The Synthesis and Characterization of Acetamide Compounds from α-pinene and Acetonitrile through Ritter Reaction

  • Zahra Ramadhany Hidayat Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Brawijaya, Malang, Indonesia
  • Mohammad Farid Rahman Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Brawijaya, Malang, Indonesia
Keywords: Turpentine Oil, α-pinene, acetonitrile, Ritter Reaction, acetamides

Abstract

The ultimate objectives of this research were to synthesize and characterize acetamides as α-pinene derivative compounds produced through Ritter reaction between α-pinene and acetonitrile. Turpentine oil was isolated through fractional distillation under diminished pressure of 50-100mmHg and temperature of 70-90°C, which produced 91.33% of α-pinene as the distillate. Meanwhile, the procedure of the synthesis involved dissolving acetonitrile in α-pinene, adding sulfuric acid dropwise at 6 drops per minute and stirring at room temperature, followed by extraction with diethyl ether and concentrated with N2 gas. The compounds produced from turpentine oil isolation and synthesis through Ritter reaction is characterized by Infra-Red Spectrophotometer and Gas Chromatography-Mass Spectrometry (GC-MS). The distillate α-pinene was found to readily react with acetonitrile under the catalysis of concentrated sulfuric acid to give varieties of acetamide compounds as the products. The corresponding acetamide compounds resulted in good yields were based on its carbocation stability and rearrangement, which were N-[1-Methyl-1-(4-methyl-cyclohex-3-enyl)-ethyl]-acetamide (51.3%) as the main product and N-(2,6,6-trimethylbicyclo(3.1.1) hept-2-yl)-acetamide (4.86%) and N-(1,5-Dimethyl-1-vinyl-hex-4-enyl)-acetamide (20.29%) as the byproducts.

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References

[1] Aspan, R., “Pengembangan Pemanfaatan Obat Bahan Alam dalam Pelayanan Kesehatan Masyarakat”, Makalah Seminar Tanaman Obat Indonesia, Tawangmangu, Surakarta, 2004.
[2] Kinghorn, A.D., Cui, B., Ito, A., Chung, H.S., Seo, E.K., Long, L., and Chang, L.C., “Fractionation of Plants to Discover Substances to Combat Cancer, in Cutler, S.J., Cutler, H.G., (Ed.)”, Biologically Active Natural Products: Pharmaceuticals, New York: CRC Press, pp. 17-24, 2000.
[3] Kadarohman, “Eksplorasi Minyak Atsiri Sebagai Bioaditif Bahan Bakar Solar”, Fakultas MIPA, Universitas Pendidikan Indonesia, 2008.
[4] Rahman M.F., and Masruri, “Isomerisasi dalam Suasana Asam: Sintesis Senyawa Kairomon Adalia Bipunctata”, Laporan Penelitian, Fakultas MIPA Universitas Brawijaya, Malang, 2004.
[5] Dragan, “On the Ritter Synthesis of N-tert-Butylacrylamide (Part II)* Reaction between tert Butylalcohol and Acrylonitrile in Non-aqueous Solvents”, Iranian J. of Polymer Science and Technology, vol 4, no 1, 1995.
[6] Ibatullin, U.G., Mukhametova, D.Ya., Makaeva, R.M., Safarov, M.G., and Tolstikov, G.A., “Chemistry of Di- and Tetrahydropyrans Communication 5. Ritter Reactions in the Pyran Series”, Russian Chemical Bulletin, vol 35, no. 2, pp. 356-360, 1986.
[7] Kametani, T.K., and Fukomoto, “Synthetic and Natural Sources of the Isoquinolines nucleus”, New York: John Wiley & Sons, Inc, 1981.
[8] Parris, C.L., “Organic Synthesis: Collective Volume V”, New York: John Wiley & Sons Inc., 1973,
[9] Sastrohamidjojo, “Kimia Minyak Atsiri”, Yogyakarta: Gadjah Mada University Press, 2004.
[10] Nohong, “Oksidasi Senyawa α-pinena Hasil Isolasi Minyak Terpentin menggunakan Aliran Gas Oksigen dengan Katalis Zeolit NaX”, Tesis S2, Yogyakarta: Universitas Gadjah Mada, 2000.
[11] Clarke, T., Devine, J., dan Dicker, D.W., “Application of the Ritter Reaction to α-Olefins”, Unilever Research Laboratory, Port Sunlight, Cheshire, England, 1964.
[12] Masten, S., “Terpentine Oil and Terpinolene: Review of Toxicological Literature”, Environ. Health Sci, 9, pp. 6-7, 1999.
[13] Pine, S.H., Hendrickson, J.B., Cram, D.J., and Hammond, G.S., “Kimia Organik, jilid 2, Terjemah: Roehayati dan Sasanti”, Bandung: Penerbit ITB, 1980.
Published
2019-06-28