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Propionaldehyde

From Wikipedia, the free encyclopedia
Not to be confused with propan o l .
Propionaldehyde
Skeletal formula of propionaldehyde (propanal)
Skeletal formula of propionaldehyde (propanal)
Flat structure
Flat structure
Ball-and-stick model
Names
IUPAC name
Propionaldehyde
Preferred IUPAC name
Propanal
Other names
  • Methylacetaldehyde
  • Propionic aldehyde
  • Propaldehyde
  • Propan-1-one
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
  • InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3   checkY
    Key: NBBJYMSMWIIQGU-UHFFFAOYSA-N   checkY
  • CCC=O
Properties
C 3 H 6 O
Molar mass 58.080  g·mol ?1
Appearance Colourless liquid
Odor Pungent and 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 cm 3 /mol
Viscosity 0.6 cP at 20 °C
Structure
C 1 , O: sp 2

C 2 , C 3 : sp 3

2.52 D
Hazards
GHS labelling :
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H225 , H302 , H315 , H318 , H332 , H335 [1]
P210 , P261 , P280 , P304+P340+P312 , P305+P351+P338 , P310 , P403+P235 [1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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. gasolineInstability 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 code
2
3
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).
checkY   verify  ( what is   checkY ☒N  ?)

Propionaldehyde or propanal is the organic compound with the formula CH 3 CH 2 CHO. 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.

Production [ edit ]

Propionaldehyde is mainly produced industrially by hydroformylation of ethylene :

CO + H 2 + C 2 H 4 → CH 3 CH 2 CHO

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]

Reactions [ edit ]

Main 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 α-functionalized derivatives (CH 3 CH(X)CHO) are chiral . If water is available, propionaldehyde exists in equilibrium with 1,1-propanediol , a geminal diol .

Uses [ edit ]

It is predominantly used as a precursor to trimethylolethane (CH 3 C(CH 2 OH) 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 CH 3 CH 2 CH=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, but is a lung and eye irritant and is a combustible liquid.

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 . ISBN   978-3527306732 .
  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. Archived from the original on 23 December 2018 . 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" (PDF) . Science . 349 (6247): 493. Bibcode : 2015Sci...349..493B . doi : 10.1126/science.aac5116 . PMID   26228139 .
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