Computational study of synthetic and natural polymer additives - Antioxidant potential of BHA, TBHQ, BHT, and curcumin

被引:27
作者
Thbayh, Dalal K. [1 ,2 ]
Fiser, Bela [1 ,3 ,4 ]
机构
[1] Univ Miskolc, Inst Chem, H-3515 Miskolc, Hungary
[2] Univ Basrah, Polymer Res Ctr, Basrah, Iraq
[3] Univ Miskolc, Higher Educ & Ind Cooperat Ctr, H-3515 Miskolc, Hungary
[4] Ferenc Rakoczi II Transcarpathian Hungarian Coll, UA-90200 Transcarpathia, Beregszasz, Ukraine
关键词
DFT; Phenolic compounds; Antioxidant mechanism; HAT; SETPT; SPLET; BOND-DISSOCIATION ENTHALPIES; SCAVENGING ACTIVITY; ELECTRON; THERMOCHEMISTRY; THERMODYNAMICS; MECHANISM; ENERGIES; KINETICS; PROTON; DFT;
D O I
10.1016/j.polymdegradstab.2022.109979
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The antioxidant potential of commonly used synthetic and natural antioxidant additives, including buty-lated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), tert-butylhydroquinone (TBHQ), and natural additive, curcumin have been studied and compared by calculating the bond dissociation enthalpy (BDE), ionization potential (IP), proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE) values for each potential hydrogen donor site. The results indicate that, in each additive an O-H group has the highest antioxidant potential (lowest BDE value). The studied molecules can be ranked based on their antioxidant potential as follows: BHT > BHA approximate to TBHQ > curcumin A > curcumin D. By comparing with commonly used polymers, in each studied species, there is at least one X-H bond which has a lower BDE value than in the corresponding polymeric material. Thus, all studied additives are potentially applicable to protect polymeric materials. BHT is the best radical scavenger additive in case of the hydrogen atom transfer (HAT), and the sequential proton loss electron transfer (SPLET) mechanisms to donate a H atom, but in single electron transfer proton transfer (SETPT) curcumin could also be suitable. (C) 2022 The Author(s). Published by Elsevier Ltd.
引用
收藏
页数:8
相关论文
共 56 条
[1]   Color, flavonoids, phenolics and antioxidants of Omani honey [J].
Al-Farsi, Mohamed ;
Al-Amri, Abeer ;
Al-Hadhrami, Ahlam ;
Al-Belushi, Sharifa .
HELIYON, 2018, 4 (10)
[2]   A physicochemical examination of the free radical scavenging activity of Trolox: mechanism, kinetics and influence of the environment [J].
Alberto, Marta E. ;
Russo, Nino ;
Grand, Andre ;
Galano, Annia .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (13) :4642-4650
[3]  
Ambrogi V, 2017, PDL HANDB SER, P87, DOI 10.1016/B978-0-323-44353-1.00004-X
[4]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[5]   DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].
BECKE, AD .
PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100
[6]   Theoretical study on Curcumin: A comparison of calculated spectroscopic properties with NMR, UV-vis and IR experimental data [J].
Benassi, Rois ;
Ferrari, Erika ;
Lazzari, Sandra ;
Spagnolo, Ferdinando ;
Saladini, Monica .
JOURNAL OF MOLECULAR STRUCTURE, 2008, 892 (1-3) :168-176
[7]   Kinetic study on the thermal degradation of polypropylene and polyethylene [J].
Bockhorn, H ;
Hornung, A ;
Hornung, U ;
Schwaller, D .
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 1999, 48 (02) :93-109
[8]   Comparative study of the radical scavenging behavior of ascorbic acid, BHT, BHA and Trolox: Experimental and theoretical study [J].
Boulebd, Houssem .
JOURNAL OF MOLECULAR STRUCTURE, 2020, 1201
[9]  
Cardoso S.M, 2019, ANTIOXIDANT CAPACITI, V24, P492
[10]   Bio-based additives for thermoplastics [J].
De Paoli, Marco Aurelio ;
Waldman, Walter Ruggeri .
POLIMEROS-CIENCIA E TECNOLOGIA, 2019, 29 (02)