Yamaguchi, Sho, et al. ChemSusChem 8.5 (2015): 853-860.
1,3-Dihydroxyacetone (DHA), a triose sugar derived from glucose or fructose via a [3+3] retro-aldol reaction, plays a crucial role in catalytic transformations toward valuable chemical intermediates. Recent studies have demonstrated its effective conversion with formaldehyde into α-hydroxy-γ-butyrolactone (AHA), a key building block for pharmaceuticals and fine chemicals.
In this transformation, DHA undergoes sequential dehydration and alcohol addition, followed by proton transfer, leading to the formation of α-hydroxy-γ-butyrolactone. Among various Lewis acid catalysts examined, tin(IV) chloride exhibited the highest catalytic performance. The reaction mechanism is closely related to formose-type chemistry, involving aldol and retro-aldol reactions, as well as aldose-ketose tautomerization. The pathway mirrors the one-pot catalytic conversion of glycolaldehyde into four-carbon α-hydroxy acid esters, further demonstrating the versatility of DHA in synthetic chemistry.
Advanced spectroscopic techniques, including ¹¹⁹Sn NMR, have provided detailed insights into the catalyst's valence state and mechanistic aspects of the reaction. Understanding these pathways not only optimizes the efficiency of DHA-based transformations but also contributes to the broader development of biomass-derived chemical syntheses.
These findings highlight DHA as a promising intermediate in sustainable chemical production, offering new opportunities for the synthesis of high-value lactones and related compounds.
Jolimaitre, E., et al. Catalysis Science & Technology 8.5 (2018): 1349-1356.
Dihydroxyacetone (DHA) serves as a crucial intermediate in the catalytic conversion to lactic acid (LA), a key platform chemical for bioplastics and pharmaceuticals. In aqueous media, DHA undergoes a sequential transformation via pyruvaldehyde (PA) under the influence of homogeneous metal salt catalysts. A kinetic study has revealed that both Brønsted and Lewis acids catalyze the DHA-to-PA dehydration step, whereas only Lewis acids facilitate the subsequent PA-to-LA conversion.
Among various catalysts tested, aluminum salts exhibited the highest efficiency. Investigations confirmed that in situ-formed hydroxylaluminium complexes, such as [Al(OH)h](3-h)+, are the most active Lewis acid species driving the reaction. Kinetic modeling accounted for the thermodynamic equilibrium between DHA and its isomer glyceraldehyde (GLY), ensuring a more accurate representation of the reaction mechanism. Experimental validation using high-performance liquid chromatography (HPLC) demonstrated excellent agreement between model predictions and observed data.
This mechanistic insight into DHA's catalytic transformation provides a foundation for optimizing reaction conditions and catalyst selection, enhancing the sustainable production of LA from biomass-derived precursors. The study underscores DHA's significance as a versatile feedstock in green chemistry, offering a pathway to value-added chemicals through well-controlled catalytic processes.
Lux, Susanne, and Matthäus Siebenhofer. Chemical and biochemical engineering quarterly 29.4 (2015): 575-585.
Dihydroxyacetone (DHA), a primary oxidation product of glycerol, serves as a crucial intermediate in the catalytic conversion to lactic acid (LA), a valuable chemical in food, pharmaceutical, and biodegradable polymer industries. Recent studies demonstrate that DHA undergoes sequential dehydration to pyruvaldehyde (PA) and subsequent intramolecular Cannizzaro-type rearrangement to LA in aqueous media.
The reaction is significantly influenced by the presence of Brønsted acids and Lewis acids. HCl, when used in excess under reflux boiling conditions, achieves an LA yield of 83%, facilitating DHA dehydration to PA. Additionally, Al3+ ions (e.g., from Al2(SO4)3) enhance the conversion of PA to LA, yielding up to 78% LA under optimized conditions. The hydrolysis of aluminium aqua complexes forms hydroxylaluminium species, which act as the most efficient Lewis acid catalysts in the transformation.
This non-fermentative catalytic pathway for DHA conversion to LA presents a promising alternative to traditional fermentation processes, aligning with sustainable chemical manufacturing goals by utilizing glycerol, a biodiesel by-product, as a renewable feedstock.
What is the CAS number for dihydroxyacetone?
The CAS number for dihydroxyacetone is 96-26-4.
What are some synonyms for dihydroxyacetone?
Some synonyms for dihydroxyacetone are 1,3-Dihydroxyacetone and 2-Propanone, 1,3-dihydroxy-.
What is the molecular weight of dihydroxyacetone?
The molecular weight of dihydroxyacetone is 90.08.
What is the molecular formula of dihydroxyacetone?
The molecular formula of dihydroxyacetone is C3H6O3.
What percentage of actives does dihydroxyacetone contain?
Dihydroxyacetone contains 95% actives.
In what physical state is dihydroxyacetone?
Dihydroxyacetone is in a solid physical state.
What are some typical applications of dihydroxyacetone?
Some typical applications of dihydroxyacetone are as a dispersing agent, emulsifying agent, tanning agent, and intermediate in organic synthesis.
How is dihydroxyacetone used as a tanning agent?
Dihydroxyacetone is used in tanning products to give the skin a sun-kissed look without exposure to harmful UV rays.
What is the chemical structure of dihydroxyacetone?
Dihydroxyacetone has a ketone group (C=O) and two hydroxyl groups (-OH).
How can dihydroxyacetone be used as an intermediate in organic synthesis?
Dihydroxyacetone can be used to synthesize other compounds by undergoing chemical reactions to form new products.
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