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F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
Propionaldehyde
Skeletal formula of propionaldehyde (propanal) Flat structure
Names
IUPAC name
Propionaldehyde
Preferred IUPAC name
Other names
Propaldehyde
Propan-1-one
Identifiers
CAS Number
3D model (JSmol )
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.204
EC Number
KEGG
PubChem CID
RTECS number
UNII
UN number
1275
CompTox Dashboard (EPA )
InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3 Y
Key: NBBJYMSMWIIQGU-UHFFFAOYSA-N Y
Properties
Chemical formula
C 3 H 6 O
Molar mass
−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 )
Solubility in water
20 g/100 mL
Magnetic susceptibility (χ)
-34.32·10−6 cm 3
Viscosity
0.6 cP
Structure
Molecular shape
C 1 2
C 2 3 3
Dipole moment
2.52 D
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard 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
Flash point
−26 °C (−15 °F; 247 K )
Autoignition
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).
Infobox references
Chemical compound
Propionaldehyde or propanal is the organic compound with the formula CH3 CH 2 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 + H2 2 H 4 3 CH 2
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 ]
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 X )CHO) are chiral .
If water is available, propionaldehyde exists in equilibrium with 1,1-propanediol , a geminal diol .
It is predominantly used as a precursor to trimethylolethane (CH 3 CH 2 OH )3 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] [5] [verification needed With tert -butylamine3 CH 2 t organic synthesis .[6]
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]
With an LD50 of 1690 mg/kg (oral),[2]
References [ edit ]
^ a b c Hensel, A. (2018). "Propanal". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a22_157.pub3 . ISBN 978-3527306732
^ Hurd, Charles D.; Meinert, R. N. (1932). "Propionaldehyde". Organic Syntheses . 12 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 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 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). "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 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Propionaldehyde&oldid=1221097639 " C a t e g o r i e s : ● A l k a n a l s ● H a z a r d o u s a i r p o l l u t a n t s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h o u t I n C h I s o u r c e ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A l l p a g e s n e e d i n g f a c t u a l v e r i f i c a t i o n ● W i k i p e d i a a r t i c l e s n e e d i n g f a c t u a l v e r i f i c a t i o n f r o m O c t o b e r 2 0 2 1 ● C o m m o n s c a t e g o r y l i n k f r o m W i k i d a t a ● A r t i c l e s w i t h G N D i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 2 7 A p r i l 2 0 2 4 , a t 2 1 : 2 1 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w ●
T o g g l e l i m i t e d c o n t e n t w i d t h
