of copper catalysts at 100 °C.

Trade Name: Hypnone

Grades: technical, refined, perfumery.

99.0% minimum purity liquid grade. /Commercially available from ARCO/

Cosmetics product ingredient: Acetophenone

Information on 52 consumer products that contain Acetophenone in the following categories is provided:

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Plastics Material and Resin Manufacturing

Ethanone, 1-phenyl-: ACTIVE