ChemInform Abstract: LEVULINIC ACID. I. ITS PREPARATION AND USE

Levulinic acid in organic synthesis

“…The main physical constants for LA are as follows: d 20 4 1.140, d 25 4 1.1447; n 20 d 1.4796, n 25 d 1.441; surface tension 39.7 dyne cm 71 (25 8C); heat of vaporisation (150 8C) 0.58 kJ mol 71 and heat of fusion 79.8 J mol 71 (see Ref. 4).…”

Oxocarboxylic Acids

“…It was first described and named levulinic acid by GROTE and TOLLENS in 1875 [34]. Only since 1960 has levulinic acid gained commercial importance [35], [36].…”

“…Levulinic acid is produced industrially from sugar polymers such as cellulose or starch via the monomeric hexoses [36] according to many patented processes. The reaction is usually acid catalyzed: D-glucose [50-99-7] is formed first and is then isomerized enzymatically to D-fructose [57-48-7].…”

“…D-Fructose is subsequently converted to hydroxymethylfurfural [67-47-0], an intermediate that reacts further to form levulinic acid. The classical levulinic acid synthesis, the treatment of D-fructose with hydrochloric acid, is also being used [36].…”

“…The LD 50 (oral, rat) is 1850 mg/kg. Levulinic acid can cause acid burns, and concentrated solutions can cause irritation of the skin and mucous membranes [36].…”