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

PubChem CID

* 8063

UNII |

* B975S3014W Y

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).

N verify (what is YN ?)
Infobox references

Pentanal (also called valeraldehyde) is the organic compound with molecular formula C

9CHO. 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. ↑ 3.0 3.1 3.2 3.3 3.4 NIOSH Pocket Guide to Chemical Hazards. "#0652". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0652.html.
4. ↑ "Valeraldehyde, 110-62-3". http://www.thegoodscentscompany.com/data/rw1009331.html.
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). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.

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*[CID]: Compound ID