Butyraldehyde[1]
Structural formula of butyraldehyde
Flat structure
Ball-and-stick model
Names
Preferred IUPAC name
Butanal
Other names
Butyraldehyde
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.225
EC Number
  • 204-646-6
KEGG
RTECS number
  • ES2275000
UNII
UN number 1129
  • InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 checkY
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYAZ
  • O=CCCC
Properties
C4H8O
Molar mass 72.107 g·mol−1
Appearance Colorless liquid
Odor Pungent, aldehyde odor
Density 0.8016 g/mL
Melting point −96.86 °C (−142.35 °F; 176.29 K)
Boiling point 74.8 °C (166.6 °F; 347.9 K)
Critical point (T, P) 537 K (264 °C),
4.32 MPa (42.6 atm)
7.6 g/100 mL (20 °C)
Solubility Miscible with organic solvents
log P 0.88
−46.08·10−6 cm3/mol
1.3766
Viscosity 0.45 cP (20 °C)
2.72 D
Thermochemistry[2]
163.7 J·mol−1·K−1 (liquid)
103.4 J·mol−1·K−1 (gas)
246.6 J·mol−1·K−1 (liquid)
343.7 J·mol−1·K−1 (gas)
−239.2 kJ·mol−1 (liquid)
−204.8 kJ·mol−1 (gas)
2470.34 kJ·mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark[3]
Danger
H225, H319[3]
P210, P280, P302+P352, P304+P340, P305+P351+P338[3]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
3
0
Flash point −7 °C (19 °F; 266 K)
230 °C (446 °F; 503 K)
Explosive limits 1.9–12.5%
Lethal dose or concentration (LD, LC):
2490 mg/kg (rat, oral)
Safety data sheet (SDS) Sigma-Aldrich
Related compounds
Related aldehyde
 Propionaldehyde
Pentanal
Related compounds
 Butan-1-ol
Butyric acid, isobutyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

Production

Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:

CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO

Traditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand tppts. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde.[4]

Reactions

Butyraldehyde undergoes reactions typical of alkyl aldehydes, and these define many of the uses of this compound. Important reactions include hydrogenation to the alcohol, oxidation to the acid, and base-catalyzed condensation.

Uses

Aldol condensation in the presence of a base forms 2-ethyl-2-hexenal, which is then hydrogenated to form 2-ethylhexanol, a precursor to the plasticizer bis(2-ethylhexyl) phthalate.[4]

Butyraldehyde is a precursor in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins.[5]

A major use of butyraldehyde is in the production of bis(2-ethylhexyl) phthalate, a major plasticizer.

References

  1. ↑ Merck Index, 11th Edition, 1591.
  2. ↑ CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
  3. 1 2 3 Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  4. 1 2 Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2. ISBN 978-3527306732.
  5. ↑ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN 978-3527306732.
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