Names | |
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Preferred IUPAC name Butanal | |
Other names Butyraldehyde | |
Identifiers | |
3D model (JSmol) | |
3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.225 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1129 |
CompTox Dashboard (EPA) | |
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Properties | |
C4H8O | |
Molar mass | 72.107 g·mol−1 |
Appearance | Colorless liquid |
Odor | Pungent, aldehyde odor |
Density | 0.8016 g/mL |
Melting point | −96.86 °C (−142.35 °F; 176.29 K) |
Boiling point | 74.8 °C (166.6 °F; 347.9 K) |
Critical point (T, P) | 537 K (264 °C), 4.32 MPa (42.6 atm) |
7.6 g/100 mL (20 °C) | |
Solubility | Miscible with organic solvents |
log P | 0.88 |
−46.08·10−6 cm3/mol | |
Refractive index (nD) | 1.3766 |
Viscosity | 0.45 cP (20 °C) |
2.72 D | |
Thermochemistry [2] | |
Heat capacity (C) | 163.7 J·mol−1·K−1 (liquid) 103.4 J·mol−1·K−1 (gas) |
Std molar entropy (S⦵298) | 246.6 J·mol−1·K−1 (liquid) 343.7 J·mol−1·K−1 (gas) |
Std enthalpy of formation (ΔfH⦵298) | −239.2 kJ·mol−1 (liquid) −204.8 kJ·mol−1 (gas) |
Std enthalpy of combustion (ΔcH⦵298) | 2470.34 kJ·mol−1 |
Hazards | |
GHS labelling: | |
[3] | |
Danger | |
H225, H319 [3] | |
P210, P280, P302+P352, P304+P340, P305+P351+P338 [3] | |
NFPA 704 (fire diamond) | |
Flash point | −7 °C (19 °F; 266 K) |
230 °C (446 °F; 503 K) | |
Explosive limits | 1.9–12.5% |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 2490 mg/kg (rat, oral) |
Safety data sheet (SDS) | Sigma-Aldrich |
Related compounds | |
Related aldehyde | Propionaldehyde Pentanal |
Related compounds | Butan-1-ol Butyric acid, isobutyraldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.
Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:
Traditionally, hydroformylation was catalyzed by cobalt carbonyl but rhodium complexes are more common. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand tppts. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter (less dense) immiscible phase. About 6 billion kilograms are produced annually in this manner. Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde. [4]
Butyraldehyde undergoes reactions typical of alkyl aldehydes, and these define many of the uses of this compound. Important reactions include hydrogenation to the alcohol, oxidation to the acid, and base-catalyzed condensation. In the presence of a base, two equivalents of butyraldehyde undergoe aldol condensation to give 2-ethylhexenal. This unsaturated aldehyde is then partially hydrogenated to form 2-ethylhexanal, a precursor to plasticizers such as bis(2-ethylhexyl) phthalate. [4]
Butyraldehyde is a component in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins. [5]
In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organic compounds. Hydrogenation typically constitutes the addition of pairs of hydrogen atoms to a molecule, often an alkene. Catalysts are required for the reaction to be usable; non-catalytic hydrogenation takes place only at very high temperatures. Hydrogenation reduces double and triple bonds in hydrocarbons.
A diol is a chemical compound containing two hydroxyl groups. An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting groups of carbonyl groups, making them essential in synthesis of organic chemistry.
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At its simplest, it's a useful way of converting alkanes, which are relatively inert and thus low-valued, to olefins, which are reactive and thus more valuable. Alkenes are precursors to aldehydes, alcohols, polymers, and aromatics. As a problematic reaction, the fouling and inactivation of many catalysts arises via coking, which is the dehydrogenative polymerization of organic substrates.
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 atom to a carbon-carbon double bond. This process has undergone continuous growth since its invention: production capacity reached 6.6×106 tons in 1995. It is important because aldehydes are easily converted into many secondary products. For example, the resultant aldehydes are hydrogenated to alcohols that are converted to detergents. Hydroformylation is also used in speciality chemicals, relevant to the organic synthesis of fragrances and pharmaceuticals. The development of hydroformylation is one of the premier achievements of 20th-century industrial chemistry.
In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst in a solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in distinct phases, typically solid and gas, respectively. The term is used almost exclusively to describe solutions and implies catalysis by organometallic compounds. Homogeneous catalysis is an established technology that continues to evolve. An illustrative major application is the production of acetic acid. Enzymes are examples of homogeneous catalysts.
In organic chemistry, terminal alkenes are a family of organic compounds which are alkenes with a chemical formula CxH2x, distinguished by having a double bond at the primary, alpha (α), or 1- position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications.
Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.
Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.
Hydroperoxides or peroxols are compounds of the form ROOH, where R stands for any group, typically organic, which contain the hydroperoxy functional group. Hydroperoxide also refers to the hydroperoxide anion and its salts, and the neutral hydroperoxyl radical (•OOH) consist of an unbond hydroperoxy group. When R is organic, the compounds are called organic hydroperoxides. Such compounds are a subset of organic peroxides, which have the formula ROOR. Organic hydroperoxides can either intentionally or unintentionally initiate explosive polymerisation in materials with unsaturated chemical bonds.
1,3-Propanediol is the organic compound with the formula CH2(CH2OH)2. This 3-carbon diol is a colorless viscous liquid that is miscible with water.
The Guerbet reaction, named after Marcel Guerbet (1861–1938), is an organic reaction that converts a primary alcohol into its β-alkylated dimer alcohol with loss of one equivalent of water. The process is of interest because it converts simple inexpensive feedstocks into more valuable products. Its main disadvantage is that the reaction produces mixtures.
Hydrosilylation, also called catalytic hydrosilation, describes the addition of Si-H bonds across unsaturated bonds. Ordinarily the reaction is conducted catalytically and usually the substrates are unsaturated organic compounds. Alkenes and alkynes give alkyl and vinyl silanes; aldehydes and ketones give silyl ethers. Hydrosilylation has been called the "most important application of platinum in homogeneous catalysis."
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizaro reaction even though it has alpha hydrogen atom. It is a colorless volatile liquid.
Pentanal is the organic compound with molecular formula C4H9CHO. Classified as an alkyl aldehyde, it is a colorless volatile liquid. Its odor is described as fermented, bready, fruity, nutty, berry.
In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.
Octanal is the organic compound, an aldehyde, with the chemical formula CH3(CH2)6CHO. A colorless fragrant liquid with a fruit-like odor, it occurs naturally in citrus oils. It is used commercially as a component in perfumes and in flavor production for the food industry. It is usually produced by hydroformylation of heptene and the dehydrogenation of 1-octanol.
Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants.
3,3′,3′′-Phosphanetriyltris(benzenesulfonic acid) trisodium salt (abbreviated TPPTS), is an organic compound that is also known as sodium triphenylphosphine trisulfonate. The compound has the formula P(C6H4SO3Na)3. This white solid is an unusual example of a water-soluble phosphine. Its complexes are also water-soluble. Its complex with rhodium is used in the industrial production of butyraldehyde.
Organorhodium chemistry is the chemistry of organometallic compounds containing a rhodium-carbon chemical bond, and the study of rhodium and rhodium compounds as catalysts in organic reactions.
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