Farklı dioktil tereftalat (DOTP) sentez reaksiyonları ve DOTP ile plastikleştirilmiş PVC'nin özellikleri üzerine kısa derleme

Year 2022, Volume: 28 Issue: 7, 1001 - 1013, 30.12.2022

Aycan Altun Mehmet Ferdi Fellah

Abstract

PVC, yaygın olarak tercih edilen termoplastiklerden biridir. Plastikleştirici katkı maddeleri veya plastikleştiriciler, PVC'de dipol bağlar arası etkileşimi kırmak ve genel olarak PVC'yi yumuşatmak için kullanılmaktadır. Plastikleştiricilerin elektrik konektörleri, vinil zemin kaplamaları, vinil su tutucuları, oyuncaklar, şişe kapakları, medikal cihazlar gibi pek çok uygulaması bulunmaktadır. Plastikleştiricilerin büyük çoğunluğunu çevreye zararlı ftalatlar oluştursa da, Dioctyl tereftalat (DOTP), ftalat içermeyen bir plastikleştirici olarak bilinir. Endüstride tercih edilen plastikleştiricilerden biri olan DOTP, aromatik bir tereftalattır. DOTP'nin doğrudan esterleştirme ve transesterleşme olmak üzere iki ana üretim yöntemi bulunmaktadır. Bu derlemede, DOTP plastikleştiricinin farklı sentez reaksiyonları özetlenmiştir. Literatürde, çalışmalar genellikle farklı katalizör, çözücü, reaktan oranları ve sıcaklık, basınç, reaksiyon süresi gibi reaksiyon koşullarına odaklanmaktadır. Atık PET ürünlerinden DOTP sentezlemek çevre dostu bir üretim yöntemidir. Ayrıca, başlıca migrasyon, mekanik ve termal özellikleri olmak üzere DOTP ile plastikleştirilmiş PVC'nin özellikleri ele alınmıştır. Sonuçlara göre, DOTP, PVC ile yüksek uyumluluğa sahiptir ve DOTP ile Plastikleştirilmiş PVC iyi migrasyon, mekanik ve termal özellikler sergilemektedir. DOTP, iyi özelliklere, düşük üretim maliyetine ve düşük toksisiteye sahip olmasından dolayı gelecek vaat eden bir plastikleştiricidir.

Keywords

DOTP, Esterleşme, Transesterleşme, PVC, Mekanik özellikler, Termal özellikler

A mini-review on different synthesis reactions of dioctyl terephthalate (DOTP) and properties of DOTP plasticized PVC

Abstract

PVC is one of the commonly preferred thermoplastics. Plasticizing additives or plasticizers are added to break interstrand-dipole interaction in PVC and soften PVC in general. Plasticizers have many applications such as electrical connectors, vinyl floorings, vinyl water stops, toys, bottle caps, and medical devices. Although a great majority of plasticizers are phthalates that harm to environment, Dioctyl terephthalate (DOTP) is known as a non-phthalate plasticizer. DOTP, one of the plasticizers preferred in the industry, is an aromatic terephthalate. There are two main production methods of DOTP; direct esterification and transesterification. In this review, different synthesis reactions of DOTP plasticizer were summarized. Studies have generally focused on different catalysts, solvents, reactant ratios, and reaction conditions such as temperature, pressure, and reaction time in literature. Synthesizing DOTP from scrap PET products is an environmentally friendly manufacturing method. Besides, properties of DOTP plasticized PVC, mainly migration, mechanical and thermal properties, have been reviewed. According to the results, DOTP has high compatibility with PVC, and DOTP plasticized PVC shows good migration, mechanical and thermal properties. DOTP is a promising plasticizer due to having good properties, low production cost, and low toxicity.

Keywords

DOTP, Esterification, Transesterification, PVC, Mechanical properties, Thermal properties

References

• [1] Ji LN. “Study on preparation process and properties of polyethylene terephthalate (PET)”. Applied Mechanics and Materials, 312, 406-410, 2013.
• [2] Langer E, Was̈kiewicz S, Lenartowicz-Klik M, Bortel K. “Application of waste poly(ethylene terephthalate) in the synthesis of new oligomeric plasticizers”. Polymer Degradation and Stability, 119(21), 105-112, 2015.
• [3] Şimşek B, Uygunoğlu T, Korucu H, Kocakerim MM. “Analysis of the effects of dioctyl terephthalate obtained from polyethylene terephthalate wastes on concrete mortar: A response surface methodology based desirability function approach application”. Journal of Cleaner Production, 170, 437-445, 2018.
• [4] Chen J, Lv J, Ji Y, Ding J, Yang X, Zou M, Xing L. “Alcoholysis of PET to produce dioctyl terephthalate by isooctyl alcohol with ionic liquid as cosolvent”. Polymer Degradation and Stability, 107, 178-183, 2014.
• [5] Tan J, Liu B, Fu Q, Wang L, Xin J, Zhu X. “Role of the oxethyl unit in the structure of vegetable oil-based plasticizer for PVC: An effcient strategy to enhance compatibility and plasticization”. Polymers, 11(5), 1-15, 2019.
• [6] Tüzüm Demir AP, Ulutan S. “Migration of phthalate and non-phthalate plasticizers out of plasticized PVC films into air”. Journal of Applied Polymer Science, 128(3), 1948-1961, 2013.
• [7] Erythropel HC, Shipley S, Börmann A, Nicell JA, Maric M, Leask RL. “Designing green plasticizers: Influence of molecule geometry and alkyl chain length on the plasticizing effectiveness of diester plasticizers in PVC blends”. Polymer, 89, 18-27, 2016.
• [8] Chen J, Liu Z, Nie X, Zhou Y, Jiang J, Murray RE. “Plasticizers derived from cardanol: synthesis and plasticization properties for polyvinyl chloride(PVC)”. Journal of Polymer Research, 25(5), 1-14, 2018.
• [9] Tian F, Zhang KT, Ni YR, Su CH. "Study on the formula of the environmental friendly 90 °C PVC sheathing compound". Advanced Materials Research, 518-523, 828-832, 2012.
• [10] Moulay S. “Chemical modification of poly(vinyl chloride)- Still on the run”. Progress in Polymer Science, 35(3), 303-331, 2010.
• [11] Li M, Li S, Xia J, Ding C, Wang M, Xu L, Yang X, Huang K. “Tung oil based plasticizer and auxiliary stabilizer for poly(vinyl chloride)”. Materials and Design, 122(5), 366-375, 2017.
• [12] Saling P. “Sustainability management in strategic decision-making processes”. uwf UmweltWirtschaftsForum|Sustainability Management Forum, 25(3), 169-176, 2017.
• [13] Chen J, Li X, Wang Y, Li K, Huang J, Jiang J, Nie X. “Synthesis and application of a novel environmental plasticizer based on cardanol for poly(vinyl chloride)”. Journal of the Taiwan Institute of Chemical Engineers, 65(8), 488-497, 2016.
• [14] Bee ST, Mok WR, Lee TS, Tee TT, Issabayeva G, Rahmat AR. “Evaluation performance of multiple plasticizer systems on the physicomechanical, crystallinity and thermogravimetry of polyvinyl chloride”. Journal of Polymer Engineering, 34(6), 521-529, 2014.
• [15] Hahladakis JN, Velis CA, Weber R, Iacovidou E, Purnell P. “An overview of chemical additives present in plastics: Migration, release, fate and environmental impact during their use, disposal and recycling”. Journal of Hazardous Materials, 344(2), 179-199, 2018.
• [16] Fu Q, Long Y, Gao Y, Ling Y, Qian H, Wang F, Zhu X. “Synthesis and properties of castor oil based plasticizers”. RSC Advances, 9(18), 10049-10057, 2019.
• [17] Nalli S, Cooper DG, Nicell JA. “Biodegradation of plasticizers by Rhodococcus rhodochrous”. Biodegradation, 13(5), 343-352, 2002.
• [18] Chen J, Liu Z, Li K, Huang J, Nie X, Zhou Y. “Synthesis and application of a natural plasticizer based on cardanol for poly(vinyl chloride)”. Journal of Applied Polymer Science, 132(35), 1-9, 2015.
• [19] Daniels PH. “A brief overview of theories of PVC plasticization and methods used to evaluate PVCplasticizer interaction”. Journal of Vinyl and Additive Technology, 15(4), 219-223, 2009.
• [20] Schilling CL, Kelly KK. “Plasticizers which improve compatibility in pvc formulations”. Patent and Trademark Office, Washington DC, U.S. Patent, 0105673 A1, 2018.
• [21] Tan J, Zhang S, Lu T, Li R, Zhong T, Zhu X. “Design and synthesis of ethoxylated esters derived from waste frying oil as anti-ultraviolet and efficient primary plasticizers for poly(vinyl chloride)”. Journal of Cleaner Production, 229(8), 1274-1282, 2019.
• [22] Coltro L, Pitta JB, Madaleno E. “Performance evaluation of new plasticizers for stretch PVC films”. Polymer Testing, 32(2), 272-278, 2013.
• [23] Barber ED, Fox JA, Giordano CJ. “Hydrolysis, absorption and metabolism of di(2-ethylhexyl) terephthalate in the rat”. Xenobiotica, 24(5), 441-450, 1994.
• [24] Zhang H, Zhu F, Fu Q, Zhang X, Zhu X. “Mechanical properties of renewable plasticizer based on ricinoleic acid for PVC”. Polymer Testing, 76(7), 199-206, 2019.
• [25] Nagorka R, Conrad A, Scheller C, Süßenbach B, Moriske HJ. “Diisononyl 1,2-cyclohexanedicarboxylic acid (DINCH) and Di(2-ethylhexyl) terephthalate (DEHT) in indoor dust samples: Concentration and analytical problems”. International Journal of Hygiene and Environmental Health, 214(1), 26-35, 2011.
• [26] Harmon JP, Otter R. “Green Chemistry and the Search for New Plasticizers”. ACS Sustainable Chemistry and Engineering, 6(2), 2078-2085, 2018.
• [27] Jose B, Ryu JH, Kim YJ, Kim H, Kang YS, Lee SD, Kim HS. “Effect of plasticizers on the formation of silver nanoparticles in polymer electrolyte membranes for olefin/paraffin separation”. Chemistry of Materials, 14(5), 2134-2139, 2002.
• [28] Salloum HAl, Saunier J, Barakat H, Yagoubi N. “Impact of the nature and concentration of plasticizers on the ability of PVC to sorb drug”. International Journal of Pharmaceutics, 496(2), 664-675, 2015.
• [29] “ELAFLEKS®-DOTP (Dioctyl Terephthalate)-Ela Kimya Kimyevi Maddeler.” https://www.elakimya.com.tr/en/productgroups/elafleks-dotp-dioctyl-terephthalate/ (25.08.2019).
• [30] Krauskopf LG. “How about alternatives to phthalate plasticizers?”. Journal of Vinyl and Additive Technology, 9(4), 159-171, 2003.
• [31] Gimeno P, Thomas S, Bousquet C, Maggio AF, Civade C, Brenier C, Bonnet PA. “Identification and quantification of 14 phthalates and 5 non-phthalate plasticizers in PVC medical devices by GC-MS”. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 949-950, 99-108, 2014.
• [32] Cook SL, Tomlin CF, Turner PW. “Production of di-(2- ethylhexyl) terephthalate”. Patent and Trademark Office, Washington DC, U.S. Patent, 7276621, 2007.
• [33] Osborne VH, Turner PW, Cook SL. “Production of terephthalic acid di-esters”. Patent and Trademark Office, Washington DC, U.S, Patent. 7799942, 2010.
• [34] Zeng C. "Study on esterification rule in DOTP preparation". Journal of Nanjing University of Chemical Technology, 4, 69-72, 1994.
• [35] Du K, Lian ML, Fan ZF, Li Y. "Preparation of Terephthalic Acid (TPA) and Dioctyl Terephthalate (DOTP) by Anthracite’s Alkali Oxygen Oxidation". Applied Mechanics and Materials, 541-542, 95-99, 2014.
• [36] Hua P, Sha ZL, Li JH. "Purification of Terephthalate from Waste Material and Preparation of Dioctyl Terephthalate". Journal of Nantong Institute of Technology (Natural Science), 3, 533-553, 2004.
• [37] Liao TC, Jen JC, Lin HM. “Dioctyl Terephthalate Plasticizer and Method of Enhancing Reaction Efficiency in Process for Producing the Same”. Patent and Trademark Office, Washington DC, U.S. Patent, 20180362440, 2019.
• [38] Li K, Jiang, J, Nie X, Xu Y. "Pressure effect on the esterification of DOTP". Guangdong Chemical Industry, 14, 39-46, 2013.
• [39] Xinpeng L, Tianxiang W. "Reaction kinetics of esterification of synthetic dioctyl terephthalate with nonacid catalyst". Journal of Chemical Engineering of Chinese Universities, 2, 1-7, 1994.
• [40] Wei JG, Liu DZ, Sun PQ, Sun SH. "Mechanism and Kinetics of Diisooctyl Terephthalate Synthesis". Journal of Chemical Engineering of Chinese Universities, 20(4), 665-668, 2006.
• [41] Firdovsi ST, Yagoub M, Parvin AE. “Transesterification reaction of dimethyl terephthalate by 2-ethylhexanol in the presence of heterogeneous catalysts under solventfree condition”. Chinese Journal of Chemistry, 25(2), 246-249, 2007.
• [42] Dupont LA, Gupta VP. “Degradative transesterification of terephthalate polyesters to obtain DOTP plasticizer for flexible PVC”. Journal of Vinyl and Additive Technology, 15(2), 100-104, 1993.
• [43] Thavornsetawat T, Chuayjuljit S, Pimpan V. "Synthesis of plasticizer for PVC from terephthalic acid based on chemical recycling of post-consumer PET bottles". Journal of scientific research Chulalongkorn University, 27(1), 1-8, 2001.
• [44] Zuoyun H, Yuanfan X, Dongfan R, Xing L. "A new process of preparing plasticizer dotp from waste pet". Speciality Petrochemicals, 3, 1-6, 1997.
• [45] Shuyong J, Zhanlin X, Yurong R, Xiaoyu C, Qingyong Y. "Study on synthesis of dioctyl terephthalate from waste terylene catalyzed by solid super-acid". Speciality Petrochemicals, 6, 1-5, 2004.
• [46] Zhang RH, Wu HF. "Study on production of dioctyl terephthalate from waste sensitive film". Shaanxi Chemical Industry, 34(5), 311-312, 2005.
• [47] Wang L, Tao HX. "Study on the Synthesis of DOTP catalysized by SnO2-ZnO composit oxide". Jilin Normal University Journal (Natural Science Edition), 2, 71-72, 2006.
• [48] Shi X, Jiang P, Lu Y, Hu J, Wang H. "Synthesis of dioctyl terephthalate by waste polyethylene terephthalate". Chemical Industry and Engineering Progress, 27(1), 143-146, 2008.
• [49] Liu S, Zhou L, Li L, Yu S, Liu F, Xie C, Song Z. “Isooctanol alcoholysis of waste polyethylene terephthalate in acidic ionic liquid”. Journal of Polymer Research, 20(12), 1-6, 2013.
• [50] Liu F, Chen J, Li Z, Ni P, Ji Y, Meng Q. “Alcoholysis of poly(ethylene terephthalate) to produce dioctyl terephthalate with sub- and super-critical isooctyl alcohol”. Journal of Analytical and Applied Pyrolysis, 99, 16-22, 2013.
• [51] Zhou L, Lu X, Ju B, Yao H, Xu J, Zhou Q, Hu Y, Zhang S. “Alcoholysis of polyethylene terephthalate to produce dioctyl terephthalate using choline chloride-based deep eutectic solvents as efficient catalysts”. Green Chemistry, 21(4), 897-906, 2019.
• [52] Zhao Y, Mishra P, Han F, Liu X, Shen Z. “Surface microalcoholysis treatment: A novel approach towards froth flotation based separation for binary mixtures of polyethylene terephthalate and polyvinyl chloride”. Journal of Cleaner Production, 232, 848-857, 2019.
• [53] Ding J, Chen J, Ji Y, Ni P, Li Z, Xing L. “Kinetics of alcoholysis of poly(ethylene terephthalate) in sub- and super-critical isooctyl alcohol to produce dioctyl terephthalate”. Journal of Analytical and Applied Pyrolysis, 106, 99-103, 2014.
• [54] Babich MA, Bevington C, Dreyfus MA. "Plasticizer migration from children's toys, child care articles, art materials, and school supplies". Regulatory Toxicology and Pharmacology, 111, 1-9, 2020.
• [55] Liu D, Shen Y, Jiang P, Wai PT, Zhang Z, Zhang P, Agus H, Nie Z, Zhao M, Zhao, H. "An efficient cold-resistant strategy: synthesis and application of green cold-resistant bio-based plasticizer for poly (vinyl chloride)". European Polymer Journal, 142, 1-12, 2021.
• [56] Altindag IA, Akdogan Y. "Spectrophotometric characterization of plasticizer migration in poly (vinyl chloride)-based artificial leather". Materials Chemistry and Physics, 258, 1-7, 2021.
• [57] Cheng X, Yang W, Zhang Y, Kang Y, Ding Y, Zhiwei J, Cheng L. “Understanding the electro-stimulated deformation of PVC gel by in situ Raman spectroscopy”. Polymer Testing, 65(2), 90-96, 2018.
• [58] Tüzüm Demir AP, “Evaluation of the effect of boron waste sludge and clay on the diffusion of plasticizer to different environments from PVC composite films”. Research on Engineering Structures and Materials, 5(3), 263-278, 2019.
• [59] Zhang B, Han J. "Synthesis of SiO2@ PAA microspheres and their application for controlling diisooctyl terephthalate migration from flexible PVC materials". Micro & Nano Letters, 13(5), 661-665, 2018.
• [60] Mendizabal E, Cruz L, Jasso CF, Burillo G, Dakin VI. "Radiation crosslinking of highly plasticized PVC". Radiation Physics and Chemistry, 47(2), 305-309, 1996.
• [61] Tüzüm Demir AP, Ulutan S. “Assessment of degradation of plasticized poly(vinyl chloride) films through polyene formation under isothermal conditions”. Journal of Applied Polymer Science, 135(14), 1-10, 2018.
• [62] Tüzüm Demir AP, Ulutan S. “Degradation kinetics of PVC plasticized with different plasticizers under isothermal conditions”. Journal of Applied Polymer Science, 132(10), 1-12, 2015.
• [63] Wang Q, Wu W, Tang Y, Bian J, Zhu S. "Thermal degradation kinetics of plasticized poly (vinyl chloride) with six different plasticizers". Journal of Macromolecular Science, Part B, 56(6), 420-434, 2017.
• [64] Xue MY, Lu YH, Li K, Wang B, Lu YW. “Thermal characterization and kinetic analysis of polyvinyl chloride containing Sn and Zn”. Journal of Thermal Analysis and Calorimetry, 139, 1479-1492, 2020.
• [65] Yang Y, Huang J, Zhang R, Zhu J. “Designing bio-based plasticizers: Effect of alkyl chain length on plasticization properties of isosorbide diesters in PVC blends”. Materials and Design, 126, 29-36, 2017.
• [66] Pereira VA, Fonseca AC, Costa CSMF, Ramalho A, Coelho JFJ, Serra AC. “End-capped biobased saturated polyesters as effective plasticizers for PVC”. Polymer Testing, 85, 1-11, 2020.
• [67] Coman AE, Gabor AR, Nicolae CA, Raditoiu V, Hubca G, Iordache TV. “The influence of plasticizer nature and of processing mode upon the characteristics of flexible poly(vinyl chloride) composites”. Materiale Plastice, 56(4), 845-851, 2019.
• [68] Guo-min X, Yu-bi J, Yong L, Zhao Y, Hong T. "Rheological Properties of Plastisols Based on Low-Toxicity Plasticizers". Advanced Materials Research, 557-559, 1522-1527, 2012.
• [69] Xu GM, Ji YB, Yang Z, Tan H. “Influence of Structure and Property of Plasticizers on Viscosity and Aging Process of PVC Plastisols”. Applied Mechanics and Materials, 161, 15-20, 2012.
• [70] He Y, Qin S, Dyer BA, Zhang H, Zhao L, Chen T, Zheng F, Sun Y, Shi L, Rong Y, Qiu J. “Characterizing mechanical and medical imaging properties of polyvinyl chloride-based tissue-mimicking materials”. Journal of Applied Clinical Medical Physics, 20, 176-183, 2019.
• [71] Wang W, Wei F, Shi X, Yan J, Xie H, Wang Y, Zhang A, Wu J. “Synthesis of Polyurethane Anchoring Agent and Its Reinforcing Effects on Soft Polyvinyl Chloride”. Gaofenzi Cailiao Kexue Yu Gongcheng/Polymeric Materials Science and Engineering, 34(10), 7-13, 2018.
• [72] Coltro L, Pitta JB, da Costa PA, Perez MÂF, de Araújo VA, Rodrigues R. "Migration of conventional and new plasticizers from PVC films into food simulants: A comparative study". Food Control, 44, 118-129, 2014.
• [73] Wang M, Jiang J, Xia J, Ding H, Li M, Song X. “Plasticization and thermal behavior of hydroxyl and nitrogen rich group-containing tung-oil-based ester plasticizers for PVC”. New Journal of Chemistry, 42(4), 2422-2431, 2018.
• [74] Gama N, Santos R, Godinho B, Silva R, Ferreira A. “Triacetin as a Secondary PVC Plasticizer”. Journal of Polymers and the Environment, 27, 1294-1301, 2019.
• [75] Matos M, Cordeiro RA, Faneca H, Coelho JF, Silvestre AJ, Sousa A. "Replacing di (2-ethylhexyl) terephthalate by di (2-ethylhexyl) 2, 5-furandicarboxylate for PVC plasticization: synthesis, materials preparation and characterization". Materials, 12(14), 1-16, 2019.
• [76] Wang M, Song X, Jiang J, Xia J, Li M. "Binary amidecontaining tung-oil-based Ca/Zn stabilizers: effects on thermal stability and plasticization performance of poly (vinyl chloride) and mechanism of thermal stabilization". Polymer Degradation and Stability, 143, 106-117, 2017.
• [77] Chen J, Li X, Wang Y, Huang J, Li K, Nie X, Jiang J. “Epoxidized dimeric acid methyl ester derived from rubber seed oil and its application as secondary plasticizer”. Journal of Applied Polymer Science, 133(34), 1-7, 2016.
• [78] Silva AMS, Pimentel MF, Raimundo Jr IM, Almeida YM. “Effect of plasticizers on a PVC sensing phase for evaluation of water contamination by aromatic hydrocarbons and fuels using infrared spectroscopy”. Sensors and Actuators B: Chemical, 139(1), 222-230, 2009.
• [79] Pérez MDLAA, Marı́n LP, Quintana JC, Yazdani-Pedram M. “Influence of different plasticizers on the response of chemical sensors based on polymeric membranes for nitrate ion determination”. Sensors and Actuators B: Chemical, 89(3), 262-268, 2003.
• [80] Isildak Ö, Özbek O, Gürdere MB. “Development of chromium (III)-selective potentiometric sensor by using synthesized pyrazole derivative as an ionophore in PVC matrix and its applications”. Journal of Analysis and Testing, 4(4), 273-280, 2020.
• [81] Isildak Ö, Özbek O. “Silver (I)-selective PVC membrane potentiometric sensor based on 5, 10, 15, 20-tetra (4- pyridyl)-21 H, 23 H-porphine and potentiometric applications”. Journal of Chemical Sciences, 132(1), 1-8, 2020.
• [82] Srivastava SK, Gupta VK, Jain SA. “PVC‐based benzo‐15‐ crown‐5 membrane sensor for cadmium”. Electroanalysis, 8(10), 938-940, 1996.
• [83] Godwin AD. Applied Plastics Engineering Handbook. Editor: Kutz M. Plasticizers, 533-553, Chadds Ford, PA, USA, Elsevier Inc., 2017.
• [84] Czogała J, Pankalla E, Turczyn R. "Recent Attempts in the Design of Efficient PVC Plasticizers with Reduced Migration". Materials, 14(4), 1-28, 2021.