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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 Edit this at Wikidata
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 diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine 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 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
checkY verify (what is checkY☒N ?)

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[edit]

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[edit]

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[edit]

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[edit]

  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. ^ a b c Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  4. ^ a b 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.

External links[edit]

source: https://en.wikipedia.org/wiki/Butanal

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