Reaction of aromatic carboxylic acids with isocyanates using ionic liquids as novel and efficient media

Mallakpour, Shadpour; Yousefian, Hamed

doi:10.1590/s0103-50532007000600017

Cited by 8 publications

(3 citation statements)

References 5 publications

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“…Isocyanates can also react with carboxylic acids via an amidation reaction, albeit the yield in conventional organic solvents is typically low [ 28 ]. Besides, the side reaction of isocyanates with water results in amine formation and CO 2 gas release.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Graphene Oxide Derivatives via Functionalization Reaction with Hexamethylene Diisocyanate

et al. 2018

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Graphene oxide (GO), the oxidized form of graphene, shows unique properties including high mechanical strength, optical transparency, amphiphilicity and surface functionalization capability that make it attractive in fields ranging from medicine to optoelectronic devices and solar cells. However, its insolubility in non-polar and polar aprotic solvents hinders some applications. To solve this issue, novel functionalization strategies are pursued. In this regard, this study deals with the preparation and characterization of hexamethylene diisocyanate (HDI)-functionalized GO. Different reaction conditions were tested to optimize the functionalization degree (FD), and detailed characterizations were conducted via elemental analysis, Fourier-transformed infrared (FT-IR) and Raman spectroscopies to confirm the success of the functionalization reaction. The morphology of HDI-GO was investigated by transmission electron microscopy (TEM), which revealed an increase in the flake thickness with increasing FD. The HDI-GO showed a more hydrophobic nature than pristine GO and could be suspended in polar aprotic solvents such as N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP) and dimethyl sulfoxide (DMSO) as well as in low polar/non-polar solvents like tetrahydrofuran (THF), chloroform and toluene; further, the dispersibility improved upon increasing FD. Thermogravimetric analysis (TGA) confirmed that the covalent attachment of HDI greatly improves the thermal stability of GO, ascribed to the crosslinking between adjacent sheets, which is interesting for long-term electronics and electrothermal device applications. The HDI-GO samples can further react with organic molecules or polymers via the remaining oxygen groups, hence are ideal candidates as nanofillers for high-performance GO-based polymer nanocomposites.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Graphene Oxide Derivatives via Functionalization Reaction with Hexamethylene Diisocyanate

et al. 2018

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“…The acids, as well as bases, could be particularly sensitive to solvation effects. The carboxylic acids have been widely used in IL solutions both as substrates and catalysts . Therefore, we wanted to get a quantitative estimation of their strength in these media.…”

Section: Introductionmentioning

confidence: 99%

p-Nitrophenolate: A Probe for Determining Acid Strength in Ionic Liquids

2009

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In order to obtain an acidity scale in room-temperature ionic liquid solutions, the protonation equilibrium of sodium p-nitrophenolate in [bm(2)im][NTf(2)] and in [bmpyrr][NTf(2)], at 298 K, has been studied by means of spectrophotometric titration. Carboxylic acids differing in both structure and in water solution strength have been used. Data collected indicate that in the analyzed ionic liquid solutions carboxylic acids are less dissociated than in water solution. Furthermore, by virtue of a mutual interaction, the studied equilibrium seems to be affected by both the nature of the ionic liquids and the carboxylic acids.

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“…图式 7 硫代水杨酸与席夫碱的反应 Scheme 7 Reaction of thiosalicylic acid with schiff base 2010 年, Martens 等 [32] 利用硫代水杨酸和环状亚胺衍生物为原料, 在甲苯中回流首先得到了巯基与亚胺发生加成反应的中间体 14 [33] , 然后脱水环化合成 1,3-苯并噻嗪-4-酮类衍生物, 总产率 27%～74% (Scheme 9 率高达 96% (Scheme 11). 此法是一步合成 1,3-苯并噻嗪二酮的好方法, 在文中没有讨论该方法的反应机理, 我们认为巯基与羧基可能均与异氰酸酯反应生成了中间体 20 [35] , 然后环化合成了目标产物. Shestakov 等 [37] 使硫氰酸钾与硫代水杨酸在吡啶和水的混合液中反应合成了 1,3-苯并噻嗪二酮类衍生物.…”

Section: 分子内成环合成 13-苯并噻嗪酮的方法unclassified

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

李闪闪¹,

Shanshan²

2016

Chin. J. Org. Chem.

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1,3-Benzothiazinone derivatives have widely bioactivities. So the methods for the synthesis of these 1,3-benzothiazinone derivatives have attracted enormous attentions worldwide. From the method of introducing sulfur atom and the reaction mechanism for the formation of benzothiazinone derivatives, the method of synthesizing 1,3-benzothiazinone derivatives has been summarized in this review. So the thiophenol derivatives, disulfide derivatives, the same carbon connected with amino and mercapto derivatives, isothiocyanate derivatives and some smaller sulfur molecules are used as starting materials.

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Reaction of aromatic carboxylic acids with isocyanates using ionic liquids as novel and efficient media

Cited by 8 publications

References 5 publications

Synthesis and Characterization of Graphene Oxide Derivatives via Functionalization Reaction with Hexamethylene Diisocyanate

Synthesis and Characterization of Graphene Oxide Derivatives via Functionalization Reaction with Hexamethylene Diisocyanate

p-Nitrophenolate: A Probe for Determining Acid Strength in Ionic Liquids

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

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