Pb^"" > Cd^"" (83,8% : 74,8% : 43,9%), senyawa la adalah Pb^"^ > > Cr^^ (15,0% : 13,2% : 11,4%), senyawa 2 adalah Pb^"" > Cd^"" > Cr^"" (86,2% : 47,2% : 11,6), senyawa 3 adalah Pb^"*^ > > Cd^"^ (50,0% : 42,9% : 22,8), senyawa 4 adalah Pb ^ > Cr^^ > Cd^^ (74,4% : 46,6% : 24,7%), dan senyawa 6 adalah Cd^^ > Pb^"^ > Cr^"*" (35,3% : 30,7% : 21,3%). Faktor pemisahan yang paling tinggi diperlihatkan oleh senyawa 2 untuk ion Pb^^ d^ Cr^^ dengan nilai p 48,0. Mekanisme ekstraksi ion logam berat Cr^"*", Cd^"*^, and Pb^^ dengan senyawasenyawa kaliks[4]arena tersebut telah ditetapkan. Kata kunci: p-aminokaliks[4]arena, p-(amino)butoksikaliks[4]arena,/?-(asetamido) butoksikaliks[4]arena, p-(benzamido)butoksikaliks[4]arena p-(karboksimetilamino)butoksikaliks[4]arena, p-(etoksik^bonilmetilamino) butoksikaliks[4]arena, konformasi, ekstraksi, logam berat This dissertation includes the synthetic methods of amine, amide, aminoacetic acid, and ethyl aminoacetate derivatives of calix[4]arene; 5,11,17,23- tetraamino-25,26,27,28-tetrahydroxycaiix[4]arene (1), 5,11,17,23-tetraamino- 25,26,27,28-tetrabutoxycalix[4]arene (2), 5,1 l,17,23-tet^aacetamido-25,26,27,28- tetrabutoxycalix[4]arene (3), 5,1 l,17,23-tetrabenzamido-25,26,27,28-tetrabutoxycalix[ 4]arene (4), 5,1 l,17,23-tetrakis(carboxymethylamino)-25,26,27,28-tetrabutoxycaliks[ 4]arene (5), and 5,1 l,17,23-tetrakis-(2'-ethoxy-2'-oxoethylamino)- 25,26,27,28-tetrabutoxycalix[4]arena (6); characterization and determination of their confonnation; study of their extractability towards Cr^"*^, Cd^^, and Pb^"^ heavy metals ions as well as mechanisms of the extraction; and the influence of upper rim groups to the extractability. Amine and amide derivatives of calix[4]arene were selected as the target compounds based on the consideration that their basicity are theoretically suitable to the acidity of heavy metals ions. Determination of the synthetic methods were performed by re/ro-synthetic analysis and reaction condition study; characterization of these compounds were carried out using melting point and Rf values on TLC, and by IR, 'H-NMR, '^CNMR, and MS spectroscopic methods, and their conformation were studied by *H-NMR spectral analysis. The extractability of the synthesized calix[4]arenes to Cr'^, Cd^^, and Pb^^ heavy metals ions as well as the influence of upper rim groups of calix[4]arene compounds to the extractability have been studied which involve pH, time, and extractant concentration parameters; and the extraction mechanisms have been studied by slope analysis of the linear plots obtained from plotting of extraction degree against pH as well as extractant concentration correlations. Within this research, compound 1 was synthesized via de-/-butyIation of compound i using AICI3 in toluene to give 25,26,27,28-tetrahydroxycalix[4]arene (la) in 72.1% yield; nitration of compound la using nitric acid 65% and a solvent mixture of benzene-glacial acetic acid gave 5,1 l,17,23-tetranitro-25,26,27,28- tetrahydroxy-calix[4]arene (lb) in 66.4% yield; and reduction of compound lb using zinc dust, hydrazine, and formic acid in methanol afforded compound 1 in 62.5% yield. Compound 2 was synthesized via etherification of compound i using l-bromobutane/Nal reagent, NaH as the base and a solvent mixture of dry THF DMF (10:1) to give partial cone conformer of 5,ll,17,23-tetra-/er/-butyl- 25,26,27,28-tetrabutoxycalix[4]arene (2a) in 84.2% yield; ipso nitration of compound 2a using excess HNO3 100% reagent and a solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) gave partial cone conformer of 5,ll,17,23-tetranitro-25,26,27,28-tetrabutoxycalix[4]arene (2b) in 50.0% yield; and reduction of compound 2b using SnCl2/HCl reductor in ethanol gave partial cone conformer of compound 2 in 68.2% yield. Compound 3 was synthesized via acetylation of compound 2 using excess acetyl chloride in dry toluene-pyridine to give partial cone conformer of compound 3 in 97.9% yield. By the same method and using benzoyl chloride, compound 4 was obtained in 67.1% yield. Compound 5 was obtained in 53.9% yield via substitution reaction of compound 2 using chloroacetic acid/Nal reagent and 10% alcoholic NaOH solution as the base in chloroform; and compound 6 was obtained in 33.5% yield via substitution reaction of comiwund 2 using ethyl chloroacetate and K2CO3 as the base in ethanol. The ^application of compound i, la, 2, 3, 4, and 6 as extractant for Cr^^, Cd , and Pb ^ ions showed that the upper rim groups remarkably influence to the extractability of calix[4]arene compounds to the heavy metals ions; the existence of amine, amide, and carboxymethylamine ester groups at upper rim of calix[4]arene can be used as ionophore for heavy metals ions. The extractability order of compound i was Cr^"" > Pb^"^ > Cd^"" (83.8% : 74.8% : 43.9%), compound la w^ Pb" > Cd'^ > Cr^"- (15.0% : 13.2%: 11.4%), compound 2 was Pb^^ > Cd'^ > Cr^ (86.2% : 47.2% : 11.6%), compound 3 was Pb^^ > Cr^^ > Cd^^ (50.0% : 42.9% : 22.8), compound 4 was Pb^"" > Cr^^ > Cd^^ (74.4% : 46.6% : 24.7%) and compound 6 was Cd'"^ > Pb'^ > Cr^^ (35.3% : 30.7% : 21.3%). Compound 2 showed highest separation factor (fi) for Pb^^ and Cr^"" ions with p value of 48.0. The extraction mechanisms of Cr^"^, Cd^"^, and Pb^^ metals ions by H \ calix[4]arene derivatives have been confirmed. Keywords: />-aminocalix[4]arene, /?-(amino)butoxycalix[4]arene, j?-(acetamido)- butoxycaIix[4]arene, />-(benzamido)butoxycaIix[4]arene, p-(carboxymethylammo) butoxycalix[4]arene,p-(ethoxycarbonylmethylamino)- butoxycalix[4]arene, conformation, extraction, heavy metals"> Pb^"" > Cd^"" (83,8% : 74,8% : 43,9%), senyawa la adalah Pb^"^ > > Cr^^ (15,0% : 13,2% : 11,4%), senyawa 2 adalah Pb^"" > Cd^"" > Cr^"" (86,2% : 47,2% : 11,6), senyawa 3 adalah Pb^"*^ > > Cd^"^ (50,0% : 42,9% : 22,8), senyawa 4 adalah Pb ^ > Cr^^ > Cd^^ (74,4% : 46,6% : 24,7%), dan senyawa 6 adalah Cd^^ > Pb^"^ > Cr^"*" (35,3% : 30,7% : 21,3%). Faktor pemisahan yang paling tinggi diperlihatkan oleh senyawa 2 untuk ion Pb^^ d^ Cr^^ dengan nilai p 48,0. Mekanisme ekstraksi ion logam berat Cr^"*", Cd^"*^, and Pb^^ dengan senyawasenyawa kaliks[4]arena tersebut telah ditetapkan. Kata kunci: p-aminokaliks[4]arena, p-(amino)butoksikaliks[4]arena,/?-(asetamido) butoksikaliks[4]arena, p-(benzamido)butoksikaliks[4]arena p-(karboksimetilamino)butoksikaliks[4]arena, p-(etoksik^bonilmetilamino) butoksikaliks[4]arena, konformasi, ekstraksi, logam berat This dissertation includes the synthetic methods of amine, amide, aminoacetic acid, and ethyl aminoacetate derivatives of calix[4]arene; 5,11,17,23- tetraamino-25,26,27,28-tetrahydroxycaiix[4]arene (1), 5,11,17,23-tetraamino- 25,26,27,28-tetrabutoxycalix[4]arene (2), 5,1 l,17,23-tet^aacetamido-25,26,27,28- tetrabutoxycalix[4]arene (3), 5,1 l,17,23-tetrabenzamido-25,26,27,28-tetrabutoxycalix[ 4]arene (4), 5,1 l,17,23-tetrakis(carboxymethylamino)-25,26,27,28-tetrabutoxycaliks[ 4]arene (5), and 5,1 l,17,23-tetrakis-(2'-ethoxy-2'-oxoethylamino)- 25,26,27,28-tetrabutoxycalix[4]arena (6); characterization and determination of their confonnation; study of their extractability towards Cr^"*^, Cd^^, and Pb^"^ heavy metals ions as well as mechanisms of the extraction; and the influence of upper rim groups to the extractability. Amine and amide derivatives of calix[4]arene were selected as the target compounds based on the consideration that their basicity are theoretically suitable to the acidity of heavy metals ions. Determination of the synthetic methods were performed by re/ro-synthetic analysis and reaction condition study; characterization of these compounds were carried out using melting point and Rf values on TLC, and by IR, 'H-NMR, '^CNMR, and MS spectroscopic methods, and their conformation were studied by *H-NMR spectral analysis. The extractability of the synthesized calix[4]arenes to Cr'^, Cd^^, and Pb^^ heavy metals ions as well as the influence of upper rim groups of calix[4]arene compounds to the extractability have been studied which involve pH, time, and extractant concentration parameters; and the extraction mechanisms have been studied by slope analysis of the linear plots obtained from plotting of extraction degree against pH as well as extractant concentration correlations. Within this research, compound 1 was synthesized via de-/-butyIation of compound i using AICI3 in toluene to give 25,26,27,28-tetrahydroxycalix[4]arene (la) in 72.1% yield; nitration of compound la using nitric acid 65% and a solvent mixture of benzene-glacial acetic acid gave 5,1 l,17,23-tetranitro-25,26,27,28- tetrahydroxy-calix[4]arene (lb) in 66.4% yield; and reduction of compound lb using zinc dust, hydrazine, and formic acid in methanol afforded compound 1 in 62.5% yield. Compound 2 was synthesized via etherification of compound i using l-bromobutane/Nal reagent, NaH as the base and a solvent mixture of dry THF DMF (10:1) to give partial cone conformer of 5,ll,17,23-tetra-/er/-butyl- 25,26,27,28-tetrabutoxycalix[4]arene (2a) in 84.2% yield; ipso nitration of compound 2a using excess HNO3 100% reagent and a solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) gave partial cone conformer of 5,ll,17,23-tetranitro-25,26,27,28-tetrabutoxycalix[4]arene (2b) in 50.0% yield; and reduction of compound 2b using SnCl2/HCl reductor in ethanol gave partial cone conformer of compound 2 in 68.2% yield. Compound 3 was synthesized via acetylation of compound 2 using excess acetyl chloride in dry toluene-pyridine to give partial cone conformer of compound 3 in 97.9% yield. By the same method and using benzoyl chloride, compound 4 was obtained in 67.1% yield. Compound 5 was obtained in 53.9% yield via substitution reaction of compound 2 using chloroacetic acid/Nal reagent and 10% alcoholic NaOH solution as the base in chloroform; and compound 6 was obtained in 33.5% yield via substitution reaction of comiwund 2 using ethyl chloroacetate and K2CO3 as the base in ethanol. The ^application of compound i, la, 2, 3, 4, and 6 as extractant for Cr^^, Cd , and Pb ^ ions showed that the upper rim groups remarkably influence to the extractability of calix[4]arene compounds to the heavy metals ions; the existence of amine, amide, and carboxymethylamine ester groups at upper rim of calix[4]arene can be used as ionophore for heavy metals ions. The extractability order of compound i was Cr^"" > Pb^"^ > Cd^"" (83.8% : 74.8% : 43.9%), compound la w^ Pb" > Cd'^ > Cr^"- (15.0% : 13.2%: 11.4%), compound 2 was Pb^^ > Cd'^ > Cr^ (86.2% : 47.2% : 11.6%), compound 3 was Pb^^ > Cr^^ > Cd^^ (50.0% : 42.9% : 22.8), compound 4 was Pb^"" > Cr^^ > Cd^^ (74.4% : 46.6% : 24.7%) and compound 6 was Cd'"^ > Pb'^ > Cr^^ (35.3% : 30.7% : 21.3%). Compound 2 showed highest separation factor (fi) for Pb^^ and Cr^"" ions with p value of 48.0. The extraction mechanisms of Cr^"^, Cd^"^, and Pb^^ metals ions by H \ calix[4]arene derivatives have been confirmed. Keywords: />-aminocalix[4]arene, /?-(amino)butoxycalix[4]arene, j?-(acetamido)- butoxycaIix[4]arene, />-(benzamido)butoxycaIix[4]arene, p-(carboxymethylammo) butoxycalix[4]arene,p-(ethoxycarbonylmethylamino)- butoxycalix[4]arene, conformation, extraction, heavy metals">
Sintesis turunan Amina, Amida, Asam Aminoasetat, dan Ester Etil Aminoasetat Kaliks[4]Arena serta penggunaannya sebagai ekstraktan ion logam berat Cr3+, Cd2+, dan Pb2+
FIRDAUS, Promotor Prof.Dr. Hardjono Sastrohamidjojo
2007 | Disertasi | S3 Ilmu KimiaDisertasi ini meliputi metode sintesis turunan amina, amida, asam aminoasetat, dan ester etil aminoasetat kaliks[4]arena: 5,11,17,23-tetraamino-25,26,27,28-tetrahidroksikaliks[4]arena (1), 5,11,17,23-tetraamino-25,26,27,28-tetrabutoksikaliks[4]arena (2), 5,Il,17,23-tetraasetamido-25,26,27,28-tetrabutoksikaliks[4]arena (3), 5,11,17,23-tetrabenzamido-25,26,27,28-tetrabutoksikaiiks[4]arena (4), 5,ll,17,23-tetrakis(karboksimetilamino)-25,26,27,28-tetrabutoksikaliks[4]arena (5), dan 5,ll,17,23-tetrakis(2'-etoksi-2'-oksoetilamino)-25,26,27,28-tetrabutoksikaliks[4]arena (6) dari senyawa 5,11,17,23-tetra-I-butil-25,26,27,28-tetrahidroksikaliks[4]arena (i); karakterisasi, konformasi dan ekstraktabilitasnya terhadap ion logam berat Cr^, Cd^"^, dan Pb^"^; serta studi pengaruh gugus atas cincin kaliks[4]arena terhadap ekstraktabilitas dan mekanisme ekstraksinya, Senyawa-senyawa turunan amina dan amida kaliks[4]arena tersebut dipilih sebagai senyawa target dengan pertimbangan bahwa sifat kebasaannya secara teoritis sesuai dengan sifat keasaman ion-ion logam berat. Metode sintesis dipelajari melalui rancangan dengan menggunakan metode analisis re/ro-sintesis dan kondisi reaksi; karakterisasi hasil sintesis dilakukan melalui t.I., nilai Rf pada KET, metode spektroskopi IR, 'H-NMR, '^C-NMR, serta MS; dan konformasinya ditentukan dengan metode analisis spektrum 'HNMR. Ekstraktabilitas senyawa target terhadap ion logam berat Cr^^, Cd^^, dan Pb^^ dan pengaruh gugus atas cincin senyawa kaliks[4]arena terhadap ekstraktabilitas dipelajari dengan melibatkan parameter pH, waktu, serta konsentrasi ekstraktan; dan mekanisme ekstraksi ditentukan dengan metode analisis kemiringan garis linear grafik hubungan antara persentase ekstraksi dengan parameter pH serta konsentrasi ekstraktan, Melalui penelitian yang telah dilakukan maka senyawa 1 telah dapat disintesis melalui urutan reaksi de-/-butilasi terhad^ senyawa i menggunakan pereaksi AICI3 dan pelarut toluena kering mengh^ilkan 25,26,27,28- tetrahidroksikaliks[4]arena (la) dengan rendemen 72,1%, nitrasi senyawa la menggunakan HNO3 65% dan campuran pelarut benzena-asam asetat glasial menjadi 5,ll,I7,23-tetranitro-25,26,27,28-tetrahidroksikaliks[4]arena (lb) dengan rendemen 66,4%, dan reduksi senyawa lb menggunakan Zn/hidrazinium monoformat dan pelarut metanol menjadi senyawa 1 dengan rendemen 62,5%. Senyawa 2 dapat disintesis melalui urutan reaksi eterifikasi senyawa i menggunakan pereaksi 1-bromobutana/NaI, basa NaH, dan campuran pelarut THF-DMF kering (10:1 v/v) menghasilkan konformer partial cone 5,11,17,23- tetra-/-butil-25,26,27,28-tetrabutoksikaIiks[4]arena (2a) dengan rendemen 84,2%, ipso nitrasi senyawa 2a menggunakan pereaksi HNO3 100% dan campuran pelarut diklorometana-asam asetat glasial (1:1 v/v) menghasilkan konformer partial cone 5,ll,17,23-tetranitro-25,26,27,28-tetrabutoksikaliks[4]arena (2b) dengan rendemen 50,0%, dan reduksi senyawa 2b menggunakan SnCl2/HCl dan pelarut etanol menghasilkan senyawa 2 dengan rendemen 68,2%. Senyawa 3 dengan rendemen 97,9% dan senyawa 4 dengan rendemen 67,1% masing-masing diperoleh melalui reaksi asetilasi dan benzoilasi terhadap senyawa 2 menggunakan pereaksi asetil klorida dan benzoil klorida di dalam pelarut toluena kering dan sedikit piridin. Senyawa 5 dengan rendemen 53,9% diperoleh melalui reaksi substitusi senyawa 2 menggunakan pereaksi asam kloroasetat/Nal, NaOH 10% dalam pelarut etanol sebagai basa, dan pelarut kloroform. Dengan reaksi yang sama terhadap senyawa 2 dan menggunakan pereaksi etil kloroasetat/Nal, basa K2CO3, dan pelarut etanol diperoleh senyawa 6 dengan rendemen 33,5%. Hasil penerapan senyawa-senyawa i, la, 2, 3, 4, dan 6 sebagai ekstraktan ion logam berat Cr^^, Cd^^, and Pb^^ memperlihatkan bahwa gugus atas cincin kaliks[4]arena sangat mempengaruhi ekstraktabilitas senyawa-senyawa kaliks[4]arena terhadap ion-ion logam berat tersebut. Keberadaan gugus amina, amida, ester karboksimetilamina pada bagian atas cincin dapat berfungsi sebagai ionofor untuk ion-ion logam berat. Urutan ekstraktabilitas senyawa i adalah Cr^^ > Pb^"" > Cd^"" (83,8% : 74,8% : 43,9%), senyawa la adalah Pb^"^ > > Cr^^ (15,0% : 13,2% : 11,4%), senyawa 2 adalah Pb^"" > Cd^"" > Cr^"" (86,2% : 47,2% : 11,6), senyawa 3 adalah Pb^"*^ > > Cd^"^ (50,0% : 42,9% : 22,8), senyawa 4 adalah Pb ^ > Cr^^ > Cd^^ (74,4% : 46,6% : 24,7%), dan senyawa 6 adalah Cd^^ > Pb^"^ > Cr^"*" (35,3% : 30,7% : 21,3%). Faktor pemisahan yang paling tinggi diperlihatkan oleh senyawa 2 untuk ion Pb^^ d^ Cr^^ dengan nilai p 48,0. Mekanisme ekstraksi ion logam berat Cr^"*", Cd^"*^, and Pb^^ dengan senyawasenyawa kaliks[4]arena tersebut telah ditetapkan. Kata kunci: p-aminokaliks[4]arena, p-(amino)butoksikaliks[4]arena,/?-(asetamido) butoksikaliks[4]arena, p-(benzamido)butoksikaliks[4]arena p-(karboksimetilamino)butoksikaliks[4]arena, p-(etoksik^bonilmetilamino) butoksikaliks[4]arena, konformasi, ekstraksi, logam berat
This dissertation includes the synthetic methods of amine, amide, aminoacetic acid, and ethyl aminoacetate derivatives of calix[4]arene; 5,11,17,23- tetraamino-25,26,27,28-tetrahydroxycaiix[4]arene (1), 5,11,17,23-tetraamino- 25,26,27,28-tetrabutoxycalix[4]arene (2), 5,1 l,17,23-tet^aacetamido-25,26,27,28- tetrabutoxycalix[4]arene (3), 5,1 l,17,23-tetrabenzamido-25,26,27,28-tetrabutoxycalix[ 4]arene (4), 5,1 l,17,23-tetrakis(carboxymethylamino)-25,26,27,28-tetrabutoxycaliks[ 4]arene (5), and 5,1 l,17,23-tetrakis-(2'-ethoxy-2'-oxoethylamino)- 25,26,27,28-tetrabutoxycalix[4]arena (6); characterization and determination of their confonnation; study of their extractability towards Cr^"*^, Cd^^, and Pb^"^ heavy metals ions as well as mechanisms of the extraction; and the influence of upper rim groups to the extractability. Amine and amide derivatives of calix[4]arene were selected as the target compounds based on the consideration that their basicity are theoretically suitable to the acidity of heavy metals ions. Determination of the synthetic methods were performed by re/ro-synthetic analysis and reaction condition study; characterization of these compounds were carried out using melting point and Rf values on TLC, and by IR, 'H-NMR, '^CNMR, and MS spectroscopic methods, and their conformation were studied by *H-NMR spectral analysis. The extractability of the synthesized calix[4]arenes to Cr'^, Cd^^, and Pb^^ heavy metals ions as well as the influence of upper rim groups of calix[4]arene compounds to the extractability have been studied which involve pH, time, and extractant concentration parameters; and the extraction mechanisms have been studied by slope analysis of the linear plots obtained from plotting of extraction degree against pH as well as extractant concentration correlations. Within this research, compound 1 was synthesized via de-/-butyIation of compound i using AICI3 in toluene to give 25,26,27,28-tetrahydroxycalix[4]arene (la) in 72.1% yield; nitration of compound la using nitric acid 65% and a solvent mixture of benzene-glacial acetic acid gave 5,1 l,17,23-tetranitro-25,26,27,28- tetrahydroxy-calix[4]arene (lb) in 66.4% yield; and reduction of compound lb using zinc dust, hydrazine, and formic acid in methanol afforded compound 1 in 62.5% yield. Compound 2 was synthesized via etherification of compound i using l-bromobutane/Nal reagent, NaH as the base and a solvent mixture of dry THF DMF (10:1) to give partial cone conformer of 5,ll,17,23-tetra-/er/-butyl- 25,26,27,28-tetrabutoxycalix[4]arene (2a) in 84.2% yield; ipso nitration of compound 2a using excess HNO3 100% reagent and a solvent mixture of dichloromethane-acetic acid glacial (1:1 v/v) gave partial cone conformer of 5,ll,17,23-tetranitro-25,26,27,28-tetrabutoxycalix[4]arene (2b) in 50.0% yield; and reduction of compound 2b using SnCl2/HCl reductor in ethanol gave partial cone conformer of compound 2 in 68.2% yield. Compound 3 was synthesized via acetylation of compound 2 using excess acetyl chloride in dry toluene-pyridine to give partial cone conformer of compound 3 in 97.9% yield. By the same method and using benzoyl chloride, compound 4 was obtained in 67.1% yield. Compound 5 was obtained in 53.9% yield via substitution reaction of compound 2 using chloroacetic acid/Nal reagent and 10% alcoholic NaOH solution as the base in chloroform; and compound 6 was obtained in 33.5% yield via substitution reaction of comiwund 2 using ethyl chloroacetate and K2CO3 as the base in ethanol. The ^application of compound i, la, 2, 3, 4, and 6 as extractant for Cr^^, Cd , and Pb ^ ions showed that the upper rim groups remarkably influence to the extractability of calix[4]arene compounds to the heavy metals ions; the existence of amine, amide, and carboxymethylamine ester groups at upper rim of calix[4]arene can be used as ionophore for heavy metals ions. The extractability order of compound i was Cr^"" > Pb^"^ > Cd^"" (83.8% : 74.8% : 43.9%), compound la w^ Pb" > Cd'^ > Cr^"- (15.0% : 13.2%: 11.4%), compound 2 was Pb^^ > Cd'^ > Cr^ (86.2% : 47.2% : 11.6%), compound 3 was Pb^^ > Cr^^ > Cd^^ (50.0% : 42.9% : 22.8), compound 4 was Pb^"" > Cr^^ > Cd^^ (74.4% : 46.6% : 24.7%) and compound 6 was Cd'"^ > Pb'^ > Cr^^ (35.3% : 30.7% : 21.3%). Compound 2 showed highest separation factor (fi) for Pb^^ and Cr^"" ions with p value of 48.0. The extraction mechanisms of Cr^"^, Cd^"^, and Pb^^ metals ions by H \ calix[4]arene derivatives have been confirmed. Keywords: />-aminocalix[4]arene, /?-(amino)butoxycalix[4]arene, j?-(acetamido)- butoxycaIix[4]arene, />-(benzamido)butoxycaIix[4]arene, p-(carboxymethylammo) butoxycalix[4]arene,p-(ethoxycarbonylmethylamino)- butoxycalix[4]arene, conformation, extraction, heavy metals
Kata Kunci : Metode Sintesis,Ekstraksi,Logam Berat