Propionaldehyde

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Propionaldehyde
Skeletal formula of propionaldehyde (propanal)
Flat structure
Ball-and-stick model
Propionaldehyde.jpg
Names
IUPAC name
Propanal
Systematic IUPAC name
Propanal
Other names
  • Methylacetaldehyde
  • Propionic aldehyde
  • Propaldehyde
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.204 Edit this at Wikidata
EC Number
  • 204-623-0
KEGG
RTECS number
  • UE0350000
UNII
UN number 1275
Properties
C3H6O
Molar mass 58.080 g·mol−1
Appearance Colourless liquid
Odor Pungent, fruity
Density 0.81 g cm−3
Melting point −81 °C (−114 °F; 192 K)
Boiling point 46 to 50 °C (115 to 122 °F; 319 to 323 K)
20 g/100 mL
-34.32·10−6 cm3/mol
Viscosity 0.6 cP at 20 °C
Structure
C1, O: sp2

C2, C3: sp3

2.52 D
Hazards
GHS pictograms GHS02: Flammable GHS05: Corrosive GHS07: Harmful
GHS Signal word Danger
H225, H302, H332, H315, H318, H335[1]
P210, P261, P280, P304+340+312, P305+351+338, P310, P403+235[1]
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
2
Flash point −26 °C (−15 °F; 247 K)
175 °C (347 °F; 448 K)
Related compounds
Related aldehydes
Acetaldehyde
Butyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 slightly fruity odour. It is produced on a large scale industrially.

Production[edit]

Propionaldehyde is mainly produced industrially by hydroformylation of ethylene:

CO + H2 + C2H4 → CH3CH2CHO

In 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]

Uses[edit]

Its 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] With tert-butylamine it gives CH3CH2CH=N-t-Bu, a three-carbon building block used in organic synthesis.[6]

Extraterrestrial occurrence[edit]

Propionaldehyde 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[edit]

With an LD50 of 1690 mg/kg (oral),[2] propionaldehyde exhibits low acute toxicity.

References[edit]

  1. ^ a b Record of Propanal in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 22 March 2020.
  2. ^ a b c Hensel, A. (2018). "Propanal". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_157.pub3.
  3. ^ Hurd, Charles D.; Meinert, R. N. (1932). "Propionaldehyde". Organic Syntheses. 12: 64. doi:10.15227/orgsyn.012.0064.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ Scientists Discover Two New Interstellar Molecules: Point to Probable Pathways for Chemical Evolution in Space, National Radio Astronomy Observatory, June 21, 2004
  8. ^ Two newly found space molecules. By: Goho, Alexandra, Science News, 00368423, 7/24/2004, Vol. 166, Issue 4
  9. ^ Chemical Precursors to Life Found in Space Scientists say that a universal prebiotic chemistry may be at work
  10. ^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Retrieved 30 July 2015.
  11. ^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
  12. ^ 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". Science. 349 (6247): 493. Bibcode:2015Sci...349..493B. doi:10.1126/science.aac5116. PMID 26228139.