In the last few years, concerns about the environmental fate and behavior of synthetic organic chemicals for hygienic use detected in waters have increased. Several of these compounds are used intensively, in large volumes, are persistent, bioactive and exhibit bioaccumulation and endocrine disrupting activity. Some pharmaceuticals, including analgesics, antibiotics, antiepilieptics, β-blockers, blood-lipid regulators and contraceptives also have the potential to determine various physiologic responses in aquatic organisms. Other compounds (natural hormones and several industrial and household chemicals) able to affect organisms in receiving waters are also endocrine disrupting agents. A lack of information still exists regarding the potential impact associated with the occurrence, fate and ecotoxicological effects of endocrine disruptors, including pharmaceuticals and personal care compounds in the environment since few compounds were inventoried or regulated worldwide. In some cases, there are no legal requirements to assess the impact of long-term exposure to low concentration of these chemicals. This may be because important classes of these compounds have not been studied in detail up to now due to the non-availability of suitable instrumental techniques or analytical standards for low concentration levels. Recently, the appearance of sophisticated tests for monitoring environmental contamination has revealed the presence of these types of contaminants at lower levels, down to nanograms per liter. This constitutes an important tool in the development of guidelines to monitor and/or update environmental compliance reports. The current survey aims to combine information from the literature on the environmental occurrence, fate and effects of personal care products and endocrine disrupting agents on the environment; as well as on the treatment options for their removal from wastewaters.

Pharmaceuticals, Personal Care Products and Endocrine Disrupting Agents in the Environment – A Review

Biocatalysis in supercritical fluids, in fluorous solvents, and under solvent-free conditions.

Deracemization of α-Methylbenzylamine Using an Enzyme Obtained by In Vitro Evolution

Despite the large number of elaborate enantioselective syntheses for the preparation of a single enantiomer to achieve industrial and scientific goals, the separation and purification of enantiomers (components of racemic compounds) is also necessary. Hence, we present the most often used thought-provoking modern methods based on momentous recognitions (e.g. spontaneous resolution, induced crystallization, resolution by formation of diastereomers, resolution by formation of non-covalent diastereomers, resolution by diastereomeric salt formation, resolution by diastereomeric complex formation, “half equivalent” methods of resolution, separation by crystallization, separation by distillation, separation by supercritical fluid extraction, resolution with mixtures of resolving agents, resolution with a derivative of the target compound, enantioselective chromatography, resolution by formation of covalent diastereomers, resolution by substrate selective reaction, kinetic resolution without enzymes, kinetic resolution by enzyme catalysis, hydrolytic and redox enzymes, kinetic and thermodynamic control, resolutions combined with 2nd order asymmetric transformations, enrichment of partially resolved mixtures, role of the solvent and methods of optimization in the separation of diastereoisomers, non-linear effects and selected examples of resolution on an industrial scale).

Optical resolution methods

Deracemization of racemic chiral tertiary amines has been achieved by combination of an enantioselective amine oxidase, obtained through directed evolution, and ammonia borane in a one-pot process.

A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines.

Optical Resolution of Racemic Alcohols via Diastereoisomeric Supramolecular Compound Formation with O,O′-Dibenzoyl-(2R,3R)-tartaric Acid

The first in situ diastereomeric salt formation reaction in supercritical carbon dioxide is reported in this paper. The reaction studied was the salt formation between racemic ibuprofen and ( R )-(1)-phenylethylamine, and was combined with supercritical fluid extraction in order to separate the unreacted enantiomers from the formed salts. The effects of pressure, temperature and reaction time were studied in detail. With increasing pressure, the reaction rate and the resolution efficiency at equilibrium increase. With increasing temperature, the optical purity of ibuprofen in the carbon dioxide phase increases, as does the reaction rate.

Diastereomer salt formation of ibuprofen in supercritical carbon dioxide

6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) was resolved in several different solvents by tartaric acid derivatives as the most common acidic resolving agents available in industrial quantities. Strong reaction kinetics and solvent dependence were observed, curiously without solvation. In possession of these findings, an economic resolution process is proposed, which is completed by the incorporation of a racemization step.

Unusual phenomena during the resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ): thermodynamic-kinetic control

Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide

α-Phenylethylamine was resolved by its own derivatives formed with a homologous series of dicarboxylic acids. The structure of the oxalamic acid diastereoisomeric salts was investigated by the single-crystal X-ray diffraction method.

Zoltán Juvancz

Papers

Optical Resolution of Racemic Alcohols via Diastereoisomeric Supramolecular Compound Formation with O,O′-Dibenzoyl-(2R,3R)-tartaric Acid

Diastereomer salt formation of ibuprofen in supercritical carbon dioxide

Unusual phenomena during the resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ): thermodynamic-kinetic control

Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide

Resolution of α-phenylethylamine by its acidic derivatives