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
  • 110-62-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:84069 ☒N
ChemSpider
  • 7772 ☒N
DrugBank
  • DB01919 checkY
ECHA InfoCard 100.003.442 Edit this at Wikidata
PubChem CID
  • 8063
UNII
  • B975S3014W checkY
UN number 2058
CompTox Dashboard (EPA)
  • DTXSID7021653 Edit this at Wikidata
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
  • 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
 14 g/L (20 °C)
Vapor pressure 0.35 kPa (20 °C)[3]
Viscosity 0.6 mPa·s (20 °C)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 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 12 °C (54 °F; 285 K)[3]
Autoignition
temperature
 220 °C (428 °F; 493 K)
Lethal dose or concentration (LD, LC):
3200 mg/kg (oral, rat)
4860 mg/kg (dermal, rabbit)
14.3 ppm (rat, 4h)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[3]
REL (Recommended)
 TWA 50 ppm (175 mg/m3)[3]
IDLH (Immediate danger)
 N.D.[3]
Safety data sheet (SDS) Fisher Scientific
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
Chemical compound

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]

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. ^ a b c d e 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. ISBN 978-3527306732.