Methyl isobutyl ketone

Base Information

• Chemical Name: Methyl isobutyl ketone
• CAS No.: 108-10-1
• Deprecated CAS: 1338234-91-5
• Molecular Formula: C6H12O
• Molecular Weight: 100.161
• Hs Code.: 2914.13 Oral rat LD50; 2737 mg/kg
• European Community (EC) Number: 203-550-1
• ICSC Number: 0511
• NSC Number: 5712
• UN Number: 1245
• UNII: U5T7B88CNP
• DSSTox Substance ID: DTXSID5021889
• Nikkaji Number: J2.861D
• Wikipedia: Methyl_isobutyl_ketone
• Wikidata: Q418104
• RXCUI: 1362929
• Metabolomics Workbench ID: 5439
• ChEMBL ID: CHEMBL285323
• Mol file: 108-10-1.mol

Synonyms:4-methyl-2-pentanone;isobutyl methyl ketone;isopropylacetone;methyl isobutyl ketone

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Chemical Property of Methyl isobutyl ketone

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 15 mm Hg ( 20 °C)
• Melting Point: -84 °C
• Refractive Index: 1.3962
• Boiling Point: 116.5 °C at 760 mmHg
• Flash Point: 13.3 °C
• PSA: 17.07000
• Density: 0.7978 g/cm³
• LogP: 1.62150
• Storage Temp.: 2-8°C
• Solubility.: water: soluble20g/L
• Water Solubility.: 17 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 100.088815002
• Heavy Atom Count: 7
• Complexity: 64.6
• Transport DOT Label: Flammable Liquid

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn,T
• Hazard Codes: F,Xn,T
• Statements: 11-20-36/37-66-39/23/24/25-23/24/25
• Safety Statements: 9-16-29-45-36/37-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC(C)CC(=O)C
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance and the vapour are irritating to the eyes, skin and respiratory tract. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the central nervous system at high concentrations. This may result in narcosis.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Description: 4-Methyl-2-pentanone has a pleasant odor. May be prepared by hydrogenation of mesityl oxide over Ni at 160 - 190°C; also by oxidation of methyl isobutyl carbinol.
• Physical properties: Clear, colorless, watery liquid with a mild, pleasant odor. Odor threshold concentration is 47 ppbv (Leonardos et al., 1969). Experimentally determined detection and recognition odor threshold concentrations were 400 μg/m3 (100 ppbv) and 1.1 mg/m3 (270 ppbv), respectively (Hellman and Small, 1974).
• Uses: MIBK is used as a solvent for gums, resins,nitrocellulose and cellulose ethers, and various fats, oils, and waxes. In paints, glues, and cleaning agents; used in the plastic and petrol industries Methyl isobutyl ketone (hexone, isobutyl methyl ketone, 4-methyl-2-pentanone) is an organic solvent similar in structure and use to methyl butyl ketone. In addition to its use as a solvent for paints, lacquers, and varnishes, methyl isobutyl ketone is used in extraction processes and as a denaturant for rubbing alcohol. Methyl isobutyl ketone is also used as a synthetic flavoring in some varieties of rum, candy, and cheese. Unlike methyl butyl ketone, methyl isobutyl ketone has not been found to occur naturally.

Technology Process of Methyl isobutyl ketone

There total 199 articles about Methyl isobutyl ketone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-Methyl-1-pentene (691-37-2,25068-26-2) → 4-methylpent-2-enal (5362-56-1) + isocaproic aldehyde (1119-16-0) + 4-methyl-2-pentanone (108-10-1)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); oxygen; p-benzoquinone; copper(l) chloride; In water; tert-butyl alcohol; at 40 ℃; for 6h; under 760.051 Torr; regioselective reaction;

DOI:10.1002/cctc.202000472

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + 2-(1-hydroxy-1,3-dimethyl-butyl)-2-methyl-succinic acid dimethyl ester → 2-methylbutanedioic acid (498-21-5,636-60-2) + 4-methyl-2-pentanone (108-10-1)

Guidance literature:

Reference yield:

pentane (109-66-0,8031-35-4,9078-70-0) → 2-methyl-but-2-ene (513-35-9) + 4-methyl-pent-3-en-2-one (141-79-7) + Isobutane (75-28-5,40921-86-6) + 2-Methyl-1-butene (563-46-2) + 5-Methyl-2-hexanone (110-12-3) + 4-methyl-2-pentanone (108-10-1)

Guidance literature:

With CH₃COCl*2AlBr₃; In neat (no solvent); at 20 ℃; for 0.5h; Product distribution; other n-alkanes C₆-C₁₂, C₁₈, other reagent;

upstream raw materials:

diazomethane

isovaleraldehyde

methanol

2-methyl-6-methylene-7-octene-4-one

Downstream raw materials:

2,2-bis(4-hydroxy-3-methylphenyl)-4-methylpentane

(+/-)-1-hydroxy-5-methyl-1-phenyl-3-hexanone

1-Phenyl-3-hydroxy-7-methyl-octan-5-on

2-amino-6-isobutyl-4-phenylnicotinonitrile

Refernces

• 1、 Hetterley, Robert D.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.. "Multifunctional catalysis by Pd-polyoxometalate: One-step conversion of acetone to methyl isobutyl ketone". . p. 782 - 784. Retrieved 2006.
• 2、 Elmorsy, Saad S.,El-Ahl, Abdel-Aziz S.,Soliman, Hanan,Amer, Fathy A.. "Use of reductive properties of iodotrichlorosilane II: Chemoselective reduction of α,β-unsaturated ketones and nitriles". . p. 2297 - 2298. Retrieved 1996.
• 3、 Dauben et al.. "-". . p. 1849. Retrieved 1969.
• 4、 Shchelkunov,Mazakova,Bekenova,Amirkhanova,Shchelkunov. "Chemical aspects of electrocatalytic reduction of carbonyl compounds. Mesityl oxide". . p. 446 - 447. Retrieved 2001.
• 5、 Baranger, Anne M.,Walsh, Patrick J.,Bergman, Robert G.. "Variable regiochemistry in the stoichiometric and catalytic hydroamination of alkynes by imidozirconium complexes caused by an unusual dependence of the rate law on alkyne structure and temperature". . p. 2753 - 2763. Retrieved 1993.
• 6、 Ho, Christopher R.,Zheng, Steven,Shylesh, Sankaranarayanapillai,Bell, Alexis T.. "The mechanism and kinetics of methyl isobutyl ketone synthesis from acetone over ion-exchanged hydroxyapatite". . p. 174 - 183. Retrieved 2018.
• 7、 Hartman, J. W.,Hiscox, W. C.,Jennings, P. W.. "Catalytic Hydration of Alkynes with Platinum(II) Complexes". . p. 7613 - 7614. Retrieved 1993.
• 8、 Adkins,Kutz,Coffman. "-". . p. 3212,3217. Retrieved 1930.
• 9、 Petrow,Kupin. "". . p. 3153; engl.Ausg.S.3122. Retrieved 1959.
• 10、 Fahey,Lee. "-". . p. 2124. Retrieved 1968.