メチルイソブチルケトン
WordNet
- any of a class of organic compounds having a carbonyl group linked to a carbon atom in each of two hydrocarbon radicals
- the univalent radical CH3- derived from methane (同)methyl_group, methyl radical
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/05 06:45:25」(JST)
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Methyl isobutyl ketone
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| Names |
| IUPAC name
4-Methyl-2-pentanone
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| Other names
Isopropylacetone, Hexone, Isobutyl methyl ketone, 4-Methylpentan-2-one, 4-methyl-2-pentanone, 2-methyl-4-pentanone, 2-methylpropyl methyl ketone, 4-methyl-2-oxopentane, MIK, isobutylmethyl ketone, MIBK, isohexanone
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| Identifiers |
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CAS Number
|
108-10-1 N |
| ChemSpider |
7621 N |
| EC Number |
203-550-1 |
InChI
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InChI=1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 N
Key: NTIZESTWPVYFNL-UHFFFAOYSA-N N
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InChI=1/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3
Key: NTIZESTWPVYFNL-UHFFFAOYAQ
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| Jmol interactive 3D |
Image |
| KEGG |
C19263 Y |
| PubChem |
7909 |
| RTECS number |
SA9275000 |
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| Properties |
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Chemical formula
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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) |
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Solubility in water
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1.91 g/100 mL (20 °C) |
| Vapor pressure |
16 mmHg (20 °C)[1] |
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Refractive index (nD)
|
1.3958 |
| Viscosity |
0.58 cP at 20.0 °C |
| Structure |
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Dipole moment
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2.8 D |
| Hazards |
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EU classification (DSD)
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Flammable (F)
Harmful (Xn) |
| R-phrases |
R11, R20, R36/37, R66 |
| S-phrases |
(S2), S9, S16, S29 |
| NFPA 704 |
|
| 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] |
| US health exposure limits (NIOSH): |
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PEL (Permissible)
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TWA 100 ppm (410 mg/m3)[1] |
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REL (Recommended)
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TWA 50 ppm (205 mg/m3) ST 75 ppm (300 mg/m3)[1] |
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IDLH (Immediate danger
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500 ppm[1] |
| Related compounds |
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Related ketones
|
Methyl isopropyl ketone
2-Pentanone
Diisobutyl ketone |
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Related compounds
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2-Methylpentan-4-ol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is YN ?) |
| Infobox references |
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Methyl isobutyl ketone (MIBK) is the organic compound with the formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is widely used as a solvent.
Contents
- 1 Production
- 2 Uses
- 2.1 Precursor to 6PPD
- 2.2 Solvent and niche applications
- 3 References
- 4 External links
Production
Methyl isobutyl ketone is manufactured from acetone via a three-step process. Firstly acetone undergoes an aldol condensation to give diacetone alcohol, which readily dehydrates to give mesityl oxide. Mesityl oxide can then be hydrogenated to give MIBK:
Modern processes combine these three steps into one.[2]
Several million kilograms are produced annually.[3]
Uses
MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.[3]
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.[4]
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.[5]
References
- ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0326". National Institute for Occupational Safety and Health (NIOSH).
- ^ [1], Uhde Technology Profile: MIBK
- ^ a b Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
- ^ 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
- ^ 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
- International Chemical Safety Card 0511
- National Pollutant Inventory - Methyl isobutyl ketone fact sheet
- NIOSH Pocket Guide to Chemical Hazards
UpToDate Contents
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English Journal
- Pretreatment of Eucalyptus in biphasic system for furfural production and accelerated enzymatic hydrolysis.
- Zhang X1, Bai Y2, Cao X2, Sun R3.
- Bioresource technology.Bioresour Technol.2017 Aug;238:1-6. doi: 10.1016/j.biortech.2017.04.011. Epub 2017 Apr 7.
- PMID 28432947
- Potential impact of methyl isobutyl ketone (MIBK) on phenols degradation in an UASB reactor and its degradation properties.
- Wang W1, Yang K2, Sierra JM3, Zhang X3, Yuan S2, Hu Z4.
- Journal of hazardous materials.J Hazard Mater.2017 Jul 5;333:73-79. doi: 10.1016/j.jhazmat.2017.03.033. Epub 2017 Mar 18.
- PMID 28342357
- Determination of phospholipids in soybean lecithin samples via the phosphorus monoxide molecule by high-resolution continuum source graphite furnace molecular absorption spectrometry.
- Pires LN1, Brandão GC2, Teixeira LS3.
- Food chemistry.Food Chem.2017 Jun 15;225:162-166. doi: 10.1016/j.foodchem.2017.01.019. Epub 2017 Jan 5.
- PMID 28193410
Japanese Journal
- Water /Methyl isobutyl ketone (MIBK) Biphasic System in Slug Flow under High Temperature and Pressure Conditions
- SHIMANOUCHI Toshinori,TANIFUJI Tatsuya,FUJIOKA Satoko [他]
- Solvent extraction research and development, Japan 21, 201-209, 2014
- NAID 40020056669
- Study of Development Processes for ZEP-520 as a High-Resolution Positive and Negative Tone Electron Beam Lithography Resist
- Mohammad Mohammad Ali,Koshelev Kirill,Fito Taras [他],Zheng David Ai Zhi,Stepanova Maria,Dew Steven
- Jpn J Appl Phys 51(6), 06FC05-06FC05-8, 2012-06-25
- … In this work, we investigate the development of ZEP-520 resist through contrast curves, dense gratings, and surface roughness measurements using three different classes of developer systems of varying solvation strength, ZED-N50, methyl isobutyl ketone (MIBK) : isopropyl alcohol (IPA) 1:3, and IPA : H2O 7:3, at the ambient temperature (22 °C) and cold (-15 °C) development conditions. …
- NAID 150000104129
- Effect of organic cations and solvents on the ion-pair extraction of boric acid with salicyl alcohol
- Morita Keisuke,Hirayama Naoki,Morita Kotaro [他],Imura Hisanori
- Solvent Extraction Research and Development 18, 199-203, 2011
- … methyl isobutyl ketone for TOMAC1. …
- NAID 120005302295
★リンクテーブル★
[★]
- 英
- methyl isobutyl ketone, MIBK
- 同
- イソブチルメチルケトン isobutyl methyl ketone、イソプロピルアセトン isopropylacetone
- 関
- 有機溶剤中毒予防規則