Green synthesis of benzonitrile using ionic liquid with multiple roles as the recycling agent

Li, Zhihui; Wang, Tingting; Qi, Xudong; Yang, Qiusheng; Gao, Liya; Zhang, Dongsheng; Zhao, Xinqiang; Wang, Yanji

doi:10.1039/c9ra02296a

Cited by 12 publications

(5 citation statements)

References 30 publications

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“…In recent years, the oximation-dehydration of aldehydes with hydroxylamine salts to synthesize nitriles has attracted the attention of researchers. [14][15][16][17] In our previous study, we reported the reaction of HMF with a hydroxylamine aqueous solution to obtain HMFO, with 98% conversion and 88% HMFC yield under the conditions of n(HMF) : n(NH 2 OH) = 1 : 1.5, H 2 O as the solvent, and 55 °C for 5 min. Based on this, the HMFC yield reached 100% when hydroxylamine zinc chloride salt (ZnCl 2 •2NH 2 OH) was used as the nitrogen source when the reaction was carried out at 100 °C for 20 min.…”

Section: Introductionmentioning

confidence: 99%

Selectivity controlled synthesis of furan-ring nitrogenous compounds from 5-hydroxymethylfurfural, ammonia and hydrogen peroxide

Gao,

Li,

Zhang

et al. 2024

Catal. Sci. Technol.

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Section: Introductionmentioning

confidence: 99%

Selectivity controlled synthesis of furan-ring nitrogenous compounds from 5-hydroxymethylfurfural, ammonia and hydrogen peroxide

Gao,

Li,

Zhang

et al. 2024

Catal. Sci. Technol.

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Section: Introductionmentioning

confidence: 99%

“…Beside a wide distribution of natural products, benzonitrile as a simplest nitrogen-bearing aromatic molecules has been discovered recently in the interstellar medium. , Benzonitrile and its derivatives are comprising an important class of organic compounds in the chemical industry. This is a stable compound for pyrolysis, an essential process in the synthesis of benzoic acid, benzylamine, benzamide, pesticides, and fatty amines, and dyes could be precursors for the synthesis of benzylamine, which can be used as a pharmaceutical intermediate. , …”

Section: Introductionmentioning

confidence: 99%

“…This is a stable compound for pyrolysis, 4 an essential process in the synthesis of benzoic acid, benzylamine, benzamide, pesticides, and fatty amines, and dyes could be precursors for the synthesis of benzylamine, which can be used as a pharmaceutical intermediate. 5,6 Benzonitrile is generally a good solvent for the synthesis of organic, anhydrous inorganic, and organometallic compounds and is generally similar in its behavior as a solvent to acetonitrile (CH 3 CN). 7 However, benzonitrile differs from acetonitrile in two interesting and significant ways: it has delocalized πelectrons in the phenyl ring constantly interacting with the −C�N group, and it has a large phenyl group as compared to the methyl group, creating a steric problem.…”

Section: Introductionmentioning

confidence: 99%

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Simulation Investigation of Bulk and Surface Properties of Liquid Benzonitrile: Ring Stacking─Assessment and Deconvolution

Sakhtemanian

Ghatee

2022

ACS Omega

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The content and the molecular dynamics (MD) simulation analysis here are inspired by our recent ab initio calculation on benzonitrile (BZN), whereas the present results are to expand and develop macroscopic documentation involving data verification. MD simulations of the bulk liquid BZN in the range of 293–323 K unravel the hydrogen bond (−C≡N···H) formation with strength in the order of ortho -H ≫ meta -H ∼> para -H. The possibility for ortho -Hs to get involved in the formation of two bonds simultaneously confirms each having σ- and π-bonding features. Accordingly, we used vast efforts for structural analysis particularly based on the deconvolution of the corresponding complex correlation functions. Specific angle-dependent correlation functions led to the recognition of the molecular stacking with a strict anti-parallel orientation. The in-plane dimer and trimer also take part in the structural recognition. A singularity, found in the trend of the simulated temperature-dependent viscosity and diffusion coefficient of liquid BZN, is centered at about 313 K and quite fascinatingly emulates the reported experiment viscosity. An interplay between a small change in the trend of density and a large change in the corresponding viscosity is a key factor in supporting the singularity. Deconvolution of the simulation results allows attributing the singularity to structural alteration involving H-bonding of different types and extent. Approaching the range of 308–313 K, an alteration between hydrogen bond formation involving mostly ortho -Hs and mixed ortho -Hs + meta -H is possible and supports the singularity.

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“…This is a stable compound to pyrolysis 4 an essential process in the synthesis of benzoic acid, benzylamine, benzamide, pesticides, fatty amines, dyes and could be precursors for the synthesis of benzylamine, which can be used as a pharmaceutical intermediate. 5,6 Also, benzonitrile is generally a good solvent for the synthesis of organic, anhydrous inorganic, and organometallic compounds and is generally similar in its behavior as a solvent to acetonitrile (CH3CN). 7 But, benzonitrile differs from acetonitrile in two interesting and significant ways: it has delocalized -electrons in the phenyl ring constantly interacting with the ̶ C≡N group, and it has a large phenyl group as compared to the methyl group creating a steric problem.…”

Section: Introductionmentioning

confidence: 99%

Simulation Investigation of Bulk and Surface Properties of Liquid Benzonitrile: Ring Stacking  Assessment and Deconvolution

Sakhtemanian

Ghatee

2021

Preprint

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This manuscript is devoted to classical molecular dynamics (MD) simulation studies of the bulk and surface properties of liquid benzonitrile (BZN) in the temperature range of 293-323K. The content and the simulation-analysis are inspired by our recent ab initio calculation on benzonitrile, whereas present results are to expand and develop macroscopic documentation involving data verification. We investigate the molecular stacking that involves phenyl ring, which is notably absent in the counterpart acetonitrile solvent. MD simulations of the bulk liquid unravel the hydrogen bond (C≡N⋯H) formation and strength, in the order of ortho-H >> meta-H ~>para-H. The possibility for ortho-H’s to get involved in the formation of two bonds simultaneously confirms each having - and -bonding features. The singularity centered at about 313 K found in the trend of the simulated temperature-dependent viscosity and diffusion coefficient of liquid BZN goes alongside the reported experiment, and the phenomenon may root from a change in the internal frictional motion of the molecular cluster in stacking modes. Accordingly, we used vast efforts for analysis particularly based on the deconvolution of the corresponding complex correlation functions. Specific angle-dependent correlation functions led to the recognition of the stacking molecules and their strict orientational character by utilizing relative molecular twist angles. Recognition of the strict orientational character of the stacking molecules, as a clue to the singularity in the viscosity trend, will be discussed based on specific angle-dependent correlation functions.

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Green synthesis of benzonitrile using ionic liquid with multiple roles as the recycling agent

Abstract: ILs exhibited good co-solvent, catalytic, phase separation and recycling performance in the green synthesis of benzonitrile from benzaldehyde and (NH2OH)2·ILs.

Cited by 12 publications

References 30 publications

Selectivity controlled synthesis of furan-ring nitrogenous compounds from 5-hydroxymethylfurfural, ammonia and hydrogen peroxide

Selectivity controlled synthesis of furan-ring nitrogenous compounds from 5-hydroxymethylfurfural, ammonia and hydrogen peroxide

Simulation Investigation of Bulk and Surface Properties of Liquid Benzonitrile: Ring Stacking─Assessment and Deconvolution

Simulation Investigation of Bulk and Surface Properties of Liquid Benzonitrile: Ring Stacking  Assessment and Deconvolution

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