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Adipaldehyde

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Adipaldehyde
Names
IUPAC name hexanedial
Other names 1,4-Butane dicarboxaldehyde, 1,6-hexanedial
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.731 Edit this at Wikidata
EC Number
  • 214-003-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10O2/c7-5-3-1-2-4-6-8/h5-6H,1-4H2Key: UMHJEEQLYBKSAN-UHFFFAOYSA-N
SMILES
  • C(CCC=O)CC=O
Properties
Chemical formula C6H10O2
Molar mass 114.144 g·mol
Appearance colorless liquid
Density 1.003 g/cm
Melting point −8 °C (18 °F; 265 K)
Boiling point 68–70 °C (154–158 °F; 341–343 K) 3 mm Hg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Adipaldehyde is the organic compound with the formula (CH2)4(CHO)2. It is a colorless oil that is usually encountered as an aqueous solution because it is highly reactive like many dialdehydes. The compound has attracted interest as a precursor to nylon-related polymers. It can be produced by double hydroformylation of 1,3-butadiene, but this methodology has not achieved commercialization. It has been prepared by oxidation of 1,6-hexanediol with pyridinium chlorochromate.

References

  1. Hardy, P. M.; Nicholls, A. C.; Rydon, H. N. (1972). "The Hydration and Polymerisation of Succinaldehyde, Glutaraldehyde, and Adipaldehyde". Journal of the Chemical Society, Perkin Transactions 2 (15): 2270. doi:10.1039/P29720002270.
  2. Yu, Si-min; Snavely, William K.; Chaudhari, Raghunath V.; Subramaniam, Bala (2020). "Butadiene hydroformylation to adipaldehyde with Rh-based catalysts: Insights into ligand effects". Molecular Catalysis. 484. doi:10.1016/j.mcat.2019.110721. S2CID 213312335.
  3. Corey, E.J.; Suggs, J.William (1975). "Pyridinium Chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds". Tetrahedron Letters. 16 (31): 2647–2650. doi:10.1016/s0040-4039(00)75204-x.
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