82208-43-3Relevant articles and documents
Catalytic upcycling of PVC waste-derived phthalate esters into safe, hydrogenated plasticizers
Bals, Sara,De Vos, Dirk E.,Diefenhardt, Thomas,Jain, Noopur,Marquez, Carlos,Schlummer, Martin,Windels, Simon
supporting information, p. 754 - 766 (2022/02/02)
Recycling of end-of-life polyvinyl chloride (PVC) calls for solutions to deal with the vast amounts of harmful phthalate plasticizers that have historically been incorporated in PVC. Here, we report on the upcycling of such waste-extracted phthalate esters into analogues of the much safer diisononyl 1,2-cyclohexanedicarboxylate plasticizer (DINCH), via a catalytic one-pot (trans)esterification-hydrogenation process. For most of the virgin phthalates, Ru/Al2O3 is a highly effective hydrogenation catalyst, yielding >99% ring-hydrogenated products under mild reaction conditions (0.1 mol% Ru, 80 °C, 50 bar H2). However, applying this reaction to PVC-extracted phthalates proved problematic, (1) as benzyl phthalates are hydrogenolyzed to benzoic acids that inhibit the Ru-catalyst, and (2) because impurities in the plasticizer extract (PVC, sulfur) further retard the hydrogenation. These complications were solved by coupling the hydrogenation to an in situ (trans)esterification with a higher alcohol, and by pretreating the extract with an activated carbon adsorbent. In this way, a real phthalate extract obtained from post-consumer PVC waste was eventually completely (>99%) hydrogenated to phthalate-free, cycloaliphatic plasticizers. This journal is
Di[(R)-2-ethylhexyl] phthalate, a bioactive metabolite first isolated from three different bacillus species, and its synthesis
Castro, Miriam,Jiménez, Jacqueline,Ortiz, Aurelio,Sansinenea, Estibaliz
, p. 90 - 95 (2020/02/04)
Di(2-ethylhexyl) phthalate (DEHP) is the most common phthalate ester, which has been used as a plasticizer for the production of numerous polymers, particularly polyvinyl chloride (PVC). Many other groups have synthesized meso-DEHP indicating interest in this molecule, but we are the first to synthesize enantiomerically pure di[(R)-2-ethylhexyl] phthalate. We report herein, for the first time, the isolation-from the cultures of Bacillus thuringiensis, B. subtilis, and B. velezensis strains-of di[(R)-2-ethylhexyl] phthalate, enantiomerically pure and in good yields: its biological activity against bacteria and fungi was probed and for the first time its synthesis was done.
A novel hydrogen-bonded silica-supported acidic ionic liquid: An efficient, recyclable and selective heterogeneous catalyst for the synthesis of diesters
Fareghi-Alamdari, Reza,Niri, Mehri Nadiri,Hazarkhani, Hassan
, (2018/05/28)
Abstract: In this study, two novel acidic ionic liquids, including a hydroxyl functionalized diacidic ionic liquid [HFDAIL] and a sulfonated diacidic ionic liquid [SFDAIL], were prepared and immobilized on the surface of silica nanoparticles (SNPs) via hydrogen bonding. The materials were characterized by FT-IR, NMR, SEM, nitrogen physisorption measurement, TGA and acid-base titration. The catalytic activity of the prepared catalysts was investigated in the synthesis of phthalate, maleate and succinate diesters under solvent-free conditions. It was found that nanosilica@[HFDAIL] with higher availability of acidic sites and higher hydrophilicity was more efficient compared to the nanosilica@[SFDAIL]. Notably, nanosilica@[HFDAIL] catalyst has also demonstrated excellent selectivity for the diester product while the monoester product was predominant in the case of nanosilica@[SFDAIL] even after prolonged reaction time or higher catalyst loading. In addition, the nanosilica@[HFDAIL] catalyst could be separated by simple filtration and reused several times without any significant loss of catalytic performance, but a remarkable decrease in activity was observed for nanosilica@[SFDAIL] in the next runs. GRAPHICAL ABSTRACT?: SYNOPSIS Two novel acidic ionic liquids, including a hydroxyl functionalized diacidic ionic liquid [HFDAIL] and a sulfonated diacidic ionic liquid [SFDAIL], were prepared and immobilized on the surface of silica nanoparticles via hydrogen bonding. The catalytic activity of the catalysts was investigated in the synthesis of diesters under solvent-free conditions.