Butyraldehyde

Last updated
Butyraldehyde [1]
Structural formula of butyraldehyde Butanal-skeletal.png
Structural formula of butyraldehyde
Flat structure Butyraldehyde flat structure.png
Flat structure
Ball-and-stick model Butyraldehyde-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
Butanal
Other names
Butyraldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.225 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-646-6
KEGG
PubChem CID
RTECS number
  • ES2275000
UNII
UN number 1129
  • InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Yes check.svgY
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYAZ
  • O=CCCC
Properties
C4H8O
Molar mass 72.107 g·mol−1
AppearanceColorless 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
1.3766
Viscosity 0.45  cP (20 °C)
2.72 D
Thermochemistry [2]
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)
−239.2 kJ·mol−1 (liquid)
−204.8 kJ·mol−1 (gas)
2470.34 kJ·mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg [3]
Danger
H225, H319 [3]
P210, P280, P302+P352, P304+P340, P305+P351+P338 [3]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
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):
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Production

Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:

CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO

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]

Reactions and uses

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]

A major use of butyraldehyde is in the production of bis(2-ethylhexyl) phthalate, a major plasticizer. Bis(2-ethylhexyl) phthalate.svg
A major use of butyraldehyde is in the production of bis(2-ethylhexyl) phthalate, a major plasticizer.

Related Research Articles

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

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.

In chemistry, a hydration reaction is a chemical reaction in which a substance combines with water. In organic chemistry, water is added to an unsaturated substrate, which is usually an alkene or an alkyne. This type of reaction is employed industrially to produce ethanol, isopropanol, and butan-2-ol.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Cumene process</span> Industrial process

The cumene process is an industrial process for synthesizing phenol and acetone from benzene and propylene. The term stems from cumene, the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), and independently by Heinrich Hock in 1944.

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 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.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

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.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

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.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

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, while esters provide alkyl silyl mixed acetals. Hydrosilylation has been called the "most important application of platinum in homogeneous catalysis."

<span class="mw-page-title-main">Isobutyraldehyde</span> Chemical compound

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 Cannizzaro reaction even though it has alpha hydrogen atom. It is a colorless volatile liquid.

<span class="mw-page-title-main">Pentanal</span> Chemical compound

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.

<span class="mw-page-title-main">TPPTS</span> Chemical compound

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.

<span class="mw-page-title-main">2-Ethylhexanal</span> Chemical compound

2-Ethylhexanal is the organic compound with the formula CH3CH2CH2CH2CH(C2H5)CHO. A colorless liquid, it is produced on a large scale industrially as a precursor to 2-ethylhexanoic acid and 2-ethylhexanol, both used as precursors to plasticizers. It was studied in the detergent industry since the 1930s.

References

  1. ↑ Merck Index, 11th Edition, 1591.
  2. ↑ CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN   978-1-4987-5428-6. OCLC   930681942.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link)
  3. 1 2 3 Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  4. 1 2 Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2. ISBN   978-3-527-30673-2.
  5. ↑ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sörensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBN   978-3-527-30673-2.
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