Propionaldehyde - Wikipedia

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Not to be confused with propanol. Propionaldehyde

Names

IUPAC name Propionaldehyde

Preferred IUPAC name Propanal

Other names

Methylacetaldehyde
Propionic aldehyde
Propaldehyde
Propan-1-one

Identifiers

CAS Number

123-38-6 Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:17153 Y

ChEMBL

ChEMBL275626 Y

ChemSpider

512 Y

ECHA InfoCard

100.004.204

EC Number

204-623-0

KEGG

C00479

PubChem CID

RTECS number

UE0350000

UNII

AMJ2B4M67V Y

UN number

1275

CompTox Dashboard (EPA)

DTXSID2021658

InChI

InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3 YKey: NBBJYMSMWIIQGU-UHFFFAOYSA-N Y

SMILES

CCC=O

Properties

Chemical formula

C3H6O

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)

Solubility in water

20 g/100 mL

Magnetic susceptibility (χ)

−34.32·10−6 cm3/mol

Viscosity

0.6 cP at 20 °C

Structure

Molecular shape

C1, O: sp2

C2, C3: sp3

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 (fire diamond)

2 3 2

Flash point

−26 °C (−15 °F; 247 K)

Autoignitiontemperature

175 °C (347 °F; 448 K)

Related compounds

Related aldehydes

AcetaldehydeButyraldehyde

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Chemical compound

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.

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]

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 (CH3CH(X)CHO) are chiral. If water is available, propionaldehyde exists in equilibrium with 1,1-propanediol, a geminal diol.

2-Methylpentanal (CH3CH2CH2CH(CH3)CHO) arises by aldol condensation of propionaldehyde followed by dehydration and hydrogenation.

Uses

[edit]

Both industrially and in the laboratory, propionaldehyde has primary application as a chemical building block.[2]: 4 [4]

It 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).[2]

Reduction of propionaldehyde gives n‑propanol, and reductive amination gives propanamine. Rising demand for non-chlorocarbon solvents has caused some manufacturers to substitutively brominate n‑propanol to propyl bromide. However, the majority of applications use n‑propanol proper in esters or glycol ethers, or as a gentle alkylant for primary and secondary amines.[2]: 5

Oxidants instead give propionic acid and propionates, typically used as preservatives.[2]: 5

Laboratory uses

[edit]

Many laboratory uses exploit its participation in condensation reactions.[5][better source needed] 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, 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 d e f 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.
^ See, e.g., Sessler, Jonathan L.; Mozaffari, Azadeh; Johnson, Martin R. (1992). "3,4-Diethylpyrrole and 2,3,7,8,12,13,17,18-Octaethylporphyrin". Organic Syntheses. 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.rp271.
^ 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.

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Molecules detected in outer space

Molecules

Diatomic	Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Imidogen Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur mononitride Sulfur monoxide Titanium(II) oxide
Triatomic	Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene Methylidynephosphane N2H+ Nitrous oxide Nitroxyl Ozone Potassium cyanide Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Trihydrogen cation Water
Fouratoms	Acetylene Ammonia Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methyl cation Methyl radical Methylene amidogen Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thiocyanic acid Thioformaldehyde Tricarbon monosulfide Tricarbon monoxide
Fiveatoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Sixatoms	Acetonitrile Cyanobutadiynyl radical Cyclopropenone Diacetylene E-Cyanomethanimine Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Sevenatoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Methyl isocyanate Methylamine Propyne Vinyl alcohol
Eightatoms	Acetic acid Acrolein Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methyl formate Methylcyanoacetylene
Nineatoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanethiol Ethanol Methyldiacetylene N-Methylformamide Octatetraynyl radical Propene Propionitrile
Tenatomsor more	Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) Butyronitrile C70 fullerene Cyanodecapentayne Ethyl formate Ethylene glycol Heptatrienyl radical Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Pyrimidine