2-Ethylhexanal

2-Ethylhexanal
Names
	IUPAC name 2-Ethylhexanal
Identifiers
CAS Number	123-05-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:87809;
ChEMBL	ChEMBL1558074;
ChemSpider	28981;
ECHA InfoCard	100.004.179
EC Number	204-596-5;
PubChem CID	31241;
UNII	SEN8S34O6U;
UN number	1191
CompTox Dashboard (EPA)	DTXSID9025291 ;
	InChI InChI=1S/C8H16O/c1-3-5-6-8(4-2)7-9/h7-8H,3-6H2,1-2H3 Key: LGYNIFWIKSEESD-UHFFFAOYSA-N;
	SMILES CCCCC(CC)C=O;
Properties
Chemical formula	C8H16O
Molar mass	128.215 g·mol−1
Appearance	colorless liquid
Density	0.820 g/cm3
Melting point	<-60
Boiling point	163 °C (325 °F; 436 K)
Refractive index (nD)	1.416
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H317, H319, H361
Precautionary statements	P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P272, P280, P302+P352, P303+P361+P353, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)	2 2 1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Ethylhexanal is the organic compound with the formula CH₃CH₂CH₂CH₂CH(C₂H₅)CHO. A colorless liquid, it is produced on a large scale industrially as a precursor to 2-ethylhexanoic acid and 2-ethylhexanol, both used as precursors to plasticizers. It was studied in the detergent industry since the 1930s.^[2]

2-Ethylhexanal is synthesized by aldol condensation of two equivalents of butyraldehyde followed by hydrogenation of the intermediate 2-ethylhexenal.^[3] The compound is chiral, but is mainly used as a racemic mixture.

The n-butyraldehyde is made by hydroformylation of propylene, either in a self-contained plant or as the first step in a fully integrated facility. Most facilities make n-butanol and isobutanol in addition to 2-ethylhexanol. Alcohols prepared in this way are sometimes referred to as oxo alcohols. The overall process is very similar to that of the Guerbet reaction, by which it may also be produced.^[4]

References

^ "2-Ethylhexanal". pubchem.ncbi.nlm.nih.gov.
^ Gangloff, W. C. (1938). "Changing trends in detergents". Oil and Soap. 15 (1): 14–17. doi:10.1007/BF02549560. ISSN 2331-3420.
^ Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3-527-30673-2.
^ Miller, Robert; Bennett, George (January 1961). "Producing 2-Ethylhexanol by the Guerbet Reaction". Industrial & Engineering Chemistry. 53 (1): 33–36. doi:10.1021/ie50613a027.

[1] "2-Ethylhexanal". pubchem.ncbi.nlm.nih.gov.

[2] Gangloff, W. C. (1938). "Changing trends in detergents". Oil and Soap. 15 (1): 14–17. doi:10.1007/BF02549560. ISSN 2331-3420.

[3] Kohlpaintner, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen (2008). "Aldehydes, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_321.pub2. ISBN 978-3-527-30673-2.

[4] Miller, Robert; Bennett, George (January 1961). "Producing 2-Ethylhexanol by the Guerbet Reaction". Industrial & Engineering Chemistry. 53 (1): 33–36. doi:10.1021/ie50613a027.

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