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butyraldehyde

Product name butyraldehyde
Synonyms butanal
GOST no data
CAS 123-72-8

Butyraldehyde (CH3CH2CH2CHO) is a clear, colorless, flammable liquid with a pungent aldehyde odor. It is fully miscible with diethyl ether, acetone, chloroform, ethanol, methanol, tetrahydrofuran and a number organic solvents. Solubility in water is 8.7% wt at 0°C. Butyraldehyde forms azeotropes with water (bp 68°C, 12% wt of water), methanol (62.6°C and 51% wt), ethanol (62.6°C and 60.6%).

Butyraldehyde is found in nature as a component of lavender and eucaliptus oil, it contains in tea, acacia and mulberry-tree leaf.

It show chemical properties of typical aliphatic aldehyde. Butyraldehyde is trimerized on air to form parabutyraldehyde (2,4,6-tripropyl-1,3,5-trioxane):

butyraldehyde trimerization into parabutyraldehyde


In the presence of bases butyraldehyde undergoes dimerization to give butylaldol (2-ethyl-3-hydroxyhexanal). This process is known as aldol condensation. Then butyraldol is reduced on Raney nickel to form 2-ethylhexanol:

2-ethylhexanol synthesis from butyraldehyde


Butanal can be catalytically hydrogenated to give n-butyl alcohol. Oxidation of butyraldehyde resilts in butanoic acid. Interaction with ketene leads to β-caprolacton formation:

reaction of butyraldehyde with ketene


Butanal is a toxic compound by inhalation. It may irritate skin and eyes.

Production.

Most common way for industrial butanal production is via hydroformylation of propylene (oxosynthesis process) at 80-120°C and pressure 0.7-3.0MPa in the presence of catalyst (cobalt carbonyl Co2(CO)8 or ruthenium complexes). This reaction results in the mixture of butyraldehyde and isobutyraldehyde with the ratio 3:1, which then is separated by rectification:

2CH3CH=CH2 + 2CO + 3H2O → CH3CH2CH2CHO + (CH3)2CHCHO

Uses.

  • Almost of produced butyraldehyde is used as a feedstock for 2-ethylhexyl alcohol manufacture;
  • as a source for n-butyl alcohol and n-butanoic acid production;
  • as an intermediate in making of polyvinylbutyral;
  • to make modified phenol-, carbamide- and aniline-formaldehyde resins;
  • as an intermediate in industrial synthesis of 2-ethylhexane-1,3-diol, a repellent and a solvent;

  • Manufacturer(s) no data
    Chemical structure of butyraldehyde

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