Chemical Properties
It is a Colorless transparent liquid that dissolves 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.
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.
Definition
ChEBI: Succinic aldehyde is an aldehyde.
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.
