Propionaldehyde or propanal is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃CH₂CHO. It is the 3-carbon

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

. It is a colourless, flammable liquid with a pungent and fruity odour. It is produced on a large scale industrially.

Production

Propionaldehyde is mainly produced industrially by

hydroformylation In organic chemistry, hydroformylation, also known as oxo synthesis or oxo process, is an industrial process for the production of aldehydes () from alkenes (). This chemical reaction entails the net addition of a formyl group () and a hydrogen ...

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

: :CO + H₂ + C₂H₄ → CH₃CH₂CHO In this way, several hundred thousand tons are produced annually.

Laboratory preparation

Propionaldehyde may also be prepared by oxidizing 1-propanol with a mixture of

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

and

potassium dichromate Potassium dichromate is the inorganic compound with the formula . An orange solid, it is used in diverse laboratory and industrial applications. As with all hexavalent chromium compounds, it is chronically harmful to health. It is a crystalline ...

. 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 Propionic acid (, from the Greek language, Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula . It is a ...

Reactions

Propionaldehyde exhibits the reactions characteristic of alkyl

s, e.g. hydrogenation,

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

s, oxidations, etc. It is the simplest aldehyde with a prochiral methylene such that α-functionalized derivatives (CH₃CH(X)CHO) are

chiral Chirality () is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek language, Greek (''kheir''), "hand", a familiar chiral object. An object or a system is ''chiral'' if it is dist ...

. If water is available, propionaldehyde exists in equilibrium with 1,1-propanediol, a

geminal diol A geminal diol (or gem-diol for short) is any organic compound having two hydroxyl functional groups () bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal ...

. 2-Methylpentanal () arises by

of propionaldehyde followed by dehydration and hydrogenation.

Uses

Both industrially and in the laboratory, propionaldehyde has primary application as a chemical building block. It is predominantly used as a precursor to

trimethylolethane Trimethylolethane (TME) is the organic compound with the formula CH3C(CH2OH)3. This colorless solid is a triol, as it contains three hydroxy functional groups. More specifically, it features three primary alcohol groups in a compact neopentyl str ...

(CH₃C(CH₂OH)₃) through a

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

with

formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...

. This triol is an important intermediate in the production of

alkyd An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term ''alkyd'' is ...

resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...

s. It is used in the synthesis of several common

aroma compound An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

s ( cyclamen aldehyde, helional, lilial). Reduction of propionaldehyde gives ''n''propanol, and

reductive amination Reductive amination (also known as reductive alkylation) is a form of amination that converts a carbonyl group to an amine via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde. It is a common method to make amine ...

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

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s or

glycol ether Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while ha ...

s, or as a gentle alkylant for primary and secondary

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

s. Oxidants instead give

and propionates, typically used as

preservatives A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or b ...

Laboratory uses

Many laboratory uses exploit its participation in condensation reactions. With ''tert''-butylamine it gives CH₃CH₂CH=N-''t''-Bu, a three-carbon building block used in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

Extraterrestrial occurrence

Propionaldehyde along with

acrolein Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat ...

has been detected in the

molecular cloud A molecular cloud—sometimes called a stellar nursery if star formation is occurring within—is a type of interstellar cloud of which the density and size permit absorption nebulae, the formation of molecules (most commonly molecular hydrogen, ...

Sagittarius B2 Sagittarius B2 (Sgr B2) is a giant molecular cloud of gas and dust that is located about from the center of the Milky Way. This complex is the largest molecular cloud in the vicinity of the core and one of the largest in the galaxy, spanning a re ...

near the center of the

Milky Way Galaxy The Milky Way or Milky Way Galaxy is the galaxy that includes the Solar System, with the name describing the galaxy's appearance from Earth: a hazy band of light seen in the night sky formed from stars in other arms of the galaxy, which are ...

, about 26,000 light years from Earth.Chemical Precursors to Life Found in Space Scientists say that a universal prebiotic chemistry may be at work
/ref> Measurements by the COSAC and Ptolemy instruments on

comet A comet is an icy, small Solar System body that warms and begins to release gases when passing close to the Sun, a process called outgassing. This produces an extended, gravitationally unbound atmosphere or Coma (cometary), coma surrounding ...

67/P surface, revealed sixteen

s, four of which were seen for the first time on a comet, including

acetamide Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is an amide derived from ammonia and acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound ''N'',''N''-dime ...

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

methyl isocyanate Methyl isocyanate (MIC) is an organic compound with the molecular formula CH3NCO. Synonyms are isocyanatomethane and methyl carbylamine. Methyl isocyanate is an intermediate chemical in the production of carbamate pesticides and Haffmann Bromam ...

and propionaldehyde.

Safety

With an

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...

of 1690 mg/kg (oral), propionaldehyde exhibits low acute toxicity, but is a lung and eye irritant and is a combustible liquid.

References

{{Authority control Alkanals