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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/07/07 21:25:40」(JST)
[Wiki ja表示]
| メチルイソブチルケトン |
|
| 一般情報 |
| IUPAC名 |
4-methyl-2-pentanone |
| 別名 |
MIBK、4-メチル-2-ペンタノン、イソプロピルアセトン |
| 分子式 |
C6H12O |
| 分子量 |
100.16 g/mol |
| 形状 |
無色液体 |
| CAS登録番号 |
[108-10-1] |
| SMILES |
CC(C)CC(=O)C |
| 性質 |
| 密度と相 |
0.801 (20 ℃) g/cm3, |
| 水への溶解度 |
1.91 g/100 mL (20 ℃) |
| 融点 |
-84 °C |
| 沸点 |
116.2 °C |
| 屈折率 |
1.396 (20 ℃) |
メチルイソブチルケトン (methyl isobutyl ketone、MIBK) はケトンに分類される有機溶媒の一種。示性式は CH3C(=O)CH2CH(CH3)2、IUPAC命名法では 4-メチル-2-ペンタノン (4-methyl-2-pentanone) と表される。イソプロピルアセトン (isopropylacetone) とも呼ばれる。
特有の甘い匂いのする無色の液体で、沸点 116.2 ℃、融点 -84 ℃、引火点 17 ℃、発火点 457 ℃。アセトンなどの他のケトン類とは異なり、水には溶けにくい。
消防法による危険物（第4類引火性液体、第1石油類非水溶性液体）に指定されている。日本の悪臭防止法では特定悪臭物質に指定されている。
国際がん研究機関の発がん性評価では、グループ2Bの「発がん性の可能性がある物質」に分類されており、労働安全衛生法により第二類物質特別有機溶剤等に指定されている。。
ニトロセルロースなどの溶媒として、あるいは塗料、接着剤の成分として広く用いられる。また、ニオブとタンタルを鉱物から分離する際にも用いられる。
製法
メチルイソブチルケトンはアセトンより 3段階の過程で製造される（下図）。
まず 2分子のアセトンをアルドール反応させてジアセトンアルコールとすると、容易に脱水されてメシチルオキシドに変わる。メシチルオキシドを水素化すると、メチルイソブチルケトンが得られる。
外部リンク
- MSDS:メチルイソブチルケトン（厚労省）
- 国際化学物質安全性カード(ICSC) - 国立医薬品食品衛生研究所
|
この項目は、化学に関連した書きかけの項目です。この項目を加筆・訂正などしてくださる協力者を求めています（プロジェクト:化学／Portal:化学）。 |
[Wiki en表示]
Methyl isobutyl ketone
|
|
| Names |
| IUPAC name
4-Methyl-2-pentanone
|
| 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
|
| Identifiers |
|
CAS Registry Number
|
108-10-1 N |
| ChemSpider |
7621 N |
| EC number |
203-550-1 |
InChI
-
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
|
| Jmol-3D images |
Image |
| KEGG |
C19263 Y |
| PubChem |
7909 |
| RTECS number |
SA9275000 |
|
|
| 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] |
|
Refractive index (nD)
|
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 |
|
| 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): |
|
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).
|
| N verify (what is: Y/N?) |
| Infobox references |
|
|
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
English Journal
- Methyl isobutyl ketone exposure-related increases in specific measures of α2u-globulin (α2u) nephropathy in male rats along with in vitro evidence of reversible protein binding.
- Borghoff SJ1, Poet TS2, Green S3, Davis J4, Hughes B5, Mensing T6, Sarang SS7, Lynch AM8, Hard GC9.
- Toxicology.Toxicology.2015 Jul 3;333:1-13. doi: 10.1016/j.tox.2015.02.003. Epub 2015 Mar 19.
- Chronic exposure to methyl isobutyl ketone (MIBK) resulted in an increase in the incidence of renal tubule adenomas and occurrence of renal tubule carcinomas in male, but not female Fischer 344 rats. Since a number of chemicals have been shown to cause male rat renal tumors through the α2u nephropa
- PMID 25797582
- Lead determination at ng/mL level by flame atomic absorption spectrometry using a tantalum coated slotted quartz tube atom trap.
- Demirtaş İ1, Bakırdere S2, Ataman OY3.
- Talanta.Talanta.2015 Jun 1;138:218-24. doi: 10.1016/j.talanta.2015.02.044. Epub 2015 Mar 12.
- Flame atomic absorption spectrometry (FAAS) still keeps its importance despite the relatively low sensitivity; because it is a simple and economical technique for determination of metals. In recent years, atom traps have been developed to increase the sensitivity of FAAS. Although the detection limi
- PMID 25863394
- The direct conversion of sugars into 2,5-furandicarboxylic acid in a triphasic system.
- Yi G1, Teong SP, Zhang Y.
- ChemSusChem.ChemSusChem.2015 Apr 13;8(7):1151-5. doi: 10.1002/cssc.201500118. Epub 2015 Mar 12.
- A one-pot conversion of sugars into 2,5-furandicarboxylic acid (FDCA) is demonstrated in a triphasic system: tetraethylammonium bromide (TEAB) or water-methyl isobutyl ketone (MIBK)-water. In this reaction, sugars are first converted into 5-hydroxymethylfurfural (HMF) in TEAB or water (Phase I). T
- PMID 25766123
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
- Water / Methyl isobutyl ketone (MIBK) Biphasic System in Slug Flow under High Temperature and Pressure Conditions
- SHIMANOUCHI Toshinori,TANIFUJI Tatsuya,FUJIOKA Satoko,TERASAKA Koichi,KIMURA Yukitaka
- Solvent Extraction Research and Development, Japan 21(2), 201-209, 2014
- … In this study, the water / methyl isobuthyl ketone (MIBK) biphasic system was investigated under various temperatures (25 – 190 oC) at 10 MPa. … The partitioning behavior of substrates such as furfural derivatives, amino acids, and saccharides, depended on the temperature and the flow rate ratio of MIBK to the water phase. …
- NAID 130004669678
- Extraction of astatine isotopes for development of radiopharmaceuticals using a 211Rn–211At generator
- Maeda E.,Yokoyama Akihiko,Taniguchi T.,Washiyama K.,Nishinaka Ichiro
- Journal of Radioanalytical and Nuclear Chemistry 303(2), 1465-1468, 2014
- … The astatine isotopes have been found to be well extracted into DIPE and MIBK. …
- NAID 120005593937
Related Links
- 「MIBK」のサイト内検索分類 [製品分野] 溶剤・界面活性剤/ [用途分野] 工業用化学品/家電・OA機器/ お問い合わせ フェノール・ポリカーボネート事業部 TEL： 03-6748-7128(TEL),03-3286-1191(FAX ) 製品分野 表示部材・関連製品 ...
- 三協化学株式会社 SDS MIBK 4 を 利 用すること。 散水以外 の消火剤で消火の 効果 がない 大き な火災の場合には 散水 する。 危険でなけれ ば 火災区 域 から 容 器を 移動 する。 移動不可能 な場合、 容 器及び 周囲 に 散水 ...
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★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
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- 有機溶剤中毒予防規則
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