Methyl isobutyl ketone

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]

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.228
EC Number 203-550-1
KEGG
RTECS number SA9275000
UNII
Properties
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)
1.91 g/100 mL (20 °C)
Vapor pressure 16 mmHg (20 °C)[1]
-70.05·10−6 cm3/mol
1.3958
Viscosity 0.58 cP at 20.0 °C
Structure
2.8 D
Hazards
Flammable (F)
Harmful (Xn)
R-phrases (outdated) R11, R20, R36/37, R66
S-phrases (outdated) (S2), S9, S16, S29
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
Flash point 14 °C (57 °F; 287 K)
449 °C (840 °F; 722 K)
Explosive limits 1.2%-8.0% (93 °C)[1]
US health exposure limits (NIOSH):
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).

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 MIBK from acetone
Synthesis of MIBK 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 MIBK in the United States was 88,000 tons.[5]

Uses

Kesselwagen 2 dez-08
MIBK tank car in Europe.

MIBK 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 MIBK with 4-aminodiphenylamine.[6]

Solvent and niche applications

Unlike the other common ketone solvents, acetone and MEK, MIBK 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 MIBK serves as a developer for PMMA electron beam lithography resist. MIBK is used as a solvent for CS in the preparation of the CS spray used currently by British police forces.[7]

References

  1. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0326". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ US EPA. "Methyl Isobutyl Ketone (Hexone)". Retrieved 13 December 2015.
  3. ^ [1], Uhde Technology Profile: MIBK
  4. ^ a b Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  5. ^ International Agency for Research on Cancer. "Methyl Isobutyl Ketone" (PDF). Retrieved 13 December 2015.
  6. ^ Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and Additives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a23_365.pub2
  7. ^ Peter J Gray; Stark, MM; Gray, P. J; Jones, G R. N (2000). "Is CS spray dangerous? : CS is a particulate spray, not a gas" (Response to editorial). BMJ. 321 (7252): 26. doi:10.1136/bmj.321.7252.46. PMC 1127688. PMID 10939811.

External links

Bohemic acid

Bohemic acid is a mixture of chemical compounds which is obtained through fermentation by actinobacteria species in the genus Actinosporangium (Actinoplanaceae). The name honors the Puccini opera La Bohème and many individual components of the acid carry the names of characters from La Bohème. Most of those components are antitumor agents and anthracycline antibiotics active against Gram-positive bacteria.

C6H12O

The molecular formula C6H12O may refer to:

Cyclohexanol

Cyclopentyl methyl ether

Hexanal

2-Hexanone

3-Hexanone

cis-3-Hexen-1-ol

Methyl isobutyl ketone

3-Methyl-2-pentanone

Oxepane

Pinacolone

Chemical Agent Resistant Coating

Chemical Agent Resistant Coating is a paint commonly applied to military vehicles to provide protection against chemical and biological weapons.The surface of the paint is engineered to be easily decontaminated after exposure to chemical warfare and biological warfare agents. The paint is also resistant to damage and removal by decontaminating solutions. Two-component systems (e.g. epoxy or polyester-based) are often employed. This coating is described in MIL-DTL-53072E.

Denatured alcohol

Denatured alcohol, also called methylated spirit (in Australia, New Zealand, South Africa and the United Kingdom) or denatured rectified spirit, is ethanol that has additives to make it poisonous, bad-tasting, foul-smelling, or nauseating to discourage recreational consumption. It is sometimes dyed. Pyridine, methanol, or both can be added to make denatured alcohol poisonous, and denatonium can be added to make it bitter.

Denatured alcohol is used as a solvent and as fuel for alcohol burners and camping stoves. Because of the diversity of industrial uses for denatured alcohol, hundreds of additives and denaturing methods have been used. The main additive has traditionally been 10% methanol, giving rise to the term "methylated spirits". Other typical additives include isopropyl alcohol, acetone, methyl ethyl ketone, methyl isobutyl ketone, and denatonium.In the United States, mixtures sold as denatured alcohol often have much greater percentages of methanol, and can be less than 50% ethanol.

Denaturing alcohol does not chemically alter the ethanol molecule. Rather, the ethanol is mixed with other chemicals to form a toxic or bad tasting solution. For many of these solutions, there is no practical way to separate the components.

Diacetone alcohol

Diacetone alcohol is a chemical compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.

It occurs naturally in Achnatherum robustum.

Drug precursors

A drug precursor is a substance which can be used to make illicit drugs.

Examples of such precursors and drugs made with them are listed below.

Hexanone

Hexanone may refer to the following ketones containing six carbon atoms:

2-Hexanone (Methyl butyl ketone, MBK)

4-Methyl-2-pentanone (Methyl isobutyl ketone, MIBK)

3-Methyl-2-pentanone (Methyl sec-butyl ketone)

3,3-Dimethyl-2-butanone (Methyl tert-butyl ketone, Pinacolone)

3-Hexanone (Ethyl propyl ketone)

2-Methyl-3-pentanone (Ethyl isopropyl ketone)

Hilmi İbar

Hilmi İbar (Serbian Cyrillic: Хилми Ибар) (born July 31, 1947 in Gnjilane, FPR Yugoslavia) is Professor of Chemistry, former Dean of the pedagogic Faculty and former Head of the International Office at the Trakya University in Edirne. He is also Vicepresident of the Balkan Universities Network.

Kumho Petrochemical

Kumho Petrochemical Co., Ltd. (Korean: 금호석유화학, KKPC) is multinational chemical company based in South Korea, with headquarters in Seoul. It was founded in 1970 when Kumho Group struggled to secure raw materials for its bus and tire businesses. Kumho Petrochemical has a global market leadership in the manufacturing of synthetic rubbers with the world's largest production capacity based on SBR and BR by IISRP 2012. It focuses on synthetic rubbers, synthetic resins, specialty chemicals, electronic chemicals, energy, building materials and advanced materials as its core business.In 2011, Kumho Petrochemical was ranked at 1806th of 'the Global 2000' by Forbes. In 2013, it became a component of the KOSPI 100 index, which tracks 100 major companies listed on the Korea Stock Exchange.It changed its name from 'Korea Kumho Petrochemical' to 'Kumho Petrochemical' effective February 15, 2012.It was spun off from Kumho Asiana Group in December 2015.

List of IARC Group 2B carcinogens

Substances, mixtures and exposure circumstances in this list have been classified by the International Agency for Research on Cancer (IARC) as Group 2B: The agent (mixture) is "possibly carcinogenic to humans". The exposure circumstance entails exposures that are possibly carcinogenic to humans. This category is used for agents, mixtures and exposure circumstances for which there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is inadequate evidence of carcinogenicity in humans but there is sufficient evidence of carcinogenicity in experimental animals. In some instances, an agent, mixture or exposure circumstance for which there is inadequate evidence of carcinogenicity in humans but limited evidence of carcinogenicity in experimental animals together with supporting evidence from other relevant data may be placed in this group.

Further details can be found in the preamble to the IARC Monographs.

List of UN numbers 1201 to 1300

The UN numbers from UN1201 to UN1300 as assigned by the United Nations Committee of Experts on the Transport of Dangerous Goods.

Mesityl oxide

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

National Pollutant Inventory

The National Pollutant Inventory (NPI) is a database of Australian pollution emissions managed by the Australian Commonwealth, State and Territory Governments. A condensed version of the information collected is available to the public via the NPI website www.npi.gov.au.

Rubbing alcohol

Rubbing alcohol refers to either isopropyl alcohol (propan-2-ol) or ethanol based liquids, or the comparable British Pharmacopoeia defined surgical spirit, with isopropyl alcohol products being the most widely available. Rubbing alcohol is undrinkable even if it is ethanol based, due to the bitterants added.

They are liquids used primarily as a topical antiseptic.

They also have many industrial and household uses. The term "rubbing alcohol" has become a general non-specific term for either isopropyl alcohol (isopropanol) or ethyl alcohol (ethanol) rubbing-alcohol products.

The United States Pharmacopeia defines 'isopropyl rubbing alcohol USP' as containing approximately 70 percent by volume of pure isopropyl alcohol and

defines 'rubbing alcohol USP' as containing approximately 70 percent by volume of denatured alcohol. In Ireland and the UK, the comparable preparation is surgical spirit B.P., which the British Pharmacopoeia defines as 95% methylated spirit, 2.5% castor oil, 2% diethyl phthalate, and 0.5% methyl salicylate.

Under its alternative name of "wintergreen oil", methyl salicylate is a common additive to North American rubbing alcohol products. Individual manufacturers are permitted to use their own formulation standards in which the ethanol content for retail bottles of rubbing alcohol is labeled as and ranges from 70-99% v/v.All rubbing alcohols are unsafe for human consumption: isopropyl rubbing alcohols do not contain the ethyl alcohol of alcoholic beverages; ethyl rubbing alcohols are based on denatured alcohol, which is a combination of ethyl alcohol and one or more bitter poisons that make the substance toxic.

Sanford L.P.

Sanford L.P. is a Newell Brands company based in Oak Brook, Illinois, United States. It is the largest writing products manufacturer in the world. It is primarily known for manufacturing Sharpie, Paper Mate, and Prismacolor products.

Sodium tetradecyl sulfate

Sodium tetradecyl sulfate (STS) is a commonly used synonym for 7-ethyl-2-methyl-4-undecanyl sulfate sodium salt which is anionic surfactant that is the active component of the sclerosant drug Sotradecol. It is commonly used in the treatment of varicose and spider veins of the leg, during the procedure of sclerotherapy. Being a detergent, its action is on the lipid molecules in the cells of the vein wall, causing inflammatory destruction of the internal lining of the vein and thrombus formation eventually leading to sclerosis of the vein. It is used in concentrations ranging from 0.1% to 3% for this purpose.

In the UK, Ireland, Italy, Australia, New Zealand and South Africa, it is sold under the trade-name Fibro-Vein in concentrations of 0.2%, 0.5%, 1.0%, and 3%.

Solvent

A solvent (from the Latin solvō, "loosen, untie, solve") is a substance that dissolves a solute (a chemically distinct liquid, solid or gas), resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. The quantity of solute that can dissolve in a specific volume of solvent varies with temperature. Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as paint thinners (e.g. toluene, turpentine), as nail polish removers and glue solvents (acetone, methyl acetate, ethyl acetate), in spot removers (e.g. hexane, petrol ether), in detergents (citrus terpenes) and in perfumes (ethanol). Water is a solvent for polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within a cell. Solvents find various applications in chemical, pharmaceutical, oil, and gas industries, including in chemical syntheses and purification processes.

Urea extraction crystallization

The urea extraction crystallization is a process for separating linear paraffins (n-paraffins, n-alkanes) from hydrocarbon mixtures through the formation of urea-n-paraffin-clathrates. The process is primarily used to lower the pour point of petroleum products, by-products of the process are n-paraffins in high purity. The method may also applied for the separation of fatty acids and fatty alcohols. In addition to urea also thiourea is used in the process.

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