131-70-4Relevant articles and documents
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Berman et al.
, p. 2139,2145 (1948)
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Berman,Melnichuk,Othmer
, p. 1312,1314, 1319 (1948)
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Involvement of a novel mouse hepatic microsomal esterase, ES46.5K, in the hydrolysis of phthalate esters
Kayano, Yuichiro,Watanabe, Kazuhito,Matsunaga, Tamihide,Yamamoto, Ikuo,Yoshimura, Hidetoshi
, p. 749 - 751 (1997)
ES46.5K, a novel esterase from mouse hepatic microsomes (Watanabe K., et al., Biochem. Mol. Biol. Int., 31, 25-30 (1993)), catalyzed hydrolysis of phthalate esters. ES46.5K and mouse hepatic microsomes hydrolyzed diethyl-, dibutyl-, diisobutyl-, dioctyl- and diethylhexyl phthalates, whereas dicyclohexyl- and dipbenyl phthalates having ring structure were not hydrolyzed by the enzymes. V(max) (μmol/min/mg protein)/K(m) (μM) ratios of ES46.5K for diethyl-, dibutyl-, diisobutyl-, dioctyl- and diethylhexyl phthalates were 291, 2786, 565, 51 and 57, respectively, while those of microsomes were 0.58, 0.83, 1.71, 0.05 and 1.10, respectively. The hydrolytic activity of ES46.5K was inhibited by diisopropylfluorophosphate and bis-p- nitrophenylphosphate. These results suggest that ES46.5K has high catalytic activity for phthalate esters and some role in the metabolism of phthalate esters in mice.
Mechanism of testicular atrophy induced by di-n-butyl phthalate in rats. Part 5. Testicular iron depletion and levels of ferritin, haemoglobin and transferrin m the bone marrow, liver and spleen
Fukuoka,Kobayashi,Hayakawa
, p. 379 - 386 (1995)
This study reports changes in levels of ferritin, haemoglobin and transferrin in the bone marrow, liver and spleen as an attempt to determine the causes of testicular iron depletion. A single oral dose of di-n-butyl phthalate (DBP) to male rats caused a sloughing of the germ cells (at 6 h) prior to testicular atrophy. Before the sloughing it was observed that DBP induced decreases both in the iron levels in the blood, bone marrow and testis and in haemoglobin (Hb) levels in the blood, bone marrow and spleen. Decrease in transferrin (Tf) levels was observed in the liver. Significant increases in ferritin and haemosiderin (Hs) levels were observed in the spleen and in the liver and spleen, respectively. In v;fro studies where mono-n-butyl phthalate (MBP) was incubated with liver homogenates, MBP caused both the decreases in Hb and Tf-bound iron levels and increases in Hs and Hs-iron levels. The present study proposes that the mechanism of testicular atrophy by DBP might be associated with both the iron release from Hb and/or Tf in the liver and spleen and the subsequent depletion of iron in the blood and testes.
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
, 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
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.
