Pentanal

Pentanal^[1][2]

Names
IUPAC name Pentanal
Other names Pentanaldehyde Valeraldehyde Valeric aldehyde
Identifiers
CAS Number	110-62-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:84069
ChemSpider	7772
DrugBank	DB01919
ECHA InfoCard	100.003.442
PubChem	8063
UNII	B975S3014W
InChI InChI=1S/C5H10O/c1-2-3-4-5-6/h5H,2-4H2,1H3 Key: HGBOYTHUEUWSSQ-UHFFFAOYSA-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	86.13 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]
US health exposure limits (NIOSH):
PEL (Permissible)	none[3]
REL (Recommended)	TWA 50 ppm (175 mg/m^3)[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 pentanaldehyde or valeraldehyde, is an alkyl aldehyde, molecular formula C₅H₁₀O. It is used in flavorings, resin chemistry, and rubber accelerators.^[1]

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%.^[4]

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. Patent WO 2009/146985 der Evonik Oxeno GmbH.