Butyraldehyde

Butyraldehyde[1]
Names
	Preferred IUPAC name Butanal
	Other names Butyraldehyde
Identifiers
CAS Number	123-72-8 ;
3D model (JSmol)	Interactive image;
3DMet	B00287;
ChEBI	CHEBI:15743 ;
ChEMBL	ChEMBL1478334;
ChemSpider	256 ;
ECHA InfoCard	100.004.225
EC Number	204-646-6;
KEGG	C01412 ;
PubChem CID	261;
RTECS number	ES2275000;
UNII	H21352682A ;
UN number	1129
CompTox Dashboard (EPA)	DTXSID8021513 ;
	InChI InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N ; InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Key: ZTQSAGDEMFDKMZ-UHFFFAOYAZ;
	SMILES O=CCCC;
Properties
Chemical formula	C4H8O
Molar mass	72.107 g·mol−1
Appearance	Colorless liquid
Odor	Pungent, aldehyde odor
Density	0.8016 g/mL
Melting point	−96.86 °C (−142.35 °F; 176.29 K)
Boiling point	74.8 °C (166.6 °F; 347.9 K)
Critical point (T, P)	537 K (264 °C),; 4.32 MPa (42.6 atm)
Solubility in water	7.6 g/100 mL (20 °C)
Solubility	Miscible with organic solvents
log P	0.88
Magnetic susceptibility (χ)	−46.08·10−6 cm3/mol
Refractive index (nD)	1.3766
Viscosity	0.45 cP (20 °C)
Dipole moment	2.72 D
Thermochemistry[2]
Heat capacity (C)	163.7 J·mol−1·K−1 (liquid) ; 103.4 J·mol−1·K−1 (gas)
Std molar; entropy (S⦵298)	246.6 J·mol−1·K−1 (liquid) ; 343.7 J·mol−1·K−1 (gas)
Std enthalpy of; formation (ΔfH⦵298)	−239.2 kJ·mol−1 (liquid) ; −204.8 kJ·mol−1 (gas)
Std enthalpy of; combustion (ΔcH⦵298)	2470.34 kJ·mol−1
Hazards
	GHS labelling:
Pictograms	[3]
Signal word	Danger
Hazard statements	H225, H319[3]
Precautionary statements	P210, P280, P302+P352, P304+P340, P305+P351+P338[3]
NFPA 704 (fire diamond)	3 3 0
Flash point	−7 °C (19 °F; 266 K)
Autoignition; temperature	230 °C (446 °F; 503 K)
Explosive limits	1.9–12.5%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2490 mg/kg (rat, oral)
Safety data sheet (SDS)	Sigma-Aldrich
Related compounds
Related aldehyde	Propionaldehyde; Pentanal
Related compounds	Butan-1-ol; Butyric acid, isobutyraldehyde
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Butyraldehyde, also known as butanal, is an organic compound with the formula CH₃(CH₂)₂CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.

Production

Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:

CH₃CH=CH₂ + H₂ + CO → CH₃CH₂CH₂CHO

Traditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand tppts. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde.[4]

Reactions

Butyraldehyde undergoes reactions typical of alkyl aldehydes, and these define many of the uses of this compound. Important reactions include hydrogenation to the alcohol, oxidation to the acid, and base-catalyzed condensation.

Uses

Aldol condensation in the presence of a base forms 2-ethyl-2-hexenal, which is then hydrogenated to form 2-ethylhexanol, a precursor to the plasticizer bis(2-ethylhexyl) phthalate.[4]

Butyraldehyde is a precursor in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins.[5]

A major use of butyraldehyde is in the production of bis(2-ethylhexyl) phthalate, a major plasticizer.

References

Merck Index, 11th Edition, 1591.
CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2.
Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2.

External links

International Chemical Safety Card 0403

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[1] Merck Index, 11th Edition, 1591.

[CRC97-2] CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)

[GESTIS-3] Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.

[:0-4] Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2.

[5] Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha. "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2.