Isobutyl ketone

HCID 7958CAS 108-83-8

Grundinformationen

Standard-SMILES
CC(C)CC(=O)CC(C)C
InChIKey
PTTPXKJBFFKCEK-UHFFFAOYSA-N
Summenformel
C9H18O
Durchschnittliche Molmasse
142,24 g/mol
Monoisotopische Masse
142,1357652

Überblick

Diisobutyl ketone appears as a clear colorless liquid. Flash point 140 °F. Less dense than water and insoluble in water. Vapors heavier than air.

Namen und Bezeichner

Bevorzugter Name
Isobutyl ketone
IUPAC
2,6-dimethylheptan-4-one
Lokaler Name
2,6-Dimethylheptan-4-on
Englischer Name
2,6-Dimethyl-4-heptanone
Summenformel
C9H18O
Molmasse
142.24

Namen und Synonyme

2,6-Dimethyl-4-heptanone2,6-Dimethylheptan-4-one108-83-8DIISOBUTYL KETONEIsovaleroneIsobutyl ketones-DiisopropylacetoneValeroneDIBKDiisobutilchetoneDi-isobutylcetone4-Heptanone, 2,6-dimethyl-
Weitere Namen anzeigen
FEMA 35372,6-dimethyl-4-heptanone (diisobutyl ketone)NSC 15136isovaleron
Diisobutylketonsym-Diisopropylacetonesec-Diisopropyl acetone2,6-Dimetil-eptan-4-one2,6-Dimethyl-heptan-4-on2,6-DimethylheptanoneFEMA No. 3537DTXSID4025080

Datenbank-Bezeichner

CAS
108-83-8、68514-40-9
PubChem CID
7958
DTXSID
DTXSID4025080
ChEMBL
CHEMBL3182186
ChEBI
CHEBI:89195
UNII
V52W30H1BU
EC Number
203-620-1
Nikkaji
J5.081D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,5
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
4
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Flammable agents - 2nd degree

Volatile Organic Compound (VOC)

SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesBoiling point
LogP2.560
Odor · 2 Einträge

Peppermint odor

Mild, sweet odor

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physikochemische Eigenschaften

Schmelzpunkt
-46 °C · -46 °C
Siedepunkt
165 · 165-170 °C(lit.)
Dichte
0.808 g/mL · 0.808 g/mL at 25 °C(lit.)
Dampfdichte
4.9 · 4.9 (vs air)
Dampfdruck
1.7 mm · 1.7 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.412(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1317) of reports.

Warning

H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 4-Heptanone, 2,6-dimethyl-

4-Heptanone, 2,6-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 4-Heptanone, 2,6-dimethyl- 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: 18-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/2026

4-Heptanone, 2,6-dimethyl-: HSNO Approval: HSR001130 Approved with controls

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.)

DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

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

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 49 °C explosive vapour/air mixtures may be formed.

Fire PotentialFlammable liquid when exposed to heat or flame ...
Health Hazards · 2 Einträge

Inhalation of vapor causes irritation of nose and throat. Ingestion causes irritation of mouth and stomach. Vaporirritates eyes. Contact with liquid irritates skin. (USCG, 1999)

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Hazards Summary · 2 Einträge

Humans experience offensive irritating effects below concentrations that cause CNS depression in experimental animals. [HSDB]

The major hazards encountered in the use and handling of diisobutyl ketone stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, and dermal contact), exposure to this colorless peppermint-smelling oily liquid may occur from its use as a solvent for nitrocellulose, crepe rubber, and vinylite, and as an intermediate in the synthesis of inhibitors, pharmaceuticals, dyes, and insecticides. Effects from exposure may include irritation or contact burns to the skin and eyes, shortness of breath, nausea, headache, dizziness, fainting, coma and death. Both the ACGIH and the final rule for the OSHA PEL have been set at a TWA of 25 ppm. Even though the odor of diisobutyl ketone may provide sufficient warning of its presence, in activities or situations where over-exposure may occur, wear a self-contained breathing apparatus and appropriate chemical protective clothing, including gloves and boots. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. Diisobutyl ketone may be ignited by heat, sparks, or flames. Its heavier than air vapor may travel to a source of ignition and flash back, or result in a build-up of explosive concentrations in enclosed spaces such as sewers. Also, containers may explode in the heat of a fire. Fires involving diisobutyl ketone may be extinguished with dry chemical, CO2, Halon, alcohol foam, and water spray, mist, or fog (solid streams of water may be ineffective). Since diisobutyl ketone fires may produce irritating or poisonous gases, when tank cars or trucks are involved, isolate the area for one half mile in all directions. Fight the fire from as far a distance as possible, and dike runoff from fire control water. Diisobutyl ketone should be stored in cool, well-ventilated place, away from direct sunlight, sources of ignition, and oxidizing materials. Diisobutyl ketone may be shipped via air, rail, road, and water. Small spills of diisobutyl ketone may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Large spills should be diked far ahead of the spill for later disposal. Before implementing land disposal of waste diisobutyl ketone, consult with environmental regulatory agencies for guidance.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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

Use AFFF, alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

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.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· 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 · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Target OrgansEyes, skin, respiratory system, central nervous system, liver, kidneys
Ecotoxicity Values · 4 Einträge

EC50 Selenastrum capricornutum (Algae) 100 mg/L/96 hr; biomass.

LC50 Oncorhynchus mykiss (/Rainbow trout/) 140 mg/L/96 hr; semistatic, freshwater.

LC50; Species: Artemia salina (Brine shrimp, nauplii); Conditions: saltwater, static, 24 °C; Concentration: 65 mg/L for 24 hr

EC50 Daphnia magna (Water flea) 250 mg/L/48 hr; static; Effect: immobilization

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a water solubility of 2,640 mg/L(2) and a regression-derived equation(3), indicates that diisobutyl ketone is expected to have high mobility in soil(SRC). Volatilization of diisobutyl ketone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.65 mm Hg(3), and water solubility(2). Diisobutyl ketone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Diisobutyl ketone was shown to rapidly biodegrade under aerobic conditions(4-6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a water solubility of 2,640 mg/L(2) and a regression-derived equation(3), indicates that diisobutyl ketone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.65 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 12 hours and 7.5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation in oxygenated waters is expected to be an important environmental fate process for this compound(6-8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diisobutyl ketone, which has a vapor pressure of 1.65 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diisobutyl 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 15 hours(SRC), calculated from its rate constant of 2.6X10-11 cu cm/molecule-sec at 25 °C(3). The photochemical degradation products of diisobutyl ketone with hydroxyl radicals are acetone and 2-methylpropanal(4). Diisobutyl ketone contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(5).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 Einträge

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

inhalation, ingestion, skin and/or eye contact

Toxicity Summary · 1 Eintrag

The consumer exposure is considered to be low as only very few of the DIBK-containing products are accessible to the consumer. Mean occupational exposure during formulation and use of DIBK-containing products is estimated to be about 16-39 mg/cu m DIBK is not corrosive or sensitizing. Respiratory irritation was observed in humans at concentrations above 50 ppm. The NOAEL for repeated dose following inhalation exposure is in the region of 534 ppm. For reproductive toxicity, no increased risks to offspring were observed in the absence of parental effects. The NOAEL for parental toxicity was determined as 300 mg/kg bw/d and for reproductive effects 1000 mg/kg bw/d. Bacterial mutagenicity tests are negative, as well as a Saccharomyces cerevisiae mitotic gene conversion assay. DIBK does not induce chromosome aberrations in rat liver cells in vitro. ...

Regulatorische Informationen

FDA RequirementsDiisobutyl ketone is an indirect food additive for use only as a component of adhesives.

Sicherheitsdaten

OEB
A
OEL
TWA: 25 ppm (150 mg/m3)
wgk
1
IDLA
500 ppm
tsca
TSCA listed
ridadr
UN 1157

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

There appears to be no specific information on the details of metabolism of diisobutyl ketone, but it probably undergoes the major metabolic change common to that of most ketones except acetone. That is reduction to the corresponding secondary alcohol which is usually eliminated combined with glucuronic acid.

Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 6 Einträge

Mainly used as coating solvent; [HSDB]

Painting (Solvents) [Category: Paint]

SOLVENT FOR NITROCELLULOSE, FOR MILLED CREPE RUBBER, VINYLITE, SYNTHETIC COATINGS AND AS A DISPERSANT FOR ORGANOSOL TYPE RESINS; INTERMEDIATE IN SYNTHESIS OF INHIBITORS, PHARMACEUTICALS, DYES, & INSECTICIDES

Solvent for nitrocellulose, rubber, synthetic resins; lacquers; coating compositions; organic synthesis, roll-coating inks; stains.

Mainly used as coating solvent. Catalytic oxidation produces 2,6-dimethyl-4-heptanol (108-82-7).

... Solvent for paints, dyes and adhesives, and as an extraction agent for the recrystallization of organic compounds.

U.S. Production · 4 Einträge

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

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1510]

4-Heptanone, 2,6-dimethyl- 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).

There are only 2 major producers/importers within the EU. The production/import volume in the EU is 5500 to 6500 t/a. In Canada, 2 companies manufactured DIBK between 1984 and 1986 (personal communication, no recent data available). The total production for 1986 was between 1000 and 10,000 tons. The total import quantites for 1986 was between 23 and 230 tons.

Consumption Patterns/DIBK/ use in the solvents for paints is relatively small at approximately 3500 t/a out of a total solvents use by the European paints sector of approximately 2x10+6 t/a.
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesSolvent
Methods of Manufacturing · 2 Einträge

Diisobutyl ketone can be produced by the hydrogenation of phorone which, in turn, is produced by the acid-catalyzed aldol condensation of acetone. It is also a coproduct in the manufacture of methyl isobutyl ketone.

... Prepared by the dehydrogenative condensation of isopropyl alcohol with 4-methyl-2-pentanone as byproduct. A mixture of acetone and isopropyl alcohol may be used instead of the latter alone. 2,6-Dimethyl-4-heptanone can also be produced by the reductive condensation of acetone with 4-methyl-2-pentanone.

Anwendungen · 3 Einträge

Beschreibung2, 6-Dimethyl-4-heptanone, also known as diisobutyl ketone, belongs to the family of ketones, being a flavoring ingredient. It can also be used as the extraction solvent for the determination of ten trace metals (V, Cr, Fe, Co, Ni, Cu, Zn, Mo, Cd, Pb) in aqueous samples with plasma atomic emission spectrometry. Similar logic can also be applied to the measurement of phosphorus using 2, 6-dimethyl-4-heptanone as the extraction agent. It is also an important organic solvent widely used as industrial intermediates.

OccurrenceReported found in baked potato and wheaten bread.

Verwenden2,6-Dimethyl-4-heptanone is used as a coating solvent. It is an active component of mint oil. It acts as a dispersant for organosol type resins. It is involved in the antigerminative treatment of bulbs and tubers. Further, it is used as a solvent for nitrocellulose. In addition to this, it acts as an intermediate in the preparation of inhibitors, active pharmaceutical ingredients and dyes.

Anbieter50 Anbieter

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