Chemical Properties
Liquid. Soluble in water, alcohol, and
ether. The name succinaldehyde is often incorrectly
used in commerce as a synonym for succinic anhydride.
Uses
Succinaldehyde (SA) was added directly into UF resins before application for plywood production; these urea-formaldehyde-succinaldehyde (UFSA) resins, as they were formed during curing, improved markedly the water resistance of the hardened UF bondline as well as decreased its formaldehyde emission.
Definition
ChEBI: Succinic aldehyde is an aldehyde.
Preparation
Preparation method of succinaldehyde: Using furan as the raw material, 2,5-Dihydro-2,5-dimethoxyfuran is prepared by electrolysis, followed by hydrogenation and hydrolysis to obtain succinaldehyde. Alternatively, Cyclododeca-1,5,9-triene can be used as the raw material. In ethyl acetate, at -20 to 10°C, it is oxidized with 3% ozone to produce triene ozonide. It is then subjected to catalytic hydrogenation with 5% lead-activated carbon at room temperature to prepare succinaldehyde.
Precautions
succindialdehyde rapidly polymerizes and has to be used immediately after distillation. Use in a fume hood.
References
[1] BENNETT S H. Organocatalytic Dimerization of Succinaldehyde[J]. Organic Syntheses, 2022. DOI:10.15227/orgsyn.099.0139.
[2] D. P. KAMDEM A. J A Pizzi. Durability of heat-treated wood[J]. European Journal of Wood and Wood Products, 2002, 60 1: 1-6. DOI:10.1007/s00107-001-0261-1.
[3] MCINTOSH J M. ChemInform Abstract: Robinson-Schopf Condensations with Succinaldehyde.[J]. ChemInform, 1988, 19 26. DOI:10.1002/chin.198826164.
[4] STEVEN H. BENNETT Prof. Dr V K A Dr Graeme Coulthard. Prostaglandin Total Synthesis Enabled by the Organocatalytic Dimerization of Succinaldehyde[J]. Chemical record, 2020, 20 9: 936-947. DOI:10.1002/tcr.202000054.
