Comparative Studies between Conventional Techniques and Green Chemistry to Synthesis of Novel Piperidinium Salts Ionic Liquids (PBSILs)

Subject Areas : Journal of Chemical Health Risks

Shakir M. Saied ¹ , Salim J. Mohammed ² , Bassam T. Khaleel ³ , Mohanad Saleh ^{4 *}

1 - Department of Medical Laboratories Technologies, Al-Noor University College, Barttella, Mosul, Iraq
2 - Department of Chemistry, College of Science, University of Mosul, Ninevah, Iraq
3 - Department of Dentistry, Al-Noor University College, Barttella, Mousl, Iraq
4 - Department of Chemistry, College of Education for pure science, University of Mosul. Ninevah, Iraq

Received: 2021-08-30 Accepted : 2021-11-27 Published : 2021-12-01

Keywords: Ionic liquids, Synthesis, Alkyl piperidinium salts, Spectroscopic investigation Introduction,

Abstract :

Comparative studies between conventional technique, method (A) and green chemistry (microwave irradiation) , method (B) to synthesis of four novel unsymmetrical alkyl piperidinium salts ionic liquids (PBSILs) by the addition of alkyl halides (methyl or allyl) to piperidine with yields more than (90%) in method (A) and less than (70%) in method (B) respectively with decrease reaction time. Theses novel organic salts are characterized by elemental analysis, 1H NMR, FTIR and mass spectrometry.

References:

1. Raoof M.Y., Saied M.Sh., Al Gawady M.S., 1970. 2-Phenylchroman-4-one as Synthone in Synthesis of New Five and Six Membered Rings Heterocyclic Compounds. Journal of Education and Science. 24(4), 50-59.‏


2. Posada P., Brana M.F., Villarino A.L., Dominguez V., Ortuno I., Martínez C., 2011. Synthesis of new vinylpyridinium salts. Journal of Heterocyclic Chemistry. 48(3), 549-554.‏


3. Okazaki K., Maeda T., Nagamune H., Manabe Y., Kourai H., 1997. Synthesis and antimicrobial characteristics of 4, 4'-(α, ω-polymethylenedithio) bis (1-alkylpyridinium iodide) s. Chemical and Pharmaceutical Bulletin. 45(12), 1970-1974‏.


4. Alptüzün V., Parlar S., Taşlı H., Erciyas E., 2009. Synthesis and antimicrobial activity of some pyridinium salts. Molecules. 14(12), 5203-5215.‏


5. Wilkes J.S., Levisky J.A., Wilson R.A., Hussey C.L., 1982. Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis. Inorganic Chemistry. 21(3), 1263-1264.‏


6. Baudequin C., Brégeon D., Levillain J., Guillen F., Plaquevent J.C., Gaumont A.C., 2005. Chiral ionic liquids, a renewal for the chemistry of chiral solvents? Design, synthesis and applications for chiral recognition and asymmetric synthesis. Tetrahedron: Asymmetry. 16(24), 3921-3945.‏


7. Levillain J., Dubant G., Abrunhosa I., Gulea M., Gaumont A.C., 2003. Synthesis and properties of thiazoline based ionic liquids derived from the chiral pool. Chemical Communications. 23, 2914-2915.‏


8. You W., Ganley J.M., Ernst B.G., Peltier C.R., Ko H.Y., DiStasio R.A., Knowles R.R., Coates G.W., 2021. Expeditious synthesis of aromatic-free piperidinium-functionalized polyethylene as alkaline anion exchange membranes. Chemical Science. 12(11), 3898-3910.‏


9. Badrey M.G., Gomha S.M., 2012. 3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4, 5-dihydro-3H-chromeno [2, 3-d] pyrimidine: An effecient key precursor for novel synthesis of some interesting triazines and triazepines as potential anti-tumor agents. Molecules. 17(10), 11538-11553.‏


10. Khadilkar B.M., Rebeiro G.L., 2002. Microwave-assisted synthesis of room-temperature ionic liquid precursor in closed vessel. Organic Process Research & Development. 6(6), 826-828.‏


11. Messali M., 2016. A facile and green microwave-assisted synthesis of new functionalized picolinium-based ionic liquids. Arabian Journal of Chemistry. 9, S564-S569.‏


12. Abdullah L.W., Saied S.M., Saleh M.Y., 2021. Deep eutectic solvents (Reline) and Gold Nanoparticles Supported on Titanium Oxide (Au–TiO₂) as New Catalysts for synthesis some substituted phenyl (substituted-3-phenyloxiran) methanone Enantioselective Peroxidation. Egyptian Journal of Chemistry. 64(8), 4381-4389.‏


13. Sdeek G.T., Mauf R.M., Saleh M.Y., 2021. Synthesis and Identification of some new Derivatives Oxazole, Thiazole and Imidazol from Acetyl Cysteine. Egyptian Journal of Chemistry. 71(12), 7465-7471.


14. Hamdoon A.M., Al-Iraqi M.A., Saleh M.Y., 2021. Synthesis of Some Multi-cyclic Sulfhydryl Donor Compounds Containing 1, 2-dithiol-3-thione moiety. Egyptian Journal of Chemistry, (Article In Press).


15. Aldahham B.J., Al-Khafaji K., Saleh M.Y., Abdelhakem A.M., Alanazi A.M., Islam M.A., 2020. Identification of naphthyridine and quinoline derivatives as potential Nsp16-Nsp10 inhibitors: a pharmacoinformatics study. Journal of Biomolecular Structure and Dynamics. 1-8.‏


16. Saleh M.Y., Ayoub A.I., 2014. Synthesis of new derivatives of 2 – chloro – 3 – formyl - 1, 8-naphthyridine. European Journal of Chemistry. 5(3), 475-480.‏


17. Lava K., Binnemans K., Cardinaels T., 2009. Piperidinium, piperazinium and morpholinium ionic liquid crystals. The Journal of Physical Chemistry B. 113(28), 9506-9511.‏

18.Albalawi A.H., El-Sayed W.S., Aljuhani A., Almutairi S.M., Rezki N., Aouad M.R., Messali M., 2018. Microwave-assisted synthesis of some potential bioactive imidazolium-based room-temperature ionic liquids. Molecules. 23(7), 1727.‏

19. Winstead A.J., Nyambura G., Matthews R., Toney D., Oyaghire S., 2013. Synthesis of quaternary heterocyclic salts. Molecules. 18(11), 14306-14319.‏


20. Burke J.R., Frey P.A., 1996. Correlation of electronic effects in N-alkylnicotinamides with NMR chemical shifts and hydride transfer reactivity. The Journal of Organic Chemistry. 61(2), 530-533.‏‏


21. Hesse M., Meier H., Zeeh B., 2008. Spectroscopic methods in organic chemistry. Thieme/Houben-Weyl Series.‏


22. Silverstein R.M., Bassler G.C., 1962. Spectrometric identification of organic compounds. Journal of Chemical Education. 39(11), 546.‏