Pentanal

Not to be confused with Pantanal.

Pentanal ^{[1] [2]}

Names
Preferred IUPAC name Pentanal
Other names Pentanaldehyde Valeraldehyde Valeric aldehyde
Identifiers
CAS Number	110-62-3  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:84069  N
ChemSpider	7772  N
DrugBank	DB01919  Y
ECHA InfoCard	100.003.442
PubChem CID	8063
UNII	B975S3014W  Y
UN number	2058
CompTox Dashboard (EPA)	DTXSID7021653
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	14 g/L (20 °C)
Vapor pressure	0.35 kPa (20 °C) [3]
Viscosity	0.6 mPa·s (20 °C)
Hazards
GHS labelling:
Pictograms
NFPA 704 (fire diamond)	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):
LD50 (median dose)	3200 mg/kg (oral, rat) 4860 mg/kg (dermal, rabbit)
LC50 (median concentration)	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). N  verify  (what is  YN ?) Infobox references

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. 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   978-3-527-30673-2.