METHYL ISOBUTYL KETONE

synonyms:
4-Methyl-2-pentanone; Isopropylacetone; Hexone; Isobutyl methyl ketone; 2-Methylpropyl methyl ketone; 4-Methyl-2-oxopentane; MIK; Isobutylmethyl ketone; MIBK; Isohexanone; 4-Methyl-2-pentanone; METHYL ISOBUTYL KETONE; 4-Methylpentan-2-one; 108-10-1; Isopropylacetone; Isobutyl methyl ketone; Hexone; 2-Pentanone, 4-methyl-; MIBK; 2-Methyl-4-pentanone; 4-Methyl-2-oxopentane; Methylisobutylketon; Isohexanone; Hexon; Shell mibk; Metilisobutilchetone; Metyloizobutyloketon; 2-Methylpropyl methyl ketone; Isobutyl-methylketon; Methyl-isobutyl-cetone; 4-Methyl-2-pentanon; 4-Metilpentan-2-one; Isopropyl acetone; Ketone, isobutyl methyl; 4-Methyl-pentan-2-on; 4-Methyl-pentan-2-one; Hexon [Czech]; Rcra waste number U161; methylisobutyl ketone; Caswell No. 574AA; FEMA Number 2731; UNII-U5T7B88CNP; NSC 5712; methylisobutylketone; Isobutyl-methylketon [Czech]; Metyloizobutyloketon [Polish]; methyl isobutylketone; Metilisobutilchetone [Italian]; 4-Methyl-2-pentanon [Czech]; FEMA No. 2731; METHYL ISO-BUTYL KETONE; CCRIS 2052; HSDB 148; Methyl-isobutyl-cetone [French]; 2-Methyl-4-pentanal; 4-Metilpentan-2-one [Italian]; Methyl I-butyl ketone; ethyl iso-butyl ketone; 4-Methyl-2-pentanone (natural); Methylisobutylketon [Dutch, German]; EINECS 203-550-1; UN1245; RCRA waste no. U161; EPA Pesticide Chemical Code 044105; BRN 0605399; U5T7B88CNP; 4-Methyl-pentan-2-on [Dutch, German]; Methyl isobutyl ketone [NF]; AI3-01229; CHEBI:82344; MFCD00008938; Methyl isobutyl ketone (NF); MIK; 4-Methyl-2-pentanone, >=99%; isobutylmethyl ketone; 4-Methyl-2-pentanone, 99.5%, for analysis; 4-Methyl-2-pentanone, 98.5+%, ACS reagent; 2-Pentanone,4-methyl-; 4-Methyl-2-pentanone, 99.5%, spectrophotometric grade; 4-Methyl-2-pentanone, 99+%, electronic use grade, residue free; Methyl isobutyl ketone [USAN]; methylisobutyketone; isobutylmethylketone; methylisobutlyketone; i-BuCOMe; methylisobutyl keton; methylisobutyl-keton; Methylpentan-2-one; iso-butylmethylketone; methyl-isobutylketone; 4-methyl-2pentanone; methy isobutyl ketone; methyl isobutyl keton; methyl iso-butylketone; methyl-iso-butylketone; methyl-isobutyl ketone; 4-methylpentane-2-one; iso-C4H9COCH3; Methyl-2-pentanon,4-; 4-methyl- 2-pentanone; metil izobütil keton; metıl ızobutil keton; metil izobutil keton

METHYL ISOBUTYL KETONE

Methyl isobutyl ketone

Methyl isobutyl ketone
Skeletal formula of methyl isobutyl ketone
Ball-and-stick model of the methyl isobutyl ketone molecule
Names
Preferred IUPAC name
4-Methylpentan-2-one
Other names
4-Methyl-2-pentanone, Isopropylacetone, Hexone, Isobutyl methyl ketone, 2-Methylpropyl methyl ketone, 4-Methyl-2-oxopentane, MIK, Isobutylmethyl ketone, MIBK, Isohexanone
Identifiers
CAS Number    
108-10-1 check
3D model (JSmol)    
Interactive image
ChemSpider    
7621 ☒
ECHA InfoCard    100.003.228 
EC Number    
203-550-1
KEGG    
C19263 check
PubChem CID    
7909
RTECS number    
SA9275000
UNII    
U5T7B88CNP ☒
CompTox Dashboard (EPA)    
DTXSID5021889 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    C6H12O
Molar mass    100.16 g/mol
Appearance    colorless liquid
Odor    pleasant[1]
Density    0.802 g/mL, liquid
Melting point    −84.7 °C (−120.5 °F; 188.5 K)
Boiling point    117 to 118 °C (243 to 244 °F; 390 to 391 K)
Solubility in water    1.91 g/100 mL (20 °C)
Vapor pressure    16 mmHg (20 °C)[1]
Magnetic susceptibility (χ)    -70.05·10−6 cm3/mol
Refractive index (nD)    1.3958
Viscosity    0.58 cP at 20.0 °C
Structure
Dipole moment    2.8 D
Hazards
EU classification (DSD) (outdated)    Flammable (F)
Harmful (Xn)
R-phrases (outdated)    R11, R20, R36/37, R66
S-phrases (outdated)    (S2), S9, S16, S29
NFPA 704 (fire diamond)    
NFPA 704 four-colored diamond
32
Flash point    14 °C (57 °F; 287 K)
Autoignition
temperature    449 °C (840 °F; 722 K)
Explosive limits    1.2–8.0% (93 °C)[1]
NIOSH (US health exposure limits):
PEL (Permissible)    TWA 100 ppm (410 mg/m3)[1]
REL (Recommended)    TWA 50 ppm (205 mg/m3) ST 75 ppm (300 mg/m3)[1]
IDLH (Immediate danger)    500 ppm[1]
Related compounds
Related ketones    Methyl isopropyl ketone
2-Pentanone
Diisobutyl ketone
Related compounds    2-Methylpentan-4-ol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒ verify (what is check☒ ?)
Infobox references
Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.[2]

Production
Methyl isobutyl ketone is made from acetone via a three-step process. Firstly acetone undergoes an aldol reaction to give diacetone alcohol, which readily dehydrates to give mesityl oxide. Mesityl oxide can then be hydrogenated to give MIBK:

Synthesis of Methyl isobutyl ketone from acetone
Industrially, these three steps are combined. Acetone is treated with a strong acidic, palladium-doped cation exchange resin under medium pressure of hydrogen.[3] Several million kilograms are produced annually.[4] In 2003, the industrial production capacity for Methyl isobutyl ketone in the United States was 88,000 tons.[5]

Uses

Methyl isobutyl ketone tank car in Europe.
Methyl isobutyl ketone is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.[4]

Precursor to 6PPD
Another major use is as a precursor to N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene diamine (6PPD), an antiozonant used in tires. 6PPD is prepared by reductive coupling of Methyl isobutyl ketone with 4-aminodiphenylamine.[6]

Solvent and niche applications
Unlike the other common ketone solvents, acetone and MEK, Methyl isobutyl ketone has quite low solubility in water, making it useful for liquid-liquid extraction. It has a similar polarity to ethyl acetate, but greater stability towards aqueous acid and base. It can be used to extract gold, silver and other precious metals from cyanide solutions, such as those found at gold mines, to determine the levels of those dissolved metals. Diisobutyl ketone (DIBK), a related lipophilic ketone, is also used for this purpose. Methyl isobutyl ketone is also used as a denaturing agent for denatured alcohol. When mixed with water or isopropyl alcohol Methyl isobutyl ketone serves as a developer for PMMA electron beam lithography resist. Methyl isobutyl ketone is used as a solvent for CS in the preparation of the CS spray used currently by British police forces.

Molecular Weight of Methyl isobutyl ketone:    100.16 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3    1.3    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Methyl isobutyl ketone:    0    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Methyl isobutyl ketone:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Methyl isobutyl ketone:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Methyl isobutyl ketone:    100.088815 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Methyl isobutyl ketone:    100.088815 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Methyl isobutyl ketone:    17.1 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Methyl isobutyl ketone:    7    Computed by PubChem
Formal Charge of Methyl isobutyl ketone:    0    Computed by PubChem
Complexity of Methyl isobutyl ketone:    64.6    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Methyl isobutyl ketone:    0    Computed by PubChem
Defined Atom Stereocenter Count of Methyl isobutyl ketone:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Methyl isobutyl ketone:    0    Computed by PubChem
Defined Bond Stereocenter Count of Methyl isobutyl ketone:    0    Computed by PubChem
Undefined Bond Stereocenter Count of Methyl isobutyl ketone:    0    Computed by PubChem
Covalently-Bonded Unit Count of Methyl isobutyl ketone:    1    Computed by PubChem
Compound  of Methyl isobutyl ketone Is Canonicalized    Yes

 Methyl Isobutyl Ketone (MIBK) - part of our Ketones range of high purity oxygenated chemical solvents.  Methyl isobutyl ketone is an active solvent with excellent dissolving characteristics, a high tolerance to other hydrocarbon diluents and a medium evaporation rate.

Ketones are strong polar solvents thanks to their carbonyl functional group. Their high solvency and excellent stability make them a solvent of choice for coatings, adhesives, inks and cleaning applications.

Methyl isobutyl ketone is a ‘true’ or active solvent due to its compatibility with a variety of organic components and its ability to dissolve them on its own without the need for an alcohol, which can help to simplify system formulations. It also has the ability to combine with lower-cost hydrocarbon solvents in solvent blends.

Methyl isobutyl ketone is a colourless liquid with a stable chemical nature and a medium boiling range. It is able to dissolve cellulose esters, vinyl polymers and copolymers, and most natural and synthetic resins and is also partially miscible in water.

Its relatively low density combined with strong solvency assists coatings formulators in producing high-quality, high-solids formulations that are also able to comply with VOC regulations.  

Because of its high solvent strength, less solvent is required to dissolve a resin and in applications where the solvent evaporates to the atmosphere during use, lower levels of VOC emissions are produced.

Hazard Summary 
Methyl isobutyl ketone is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.  Acute (short-term) exposure to methyl isobutyl ketone may irritate the eyes and mucous membranes, and cause weakness, headache, nausea, lightheadedness, vomiting, dizziness, incoordination, narcosis in humans.  Chronic (long-term) occupational exposure to methyl isobutyl ketone has been observed to cause nausea, headache, burning in the eyes, weakness, insomnia, intestinal pain, and slight enlargement of the liver in humans.  Lethargy and kidney and liver effects have been observed in rats and mice chronically exposed by gavage (experimentally placing the chemical in the stomach), ingestion, and inhalation.  EPA has classified methyl isobutyl ketone as a Group D, not classifiable as to human carcinogenicity.
 Uses 
Methyl isobutyl ketone is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose, as an alcohol denaturant, in the extraction of rare metals, and as a synthetic flavoring adjuvant. (1,3,9) 
Sources and Potential Exposure
 Occupational exposure may occur in the workplace by the inhalation of vapors and by skin and eye contact. (1) The most probable routes of exposure to methyl isobutyl ketone by the general population are by inhalation and dermal contact during the use of consumer products that contain this compound. (1) Methyl isobutyl ketone may be released to the environment in effluent and emissions from its manufacture and use, in exhaust gas from vehicles, and from land disposal and ocean dumping of waste that contains this compound.  Since methyl isobutyl ketone is a solvent and denaturant with a wide variety of applications, a large number of industries could potentially release this compound.  Some segments of the population may be exposed by the inhalation of contaminated air or by the ingestion of contaminated drinking water.

Methyl isobutyl ketone is used as a chemical intermediate, a solvent for manufacturing paints, rubbers, pharmaceuticals, other chemicals, and industrial cleaners. It is used in the semiconductor industry. Methyl isobutyl ketone is very efficient at dissolving resins used in paints, inks, lacquers, and other types of surface coatings. Synonyms for Methyl isobutyl ketone are hexone, isobutyl methyl ketone, and isohexanone. Methyl isobutyl ketone is a Food and Drug Administration (FDA)-approved indirect food additive for adhesives, paper and paperboard, and polymers.