Propionaldehyde 1112165 211473016 2008-05-10T15:10:31Z Smokefoot 698909 copy edit, wikify {{Chembox new | Name = Propionaldehyde | ImageFile = Propanal-skeletal.png | ImageName = Skeletal structure of propanal | IUPACName = Propionaldehyde | SystematicName = Propanal | OtherNames = Methylacetaldehyde; propionic aldehyde; propaldehyde | Section1 = {{Chembox Identifiers | SMILES = CCC=O | CASNo = 123-38-6 | UNNumber = 1275 | RTECS = }} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>6</sub>O | MolarMass = 58.080 g mol<sup>−1</sup> | Appearance = Colorless liquid<br />Pungent, marty odor | Density = 0.81 g cm<sup>−3</sup> | Solubility = 20 g/100 mL | MeltingPt = −81 °C (192 K) | BoilingPt = 46-50 °C (321 K) | Viscosity = 0.6 [[Poise|cP]] at 20°C }} | Section3 = {{Chembox Structure | MolShape = C<sub>1</sub>, O: sp<sup>2</sup> C<sub>2</sub>, C<sub>3</sub>: sp<sup>3</sup> | Dipole = 2.52 [[Debye|D]] }} | Section7 = {{Chembox Hazards | ExternalMSDS = | EUClass = Highly flammable ('''F''')<br />Irritant ('''Xi''') | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 2 | RPhrases = {{R11}}, {{R36/37/38}} | SPhrases = {{S9}}, {{S16}}, {{S29}} | FlashPt = −26 °C | Autoignition = 175 °C }} | Section8 = {{Chembox Related | Function = [[aldehyde]]s | OtherFunctn = [[Formaldehyde]]<br />[[Acetaldehyde]]<br />[[Butyraldehyde]] }} }} {{Distinguish2|[[Propanol|propan'''o'''l]]}} '''Propionaldehyde''' or '''propanal''' is the [[organic compound]] with the formula CH<sub>3</sub>CH<sub>2</sub>CHO. It is a saturate 3-carbon [[aldehyde]] and is a [[structural isomerism|structural isomer]] of [[propanone|acetone]]. It is a colourless liquid with a slightly irritating, fruity odour. Propionaldehyde is mainly produced through the [[hydroformylation]], by combining [[syngas|synthesis gas]] ([[carbon monoxide]] and [[hydrogen]]) with [[ethylene]] using a metal [[catalyst]]: :CO + H<sub>2</sub> + C<sub>2</sub>H<sub>4</sub> → CH<sub>3</sub>CH<sub>2</sub>CHO ==Uses== It is principally used as a precursor to "trimethylolethane" (CH<sub>3</sub>C(CH<sub>2</sub>OH)<sub>3</sub>) through a [[condensation reaction]] with [[methanol]]; this triol is an important intermediate in the production of [[alkyd]] [[resin]]s. Condensation of propionaldehyde with [[tert-butylamine]] gives CH<sub>3</sub>CH<sub>2</sub>CH=N-''t''-Bu, a three-carbon building block used in [[organic synthesis]]. Deprotonation of this [[imine]] with [[LDA]] produces CH<sub>3</sub>CHLiCH=N-''t''-Bu, which in turn condenses with [[aldehydes]].<ref>Peralta, M. M. "Propionaldehyde t-Butylimine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref> ==References== <references/> [[Category:Aldehydes]] [[Category:Hazardous air pollutants]] [[cs:Propionaldehyd]] [[de:Propanal]] [[fr:Propanal]] [[la:Propanal]] [[ja:プロピオンアルデヒド]] [[pl:Propanal]] [[pt:Propanal]] [[fi:Propionialdehydi]] [[zh:丙醛]]