Grundinformationen
- Standard-SMILES
CC(=O)C(C)C- InChIKey
SYBYTAAJFKOIEJ-UHFFFAOYSA-N- Summenformel
- C5H10O
- Durchschnittliche Molmasse
- 86,13 g/mol
- Monoisotopische Masse
- 86,07316494
Überblick
3-methylbutan-2-one appears as a colorless liquid with a pleasant odor. Flash point below 70 °F. Less dense than water. May be toxic by inhalation and skin absorption. Used as a solvent.
Namen und Bezeichner
- Bevorzugter Name
- 3-Methyl-2-butanone
- IUPAC
- 3-methylbutan-2-one
- Lokaler Name
- 3-Methylbutanon
- Englischer Name
- 3-Methyl-2-butanone
- Summenformel
- C5H10O
- Molmasse
- 86.13
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
563-80-4- PubChem CID
- 11251
- DTXSID
DTXSID0022062- ChEMBL
CHEMBL3183920- ChEBI
CHEBI:179699- UNII
- V8DP6THY5O
- EC Number
- 209-264-3
- Nikkaji
- J43.513I
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,8
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 6
- Formalladung
- 0
- Komplexität
- 55
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 0.84
0.84
0.84
Odor
The odor threshold lies between 1.9 and 3.1 ppm (6.8 and 11 mg/cu m). Acetone-like odor.
Acetone-like odor
Density
0.8051 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8501 g/cu cm at 20 °C
0.8 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.10
0.81
0.805 @ 16°C
Solubility
Very slight (NIOSH, 2024)
Miscible with ethanol, ethyl ether; very soluble in acetone; soluble in carbon tetrachloride
In water, 5.237X10+4 mg/L at 20 °C
Solubility in water, g/100ml at 20 °C: 0.6 (poor)
Very slight
Physikochemische Eigenschaften
- Schmelzpunkt
- -92 °C · -92 °C (lit.)
- Siedepunkt
- 94 · 94-95 °C (lit.)
- Dichte
- 0.805 g/mL · 0.805 g/mL at 25 °C (lit.)
- Dampfdruck
- 53.33 hPa · 53.33 hPa (19.9 °C)
- Brechungsindex
- 20 · n20/D 1.388(lit.)
- Flammpunkt
- 6 °C · 6 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 8.21 g/L · water: soluble8.21g/L at 20°C
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless
- Geruch (Odor)
- 0.1 %indipropylene · at 0.10%indipropylene glycol. camphor
- Odor Threshold
- 0.5 ppm · 0.5ppm
- Explosionsgrenze
- 1.5 · 1.5-9%(V)
- Wasserlöslichkeit
- 6 g/L · 6 g/L (20 ºC)
- Spezifische Wärmekapazität
- 2.09 J/ · Cp(liquid): 2.09 J/(g·K), at 25℃
- Merck
- 14 · 14,6090
- BRN
- 1071238 · 1071238
- Henry's Law Constant
- 1.1 · 1.1×10-1 mol/(m3Pa) at 25℃, Brockbank (2013)
- Dielectric constant
- 16.57 · 16.57
- Kosmetik-Inhaltsstoffe Funktionen
- PERFUMING
- InChI
- 1S/C5H10O/c1-4(2)5(3)6/h4H,1-3H3
- InChIKey
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N
- SMILES
- CC(C)C(C)=O
- LogP
- 2.29 at · 2.29 at 20℃
- CAS Datenbank
- 563 · 563-80-4(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Butanone, 3-methyl-(563-80-4)
- EPA chemische Informationen
- Methyl isopropyl ketone (563-80-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger 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)
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Chemical: 2-Butanone, 3-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
2-Butanone, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, 3-methyl- 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: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/10392
Isopropyl methyl ketone: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Acrid smoke and fumes (USCG, 1999)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Highly flammable. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive.
Health Hazards
Irritating to the eyes, nose, throat, upper respiratory tract, and skin. (USCG, 1999)
· Inhalation or contact with material may irritate or burn skin and eyes.
Hazards Summary
A skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [ICSC] An irritant; [MSDSonline] Causes narcosis in experimental animals fed high doses by oral gavage; TLV Basis is toxicity to embryo, fetus, and newborn; [ACGIH]
DOT ID and Guide
2397 127
2397 127
Reactivity Profile
Ketones, such as 3-METHYLBUTAN-2-ONE, 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.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. 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.
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from NIOSH Pocket Guide for Methyl isopropyl ketone:
General First Aid:
(General first aid procedures)
Fire Fighting Procedures
Water may be ineffective.
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Wear self contained breathing apparatus for fire fighting if necessary. Use water spray to cool unopened containers.
Cleanup Methods
Personal precautions: 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.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
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.
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.
Spillage Disposal
Consult an expert! Personal protection: self-contained breathing apparatus. Remove all ignition sources. Collect leaking liquid in covered containers. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.
Toxikologische Informationen
Body Burden
Methyl isopropyl ketone was detected in exhaled breath samples collected from a prediabetic population of 14 Chicago, Illinois residents(1). During a study of the occurrence of volatile organic compounds in human milk samples from five industrial US cities, methyl isopropyl ketone was detected in one milk sample collected in Jersey City, NJ and one milk sample collected in Pittsburgh, PA(2,3).
Ecotoxicity Values
EC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1110000 ug/L for 24 hr; Effect: behavior, equilibrium
EC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1120000 ug/L for 48 hr; Effect: behavior, equilibrium
LC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1290000 ug/L for 24 hr
LC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1200000 ug/L for 48 hr
For more Ecotoxicity Values (Complete) data for Methyl isopropyl ketone (6 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a log Kow of 0.84(2) and a regression-derived equation(3), indicates that methyl isopropyl ketone is expected to have very high mobility in soil(SRC). Volatilization of methyl isopropyl ketone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.13X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 52.2 mm Hg at 25 °C(4), and water solubility, 5.237X10+4 mg/L(5). Methyl isopropyl ketone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Methyl isopropyl ketone reached 99% of its theoretical BOD using an activated sludge inoculum in the Japanese MITI test(6) suggesting that biodegradation is an important environmental fate process for this substance in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a log Kow of 0.84(2) a regression-derived equation(3), indicates that methyl isopropyl ketone 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 1.13X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 52.2 mm Hg at 25 °C(5), and water solubility, 5.237X10+4 mg/L at 30 °C(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5.8 hours and 5.9 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 1.4(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methyl isopropyl ketone reached 99% of its theoretical BOD using an activated sludge inoculum in the Japanese MITI test(9) suggesting that biodegradation is an important environmental fate process for this substance in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl isopropyl ketone, which has a vapor pressure of 52.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl isopropyl ketone 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 5.6 days(SRC), calculated from its rate constant of 2.87X10-12 cu cm/molecule-sec at 25 °C(3). Methyl isopropyl ketone's UV absorption spectrum shows maximum absorption near 280 nm with a shoulder extending above 290 nm(4); therefore, this substance may be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
Methyl isopropyl ketone has been detected in the meat volatiles of chicken and beef(1). Reported mean concentrations of methyl isopropyl ketone measured in the headspace volatiles of wines from six regions of the Napa Valley, California ranged from 0.001 to 0.225 mg/L(2).
Exposure Routes
The substance can be absorbed into the body by inhalation of its vapour.
inhalation, ingestion, skin and/or eye contact
Milk Concentrations
ENVIRONMENTAL: During a study of the occurrence of volatile organic compounds in human milk samples from five industrial US cities, methyl isopropyl ketone was detected in one milk sample collected in Jersey City, NJ and one milk sample collected in Pittsburgh, PA(1,2).
Signs and Symptoms
Cough. Dizziness. Headache. Nausea. Drowsiness.
Redness. Dry skin.
Redness. Pain.
Vomiting. Weakness. Further see Inhalation.
irritation eyes, skin, mucous membrane, respiratory system; cough
Effluent Concentrations
Methyl isopropyl ketone was listed among approximately 200 gas-phase organic species that have been reported in the literature as emanating from either gasoline or diesel vehicles but were not identified in vehicle emissions collected from the Allegheny Mountain tunnel of the Pennsylvania Turnpike during 1979(1). Methyl isopropyl ketone was detected in headspace sampling of waste building materials consisting of mold-infested fiberboard or wall paper(2,3). It was also detected in the headspace air and liquid exudate of garden waste(2,3).
During a study of organic components in aqueous effluents from energy-related processes, methyl isopropyl ketone was detected at 55 ppb in a product water sample from an in situ coal gasification facility in Hanna, WY, at 89 ppb in process water from an in situ coal gasification facility in Gillette, WY, and at 20 ppb in retort water from an in situ oil shale processing facility in Rock Springs, WY(1). Methyl isopropyl ketone was detected in treated water samples collected following ozonation(2).
During a study exploring potential carbonyl compound by-products of ozone wastewater treatment, methyl isopropyl ketone was detected in samples of final liquor from a sludge-pressing plant following ozonization of the sample in a laboratory(1). Methyl isopropyl ketone was identified as one of the products of the reaction of hydroxyl radicals with 2,3,4-trimethylpentane in the presence of NO. The reported experimental molar yield was approximately 41%(2).
Soil Adsorption/Mobility
The Koc of methyl isopropyl ketone is estimated as 38(SRC), using a log Kow of 0.84(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methyl isopropyl ketone is expected to have very high mobility in soil.
Sicherheitsdaten
- OEB
- A
- OEL
- TWA: 200 ppm (705 mg/m3)
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 2397
- hs_code
- 29141990
- RTECS-Nr.
- EL9100000
- risk_code
- 11-67
- Toxizität
- LD50 orally in male mice: 29.86 mmol/kg (Tanii)
- hazard_code
- F
- hazard_note
- Highly Flammable
- safety_code
- 9-16-33
- hazard_class
- 3
- packing_group
- II
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 563-80-4(Hazardous Substances Data)
- Hazard Classifications
- Flam. Liq. 2
- Selbstentzündungstemperatur
- 475 °C
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Ketones are not readily metabolized in the body. With most of the lower ketones as much as 50% of the dose may be eliminated unchanged from the body, mainly in the exhaled air and to a small extent in the urine. The major metabolic pathway of ketones is reduction to the corresponding secondary alcohols, which are usually eliminated as glucuronic acids. In rats, 38-54% of a dose of 1000 mg/kg bw methyl isopropyl ketone was eliminated unchanged in about 25-35 hours, mainly in the expired air. Administration of this ketone to rabbits increased the glucuronic acid output. It has been suggested that MIPK is a normal constituent of human urine.
Verwendung und Herstellung
Uses
A pyrolysis product from hot gas welding of PVC plastic; [ACGIH]
Burning Synthetic Polymers [Category: Burn]
3-Methyl-2-butanone is employed predominantly as an intermediate for the production of pharmaceuticals, herbicides, and dye precursors. It is also used in the synthesis of rubber auxiliaries and for the selective extraction of rare earth elements.
Solvent for nitrocellulose lacquers.
Solvent
U.S. Production
2023: 1,000,000 - <5,000,000 lb
2-Butanone, 3-methyl- is listed as a High Production Volume (HPV) chemical (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).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7756]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Butanone, 3-methyl-. Aggregated National Production Volume: 1 to < 10 million lbs.
Methods of Manufacturing
Condensation of 2-butanone, formaldehyde, and hydrogen in a single step over palladium, or in two steps by condensation on a strongly acidic cation exchanger, isolation of the 2-methyl-1-buten-3-one, followed by hydrogenation.
By reaction of isobutyraldehyde with acetaldehyde in the gas phase over manganese oxide-aluminum oxide at 450 °C. Isobutyric acid and acetic acid may be used in place of isobutyraldehyde and acetaldehyde.
By addition of water to isoprene at ca. 200 °C in the presence of phosphoric acid on silica.
By oxidation of 2-methyl-2-butene with oxygen or hydroperoxides in the presence of molybdenum naphthenate at 150 °C.
Synthetic, also by fermentation.
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
2-Butanone, 3-methyl-: ACTIVE
Synthetic, also by fermentation.
Anwendungen
Verwenden3-Methyl-2-butanone is used for synthesis of heterocyclic compounds and important intermediate of medicine. It is used as an industrial solvent.
Darstellung
synthetische3-Methyl-2-butanone is produced by oxidation of Methyl-iso-propylcarbinol (2-Methyl-3-butanol).
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