Isobutyric acid
Isobutyric acid
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| Names | |||
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Preferred IUPAC name 2-Methylpropanoic acid[3] | |||
| Other names Isobutyric acid (no longer recommended)[3] 2-Methylpropionic acid Isobutanoic acid | |||
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ECHA InfoCard | 100.001.087 | ||
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| Properties | |||
Chemical formula | C4H8O2 | ||
Molar mass | 88.11 g/mol | ||
Density | 0.9697 g/cm3 (0 °C) | ||
Melting point | −47 °C (−53 °F; 226 K) | ||
Boiling point | 155 °C (311 °F; 428 K) | ||
Acidity (pKa) | 4.86[4] | ||
Magnetic susceptibility (χ) | -56.06x10−6 cm3/mol | ||
| Hazards | |||
NFPA 704 |  2 1 0 | ||
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 ?) | |||
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Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2CHCO2H. It is a colorless liquid with a somewhat unpleasant odor. It is soluble in water and organic solvents. Isobutyric acid is an isomer of n-butyric acid. Deprotonation or esterification of isobutyric acid gives derivatives called isobutyrates. Isobutyric acid is found in the free state in carobs (Ceratonia siliqua), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil.[5]
Contents
1 Production
1.1 Niche methods
2 Reactions
3 References
Production[edit]
Isobutyric acid is prepared by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.[6]
It can also be prepared by the high pressure hydrocarboxylation (Koch reaction) from propylene:[6]
- CH3CH=CH2 + CO + H2O → (CH3)2CHCO2H
Niche methods[edit]
Many routes are known including the hydrolysis of isobutyronitrile with alkalis and the oxidation of isobutanol with potassium dichromate in the presence of sulfuric acid,[7] In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid.[5]
Isobutyric acid can also be manufactured commercially using engineered bacteria using a sugar feedstock.[8]
Reactions[edit]
When heated with a chromic acid solution it is oxidized to acetone. Alkaline potassium permanganate oxidizes it[5] to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.
Isobutyric acid is a retained trivial name under the IUPAC rules.[9]
References[edit]
^ Merck Index, 11th Edition, 5039
^ "Archived copy". Archived from the original on 2015-02-17. Retrieved 2015-03-13.CS1 maint: Archived copy as title (link) .mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ ab Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 748. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Bjerrum, J.; et al. (1958). Stability Constants. London: Chemical Society.CS1 maint: Explicit use of et al. (link)
^ abc
Chisholm, Hugh, ed. (1911). "Butyric Acid". Encyclopædia Britannica. 4 (11th ed.). Cambridge University Press. p. 892.
^ ab Riemenschneider, Wilhelm; Bolt, Hermann (2000). "Esters, Organic". Ullmann's Encyclopedia of Industrial Chemistry: 10. doi:10.1002/14356007.a09_565. Retrieved 17 December 2013.
^ I. Pierre and E. Puchot (1873). "New Studies on Valerianic Acid and its Preparation on a Large Scale". Ann. Chim. Phys. 28: 366.
^ "Biological pathways to produce methacrylate". Archived from the original on 2012-05-02. Retrieved 2011-10-07.
^ Panico R, Powell WH, Richer JC, eds. (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds. IUPAC/Blackwell Science. ISBN 0-632-03488-2.
Chisholm, Hugh, ed. (1911). "Butyric Acid". Encyclopædia Britannica. 4 (11th ed.). Cambridge University Press. p. 892.Categories:
- Alkanoic acids
- Glycine receptor antagonists
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