60057-62-7Relevant academic research and scientific papers
Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: A facile, efficient and atom economy protocol
Singh, Kishanpal,Sohal, Harvinder Singh,Singh, Baljit
, p. 839 - 845 (2021/04/09)
In present work, the formation of α-hydroxycarboxylic acids have been described from various aromatic aldehydes and ketones via direct electrocarboxylation method with 80-92% of yield without any side product and can be purified by simple recrystallization using sacrificial Mg anode and Pt cathode in an undivided cell, CO2at (1 atm) was continuously bubbled in the cell throughout the reaction using tetrapropylammonium chloride as a supporting electrolyte in acetonitrile. The synthesized compounds obtained in fair to excellent yield with a high level of purity. The characterization of electrocarboxylated compounds was done with spectroscopic techniques like IR, NMR (1H & 13C), mass and elemental analysis.
Abiotic degradation and environmental toxicity of ibuprofen: Roles of mineral particles and solar radiation
Rubasinghege, Gayan,Gurung, Rubi,Rijal, Hom,Maldonado-Torres, Sabino,Chan, Andrew,Acharya, Shishir,Rogelj, Snezna,Piyasena, Menake
, p. 22 - 32 (2017/12/26)
The growing medical and personal needs of human populations have escalated release of pharmaceuticals and personal care products into our natural environment. This work investigates abiotic degradation pathways of a particular PPCP, ibuprofen, in the presence of a major mineral component of soil (kaolinite clay), as well as the health effects of the primary compound and its degradation products. Results from these studies showed that the rate and extent of ibuprofen degradation is greatly influenced by the presence of clay particles and solar radiation. In the absence of solar radiation, the dominant reaction mechanism was observed to be the adsorption of ibuprofen onto clay surface where surface silanol groups play a key role. In contrast, under solar radiation and in the presence of clay particles, ibuprofen breaks down to several fractions. The decay rates were at least 6-fold higher for irradiated samples compared to those of dark conditions. Toxicity of primary ibuprofen and its secondary residues were tested on three microorganisms: Bacillus megaterium, Pseudoaltermonas atlantica; and algae from the Chlorella genus. The results from the biological assays show that primary PPCP is more toxic than the mixture of secondary products. Overall, however, biological assays carried out using only 4-acetylbenzoic acid, the most abundant secondary product, show a higher toxic effect on algae compared to its parent compound.
Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds
Lesieur, Mathieu,Genicot, Christophe,Pasau, Patrick
supporting information, p. 1987 - 1990 (2018/04/16)
A continuous mesofluidic process has been developed for benzylic C-H oxidation with moderate to good yields using a photocatalyst (riboflavin tetraacetate, RFT) activated by a UV lamp and an iron additive [Fe(ClO4)2] via incorporation of singlet oxygen (1O2) for the direct formation of oxidized C=O or CH-OH compounds.
Degradation of ibuprofen by hydrodynamic cavitation: Reaction pathways and effect of operational parameters
Musmarra, Dino,Prisciandaro, Marina,Capocelli, Mauro,Karatza, Despina,Iovino, Pasquale,Canzano, Silvana,Lancia, Amedeo
, p. 76 - 83 (2015/09/28)
Ibuprofen (IBP) is an anti-inflammatory drug whose residues can be found worldwide in natural water bodies resulting in harmful effects to aquatic species even at low concentrations. This paper deals with the degradation of IBP in water by hydrodynamic cavitation in a convergent-divergent nozzle. Over 60% of ibuprofen was degraded in 60 min with an electrical energy per order (EEO) of 10.77 kWh m-3 at an initial concentration of 200 μg L-1 and a relative inlet pressure pin = 0.35 MPa. Five intermediates generated from different hydroxylation reactions were identified; the potential mechanisms of degradation were sketched and discussed. The reaction pathways recognized are in line with the relevant literature, both experimental and theoretical. By varying the pressure upstream the constriction, different degradation rates were observed. This effect was discussed according to a numerical simulation of the hydroxyl radical production identifying a clear correspondence between the maximum kinetic constant kOH and the maximum calculated OH production. Furthermore, in the investigated experimental conditions, the pH parameter was found not to affect the extent of degradation; this peculiar feature agrees with a recently published kinetic insight and has been explained in the light of the intermediates of the different reaction pathways.
Highly efficient C-H hydroxylation of carbonyl compounds with oxygen under mild conditions
Liang, Yu-Feng,Jiao, Ning
, p. 548 - 552 (2014/01/23)
A transition-metal-free Cs2CO3-catalyzed α-hydroxylation of carbonyl compounds with O2 as the oxygen source is described. This reaction provides an efficient approach to tertiary α-hydroxycarbonyl compounds, which are highly valued chemicals and widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very environmentally friendly and practical. This transformation is highly efficient and highly selective for tertiary C(sp3)-H bond cleavage. OH, so simple! A transition-metal-free Cs2CO 3-catalyzed α-hydroxylation of carbonyl compounds with O 2 provided a variety of tertiary α-hydroxycarbonyl compounds (see scheme; DMSO=dimethyl sulfoxide), which are widely used in the chemical and pharmaceutical industry. The simple conditions and the use of molecular oxygen as both the oxidant and the oxygen source make this protocol very efficient and practical.
Silicon nanowires as photoelectrodes for carbon dioxide fixation
Liu, Rui,Yuan, Guangbi,Joe, Candice L.,Lightburn, Thomas E.,Tan, Kian L.,Wang, Dunwei
supporting information; experimental part, p. 6709 - 6712 (2012/09/22)
Lights on: When illuminated, p-type Si nanowires donate photogenerated electrons to aromatic ketones, producing reactive radicals that can harvest CO2 to yield α-hydroxy acids (see scheme). The reaction scheme closely resembles that of natural photosynthesis and gives up to 98 % yield and selectivity. Products obtained by this reaction include important precursors for nonsteroidal anti-inflammatory drugs, such as ibuprofen and naproxen. Copyright
Facile one-pot preparation of 2-arylpropionic and arylacetic acids from cyanohydrins by treatment with aqueous HI
Aramini, Andrea,Sablone, Manolo R.,Bianchini, Gianluca,Amore, Alessia,Fanì, Michela,Perrone, Plinio,Dolce, Alberto,Allegretti, Marcello
experimental part, p. 2015 - 2021 (2009/07/04)
A novel one-pot two-step procedure has been developed to synthesize highly substituted 2-arylpropionic and arylacetic acids, by treatment with aqueous HI, from cyanohydrins. The hydrogenolytic reduction of α-hydroxy-2-arylpropionic acids was the key step of the process and the optimization of the reaction conditions led to identify aqueous HI as an appropriate and selective reagent for the reductive deoxygenation of cyanohydrins. The synthetic route described a general and efficient strategy for the preparation of large libraries of phenylacetic and phenylpropionic acids derivatives.
On the enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates by lipases
Bellezza, Francesca,Cipiciani, Antonio,Ricci, Giacomo,Ruzziconi, Renzo
, p. 8005 - 8012 (2007/10/03)
The enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates was performed using lipases from Candida rugosa and Candida cylindracea (OF-360). A careful analysis of the reaction products revealed that racemic 2-hydroxy-2- arylpropionic acid and traces of 2-arylacrylic acid are formed, in addition to the expected 2-aryl-2-fluoropropionic acid. The presence of powerful electron-releasing groups in the aromatic ring of the substrate increase the amount of 2-hydroxypropionic acid. A mechanistic hypothesis has been formulated according to which the enzyme facilitates the elimination of fluoride ion from the hydrolysed acid with the formation of an α-carboxy-stabilized carbocation which provides 2-hydroxypropionic acids by nucleophilic attack of H2O and 2-arylacrylic acids by a β-elimination process.
Electrochemical synthesis of precursors of non-steroidal anti-inflammatory agents
Damodar,Raju, R. Ramesh,Reddy, S. Jayarama
, p. 2655 - 2658 (2007/10/03)
A simple and high yield procedure has been developed for the electrochemical synthesis of 2-hydroxy-(p-isobutylphenyl)propanoic acid and 2-hydroxy-2-(6-methoxynaphthyl)propanoic acid from p-isobutylacetophenone and 2-acetyl-6-methoxynaphthalene respective
