Microwave Irradiation Assistance and Catalyzed Hydrolytic Depolymerization Of Poly(Ethylene Terephthalate) (PET) Waste Bottles
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1 Al- Mustansiriyah J. Sci Vol. 23, No 1, 2012 Microwave Irradiation Assistance and Catalyzed Hydrolytic Depolymerization f Poly(Ethylene Terephthalate) (PET) Waste Bottles Hussain I. Khalaf and mar A. Hasan Polymer Research Unit, College of Science, Al-Mustansiriyah University Received 20/3/2011 Accepted 17/1/2012 الخلاصة من مخلفات القناني البلاستیكیة المستخدمة تحت ( PET )تمت دراسة تفكك البولیمر (بولي اثیلین تیریفثالات ( تاثیر الاشعة المیكرویة وذلك باستخدام میكروویف محلي تم تحویره في مختبراتنا لغرض اجراء التفاعل الكیمیاي ي. بعد غسل و تنظیف القناني البلاستیكیة قطعت الى شراي ح ثم طحنت على شكل مسحوق تم تجزي تھ تم التحلل الكیمیاي ي القاعدي تحت تاثیر الاشعة المیكرویة mm) 2< >)الى احجام مختلفة تراوحت بین ( و استخدام الفحم الحیواني كعامل مساعد لغرض الحصول 10 و % NaH محلول ھیدروكسید الصودیوم ) على المونمرات المكونة للبولیمر( حامض التریفثالیك و االاثلین كلایكول). درست الظروف المثلى للتفاعل مثل زمن التشعیع, تركیز القاعدة, حجم جزیي ات البولیمر, كمیة العامل المساعد, و قوة الاشعة المیكرویة. تم ترسیب حامض التریفثالیك من المحلول القاعدي لایون الحامض المتكون في التحلل القاعدي باضافة حامض الھیدروكلوریك المركز. بینت النتاي ج ان الظروف المثلى للحصول على نسبة انتاج و نقاوة عالیة لحامض ( و 600 واط قوة الاشعة المیكرویة و ( 10 % NaH كانت ) 99% ( و نقاوة ) wt/wt 90 التریفثالك % ) نسبة الفحم الحیواني و زمن 60 دقیقة. 30% ABSTRACT The depolymerization of poly(ethylene terephthalate) (PET) waste bottles was investigated under microwave irradiation. Domestic microwave oven were modified for this purpose. PET bottles was shredded and grinded to < 5 mm particle size and subjected to basic hydrolysis to terephthalic acid (TPA) and ethylene glycol using 10 % NaH under influence of microwave irradiation in presence charcoal as catalyst. The optimum conditions were investigated such as irradiation time, base concentration, particle size, absorber (catalyst) quantity, and microwave irradiation power. High purity of TPA was precipitated from terephthalate ion (formed during the basic hydrolysis) by addition of hydrochloric acid. Results show that the optimum conditions to give higher percentage of TPA was 10 % NaH, 60 min, 600 W power, and 30 %wt/wt charcoal/pet, 90% TPA was obtained. INTRDUCTIN Polymer recycling is very important to reduce the increasing volumes of polymers waste and to generate monomers that can be reused again [1]. Polyethylene terephthalate (PET) is one of the most important thermoplastic polymers, which widely used in many applications such as a textile fibers, films and packing industries. The soft drink bottles is the most important application of PET due to its transparency in blown containers, high mechanical strength for minimum thickness walls, negligible permeability to C 2 gas and relatively low cost. PET produce a significant household and municipal waste, its consumption increased to more than 3,000,000 ons per year at the end of the last century[2]. So a great attention for recycling methods of PET wast bottles was reported recently[3-6]. The hydrolysis of PET in presence of acid and base using suitable solvents has been reported by several 55
2 Microwave irradiation assistance and catalyzed hydrolytic depolymerization of poly(ethylene terephthalate)(pet) waste bottles Hussain and mar researchers[7-10]. The chemical recycling of PET can be also conducted according to the following process: glycolysis, methanolysis, hydrolysis, and aminolysis or ammonolysis to obtain various monomers [11-15]. Recently, there has been growing interest in applying microwave energy to synthetic organic chemistry, sample preparation for analysis, extraction of natural products from plants, waste treatment and polymer synthesis. The reaction involved in these applications is very fast and are completed within a short period of time. Microwave irradiation is well-known technique for heating and drying materials and is employed in many private households and industrial applications [16]. In contrast, in microwave heating the microwave energy is introduce into the chemical reactor remotely and direct access by the energy source to the reaction vessel is obtained. In addition, microwave energy heats the entire sample at once, eliminating "hot spots" and reducing reaction times, all of which result in larger and purer yields. Reactions that would take days with conventional methods can be completed in few minutes in the microwave [17]. In this paper domestic microwave oven was modified to perform the recycling of PET waste bottles. A pure and high yield of terephthalic acid was obtained in relative short time and low coast procedure. MATERIALS AND METHDS Materials: The PET flakes used in all experiments were produced from post consumer PET bottles with number-average molecular weight of 30,000[8]. The post-consumer PET bottles were cut and fed into a rotary grinder (FZ102 micro plant grinding machine) and then different PET particle size (<0.5 - >2 mm) were obtained by several sieves. All chemical used were reagent grade. Melting point were obtained on a Gallenkamp melting point apparatus and infrared spectrum (KBr) recorded on a Shimadzu 8261 PC spectrophotometer. Elemental analysis (C.H.N) was performed on a Perkin 240 C Elemental Analyzer. Microwave Reactor A domestic microwave oven (Showing, Model:MW-GA 38GSC9), multi-mode microwave device with 2.45 GHz frequency (38 L capacity) and rated microwave power 1000 W was purchased from the local market and modified to carryout chemical reaction. The modification included, reflux condenser mounted through hole in the roof of the cavity, a remote IR sensor (Pyrometer) through hole inside of the cavity was inserted for temperature reaction measurement, and magnetic stirrer was fixed down the cavity of the oven. 56
3 Al- Mustansiriyah J. Sci Vol. 23, No 1, 2012 Hydrolytic depolymerization To study the hydrolytic depolymerization a series of reaction experiments were carried out in the modified microwave reactor. These experiments include study the effect of NaH concentration, charcoal quantity (as microwave absorber), reaction time, particle size of PET powder and microwave power effects. General Procedure 3 g PET, 50 ml of aqueous sodium hydroxide solution and appropriate quantity of charcoal were charged in a one necked 100 ml round-bottom flask equipped with reflux condenser and a magnetic stirrer. The reaction was carried out in the modified microwave oven. After the complete of the reaction, the product was washed with hot distilled water. in order to remove all residues. The filtrate was acidified by conc, hydrochloric acid to ph 2.5. A white precipitate of terephthalic acid (TPA) was filtered and dried in 80 C and weighted. Analysis of TPA The carboxylic acid concentration in the solid product was determined by potential titration[18]. A total of 25 ml of DMS was used as the solvent, in which g of solid product was dissolved. The solution was titrated with 0.1 N potassium hydroxide/ethanol solution at room temperature. RESULTS AND DISCUSSINS Hydrolytic depolymerization of PET in alkaline solution was investigated on a modified domestic microwave oven as an effective technique for the chemical recycling of post-consumer PET and recovery of its TPA monomer. Figure 1 display our modifications on domestic microwave oven, these modifications enable us to use the refluxing conditions, continuously stirring of the mixture and temperature monitoring. Moreover, mechanical stirrer and inlet of inert gas (N 2, Ar) could be used. Waste PET were first depolymerized under irradiation microwave effect using sodium hydroxide solution as hydrolytic agent and charcoal as microwave absorber. In the first stage disodium salt of TPA and ethylene glygol were formed. Secondly, the filtrate was acidified with conc. HCl to yield a white precipitate of TPA. 57
4 Microwave irradiation assistance and catalyzed hydrolytic depolymerization of poly(ethylene terephthalate)(pet) waste bottles Hussain and mar Metal outlet s id e h o le fo r in e r t g a s e n tr a n c e o r te m p e r a tu r e m e a s u r e m e n t Figure-1: Modification of a microwave cavity for performing chemical reactions under reflux conditions. H CH 2 CH 2 C C H PET n NaH, MW, Charcoal n NaC CNa + n H CH 2 CH 2 H EG TPA-Na2 Conc. HCl n HC CH + n + + HCH 2 CH 2 H H 2 NaCl TPA White ppt Scheme 1: Hydrolytic depolymerization reaction of PET Characterization The IR spectrum of the TPA product compared with IR spectrum of references sample as shown in figure 2, confirms the purity of the produced TPA. It can be seen that IR spectrum of TPA obtained from depolymerization nearly coincide on IR spectrum of the reference sample. 58
5 Al- Mustansiriyah J. Sci Vol. 23, No 1, 2012 The characteristic bands at cm cm -1 and cm - 1 are related to carboxylic group, carbonyl group and aromatic ring respectively. These results show good agreement with the reference data, indicating that the purity of the product in the mentioned method is acceptable. Elemental analysis (C.H.N.) is also proved the purity of the obtained TPA. All of the element compositions were found to be the same as those of TPA within experimental errors (0.1 % for hydrogen and 0.2 % for carbon). Moreover, the titration for the solid product showed that the acid concentrations of solid product was also close to the value of TPA, 12.1 mmol/g of TPA. These results indicate that TPA was the solid product obtained offer acidification with high purity. Figure -2: FT-IR spectra of TPA Standard (A) and TPA obtained from Hydrolytic depolymerization reaction (B). TPA % Yield calculation The % yield of TPA was calculated using the formula:. TPA yield (%) = x 100. Where wt. TPA: weight of TPA produced from the Hydrolytic depolymerization of PET wt. TPA :weight of TPA (theoretically) that could be obtained from complete depolymerization of PET wt. of TPA was calculated as follow: Wt. of PET used wt TPA in TPA = x no. of repeating units x Mwt of TPA Mwt. of PET Mwt. of PET no. of repeating units = Mwt. of repeating Unit Effect of NaH concentration Different concentration of NaH was used to determine the optimum base concentration that give the highest yield of TPA, 10 % w/v NaH 59
6 Microwave irradiation assistance and catalyzed hydrolytic depolymerization of poly(ethylene terephthalate)(pet) waste bottles Hussain and mar gave the largest yield as shown in fig.6 above that concentration the yield decreased which may be due to the reverse reaction toward the formation of ester TPA % Wt. % of NaH Figure-3: Effect of NaH Concenetration on the TPA % 30 % (wt charcoal/wt PET), 60 min, 3 g PET(< 0.5 mm particle), 400 W Microwave power Reaction time profile The reaction was examined with time by calculating the TPA % formed to determine the optimum time at which the reaction is almost finished. It was found that after 90 min the percentage of TPA is almost constant (80 %), As shown in Fig.4. TPA % Time / min Figure-4: Effect of Time on the TPA % 50 ml NaH 10%, 30 % (wt charcoal/wt PET), 3 g PET(< 0.5 mm particle) 400 W Microwave power. Effect of addition of microwave absorber Since the heating characteristics of microwave are very fast microwave pyrolysis product yield depended on the amount of microwave absorber in the reaction mixture. As shown in Fig. 5., maximum TPA yield was obtained at 30 % wt/wt Charcoal/ PET. It was assumed that as the amount of microwave absorber is small, reactor could not get enough heat to pyrolysis the polymer chain. Conversely, higher amount of 60
7 Al- Mustansiriyah J. Sci Vol. 23, No 1, 2012 microwave absorber might have lead to localized heating of reaction mixture. Nevertheless, temperature at which the pyrolysis takes place also plays an important role in the product yields [17] TPA % [wt. of charcoal/ wt PET] x 100 Figure- 5 : Effect of charcoal on the TPA % in the product mixture 50 ml of 10% NaH, 60 min, 3 g PET(< 0.5 mm particle size), and 400 W Microwave power Particle size effect The particle size effect on the performance of microwave pyrolysis, was also examined. Fig. 4 shows the effect of particle size on the % of TPA in products mixture using different particle sizes,(<0.5 mm) and (< 2 mm), and (> 2 mm )under the microwave power of 400 W. The results indicate high yield of PET with smaller particle size. These results may be due to the large contact area that promotes higher microwave absorption and heat transfer inside the reaction mixture that would accelerate the entire pyrolytic reaction. Therefore, the heating rate, maximal reaction temperature, and mass reduction ratio were all increased. For smaller particle size, the satisfactory microwave power could be lowered. Table 1: Effect of PET particle size distribution on the TPA % in the product mixture, 50 ml of 10% NaH, 60 min, 3 g PET, and 400 watt Microwave power, and 30 % charcoal Particle size distribution %TPA < 0.5mm 76 < 2 mm 59 > 2 mm 43 Effect of microwave power The influences of microwave power on hydrolysis reaction were examined and shown in Fig.6-. A great increase in PET conversion with increasing microwave power was observed. At 200 W, the PET conversion is only 59% after 1 h. However, under the given conditions, when the power was increased to 400 then 600W, the hydrolysis of PET 61
8 Microwave irradiation assistance and catalyzed hydrolytic depolymerization of poly(ethylene terephthalate)(pet) waste bottles Hussain and mar conversion was gradually increased. The best power that we choose for the optimum condition was 400 W to avoid over heating that could be occurred during the reaction. TPA % Microwave Power/ Watt Figure-6: Effect of microwave power on the TPA % 50 ml NaH 10% 60 min, time 3 g PET(< 0.5 mm particle), and 30 % (wt charcoal/wt PET CNCLUSINS In summary it is clear that charcoal behave as an efficient catalyst for the depolymerization of PET in presence of NaH. A great increase in PET conversion and TPA yield was observed when microwave power increase to 600 W and reaction time of 60 min. also the study revealed the possibility of using modified domestic microwave oven for carrying such chemical reaction REFERENCES 1. Scheirs J. (1998) "polymer recycling", J. Wiley & Sons, W. Sussex. 2. A. Bagheri Garmarudi, M. M. Alavi Nikje, M. Haghshenas 2 nd international and IUPAC conference on Green Chemistry, 14-19, September 2008, Russia. 3. Achilias D. S. and G. P. Karayannnids (2004)"chemical recycling of PET as an indicator of sustainable development" water, Air and soil pollution: focus, 4, Karayannidis G. P. and Achilias D. S. (2007) Chemical recycling of poly(ethylene terephthalate), Macromolecular Materials and Engineering, 292(2, , (2007) 5. M. H. Valikli and M. Haghshenas Ford " chemical recycling of poly(ethylene terephthalate) wasters" world Apllied Sciences journal 8(7): ,
9 Al- Mustansiriyah J. Sci Vol. 23, No 1, J. Scheirs " chapter 4: recycling of PET " polymer recycling, Wiley Series in polymer science, J. Wiley & Sons, Sussex Ben-zu wan, chi-yu Kao, and Wu-Hsun Cheng, kinetics of depolymerization of polyethylene terephthalate) in a potassium hydroxide solution, Ind. Eng. Chem. Res. 2001, 40, Toshiaki Yashioka, Masaki ta, and Akitsugu kuwaki, conversion of used poly(ethylene terephthate) bottle into oxalic acid and terephthalic acid by oxygen oxidation in alkaline solutions at elevated temperatures Ind. Eng. Chem. Res. 2003, 42, Yoshioka T.; kayama N.; kuwaki A. "kinetics of hydrolysis of PET powders in nitric acid by a modified shrinking-core model" Ind Eng. Chem. Res. 1998, 37, Yoshioka T.; Motoki T. kuwaki A. " kinetics of hydrolysis of poly(ethylene terephthalate) powder in sulfuric acid by a modified shrinking-core model" Ind Eng. Chem. Res. 2001, 40, Genta M., T. Iwaya, M. Sasaki and M. Goto, 2007" super critical methanol for polyethylene terephthalate depolymerization" observation using simu;ator, wast management, 27, Genta M., M. and K. Mossaddegh, 2005"depolymerization of poly(ethylene terephthalate) fiber waste using ethylene glycol" polymer degradation and stability, 90: Dayang Ratnasari Abu Baker, Ishak Ahmed, Anita Ramli, "chemical recycling of PET waste from soft drink bottles to produce a thermosetting polyester resin" malysian journal of chemistry, 2006, vol. 8, Np. 1, Minoru, Fumitoshi Yano, Yuichi Kondo, Wataru Matsubara Setsuo omoto, Development of chemical recycling process for post consumer PET bottles by methanolysis in super critical methanol, technical review Vol. 40 extra No. 1 (2003) N.. Pingale and S. R. Shukla " microwave assisted ecofriendly recycling of poly(ethylene terphthalate) bottles waste" European polymer journal, Vol. 44, (2008) A. Loupy (ed.) microwave in organic synthesis Wiley-VCH, Vol. 1, Domínguez A., Fernández Y., Fidalgo B., Pis J.J., Menéndez J.A. (2007) Biogas to syngas by microwave-assisted dry reforming in the presence of char. Energy & Fuels, 21,
10 Microwave irradiation assistance and catalyzed hydrolytic depolymerization of poly(ethylene terephthalate)(pet) waste bottles Hussain and mar 18. Companelli J. R., Kamal M. R. and Cooper D. G. ; A kinetic study of the hydrolytic depolymerization of polyethylene terephthalate at high temperature, J. Appl. Polymer Sci. 1933,
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