Efficient Synthesis of 2-Ethylhexanoic Acid via N-Hydroxyphthalimide Catalyzed Oxidation of 2-Ethylhexanal with Oxygen.

An efficient method for the synthesis of 2-ethylhexanoic acid has been reported. The method involves the 2-ethylhexanal oxidation using oxygen or air in the presence of N-hydroxyphthalimide in isobutanol as a solvent under mild conditions. A high selectivity of >99% for 2-ethylhexanoic acid was achieved. The influence of catalyst amount, solvent type and quantity, temperature, and reaction time on the product composition was studied. The developed method is in line with the global trends aimed at developing green oxidation processes as well as having potential for implementation in industry due to its high selectivity, cost-effective oxidizing agent, and mild reaction conditions. The use of isobutanol as a solvent is of crucial importance providing an opportunity for potential producers of 2-EHAL from butanal to employ the less valuable alcohol.

Structure-activity relationship read-across and transcriptomics for branched carboxylic acids.

The purpose of this study was to use chemical similarity evaluations, transcriptional profiling, in vitro toxicokinetic data, and physiologically based pharmacokinetic (PBPK) models to support read-across for a series of branched carboxylic acids using valproic acid (VPA), a known developmental toxicant, as a comparator. The chemicals included 2-propylpentanoic acid (VPA), 2-ethylbutanoic acid, 2-ethylhexanoic acid (EHA), 2-methylnonanoic acid, 2-hexyldecanoic acid, 2-propylnonanoic acid (PNA), dipentyl acetic acid or 2-pentylheptanoic acid, octanoic acid (a straight chain alkyl acid), and 2-ethylhexanol. Transcriptomics was evaluated in 4 cell types (A549, HepG2, MCF7, and iCell cardiomyocytes) 6 h after exposure to 3 concentrations of the compounds, using the L1000 platform. The transcriptional profiling data indicate that 2- or 3-carbon alkyl substituents at the alpha position of the carboxylic acid (EHA and PNA) elicit a transcriptional profile similar to the one elicited by VPA. The transcriptional profile is different for the other chemicals tested, which provides support for limiting read-across from VPA to much shorter and longer acids. Molecular docking models for histone deacetylases, the putative target of VPA, provide a possible mechanistic explanation for the activity cliff elucidated by transcriptomics. In vitro toxicokinetic data were utilized in a PBPK model to estimate internal dosimetry. The PBPK modeling data show that as the branched chain increases, predicted plasma Cmax decreases. This work demonstrates how transcriptomics and other mode of action-based methods can improve read-across.

Ligand-assisted structure tailoring of highly luminescent Cu-In-Zn-S/ZnS//ZnS quantum dots for bright and stable light-emitting diodes.

Harnessing environment-friendly and low-cost multinary Cu-In-Zn-S quantum dots (QDs) as emitters for light-emitting diodes (LEDs) has attracted great attention for display and lighting application. However, suboptimal QD structure is a huge obstacle, which results in serious non-radiative recombination and efficiency roll-off. Herein, we synthesized structure-tailored Cu-In-Zn-S/ZnS//ZnS QDs by improving the reactivity of shell growth by 2-ethylhexanoic acid (EHA) ligands. The EHA-assisted shell growth can boost an extended alloyed layer at the core-shell interface and a smoothed confinement barrier, which effectively passivate the interface defects and suppress Förster resonance energy transfer (FRET) process. These synthesized QDs display a bright photoluminescence emission (quantum yield of 83%) and a larger size of 8.4 nm. Moreover, the resulting LEDs based on the EHA-assisted QDs exhibit a maximum luminance of 8074 cd/m2, and a current efficiency of 7.3 cd/A with a low efficiency roll-off. Our results highlight a remarkable ligand strategy to tailor the QD structure for high performance QD-based LEDs.

Fetal origin of endocrine dysfunction in the adult: the phthalate model.

Di-(2-ethylhexyl) phthalate (DEHP) is a plasticizer with endocrine disrupting properties that is found ubiquitously in the environment as well as in human amniotic fluid, umbilical cord blood, human milk, semen, and saliva. It is used in the industry to add flexibility to polyvinyl chloride-derived plastics and its wide spread use and presence has resulted in constant human exposure through fetal development and postnatal life. Epidemiological studies have suggested an association between phthalate exposures and human reproductive effects in infant and adult populations. The effects of fetal exposure to phthalates on the male reproductive system were unequivocally shown on animal models, principally rodents, in which short term deleterious reproductive effects are well established. By contrast, information on the long term effects of DEHP in utero exposure on gonadal function are scarce, while its potential effects on other organs are just starting to emerge. The present review focuses on these novel findings, which suggest that DEHP exerts more complex and broader disruptive effects on the endocrine system and metabolism than previously thought. This article is part of a Special Issue entitled "CSR 2013".