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The Role of Brønsted and Water‐Tolerant Lewis Acid Sites in the Cascade Aqueous‐Phase Reaction of Triose to Lactic Acid
Author(s) -
Santos Kryslaine M. A.,
Albuquerque Elise M.,
Innocenti Giada,
Borges Luiz E. P.,
Sievers Carsten,
Fraga Marco A.
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900519
Subject(s) - chemistry , lewis acids and bases , lactic acid , catalysis , brønsted–lowry acid–base theory , aqueous solution , selectivity , glyceraldehyde , pyridine , aqueous two phase system , dehydration reaction , adsorption , inorganic chemistry , organic chemistry , bacteria , biology , dehydrogenase , genetics , enzyme
Aqueous‐phase conversion of glyceraldehyde to lactic acid was investigated over Nb 2 O 5 , TiO 2 , ZrO 2 and SnO 2 in a fixed‐bed up‐flow reactor. Special attention was given to the catalysts acidity regarding the type, amount, strength and tolerance to water of surface acid sites. These sites were assessed by infrared spectroscopy of pyridine adsorbed on dehydrated and hydrated catalysts as well as by isopropanol decomposition. It was found that Nb 2 O 5 and TiO 2 have the highest fraction of water‐tolerant Lewis acid sites (40 and 47 %), while only 6 % was estimated for ZrO 2 . No relevant Lewis acidity was observed on SnO 2 , but it was noticed the presence of strong base sites. The transformation of glyceraldehyde into lactic acid proceeded via a cascade reaction in which glyceraldehyde is firstly dehydrated to pyruvaldehyde, followed by its rearrangement to lactic acid with the addition of a water molecule. The dehydration step occurs on Brønsted acid sites and/or on water‐tolerant Lewis acid sites. These latter sites also determine the selectivity to lactic acid. Strong base sites promote glyceraldehyde fragmentation leading to formaldehyde with high selectivity.