Butyraldehyde - Wikipedia

Chemical compound CH3(CH2)2CHO Butyraldehyde[1]

Names
Preferred IUPAC name Butanal
Other names Butyraldehyde
Identifiers
CAS Number	123-72-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15743 Y
ChEMBL	ChEMBL1478334
ChemSpider	256 Y
ECHA InfoCard	100.004.225
EC Number	204-646-6
KEGG	C01412 Y
PubChem CID	261
RTECS number	ES2275000
UNII	H21352682A Y
UN number	1129
CompTox Dashboard (EPA)	DTXSID8021513
InChI InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 YKey: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Y InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3Key: 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 molarentropy (S⦵298)	246.6 J·mol−1·K−1 (liquid) 343.7 J·mol−1·K−1 (gas)
Std enthalpy offormation (ΔfH⦵298)	−239.2 kJ·mol−1 (liquid) −204.8 kJ·mol−1 (gas)
Std enthalpy ofcombustion (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)
Autoignitiontemperature	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	PropionaldehydePentanal
Related compounds	Butan-1-olButyric acid, isobutyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

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

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Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:

CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO

Traditionally, hydroformylation was catalyzed by cobalt carbonyl but rhodium complexes are more common. 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 (less dense) immiscible phase. About 6 billion kilograms are produced annually in this manner. 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 and uses

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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. In the presence of a base, two equivalents of butyraldehyde undergoe aldol condensation to give 2-ethylhexenal. This unsaturated aldehyde is then partially hydrogenated to form 2-ethylhexanal, a precursor to plasticizers such as bis(2-ethylhexyl) phthalate.[4]

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

References

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1. ^ Merck Index, 11th Edition, 1591.
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)
3. ^ a b c Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
4. ^ a b Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2. ISBN 978-3-527-30673-2.
5. ^ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN 978-3-527-30673-2.

External links

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• International Chemical Safety Card 0403

Authority control databases
International	GND
National	Japan