Synthesis and characterization of butyl methacrylate/1-hexene copolymers catalyzed by AlCl3 and organometallic acids and their performance assessment in lube oil
Vol 6, Issue 1, 2023
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Abstract
In the present work, a series of butyl methacrylate/1-hexene copolymers were synthesized, and their efficiency as viscosity index improvers, pour point depressants, and shear stabilizers of lube oil was investigated. The effect of 1-hexene molar ratio, type, and concentration of Lewis acids on the incorporation of 1-hexene into the copolymer backbone was investigated. The successful synthesis of the copolymers was confirmed through FTIR and 1H NMR spectroscopy. Results obtained from quantitative 1H NMR and GPC revealed that an increase in the molar ratio of 1-hexene to butyl methacrylate, along with concentration of Lewis acids led to an increase in 1-hexene incorporation and a reduction in Mn and Ð. Similar trends were observed when the Lewis acid changed from AlCl3 to organometallic acids. The maximum 1-hexene incorporation (26.4%) was achieved for sample BHY3, with a [1-hexene/BMA] ratio of 4 mol% and a [Yb(OTf)3/BMA] ratio of 2.5 mol%. Evaluation of the synthesized copolymers as lube oil additives demonstrated that the viscosity index was more significantly influenced by samples with higher molecular weight. Sample BHA13 represents maximum VI of 137. The copolymer containing Yb(OTf)3 as a catalyst exhibited superior efficiency as a pour point depressant. Furthermore, sample BHY3 showed the lowest shear stability index (6.4).
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1. Faujdar E, Singh RK. Studies on the application of poly(acrylate‐co‐maleic anhydride) amides with N‐phenyl‐p‐phenylenediamine as multifunctional lube additives. Journal of Applied Polymer Science. 2022; 139(21). doi: 10.1002/app.52195
2. Kumar A, Gupta T, Shukla A. A comparative assessment of performance behavior of mineral-based engine oils containing metal oxide nano-particles. Petroleum Science and Technology. 2022: 1-20. doi: 10.1080/10916466.2022.2150213
3. Rattana-Amron T, Klamchuen A. Kinetic analysis of oxidation characteristics in synthetic motor oil. Petroleum Science and Technology. 2021; 40(5): 604-625. doi: 10.1080/10916466.2021.2005091
4. Dyson CJ, Priest M, Lee PM. Simulating the Misting of Lubricant in the Piston Assembly of an Automotive Gasoline Engine: The Effect of Viscosity Modifiers and Other Key Lubricant Components. Tribology Letters. 2022; 70(2). doi: 10.1007/s11249-022-01589-0
5. van Ravensteijn BGP, Bou Zerdan R, Seo D, et al. Triple Function Lubricant Additives Based on Organic–Inorganic Hybrid Star Polymers: Friction Reduction, Wear Protection, and Viscosity Modification. ACS Applied Materials & Interfaces. 2018; 11(1): 1363-1375. doi: 10.1021/acsami.8b16849
6. Deka B, Sharma R, Mandal A, et al. Synthesis and evaluation of oleic acid based polymeric additive as pour point depressant to improve flow properties of Indian waxy crude oil. Journal of Petroleum Science and Engineering. 2018; 170: 105-111. doi: 10.1016/j.petrol.2018.06.053
7. Faujdar E, Negi H, Kukrety A, et al. Study of alkyl acrylate-co-maleic anhydride-based novel amide copolymers as multifunctional lubricant additives. Polymer Bulletin. 2020; 78(4): 2085-2102. doi: 10.1007/s00289-020-03204-5
8. Jalilian M, Jozaghkar M, Ziaee F. Novel insight into low-temperature performance of various polyalkyl methacrylate) homopolymers in lube oil. Polyolefins J. 2023. doi: 10.22063/poj.2023.3343.1258
9. Chikhaliya NP, Patel CK. Physico-chemical studies on Novel Terpolymers for Viscosity Index Improvers. Research Journal of Recent Sciences. 2015; 4: 291-298.
10. Covitch MJ, Trickett KJ. How Polymers Behave as Viscosity Index Improvers in Lubricating Oils. Advances in Chemical Engineering and Science. 2015; 05(02): 134-151. doi: 10.4236/aces.2015.52015
11. Jukic A, Vidovic E, Janovic Z. Alkyl methacrylate and styrene terpolymers as lubricating oil viscosity index improvers. Chemistry and Technology of Fuels and Oils. 2007; 43(5): 386-394. doi: 10.1007/s10553-007-0068-9
12. Chen C. Designing catalysts for olefin polymerization and copolymerization: beyond electronic and steric tuning. Nature Reviews Chemistry. 2018; 2(5): 6-14. doi: 10.1038/s41570-018-0003-0
13. Jozaghkar MR, Jalilian SM, Ziaee F. Synthesis and assessment of the effect of monomer feed ratio and Lewis acids on copolymerization of butyl methacrylate/1-octene. Polyolefins Journal. 2022; 9(2): 85-91.
14. Guo L, Liu W, Chen C. Late transition metal catalyzed α-olefin polymerization and copolymerization with polar monomers. Materials Chemistry Frontiers. 2017; 1(12): 2487-2494. doi: 10.1039/c7qm00321h
15. Li G, Xu G, Ge Y, et al. Synthesis of fluorinated polyethylene of different topologies via insertion polymerization with semifluorinated acrylates. Polymer Chemistry. 2020; 11(39): 6335-6342. doi: 10.1039/d0py00993h
16. Venkatesh R, Harrisson S, Haddleton DM, et al. Olefin Copolymerization via Controlled Radical Polymerization: Copolymerization of Acrylate and 1-Octene. Macromolecules. 2004; 37(12): 4406-4416. doi: 10.1021/ma035986m
17. Xiao C, Jiang L, Dan Y. Effect of Long-Chain Branch of Poly(methyl acrylate-co-1-octene) on the Vulcanization and Mechanical Properties. Industrial & Engineering Chemistry Research. 2019; 58(19): 7857-7865. doi: 10.1021/acs.iecr.9b00328
18. Hirooka M, Yabuuchi H, Iseki J, et al. Alternating copolymerization through the complexes of conjugated vinyl monomers–alkylaluminum halides. Journal of Polymer Science Part A-1: Polymer Chemistry. 1968; 6(5): 1381-1396. doi: 10.1002/pol.1968.150060528
19. Xiao C, Yu Y, Jiang L, et al. Insight into Copolymerization of Methyl (Meth)Acrylate and 1-Octene with Aluminum Trichloride. Industrial & Engineering Chemistry Research. 2018; 57(49): 16604-16614. doi: 10.1021/acs.iecr.8b03215
20. Luo R, Chen Y, Sen A. Effect of Lewis and Brønsted acids on the homopolymerization of acrylates and their copolymerization with 1‐alkenes. Journal of Polymer Science Part A: Polymer Chemistry. 2008; 46(16): 5499-5505. doi: 10.1002/pola.22870
21. Carlson RK, Lee RA, Assam JH, et al. Free-radical copolymerisation of acrylamides, acrylates, and α-olefins. Molecular Physics. 2015; 113(13-14): 1809-1822. doi: 10.1080/00268976.2015.1015641
22. Jozaghkar MR, Ziaee F, Jalilian S. Synthesis, kinetic study and characterization of living anionic polymerized polystyrene in cyclohexane. Iranian Polymer Journal. 2022; 31(4): 399-412. doi: 10.1007/s13726-021-01009-5
23. Jozaghkar MR, Sepehrian Azar A, Ziaee F Synthesis and characterization of semi-interpenetrating polymer network hydrogel based on polyacrylic acid/polyallylamine and its application in wastewater remediation. Polymer Bulletin. 2023; 80: 2119–2135.
24. Ziaee F, Ronagh-Baghbani M, Jozaghkar MR. Microstructure characterization of low molecular weight polybutadiene using the chain end groups by nuclear magnetic resonance spectroscopy. Polymer Bulletin. 2019; 77(5): 2345-2365. doi: 10.1007/s00289-019-02863-3.
25. Jozaghkar MR, Ziaee F, Azar AS. Investigation of poly(α-methyl styrene) tacticity synthesized by photo- polymerization. Polymer Bulletin. 2021; 78: 5303–5314.
26. Kim WH, Jeon BH, Noh KS, et al. Catalytic composition for producing 1-alkene and acrylates copolymer and method for producing 1-alkene and acrylates copolymer. LG Chem Ltd; 2012.
27. Li M, Zhang H, Cai Z, et al. Norbornene polymerization and copolymerization with 1-alkenes by neutral palladium complexes bearing aryloxide imidazolin-2-imine ligand. Polymer Chemistry. 2019; 10(21): 2741-2748. doi: 10.1039/c9py00176j
28. Kaur S, Singh G, Kothari AV, et al. Methyl acrylate/1‐octene copolymers: Lewis acid‐mediated polymerization. Journal of Applied Polymer Science. 2008; 111(1): 87-93. doi: 10.1002/app.28983
29. Elganidi I, Elarbe B, Abdullah N, et al. Synthesis of a novel terpolymer of (BA-co-SMA-co-MA) as pour point depressants to improve the flowability of the Malaysian crude oil. Materials Today: Proceedings. 2021; 42: 28-32. doi: 10.1016/j.matpr.2020.08.628
30. Faujdar E, Singh RK. Comparative study of poly(acrylate-co-maleimide) copolymers and poly(α-olefins-co-maleimide) copolymers of hindered phenolic Schiff base amine for lubricant applications. Journal of Polymer Research. 2022; 29(3). doi: 10.1007/s10965-022-02935-5
31. Hoque M, Paul S, Ghosh P. Castor oil based eco-friendly lubricating oil additives. Journal of Macromolecular Science, Part A. 2020; 58(5): 329-335. doi: 10.1080/10601325.2020.1854045
32. Kuraimid ZKh, Ammouri QM, Ahmed TA, et al. Synthesis of viscosity index improver for motor lubricating oil. Eurasian Chemical Communications. 2021; 3(7): 477-483.
33. Jalilian SM, Ziaee F. Polymerization parameters of methacrylic acid esters as viscosity index improvers in lubricants. Iran Journal Polym Sci Technol. 2019; 32: 123-134.
34. Pucko I, Racar M, Faraguna F. Synthesis, characterization, and performance of alkyl methacrylates and tert-butylaminoethyl methacrylate tetra polymers as pour point depressants for diesel Influence of polymer composition and molecular weight. Fuel. 2022; 324: 124821. doi: 10.1016/j.fuel.2022.124821
DOI: https://doi.org/10.24294/jpse.v6i1.4957
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