HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Octan-2-on
METHYL HEXYL KETONE · Octan-2-one · 2-Octanon · FEMA 2802 · HEXYL METHYL KETONE · METHYL N-HEXYL KETONE · MHK · Methvlhexanone
Identifikatoren & physikalische Daten
| CAS No. | 111-13-7 |
|---|---|
| Summenformel | C8H16O |
| Durchschnittliche Molmasse | 128,21 g/mol |
| Monoisotopische Masse | 128,12011513 g/mol |
| SMILES | CCCCCCC(C)=O |
| InChIKey | ZPVFWPFBNIEHGJ-UHFFFAOYSA-N |
| PubChem CID | 8093 |
| ChEMBL | CHEMBL18549 |
| ChEBI | CHEBI:87434 |
| EC No. | 203-837-1 |
| DTXSID | DTXSID4021927 |
| Lokaler Name | Octan-2-on |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 76 |
| LogP (Verteilungskoeffizient) | log Kow = 2.37 |
| Geruch | FATTY, GREEN CHEESE AROMAFLORAL, BITTER, FRUITY (UNRIPE APPLE)Pleasant |
| Geschmack | Camphor tasteCHEESEBITTER |
| Dichte | 0.820 at 20 °C/4 °C0.813-0.8190.820 @ 20°C0.819 g/mL at 25 °C(lit.) |
| Color/Form | Colorless liquid |
| Löslichkeit | Miscible with alcohol, ether1:9-12 IN 50% ALCOHOL, 1:1-1.7 IN 70% ALCOHOLSoluble in alcohol, hydrocarbons, ether, esters, etc.In water, 899 mg/L at 20 °C0.899 mg/mL at 20 °C1 ml in 1 ml 95% alcohol (in ethanol)0.9g/l0.9 g/L |
| Flammpunkt | 125 °F (52 °C) (Closed cup)133 °F |
| Siedepunkt | 173.5173.00 to 175.00 °C. @ 760.00 mm Hg174-175 °C172.5 °C @760 [mm Hg]173 °C(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -16 °CLiquid Molar Volume = 0.157391 cu m/kmolIG Heat of Formation = -3.2160X10+8 J/kmolHeat of Fusion at melting point = 2.4419X10+7 J/kmol |
| Dampfdichte | 4.4 (Air = 1) |
| Geruchsschwelle | Odor Threshold Low: 248.0 [ppm]Odor threshold from HSDB1,304 mg/cu m = 248 ppm |
| Dampfdruck | 1.8-2.614hPa at 20-25℃ |
| FEMA | 2802 | 2-OCTANONE |
| Brechungsindex | n20/D 1.416(lit.) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to very slightly yellow |
| Geruch | at 10.00 % in dipropylene glycol. earthy weedy natural woody herbal |
| Geruchsart | earthy |
| Biologische Quelle | synthetic |
| Spezifische Wärmekapazität | Cp(liquid): 2.13 J/(g·K), at 25℃ |
| JECFA Number | 288 |
| Merck | 14,4711 |
| BRN | 635843 |
| Henry-Konstante | 5.0×10-2 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 7.4(100℃) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. Flammable. |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C8H16O/c1-3-4-5-6-7-8(2)9/h3-7H2,1-2H3 |
| InChIKey | ZPVFWPFBNIEHGJ-UHFFFAOYSA-N |
| SMILES | CCCCCCC(C)=O |
| LogP (Verteilungskoeffizient) | 1.95-2.37 at 25℃ |
| CAS Datenbank | 111-13-7(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Octanone(111-13-7) |
| EPA chemische Informationen | 2-Octanone (111-13-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.8% (15 of 1970) of reports.WarningH226 (99%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1970 reports by companies from 15 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 15 of 1970 reports by companies.There are 14 notifications provided by 1955 of 1970 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 2-OctanoneRegulation (EC) No 1831/2003 (amended)2-Octanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Octanone 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)Status: Active Update: 08-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/174242-Octanone: Does not have an individual approval but may be used under an appropriate group standard |
| Brandpotenzial | Flammable liquid when exposed to heat, flame, or oxidizers. |
| Gefahrenübersicht | May cause mild irritationInhalation of high concentrations can cause CNS depression[HSDB] Safe when used as a flavoring agent in food[JECFA] An irritantHarmful by skin absorption[Alfa Aesar MSDS] |
| FDA-Anforderungen | 2-Octanone 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: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient. |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Flam. Liq. 3 (99%)Flammable liquids - Category 3Serious eye damage/eye irritation - Category 2Specific target organ toxicity - Single exposure - Category 3 (Narcotic effects, Respiratory tract irritation)Hazardous to the aquatic environment (Acute) - Category 3Hazardous to the aquatic environment (Long-term) - Category 3 |
| Skin, Eye, and Respiratory Irritations | 2-Octanone has a relatively low toxicity. Direct skin contact may cause defatting and irritation of the skin. Inhalation may produce mild symptoms of eye, nose, and throat irritation at low concentrations, and may cause /CNS depression/ at high concentrations. |
| Brandbekämpfungsverfahren | To fight fire, use foam, alcohol foam. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Protective Action Criteria (PAC) | 9.3 [mg/m3]100 [mg/m3]610 [mg/m3] |
| Wechselwirkungen | The conduction velocity of motor and sensory fibers of the tail in rats were not affected following repeated subcutaneous injections of 2-octanone alone, but injections of 2-octanone together with MnBK (methyl n-butyl ketone) significantly enhanced the neurotoxic effect seen with MnBK alone.The effect of aliphatic nontoxic ketones on the neurotoxicity of methyl-n-butyl-ketone was studied in rats. Male Donryu-rats were exposed to methyl-n-butyl-ketone alone or in combination with methylethyl-ketone, methyl-n-propyl-ketone, methyl-n-amyl-ketone, or methyl-n-hexyl-ketone. Each ketone was injected subcutaneously in equimolar doses of 4 millimoles per kilogram, once daily, five days a week for 20 weeks. The animals were weighed biweekly and observed for signs of neurotoxicity. Maximum motor fiber conduction velocity and distal latency were measured every two weeks in the tail nerves. All treated animals showed significant decreases in body weights, relative to controls. Animals treated with methyl-n-butyl-ketone plus methyl-n-propyl-ketone, methyl-n-amyl-ketone, and methyl-n-hexyl-ketone showed greater weight decreases than those treated with methyl-n-butyl-ketone alone. Treated animals showed weakness in the hind legs. Hind leg weakness was more severe in rats treated with the combined ketone doses than with methyl-n-butyl-ketone alone. All the ketones enhanced the neurotoxicity of methyl-n-butyl-ketone as measured by decreased motor conduction velocities and prolonged distal latencies of the tail nerve. Methyl-n-hexyl-ketone had the greatest potentiating effect on methyl-n-butyl-ketone. The authors note that methyl-n-hexyl-ketone had the longest carbon chain. They suggest that the lengths of the carbon chain of the aliphatic ketones is directly related to their abilities to potentiate methyl-n-butyl-ketone neurotoxicity. |
| Ökotoxizitätswerte | LC50 Pimephales promelas (Fathead minnow) 36 mg/L 96 hr flow-through bioassay, weight 0.12 g, water hardness 45.5 mg/L CaCO3, temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen >60% of saturation |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a log Kow value of 2.37(2) and a regression-derived equation(3), indicates that 2-octanone is expected to have moderate mobility in soil(SRC). Aerobic biodegradation of this compound is expected. 2-Octanone, inoculated with acclimated sludge, had BOD values from 33%(4) to 48%(5,6) of the theoretical oxygen demand after 5 days incubation. Volatilization of 2-octanone from moist soil surfaces in expected to be an important fate process(SRC) given a Henry's Law constant of 1.88X10-4 atm-cu m/mole(7). 2-Octanone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.35 mm Hg(8). Theoretical BOD values of 33%(8) and 48%(9) suggest that biodegradation may occur in soil(SRC).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 460(SRC), determined from a log Kow value of 2.37(2) and a regression-derived equation(3), indicates that 2-octanone is expected to adsorb to suspended solids and sediment(SRC). In water, 2-octanone has a measured volatilization flux of 40 g/min/sq msome attenuation of this process is expected due to the gas-film interface(4). A measured Henry's Law constant of 1.88X10-4 atm-cu m/mole(5) also indicates that this compound will volatilize from water surfaces. Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 6 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 13(SRC), from its log Kow(2), and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. 2-Octanone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Theoretical BOD values of 33%(8) and 48%(9,10) suggest that biodegradation may occur in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-octanone, which has a vapor pressure of 1.35 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-octanone 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 1.6 days(3). 2-Octanone does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4). |
| Lebensmitteluntersuchungswerte | 2-Octanone is present, at unreported concentrations, as a volatile component of aroma of cooked beef, mutton, chicken, and pork(1). 2-Octanone was identified in the volatile components of clam and corbicula(2), and raw beef(3). 2-Octanone was identified in Beaufort cheese(4), blue cheese(5), roasted filberts(6), and in peanut oil, heated to 200 °C, at unreported concentrations(7). 2-Octanone was isolated as a volatile component of duck meat (0.08 ppb), duck fat (0.91 ppb), Cantonese style roasted duck (trace) and Cantonese style roasted duck gravy (trace)(8). 2-Octanone was detected in whole and ground musty sorghum with direct helium-purge method, and detected in ground musty sorghum with supercritical fluid extraction(9).2-Octanone was reported in concentrations of 73.9 ug/kg to 86.7 ug/kg in fermented soybean (Glycine max) curd(10). The lipid fraction of raw beef contained unreported concentrations of 2-octanone(11). 2-Octanone was measured at 25.7 ng/g in hair tail viscera fish paste(12). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Effluent Concentrations | 2-Octanone was detected in the volatile emissions of a liquid floor wax and a liquid wax for marble, ceramic, and linoleum at unreported concentrations(1). Volatile fractions from fresh and used machine cutting-fluid emulsion contained 2-octanone at 0.114 and 0.540 ug/g, respectively(2). Process water from in situ coal gasification (at 29 ppb), aqueous condensate from low-Btu gasification of coal (at 188 ppb), and Omega-9 retort water from in situ oil shale processing (at 126 ppb) contained 2-octanone(3). 2-Octanone was detected but not quantified in the emissions of building materials with microbial growth(4). |
| Soil Adsorption/Mobility | The Koc of 2-octanone is estimated as 460(SRC), using a measured log Kow of 2.37(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-octanone is expected to have moderate mobility in soil(SRC). |
| TSCA Test Submissions | 2-Octanol (CAS # 111-13-7) was evaluated for acute inhalation toxicity. An acute toxicity study was conducted with 5 male albino rats (strain not reported) receiving 2-octanol by aspiration. Animals were anesthetized and 0.2ml of the test substance was placed in the mouth. Animals were then placed in a vertical position with mouth open and nostrils closed at expiration to promote entry of the liquid into the trachea. Four of the five animals died instantly or within minutes after dosing. The remaining animal was sacrificed, 24 hours after dosing. Lungs were removed from all animals for examination. Animals dying within minutes of dosing were observed with bloody exudate from nostrils (2 animals) and macroscopic examination of the lung revealed petechial pulmonary hemorrhages (1 animal) and pin point pulmonary hemorrhages (1 animal). Lungs of the animal sacrificed 24 hours after dosing were normal by macroscopic examination. The average weight of lungs from the treated animals was 2.81g, and the average weight of the negative (water) controls was 1.38g. It was concluded by the authors that the death occurred due to respiratory paralysis or cardiac arrest or both, based upon the rapid cessation of respiratory or cardiac action, and lung weights and macroscopic appearance of the lungs. |
| Natural Pollution Sources | REPORTED FOUND IN SMALL QUANTITIES IN THE ESSENTIAL OIL OF RUTA MONTANA L AND IN A FEW VARIETIES OF BANANA AND CITRUS FRUITS. |
| Atmospheric Concentrations | INDOOR: 2-Octanone was detected but not quantified in 5 of 44 emission samples from furniture(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Tested at 4% in petrolatum, it produced no irritation after a 48 hour closed-patch test on human subjects ... and no sensitization reactions .../SIGNS AND SYMPTOMS/ 2-Octanone has a relatively low toxicity. Direct skin contact may cause defatting and irritation of the skin. Inhalation may produce mild symptoms of eye, nose, and throat irritation at low concentrations, and may cause /CNS depression/ at high concentrations. |
| Artificial Pollution Sources | 2-Octanone's production and use as a fragrance and flavoring ingredient, as a high-boiling solvent, in leather finishes, as an odorant, and as an anti-blushing agent for nitrocellulose lacquers(1) may result in its release to the environment through various waste streams(SRC). |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1224 3/PG 3 |
| Zollcode | 29141990 |
| RTECS-Nr. | RH1484000 |
| R-Sätze (R) | 21-10 |
| Toxizität | Both the acute oral LD50 in rats and the acute dermal LD50 in rabbits exceeded 5 g/kg (Moreno, 1973). |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37-16 |
| Gefahrenklasse | 3Acute Tox. 4 DermalFlam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 111-13-7(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
2-Octanone has a floral and bitter, green, fruity (unripe apple) odor with a bitter camphoraceous taste. May be synthesized by the oxidation of methyl hexyl carbinol with K2Cr2O7 and sulfuric acid; also by oxidation of 2-octanol over zinc oxide at 330 - 340°C.
Occurrence
Reported found in apple, apricot, banana, cranberry, grape, raisin, papaya, peach, raspberry, strawberry, leek, peas, clove, wheat bread, many cheeses, butter, milk, cooked egg, yogurt, caviar, fatty fish, meats, beer, hop oil beer, cognac, rum, grape wines, cocoa, coffee, tea, roasted filberts and peanuts, pecans, potato chips, oats, soybean, olive, beans, walnut, trassi, mushroom, fig, rice, buckwheat, quince, sweet corn, corn oil, malt, wort, krill, Bourbon vanilla, mountain papaya, shrimp, crab, crayfish, clam, truffle, maté and mastic gum oil.
Verwenden
2-Octanone is used in perfumes, high-boiling solvent, especially for epoxy resin coatings and in leather finishes. It is used in flavoring, odorant. It can act as antiblushing agent for nitrocellulose lacquers.
Herstellung & Synthese
synthetische
By oxidation of methyl hexyl carbinol with K2Cr2O7 and sulfuric acid; also by oxidation of 2-octanol over zinc oxide at 330 to 340°C.