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Abstract
The synthesis of p-t-butylcalix[6]arene (PK[6]A) and calixresorcinarene derivative compounds, namely C-para-dimethylamino-phenylcalix[4]resorcinarene (CPDAK[4]R) and C-4-hydroxy-phenylcalix[4]-resorcinarene (CHK[4]R), had been carried out by grinding technique. The grinding technique was done with the absence of solvents so that it minimized the waste. Synthesis occurred through electrophilic substitution reactions with KOH as an alkaline catalyst and p-toluene sulfonic acid as an acid catalyst. The three calixarene products were in the form of crystalline solids with a melting point of more than 300°C, insoluble in water with yields of 62.58; 61.94 and 97.49%, respectively. Product characterization using FTIR analysis showed the vibration of the methylene bridge (-CH2-) at a wavenumber of 1473.62 cm-1 and LC-MS analysis for (PK[6]R) showed that the molecular weight was 974.77 g/mole. While the analysis of (CPDAK[4]R) and (CHK[4]R) with 1H NMR showed the presence of protons from the methine bridge (-CH-) that appear at the chemical shift of 4.950 and 3.078 ppm.
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References
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References
S.B. Utomo, Rekayasa Molekul Makrosiklis untuk Aplikasi Lingkungan dan Medis. SeminarNasional Kimia dan Pendidikan Kimia VI, Program Studi Pendidikan Kimia Universitas SebelasMaret, Surakarta, 2014.
D.L. Silvia, S.A. Fernandees, A.A. Sabino, A. Fatima, P-Sulfonic Acid Calixarenes as Efficient andReusable Organocatalysts for the Synthesis of 3,4-dihydropyrimidin-2(1H)-ones/-Thiones. Journalhomepage: www.elsevier.com/locate/tetlet . Tetrahedron Letters 52 (2011) 6328-6330.
T. Setyawan, Sintesis Senyawa Tabir Surya Turunan Kaliks[4]resorsinarena Benzofenon dari Vanilin.Tesis, Program Studi S2 Ilmu Kimia UGM: Yogyakarta, 2013.
Mukhlasoh, Sintesis Senyawa p-t-Butil-Heksa-Asamkaliks[6]arena dan Penggunaan nya SebagaiEkstraktan Logam Berat Cr(III). Skripsi, Program Studi Kimia UIN Sunan Kalijaga: Yogyakarta,2014
Suharso, Buhani, dan Tugiono, Pembuatan Senyawa Turunan Kaliksarena Untuk Inhibitor KerakMaterial Anorganik. Prosiding SEMIRATA 2015 Bidang MIPA BKS-PTN Barat: UniversitasTanjungpura, Pontianak, 2015.
F.N. Hanifa, Sintesis Senyawa p-t-Butil-heksa-esterkaliks[6]arena dan Penggunaannya SebagaiEkstraktan Logam Berat Cr(III), Skripsi, Program Studi Kimia UIN Sunan Kalijaga Yogyakarta,2013
A. Setiawan, Sintesis Senyawa C-Heptil Kaliks[4]resorsinaren Oktaasetat dan Aplikasinya SebagaiAdsorben Ion Logam Berat Cr(III), Skripsi, Program Studi Kimia UIN Sunan Kaliijaga: Yogyakarta,2016
S.Y. Prabawati, Jumina, S.J. Santosa, Mustofa, O. Keisuke, Study on the Adsorption Properties ofNovel Calix[6]arene Polymers for Heavy Metal Cations, Indo. J. Chem. 12 (1) (2012) 28-34.
J.L. Atwood, Solvent-Free, Direct Synthesis of Supramolecular Nano-Capsules, Chem. Commun.The Royal Society of Chemistry, 892-894, 2005.
R.E. Sardjono, R. Rahmi, Green Sythesis of Oligomer Calixarenes. Pada buku: Green ChemicalProcessing and Synthesis. Diedit oleh Karame, Iyad and Hassan Srour. Publisher: InTech, 2017
B.A. Robert, W.V. Gareth, C.L. Raston, J.L Scoot, Solvent-Free Synthesis of Calix[4]recorciarenes.Green Chemistry. The Royal Society of Chemistry, (3) (2001) 280-284.
S. Santra, Solvent-free Synthesis of Pillar[6]arenes, Green Chemistry, The Royal Society ofChemistry, 2015.
S. Sobariah, Penggunaan Metode Solvent-Free Pada Sintesis Tetramer Siklik Kaliks[4]resorsinarenadari 7-Hidroksisitronelal, Skripsi, FMIPA UPI, 2011.
C.D. Gutsche, Calixarenes: An Introduction 2nd Edition. Cambridge: The Royal Society ofChemistry, 2008.
S.Y. Prabawati, Jumina, S.J. Santosa, Mustofa, Synthesis of Polypropylcalix[6]arene from p-t-butylphenol as Adsorbent for Cr(III) Metal Ion, Indo. J. Chem. 11 (1) (2011) 37-42.
D.S. Handayani, R.A. Sholikh, T. Kusumaningsih, Sintesis dan Karakterisasi C-4-hidroksi-3-metoksifenilKaliks[4]-resorsinarena Sulfonat, Alchemy Jurnal Penelitian Kimia, 9 (2) (2013) 13-21.
R.E. Sardjono, Sintesis dan Penggunaan Tetramer Siklis Seri Kaliksresorsinarena,Alkoksikaliksarena, dan Alkenimaliksarena Untuk Adsorpsi Kation Logam Berat. Disertasi,Universitas Gajah Mada: Yogyakarta, 2007.
Pubchem, Compound Summary: 4-tert-butylcalix[6]arene. //https: pubchem.ncbi.nlm.nih.gov/compound/335356#section=lnChl-Key, 2019
H. Sastrohamidjojo, Spektroskopi, Yogyakarta: Liberty, 2007.