ISEP - Departamento de Engenharia Química
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- Characterization of Active Sites on Carbon CatalystsPublication . Figueiredo, José L.; Pereira, Manuel F. R.; Freitas, Maria M. A.; Órfão, José J. M.A method based on the deconvolution of TPD spectra is proposed for the characterization of surface oxygen groups, which can act as the active sites on carbon catalysts. The method, which was previously used to characterize activated carbons oxidized in the gas phase, has been extended and applied to other materials, carbons oxidized in the liquid phase. It is shown that this method fits quite well the TPD experimental data of the original activated carbon as well as the gas-phase and liquid-phase oxidized materials and is suitable to estimate the amounts of each type of oxygen surface groups.
- Microalgae for biodiesel production and other applications: A reviewPublication . Mata, Teresa M.; Martins, António A.; Caetano, Nídia SáSustainable production of renewable energy is being hotly debated globally since it is increasingly understood that first generation biofuels, primarily produced from food crops and mostly oil seeds are limited in their ability to achieve targets for biofuel production, climate change mitigation and economic growth. These concerns have increased the interest in developing second generation biofuels produced from non-food feedstocks such as microalgae, which potentially offer greatest opportunities in the longer term. This paper reviews the current status of microalgae use for biodiesel production, including their cultivation, harvesting, and processing. The microalgae species most used for biodiesel production are presented and their main advantages described in comparison with other available biodiesel feedstocks. The various aspects associated with the design of microalgae production units are described, giving an overview of the current state of development of algae cultivation systems (photo-bioreactors and open ponds). Other potential applications and products from microalgae are also presented such as for biological sequestration of CO2, wastewater treatment, in human health, as food additive, and for aquaculture.
- Selective recovery of chromium, copper, nickel, and zinc from an acid solution using an environmentally friendly processPublication . Machado, Manuela D.; Soares, Eduardo V.; Soares, Helena M.V.M.Purpose Real electroplating effluents contain multiple metals. An important point related with the feasibility of the bioremediation process is linked with the strategy to recover selectively metals. In this work, a multimetal solution, obtained after microwave acid digestion of the ashes resulted from the incineration of Saccharomyces cerevisiae contaminated biomass, was used to recover selectively chromium, copper, nickel, and zinc. Results The acid solution contained 3.8, 0.4, 2.8, and 0.2 g/L of chromium(III), copper, nickel, and zinc, respectively. The strategy developed consisted of recovering copper (97.6%), as a metal, by electrolyzing the solution at a controlled potential. Then, the simultaneous alkalinization of the solution (pH 14), addition of H2O2, and heating of the solution led to a complete oxidation of chromium and nickel recovery (87.9% as a precipitate of nickel hydroxide). After adjusting the pH of the remaining solution at pH 10, selective recovery of zinc (82.7% as zinc hydroxide) and chromium (95.4% as a solution of cromate) was achieved. Conclusion The approach, used in the present work, allowed a selective and efficient recovery of chromium, copper, nickel, and zinc from an acid solution using a combined electrochemical and chemical process. The strategy proposed can be used for the selective recovery of metals present in an acid digestion solution, which resulted from the incineration of ashes of biomass used in the treatment of heavy metals rich industrial effluents.
- Lipophilic Caffeic and Ferulic Acid Derivatives Presenting Cytotoxicity against Human Breast Cancer CellsPublication . Serafim, Teresa L.; Carvalho, Filipa S.; Marques, Maria P. M.; Calheiros, Rita; Silva, Tiago; Garrido, J.M.P.J.; Milhazes, Nuno; Borges, Fernanda; Roleira, Fernanda; Silva, Elisário T.; Holy, Jon; Oliveira, Paulo J.In the present work, lipophilic caffeic and ferulic acid derivatives were synthesized, and their cytotoxicity on cultured breast cancer cells was compared. A total of six compounds were initially evaluated: caffeic acid (CA), hexyl caffeate (HC), caffeoylhexylamide (HCA), ferulic acid (FA), hexyl ferulate (HF), and feruloylhexylamide (HFA). Cell proliferation, cell cycle progression, and apoptotic signaling were investigated in three human breast cancer cell lines, including estrogen-sensitive (MCF-7) and insensitive (MDA-MB-231 and HS578T). Furthermore, direct mitochondrial effects of parent and modified compounds were investigated by using isolated liver mitochondria. The results indicated that although the parent compounds presented no cytotoxicity, the new compounds inhibited cell proliferation and induced cell cycle alterations and cell death, with a predominant effect on MCF-7 cells. Interestingly, cell cyle data indicates that effects on nontumor BJ fibroblasts were predominantly cytostatic and not cytotoxic. The parent compounds and derivatives also promoted direct alterations on hepatic mitochondrial bioenergetics, although the most unexpected and never before reported one was that FA induces the mitochondrial permeability transition. The results show that the new caffeic and ferulic acid lipophilic derivatives show increased cytotoxicity toward human breast cancer cell lines, although the magnitude and type of effects appear to be dependent on the cell type. Mitochondrial data had no direct correspondence with effects on intact cells suggesting that this organelle may not be a critical component of the cellular effects observed. The data provide a rational approach to the design of effective cytotoxic lipophilic hydroxycinnamic derivatives that in the future could be profitably applied for chemopreventive and/or chemotherapeutic purposes.
- Impact of fluorides on the removal of heavy metals from an electroplating effluent using a flocculent brewer’s yeast strain of Saccharomyces cerevisiaePublication . Machado, Manuela D.; Soares, Eduardo V.; Soares, Helena M.V.M.Besides several toxic heavy metals, electroplating effluents can have in solution different cations and anions, which may influence heavy metals removal by the biomass. Among them, fluorides are commonly used in the electroplating industries and thus can be found in the respective wastewaters. In the present work, the effect of the presence of fluorides in the efficiency of chromium(III), copper(II) and nickel(II) removal, from an effluent, by heat-inactivated cells of a brewing flocculent strain of Saccharomyces cerevisiae was evaluated. The presence of fluorides severely decreased (460%) the removal of chromium(III) by yeast biomass. This effect impaired the effective treatment of the effluent according to the US Environmental Protection Agency and the Portuguese law; conversely, a higher removal of copper(II) and nickel(II) was observed. This behaviour can be understood by metal speciation. In the presence of fluorides, chromium(III) was mainly complexed, becoming unavailable for yeast accumulation; this effect decreased the efficiency of chromium(III) removal. Thus, in the presence of fluorides, less chromium(III) is associated with biomass and consequently more yeast binding sites remain available for the uptake of other metals present in solution. This fact explains the increase of copper(II) and nickel(II) removal in the presence of fluorides.
- Enhanced host–guest electrochemical recognition of herbicide MCPA using a b-cyclodextrin carbon nanotube sensorPublication . Rahemi, V.; Vandamme, J.J.; Garrido, J.M.P.J.; Borges, F.; Brett, C.M.A.; Garrido, E.M.P.J.An electrochemical sensor for the determination of the chlorophenoxy herbicide MCPA has been developed, based on a combination of multi-walled carbon nanotubes with incorporated b-cyclodextrin and a polyaniline film modified glassy carbon electrode. The proposed molecular host–guest recogni-tion based sensor has a high electrochemical sensitivity for the determination of MCPA. The electrochemical behaviour of MCPA at the chemically modified electrode was investigated in detail by cyclic voltammetry. The results indicate that the b-CD/MWCNT modified glassy carbon electrode exhibits efficient electrocatalytic oxidation of MCPA with high sensitivity, stability and lifetime. The analytical characteristics of this film were used for the quantitative determination of MCPA in natural waters. Cyclic voltammetry in phosphate buffer solution at pH 6.0, allowed the development of a method to determine MCPA, without any previous steps of extraction, clean-up, or derivatization, in the range of 10–100 mmol L-1, with a detection limit of 0.99 mmol L-1 in water. The results were statistically compared with those obtained through an established high-performance liquid chromato-graphy technique, no significant differences having been found between the two methods.
- Electrochemical determination of the herbicide bentazone using a carbon nanotube b-Cyclodextrin modified electrodePublication . Rahemi, V.; Garrido, Jorge; Borges, Fernanda; Oliveira-Brett, A. M.; Garrido, E. ManuelaAn electrochemical sensor has been developed for the determination of the herbicide bentazone, based on a GC electrode modified by a combination of multiwalled carbon nanotubes (MWCNT) with b-cyclodextrin (b-CD) incorporated in a polyaniline film. The results indicate that the b-CD/MWCNT modified GC electrode exhibits efficient electrocatalytic oxidation of bentazone with high sensitivity and stability. A cyclic voltammetric method to determine bentazone in phosphate buffer solution at pH 6.0, was developed, without any previous extraction, clean-up, or derivatization steps, in the range of 10–80 mmolL 1, with a detection limit of 1.6 mmolL 1 in water. The results were compared with those obtained by an established HPLC technique. No statistically significant differences being found between both methods.
- Host-Guest interaction between herbicide oxadiargyl and hydroxypropyl-β-cyclodextrinPublication . Benfeito, Sofia; Rodrigues, Tiago; Garrido, Jorge; Borges, Fernanda; Garrido, E. ManuelaIn the face of a growing human population and increased urbanization, the demand for pesticides will simply rise. Farmers must escalate yields on increasingly fewer farm acres. However, the risks of pesticides, whether real or perceived, may force changes in the way these chemicals are used. Scientists are working toward pest control plans that are environmentally sound, effective, and profitable. In this context the development of new pesticide formulations which may improve application effectiveness, safety, handling, and storage can be pointed out as a solution. As a contribution to the area, the microencapsulation of the herbicide oxadiargyl (OXA) in (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) was performed. The study was conducted in different aqueous media (ultrapure water and in different pH buffer solutions). In all cases an increment of the oxadiargyl solubility as a function of the HP-β-CD concentration that has been related to the formation of an inclusion complex was verified. UV-Vis and NMR experiments allowed concluding that the stoichiometry of the OXA/HP-β-CD complex formed is 1 : 1. The gathered results can be regarded as an important step for its removal from industrial effluents and/or to increase the stabilizing action, encapsulation, and adsorption in water treatment plants.
- Wine and grape polyphenols — a chemical perspectivePublication . Garrido, Jorge; Borges, FernandaPhenolic compounds constitute a diverse group of secondary metabolites which are present in both grapes and wine. The phenolic content and composition of grape processed products (wine) are greatly influenced by the technological practice to which grapes are exposed. During the handling and maturation of the grapes several chemical changes may occur with the appearance of new compounds and/or disappearance of others, and consequent modification of the characteristic ratios of the total phenolic content as well as of their qualitative and quantitative profile. The non-volatile phenolic qualitative composition of grapes and wines, the biosynthetic relationships between these compounds, and the most relevant chemical changes occurring during processing and storage will be highlighted in this review.
- Hydroxycinnamic acid antioxidants: an electrochemical overviewPublication . Teixeira, José; Gaspar, Alexandra; Garrido, E. Manuela; Garrido, Jorge; Borges, FernandaHydroxycinnamic acids (such as ferulic, caffeic, sinapic, and p-coumaric acids) are a group of compounds highly abundant in food that may account for about one-third of the phenolic compounds in our diet. Hydroxycinnamic acids have gained an increasing interest in health because they are known to be potent antioxidants. These compounds have been described as chain-breaking antioxidants acting through radical scavenging activity, that is related to their hydrogen or electron donating capacity and to the ability to delocalize/stabilize the resulting phenoxyl radical within their structure.The free radical scavenger ability of antioxidants can be predicted from standard one-electron potentials. Thus, voltammetric methods have often been applied to characterize a diversity of natural and synthetic antioxidants essentially to get an insight into their mechanism and also as an important tool for the rational design of new and potent antioxidants.The structure-property-activity relationships (SPARs) correlations already established for this type of compounds suggest that redox potentials could be considered a good measure of antioxidant activity and an accurate guideline on the drug discovery and development process. Due to its magnitude in the antioxidant field, the electrochemistry of hydroxycinnamic acid-based antioxidants is reviewed highlighting the structure-property-activity relationships (SPARs) obtained so far.