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Acetylation of Nata De Coco (Bacterial Cellulose) and Membrane Formation

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Acetylation of Nata De Coco (Bacterial Cellulose) and Membrane Formation MATEC Web of Conferences 268, 04003 (2019) https://doi.org/10.1051/matecconf/201926804003 RSCE 2018 Acetylation of Nata de coco (bacterial cellulose) and membrane formation Erika Louise Alberto1, Ailey Nicole de Ocampo1, Christopere Ghil Depasupil1, Mayzonee Ligaray2, Ramon Christian Eusebio3, Aileen Orbecido1, Arnel Beltran1,*, and Liza Patacsil2,* 1Department of Chemical Engineering, Gokongwei College of Engineering, De La Salle University, 2401 Taft Avenue, Manila 1004, Philippines 2Malayan Colleges Laguna, Pulo Diezmo Road, Cabuyao City, Laguna 4025, Philippines 3Department of Chemical Engineering, College of Engineering and Agro-Industrial Technology, University of the Philippines Los Baños, College, Laguna 4031, Philippines Abstract. Nata de coco (NDC), a bacterial cellulose formed by Acetobacter xylinum, was utilized to fabricate a membrane via acetylation and phase inversion methods. The NDC was activated and dissolved in N,N-Dimethylacetamide (DMAc) with lithium chloride (LiCl) at varying amounts of NDC, LiCl/DMAc ratio, activation temperature, and dissolution temperature. Acetylation was done by adding acetic anhydride (in a mass ratio of 1:12 NDC-anhydride) to NDC-DMAc/LiCl solution at a dissolution temperature of 110 °C for 3 hours. The modified-NDC was recovered via precipitation in methanol. The modified-NDC was washed with deionized water then freeze-dried. Modification was verified by determining the degree of substitution (DS) using titration and FTIR analysis. It was observed that the modification could be carried out at an NDC/DMAc (w/v) ratio of 1:75 at 120 °C for 1 hour, and addition of 8% (w/v) LiCl catalyst at 110 °C for 20 minutes. The DS of the modified-NDC was observed in the range of 2.84 – 3.69, which indicates a successful modification. This was further verified by the FTIR results. Membrane fabrication was carried out using the modified-NDC via immersion-precipitation and solvent evaporation methods. A successful membrane formation was observed using solvent evaporation. 1 Introduction anhydride. Ramos et al. [2] conducted the acetylation at 110 °C for 4 hours with varying acetic anhydride Nata de coco (NDC), a bacterial cellulose (BC), is a volume. They reported a DS ranged of 0.28-2.8. At popular gelatinous delicacy in most Southeast Asian higher acetic anhydride volume, the DS also increased countries produced via fermentation of coconut milk the production of polysubstituted derivatives of assisted by a bacterium belonging to the genus cellulose. Ass [3] acetylated sisal and linter cellulose at Acetobacter. Although it is generally consumed as food, 110 °C for 4 hours and 1 hour, respectively. The reported there has been a significant interest to NDC among the DS was 1.3 for sisal and 1.4-1.5 for linter cellulose. scientific community due to its purity and physio- Lastly, El Seoud et al. [4] acetylated plant cellulosic mechanical properties. materials at 60 °C for 18 hours. The acetic anhydride Investigation on the potential of BC as a polymer volume was also varied, thus resulting to a wide range of composite greatly emerged in the recent years. In a DS acquired. The reported values ranged from 1.5 to 4.5. study by Lima et al. [1] , acetylation of bacterial These studies show that degree of acetylation increases cellulose was performed in the BC dissolve N,N- with increasing anhydride concentration and increasing dimethylacetamide/ Lithium chloride (DMAc/LiCl) ionic acetylation time. solvent system. The degree of substitution (DS) was As far as membrane fabrication is concerned, Dang examined at various cellulose-acetic anhydride ratios of et al. [5] synthesized forward osmosis (FO) composite 1:50, 1:12, and 1:60. Furthermore, the reaction membranes from Acetobacter xylinum modified by temperature was also varied. It was determined that the sodium alginate and cross-linked with calcium chloride. acetylation procedure done with 1:12 ratio at 110 °C The study showed that the modified BC sheet material would give the highest yield. The result of the degree of was suitable as FO membrane as the salt rejection was substitution for this system was 2.61. However, it was relatively high (98.57%). However, it has lower water reported that the bacterial cellulose has lost its flux (4.80 LMH) compared to 9.283 LMH of the pristine crystallinity, becoming amorphous. BC membrane. There are other studies that dealt with the acetylation In this study, cellulose acetate (CA) from NDC was of dissolved cellulose in DMAc/LiCl system using acetic synthesized through homogeneous acetylation. The * Corresponding authors: [email protected] , [email protected] © The Authors, published by EDP Sciences. This is an open access article distributed under the terms of the Creative Commons Attribution License 4.0 (http://creativecommons.org/licenses/by/4.0/). MATEC Web of Conferences 268, 04003 (2019) https://doi.org/10.1051/matecconf/201926804003 RSCE 2018 effect of activation temperature, NDC/DMAc ratio, LiCl system was reheated to 110 °C under nitrogen flow and concertation, and dissolution temperature were observed. in a reflux condensing system. Acetic anhydride was The DS was determined using titration, and the presence then added to the mixture in NDC-to-anhydride of acetyl groups in the acetylated NDC was verified via proportion of 1:12 (w/v). The mixture was stirred at 110 FTIR analysis. The acetylated NDC was then utilized in °C for 3 hours. The system was cooled to room membrane fabrication via immersion-precipitation temperature. The resulting solution was dispersed in method and solvent evaporation method. methanol to precipitate the acetylated NDC. The precipitates formed were filtered and were repeatedly washed with deionized water to remove any traces of 2 Materials and methods DMAc, LiCl and other chemicals. Finally, the precipitates were freeze-dried for 2 days and ground into 2.1. Materials and reagents fine powders. NDC was purchased from Malvar, Batangas (Philippines). DMAc (≥ 99%) was purchased from 2.5 Characterization Sigma-Aldrich Co. (USA). LiCl (≥ 99%) was obtained The degree of substitution (DS) was determined from LOBA Chemie (India). Nitrogen (high purity) was using titration method [7] One gram of dried acetylated purchased from Linde Philippines, Inc. (Philippines). NDC was transferred to a 250 mL Erlenmeyer flask then Acetic anhydride and dichloromethane (DCM; ≥ 99.9%) 40mL of 75% ethanol was added. The flask was loosely were obtained from Ajax Finechem (Australia). stoppered and was heated to 55 ºC for 1 hour. The same Hydrochloric acid (HCl; 37%) and methanol (≥ 99.9%) procedure was also done for 1 g dried NDC (blank). were obtained from RCI Labscan (Thailand). Acetone (≥ After heating, the flask was tightly stoppered and 99.5%) was obtained from Tedia Company Inc. (USA). allowed to stand at room temperature for about 72 hours. Sodium hydroxide pellets (NaOH; AR Grade) and The solutions were titrated with 0.5 M HCl until potassium bromide (KBr; AR Grade) were obtained phenolphthalein end point. Afterwards, 1 mL of 0.5 M from UNIVAR (USA). Silicon Oil was obtained from HCl was added as excess and NaOH was allowed to QuintStar Petrol Chemical Services (Singapore). diffuse overnight. The disappearance of the faint pink color indicated complete neutralization. The small 2.2 Pretreatment of Nata de coco excess of HCl was then back titrated with 0.5 M NaOH solution to phenolphthalein end point. Percent acetyl The NDC was soaked in 1% w/v NaOH solution and was content (% Ac) and DS were determined using equations washed with distilled water until the pH of the material (1) and (2), respectively. became neutral. Afterwards, NDC was shred in a wet blender and was placed in a glass pan for drying in a VHCl ,b − VHCl ,s NHCl + VNaOH ,s − VNaOH ,b NNaOH %Ac = × 4.305 (1) rapid drying oven at 60 °C for 6 hours. It was kept in a ms 162×%Ac dry container at room temperature for storage. DS = 4305 − 43×%Ac (2) 2.3 Dissolution of Nata de coco where, VNaOH,s/b is the amount of required for titration of the sample and blank, respectively, in mL; N is the Procedures by El Seoud et al. [4] and Lima et al. [1] NaOH normality of NaOH; VHCl,s/b is the amount of HCl were adopted for the dissolution of NDC. A mixture of required for titration of the sample and blank, dried powdered NDC and DMAc with mass to volume respectively, in mL; NHCl is the normality of HCl; and, ratio ranged from 1:50 to 1:85 was agitated. To activate m is the weight of the sample in g. the dissolution, the mixture was heated to 120, 150, and s Nicolet 6700 Fourier-transform Infrared (FTIR) 170 °C in an oil bath for 1 hour in a condensing system spectrometer was utilized to determine the chemical under nitrogen. Then the mixture was cooled to 110 °C. functional groups of the unmodified dried NDC and Five to 8% (w/v) LiCl was added to the mixture. The acetylated NDC. The sample mixed with KBr was temperature at 110 °C was maintained for 20 minutes. analyzed over a frequency range of 4000 to 500 cm-1. The mixture was continuously stirred at room temperature for 12 hours. Complete dissolution is achieved when there is no powdered NDC that can be 2.6 Membrane fabrication via phase inversion visibly detected in the solution and increase in viscosity method becomes evident. 2.6.1 Immersion-precipitation method 2.4 Acetylation of Nata de coco The immersion-precipitation method [8] was employed The acetylation of dissolved NDC followed the for the fabrication CA membranes. First, CA in acetone technique of El Seoud et al. Error! Reference source solution in varying dope concent rations of 1% and 2% not found.and Lima et al.
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