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Accessing a key intermediate for sub(oxa)porphyrins from a sustainable raw-material—Cashew apple bagasse
Industrial Crops and Products ( IF 5.9 ) Pub Date : 2020-11-13 , DOI: 10.1016/j.indcrop.2020.113081
Rajamani Rajmohan , Penugonda Prathyusha , Jaganathan Maheswari , Venkatesan S. Thimmakondu , Pothiappan Vairaprakash , Arumugam Arumugam

Furan-2,5-diylbis(phenylmethanol) is a key intermediate to access sub(oxa)porphyrins. Previously, this key intermediate was accessible from fossil-derived furan using highly dangerous lithium reagents. Presently, we have produced this key intermediate from cashew apple bagasse (CAB), via the formation of 5-hydroxymethylfurfural (HMF). CAB is non-food biomass containing cellulose and hemicellulose. From the CAB, we have obtained the HMF in the yield of 310 mg/g of CAB. The Response Surface Methodology (RSM) optimized condition for efficient conversion of CAB to HMF is (i) temperature at 180 °C, (ii) 1:1 mol ratio of catalysts (ZnSO4/NaHSO4), and (iii) reaction duration of 3 h. CAB-derived HMF is treated with an oxidizing agent pyridinium chlorochromate (PCC) to obtain 2,5-diformylfuran (DFF). DFF is converted into furan-2,5-diylbis(phenylmethanol) in a reaction with phenylmagnesium bromide. Based on the TD-DFT analysis of sub(oxa)porphyrins, it is concluded that the absorption behavior of sub(oxa)porphyrins can be tuned by introducing electron-withdrawing groups into the phenyl ring of the sub(oxa)porphyrins.



中文翻译:

从可持续的原材料腰果苹果蔗渣中获得亚(氧杂)卟啉的关键中间体

呋喃-2,5-二基双(苯基甲醇)是获得亚(氧杂)卟啉的关键中间体。以前,这种关键中间体是使用高度危险的锂试剂从化石衍生的呋喃中获得的。目前,我们已经通过形成5-羟甲基糠醛(HMF)从腰果苹果蔗渣(CAB)中生产了这种关键中间体。CAB是含有纤维素和半纤维素的非食品生物质。从CAB中,我们获得了310 mg / g CAB的HMF。有效将CAB转化为HMF的响应表面方法(RSM)优化条件是(i)180°C的温度,(ii)1:1摩尔比的催化剂(ZnSO 4 / NaHSO 4)和(iii)反应时间为3小时。将CAB衍生的HMF用氧化剂氯铬酸吡啶鎓(PCC)处理,以获得2,5-二甲酰呋喃(DFF)。在与苯基溴化镁的反应中,DFF转化为呋喃-2,5-二基双(苯基甲醇)。基于亚氧杂卟啉的TD-DFT分析,得出可以通过将吸电子基团引入亚氧杂卟啉的苯环来调节亚氧杂卟啉的吸收行为的结论。

更新日期:2020-11-13
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