2005
DOI: 10.1039/b501964h
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Tin-catalyzed conversion of trioses to alkyl lactates in alcohol solution

Abstract: Tin chlorides, SnCl2 and SnCl4.5H2O are excellent catalysts for the reactions of trioses, dihydroxyacetone and glyceraldehyde with alcohols (MeOH, EtOH and nBuOH) to give alkyl lactates, whose reaction mechanism involves the intermediary formation of pyruvic aldehyde followed by its esterification, which is distinctively promoted by tin halides.

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Cited by 167 publications
(140 citation statements)
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“…Recently, homogeneous metal salts have also been reported to catalyse this transformation [45,46]. A parallel undesired pathway involves the catalytic oxidation of glyceraldehyde/dihydroxyacetone to glyceric acid and subsequently to further oxidation and C-C splitting products like tartronic acid, glycolic acid, oxalic acid, acetic acid and formic…”
Section: Reaction Pathwaysmentioning
confidence: 99%
“…Recently, homogeneous metal salts have also been reported to catalyse this transformation [45,46]. A parallel undesired pathway involves the catalytic oxidation of glyceraldehyde/dihydroxyacetone to glyceric acid and subsequently to further oxidation and C-C splitting products like tartronic acid, glycolic acid, oxalic acid, acetic acid and formic…”
Section: Reaction Pathwaysmentioning
confidence: 99%
“…Hence, it is widely used in the food, pharmaceutical, cosmetic, and chemical industries. LA in particular has received much attention recently as a monomer for the production of biodegradable polylactic acid (PLA) or polylactide (Hayashi and Sasaki 2005;de Clippel et al 2012). Currently, lactic acid is produced by the fermentation method.…”
Section: Introductionmentioning
confidence: 99%
“…Alternative chemocatalytic approaches toward lactic acid and alkyl lactates from carbohydrates are therefore of great interest. [17][18][19][20][21][22][23][24] One of the key reaction steps in this regard is the rearrangement of the pyruvic aldehyde intermediate to lactate via a hydride shift mechanism. [23,25] Zeolites and mesoporous silica materials containing Lewis acidic functional groups have attracted attention as promising catalysts for carbohydrate isomerization reactions.…”
mentioning
confidence: 99%