Crotonaldehyde
Names | |
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IUPAC name
(2E)-but-2-enal
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Other names
Crotonaldehyde
Crotoinic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde | |
Identifiers | |
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3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.021.846 |
EC Number |
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KEGG | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C4H6O | |
Molar mass | 70.091 g·mol−1 |
Appearance | colourless liquid |
Odor | pungent, suffocating odor |
Density | 0.846 g/cm3 |
Melting point | −76.5 °C (−105.7 °F; 196.7 K) |
Boiling point | 104.0 °C (219.2 °F; 377.1 K) |
18% (20°C)[2] | |
Solubility | very soluble in ethanol, ethyl ether, acetone soluble in chloroform miscible in benzene |
Vapor pressure | 19 mmHg (20°C)[2] |
Refractive index (nD)
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1.4362 |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 13 °C (55 °F; 286 K) |
207 °C (405 °F; 480 K) | |
Explosive limits | 2.1-15.5% |
Lethal dose or concentration (LD, LC): | |
LC50 (median concentration)
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600 ppm (rat, 30 min) 1375 ppm (rat, 30 min) 519 ppm (mouse, 2 hr) 1500 ppm (rat, 30 min)[3] |
LCLo (lowest published)
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400 ppm (rat, 1 hr)[3] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 2 ppm (6 mg/m3)[2] |
REL (Recommended)
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TWA 2 ppm (6 mg/m3)[2] |
IDLH (Immediate danger)
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50 ppm[2] |
Related compounds | |
Related alkenals
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Acrolein |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.[4]
Production and uses
Crotonaldehyde is produced by the aldol condensation of acetaldehyde:
- 2 CH3CHO → CH3CH=CHCHO + H2O
Its main application is as a precursor to fine chemicals. Sorbic acid, a food preservative, and trimethylhydroquinone, a precursor to the vitamin E, are prepared from crotonaldehyde. Other derivatives include crotonic acid and 3-methoxybutanol.[4]
Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is an excellent prochiral dienophile.[5] It is a Michael acceptor. Addition of methylmagnesium chloride produces 3-penten-2-ol.[6]
The reaction of crotonaldehyde with ethanol then gives kethoxal (anhydrous).
Polyurethane catalyst N,N,N',N'-tetramethyl-1,4-butanediamine (also known as TMBDA) is obtained by hydrogenating N,N,N',N'-tetramethyl-1,4-butenediamine which is a reaction product of crotonaldehyde and dimethylamine.[7]
Safety
Crotonaldehyde is an irritant. It is listed as an "extremely hazardous substance" as defined by the U.S. Emergency Planning and Community Right-to-Know Act. It occurs widely in nature. It is used to make preservatives.
See also
References
- ^ Merck Index, 11th Edition, 2599
- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0157". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Crotonaldehyde". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Crotonaldehyde and Crotonic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a08_083. ISBN 978-3527306732.
{{cite encyclopedia}}
: Unknown parameter|authors=
ignored (help) - ^ Longley, Jr., R. I..; Emerson, W. S.; Blardinelli, A. J. (1963). "3,4-Dihydro-2-methoxy-4-methyl-2H-pyran". Organic Syntheses
{{cite journal}}
: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 4, p. 311. - ^ Coburn, E. R. (1955). "3-Penten-2-ol". Organic Syntheses; Collected Volumes, vol. 3, p. 696.
- ^ https://jadedman.wordpress.com/2011/01/08/catalysts/