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P a g e s f o r l o g g e d o u t e d i t o r s l e a r n m o r e ● C o n t r i b u t i o n s ● T a l k
( T o p )
1 P r o d u c t i o n
2 U s e s
T o g g l e U s e s s u b s e c t i o n
2 . 1 P r e c u r s o r t o 6 P P D
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3 R e f e r e n c e s
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1 5 l a n g u a g e s
● ت ۆ ر ک ج ه ● Č e š t i n a ● D e u t s c h ● E s p a ñ o l ● E s p e r a n t o ● ف ا ر س ی ● F r a n ç a i s ● I t a l i a n o ● N e d e r l a n d s ● 日 本 語 ● С р п с к и / s r p s k i ● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и ● S u o m i ● S v e n s k a ● 中 文
E d i t l i n k s
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T o o l s
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P r i n t / e x p o r t
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I n o t h e r p r o j e c t s
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A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Methyl isobutyl ketone
Names
Preferred IUPAC name
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
CAS Number
3D model (JSmol )
Abbreviations
MIBK
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.228
EC Number
KEGG
PubChem CID
RTECS number
UNII
UN number
1245
CompTox Dashboard (EPA )
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
Properties
Chemical formula
C 6 H 12 O
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]
Magnetic susceptibility (χ)
-70.05·10−6 cm 3
Refractive index (n D
1.3958
Viscosity
0.58 cP
Structure
Dipole moment
2.8 D
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard statements
H225 , H319 , H332 , H335 , H351
Precautionary statements
P210 , P233 , P240 , P241 , P242 , P243 , P261 , P264 , P271 , P280 , P303+P361+P353 , P304+P312 , P304+P340 , P305+P351+P338 , P312 , P337+P313 , P370+P378 , P403+P233 , P403+P235 , P405 , P501
NFPA 704
Flash point
14 °C (57 °F; 287 K )
Autoignition
449 °C (840 °F; 722 K )
Explosive limits
1.2–8.0% (93 °C)[1]
NIOSH
PEL (Permissible)
TWA 100 ppm (410 mg/m3 [1]
REL (Recommended)
TWA 50 ppm (205 mg/m3 3 [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).
Infobox references
Chemical compound
Methyl isobutyl ketone (MIBK , 4-methylpentan-2-one ) is an organic compound with the condensed chemical formula (CH 3 2 2 O )CH3 ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.[2]
Production [ edit ]
At laboratory scale, MIBK can be produced via a three-step process using acetone as the starting material. Self-condensation , a type of aldol reaction , produces diacetone alcohol ,[3] dehydrates to give 4-methylpent-3-en-2-one (commonly, mesityl oxide ).[4] hydrogenated to give MIBK.[5]
Industrially, these three steps are combined. Acetone is treated with a strongly acidic, palladium catalyst -doped cation exchange resin under medium pressure of hydrogen.[6] [5]
MIBK tank car in Europe.
MIBK is used as a solvent for nitrocellulose , lacquers, and certain polymers and resins.[5]
Precursor to 6PPD [ edit ]
Another major use is as a precursor to N N' -phenyl-p 6PPD ), an antiozonant used in tires. 6PPD is prepared by reductive coupling of MIBK with 4-aminodiphenylamine .[7]
Solvent and niche applications [ edit ]
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 used in 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 American and British police forces.[8] [9]
References [ edit ]
^ United States Environmental Protection Agency (September 2016). "Methyl Isobutyl Ketone (Hexone)" . Retrieved 2015-12-13 .
^ Conant, J. B.; Tuttle, N. (1921). "Diacetone Alcohol". Organic Syntheses 1 doi :10.15227/orgsyn.001.0045
^ Conant, J. B.; Tuttle, N. (1921). "Mesityl Oxide". Organic Syntheses 1 doi :10.15227/orgsyn.001.0053
^ a b c Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann’s Encyclopedia of Industrial Chemistry , Wiley-VCH, Weinheim, 2005.
^ Uhde GmbH (2005). "Uhde Technology Profile: MIBK" (PDF) . Archived from the original (PDF) on 2013-12-03. Retrieved 18 October 2021 .
^ 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 .
^ Roger Eardley-Pryor (2017). "A Tear Gas Tale" . Science History Institute . Retrieved 2021-02-22 .
External links [ edit ]
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Methyl_isobutyl_ketone&oldid=1188609345 " C a t e g o r i e s : ● H a z a r d o u s a i r p o l l u t a n t s ● H e x a n o n e s ● K e t o n e s o l v e n t s ● C o m m o d i t y c h e m i c a l s ● I A R C G r o u p 2 B c a r c i n o g e n s H i d d e n c a t e g o r i e s : ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● A r t i c l e s w i t h c h a n g e d I n C h I i d e n t i f i e r ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A r t i c l e s w i t h G N D i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 6 D e c e m b e r 2 0 2 3 , a t 1 4 : 3 6 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
