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Effectiveness of treated paper in oil spills cleanup.


Oil is one of the most important resources of energy in the modern industrial world. As long as oil is explored, transported, stored and used it will present the risk of a spillage. Oil spills impose a major problem on the environment (Kingston, 2002). Various processes have been developed to remove oil from contaminated areas, among them mechanical recovery by oil sorbents is one of the most promising approach. This process includes the transfer and the concentration of oil from the contaminated area to some transportable form of temporary storage with the help of oil sorbents (Wei and Mather, 2005). Oil sorbents in use can be classified as either polymers, natural materials, or treated cellulosic materials (Deschamps et al, 2003). Most commonly used commercial sorbents are synthetic sorbents made of polypropylene or polyurethane. They have good hydrophobic and oleophilic properties, but their non-biodegradability is a major disadvantage (Wei et al, 2003). However, in this process most of the used sorbents end up in landfills and incineration, which either produces another source of pollution or increases the oil recovery cost. So, there is an increased interest in promoting environmental responsibility through cleaning. A biodegradable material with excellent absorption properties would be advantageous in this respect. A number of natural sorbents have been studied for use in oil spill cleanup, e.g. cotton (Choi et al, 1993), wool (Radetic et al, 2003), bark (Haussard et al, 2003), kapok (Hori et al, 2000), and rice straw (Sun et al, 2002).

From the chemist's point of view a broad variety of chemical modification reactions of cellulose both at the OH groups and the C atoms are possible, cellulose is not only the most abundant organic polymer but also a very uniform macromolecule consisting of [beta]- (1-4)-linked anhydroglucose repeating units. Like simple alcohol, the hydroxyl groups of cellulose can be esterified by reactions with acids or other acylating agents. The esterification of cellulose by fatty acid has been widely studied and used in several industries of food, textile, film, etc. Derivatization of cellulose can be performed under both heterogeneous and homogeneous reaction systems (Usarat et al, 2012). The esterification of cellulose is the oldest polymer modification reaction known and its relevance has never lost its impact. In the last few decades, long chain cellulose esters have still been prepared by grafting fatty acids and their derivatives onto cellulose, either by surface or bulk reactions, employing various methods (Berlioz et al 2009; Boufi and Belgacem, 2006; Bras et al, 2007; Crepy et al, 2009; Freire et al, 2006; Pasquini et al, 2008; Peydecastaing et al, 2006). These cellulose derivatives, which were elaborated with different substrates and purposes, showed an enhanced hydrophobic character with water contact angles sometimes exceeding 90[degrees]. The recent contribution from Berlioz et al (Berlioz et al 2009) purports to have achieved an efficient gas-phase esterification of the surface of the cellulose nanofibers, but does not provide any convincing evidence related to the proposed structure of the ensuing cellulose palmitate.

Of all the methods available, the only effective ones turned out to be esterification with fatty acid chlorides and transesterification with methyl esters of fatty acids. The only disadvantages of these methods are the cost of the chemicals and the difficulties in scaling up to an industrial process (Hiatt and Rebel, 1971). There are recent reports of the successful utilization of microwave heating in esterification processes (Ginka et al, 2004). Microwave processing of material has been the focus of attention of numerous researchers in recent years. The effectiveness of using microwaves to promote heating, drying, or melting have been demonstrated in laboratories throughout the world, and some processes have become an industrial reality. In addition, microwave radiation has proved to be a highly effective heating source in chemical reactions. Microwaving can accelerate the reaction rate, provide better yields and uniform and selective heating, achieve greater reproducibility of reactions, and help in developing cleaner synthetic routes. There are several studies being carrying out on the esterification of cellulose by the microwave heating method (Antova et al, 2004; Gourson et al, 1999; Joly et al, 2005(a); Joly et al, 2005(b); Loupy et al, 1993; Memmi, et al, 2006; Satge et al, 2004; Satge et al, 2002). Thus, the present study deals with the surface modification of bagasse paper sheet by grafting with long hydrocarbon chain through heterogeneous esterification with fatty acid anhydride. The prepared substrates were then characterized by FTIR, Scanning Electron Microscopy, X-ray photoelectron spectroscopy and contact angle measurements. The adsorption aptitude of the modified substrate toward new and used engine oil was subsequently investigated.



Unbleached Kraft pulp is kindly provided by Idfo Company, Egypt. Stearic, palmitic, and myristic anhydride (Sigma) are used as received. All other chemicals and solvents are of pure analytical grade and used without further purification.


Preparation of paper sheets:

The conventional hand sheets with a basis weight of 60 g/[m.sup.2] were prepared on a Rapid Khoten sheet former following the standard method IS0 5269-2:2004. The pulp drainability was evaluated by measuring the Shopper Riegler degree (SR-ISO 5267-1). Before testing, the hand sheets were conditioned (23 [degrees]C, 50% relative humidity--ISO 187).

Esterification of bagasse paper sheet:

Esterification solution was prepared by addition of acid anhydride to a mixture of 50 mL C[H.sub.2][Cl.sub.2] and 2 mL pyridine under stirring at room temperature for 30 minutes. Esterification of paper sheet was achieved by activating the paper sheet in microwave at 640 Wt for 30 sec and deeping the activated sheet quickly in esterification solution for different times namely 15, 30, and 60 minutes under continuous stirring at room temperature, then, the samples were activated again in microwave at 640 wt for 30 sec and kept in acetone to extract the unreacted acid before drying in oven at 50 [degrees]C for 1 hour.


FTIR analysis:

The FTIR spectra were obtained with a Perkin-Elmer BX II spectrophotometer used in transmission mode with a resolution of 4 cm-1 in the range of 400-4000 [cm.sup.-1].

Contact angle measurements:

Dynamic contact angle measurements were performed using a Dataphysics OCA 20 apparatus. A calibrated droplet of water was deposited on the surface of paper sheet and the evolution of the contact angle within the acquisition time was recorded using a CCD camera with an automatic acquisition of 50 images per second.

X-ray photoelectron spectroscopy (XPS):

X-ray photoelectron spectroscopy (XPS) experiments were carried out using a Kratos Axis Ultra DLD apparatus (Vacuum Generators, UK) equipped with an monochromated aluminum [K.sub.[alpha]] X-ray source (1486.6 eV) and operating at 15 kV under a current of 8 mA. The samples were placed in an ultra-high-vacuum chamber (108 mbar) with electron collection by a hemispherical analyzer at an angle of 90[degrees]. Signal decomposition was determined using Vision 2.2.8 software, and the overall spectrum was shifted to ensure that the C- C/C-H contribution to the C1s signal occurred at 284.6 eV. XPS was performed on the dried untreated, ethanol extracted, esterified sheet with stearic anhydride.

Scanning electron microscopy (SEM):

The surface morphology of non-grafted and, and grafted bagasse paper sheet was analyzed using electron microscope FEI INSPECTS Company, Philips, Holland, environmental scanning without coating.

Adsorption studies:

Approximately 100 ml of oil was placed in 100 ml glass beaker. A pre-weighed adsorbent paper (raw or modified) was placed in the beaker containing oil and a thin wire was used to immerse the paper into the oil (up to 2 cm from the top of the paper). After a specified time (10, 20, 30, 40, 60, 80, 100 and 120 second), the sorbent was then removed from the beaker. The excess unabsorbed oil was drained for five minutes, and the sorbent was weighed.

The oil absorption capacity was determined from the equation:

Cads = W2--W1/W1 g/g


Cads is the oil absorption capacity in mg/g

W1 and W2 are the weights of paper before and after oil sorption, respectively (Wei et al. 2005).


A lot of methods have been proposed for the acylation of cellulose (Samaranayake and Glasser 1993; Liebert et al. 1994; Heinze and Liebert 2001; Grabner et al. 2002; Sealey et al. 1996), and among the different reagent used; acid chloride and acid anhydride are the most applied (Samaranayake and Glasser 1993) in both heterogeneous and homogeneous media. In the present work we adopt the heterogeneous route to carry out the acylation reaction for two reasons, (i) It reduces the cost of the modified substrate, and (ii) It preserves the microporous structure of the fibers, allowing the generation of a high grafting density and, thus, favoring the formation of hydrophobic domains. To determine the optimum reaction, acylation reactions at a constant concentration of stearic anhydride and different time namely 15, 30, and 60 minutes were carried out. The results summarized in Table 1 show that the contact angle reached a plateau at 15 minutes.

The acylation of bagasse paper sheets by fatty acid places a relatively long hydrophobic chain on their surface. This reaction can occur between the fatty acid carboxylic functional group and the alcohol groups of cellulose, the alcohol groups of lignin, and/or the phenolic group of the lignin. Regardless, the fatty acid chain provides a hydrophobic envelope for the bagasse architecture, the increasing of contact angle of water droplet by the grafting demonstrates this envelope.

Contact angle measurements were carried out by depositing water drops on the paper sheets. As expected, before esterfication paper sheet was hydrophilic. The contact angle of water droplet deposited at its surface was 78 and 56[degrees], for untreated and ethanol extracted paper sheet, respectively. The decreasing of contact angle by ethanol extraction may be due to removal of wax and resin and surfactant-like structures (from extractives) from paper sheet which increasing the hydrophilicity of paper sheet (Belgacem and Gandini, 2005). After esterfication, the contact angle formed by a drop of water deposited at the surface of the investigated surfaces increased very significantly and became higher than the symbolic value of 100[degrees]. It is 114, 112, and 125[degrees] for cellulose stearate, palmate, myresate respectively. While it is 110[degrees] for stearate sheet after ethanol extraction. Moreover, the evolution of the contact angle of a drop of water deposited on the surface of paper before and after treatment shows that the penetration and/or the spreading of the liquid was reduced significantly after esterfication. Moreover, no significant difference was observed in the contact angles of samples treated by stearic anhydride during higher esterfication times.


Characterization of modified fibers:

Different techniques were used to characterize the modified fibers. The FT-IR spectra of the unmodified and the modified paper sheet with fatty acids have shown in Fig. 1. The main characteristic peak of bagasse sheet are the stretching and bending vibration of hydrogen bonding OH group 3276 and 1650 cm-1, respectively.

Also the normalised FT-IR spectra of grafted samples showed similar spectra. Focusing on the region between 1000 and 2000 cm-1, the existence of carbonyl absorption band 1739 cm-1 can be observed and assigned to formation of fatty acid modified paper sheet.

XPS Spectra:

The XPS technique is used to investigate the chemistry at the surface of a sample. It is a quantitative technique in the sense that the number of electrons recorded for a given transition is proportional to the number of atoms at the surface.

XPS spectroscopy was also used to characterize ester-modified cellulosic substrates, as shown from Figs. 2 and 3 and Table 2. The full XPS spectra of untreated, ethanol extracted, and treated sheet by stearic anhydride show that, before treatment, they are mainly constituted of carbon (signal at 284 eV) and oxygen atoms (signal at 532 eV) (Fig. 2). Then, the C1s was deconvoluted, in order to quantify the relative abundance of carbon atom types. In theory, pure cellulose exhibits two peaks in its deconvoluted C1s XPS spectra (Belgacem and Gandini, 2005) namely: (i) C-O at 286.7 eV and associated to alcohols and ethers groups. This peak is noted as C2 and corresponds to five carbon atoms (C2-C6 in Scheme 1) and (ii) O-C-O at 288.3 attributed to acetal moieties. This signal corresponds to one carbon atom (C1 in Scheme 1).

The XPS analysis of all materials reveals the presence of four peaks (C1, C2, C3 and C4). Thus, C1s peaks at 285.0, 286.7, 288.3 and 289.0 eV, attributed to C1 (C-H), C2 (C-O), C3 (O-C-O and/or C=O), and C4 (OC=O) respectively. C1 signal corresponds to non-oxidized alkane-type carbon atoms and was already reported for other similar materials (Belgacem and Gandini, 2005; Dorris and Gray, 1978; Gray et al., 1978; Belgacem et al., 1995) and attributed to the impurities associated with the presence of residual lignin, extractive substances and fatty acids. The surface O/C ratio for pure cellulose (theoretical formula) is 0.83. For all samples, these ratios were found to be lower (0.56, 0.60, and 0.51, for untreated, ethanol extracted, and treated sheet by stearic anhydride respectively), as summarized in Table 2. The extraction of sheet sample by ethanol induced an increase of O/C ratio (from 0.56 to 0.60), because of the removal of some aliphatic-type impurities. These results are in agreement with the previous data, particularly the presence of C1 in the deconvoluted XPS spectra (Belgacem and Gandini, 2005; Paquet et al., 2010). The treated paper sheet by stearic anhydride induced an decrease of O/C ratio (from 0.56 to 0.51), due to increasing of carbon % by octadecanoyl group substitution (C[H.sub.3][(C[H.sub.2]).sub.16]CO) which contains eighteen carbon and one oxygen.

In fact, the intensity of C1 increased from about 30.2 to 38.2%, for Treated sheet by stearic anhydride, as expected from the chemical structure of stearic acid, which contains aliphatic sequence. Concerning Ethanol extracted sheet sample, the intensity of C1 decreased from 30.2 to 26.2% (Table 2) due to the removal of some impurities.

Morphological investigation:

Morphological studies of untreated, ethanol extracted, treated by stearic anhydride for 15,30, 60 minute, and ethanol extracted then esterified for 15 min paper sheet were performed by Scanning electron microscopy (Fig. 4) which reveals a clear-cut distinction between the scanning electron micrographs of original paper sheet and treated sheets.





Oil sorption test:

Raw bagasse is a combination of cellulose, lignin, and other minor components. It is a material that absorbs hydrophilic and hydrophobic materials. Pulping of bagasse removes lignin and other non-cellulose components, resulting in a largely cellulosic material called pulp. Cellulose macromolecules are more attracted to hydrophilic than to hydrophobic materials. The hydrophobic parts of the cellulose molecule are mostly covered by the hydroxyl groups extending from the six-member rings of the cellulose polymer chain (Abd El-Aziz et al., 2009).

The grafting of a fatty acid on the surface of bagasse paper sheets builts relatively long hydrophobic chains. This hydrophobic envelope would, be attractive to oil and apparently contributes to the oil absorbing properties of the modified bagasse paper sheet. This implies that the grafted paper sheet would operate effectively as an oil absorbing material.

Figs. 5and 6 show the overall results of the sorption behavior of different sorbents tested. Paper sheets treated by stearic, palmetic, and myrestic anhydride exhibited high capabilities for oil removal (new and used) than unmodified paper. On comparing the adsorption capacity of sorbents to new and used engine oils, Stearyl sequences-grafted paper sheet showed the highest oil sorption capacity for new engine oil followed by myrestyl then palmetyl-modified sheets. While palmetic modified paper sheet showed the highest oil sorption capacity for the used engine oil followed by myrestic then stearic modified paper sheet. The oil sorption values of untreated paper sheet were generally lower compared than those of modified ones. Thus, sheets grafted by stearic and palmetic anhydrides were found the best performing materials for removing of new and used engine oils, respectively.

It should be noted that when bagasse paper sheet was grafted with fatty acids and used as a sorbent for new oil, a sorption capacities of 6.5, 5.8, 5.9 g/g were achieved after about 60, 100, 80 sec for stearic, palmetic, and myrestic anhydrides treatment, respectively when compared with 4.8 g/g after 80 sec for untreated sheet (fig. 7). It is also noticed from (fig. 7) that the sorption capacities of 5.3, 6.0, 5.5 g/g were achieved after about 80, 60, 60 sec for stearic, palmetic, and myrestic anhydrides treatment, respectively.


A heterogeneous solvent exchange acylation treatment for paper sheets with long chain fatty acid anhydride using microwave radiation is described. The acylation of bagasse paper sheet by fatty acid provides them enveloping layers made of long hydrophobic chain introduced into the bagasse architecture. The increasing of contact angle of water droplet by the grafting demonstrates this envelope. The contact-angle value increased from 78[degrees] for unmodified sheet to about 114, 112, and 125[degrees] for stearic, palmetic, and myrestic samples, respectively. Overall, the results suggested that treatment of paper sheet by fatty acids for oil spill cleanup increase the oil adsorption capacity, given their friendliness to the environment. XPS spectra shows that treated paper sheet by stearic anhydride have indeed occurred. Paper sheets treated by stearic, palmatic, and myrestic anhydride exhibited high capabilities for oil removal (new and used) than unmodified paper sheet due to the hydrophopicity gained by the fatty acid treatment. The absorption kinetics was also improved by these treatments.


Article history:

Received 20 March 2014 Received in revised form April 2014 Accepted 20 April 2014 Available online 26May 2014





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(1) Samir Kamel, (2) Mohamed Naceur Belgacem, (1) Mohamed El-Sakhawy, (1) Ahmed El-Gendy, (3) Hany H. Abdel Ghafar

(1) Cellulose and Paper Department, National Research Center, Dokki, Egypt

(2) LGP2, Laboratory of Pulp and Paper Science, 461, rue de la papeterie, BP65, 38402 St-Martin-d'Heres Cedex, France

(3) Water Pollution Depaerment, National Research Center, Dokki, Egypt and Department of Chemistry, Faculty of Science and Arts, Khulais, King Abdulaziz University, Saudi Arabia

Corresponding Author: Samir Kamel, Cellulose and Paper Department, National Research Center, Dokki, Egypt
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Author:Kamel, Samir; Belgacem, Mohamed Naceur; Sakhawy, Mohamed El-; Gendy, Ahmed El-; Ghafar, Hany H. Abde
Publication:Advances in Natural and Applied Sciences
Article Type:Report
Date:May 1, 2014
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