Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate
Pojednostavljenje postupka sinteze raft agensa 2-(2-cijanopropil)-ditiobenzoata
2010
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The general literature procedure for the preparation of the reversible addition-fragmentation chain transfer (RAFT) agent 2-(2-cyanopropyl)-dithiobenzoate (CPDB) was modified by omitting the recrystallisation of the intermediate di(thiobenzoyl)disulphide. The yield of the CPDB in the simplified synthesis was increased four times compared to the standard one. The behaviour of the CPDB obtained by the modified procedure and by the standard one in the polymerisation of methyl methacrylate was investigated. The CPDB synthesized by the simplified procedure showed itself to be a good RAFT agent, giving excellent control over the polymerisation of methyl methacrylate and it behaved in the same manner as the CPDB prepared by the literature method. The obtained poly(methyl methacrylate) had a narrow molecular weight distibution (PD = 1.1).
Standardni postupak sinteze 2-(2-cijanopropil)-ditiobenzoata (CPDB) agensa iz literature za RAFT polimerizaciju, odnosno za reverzibilnu adiciono-fragmentacionu transfer polimerizaciju, je modifikovan izostavljanjem prekristalizacije međuproizvoda bis-(tiobenzoil)disulfida. Prinos CPDB-a sintetisanog pojednostavljenim postupkom je četiri puta veći u odnosu na prinos CPDB-a sintetisanog standardnim postupkom. Ispitano je ponašanje CPDB-a dobijenog modifikovanim i onog dobijenog standardnim postupkom u polimerizaciji metil metakrilata. CPDB dobijen pojednostavljenim postupkom pokazao se kao dobar RAFT agens koji uspostavlja odličnu kontrolu polimerizacije metil metakrilata i koji se ponaša na isti način kao CPDB sintetisan standardnim postupkom. Dobijeni poli(metil metakrilat) ima usku širinu raspodele molskih masa (PD = 1.1).
Ključne reči:
2-(2-cyanopropyl)-dithiobenzoate / preparation / reversible addition-fragmentation chain transfer / poly(methyl methacrylate)Izvor:
Journal of the Serbian Chemical Society, 2010, 75, 12, 1711-1719Izdavač:
- Serbian Chemical Society, Belgrade
Finansiranje / projekti:
- Sinteza i karakterizacija polimera i polimernih (nano)kompozita definisane molekulske i nadmolekulske strukture (RS-MESTD-MPN2006-2010-142023)
Institucija/grupa
Tehnološko-metalurški fakultetTY - JOUR AU - Milovanović, Miloš B. AU - Avramović, Milena AU - Katsikas, Lynne AU - Popović, Ivanka PY - 2010 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1594 AB - The general literature procedure for the preparation of the reversible addition-fragmentation chain transfer (RAFT) agent 2-(2-cyanopropyl)-dithiobenzoate (CPDB) was modified by omitting the recrystallisation of the intermediate di(thiobenzoyl)disulphide. The yield of the CPDB in the simplified synthesis was increased four times compared to the standard one. The behaviour of the CPDB obtained by the modified procedure and by the standard one in the polymerisation of methyl methacrylate was investigated. The CPDB synthesized by the simplified procedure showed itself to be a good RAFT agent, giving excellent control over the polymerisation of methyl methacrylate and it behaved in the same manner as the CPDB prepared by the literature method. The obtained poly(methyl methacrylate) had a narrow molecular weight distibution (PD = 1.1). AB - Standardni postupak sinteze 2-(2-cijanopropil)-ditiobenzoata (CPDB) agensa iz literature za RAFT polimerizaciju, odnosno za reverzibilnu adiciono-fragmentacionu transfer polimerizaciju, je modifikovan izostavljanjem prekristalizacije međuproizvoda bis-(tiobenzoil)disulfida. Prinos CPDB-a sintetisanog pojednostavljenim postupkom je četiri puta veći u odnosu na prinos CPDB-a sintetisanog standardnim postupkom. Ispitano je ponašanje CPDB-a dobijenog modifikovanim i onog dobijenog standardnim postupkom u polimerizaciji metil metakrilata. CPDB dobijen pojednostavljenim postupkom pokazao se kao dobar RAFT agens koji uspostavlja odličnu kontrolu polimerizacije metil metakrilata i koji se ponaša na isti način kao CPDB sintetisan standardnim postupkom. Dobijeni poli(metil metakrilat) ima usku širinu raspodele molskih masa (PD = 1.1). PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate T1 - Pojednostavljenje postupka sinteze raft agensa 2-(2-cijanopropil)-ditiobenzoata EP - 1719 IS - 12 SP - 1711 VL - 75 UR - https://hdl.handle.net/21.15107/rcub_technorep_1594 ER -
@article{ author = "Milovanović, Miloš B. and Avramović, Milena and Katsikas, Lynne and Popović, Ivanka", year = "2010", abstract = "The general literature procedure for the preparation of the reversible addition-fragmentation chain transfer (RAFT) agent 2-(2-cyanopropyl)-dithiobenzoate (CPDB) was modified by omitting the recrystallisation of the intermediate di(thiobenzoyl)disulphide. The yield of the CPDB in the simplified synthesis was increased four times compared to the standard one. The behaviour of the CPDB obtained by the modified procedure and by the standard one in the polymerisation of methyl methacrylate was investigated. The CPDB synthesized by the simplified procedure showed itself to be a good RAFT agent, giving excellent control over the polymerisation of methyl methacrylate and it behaved in the same manner as the CPDB prepared by the literature method. The obtained poly(methyl methacrylate) had a narrow molecular weight distibution (PD = 1.1)., Standardni postupak sinteze 2-(2-cijanopropil)-ditiobenzoata (CPDB) agensa iz literature za RAFT polimerizaciju, odnosno za reverzibilnu adiciono-fragmentacionu transfer polimerizaciju, je modifikovan izostavljanjem prekristalizacije međuproizvoda bis-(tiobenzoil)disulfida. Prinos CPDB-a sintetisanog pojednostavljenim postupkom je četiri puta veći u odnosu na prinos CPDB-a sintetisanog standardnim postupkom. Ispitano je ponašanje CPDB-a dobijenog modifikovanim i onog dobijenog standardnim postupkom u polimerizaciji metil metakrilata. CPDB dobijen pojednostavljenim postupkom pokazao se kao dobar RAFT agens koji uspostavlja odličnu kontrolu polimerizacije metil metakrilata i koji se ponaša na isti način kao CPDB sintetisan standardnim postupkom. Dobijeni poli(metil metakrilat) ima usku širinu raspodele molskih masa (PD = 1.1).", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate, Pojednostavljenje postupka sinteze raft agensa 2-(2-cijanopropil)-ditiobenzoata", pages = "1719-1711", number = "12", volume = "75", url = "https://hdl.handle.net/21.15107/rcub_technorep_1594" }
Milovanović, M. B., Avramović, M., Katsikas, L.,& Popović, I.. (2010). Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 75(12), 1711-1719. https://hdl.handle.net/21.15107/rcub_technorep_1594
Milovanović MB, Avramović M, Katsikas L, Popović I. Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate. in Journal of the Serbian Chemical Society. 2010;75(12):1711-1719. https://hdl.handle.net/21.15107/rcub_technorep_1594 .
Milovanović, Miloš B., Avramović, Milena, Katsikas, Lynne, Popović, Ivanka, "Simplification of the synthesis of the reversible addition-fragmentation chain transfer agent 2-(2-cyanopropyl)-dithiobenzoate" in Journal of the Serbian Chemical Society, 75, no. 12 (2010):1711-1719, https://hdl.handle.net/21.15107/rcub_technorep_1594 .