52217-02-4

Basic information

• Product Name: 3-hydroxy-2-butanon
• CAS NO: 52217-02-4
• Molecular Weight: 88.1063
• Mol File: 52217-02-4.mol

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-2-butanon(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2-butanon(52217-02-4)
• EPA Substance Registry System: 3-hydroxy-2-butanon(52217-02-4)

Safety Data

• Hazardous Substances Data: 52217-02-4(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 78-97-7 2-hydroxy-propionitrile 
• 50-00-0 formaldehyd 
• 849585-22-4 LACTIC ACID 
• 57-48-7 D-Fructose 
• 58-86-6 D-xylose 
• 3458-28-4 D-Mannose 
• 6014-42-2 L-rhamnose 
• 328-42-7 Oxalacetic acid 
• 64-17-5 ethanol 
• 1029272-42-1 (2R,3S)-2,3-butanediol 
• 24347-58-8 (R,R)-2,3-butandiol 
• 69-65-8 mannitol 
• 5328-37-0 L-arabinose 

Downstream Products

• 42479-40-3 biacetyl bis(N-methyl-N-phenylhydrazone) 
• 2861-48-5 butane-2,3-dione-bis-phenylhydrazone 
• 2302-39-8 4,5-dimethylimidazole 
• 513-85-9 2.3-butanediol 
• 4906-24-5 3-acetoxy-2-butanone 
• 40722-10-9 N,N'-bis(cyclohexyl)-2,3-butanediimine 
• 13682-20-7 4,5-dimethyl-2-phenyl-1H-imidazole 
• 117668-70-9 3-(p-tolylamino)butan-2-one 
• 2199-54-4 2,4,5-trimethyl-3-ethoxycarbonylpyrrole 
• 21478-63-7 benzoic acid 1-methyl-2-oxo-propyl ester 
• 822-90-2 2,4,5-trimethyl-1H-imidazole 
• 101258-83-7 3-Butylamino-butanon-(2) 
• 94622-67-0 butane-2,3-dione-bis-(4-nitro-phenylhydrazone) 
• 35015-94-2 3-hydroxy-2-butanone-2,4-dinitrophenylhydrazone 

Relevant articles and documents

Products, kinetic regularities, and mechanism of thermal decomposition of ethyl(methyl)dioxirane

The products and kinetic regularities of thermal decomposition of ethyl(methyl)dioxirane (EMD) were studied. The consumption of EMD occurs via four parallel pathways: two isomerizations to ethyl acetate and methyl propionate, solvent oxidation via insertion of the oxygen atom into the C-H bond of a solvent molecule (butanone), and hydrogen atom abstraction from the solvent by dioxirane with radical escape from the cage. The contribution of the latter route to the oxidation of butan-2-one at 35°C is 43%. Alkyl radicals initiate EMD decomposition in an inert atmosphere. The activation parameters of EMD isomerization to esters and the reaction of EMD with butanone were determined. The isomerization of EMD was studied by the DFT method. The geometric parameters were optimized at the UB3LYP level using the 6-31G**and/or 6-311+G**basis sets. The calculated energies were corrected taking into account zero-point vibrations. The theoretical results are in good agreement with experimental data. The mechanism of EMD thermolysis is considered.

N-PEGylated Thiazolium Salt: A Green and Reusable Homogenous Organocatalyst for the Synthesis of Benzoins and Acyloins

N-PEGylated-thiazolium salt is used as efficient catalyst for the benzoin condensation. The catalyst was synthesized by reaction of activated polyethylene glycol 10,000 (PEG-10000) with 4-methyl-5-thiazoleethanol (sulfurol). Reaction mixture undergoes temperature-assisted phase transition and catalyst separated by simple filtration. After reaction course, catalyst can be recycled and reused without any apparent loss of activity which makes this process cost effective and hence ecofriendly. Synthesized benzoins and acyloins by this method have been characterized on the basis of melting point and 1H-NMR spectral studies. Graphic Abstract: [Figure not available: see fulltext.]

carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis

Here we report a new robust nicotinamide dinucleotide phosphate cofactor analog (carba-NADP+) and its acceptance by many enzymes in the class of oxidoreductases. Replacing one ribose oxygen with a methylene group of the natural NADP+ was found to enhance stability dramatically. Decomposition experiments at moderate and high temperatures with the cofactors showed a drastic increase in half-life time at elevated temperatures since it significantly disfavors hydrolysis of the pyridinium-N?glycoside bond. Overall, more than 27 different oxidoreductases were successfully tested, and a thorough analytical characterization and comparison is given. The cofactor carba-NADP+ opens up the field of redox-biocatalysis under harsh conditions.

Sol-gel synthesis of ceria-zirconia-based high-entropy oxides as high-promotion catalysts for the synthesis of 1,2-diketones from aldehyde

Efficient Lewis-acid-catalyzed direct conversion of aldehydes to 1,2-diketones in the liquid phase was enabled by using newly designed and developed ceria–zirconia-based high-entropy oxides (HEOs) as the actual catalysts. The synergistic effect of various cations incorporated in the same oxide structure (framework) was partially responsible for the efficiency of multicationic materials compared to the corresponding single-cation oxide forms. Furthermore, a clear, linear relationship between the Lewis acidity and the catalytic activity of the HEOs was observed. Due to the developed strategy, exclusively diketone-selective, recyclable, versatile heterogeneous catalytic transformation of aldehydes can be realized under mild reaction conditions.

Selective Hydrogenation of Diketones on Supported Transition Metal Catalysts

Abstract: The hydrogenation of α-diketones yields α-hydroxyketones or vic-diols, both compounds of great interest in fine chemistry. The reaction tests were the liquid phase hydrogenation of 2,3-butanedione and 2,3-pentanedione at mild conditions. The objectives of this work were evaluating the effect over the activity and selectivity of: (a) different transition metallic phase based catalysts supported on activated carbon, (b) the symmetry of the reactants and (c) solvents. The physicochemical characterization of the catalysts was carried out by ICP, XRD, TEM, N2 adsorption and XPS. The keto-enol equilibrium of diketones was studied by 1H-NMR. All the catalysts were active in both reactions. In terms of activity, Pt and Rh were the best active phases. For both reactants the highest selectivity towards hydroxyketones were achieved with Pd, while Ru was the most selective towards the diol. Both the activity and selectivity followed similar patterns in the hydrogenation of both diketones. The greater activity of Pt was attributed to the high dispersion of the active metal phase in this catalyst and the high efficiency of Pt for C = O bond reduction. The high selectivity of the Pd catalysts towards the intermediate product was attributed to many effects: (i) a lower interaction of the hydroxyketone with the active site as compared to the diketone, (ii) the easy reducibility of the C = C double bond on Pd, provided by the keto-enol tautomerism of diketones.

Energy- And cost-effective non-sterilized fermentation of 2,3-butanediol by an engineered: Klebsiella pneumoniae OU7 with an anti-microbial contamination system

Microbial contamination is a serious challenge that needs to be overcome for the successful biosynthesis of 2,3-butanediol (2,3-BD). However, traditional strategies such as antibiotic administration or sterilization are costly, have high energy demands, and may increase the risk of antibiotic resistance. Here, we intend to develop a robust strategy to achieve non-sterilized fermentation of 2,3-BD. Briefly, the robust strain can metabolize unconventional chemicals as essential growth nutrients, and therefore, outcompete contaminant microbes that cannot use unconventional chemicals. To this end, Klebsiella pneumoniae OU7, a robust strain, was confirmed to rapidly exploit urea and phosphite (unconventional chemicals) as the primary sources of nitrogen (N) and phosphorus (P), and withstand deliberate contamination in the possibly contaminated systems. Secondly, metabolic engineering, pathogenicity elimination and adaptive laboratory evolution were successively performed, endowing the best strain with an excellent fermentation performance for safe 2,3-BD production. Finally, 84.53 g L-1 of 2,3-BD was synthesized with a productivity of 1.17 g L-1 h-1 and a yield of 0.38 g g-1 under the non-sterilized system. In summary, our technique reduces labor and energy costs and simplifies the fermentation process because sterilization does not need to be performed. Thus, our work will be beneficial for the sustainable synthesis of 2,3-BD. This journal is

Vapor-phase catalytic dehydration of butanediols to unsaturated alcohols over yttria-stabilized zirconia catalysts

Vapor-phase catalytic dehydration of butanediols (BDOs) such as 1,3-, 1,4-, and 2,3-butanediol was investigated over yttria-stabilized tetragonal zirconia (YSZ) catalysts as well as monoclinic zirconia (MZ). BDOs were converted to unsaturated alcohols with some by-products over YSZ and MZ. YSZ is superior to MZ for these reactions in a view point of selective formation of unsaturated alcohols. Calcination temperature of YSZ significantly affected the products selectivity as well as the conversion of BDOs: high selectivity to unsaturated alcohols was obtained over the YSZ calcined at high temperatures over 800 °C. In the conversion of 1,4-butanediol at 325 °C, the highest 3-buten-1-ol selectivity of 75.3% was obtained over the YSZ calcined at 1050 °C, whereas 2,3-butanediol was less reactive than the other BDOs. In the dehydration of 1,3-butanediol at 325 °C, in particular, it was found that a YSZ catalyst with a Y2O3 content of 3.2 wt.% exhibited an excellent stable catalytic activity: the highest selectivity to unsaturated alcohols such as 2-buten-1-ol and 3-buten-2-ol over 98% was obtained at a conversion of 66%. Structures of active sites for the dehydration of 1,3-butanediol were discussed using a crystal model of tetragonal ZrO2 and a probable model structure of active site was proposed. The well-crystalized YSZ inevitably has oxygen defect sites on the most stable surface of tetragonal ZrO2 (101). The defect site, which exposes three cations such as Zr4+ and Y3+, is surrounded by six O2? anions. The selective dehydration of 1,3-butanediol to produce 3-buten-2-ol over the YSZ could be explained by tridentate interactions followed by sequential dehydration: the position-2 hydrogen is firstly abstracted by a basic O2? anion and then the position-1 hydroxyl group is subsequently or simultaneously abstracted by an acidic Y3+ cation. Another OH group at position 3 plays an important role of anchoring 1,3-butanediol to the catalyst surface. Thus, the selective dehydration of 1,3-butanediol could proceed via the speculative base-acid-concerted mechanism.

2,3-Butanediol dehydration catalyzed by silica-supported alkali phosphates

Characterization of acid-base centers and catalytic dehydration of 2,3-butanediol (BDO) was performed over a wide range of silica-supported alkali phosphates (M_P/SiO2; M = Na, K, Cs; M:P = 0.5–3 mol:mol). Selectivity to 1,3-butadiene (BD) and 3-butene-2-ol (3B2OL) formed by elimination correlates with the densities of conjugated acid-base pairs and increases in the order Na ??M+ moieties. Isolated Br?nsted acid centers are probably silica grafted phosphoric acid molecules at low M/P and –PO(OH)2 end groups of oligophosphates at M/P > 1.5. Deactivation rate increases with the increase of M/P ratio in order Na K Cs. Deactivation patterns imply that sites responsible for elimination are active in dehydrative epoxidation. Dehydration of 3B2OL smoothly proceeds to BD, but the catalysts deactivate faster compared to BDO dehydration.

Preparation Method for 2,3-pentanedione

A preparation method for 2,3-pentanedione, including the steps of adding one or both of 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone into water and conducting mixing, and introducing ozone at the temperature of 3-20° C. for a reaction to obtain 2,3-pentanedione. The synthesis process of the present invention uses ozone for oxidizing a mixture containing 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone, acetic acid is used as a cocatalyst, reaction conditions are mild, the operation process is simple, the product yield is high, and the cost is low.

An artificial synthetic pathway for acetoin, 2,3-butanediol, and 2-butanol production from ethanol using cell free multi-enzyme catalysis

Upgrading ethanol to higher order alcohols is desired but difficult using current biotechnological methods. In this study, we designed a completely artificial reaction pathway for upgrading ethanol to acetoin, 2,3-butanediol, and 2-butanol in a cell-free bio-system composed of ethanol dehydrogenase, formolase, 2,3-butanediol dehydrogenase, diol dehydratase, and NADH oxidase. Under optimized conditions, acetoin, 2,3-butanediol, and 2-butanol were produced at 88.78%, 88.28%, and 27.25% of the theoretical yield from 100 mM ethanol, respectively. These results demonstrate that this artificial synthetic pathway is an environmentally-friendly novel approach for upgrading bio-ethanol to acetoin, 2,3-butanediol, and 2-butanol.