Pentanal

Pentanal[1][2]
Names
	IUPAC name Pentanal
	Other names Pentanaldehyde; Valeraldehyde; Valeric aldehyde
Identifiers
CAS Number	110-62-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:84069 ;
ChemSpider	7772 ;
DrugBank	DB01919 ;
ECHA InfoCard	100.003.442
PubChem CID	8063;
UNII	B975S3014W ;
CompTox Dashboard (EPA)	DTXSID7021653 ;
	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	86.134 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).
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	Infobox references

Pentanal (also called valeraldehyde) is the organic compound is an alkyl aldehyde, molecular formula C₅H₁₀O. It is used in flavorings, resin chemistry, and rubber accelerators.[1] Its smell 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 is used in diverse 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).

Valeraldehyde is oxidized to give valeric acid.[6]

References

Merck Index, 11th Edition, 9813.
n-Valeraldehyde at chemicalland21.com
NIOSH Pocket Guide to Chemical Hazards. "#0652". National Institute for Occupational Safety and Health (NIOSH).
http://www.thegoodscentscompany.com/data/rw1009331.html
Patent WO 2009/146985 der Evonik Oxeno GmbH.
Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.

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[Merck-1] Merck Index, 11th Edition, 9813.

[2] -Valeraldehyde at chemicalland21.com

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0652". National Institute for Occupational Safety and Health (NIOSH).

[4] ttp://www.thegoodscentscompany.com/data/rw1009331.html

[5] Patent WO 2009/146985 der Evonik Oxeno GmbH.

[Ullmann-6] Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.