イソプロピルアセトン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/21 22:59:52」(JST)
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| Methyl isobutyl ketone |
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Other names
Isopropylacetone, Hexone, Isobutyl methyl ketone, 4-Methylpentan-2-one, 4-methyl-2-pentanone, 4-methylpentan-2-one, 2-methyl-4-pentanone, 2-methylpropyl methyl ketone, 4-methyl-2-oxopentane, MIK, isobutylmethyl ketone, MIBK, isohexanone
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| Identifiers |
| CAS number |
108-10-1 Y |
| PubChem |
7909 |
| ChemSpider |
7621 N |
| EC number |
203-550-1 |
| KEGG |
C19263 Y |
| RTECS number |
SA9275000 |
| Jmol-3D images |
Image 1 |
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InChI=1S/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3 N
Key: NTIZESTWPVYFNL-UHFFFAOYSA-N N
InChI=1/C6H12O/c1-5(2)4-6(3)7/h5H,4H2,1-3H3
Key: NTIZESTWPVYFNL-UHFFFAOYAQ
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| Properties |
| Molecular formula |
C6H12O |
| Molar mass |
100.16 g/mol |
| Appearance |
colorless liquid |
| 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) |
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Refractive index (nD)
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1.3958 |
| Viscosity |
0.58 cP at 20.0 °C |
| Structure |
| Dipole moment |
2.8 D |
| Hazards |
| EU classification |
Flammable (F)
Harmful (Xn) |
| R-phrases |
R11, R20, R36/37, R66 |
| S-phrases |
(S2), S9, S16, S29 |
| NFPA 704 |
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| Flash point |
14 °C (57 °F; 287 K) |
| Related compounds |
| Related ketones |
Methyl isopropyl ketone
2-Pentanone
Diisobutyl ketone |
| Related compounds |
2-Methylpentan-4-ol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| 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.[1]
Several million kilograms are produced annually.[2]
Uses
MIBK is used as a solvent for nitrocellulose, lacquers, and certain polymers and resins.[2]
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.[3]
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.[4]
References
- ^ [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
English Journal
- Purification of Biomass-Derived 5-Hydroxymethylfurfural and Its Catalytic Conversion to 2,5-Furandicarboxylic Acid.
- Yi G1, Teong SP, Li X, Zhang Y.
- ChemSusChem.ChemSusChem.2014 May 28. doi: 10.1002/cssc.201402105. [Epub ahead of print]
- A simple and effective water extraction method is presented for the purification 5-hydroxylmethylfurfural (HMF) obtained from a biomass dehydration system. Up to 99 % of the HMF can be recovered and the HMF in aqueous solution is directly converted to 2,5-furandicarboxylic acid (FDCA) as the sole
- PMID 24889713
- Recent advances in thermal desorption-gas chromatography-mass spectrometery method to eliminate the matrix effect between air and water samples: application to the accurate determination of Henry's law constant.
- Kim YH1, Kim KH2.
- Journal of chromatography. A.J Chromatogr A.2014 May 16;1342:78-85. doi: 10.1016/j.chroma.2014.03.040. Epub 2014 Mar 21.
- Accurate values for the Henry's law constants are essential to describe the environmental dynamics of a solute, but substantial errors are recognized in many reported data due to practical difficulties in measuring solubility and/or vapor pressure. Despite such awareness, validation of experimental
- PMID 24704185
- Synthesis of 5-hydroxymethylfurural from carbohydrates using large-pore mesoporous tin phosphate.
- Dutta A1, Gupta D, Patra AK, Saha B, Bhaumik A.
- ChemSusChem.ChemSusChem.2014 Mar;7(3):925-33. doi: 10.1002/cssc.201300766. Epub 2014 Jan 28.
- A large-pore mesoporous tin phosphate (LPSnP-1) material has been synthesized hydrothermally by using Pluronic P123 as the structure-directing agent. The material is composed of aggregated nanoparticles of 10-15 nm in diameter and has a BET surface area of 216 m(2) g(-1) with an average pore
- PMID 24474710
Japanese Journal
- ケイ酸塩中のモリブデン,スズ,タンタルおよびタングステンの中性子放射化分析
Related Links
- 3 Isopropylacetoneイラストとクリップアート. 低価格なロイヤリティーフリーストックフォト。毎週何千もの画像が追加される中、¥ 200点$1で購入でき、定額プランは¥ 8000です。ストックフォトの画像検索エンジンはロイヤリティー写真 ...
- (redirected from Isopropylacetone) Also found in: Dictionary/thesaurus, Encyclopedia, Wikipedia. meth·yl i·so·bu·tyl ke·tone at high concentrations a narcotic, in lower concentrations it may irritate the eyes and mucous Want to . ...
Related Pictures
★リンクテーブル★
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- 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