Pentanal

Pentanal (also called valeraldehyde) is the organic compound with molecular formula C4H9CHO. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry.[4]

Not to be confused with Pantanal.
Pentanal[1][2]
Structural formula of pentanal
Ball-and-stick model of the pentanal molecule
Names
Preferred IUPAC name
Pentanal
Other names
Pentanaldehyde
Valeraldehyde
Valeric aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.442
UNII
  • InChI=1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 ☒N
    Key: HGBOYTHUEUWSSQ-UHFFFAOYSA-N ☒N
  • InChI=1/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3
    Key: HGBOYTHUEUWSSQ-UHFFFAOYAJ
  • O=CCCCC
Properties
C5H10O
Molar mass 86.134 g·mol−1
Appearance Clear liquid
Odor Strong, acrid, pungent
Density 0.8095 at 20 °C
Melting point −60 °C (−76 °F; 213 K)
Boiling point 102 to 103 °C (216 to 217 °F; 375 to 376 K)
Very slightly soluble
Vapor pressure 26 mmHg (20 °C)[3]
Hazards
Flash point 12 °C; 54 °F; 285 K[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 TWA 50 ppm (175 mg/m3)[3]
IDLH (Immediate danger)
 N.D.[3]
Related compounds
Related aldehydes
 Butyraldehyde

Hexanal

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

Production

Pentanal is obtained by hydroformylation of butene. Also C4 mixtures can be used as starting material like the so-called raffinate II, which is produced by steam cracking and contains (Z)- and (E)-2-butene, 1-butene, butane and isobutane. The conversion to the product is accomplished with synthesis gas in the presence of a catalyst consisting of a rhodium-bisphosphite complex and a sterically hindered secondary amine with a selectivity toward pentanal of at least 90%.[5]

Use

Pentanal undergoes the reactions characteristic of any alkyl aldehyde, i.e., oxidations, condensations, and reductions. 2-Octanone, produced for use in the fragrance industry, is obtained by the condensation of acetone and pentanal, followed by hydrogenation of the alkene.[6]

2-Propyl-2-heptenal is obtained from pentanal by aldol condensation, which is hydrogenated to the saturated branched 2-propylheptanol. This alcohol serves as a starting material for the PVC plasticizer di-2-propylheptyl phthalate (DPHP).

Pentanal (valeraldehyde) is oxidized to give valeric acid.[7]

References
  1. Merck Index, 11th Edition, 9813.
  2. n-Valeraldehyde at chemicalland21.com
  3. NIOSH Pocket Guide to Chemical Hazards. "#0652". National Institute for Occupational Safety and Health (NIOSH).
  4. "Valeraldehyde, 110-62-3".
  5. Patent WO 2009/146985 der Evonik Oxeno GmbH.
  6. Siegel, Hardo; Eggersdorfer, Manfred (2000). "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a15_077. ISBN 9783527306732.
  7. Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.
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