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The Anhydride-Amic Acid-Imide Forms of Maleinized Soybean Oil

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Abstract

Vegetable oil is one of the most promising renewable feedstocks as an alternative to fossil resources, but there are few studies aiming to transform it into hydrophilic materials. We proposed a facile method to prepare water-soluble derivatives from soybean oil, which could become water resistant again after simple heat treatment. The model vegetable oil, soybean oil (SO), was first reacted with maleic anhydride (MA) by the Alder ene reaction to obtain maleinized soybean oil (SOMA), and SOMA was further reacted with gaseous ammonia to obtain the maleamic acid form (SOMA-Amic acid), which was very soluble in water (solubility>100 mg/mL). The obtained water-soluble product was converted to the water-resistant maleimide form (SOMA-Imide) by a simple heat treatment. The potential application of these vegetable oil derived materials was demonstrated in paper sizing as an example. SOMA-Amic acid was demonstrated to be a novel green material, which can be used in an aqueous process and then heat-treated to become water-resistant in the final product.

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References

  1. Gandini, A.; Lacerda, T. M., Introduction. In Polymers from Plant Oils, 2nd Ed.; Scrivener Publishing: Beverly, 2018; pp. 1–8.

    Chapter  Google Scholar 

  2. Jia, L. H. Application and synthesis of fatty acid derivatives in deinking process of waste paper. Fine Spec. Chem. 2013, 21, 28–31.

    CAS  Google Scholar 

  3. Leung, D. Y. C.; Wu, X.; Leung, M. K. H. A review on biodiesel production using catalyzed transesterification. Appl. Energy 2010, 87, 1083–1095.

    Article  CAS  Google Scholar 

  4. Kim, K. H.; Lee, E. Y. Simultaneous production of transformer insulating oil and value-added glycerol carbonates from soybean oil by lipase-catalyzed transesterification in dimethyl carbonate. Energies 2018, 11, 82.

    Article  Google Scholar 

  5. Muturi, P.; Wang, D.; Dirlikov, S. Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils. Prog. Org. Coat. 1994, 25, 85–94.

    Article  CAS  Google Scholar 

  6. Khot, S. N.; Lascala, J. J.; Can, E.; Morye, S. S.; Williams, G. I.; Palmese, G. R.; Kusefoglu, S. H.; Wool, R. P. Development and application of triglyceride-based polymers and composites. J. Appl. Polym. Sci. 2001, 82, 703–723.

    Article  CAS  Google Scholar 

  7. Bandele, O. J.; Cureton, L. T.; Bailey, A. B.; Ogungbesan, A. A review of dietary exposure and toxicological information on epoxidised soybean oil (ESBO) in food-contact applications. Food Addit. Contam., Part A 2018, 35, 2204–2219.

    Article  CAS  Google Scholar 

  8. Tran, P.; Seybold, K.; Graiver, D.; Narayan, R. Free radical maleation of soybean oil via a single-step process. J. Am. Oil Chem. Soc. 2005, 82, 189–194.

    Article  CAS  Google Scholar 

  9. Nagakura, M.; Yoshitomi, K. Reaction of maleic anhydride with unsaturated fatty acids in the presencef organic peroxides. Yukagaku 1972, 21, 83–91.

    CAS  Google Scholar 

  10. Espinoza, A. M. Polymer composition derived from unsaturated vegetable oils. 2000, US6103834.

  11. Soliman, E. A.; Elkatory, M. R.; Hashem, A. I.; Ibrahim, H. S. Synthesis and performance of maleic anhydride copolymers with alkyl linoleate or tetra-esters as pour point depressants for waxy crude oil. Fuel 2018, 211, 535–547.

    Article  CAS  Google Scholar 

  12. Tuama, R. J.; Al-Dokheily, M. E.; Khalaf, M. N. Synthesis and evaluation of maleic anhydride-methyl oleate copolymer as a corrosion inhibitor for C-steel in 0.1 M HCl solution. Int. J. Electrochem. Sci. 2020, 15, 12740–12755.

    Article  CAS  Google Scholar 

  13. Deka, B.; Sharma, R.; Mahto, V. Synthesis and performance evaluation of poly(fatty esters-co-succinic anhydride) as pour point depressants for waxy crude oils. J. Pet. Sci. Eng. 2020, 191, 107153.

    Article  CAS  Google Scholar 

  14. Root, F. B. Improvement of drying oils. 1945, US2374381.

  15. Bickford, W. G.; Fisher, G. S.; Kyame, L.; Swift, C. E. Autoxidation of fats. II. Preparation and oxidation of methyl oleate-maleic anhydride adduct. J. Am. Oil Chem. Soc. 1948, 25, 254–257.

    Article  CAS  Google Scholar 

  16. Rheineck, A. E.; Khoe, T. H. Reaction of maleic anhydride with cis-isolated unsaturated fatty acid esters. Fette, Seifen, Anstrichm. 1969, 71, 644–652.

    Article  CAS  Google Scholar 

  17. Stefanoiu, F.; Candy, L.; Vaca-Garcia, C.; Borredon, E. Kinetics and mechanism of the reaction between maleic anhydride and fatty acid esters and the structure of the products. Eur. J. Lipid Sci. Technol. 2008, 110, 441–447.

    Article  CAS  Google Scholar 

  18. Quesada, J.; Morard, M.; Vaca-García, C.; Borredon, E. Preparation of alkenyl succinic anhydrides from vegetable oil FAME. J. Am. Oil Chem. Soc. 2003, 80, 281–286.

    Article  CAS  Google Scholar 

  19. Candy, L.; Vaca-Garcia, C.; Borredon, E. Synthesis and characterization of oleic succinic anhydrides: structure-property relations. J. Am. Oil Chem. Soc. 2005, 82, 271–277.

    Article  CAS  Google Scholar 

  20. Eren, T.; Küsefoğlu, S. H.; Wool, R. Polymerization of maleic anhydride–modified plant oils with polyols. J. Appl. Polym. Sci. 2003, 90, 197–202.

    Article  CAS  Google Scholar 

  21. Isogai, A.; Morimoto, S. Sizing performance and hydrolysis resistance of alkyl oleate succinic anhydrides. Tappi J. 2004, 3, 8–12.

    CAS  Google Scholar 

  22. Lackinger, E.; Schmid, L.; Sartori, J.; Isogai, A.; Potthast, A.; Rosenau, T. Novel paper sizing agents from renewables. Part 1: preparation of a paper sizing agent derived from natural plant oils. Holzforschung 2011, 65, 3–11.

    Article  CAS  Google Scholar 

  23. Candy, L.; Vaca-Garcia, C.; Borredon, E. Synthesis of alkenyl succinic anhydrides from methyl esters of high oleic sunflower oil. Eur. J. Lipid Sci. Technol. 2005, 107, 3–11.

    Article  CAS  Google Scholar 

  24. Snider, B. B. Lewis-acid catalyzed ene reactions. Acc. Chem. Res. 1980, 13, 426–432.

    Article  CAS  Google Scholar 

  25. Amos, R. C.; Kuska, M.; Mesnager, J.; Gauthier, M. Thermally induced maleation of soybean and linseed oils: from benchtop to pilot plant. Ind. Crops Prod. 2021, 166, 113504.

    Article  CAS  Google Scholar 

  26. Chen, C.; Xu, C.; Zhai, J.; Ma, Y.; Zhao, C.; Yang, W. Solvent-free preparation of uniform styrene/maleimide copolymer microspheres from solid poly(styrene-alt-maleic anhydride) microspheres. Polym. Chem. 2022, 13, 684–692.

    Article  CAS  Google Scholar 

  27. Schönberg, A.; Ismail, A. F. A. Colour reaction of maleic anhydride, p-benzoquinone, their partially substituted derivatives, and citric acid. Some zwitterions. J. Chem. Soc. 1940, 1374–1378.

    Google Scholar 

  28. Lackinger, E.; Schmid, L.; Sartori, J.; Isogai, A.; Potthast, A.; Rosenau, T. Novel paper sizing agents from renewables. Part 2: Characterization of maleated high oleic sunflower oil (MSOHO). Holzforschung 2011, 65, 13–19.

    Article  CAS  Google Scholar 

  29. Maganu, M.; Chira, N.; Stavarache, C.; Andronescu, C.; Anastasiu, A. Assessment of maleinization degree of linseed oil from spectral data. Rev. Chim. 2016, 67, 276–281.

    CAS  Google Scholar 

  30. Jin, Z.; Du, L.; Zhang, C.; Sugiyama, Y.; Wang, W.; Palui, G.; Wang, S.; Mattoussi, H. Modification of poly(maleic anhydride)-based polymers with H2N-R nucleophiles: addition or substitution reaction. Bioconjugate Chem. 2019, 30, 871–880.

    Article  CAS  Google Scholar 

  31. Yang, J.; Zhang, S.; Sun, W.; Bai, Y. Proton nuclear magnetic resonance spectroscopy of acitve hydrogen. Univ. Chem. 2019, 34, 82–88.

    Article  CAS  Google Scholar 

  32. Matsubara, K.; Nakato, T.; Tomida, M. 1H and 13C NMR characterization of poly(succinimide) prepared by thermal polycondensation of L-aspartic acid1. Macromolecules 1997, 30, 2305–2312.

    Article  CAS  Google Scholar 

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Acknowledgments

This work was financially supported by an internal fund from Tsinghua University.

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Authors and Affiliations

  1. Department of Chemical Engineering, Tsinghua University, Beijing, 100084, China

    Yun Zhou, Yan-Bin Huang & Wan-Tai Yang

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  1. Yun Zhou
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  2. Yan-Bin Huang
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Correspondence to Yan-Bin Huang or Wan-Tai Yang.

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Wan-Tai Yang is an editorial board member for Chinese Journal of Polymer Science and was not involved in the editorial review or the decision to publish this article. All authors declare that there are no competing interests.

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Zhou, Y., Huang, YB. & Yang, WT. The Anhydride-Amic Acid-Imide Forms of Maleinized Soybean Oil. Chin J Polym Sci 41, 1829–1835 (2023). https://doi.org/10.1007/s10118-023-2980-9

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  • DOI: https://doi.org/10.1007/s10118-023-2980-9

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