Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is the 3-carbon aldehyde. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.
In this way, several hundred thousand tons are produced annually.[2]
Laboratory preparationedit
Propionaldehyde may also be prepared by oxidizing 1-propanol with a mixture of sulfuric acid and potassium dichromate. The reflux condenser contains water heated at 60 °C, which condenses unreacted propanol, but allows propionaldehyde to pass. The propionaldehyde vapor is immediately condensed into a suitable receiver. In this arrangement, any propionaldehyde formed is immediately removed from the reactor, thus it does not get over-oxidized to propionic acid.[3]
Propionaldehyde exhibits the reactions characteristic of alkyl aldehydes, e.g. hydrogenation, aldol condensations, oxidations, etc. It is the simplest aldehyde with a prochiral methylene such that α-functionalized derivatives (CH3CH(X)CHO) are chiral.
Propionaldehyde is a common reagent, being a building block to many compounds.[4] Many of these uses exploit its participation in condensation reactions.[5][verification needed] With tert-butylamine it gives CH3CH2CH=N-t-Bu, a three-carbon building block used in organic synthesis.[6]
^Hurd, Charles D.; Meinert, R. N. (1932). "Propionaldehyde". Organic Syntheses. 12: 64. doi:10.15227/orgsyn.012.0064.
^Wehrli, Pius A.; Chu, Vera (1978). "Y-Ketoesters from Aldehydes Via Diethyl Acylsuccinates: Ethyl 4-Oxohexanoate". Organic Syntheses. 58: 79. doi:10.15227/orgsyn.058.0079.
^Sessler, Jonathan L.; Mozaffari, Azadeh; Johnson, Martin R. (1992). "3,4-Diethylpyrrole and 2,3,7,8,12,13,17,18-Octaethylporphyrin". Org. Synth. 70: 68. doi:10.15227/orgsyn.070.0068.
^Peralta, M. M. "Propionaldehyde t-Butylimine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X.
^Scientists Discover Two New Interstellar Molecules: Point to Probable Pathways for Chemical Evolution in Space, National Radio Astronomy Observatory, June 21, 2004
^Two newly found space molecules. By: Goho, Alexandra, Science News, 00368423, 7/24/2004, Vol. 166, Issue 4
^Chemical Precursors to Life Found in Space Scientists say that a universal prebiotic chemistry may be at work
^Jordans, Frank (30 July 2015). . The Washington Post. Associated Press. Archived from the original on 23 December 2018. Retrieved 30 July 2015.
^"Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
^Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G.; Kofman, W.; Mottola, S.; Seidenstiker, K.J.; Spohn, T.; Wright, I. (31 July 2015). "Philae's First Days on the Comet - Introduction to Special Issue" (PDF). Science. 349 (6247): 493. Bibcode:2015Sci...349..493B. doi:10.1126/science.aac5116. PMID 26228139.
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April 10, 2024
propionaldehyde, confused, with, propanol, propanal, organic, compound, with, formula, ch3ch2cho, carbon, aldehyde, colourless, flammable, liquid, with, pungent, fruity, odour, produced, large, scale, industrially, skeletal, formula, propionaldehyde, propanal,. Not to be confused with propanol Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO It is the 3 carbon aldehyde It is a colourless flammable liquid with a pungent and fruity odour It is produced on a large scale industrially Propionaldehyde Skeletal formula of propionaldehyde propanal Flat structureNamesIUPAC name PropionaldehydePreferred IUPAC name PropanalOther names MethylacetaldehydePropionic aldehydePropaldehydePropan 1 oneIdentifiersCAS Number 123 38 6 Y3D model JSmol Interactive image3DMet B01258ChEBI CHEBI 17153 YChEMBL ChEMBL275626 YChemSpider 512 YECHA InfoCard 100 004 204EC Number 204 623 0KEGG C00479PubChem CID 527RTECS number UE0350000UNII AMJ2B4M67V YUN number 1275CompTox Dashboard EPA DTXSID2021658InChI InChI 1S C3H6O c1 2 3 4 h3H 2H2 1H3 YKey NBBJYMSMWIIQGU UHFFFAOYSA N YSMILES CCC OPropertiesChemical formula C 3H 6OMolar mass 58 080 g mol 1Appearance Colourless liquidOdor Pungent and fruityDensity 0 81 g cm 3Melting point 81 C 114 F 192 K Boiling point 46 to 50 C 115 to 122 F 319 to 323 K Solubility in water 20 g 100 mLMagnetic susceptibility x 34 32 10 6 cm3 molViscosity 0 6 cP at 20 CStructureMolecular shape C1 O sp2C2 C3 sp3Dipole moment 2 52 DHazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H302 H315 H318 H332 H335 1 Precautionary statements P210 P261 P280 P304 P340 P312 P305 P351 P338 P310 P403 P235 1 NFPA 704 fire diamond 232Flash point 26 C 15 F 247 K Autoignitiontemperature 175 C 347 F 448 K Related compoundsRelated aldehydes AcetaldehydeButyraldehydeExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Production 1 1 Laboratory preparation 2 Reactions 3 Uses 3 1 Laboratory uses 4 Extraterrestrial occurrence 5 Safety 6 ReferencesProduction editPropionaldehyde is mainly produced industrially by hydroformylation of ethylene CO H2 C2H4 CH3CH2CHOIn this way several hundred thousand tons are produced annually 2 Laboratory preparation edit Propionaldehyde may also be prepared by oxidizing 1 propanol with a mixture of sulfuric acid and potassium dichromate The reflux condenser contains water heated at 60 C which condenses unreacted propanol but allows propionaldehyde to pass The propionaldehyde vapor is immediately condensed into a suitable receiver In this arrangement any propionaldehyde formed is immediately removed from the reactor thus it does not get over oxidized to propionic acid 3 Reactions editMain article aldehyde Propionaldehyde exhibits the reactions characteristic of alkyl aldehydes e g hydrogenation aldol condensations oxidations etc It is the simplest aldehyde with a prochiral methylene such that a functionalized derivatives CH3CH X CHO are chiral Uses editIt is predominantly used as a precursor to trimethylolethane CH3C CH2OH 3 through a condensation reaction with formaldehyde This triol is an important intermediate in the production of alkyd resins It is used in the synthesis of several common aroma compounds cyclamen aldehyde helional lilial Other applications include reduction to propanol and oxidation to propionic acid 2 Laboratory uses edit Propionaldehyde is a common reagent being a building block to many compounds 4 Many of these uses exploit its participation in condensation reactions 5 verification needed With tert butylamine it gives CH3CH2CH N t Bu a three carbon building block used in organic synthesis 6 Extraterrestrial occurrence editPropionaldehyde along with acrolein has been detected in the molecular cloud Sagittarius B2 near the center of the Milky Way Galaxy about 26 000 light years from Earth 7 8 9 Measurements by the COSAC and Ptolemy instruments on comet 67 P s surface revealed sixteen organic compounds four of which were seen for the first time on a comet including acetamide acetone methyl isocyanate and propionaldehyde 10 11 12 Safety editWith an LD50 of 1690 mg kg oral 2 propionaldehyde exhibits low acute toxicity but is a lung and eye irritant and is a combustible liquid References edit a b Record of Propanal in the GESTIS Substance Database of the Institute for Occupational Safety and Health accessed on 22 March 2020 a b c Hensel A 2018 Propanal Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a22 157 pub3 ISBN 978 3527306732 Hurd Charles D Meinert R N 1932 Propionaldehyde Organic Syntheses 12 64 doi 10 15227 orgsyn 012 0064 Wehrli Pius A Chu Vera 1978 Y Ketoesters from Aldehydes Via Diethyl Acylsuccinates Ethyl 4 Oxohexanoate Organic Syntheses 58 79 doi 10 15227 orgsyn 058 0079 Sessler Jonathan L Mozaffari Azadeh Johnson Martin R 1992 3 4 Diethylpyrrole and 2 3 7 8 12 13 17 18 Octaethylporphyrin Org Synth 70 68 doi 10 15227 orgsyn 070 0068 Peralta M M Propionaldehyde t Butylimine in Encyclopedia of Reagents for Organic Synthesis Ed L Paquette 2004 J Wiley amp Sons New York doi 10 1002 047084289X Scientists Discover Two New Interstellar Molecules Point to Probable Pathways for Chemical Evolution in Space National Radio Astronomy Observatory June 21 2004 Two newly found space molecules By Goho Alexandra Science News 00368423 7 24 2004 Vol 166 Issue 4 Chemical Precursors to Life Found in Space Scientists say that a universal prebiotic chemistry may be at work Jordans Frank 30 July 2015 Philae probe finds evidence that comets can be cosmic labs The Washington Post Associated Press Archived from the original on 23 December 2018 Retrieved 30 July 2015 Science on the Surface of a Comet European Space Agency 30 July 2015 Retrieved 30 July 2015 Bibring J P Taylor M G G T Alexander C Auster U Biele J Finzi A Ercoli Goesmann F Klingehoefer G Kofman W Mottola S Seidenstiker K J Spohn T Wright I 31 July 2015 Philae s First Days on the Comet Introduction to Special Issue PDF Science 349 6247 493 Bibcode 2015Sci 349 493B doi 10 1126 science aac5116 PMID 26228139 nbsp Wikimedia Commons has media related to Propionaldehyde Retrieved from https 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