Isobutyraldehyde

Last updated
Isobutyraldehyde
Isobutyraldehyde 200.svg
Isobutyraldehyde 3D ball.png
Names
Preferred IUPAC name
2-Methylpropanal
Other names
2-Methylpropionaldehyde
Identifiers
3D model (JSmol)
605330
ChEBI
ChemSpider
ECHA InfoCard 100.001.045 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-149-6
1658
PubChem CID
RTECS number
  • NQ4025000
UNII
UN number 2045
  • InChI=1S/C4H8O/c1-4(2)3-5/h3-4H,1-2H3 Yes check.svgY
    Key: AMIMRNSIRUDHCM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8O/c1-4(2)3-5/h3-4H,1-2H3
    Key: AMIMRNSIRUDHCM-UHFFFAOYAE
  • CC(C)C=O
Properties
C4H8O
Molar mass 72.11 g/mol
Appearancecolourless liquid
Odor Pungent; straw-like
Density 0.79 g/cm3
Melting point −65 °C (−85 °F; 208 K)
Boiling point 63 °C (145 °F; 336 K)
moderate
Solubility in other solventsmiscible in organic solvents
-46.38·10−6 cm3/mol
1.374
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H319
P210, P233, P240, P241, P242, P243, P264, P280, P303+P361+P353, P305+P351+P338, P337+P313, P370+P378, P403+P235, P501
Flash point −19 °C; −2 °F; 254 K
Related compounds
Related alkyl aldehydes
Lilial

Hexyl cinnamaldehyde
2-Methylundecanal

Related compounds
Butyraldehyde
Propionaldehyde
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 ?)

Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). [1] 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.

Contents

Synthesis

Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually. [2]

Biological routes

In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. E. coli as well as several other organisms has been genetically modified to produce isobutanol. α-Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol: [3]

(CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2
(CH3)2CHCHO + NADH + H+ → (CH3)2CHCH2OH + NAD+

It can also be produced using engineered bacteria. [4]

Other routes

Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutyraldehyde.

Reactions

Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde. [2] The latter is a precursor to vitamin B5. [5]

Pantothenic acid synthesis.svg

Related Research Articles

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<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

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<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

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

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

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

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.

<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">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

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

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α-Ketoisovaleric acid Chemical compound

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<span class="mw-page-title-main">2-Methyl-1-butanol</span> Chemical compound

2-Methyl-1-butanol (IUPAC name, also called active amyl alcohol) is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. This colorless liquid occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.

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

Hydroxypivaldehyde is the organic compound with the formula HOCH2(CH3)2CCHO. A colorless liquid, it is produced by condensation of formaldehyde and isobutyraldehyde:

References

  1. Isobutyraldehyde is a retained trivial name under the IUPAC rules.Panico, R.; Powell, W. H.; Richer, J. C., eds. (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds . IUPAC/Blackwell Science. ISBN   0-632-03488-2.
  2. 1 2 Boy Cornils, Richard W. Fischer, Christian Kohlpaintner "Butanals" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a04_447
  3. Atsumi, Shota; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature. 451 (7174): 86–89. Bibcode:2008Natur.451...86A. doi:10.1038/nature06450. PMID   18172501. S2CID   4413113.
  4. Atsumi, Shota; Wendy Higashide; James C. Liao (November 2009). "Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde". Nature Biotechnology. 27 (12): 1177–1180. doi:10.1038/nbt.1586. PMID   19915552. S2CID   1492698.
  5. Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition. 51 (52): 12975. doi:10.1002/anie.201205886. PMID   23208776.