Butyraldehyde

Last updated
Butyraldehyde [1]
Structural formula of butyraldehyde Butanal-skeletal.png
Structural formula of butyraldehyde
Flat structure Butyraldehyde flat structure.png
Flat structure
Ball-and-stick model Butyraldehyde-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Butanal
Other names
Butyraldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.225 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-646-6
KEGG
PubChem CID
RTECS number
  • ES2275000
UNII
UN number 1129
  • InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Yes check.svgY
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceColorless 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)
Std molar
entropy (S⦵298)
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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg [3]
Danger
H225, H319 [3]
P210, P280, P302+P352, P304+P340, P305+P351+P338 [3]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).
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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.

Contents

Production

Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:

CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO

Traditionally, hydroformylation was catalyzed by cobalt carbonyl but rhodium complexes are more common. 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 (less dense) immiscible phase. About 6 billion kilograms are produced annually in this manner. 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 and uses

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. In the presence of a base, two equivalents of butyraldehyde undergoe aldol condensation to give 2-ethylhexenal. This unsaturated aldehyde is then partially hydrogenated to form 2-ethylhexanal, a precursor to plasticizers such as bis(2-ethylhexyl) phthalate. [4]

Butyraldehyde is a component 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. Bis(2-ethylhexyl) phthalate.svg
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 Recordof 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   978-3-527-30673-2.
  5. ↑ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN   978-3-527-30673-2.
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