Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br

Xu, Xuetang; Duan, Wengui; Huang, Mei; Li, Guanghua

doi:10.1016/j.carres.2011.06.011

Cited by 7 publications

(6 citation statements)

References 18 publications

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“…These materials with relatively high DS values between 1.0 and 3.0 might find use as chiral stationary phase in chromatography. IL/DMF mixtures have been exploited as reaction media for the homogeneous esterification of cellulose with haloacyl halogenides [ 58 , 59 , 60 , 61 ]. The 2-bromo- and 2-chloro carboxylic acid esters obtained (entry 14 ) have been used as macro-initiators for grafting poly(methacrylates) and poly(styrene) onto the cellulose backbone via atom transfer radical polymerization (ATRP).…”

Section: Historymentioning

confidence: 99%

“…No ILs or other cellulose solvents are required for the grafting reaction since the macro-initiators readily dissolve in molecular organic solvents. ILs have been used as reaction medium for ATRP as well but in that particular case, no advantages in terms of conversion rate could be observed compared to reactions in DMF [ 61 ]. ILs might be useful for grafting via ATRP, when preparation of the cellulose macro-initiator and subsequent polymerization can be combined in a one-pot synthesis without previous isolation and purification of the intermediate compound.…”

Section: Historymentioning

confidence: 99%

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Ionic Liquids — Promising but Challenging Solvents for Homogeneous Derivatization of Cellulose

2012

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In the past decade, ionic liquids (ILs) have received enormous interest as solvents for cellulose. They have been studied intensively for fractionation and biorefining of lignocellulosic biomass, for dissolution of the polysaccharide, for preparation of cellulosic fibers, and in particular as reaction media for the homogeneous preparation of highly engineered polysaccharide derivatives. ILs show great potential for application on a commercial scale regarding recyclability, high dissolution power, and their broad structural diversity. However, a critical analysis reveals that these promising features are combined with serious drawbacks that need to be addressed in order to utilize ILs for the efficient synthesis of cellulose derivatives. This review presents a comprehensive overview about chemical modification of cellulose in ILs. Difficulties encountered thereby are discussed critically and current as well as future developments in this field of polysaccharide research are outlined.

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Section: Historymentioning

confidence: 99%

Section: Historymentioning

confidence: 99%

Ionic Liquids — Promising but Challenging Solvents for Homogeneous Derivatization of Cellulose

2012

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“…24 However, both 1,3,4-thiadiazole and amide moieties are also the available pharmacophores in the discovery of novel drugs or agrochemicals, including insecticidal, 25 antiviral, 26 antifungal, 27,28 antitumor agents, 29 and herbicidal activities. 30 Herein, taking the earlier-mentioned clues into consideration along with the continuation of our interest in the works on natural product-based drug-delivery carriers, 8,[31][32][33][34] and bioactive compounds, 17,19,27,35,36 a series of novel nanopesticide carriers ETOCN-1-ETOCN-4 were prepared by TEMPO oxidation of bleached bagasse pulp and then esterification of TEMPO-oxidized cellulose nanofibers (TOCN) with intermediate 4 converted from 3-carene. Then, a series of 1,3,4-thiadiazole-amide compounds containing gem-dimethylcyclopropane ring 8a-8u were designed, synthesized by multi-step reaction, and characterized by means of Fourier-transform infrared (FTIR), proton nuclear magnetic resonance ( 1 H-NMR), carbon-13 ( 13 C)-NMR, electrospray ionizationmass spectrometry (ESI-MS) and elemental analysis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3‐carene‐derived nanocellulose/1,3,4‐thiadiazole‐amide complexes with antifungal activity for plant protection

Zou

Duan

et al. 2022

Pest Management Science

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BACKGROUND Nanopesticides have been proved to be a powerful and promising tool to solve the issues in agriculture. The purpose of the present study was to develop ecofriendly nanopesticide systems by the strategy of comprehensive utilization of two natural biomass resources (bagasse and turpentine oil) because of their incomparable advantages. RESULTS In this research, a series of nanocellulose carriers ETOCN‐1–ETOCN‐4 (ETOCN, esterified TEMPO‐oxidized cellulose nanofibers) with different degrees of substitution were prepared and characterized by Fourier‐transform infrared (FTIR), X‐ray diffraction (XRD) and transmission electron microscopy (TEM). Then, 21 1,3,4‐thiadiazole‐amide compounds 8a–8u containing gem‐dimethylcyclopropane ring were designed, synthesized and characterized. A preliminary bioassay indicated that compound 8i (R = p‐Br Ph) exhibited broad‐spectrum antifungal activity against the tested fungi. Furthermore, drug‐loading complexes 8i/ETOCN‐1–8i/ETOCN‐4 were fabricated by integration of nanocellulose‐based carriers ETOCN‐1–ETOCN‐4 with bioactive compound 8i, and the drug‐loading capacities, microstructures and sustained‐releasing performance of these complexes were also investigated. According to the observation of scanning electron microscopy (SEM) images of complex 8i/ETOCN‐2, the small‐molecule drug and the carrier formed a well‐distributed and compact complex, which led to the excellent drug‐loading capacity and sustained‐releasing performance in the ethanol/water (1:1, v/v) system. CONCLUSIONS Complexes 8i/ETOCN‐1–8i/ETOCN‐4 deserved further study as the promising candidates for the development of nanopesticides. © 2022 Society of Chemical Industry.

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“…[5][6][7][8] More interestingly, by using ILs as the medium, some novel cellulose esters, such as pyropheophorbide a ester of cellulose, 3,6,9-trioxadecanoic acid ester of cellulose and cellulose dehydroabietate, were also synthesized. [9][10][11] The homogeneous esterication of cellulose in ILs not only provides a possibility to control degree of substitution (DS) and structure of cellulose esters, but also gives a high efficiency. However, so far, there is almost no available information about the reaction mechanism and reaction process of the homogeneous esterication of cellulose at the molecular level.…”

Section: Introductionmentioning

confidence: 99%

Homogeneous benzoylation of cellulose in 1-allyl-3-methylimidazolium chloride: Hammett correlation, mechanism and regioselectivity

Chen

Feng

Zhang³

et al. 2015

RSC Adv.

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Homogeneous benzoylation of cellulose with a series of substituted benzoyl chlorides, in which substituents varied from electron donating to electron withdrawing groups, was investigated in an ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl). The electronic effect of substituents had a considerable effect on the reaction. A plot of Hammett parameters of substituents vs. degree of substitution (DS) of resultant cellulose esters exhibited a V-shaped graph: a negative slope for negative Hammett parameters, and a positive slope for positive Hammett parameters. Such a Hammett plot indicated the mechanism of cellulose benzoylation: the reaction underwent a unimolecular ionization mechanism with a carbocationic intermediate when benzoyl chlorides were with electron-donating substituents, and a bimolecular addition-elimination mechanism with a tetrahedral intermediate when benzoyl chlorides were with electron-withdrawing substituents. In addition, 13 C-NMR analysis showed that most of the substituted benzoyl chlorides exclusively preferred the primary hydroxyl at the C-6 position. This unusually high regioselectivity was attributed to the synergistic effect of appropriate reaction rate, moderate steric effect and reaction mechanism of benzoylation.

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Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br

Cited by 7 publications

References 18 publications

Ionic Liquids — Promising but Challenging Solvents for Homogeneous Derivatization of Cellulose

Ionic Liquids — Promising but Challenging Solvents for Homogeneous Derivatization of Cellulose

Synthesis of 3‐carene‐derived nanocellulose/1,3,4‐thiadiazole‐amide complexes with antifungal activity for plant protection

Homogeneous benzoylation of cellulose in 1-allyl-3-methylimidazolium chloride: Hammett correlation, mechanism and regioselectivity

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