SINTESIS PARASETAMOL DENGAN CARA ASETILASI p-AMINOFENOL MENGGUNKAN ANHIDRIDA ASETAT DAN ASAM ASETAT

Authors

  • Syaiful Prayogi
  • Pudjono Pudjono
  • Eka Trisnawati

Keywords:

p-aminofenol, acethaminophen, asetilasi, anhidrida asetat, asam asetat

Abstract

Almost 90% of the raw materials for drugs in Indonesia are still imported. The total import value in 2018 was the US $ 5 billion. Paracetamol is one of the raw materials for drugs that are still imported. Paracetamol can be prepared by acetylation of p-aminophenol. This study aims to find acetylation that produces optimal products in the synthesis of paracetamol using acetic anhydride, acetic acid, and their mixtures. Synthesis is carried out by reacting p-aminophenol with acetylating compounds at each variation of moles. The synthesized crude is recrystallized using hot distilled water. To determine the purity of the synthesized compound, the TLC test was carried out with distilled water eluent: acetone (6: 4), determination of the melting point, and analysis of the IR spectrophotometer. TLC test results for the synthesis of paracetamol from p-aminophenol and acetic anhydride (experiment I); p-aminophenol and acetic anhydride with acetic acid (experiment III) showed Rf values ​​of 0.88 and 0.88, respectively. Melting point test results 169-173 0C (experiment I) and 168-170 0C (experiment III). The results of the IR spectra of synthesis experiments I and III obtained peak data that were identical to those of pure paracetamol. The most optimal acetylation with the highest yield of 59.5% was obtained from the reaction of p-aminophenol with acetic anhydride using a mole ratio (1: 0.5)

References

1. Antaranews. 90% Bahan baku Obat Indonesia Masih Impor [Internet]. 2015 [dikutip 2019 Mar 10];Available from: https://www.antaranews.com/berita/498410/90-persen-bahan-baku-obat-indonesia-masih-impor
2. Kementerian Kesehatan Republik Indonesia. Grafik Rekapitulasi Industri Farmasi di Indonesia Direktorat Jenderal Kefarmasian dan Alat Kesehatan Kementerian Kesehatan RI [Internet]. 2018 [dikutip 2019 Mar 13];Available from: http://binfar.kemkes.go.id/2018/02/grafik-rekapitulasi-industri-farmasi/
3. Beritasatu.com. Nilai Impor Bahan Baku Obat Tembus Rp 11 Triliun [Internet]. beritasatu.com2012 [dikutip 2019 Mar 10];Available from: https://www.beritasatu.com/kesehatan/35867/nilai-impor-bahan-baku-obat-tembus-rp-11-triliun
4. Pernando A. Begini Cara Pemerintah Tekan Impor Bahan Baku Industri Farmasi [Internet]. 2018 [dikutip 2019 Mar 13];Available from: https://ekonomi.bisnis.com/read/20180823/257/830988/begini-cara-pemerintah-tekan-impor-bahan-baku-industri-farmasi
5. Indonesia PR. Instruksi Presiden Republik Indonesia Nomor 6 Tahun 2016 tentang Percepatan Pengembangan Industri Farmasi dan Alat Kesehatan. 2016;
6. Habibi D, Rahmani P, Akbaripanah Z. Acetylation of Phenols, Anilines, and Thiols Using Silica Sulfuric Acid Under Solvent-free Conditions. Journal of Chemistry 2013;2013:1--6.
7. Olariu T, Suta L, Popoiu C, Ledeti IV, Simu GM, Savoiu-Balint G, dkk. Alternative Synthesis of Paracetamol and Aspirin under Non-conventional Conditions. REV CHIM (Bucharest) 2014;65(6):633--635.
8. Joncour R, Duguet N, Métay E, Ferreira A, Lemaire M. Amidation Of Phenol Derivatives: A Direct Synthesis of Paracetamol (Acetaminophen) from Hydroquinone. Green Chemistry 2014;16(6):2997--3002.
9. Eynde JJ Vanden. How Efficient is My (Medicinal) Chemistry? Pharmaceuticals 2016;9(2):1–16.
10. Fessenden RJ, Fessenden JS. Dasar-Dasar Kimia Organik. Edisi Keti. Jakarta: Erlangga; 1982.
11. Sarwono AEY. Sintesis Asetil Eugenol dari Eugenol dan Anhidrida Asam Asetat dengan Katalis Kalium Hidroksida. 2011;
12. Antasari FA, Iftitah ED, Utomo EP. Studi Sintesis Patchouli Asetat melalui Pembentukan Alkoksida dari Patchouli Alkohol. Indonesian Journal of Essential Oil 2017;2(2):49–58.
13. Sugiyono. Metode Penelitian kuantitatif, kualitatif, dan R&D. Bandung: Alfabeta; 2017.
14. Saifudin A. Senyawa Malam Metabolit Sekunder. 2014.
15. Lestari P. Isolasi dan Identifikasi Komponen kimia Ekstrak Etanol Buah Merah (Pandanus conoideus Lam.). 2011;
16. Furniss BS, Hannaford AJ, Smith PWG, Tatchell AR. Vogel’s Textbook of Practial Organic Chemistry. Fifth Edit. California: Cole Publishing; 1989.
17. Indonesia KKR. Farmakope Indonesia Edisi V. Edisi V. Jakarta: Departemen Kesehatan Republik Indonesia; 2014.
18. Yuliana. Sintesis dan Karakterisasi Senyawa Azo dari p-Aminofenol dengan Sulfanilamida. 2015;
19. Siadi K. Ekstrak Bungkil Biji Jarak (Jatropha curcas) sebagai Biopestisida yang Efektif dengan Penambahan Larutan NaCl. Jurnal MIPA 2012;35(1).

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Published

2022-07-31

How to Cite

Prayogi, S., Pudjono, P., & Trisnawati, E. (2022). SINTESIS PARASETAMOL DENGAN CARA ASETILASI p-AMINOFENOL MENGGUNKAN ANHIDRIDA ASETAT DAN ASAM ASETAT. Pharmacy Peradaban Journal, 2(2), 75–85. Retrieved from https://journal.peradaban.ac.id/index.php/ppj/article/view/1167

Issue

Section

Vol 2 No 1 (2021): Pharmacy Peradaban Journal (Pharm. PJ): Jurnal Farmasi Univer

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