Succinaldehyde

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Succinaldehyde
Succindialdehyde.svg
Names
Preferred IUPAC name
Butanedial
Other names
Succinaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.304
Properties
C4H6O2
Molar mass 86.09
Appearance colourless liquid
Density 1.064 g/cm3
Boiling point 58 °C (136 °F; 331 K) at 9 mm Hg
with hydration
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Succinaldehyde or succindialdehyde is an organic compound with the formula (CH2CHO)2. Typical of other dialdehydes, succinaldehyde is highly reactive. Usually, it is handled as the hydrates or methanol-derived acetal. It is a precursor to tropinone.[1] It is used as a crosslinking agent but is less widely used than the related dialdehyde glutaraldehyde.

Preparation[edit]

Succinaldehyde is generated by the oxidation of THF with chlorine followed by hydrolysis and by the hydroformylation of acrolein derivatives.

In aqueous solution, the molecule hydrates and cyclizes.[2] In methanol it converts to the cyclic acetal, 2,5-dimethoxyltetrahydrofuran.[3]

References[edit]

  1. ^ U.S. Patent 2,710,883
  2. ^ Hardy, P. M.; Nicholls, A. C.; Rydon, H. N. "The hydration and polymerisation of succinaldehyde, glutaraldehyde, and adipaldehyde" J. Chem. Soc., Perkin Trans. 2, 1972, 2270-2278. doi:10.1039/P29720002270
  3. ^ Christian Kohlpaintner, Markus Schulte, Jürgen Falbe, Peter Lappe, Jürgen Weber "Aldehydes, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry 2008, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a01_321.pub2