Pentanal

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Pentanal[1][2]
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UN number 2058
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Template:Longitem Template:Chembox Elements/molecular formula
Molar mass Template:Chem molar mass
Appearance Clear liquid
Odor Strong, acrid, pungent
Density 0.8095 at 20 °C
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Vapor pressure 0.35 kPa (20 °C)[3]
Viscosity 0.6 mPa·s (20 °C)
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Template:Longitem Butyraldehyde

Hexanal

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Pentanal (also called valeraldehyde) is the organic compound with molecular formula Template:Chem2. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor 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 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
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  5. Patent WO 2009/146985 der Evonik Oxeno GmbH.
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