Pentanal

Pentanal, also called pentanaldehyde or valeraldehyde, is an alkyl aldehyde, molecular formula C5H10O. It is used in flavorings, resin chemistry, and rubber accelerators.[1] Its smell is described as fermented, bready, fruity, nutty, berry.[4]

Pentanal[1][2]
Names
IUPAC name
Pentanal
Other names
Pentanaldehyde
Valeraldehyde
Valeric aldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.442
PubChem CID
UNII
Properties
Chemical formula
 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)
Solubility in water
 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).
N verify (what is YN ?)
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 is used in different flavors (e. g. fruit flavors) and as a vulcanization accelerator.

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).

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. http://www.thegoodscentscompany.com/data/rw1009331.html
  5. Patent WO 2009/146985 der Evonik Oxeno GmbH.
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