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Malonic acid is acts as a building block in organic synthesis. It is also useful as a precursor for polyesters and alkyd resins, which is used in coating applications, thereby protecting against UV light, corrosion and oxidation. It acts as a cross linker in the coating industry and surgical adhesive. It finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.
Knoevenagel condensation with aldehydes yields substituted acrylic (e.g. cinnamic) acids; review: Org. React., 15, 204 (1967). For an example of the Doebner modification, using pyridine as solvent/base, see: Org. Synth. Coll., 3, 425 (1955); a catalytic amount of piperidine often gives superior results; see, e.g.: Org. Synth. Coll., 4, 327 (1963).
Bew, S. P.; Stephenson, R.; Rouden, J.; Ashford, P. A.; Bourane, M.; Charvet, A.; Dalstein, V. M. D.; Jauseau, R.; Gipson, G. D. H.; Lozano, L. A. M. Bioinspired, Base- and Metal-Free, Mild Decarboxylative Aldol Activation of Malonic Acid Half Thioesters Under Phase-Transfer Reaction Conditions. Adv. Synth. Catal. 2015, 357 (6), 1245-1257.
Nakamura, S.; Sano, M.; Toda, A.; Nakane, D.; Masuda, H. Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N-Sulfonyl Ketimines by Using N-Heteroarenesulfonyl Cinchona Alkaloid Amides. Chem. Eur. J. 2015, 21 (10), 3929-3932.
Dichiarazioni di rischio (UE): H302-H315-H318-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye damage. May cause respiratory irritation.
Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.