Synthesis and Characterization of Co-Polymer (Styrene / Allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside) and Studying some of its thermal properties
DOI:
https://doi.org/10.21123/bsj.2023.7378Keywords:
Allyl bromide, Carbohydrates, Eco-friendly polymers, Glucose, Oxidation Induction Time, PolystyreneAbstract
In this research, a Co-polymer (Styrene / Allyl-2.3.4.6-tetra-O-acetyl-β-D-glucopyranoside) was synthesized from glucose in four steps using Addition Polymerization according to the radical mechanism using Benzoyl Peroxide (BP) as initiator. Initially, Allyl-2.3.4.6-tetra-O-acetyl-β-D-glucopyranoside monomer was prepared in three steps and the reaction was followed by (HPLC, FT-IR, TLC), in the fourth step the monomer was polymerized with Styrene and the structure was determined by FT-IR and NMR spectroscopy. The reaction conditions (temperature, reaction time, material ratios) were also studied to obtain the highest yield, the relative, specific and reduced viscosity of the prepared polymer was determined, from which the viscosity average molecular weight was calculated, which amounted to about (63,000 g/mol). Thermal properties of the polymer were studied by Differential Scanning Calorimeter (DSC) and determining the Oxidation Induction Time (OIT).
Received 4/5/2022
Revised 21/8/2022
Accepted 22/8/2022
Published Online First 20/2/2023
References
Maiti S, Manna S, Banahene N, Pham L, Liang Z, Wang J, et al. From Glucose to Polymers : A Continuos Chemoenzymatic Process. Angew. Chem.2020 Oct; 59(43): 18943-18947.
Zhang Y, Chan JW, Moretti A, Uhrich KE. Designing polymers with sugar-based advantages for bioactive delivery applications. J Control Release. 2015; 219: 355-368.
Azeez MA, Olatunde OC. Recent Developments on The Application of Carbohydrate Polymers. J Appl Chem. 2018 July; 11(7): 68-80.
Bhaumik A, Peterson GI, Kang C, Choi TL. Controlled Living Cascade Polymerization To Make Fully Degradable Sugar-Based Polymers from d-Glucose and d-Galactose. J Am Chem Soc. 2019; 141(31): 12207-12211.
Gregory GL, Jenisch LM, Charles B, Kociok-Köhn G, Buchard A. Polymers from Sugars and CO2: Synthesis and Polymerization of a D‑Mannose-Based Cyclic Carbonate. Macromolecules. 2016 Sep; 49(19): 7165-7169.
Nasiri M, Reineke TM. Sustainable glucose-based block co-polymers exhibit elastomeric and adhesive behavior. Polym Chem. 2016 Jul; 7(33): 5233-5240.
Kartha KPR, Field RA. Iodine: A Versatile Reagent in Carbohydrate Chemistry IV. Per-O-Acylation And Acetolysis. Tetrahedron. 1997 Aug; 53(34): 11753-11766.
Chittaboina S, Hodges B, Wang Q. A Facile Route for the Regioselective Deacetylation of Peracetylated Carbohydrates at Anomeric Position. Lett Org Chem. 2006 Oct; 3(1): 35-38.
Wang T, Demchenko AV. Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies. Org Biomol Chem. 2019 May 28; 17(20): 4934-4950.
Kaya E, Sonmez F, Kucukislamoglu M, Nebioglu M. Selective anomeric deacetylation using zinc acetate as catalyst. Chem Pap. 2012 Feb; 66(4): 312-315.
Zhang J, Kovac P. An Alternative Method for Regioselective, Anomeric Deacylation of Fully Acylated Carbohydrates. J. Carbohydr. Chem. 2008 Feb; 18(4): 461-469.
Bhaumik K, Salgaonkar P, Akamanchi KGG. Regioselective Anomeric Deacetylation of Peracetylated Glucopyranoses. Aust. J. Chem. 2003; 34(50): 909-911.
Das T, Praveen T, Shashidhar MS. Mechanism of Silver (l) Oxide Mediated O-Alkylation of 2.4-di-O-Acyl-Myo-inositol 1.3.5-orthoformates: Effect of Solvent And Silver Halide on The Nature of The Intermediates involved. Carbohydr. Res. 1998; 313(1): 55-59.
Ren B, Yan N, Gan L. Regioselective alkylation of carbohydrates and diols: a cheaper iron catalyst, new applications and mechanism. Rsc Adv. 2017 Sep; 7(73): 46257-46262.
Vardareli TK, Keski S, Usanmaz A. Synthesis and Characterization of Poly(allyl methacrylate) Obtained by Free Radical Initiator. J. Macromol. Sci. A. 2008 Apr; 45(4): 302-311.
Chang H, Chen X, Hu Q, Shi Y, Zheng R, Fan J, et al. Synthesis, characterization and properties of poly(N‑allyl‑tetrasubstituted imidazole). Poly. Bull. 2019 Jan; 76(23): 5683-5699.
Al-Ahmad T, Al-Deri F. Intrinsic viscosity [η], Kwert-Value and viscosity average molecular relationship for some polymers. Damascus Univ. J. Basic Sci. 2012 Dec; 28(2): 13-31.
Yigit Y, Kilislioglu A, Karakus S, Baydogan N. Determination of the intrinsic viscosity and molecular weight of Poly(methyl methacrylate) blends. J. Investig. Eng. Technol. 2019 Dec; 2(2): 34-39.
Marcus SM, Blaine RL. Estimation of Bias in the Oxidative Induction Time Measurement by Pressure DSC. ASTM International 1997; 172-183. http://www.tainstruments.com/pdf/literature/TA228.pdf
Downloads
Published
Issue
Section
License
Copyright (c) 2023 Baghdad Science Journal
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
