Pentanal

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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.442
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PubChem CID
UNII
InChI
  • 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
SMILES
  • O=CCCCC
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).
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Infobox references

Pentanal (also called valeraldehyde) is the organic compound 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]

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 diverse 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).

Valeraldehyde is oxidized to give valeric acid.[6]

References

  1. 1 2 Merck Index, 11th Edition, 9813.
  2. ↑ n-Valeraldehyde at chemicalland21.com
  3. 1 2 3 4 5 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. ↑ 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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