A simple method to improve cork powder waste adsorption properties

Research Article pubs.acs.org/journal/ascecg

Cite This: ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX

A Simple Method To Improve Cork Powder Waste Adsorption Properties: Valorization as a New Sustainable Wine Fining Agent Luıś Filipe-Ribeiro,*,†,‡ Fernanda Cosme,‡ and Fernando M. Nunes† †

Chemistry Research Centre - Vila Real (CQ-VR), Food and Wine Chemistry Lab, Department of Chemistry and ‡Department of Biology and Environment, University of Trás-os-Montes and Alto Douro, 5001-801 Vila Real, Portugal

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S Supporting Information *

ABSTRACT: Cork powder, an abundant, natural, and cheap byproduct of the cork stopper industry was explored, either in its natural form or after improvement of their adsorption properties by simple physicochemical treatments, as a new sustainable wine fining agent for removing negative volatile phenols (VPs), responsible for one of the most frequent and widespread aroma defects in red wine known as “Brett character”. Cork adsorptive performance improvement by removal of cork extractives, air removal, and ethanol impregnation allowed us to obtain 41% to 62% of 4ethylphenol (4-EP) and 50% to 53% of 4-ethylguaiacol (4-EG) removal from red wine. Performance of the optimized cork powder on removing the negative sensory phenolic defect and recovery of the positive fruity and floral sensory attributes was not significantly different from activated carbon and chitosan, two of the most efficient treatments currently available. Optimized cork powder can be a good solution for VPs removal without impacting negatively on wine quality and sensory profile and can also be used as a new sustainable enological fining agent. The developed solution for the cork powder waste produced in the cork stopper industry can increase the economic value of this abundant waste and reduce the input of new material in wine production. KEYWORDS: Red wine, 4-Ethylphenol, 4-Ethylguaiacol, Cork powder, Sustainability, Bioadsorbents, Phenolic compounds, Aroma compounds

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In winemaking, fining is the deliberate addition of adsorptive materials followed by settling/precipitation, allowing removal of unwanted compounds or clarification, making the wine stable. World wine production in 2016 was 267 million hectoliters.14 In 2014, 68% of the global wine production corresponded to red wine.15 It is expected that the global beverage fining materials market will increase exponentially until 2025 due to the continuous increase in population and will increase the production of various beverages, including wine.16 Many defects that can appear during winemaking result in quality decrease and consequently commercial value. In the last decades, millions of liters of red wine have become contaminated by the yeast Dekkera/Brettanomyces acquiring an unpleasant off-flavor, named “Brett character”,17 described as “leather”, “horse sweat”, “stable”, and “smoke”. It is a major problem in red wine production as consumers tend to reject it.17 It has been shown that using cork pieces (20 mm × 10 mm × 2 mm) at a dose of 3333 g/hL in a model wine solution was able to remove 39% of 4-EP and 32% of 4-EG.18 Also, cork suberin adsorbed on glass beads was able to remove 49%−67% of 4-EP and 45%−71% of 4-EG, depending on the red wine

INTRODUCTION

Cork, the bark of Quercus suber L. is a natural, renewable, sustainable, and biodegradable raw material,1 representing an abundant and cheap source of raw materials for industry without affecting food and feed supplies.2 Portugal is the major cork producer (185,000 tons) processing about three-quarters of the world’s cork, generating up to 25 wt % of cork dust as byproduct.3 Cork powder (CKP) particles have an inadequate size distribution to be used in the manufacture of agglomerates and are burned to produce energy.4 CKP has been used as a biosorbent for heavy metals5 and organic compounds (pesticides,6 pharmaceuticals,7 polycyclic aromatic hydrocarbons8 ). Pretreatments to improve CKP biosorption performance have been studied, such as washing with solvents,9 soaking in salt, acid, or basic solutions,9 chemical oxidation, and thermal treatment.5,10 A major drawback of CKP is that sorption is dependent on granulometry, as there is no access to the inner cork pores, and so it is sorbed on the external surface. Conversion of CKP into polymeric materials is another way to valorize this waste as a source of suberin components for use as monomers in polymer synthesis, such as polyesters and polyurethanes,11 and conversion into liquid polyols through oxypropylation12 or acid liquefaction13 to be used as macromonomers in polyurethane synthesis. © XXXX American Chemical Society

Received: September 18, 2018 Revised: November 4, 2018 Published: December 3, 2018 A

DOI: 10.1021/acssuschemeng.8b04775 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX

Research Article

ACS Sustainable Chemistry & Engineering

Figure 1. Schematic representation of the optimization process for obtaining a high value competitive fining agent from cork stopper industry waste.

Table 1. Surface Area (SBET), Micropore Volume (Vmicro), Pore Diameter (Dp) as determined from N2 Isotherms at −196 °C and Iodine Number (IN) for Cork Powder Samples* Iodine number (IN, mg of iodine/g) 2

2

3

3

Samples

SBET (m /g)

Smeso (m /g)

Vp (cm /g)

Vmicro (cm /g)

Dp (nm)

Not boiled

Boiled

Impregnated not boiled

CKN CKF CKF75 Olive oil

0.257 ± 0.1a 0.259 ± 0.1a 8.805 ± 2.0b

− − −

− − −

0.006 ± 0.001a 0.005 ± 0.002a 0.011 ± 0.05b

3.55 ± 0.08a 3.57 ± 0.08a 3.56 ± 0.08a

355 ± 3a 367 ± 16b

377 ± 13a 387 ± 11a

407 ± 8a 437 ± 1b 532 ± 8c

281 ± 7

*

Natural cork powder (CKN), dichloromethane and ethanol extractive free cork powder (CKF), and after air removal and ethanol impregnation with a particle size below 75 μm (CKFI75). Smeso (volume of mesopores), Vp (total volume of pores). Within each column, values with the same letter are not significantly different (p < 0.05).

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contamination level.19 Therefore, cork could be a useful natural and sustainable fining agent to deal with the serious and widespread problem of red wine “Brett character”; nevertheless, its efficiency is at present less than desirable as the huge amounts needed suggested by the work of Karbowiak et al.18 make it impracticable for the wine industry. This low adsorption capacity can be due to the restricted accessibility of the inner pores and/or also due to the wine complex matrix with hundreds to thousands of compounds, many of them in higher amounts, that can compete with these two volatile phenols (VPs) for adsorption on the cork surface. If these limitations could be solved, CKP could be a new, cheap, sustainable bioadsorbent to be used in the wine industry to remove the negative “Brett character”. Using the average market values for the competitive fining agents known to be efficient to deal with this problem, activated carbon (AC, 1.50−2.0 US$ /kg) and chitosan (1000 US$/kg)20 when compared to the value of using CKP as fuel (0.30 US$/kg) represents a large valorization of these wastes. This work aims to explore the use of the abundant CKP waste, either in its natural form or after its optimization by simple physical and chemical treatments, as a new cheap and sustainable wine fining agent for removing VPs from wine and its sensory negative “Brett character”. Also, its impact on the wine chemical composition and sensory profiles were evaluated, and its efficiency was compared to that of AC and chitosan.

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RESULTS AND DISCUSSION A simple process was developed (Figure 1) to increase the performance of the natural CKP (CKN). CKN was treated to remove the dichloromethane and ethanol extractives (9.9% of dichloromethane-ethanol extractives, CKF). CKF was sieved to obtain a particle size below 75 μm (29% of the CKF, CKF75). As natural cork material contains significant amounts of air entrapped in its hollow parenchymateous death cellular structure,21 and water has a very small diffusion coefficient in cork,22,19 the air from CKN and CKF was removed, and the cork was impregnated with ethanol by vacuum impregnation by repeated degassing cycles (11 times) of CKP immersed in ethanol (CKNI, CKFI, CKFI75). Physicochemical Characterization of Cork Material. Specific surface area and porosity of CKN, CKF, and CKF75 are shown in Table 1. Isotherms of all CKP are of Type III (Figure S1), belonging to a class of nonporous or macroporous solids.23 Samples presented low SBET, although CKF75 presented an almost 34-fold increase in value compared to CKN and CKF. The volume of micropores was very low, and CKF75 presented a 2-fold increase. These values are in accordance with previous results24 and not in accordance with Domingues et al.25 whose results were obtained by mercury porosimetry, explaining the differences observed. CKN and CKF were mainly composed by particles containing arrays of intact cork cells (Figure 2 and Figure S2), whereas CKF75 was mainly composed of cell fragments (Figure 2 and Figure S2). Results obtained suggest that the surface area is mostly due to the external surface. According to Rosa and Pereira,26 these hexagonal pores (hollow cells) are inaccessible to the molecules of the contact solutions because they seem to be

MATERIALS AND METHODS

Provided in the Supporting Information. B


Research Article


Figure 2. Scanning electron micrographs of natural cork powder (CKN) magnified by (a) 500× and (b) 2000×, of dichloromethane and ethanol extractive free cork powder (CKF) and magnified by (c) 500× and (d) 2000×, and of dichloromethane and ethanol extractive free cork powder with a particle size below 75 μm (CKF75) magnified by 500× (e) and 2000× (f). Figure 3. (a) FTIR spectra of natural cork powder (CKN, black) and dichloromethane and ethanol extractive free cork powder (CKF, red) and cork powder with particle size below 75 μm (CKF75, green). (b) X-ray diffraction patterns of natural cork powder (CKN, black) and dichloromethane and ethanol extractive free cork powder (CKF, red) and cork powder with a particle size below 75 μm (CKF75, green).

closed with air inside, and cork has no available internal porosity. Therefore, only these external macropores are detected. CKP samples were further characterized by FTIR spectroscopy (Figure 3a) and X-ray diffraction analysis (Figure 3b). Table S1 summarizes the assignments of the corresponding FTIR bands, based on previous works.27 The spectra of CKN, CKF, and CKF75 were very similar and consistent with the known cork composition.21,28,29 Results show that the major components of the CKP, namely, suberin, lignin, and polysaccharides, were not changed due to the extraction of CKN with dichloromethane and ethanol, and sieving allowed us to obtain cork particles with similar composition to CKF. The X-ray diffraction pattern of CKP displayed a broad amorphous halo (centered ca. 2θ ≈ 21.2°), typical of amorphous materials (Figure 3b). In the original CKP some small but clear peaks are observed in the spectra that disappeared with the removal of dichloromethane and ethanol extractives. The X-ray diffraction pattern observed was similar to that of suberin films.29 Results are in accordance with the literature, showing that the extraction with dichloromethane and ethanol removed some crystalline materials present in the cork cells.30 For CKFI75, the same X-ray diffraction pattern of CKF was observed; nevertheless, the sample crystallinity was lower (2θ ≈ 21.4°/2θ ≈ 10°; 2.22 vs 2.47, respectively). This

may be due to a lower amount of structured cell wall components in this material as discussed previously for the SEM results; CKF75 seems to be composed of cell fragments (Figure 3b) contrary to CKF where particles containing intact arrays of cork cells are clearly observed. Impact of Cork Powder Optimization on Red Wine Volatile Phenol Removal Performance. For evaluating the effect of the different treatments applied in the VPs adsorption capacity, their adsorption performance was tested in a real wine matrix spiked with two concentrations of VPs representing the average and higher range of VPs usually found in red wines that presented the “Brett character”.14 All materials were applied at 250 g/hL dose (Figure 4 and Table S2). CKN was able to reduce significantly the amount of VPs from spiked wine for both contamination levels (Figure 4 and Table S2), nevertheless with a low efficiency. CKF increased the removal efficiency of the cork material for both VPs and C


Research Article


Figure 4. Removal of 4-EP and 4-EG using natural cork powder (CKN), dichloromethane and ethanol extractive free cork powder (CKF), ethanol impregnated cork powder (CKNI and CKFI), and ethanol impregnated extractive free cork powder with a particle size below 75 μm applied at 250 and 500 g/hL (CKFI75250 and CKFI75500). Medium spiked level (750 μg/L for 4-EP and 150 μg/L for 4-EG) and high spiked level (1500 μg/L for 4-EP and 300 μg/L for 4-EG). Within each figure, columns with different letters are significantly different (p < 0.05).

contamination levels (2.1 and 6.8 times for the medium and high contamination level, Figure 4). Cork impregnation with ethanol increased significantly the VPs removal efficiency for both CKN and CKF (Table S2 and Figure 4). Removal efficiency increased with the wine spiking levels from 36% to 59% and 41% to 69% for 4-EP for CKN and CKF, respectively. The same trend was observed for 4-EG (29%−45% and 40%−50% for CKN and CKF, respectively). The higher improvement of adsorption after ethanol impregnation for CKN than for CKF may be explained by the fact that after extractives removal and drying some of the air present in the cork cells was already eliminated by the treatment. To evaluate the available internal surface area in corks after air removal and ethanol impregnation, a modification of the iodine number (IN) method for ACs was used31 (Table 1). No significant differences for the IN were obtained for CKN and CKF. These values are higher than those reported by Domingues et al.23 This difference can be explained by the much lower particle size of the CKP used in our work. Air removal and ethanol impregnation allowed us to increase significantly the corks modified IN (Table 1). Also, both without and with impregnation, CKF always contained a higher modified IN when compared to CKN, showing that the impregnation process and extractives removal increased the available area of corks. Nevertheless, when this method is applied to cork, it may not only measure the available internal

surface area but also iodine can be consumed by reaction with the double bonds of unsaturated fatty acids present in cork suberin,32 as olive oil treated in the same conditions as cork absorbed iodine. If this also occurs in cork, as the cork material used was obtained from the same initial CKP, the increase in IN either by retention in the pore structure of cork or by reaction with the double bonds implies that these became accessible by air removal and ethanol impregnation. These results confirm that the better removal performance in ethanolimpregnated corks is due to a higher accessibility of the solutes to the cork structure and/or to the cork structural components. Also, the removal of hydrophobic extractives from cork increased its efficiency, suggesting that the extractive removal and the consequent increase in the macromolecular cell wall material, mainly composed by the hydrophobic suberin and lignin,18,33 increased the removal efficiency of the VPs. The cork surface has low polarity and high affinity for nonpolar liquids34 suggesting that the driven force of interaction of VPs with the cork surface is of hydrophobic nature. The decrease in particle size (CKFI75), with the exception of 4-EP for the higher contamination levels, increased significantly but only slightly the removal efficiency for VPs (1.2% for 4-EP and 6.1% to 24% for 4-EG; Table S3 and Figure 4). The increase in the application dose of CKFI75 from 250 g/ hL (CKFI75250) to 500 g/hL (CKFI75500) only increased in average 21% and 33% removal for 4-EP and 4-EG, respectively D


Research Article


Figure 5. (a) Reduction of volatile phenols (VPs) concentration. (b) Reduction of volatile phenols (VPs) headspace abundance (in percentage relative to control wine). (c) Reduction of headspace aroma abundance (in percentage relative to control wine). (d) Relative anthocyanin content. (e) Relative phenolic compounds content. (f) Instrumental color intensity. (g) Score differences for phenolic attribute obtained for VPs spiked wine and after treatment. (h) Score differences for fruity attribute obtained for VPs spiked wine and after treatment. (i) Score differences for floral attribute obtained for VPs spiked wine and after treatment with ACs, chitosan, and cork powder for red wine spiked with 750 μg/L of 4ethylphenol (4-EP) and 150 μg/L of 4-ethylguaiacol (4-EG). Within each figure, columns with different letters are significantly different (p < 0.05). Values presented for activated carbons and chitosan are from refs 39, 40 and 41, 42, respectively.

p < 0.003) between the HAC abundance and the octanol− water partition coefficient (Log P) of the aroma compounds detected (Figure S3 and Table S6), reinforcing that the interaction of the volatile compounds including the VPs with the CKP are of a hydrophobic nature as already observed for the interaction of other molecules with cork.23,35 Application of CKN and CKF did not cause any change in the color intensity (Table S7). The same being observed for the lightness (L*) and redness (a*). CKNI and CKFI decreased in average the color intensity, being only significant for CKFI and CKFI75500. The same was observed for L* and a* (Table S7). Changes for the color intensity were not due to a decrease in the levels of monomeric anthocyanins that overall did not change by the application of all CKP (Table S7), suggesting that the color changes were due to a reduction in the wine polymeric pigments. Levels of phenolic acids overall did not change significantly or were significant but small (Table S7). No changes in catechin levels for all CKP applied were observed. To validate the impact of CKNI and CKFI headspace, VPs reduction on the sensory perception, and quality of wines, CKNI-, CKFI-, and CKFI75-treated wines at the two

(Table S4 and Figure 4), suggesting that probably some VPs are present in wine adsorbed more strongly to other wine components precluding their adsorption on the CKFI75. Impact of Cork Powder Application to “Brett Character” Contaminated Wine: Physicochemical and Sensory Quality. Application of CKN to red wine, with few exceptions (Table S5), did not decrease significantly the total abundance of headspace aroma compounds (HAC) in relation to spiked wine (TF). In contrast, CKF resulted in a significant decrease (21%) in the abundance of HAC (Table S5). Ethanol impregnation of both cork samples increased significantly the decrease observed for the HAC abundance (CKNI 32% and CKFI 37%). The decrease in the particle size of CKF did not differ significantly on the removal of HAC when compared to the nonsieved CKP (Table S5). Duplication in application dose (500 g/hL) of CKFI75 resulted in a significant decrease in HAC abundance by more 29% when compared to the 250 g/hL application dose (Table S5). There was a significant correlation between the decrease in total VPs wine content by the CKP treatments with the reduction of headspace abundance of VPs (4-EP, r = 0.953; 4-EG, r = 0.981). Also there was observed a significant correlation (r = 0.731, n = 14, E


Research Article


average 1.3 times higher). For the higher spiking level, the concentration of 4-EG remaining in the wine, CKP, was close, but higher than the olfactory detection threshold of 4-EG (110 μg/L).17 AC presented the highest decrease in the headspace abundance of both VPs, followed by CKP, where the decrease observed was not significantly different, and last was chitosan (Figure 5b). AC presented a higher decrease in HAC (Figure 5c), with CKP and chitosan being least active. In all materials, the reduction in the headspace abundance of VPs was higher than that observed for the HAC abundance (1.17 for AC; 1.58 for chitosan; 1.33 for CKP). Only AC and CKP showed a significantly different reduction of the anthocyanin content of the treated wines (Figure 5d). AC was the product that changed in a higher extent the wine phenolic composition (phenolic acids and catechin) (20% reduction) when compared with CKP (6.9% reduction, Figure 5e). Although instrumentally, it was possible to determine chromatic differences between the treated wine and control wine (Figure 5f), especially for chitosan and to a lesser extend CKP and ACs; these changes were not perceived by the expert panel. The impact on the negative sensory phenolic attribute reduction obtained with CKFI75 was not significantly different from the other two materials (Figure 5g). Also there was not observed significant differences in the recovery of the fruity and floral attributes for CKFI75 when compared to AC and chitosan (Figure 5h and i). Results can be explained by the fact that although CKFI75 application resulted in a lower decrease in the levels of the negative VPs when compared to ACs, CKFI75 also decreased less the HAC abundance, and overall, the sensory impact of CKFI75 was the same as that observed for ACs. This result is in line with that reported by Schumaker et al.43 were they observed that the VPs sensory threshold in wines is dependent on their concentration but also on the aroma complexity of the wine. Overall results show that the simple method developed in this work for improving the sorption properties of cork was successful and efficient on the removal of VPs from the complex matrix that red wine is. When compared to the other alternatives like AC and chitosan, the optimized CKP presented identical sensory performance. Taking into account the simple method used, the natural origin of CKP, the cheap value of this waste (most of the times free), and the successful and competitive performance in decreasing the negative sensory impact of VPs contaminated wines, one of the most important and widespread aroma defects, it can be explored as a new sustainable, nonallergenic, vegan friendly, and efficient wine fining agent. This solution would decrease the input of other materials for the winemaking process that would be replaced by a waste already generated in this industry for producing cork stoppers and increase its value. This application as far as we know is the first to use CKP as a bioadsorbent in such a complex matrix as wine in an industry where the contact between cork and wine by its application as a wine bottle stopper is traditional and generally well accepted by the consumers. The optimized CKP, due to its improved adsorption properties, has the potential of other uses. When compared to other wine fining agents as for example PVPP, ACs, and bentonite, to name only a few, the different adsorption mechanisms of the optimized CKP driven by hydrophobicity represents an alternative solution to be employed where the other fining agents fail to be efficient. This is the case when dealing with other aroma defects caused by hydrophobic

application doses (250 and 500 g/hL) were subjected to sensory analysis by an expert panel. VPs addition significantly and negatively impacted the aroma profile of the spiked wine (TF, Table S8), increasing the phenolic attribute decreasing the wine fruity and floral attributes.36 Application of all CKP and for the two doses of CKFI75 significantly decreased the negative phenolic attribute compared to TF. For the fruity aroma attribute, application of all CKP also allowed us to recover significantly this attribute in relation to TF. For the floral attribute, only CKFI and CKFI75250 allowed us to increase significantly this sensory attribute in relation to TF. The fruity aroma attribute was significantly higher for CKFI75250 than for all other CKP samples even for CKFI75500 (Table S8), explained by the higher decrease in HAC abundance responsible for the fruity notes for the higher application dose as discussed previously. Application of CKP did not change significantly the acidity and body of the wine, but significant and positive differences were observed for bitterness, astringency, balance, and persistence when compared to TF (Table S8). The spiking of wine resulted in a significant increase in the bitterness and astringency attributes when compared to T0. The observed increase in wine astringency and bitterness by VPs spiking of wine can be explained by the relationship between several aroma compounds and the bitterness of foods also observed for wine.37 The decrease in the astringency and bitterness by application of CKFI and CKFI75250 can be explained by a decrease also observed in the negative phenolic attribute observed for these wines. CKNI application increased astringency in relation to TF, and this can be explained probably by a migration of phenolic compounds from CKNI.38 For persistence, the application of CKP to TF significantly increased the persistence of wine (Table S8). In accordance with the instrumental color intensity, sensory color intensity of the wines treated with CKFI and CKFI75 were significantly lower than TF, with the increase in the application dose (CKFI75500) presenting a significantly lower score than CKFI75250 and CKFI. CKFI75500 also decreased the sensory hue, being in accordance with a significant change in °h and L* values. Considering the results obtained for visual (color), aroma, taste, and tactile/textural descriptors determined by the expert panel, and their validation by the chemical composition of wines obtained after treatment with ethanol impregnated CKP (supported by multiple factor analysis results shown in Supporting Information), wine treated with CKFI75250 resulted in a significant improvement in the sensory profile compared to TF. Comparative Efficiency of Optimized Cork Powder with Other Materials Used To Treat Red Wine “Brett Character”. There are available several treatments14 for “Brett character”, namely, AC39,40 and chitosan.41,42 VPs removal efficiency of these two products were compared to the optimized CKP (CKFI75) at a 250 g/hL application dose (Figure 5a). For 4-EP at both spiking levels, all the tested products, except for chitosan, were able to reduce its levels below their olfactory detection threshold (605 μg/L).14 For the low spiking level, AC was the most efficient in reducing the 4-EP wine levels (1.8 times higher than CKFI75); nevertheless, for the high spiking level, the difference was smaller (1.1 times higher). For 4-EG for the lower spiking level, AC was also the most efficient material (1.6 times higher for CKFI75), and again, for the higher spiking level, the difference was lower (in F


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ACS Sustainable Chemistry & Engineering volatile compounds like 2-methylisoborneol,44 geosmin,45 and oct-1-en-3-one,46 to name only a few aromatic defects that affect wine.

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(9) Mota, D.; Marques, P.; Pereira, C.; Gil, L.; Rosa, M. F. Lead bioremoval by cork residues as biosorbent. In ECOWOOD 2006, 2nd International Conference on Environmentally; Compatible Forest Products, Fernando Pessoa University, Porto, Portugal, 2006; pp 251−264. (10) Chubar, N.; Carvalho, J. R.; Correia, M. J. N. Heavy metals biosorption on cork biomass: Effect of the pre-treatment. Colloids Surf., A 2004, 238, 51−58. (11) Sousa, A.; Gandini, A.; Silvestre, A. J.; Pascoal Neto, C. Synthesis and characterization of novel biopolyesters from suberin and model comonomers. ChemSusChem 2008, 1, 1020−1025. (12) Gandini, A.; Cruz-Pinto, J. J.; Pascoal Neto, C. University of Aveiro. Process for the production of liquid polyols of renewable origin by the liquefaction of agro-forestry and agro-food biomass. WO2010020903, 2010. (13) Soares, B.; Gama, N.; Freire, C.; Barros-Timmons, A.; Brandão, I.; Silva, R.; Neto, C. P.; Ferreira, A. Ecopolyol Production from Industrial Cork Powder via Acid Liquefaction Using Polyhydric Alcohols. ACS Sustainable Chem. Eng. 2014, 2, 846−854. (14) OIV statistical report on world vitiviniculture, 2017. http:// www.oiv.int/public/medias/5479/oiv-en-bilan-2017.pdf (accessed December 2018). (15) Coriolis.‘What does Asia want for dinner? A drink’ − a report from Coriolis for the NZ Government’s Food and Beverages Review, July 2014. (16) Beverage fining agent market- global industry analysis, size, share, growth, trends and forecast 2018−2028. https://www. transparencymarketresearch.com/beverage-fining-agent-market.html (accessed December 2018).. (17) Milheiro, J.; Filipe-Ribeiro, L.; Vilela, A.; Cosme, F.; Nunes, F. M. 4-Ethylphenol, 4-ethylguaiacol and 4-ethylcatechol in red wines: Microbial formation, prevention, remediation and overview of analytical approaches. Crit. Rev. Food Sci. Nutr. 2017, 1. (18) Karbowiak, T.; Mansfield, A. K.; Barrera-García, V. D.; Chassagne, D. Sorption and diffusion properties of volatile phenols into cork. Food Chem. 2010, 122, 1089−1094. (19) Gallardo-Chacón, J. J.; Karbowiak, T. Sorption of 4-ethylphenol and 4-ethylguaiacol by suberin from cork. Food Chem. 2015, 181, 222−226. (20) Water treatment. https://www.drydenaqua.com/files/water/ resources/pdf/price-list/da_pl_wt_eur.pdf; https://scottlab.com/nobrett-inside-100g-016410 (accessed December 2018). (21) Pereira, H. Rationale of cork properties. BioResources 2015, 10 (3), 1−23. (22) Fonseca, A. L.; Brazinha, C.; Pereira, H.; Crespo, J. G.; Teodoro, O. M. N. D. Permeability of cork for water and ethanol. J. Agric. Food Chem. 2013, 61, 9672−9679. (23) Gregg, S. J.; Sing, K. S. W. Adsorption, Surface Area, and Porosity, 2nd ed.; Academic Press: London, 1991; p 303, DOI: 10.1002/bbpc.19820861019. (24) Pintor, A. M. A.; Silvestre-Albero, A. M.; Ferreira, C. I. A.; Pereira, J. P. C.; Vilar, V. J. P.; Botelho, C. M. S.; Rodríguez-Reinoso, F.; Boaventura, R. A. R. Textural and surface characterization of corkbased sorbents for the removal of oil from Water. Ind. Eng. Chem. Res. 2013, 52, 16427−16435. (25) Domingues, V.; Alves, A.; Cabral, M.; Delerue-Matos, C. Sorption behaviour of bifenthrin on cork. J. Chromatogr. A 2005, 1069, 127−132. (26) Rosa, M. E.; Pereira, H. The Effect of Long-Term Treatment at 100-Degrees-C-150-Degrees-C on Structure, Chemical-Composition and Compression Behavior of Cork. Holzforschung 1994, 48, 226− 232. (27) Lopes, M. H.; Barros, A. S.; Pascoal Neto, C.; Rutledge, D. I.; Delgadillo, A. M.; Gil, L. Variability of cork from Portuguese Quercus suber studied by solid-state 13C-NMR and FTIR Spectroscopies. Biopolymers 2001, 62, 268−277. (28) Gil, L.; Moiteiro, C. Ullmann - Encyclopedia of Industrial Chemistry; Wiley-VCH, 2003; Vol. 9, pp 503−522, DOI: 10.1002/ 14356007.f07_f01.

ASSOCIATED CONTENT

* Supporting Information S

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.8b04775. Details of the experimental procedure, statistical analysis, CKP N2 adsorption isotherms, scanning electron micrographs, multiple factorial analysis of aroma sensory and chemical data, mean scores of each attribute after sensory analysis, headspace aroma profile of red wines, chromatic characteristics, monomeric anthocyanin, phenolic acids, and catechin composition of red wines. (PDF)

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AUTHOR INFORMATION

Corresponding Author

*Luiś Filipe-Ribeiro. E-mail: [email protected]. Phone: +351 918624138. Fax: + 351 259350480. ORCID

Luı ́s Filipe-Ribeiro: 0000-0002-6744-4082 Fernando M. Nunes: 0000-0001-5540-318X Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We acknowledge Aveleda S.A. for supplying wine and SAI Enology for providing CKP samples. We appreciate the financial support provided to CQ-VR (PEst-OE/QUI/ UI0616/2014) by FCT and COMPETE.

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REFERENCES

(1) Aroso, I. M.; Araújo, A. R.; Pires, R. A.; Reis, R. L. Cork: current technological developments and future perspectives for this natural, renewable, and sustainable material. ACS Sustainable Chem. Eng. 2017, 5, 11130−11146. (2) Fernando, S.; Adhikari, S.; Chandrapal, C.; Murali, N. Biorefineries: current status, challenges, and future. Energy Fuels 2006, 20, 1727−1737. (3) Godinho, M. H.; Martins, A. F.; Belgacem, M. N.; Gil, L.; Cordeiro, N. M. A. Properties and processing of cork powder filled cellulose derivatives composites. Macromol. Symp. 2001, 169, 223− 228. (4) Gil, L. Cork powder waste: an overview. Biomass Bioenergy 1997, 13, 59−61. (5) Sen, A.; Olivella, A.; Fiol, N.; Miranda, I.; Villaescusa, I.; Pereira, H. Removal of chromium (VI) in aqueous environments using cork and heat-treated cork samples from Quercus cerris and Quercus suber. BioResources 2012, 7, 4843−4857. (6) Domingues, V. F.; Priolo, G.; Alves, A. C.; Cabral, M. F.; Delerue-Matos, C. Adsorption behavior of α-cypermethrin on cork and activated carbon. J. Environ. Sci. Health, Part B 2007, 42, 649− 654. (7) Villaescusa, I.; Fiol, N.; Poch, J.; Bianchi, A.; Bazzicalupi, C. Mechanism of paracetamol removal by vegetable wastes: The contribution of π−π interactions, hydrogen bonding and hydrophobic effect. Desalination 2011, 270, 135−142. (8) Olivella, M. Á .; Jové, P.; Sen, A.; Pereira, H.; Villaescusa, I.; Fiol, N. Sorption performance of Quercus cerris cork with polycyclic aromatic hydrocarbons and toxicity testing. BioResources 2011, 6, 3363−3375. G


Research Article

ACS Sustainable Chemistry & Engineering (29) Garcia, H.; Ferreira, R.; Martins, C.; Sousa, A. F.; Freire, C. S. R.; Silvestre, A. J. D.; Kunz, W.; Rebelo, L.P-N.; Pereira, C. S. Ex Situ Reconstitution of the Plant Biopolyester Suberin as a Film. Biomacromolecules 2014, 15, 1806−1813. (30) Kreger, D. R. X-Ray Diffraction of Stopper Cork. J. Ultrastruct. Res. 1958, 1, 247−258. (31) European Council of Chemical Manufacturer̀s Federations (CEFIC). Test methods for activated carbon; 1986. (32) Sousa, A. F.; Gandini, A.; Silvestre, A. J. D.; Neto, C. P.; CruzPinto, J. J. C.; Eckerman, C.; Holmbom, B. Novel suberin-based biopolyesters: From synthesis to properties. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2281−2291. (33) Gandini, A.; Pascoal Neto, C.; Silvestre, A. J. D. Suberin: A promising renewable resource for novel macromolecular materials. Prog. Polym. Sci. 2006, 31 (10), 878−892. (34) Cordeiro, N.; Neto, C. P.; Gandini, A.; Belgacem, M. N. Characterization of the cork surface by inverse gas chromatography. J. Colloid Interface Sci. 1995, 174, 246−249. (35) Pintor, A. M. A.; Ferreira, C. I. A.; Pereira, J. C.; Silva, P. C.; Vilar, S. P.; Botelho, V. J. P.; Boaventura, C. M. S.; Correia, P. Use of cork powder and granules for the adsorption of pollutants: A review. Water Res. 2012, 46, 3152−3166. (36) Ferreira, V.; San-Juan, F.; Escudero, A.; Culleré, L.; FernándezZurbano, P.; Sáenz-Navajas, M. P.; Cacho, J. Modeling quality of premium Spanish red wines from gas chromatography-olfactometry data. J. Agric. Food Chem. 2009, 57, 7490−7498. (37) Sáenz-Navajas, M.; Campo, E.; Fernández-Zurbano, P.; Valentin, D.; Ferreira, V. An assessment of the effects of wine volatiles on the perception of taste and astringency in wine. Food Chem. 2010, 121, 1139−1149. (38) Santos, S. A. O.; Villaverde, J. J.; Sousa, A. F.; Coelho, J. F. J.; Neto, C. P.; Silvestre, A. D. Phenolic composition and antioxidant activity of industrial cork by-products. Ind. Crops Prod. 2013, 47, 262−269. (39) Filipe-Ribeiro, L.; Milheiro, J.; Matos, C. C.; Cosme, F.; Nunes, F. M. Reduction of 4-ethylphenol and 4-ethylguaiacol in red wine by activated carbons with different physicochemical characteristics: Impact on wine quality. Food Chem. 2017, 229, 242−251. (40) Filipe-Ribeiro, L.; Milheiro, J.; Matos, C. C.; Cosme, F.; Nunes, F. M. Data on changes in red wine phenolic compounds, headspace aroma compounds and sensory profile after treatment of red wines with activated carbons with different physicochemical characteristics. Data in Brief 2017, 12, 188−202. (41) Filipe-Ribeiro, L.; Cosme, F.; Nunes, F. M. Reducing the negative sensory impact of volatile phenols in red wine with different chitosans: Effect of structure on efficiency. Food Chem. 2018, 242, 591−600. (42) Filipe-Ribeiro, L.; Cosme, F.; Nunes, F. M. Data on changes in red wine phenolic compounds, head space aroma compounds and sensory profile after treatment of red wines with chitosans with different structures. Data in Brief 2018, 17, 1201−1217. (43) Schumaker, M. R.; Diako, C.; Castura, J. C.; Edwards, C. G.; Ross, C. F. Influence of wine composition on consumer perception and acceptance of Brettanomyces metabolites using temporal check-allthat-apply methodology. Food Res. Int. 2018, DOI: 10.1016/ j.foodres.2018.09.034. (44) Pinar, A. L.; Ghadiriasli, R.; Darriet, P.; Buettner, A. Unexpected impact of 2-methylisoborneol as off-odour substance in aged wines. Food Chem. 2017, 220, 498−504. (45) Darriet, P.; Pons, M.; Lamy, S.; Dubourdieu, D. Identification and Quantification of Geosmin, an Earthy Odorant Contaminating Wines. J. Agric. Food Chem. 2000, 48, 4835−4838. (46) Callejón, R. M.; Ubeda, C.; Ríos-Reina, R.; Morales, M. L.; Troncoso, A. M. (2015). Recent developments in the analysis of musty odour compounds in water and wine: a review. J. Chromatogr. A 2016, 1428, 72−85.

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A simple method to improve cork powder waste adsorption properties

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