Crotonaldehyde

Crotonaldehyde[1]
Skeletal formula of crotonaldehyde
Ball-and-stick model of (Z)-crotonaldehyde
Names
IUPAC name
(2E)-but-2-enal
Other names
Crotonaldehyde
Crotonic aldehyde
β-Methacrolein
β-Methyl acrolein
2-butenal
Propylene aldehyde
Identifiers
  • 4170-30-3 (E/Z) checkY
  • 123-73-9 (E) checkY
  • 15798-64-8 (Z) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:41607 checkY
ChEMBL
  • ChEMBL1086445 checkY
ChemSpider
  • 394562 checkY
DrugBank
  • DB04381 checkY
ECHA InfoCard100.021.846
EC Number
  • 204-647-1
  • 6288
KEGG
  • C19377 ☒N
  • 447466
RTECS number
  • GP9499000
UNII
  • 9G72074TUW (E/Z) checkY
  • 6PUW625907 (E) checkY
  • RB9WCA91QT (Z) checkY
UN number1143
  • DTXSID8024864
  • InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+ checkY
    Key: MLUCVPSAIODCQM-NSCUHMNNSA-N checkY
  • InChI=1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
    Key: MLUCVPSAIODCQM-NSCUHMNNBQ
  • O=C/C=C/C
Properties ((E) isomer)
C4H6O
Molar mass70.091 g·mol−1
Appearancecolourless liquid
Odorpungent, suffocating odor
Density0.846 g/cm3
Melting point−76.5 °C (−105.7 °F; 196.7 K)
Boiling point104.0 °C (219.2 °F; 377.1 K)
18% (20 °C)[2]
Solubilityvery soluble in ethanol, ethyl ether, acetone
soluble in chloroform
miscible in benzene
Vapor pressure19 mmHg (20 °C)[2]
1.4362
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H225, H301, H310, H311, H315, H318, H330, H335, H341, H373, H400
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P320, P321, P322, P330, P332+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
4
3
2
Flash point13 °C (55 °F; 286 K)
207 °C (405 °F; 480 K)
Explosive limits2.1–15.5%
Lethal dose or concentration (LD, LC):
600 ppm (rat, 30 min)
1375 ppm (rat, 30 min)
519 ppm (mouse, 2 hr)
1500 ppm (rat, 30 min)[3]
400 ppm (rat, 1 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 2 ppm (6 mg/m3)[2]
REL (Recommended)
TWA 2 ppm (6 mg/m3)[2]
IDLH (Immediate danger)
50 ppm[2]
Related compounds
Related alkenals
Acrolein

cis-3-hexenal
(E,E)-2,4-Decadienal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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. 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 reactivity

Crotonaldehyde is produced by the aldol condensation of acetaldehyde:

2 CH3CHO → CH3CH=CHCHO + H2O

Crotonaldehyde is a multifunctional molecule that exhibits diverse reactivity. It is a prochiral dienophile.[5] It is a Michael acceptor. Addition of methylmagnesium chloride produces 3-penten-2-ol.[6]

Uses

Crotonylidene diurea is a specialty fertilizer.[7]

It is a precursor to many fine chemicals. A prominent industrial example is the crossed aldol condensation with diethyl ketone to give trimethylcyclohexenone, this can be easily converted to trimethylhydroquinone, which is a precursor to the vitamin E.[8] Other derivatives include crotonic acid, 3-methoxybutanol and the food preservative Sorbic acid. Condensation with two equivalents of urea gives a pyrimidine derivative that is employed as a controlled-release fertilizer.[4]

Safety

Crotonaldehyde is a potent irritant even at the ppm levels. It is not very toxic, with an LD50 of 174 mg/kg (rats, oral).[4]

See also

References

  1. ^ Merck Index, 11th Edition, 2599
  2. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0157". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ a b "Crotonaldehyde". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
  4. ^ a b c R. P. Schulz; J. Blumenstein; C. Kohlpaintner (2005). "Crotonaldehyde and Crotonic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_083. ISBN 978-3-527-30673-2.
  5. ^ Longley Jr., R. I..; Emerson, W. S.; Blardinelli, A. J. (1954). "3,4-Dihydro-2-methoxy-4-methyl-2H-pyran". Org. Synth. 34: 29. doi:10.15227/orgsyn.034.0029.
  6. ^ Coburn, E. R. (1947). "3-Penten-2-ol". Org. Synth. 27: 65. doi:10.15227/orgsyn.027.0065.
  7. ^ Dittmar, Heinrich; Drach, Manfred; Vosskamp, Ralf; Trenkel, Martin E.; Gutser, Reinhold; Steffens, Günter (2009). "Fertilizers, 2. Types". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.n10_n01. ISBN 978-3-527-30673-2.
  8. ^ Müller, Marc-André; Schäfer, Christian; Litta, Gilberto; Klünter, Anna-Maria; Traber, Maret G.; Wyss, Adrian; Ralla, Theo; Eggersdorfer, Manfred; Bonrath, Werner (6 December 2022). "100 Years of Vitamin E: From Discovery to Commercialization" (PDF). European Journal of Organic Chemistry. 2022 (45). doi:10.1002/ejoc.202201190.
  • Hazardous Substance Fact Sheet
  • CDC - NIOSH Pocket Guide to Chemical Hazards
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