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Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water

  • Behzad Zeynizadeh , Farkhondeh Mohammad Aminzadeh and Hossein Mousavi EMAIL logo
Published/Copyright: August 6, 2019
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 8 Issue 1

Abstract

Two simple, efficient, and environmentally benign protocols for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of aromatic nitro compounds promoted by CuFe2O4 nanoparticles in water at reflux have been developed. The prepared CuFe2O4 MNPs are well known and fully characterized by various techniques. Furthermore, the CuFe2O4 NPs easily separated from the reaction environment using an external magnetic field and can be reused for several times without significant loss of its activity for both mentioned reactions.

Keywords: N-arylacetamide; N-acetylation of arylamine; reductive acetylation of nitroarene; CuFe2O4; green chemistry

1 Introduction

Performing organic reactions into the green solvents especially water is very favorable for academic researchers and industrial chemical companies due to its many desirable features such as low-cost, non-toxicity, safety, abundantly and also environmentally friendless compared with organic solvents [1, 2, 3, 4, 5, 6, 7, 8, 9, 10].

In recent years, construction of amide linkages is one of the valuable reactions in organic synthesis because of their extensive applications in various area such as peptide synthesis, agrochemicals, polymers, functional materials, dyes, fragrances and also existence in pharmaceuticals (Figure 1) and natural products (Figure 2) [11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25]. Due to the importance of amide compounds, developing simple, practical, environmentally benign, cost- and time-effective manners for their synthesis is very valuable and necessary. Undoubtedly, acetylation of arylamines is a very simple approach for the preparation of amides which is widely used in chemistry labs and chemical industry [26]. Therefore, the development of this mentioned method is justifiable. It is worthwhile to note that aromatic nitro compounds are much cheaper than arylamines in terms of price and one of the most important substrates for the preparation of arylamines via reduction process. So, designing new protocols for the synthesis of amides via straightforward one-pot reductive acetylation of aromatic nitro compounds without isolation of the arylamine intermediates is very interesting. In this regard, it should be noted that one-pot multicomponent reactions (MCRs) are remarkable instruments for versatile preparation of a wide diversity of organic compounds especially biologic active molecules which have advantages such as high atom economy, escape of time-consuming protection-deprotection steps, and environmentally friendliness, making them absolutely better than classical multistep synthetic pathways [27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37].

Notably, in recent years, spinel ferrite nanoparticles with the general formula MFe2O4, where M(II) is a d-block transition metal (such as Mn, Co, Ni, Cu, Zn) have been in the vanguard of nanoscience and nanotechnology due to their unique specifications like nanometer size, high saturation magnetization, large surface area to volume ratio, high electric resistivity, low eddy current loss, very good optical properties in the visible region and also their extensive applications in sensors, memory storage devices, magnetically controlled drug delivery, hyperthermia in the treatment of cancer diseases, medical diagnostics, magnetic resonance image (MRI) enhancement, telecommunication, pigments, and catalysis [38, 39, 40, 41, 42, 43, 44, 45]. Furthermore, compared with iron oxides, spinel ferrites provide flexibility to control both crystal structures and magnetic properties by choosing different non-iron metals in spinel ferrite backbone and controlling their molar concentrations. Among various type of spinel ferrite magnetic nanoparticles (MNPs), CuFe2O4 nanocomposite, in addition to numerous applications, has shown satisfactory performance as the recyclable catalyst in various organic transformations such as synthesis of heterocyclic compounds [46, 47, 48, 49, 50, 51, 52], Ullmann C-O coupling reaction [53], direct synthesis of chemical structures containing both phenol ester and benzothiazole moieties via dehydrogenative coupling reactions [54], reduction of p-nitrophenol [55], one-pot odorless carbon-sulfur bond formation reactions [56], directed phenol/formamide coupling [57], synthesis of diaryl/aryl alkyl sulfides via cross-coupling process [58], S-arylation of thioureas by aryl halides [59], one-pot four-component Dakin-West reaction (synthesis of β-acetamido ketones) [60], Friedel-Crafts acylation [61], N-arylation of heterocycles [62], direct C-H amination of benzothiazoles [63], oxidative hydroxylation of arylboronic acids [64], palm oil methanolysis [65], oxidation of benzyl alcohol [66], synthesis of unnatural arundines [67], N-arylation of indole and imidazole with aryl halide [68], and so on.

Figure 1 Representative examples of amide-containing drugs.
Figure 1

Representative examples of amide-containing drugs.

Figure 2 Examples of amide-containing natural products.
Figure 2

Examples of amide-containing natural products.

In continuation of our research programs on various type of organic reactions [67, 68, 69, 70, 71], especially on the simple methodologies for the preparation of N-arylacetamides [72, 73, 74, 75], we wish to report two different facile and efficient approaches for the synthesis of divers N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 MNPs in water at reflux (Scheme 1).

Scheme 1 Two different facile and efficient approaches for the synthesis of various N-arylacetamides promoted by CuFe2O4 MNPs.
Scheme 1

Two different facile and efficient approaches for the synthesis of various N-arylacetamides promoted by CuFe2O4 MNPs.

2 Results and discussion

2.1 Preparation and characterization of the CuFe2O4 magnetically nanocomposite

First of all, CuFe2O4 magnetically nanoparticles (MNPs) prepared through the simple procedure which was reported by Jia and co-workers [76]. Notably, the obtained CuFe2O4 nanocomposite fully characterized by various techniques including Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray (EDX) spectroscopy, inductively coupled plasma-optical emission spectrometry (ICP-OES), vibrating sample magnetometer (VSM) and also BET-BJH analyses.

In the FT-IR spectrum of the prepared CuFe2O4 (Figure 3), the absorption band at 586.8 cm-1 is ascribed to the stretching vibration frequency of octahedral site, and the absorption band at 405.8 cm-1 is related to the tetrahedral site.

Figure 3 FT-IR spectrum of the CuFe2O4 MNPs.
Figure 3

FT-IR spectrum of the CuFe2O4 MNPs.

As can be seen from Figure 4, the XRD pattern of the mentioned CuFe2O4 nanocomposite reveals that all the peaks matched with the standard XRD pattern of CuFe2O4 (JCPDS card no. 34-0425). Furthermore, the sharp peaks which existed in the XRD pattern of the synthesized copper ferrite MNPs prove the crystalline nature of the mentioned nanocomposite.

Figure 4 XRD spectrum of the CuFe2O4 MNPs.
Figure 4

XRD spectrum of the CuFe2O4 MNPs.

According to the SEM (Figure 5) and TEM (Figure 6) images, the particles of the synthesized CuFe2O4 nanocomposite are in the nanometric range along with irregular morphology.

Figure 5 SEM images of the CuFe2O4 MNPs.
Figure 5

SEM images of the CuFe2O4 MNPs.

Figure 6 TEM images of the CuFe2O4 MNPs.
Figure 6

TEM images of the CuFe2O4 MNPs.

The EDX spectrum of the CuFe2O4 shows that Cu, Fe, and O are present in the structure of the prepared nanocomposite (Figure 7). Also, the ICP-OES analysis showed that the amounts of Cu, Fe, and O in the CuFe2O4 nanocomposite were 22.52%, 46.71%, and 30.77%, respectively.

Figure 7 EDX spectrum of the CuFe2O4 MNPs.
Figure 7

EDX spectrum of the CuFe2O4 MNPs.

The obtained saturation magnetization value (Ms = 38 emu·g-1) and the shape of the illustrated pattern show that the prepared nanocatalyst has a ferromagnetic characteristic for a convenient magnetic separation (Figure 8).

Figure 8 VSM spectrum of the CuFe2O4 MNPs.
Figure 8

VSM spectrum of the CuFe2O4 MNPs.

The nitrogen adsorption-desorption isotherm of the CuFe2O4 NPs was measured (Figure 9). As shown in Figure 9, the prepared nanocomposite exhibited type III isotherm, indicating micro-pore nature of the CuFe2O4. Also, according to the BET equation, the specific surface area (SSA) and pore volume value (PVV) of the mentioned nanocomposite calculated (SSA = 5.46 m2·g-1 and PVV = 0.0077 cm3·g-1).

Figure 9 N2 adsorption-desorption isotherm for the CuFe2O4 MNPs.
Figure 9

N2 adsorption-desorption isotherm for the CuFe2O4 MNPs.

Besides, the distribution of pore size is 1.88 nm based on the Barrett-Joyner-Halenda (BJH) analysis.

2.2 N-acetylation of arylamimes promoted by CuFe2O4 MNPs

Indisputable, amine acetylation is one of the most extensively used reactions in organic chemistry and is often used in the preparation of amide compounds and also protection of –NH functional group. N-acetylation of amine is generally accomplished using acetic anhydride or acetyl chloride as acetyl donors in the presence of an acidic or basic catalyst in the organic medium. Up to now, several methods have been reported for the mentioned reaction. Nevertheless, some of these methods along with some merits have one or more drawbacks such as the use of expensive and harmful reagents, solvents or catalysts, harsh reaction conditions, low yield of products and (or) lengthy reaction times and so on [77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96]. In this regard, we decided to introduce a simple, efficient, green, cost-and time-effective protocol for the N-acetylation of arylamines.

At the outset of experimental work, the reaction of aniline with acetic anhydride (Ac2O) as an acetylating agent was chosen as a model reaction to confirm the feasibility of our strategy and optimize the reaction conditions (Table 1). At first, we evaluated the effect of various solvents such as MeOH, EtOH, THF, CH3CN, and EtOAc, on the model reaction utilizing a different molar ratio of CuFe2O4 MNPs. As shown in entry 9 of Table 1, the best condition for this mentioned reaction was the use of 1 mmol Ac2O and also 0.3 mmol of CuFe2O4 MNPs in water at reflux. Furthermore, to examine the reaction scope, various arylamines possessing electron-withdrawing (EWD) and electron-donating groups (EDG) were reacted with Ac2O under the optimized reaction conditions to give the corresponding N-arylacetamides. Based on the data shown in Table 2, all the desired products were prepared in good to excellent yields. It is worth noting the chemoselectivity observed for the arylamines containing benzylic alcohol group (Table 2, entry 13 and 14).

Table 1

Optimization experiments for the N-acetylation of aniline to acetanilide.

EntryCuFe2O4 (mmol)Ac2O (mmol)SolventTimeConv. (%)
113MeOH2 hN.R.
213EtOH2 hN.R.
313THF2 hN.R.
413CH3CN2 hN.R.
51-EtOAc2 hN.R.
613EtOAc2 h40
711H2O1 min100
80.51H2O1 min100
90.31H2O1 min100
100.21H2O2 min100

  1. N.R. = No reaction (Conv. = 0)

Table 2

N-acetylation of arylamines using Ac2O promoted by CuFe2O4 MNPs in water.

EntrySubstrateProductMolar RatioaTime (min)Yieldb (%)
11:0.3:1190
21:0.3:1485
31:0.3:1486
41:0.3:1486
51:0.3:2389
61:0.3:2389
71:0.3:1587
81:0.3:1.5587
91:0.3:1.5385
101:0.3:1486
111:0.3:1388
121:0.3:1386
131:0.3:1.5480
141:0.3:1.5280
151:0.3:1.5880
161:0.3:2389
171:0.3:2387
181:0.3:2389

  1. a Substrate:CuFe2O4:Ac2O.

    b Yields refer to isolated pure products.

2.3 One-pot reductive acetylation of aromatic nitro compounds promoted by CuFe2O4 MNPs

In order to optimize reaction conditions, the transformation of nitrobenzene (PhNO2) as a model compound to acetanilide was studied through a primary reduction of PhNO2 with sodium borohydride (NaBH4) using CuFe2O4 as recyclable promoter followed by acetylation with Ac2O in a one-pot procedure without isolation of aniline intermediate under different reaction conditions. The reductive acetylation of PhNO2 under mentioned system in protic and aprotic solvents such as MeOH, EtOH, THF, CH3CN, and EtOAc (Table 3, entries 1-5) and also under solvent-free condition (Table 3, entry 6) did not take place any more. Interestingly, further investigations demonstrated that H2O was the best solvent of choice (Table 3, entries 7-11) and using a molar equivalent of 1:1:2:1 for PhNO2, CuFe2O4, NaBH4 and also Ac2O, respectively, was an optimum for the complete mentioned one-pot reaction (Table 3, entry 7). More examinations also exhibited that completion of the model reaction with other amounts of the CuFe2O4 (0.7, 0.5, 0.3, and 0.2 mmol) was also accessible (Table 3, entries 8, 9, 10, and 11). However, prolonging the reaction time impeded using them as the optimum amount.

Table 3

Optimization experiments for the one-pot reductive acetylation of nitrobenzene to acetanilide promoted by CuFe2O4 MNPs.

EntryNaBH4 (mmol)CuFe2O4 (mmol)Ac2O (mmol)SolventTimeConv. (%)
1313MeOH2 hN.R.
2313EtOH2 hN.R.
3313THF2 hN.R.
4313CH3CN2 hN.R.
531-EtOAc2 hN.R.
6313-2 hN.R.
7211H2O11 min100
820.71H2O24 min100
920.51H2O46 min100
1020.31H2O49 min100
1120.21H2O52 min100
12210.5H2O45 min50

  1. N.R. = No reaction (Conv. = 0)

Having established the optimal reaction conditions, we investigated the substrate scope of this one-pot transformation using various aromatic nitro compounds. The obtained results are summarized in Table 4. As seen, all reactions were carried out successfully in H2O within 6-34 min, and the corresponding N-arylacetamides were obtained in good to excellent yields.

Table 4

One-pot reductive acetylation of aromatic nitro compounds promoted by CuFe2O4 MNPs.

EntrySubstrateProductMolar ratioaTime (min)Yieldb (%)
11:2:1:11197
21:2:1:11490
31:3:1:23287
4c1:3.5:1.52287
5c1:2:1:22285
61:2:1:1.53288
7c1:3:1:12980
8c1:3:1:13388
9c1:3:1:23389
10c1:3:1:1689
111:3:1:21187
12c1:3:1:11789
13c1:2:1:1.51284
14c1:4:1:22480
15c1:2.5:1:12780
16c1:3:1:23477
171:2:1:12778

  1. a Substrate:NaBH4:CuFe2O4:Ac2O.

    b Yields refer to isolated pure products.

    c In these reactions, NaBH4 was added portion-wisely.

More examinations showed that the chemoselective reductive acetylation of nitro group versus alcohol was successfully accessible. For example, reductive acetylation of 4-nitroabenzylalcohol to 4-acetamidobenzyl alcohol was carried out in 88% yield (Table 4, entry 6). In the case of nitrobenzaldehydes and nitroacetophenones, the same behavior was observable. In which, the nitro group was reduced and acetylated to acetamide, however, the carbonyl moieties were reduced to alcoholic function without acetylation (Table 4, entries 10-14). Molecules with the complexity of nitro and phenolic groups did not show any selectivity, and both of the functional groups were acetylated with the same reactivity. This fact was shown with reductive acetylation of o-nitrophenol to the corresponding 2-acetamidophenyl acetate (Table 4, entry 3). Table 4, entry 16 represents this protocol was also efficient for reductive acetylation of dinitro compounds using 1:3:2 molar equivalents of the CuFe2O4, NaBH4, and Ac2O respectively, in H2O at reflux.

Notably, the exact mechanism for the one-pot reductive acetylation reaction of nitroarenes in the presence of CuFe2O4 as a simple and efficient promoter is not known. But, based on our observations and literature survey [71,74, 75], a plausible reaction mechanism for this reaction is presented in Scheme 2. Firstly, nitroarene and hydrogen which is obtained from the reaction of NaBH4 and water absorbed on the surface of CuFe2O4 NPs. After completion of the reduction process which was accompanied by the elimination of two molecules of water, generated arylamine intermediate attacked to Ac2O (which was activated by CuFe2O4) caused the formation of desired amide compound along with carboxylic acid as an only side product.

Scheme 2 Plausible mechanism for the one-pot reductive acetylation of nitroarenes promoted by CuFe2O4 MNPs.
Scheme 2

Plausible mechanism for the one-pot reductive acetylation of nitroarenes promoted by CuFe2O4 MNPs.

2.4 Reusability

The recoverability and reusability of the CuFe2O4 NPs were studied using the N-acetylation of aniline and also one-pot reductive acetylation of nitrobenzene reactions. After completion of the reaction, the catalyst separated by an external magnet and reused for the subsequent runs without significant loss of its catalytic activity (Figures 10 and 11).

Figure 10 Reusability of the CuFe2O4 MNPs in the N-acetylation of aniline.
Figure 10

Reusability of the CuFe2O4 MNPs in the N-acetylation of aniline.

Figure 11 Reusability of the CuFe2O4 MNPs in the one-pot reductive acetylation of nitrobenzene.
Figure 11

Reusability of the CuFe2O4 MNPs in the one-pot reductive acetylation of nitrobenzene.

3 Experimental

3.1 Preparation of the CuFe2O4 MNPs

CuFe2O4 MNPs were synthesized based on a previously reported method by Jia and co-workers [76]. First of all, copper(II) acetate, iron(III) nitrate, sodium hydroxide, and sodium chloride were mixed in a molar ratio 1:2:8:2 and grounded in a simple agate mortar and pestle. After about 50 min, the resultant mixture was washed with deionized water several times. After removal of sodium chloride by washing, the wet nanocomposite was dried for 2 h at 80°C. Finally, the powders were calcinated for 2 h at 300, 500, 600, 700, 800, and 900°C to obtain CuFe2O4 MNPs.

3.2 General experimental procedure for the synthesis of N-arylacetamides via N-acetylation of arylamines

To the synthesis of N-phenylacetamide as a representative example, a mixture of aniline (1 mmol, 0.093 g) and H2O (3 mL) was prepared in a round-bottom flask (15 mL) which equipped with a magnetic stirrer. Then, ferromagnetic CuFe2O4 (0.3 mmol, 0.072 g) was added into the reaction flask, and the resulting mixture was stirred at reflux. Subsequently, Ac2O (1 mmol, 0.102 g) was added to the prepared mixture followed by stirring for 1 min at the same temperature conditions. Then, the mixture was cooled to room temperature, and the CuFe2O4 was separated by a magnet from the reaction environment. Then, the reaction mixture was extracted with ethyl acetate (3 × 5 mL). The organic layers were combined and dried over anhydrous Na2SO4. Finally, evaporation of the solvent under reduced pressure afforded the pure N-phenylacetamide which was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopy techniques.

3.3 General procedure for the synthesis of N-arylacetamides via one-pot reductive acetylation of aromatic nitro compounds

As an example, nitrobenzene (1 mmol, 0.123 g) was dissolved in 2 mL of H2O in a 15 mL round-bottom flask which equipped with a magnetic stirrer. Then, CuFe2O4 (1 mmol, 0.237 g) was added, and the mixture was stirred. Then, NaBH4 (2 mmol, 0.075 g) was added, and the resulting mixture was stirred under reflux conditions for 10 min. Completion of the reduction reaction was monitored by TLC using n-CCl4:Et2O (5:2) as an eluent. Afterward, acetic anhydride (1 mmol, 0.102 g) was added to the reaction mixture followed by stirring for an additional 1 min at the same temperature conditions. Afterward, the mixture was cooled to room temperature, and the mentioned nanocomposite was separated by a magnet from the reaction environment. The reaction mixture was extracted with ethyl acetate (3 × 5 mL). The organic layers were combined and dried over anhydrous Na2SO4. Finally, evaporation of the solvent under reduced pressure afforded the pure N-phenylacetamide which was characterized by FT-IR, 1H NMR, and 13C NMR spectroscopy techniques.

4 Conclusions

In this research, we have developed simple, efficient, cost-effective and environmentally benign protocols for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of aromatic nitro compounds promoted by CuFe2O4 MNPs in water at reflux. Use of water as a green solvent, good to excellent yield of desired products, implementation of the cost-effective promoter which can reusable for several runs are advantages of the current protocols for the synthesis of N-arylacetamide derivatives. It is worthy to note that the catalytic applications of the modified and non-modified CuFe2O4 MNPs in various organic transformations under investigations in our lab, and will be reported in due course of the time.

  1. Conflict of interest The authors declare no conflict of interest.

Acknowledgement

Authors gratefully acknowledge the financial support from Urmia University.

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Received: 2018-12-17
Accepted: 2019-05-28
Published Online: 2019-08-06

© 2019 Zeynizadeh et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
https://doi.org/10.1515/gps-2019-0044
Keywords for this article
N-arylacetamide; N-acetylation of arylamine; reductive acetylation of nitroarene; CuFe2O4; green chemistry
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  2. Studies on the preparation and properties of biodegradable polyester from soybean oil
  3. Flow-mode biodiesel production from palm oil using a pressurized microwave reactor
  4. Reduction of free fatty acids in waste oil for biodiesel production by glycerolysis: investigation and optimization of process parameters
  5. Saccharin: a cheap and mild acidic agent for the synthesis of azo dyes via telescoped dediazotization
  6. Optimization of lipase-catalyzed synthesis of polyethylene glycol stearate in a solvent-free system
  7. Green synthesis of iron oxide nanoparticles using Platanus orientalis leaf extract for antifungal activity
  8. Ultrasound assisted chemical activation of peanut husk for copper removal
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  10. Evaluation of the saponin green extraction from Ziziphus spina-christi leaves using hydrothermal, microwave and Bain-Marie water bath heating methods
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  12. Calcined sodium silicate as an efficient and benign heterogeneous catalyst for the transesterification of natural lecithin to L-α-glycerophosphocholine
  13. Synergistic effect between CO2 and H2O2 on ethylbenzene oxidation catalyzed by carbon supported heteropolyanion catalysts
  14. Hydrocyanation of 2-arylmethyleneindan-1,3-diones using potassium hexacyanoferrate(II) as a nontoxic cyanating agent
  15. Green synthesis of hydratropic aldehyde from α-methylstyrene catalyzed by Al2O3-supported metal phthalocyanines
  16. Environmentally benign chemical recycling of polycarbonate wastes: comparison of micro- and nano-TiO2 solid support efficiencies
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  18. Production of value-added chemicals from esterification of waste glycerol over MCM-41 supported catalysts
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  24. Green cyclic acetals production by glycerol etherification reaction with benzaldehyde using cationic acidic resin
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  27. Controllable biosynthesis of silver nanoparticles using actinobacterial strains
  28. Green vegetation: a promising source of color dyes
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  34. Biogenic ZnO nanoparticles: a study of blueshift of optical band gap and photocatalytic degradation of reactive yellow 186 dye under direct sunlight
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  42. A comparative sorption study of Cr3+ and Cr6+ using mango peels: kinetic, equilibrium and thermodynamic
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  44. Use of deep eutectic solvents as catalyst: A mini-review
  45. Microwave-assisted synthesis of pyrrolidinone derivatives using 1,1’-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride in ethylene glycol
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  49. Waste phenolic resin derived activated carbon by microwave-assisted KOH activation and application to dye wastewater treatment
  50. Direct ethanol production from cellulose by consortium of Trichoderma reesei and Candida molischiana
  51. Agricultural waste biomass-assisted nanostructures: Synthesis and application
  52. Biodiesel production from rubber seed oil using calcium oxide derived from eggshell as catalyst – optimization and modeling studies
  53. Study of fabrication of fully aqueous solution processed SnS quantum dot-sensitized solar cell
  54. Assessment of aqueous extract of Gypsophila aretioides for inhibitory effects on calcium carbonate formation
  55. An environmentally friendly acylation reaction of 2-methylnaphthalene in solvent-free condition in a micro-channel reactor
  56. Aegle marmelos phytochemical stabilized synthesis and characterization of ZnO nanoparticles and their role against agriculture and food pathogen
  57. A reactive coupling process for co-production of solketal and biodiesel
  58. Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
  59. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide
  60. Preconcentration of morphine in urine sample using a green and solvent-free microextraction method
  61. Extraction of glycyrrhizic acid by aqueous two-phase system formed by PEG and two environmentally friendly organic acid salts - sodium citrate and sodium tartrate
  62. Green synthesis of copper oxide nanoparticles using Juglans regia leaf extract and assessment of their physico-chemical and biological properties
  63. Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones
  64. Biosynthesis, characterization and anti-microbial activity of silver nanoparticle based gel hand wash
  65. Efficient and selective microwave-assisted O-methylation of phenolic compounds using tetramethylammonium hydroxide (TMAH)
  66. Anticoagulant, thrombolytic and antibacterial activities of Euphorbia acruensis latex-mediated bioengineered silver nanoparticles
  67. Volcanic ash as reusable catalyst in the green synthesis of 3H-1,5-benzodiazepines
  68. Green synthesis, anionic polymerization of 1,4-bis(methacryloyl)piperazine using Algerian clay as catalyst
  69. Selenium supplementation during fermentation with sugar beet molasses and Saccharomyces cerevisiae to increase bioethanol production
  70. Biosynthetic potential assessment of four food pathogenic bacteria in hydrothermally silver nanoparticles fabrication
  71. Investigating the effectiveness of classical and eco-friendly approaches for synthesis of dialdehydes from organic dihalides
  72. Pyrolysis of palm oil using zeolite catalyst and characterization of the boil-oil
  73. Azadirachta indica leaves extract assisted green synthesis of Ag-TiO2 for degradation of Methylene blue and Rhodamine B dyes in aqueous medium
  74. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system
  75. Extraction of phytosterols from melon (Cucumis melo) seeds by supercritical CO2 as a clean technology
  76. Production of uronic acids by hydrothermolysis of pectin as a model substance for plant biomass waste
  77. Biofabrication of highly pure copper oxide nanoparticles using wheat seed extract and their catalytic activity: A mechanistic approach
  78. Intelligent modeling and optimization of emulsion aggregation method for producing green printing ink
  79. Improved removal of methylene blue on modified hierarchical zeolite Y: Achieved by a “destructive-constructive” method
  80. Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water
  81. Optimization of acid catalyzed esterification and mixed metal oxide catalyzed transesterification for biodiesel production from Moringa oleifera oil
  82. Kinetics and the fluidity of the stearic acid esters with different carbon backbones
  83. Aiming for a standardized protocol for preparing a process green synthesis report and for ranking multiple synthesis plans to a common target product
  84. Microstructure and luminescence of VO2 (B) nanoparticle synthesis by hydrothermal method
  85. Optimization of uranium removal from uranium plant wastewater by response surface methodology (RSM)
  86. Microwave drying of nickel-containing residue: dielectric properties, kinetics, and energy aspects
  87. Simple and convenient two step synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone
  88. Biodiesel production from waste cooking oil
  89. The effect of activation temperature on structure and properties of blue coke-based activated carbon by CO2 activation
  90. Optimization of reaction parameters for the green synthesis of zero valent iron nanoparticles using pine tree needles
  91. Microwave-assisted protocol for squalene isolation and conversion from oil-deodoriser distillates
  92. Denitrification performance of rare earth tailings-based catalysts
  93. Facile synthesis of silver nanoparticles using Averrhoa bilimbi L and Plum extracts and investigation on the synergistic bioactivity using in vitro models
  94. Green production of AgNPs and their phytostimulatory impact
  95. Photocatalytic activity of Ag/Ni bi-metallic nanoparticles on textile dye removal
  96. Topical Issue: Green Process Engineering / Guest Editors: Martine Poux, Patrick Cognet
  97. Modelling and optimisation of oxidative desulphurisation of tyre-derived oil via central composite design approach
  98. CO2 sequestration by carbonation of olivine: a new process for optimal separation of the solids produced
  99. Organic carbonates synthesis improved by pervaporation for CO2 utilisation
  100. Production of starch nanoparticles through solvent-antisolvent precipitation in a spinning disc reactor
  101. A kinetic study of Zn halide/TBAB-catalysed fixation of CO2 with styrene oxide in propylene carbonate
  102. Topical on Green Process Engineering
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