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Isobutyl ketone

HCID 178801965
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Grundinformationen

CAS
108-93-8
Standard-SMILES
CC(C)CC(=O)CC(C)C
InChIKey
PTTPXKJBFFKCEK-UHFFFAOYSA-N
Summenformel
C9H18O
Durchschnittliche Molmasse
142,24 g/mol

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

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
Diisobutylketonsym-Diisopropylacetonesec-Diisopropyl acetone2,6-Dimetil-eptan-4-one2,6-Dimethyl-heptan-4-on2,6-DimethylheptanoneFEMA No. 3537DTXSID4025080

Datenbank-Bezeichner

CAS
108-93-8
ChEMBL
CHEMBL3182186
ChEBI
CHEBI:89195
UNII
V52W30H1BU
EC Number
203-620-1
Nikkaji
J5.081D

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
2,5
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
4
Schwere Atome
10
Formalladung
0
Komplexität
91,3

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
Density · 6 Einträge

0.806 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8062 at 20 °C/4 °C

Bulk density: 6.7 lb/gal at 20 °C; coefficient of expansion: 0.00101 at 20 °C

Saturated vapor density= 0.00088 lb/cu ft @ 70 °F

Relative density (water = 1): 0.805

0.808

Flavoring AgentsEU Flavoring substances

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

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

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.

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Viscosity
0.896 Cp at 70 °F
Color/Form · 3 Einträge

WATER CLEAR LIQUID

Colorless oil

Colorless liquid

Solubility · 6 Einträge

Slightly soluble (NTP, 1992)

Miscible with ethanol, ether; soluble in carbon tetrachloride

SOL IN CHLOROFORM

Miscible with benzene

Miscibile with most organic liquids

For more Solubility (Complete) data for DIISOBUTYL KETONE (6 total), please visit the HSDB record page.

Flash Point · 6 Einträge

140 °F (NTP, 1992)

49 °C

120 °F (49 °C) (Closed cup)

49 °C c.c.

140 °F

120 °F

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.

DOT ID and Guide · 2 Einträge

1157 128

1157 128

FDA RequirementsDiisobutyl ketone is an indirect food additive for use only as a component of adhesives.
Reactive GroupKetones
EC ClassificationSymbol: Xi; R: 10-37; S: (2)-24
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
Special Reports · 2 Einträge

European Chemicals Bureau; IUCLID Dataset, 2,6-Dimethylheptan-4-one (CAS # 108-83-8) 25 p. Provides a compilation of information submitted to the EU by the European industry as of 2000. Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of September 24, 2007.

Organisation for Economic Cooperation and Development; Screening Information Data Set for Diisobutyl ketone, CAS #108-83-8, 75 p. (June 1988). Available from the Database Query page at http://www.inchem.org/pages/sids.html as of October 2, 2007

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).
Fire Fighting Procedures · 4 Einträge

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

FOAM ... WATER MAY BE INEFFECTIVE

If material on fire or involved in fire: Do not extinquish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Combustible. Extinguish with dry chemicals, foam, or carbon dioxide. Water may be ineffective on fire.

Storage Conditions · 2 Einträge

MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. IMCOMPATIBLE MATERIALS SHOULD BE ISOLATED.

Protect storage in direct sunlight. Separate from sources of ignition and oxidizing materials.

Cleanup Methods · 1 Eintrag

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. 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. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 5 Einträge

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

The EPA recommends packaging of product residues and sorbent media in epoxy-lined drums and disposal at an EPA-approved site. The compounds may be destroyed by permanganate oxidation, high temperature incineration with scrubbing equipment, or microwave plasma treatment. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (> or = to 100 kg/mo) must conform with EPA regulations governing storage, transpiration, treatment, and waste disposal.

Diisobutyl ketone is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.

The following wastewater treatment technologies have been investigated for Diisobutyl Ketone: Concentration process - active carbon.

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

Spillage Disposal · 1 Eintrag

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Ventilation. 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.

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. ...

Ecotoxicity Excerpts/OTHER TERRESTRIAL SPECIES/ Ketones, incl diisobutyl ketone, were tested for their ability to release alarm pheromones in ants. The most active cmpd were of a size & geometry similar to 4-methyl-3-heptanone.
Signs and Symptoms · 5 Einträge

Cough. Dizziness. Headache. Nausea. Sore throat. Vomiting.

Redness. Numbness.

Redness. Pain.

See Inhalation.

irritation eyes, skin, nose, throat; headache, dizziness; dermatitis; liver, kidney damage

Effluent ConcentrationsDiisobutyl ketone has been qualitatively detected in wastewater effluent concentrates collected from an advanced wastewater treatment facility in Pomona, CA in Sept 1974(1).
Medical Surveillance · 2 Einträge

Pulmonary function tests

Consider the points of attack /resp system, skin, eyes/ in placement and periodic physical exam.

Soil Adsorption/Mobility · 1 Eintrag

The Koc of diisobutyl ketone is estimated as 57(SRC), using a water solubility of 2,640 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diisobutyl ketone is expected to have high mobility in soil.

Human Toxicity Excerpts · 5 Einträge

/HUMAN EXPOSURE STUDIES/ ... The sensory response of humans to diisobutyl ketone vapors /was studied/ ... concn higher than 25 ppm had an objectionable odor and caused eye irritation.

/SIGNS AND SYMPTOMS/ DIISOBUTYL KETONE HAS A LOW DEGREE OF HAZARD IN INDUSTRIAL HANDLING. IT HAS A LOW ACUTE ORAL TOXICITY. WHEN IN CONTACT WITH THE EYES, IT SHOULD CAUSE NO MORE THAN MINOR IRRITATION. SKIN CONTACT WITH THE LIQUID MAY RESULT IN MILD IRRITATION OR EVEN A DERMATITIS DEPENDING UPON TYPE AND DURATION OF CONTACT. VAPORS, IN HIGH CONCN, EXERT BOTH IRRITANT & ... /CNS DEPRESSION/ ACTION. HUMANS FIND CONCN BELOW THOSE CAUSING ... /CNS DEPRESSION/ IN ANIMALS TO BE SUFFICIENTLY IRRITATING & DISCOMFORTING TO BE OFFENSIVE.

/SIGNS AND SYMPTOMS/ BECAUSE OF ITS HIGH FAT SOLVENCY IT IS SUSPECTED THAT FREQUENTLY REPEATED SKIN CONTACTS MAY CAUSE A DERMATITIS.

/CASE REPORTS/ A group of 12 volunteers was exposed for 15 minutes to DIBK vapor. Most individuals reported eye irritation at 50 ppm. 25 ppm was the concentration that most individuals reported as acceptable for 8 hour exposure.

/CASE REPORTS/ ... TWO MALE SUBJECTS WHO INHALED 50 PPM FOR 3 HR NOTED SLIGHT TRANSITORY IRRITATION OF MUCOUS MEMBRANES AT BEGINNING OF EXPOSURE. ... SLIGHT IRRITATION OF EYES & NOSE WAS NOTED BY 3 SUBJECTS EXPOSED TO 100 PPM, WITH SLIGHT LACRIMATION ... HEADACHE, & DIZZINESS ON RETURNING TO FRESH AIR.

Regulatorische Informationen

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

Formulations/PreparationsGrade: Technical
Household ProductsInformation on 2 consumer products that contain 2,6-dimethylheptan-4-one; di-isobutyl ketone in the following categories is provided:
Use Classification · 3 Einträge

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 3 Einträge

Wholesale and Retail Trade

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

Diisobutyl ketone has been detected at a concn of 10 percent in a commercially available paint stripper solvent.