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Green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins using dual-frequency ultrasonication

  • Neeraj Vashisth EMAIL logo , Satya Parkash Sharma , Surender Kumar and Aruna Yadav
Published/Copyright: August 1, 2020
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 9 Issue 1

Abstract

Green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins has been carried out in one step by reacting 2-hydroxybenzaldehydes and 2-hydroxyacetophenones with 1-naphthylacetic anhydride and phenylacetic anhydride, respectively, using dual-frequency ultrasonication, i.e. ultrasonic bath of 40 kHz and probe of 20 kHz. The compounds were obtained in very high yield (80–90%) and their structures were confirmed by infrared and nuclear magnetic resonance data.

Keywords: ultrasonication; naphthyl coumarins; 1-naphthylacetic anhydride; 3-phenylcoumarins; phenylacetic anhydride

1 Introduction

Pyrone ring fuses with benzene nucleus to form a class of heterocyclic compounds known as benzopyrones, of which benzo-α-pyrones, commonly called coumarins, comprise a vast class of compounds. Coumarin was first extracted from tonka beans [1] and its derivatives are known to exhibit a variety of medicinal, physicochemical and phytochemical properties [2,3,4,5]. 3-(1-Naphthyl) coumarins were first reported by Spenger et al. [6] and are known for their anticoagulant properties. 3-Phenylcoumarins have diverse applications. They play significant role in photoconduction [7] and exhibit fungicidal [8], anti-HIV6 [9], anti-oxidant, anti-proliferative [10], vasorelaxant and platelet anti-aggregatory activities [11] and also inhibitory activities like inhibition of thromboplastin-induced disseminated intravascular coagulation [12], monoamine oxidase inhibition, [13] etc. Recently, 3-phenylcoumarins have also been studied for their antibacterial properties [14].

Naphthyl coumarins have been synthesised earlier by condensation of 2-methoxybezaldehydes, 2-hydroxybenzaldehydes or 2-hydroxyacetophenone with 1-naphthylacrylonitrile [15], 1-N,N-diethyl(1-naphthyl)acetamide [16] or 1-naphthylacetic anhydride [17]. Phenyl coumarins have been synthesised by condensation of phenyl acetic acid or phenyl acetic anhydride or acetothiomorpholide with 2-hydroxybenzaldehydes using different bases like PhPOCl2/Et3N, K2CO3, etc. and solvents like benzene [18,19,20]. Microwave irradiation has also been used for the synthesis of 3-phenyl and 3-naphthylcoumarins using DMSO as solvent [21]. Another method involves esterification of 2-hydroxybenzaldehydes in the presence of POCl3-pyridine followed by cyclisation of 2-arylacetoxysalicylaldehyde with KOH in pyridine [22]. The methods above have disadvantages like the use of hazardous solvents, longer reaction time, lower yields, etc.

In continuation of our work on the development of simple and efficient routes for the green synthesis of naturally occurring compounds using ultrasonication, we propose to report our efforts towards one-pot green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins using ultrasound irradiation. The reaction rates of various chemical transformations like synthesis of α, β unsaturated compounds [23], 3-substituted indoles [24], oxidation and reduction reactions [25], Mannich-type reactions [26], triazole derivative synthesis [27,28], nanomaterial synthesis [29], Michael addition reactions [30], coupling reactions [31], extraction of caffeine [32], etc. have been enhanced using ultrasound activation.

This great technique has proved to be extraordinary in terms of operational simplicity, selectivity, reaction time, and yield and excludes the use of hazardous chemicals. During the propagation of ultrasonic waves, compressions and rarefactions, i.e. an alternating zone of high pressure and low pressure, are produced due to longitudinal vibrations of molecules. The formation of cavities or bubbles takes place due to low pressure, which expand and finally collapse ferociously during the compression phase producing shock waves. This phenomenon of bubble formation and violent collapsing is referred to as cavitation (see Figure 1) and is responsible for most of the ultrasonic physical and chemical effects [33]. Dual frequency has synergistic effects in comparison to simple ultrasonication as it reduces reaction time [34] and also enhances cavitation effect [35].

Figure 1 Cavitation process.
Figure 1

Cavitation process.

2 Materials and methods

All starting materials and common laboratory chemicals were purchased from commercial sources and used without any purification. Melting points were determined in open capillary tubes and were uncorrected. Proton nuclear magnetic resonance (1H NMR) spectra were recorded on Baker advance (400 MHz) instruments using trimethyl silane (TMS) as an internal standard. Infrared (IR) spectra were recorded on PerkinElmer Fourier transform IR (FT-IR) spectrophotometer. Sonication was performed using an Oscar-make probe sonicator of 20 kHz and Labsoul-make ultrasonic bath of 40 kHz. When combined ultrasound experiments were performed, the probe was immersed in the test tube placed in ultrasonic bath.

2.1 General procedure for the synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins

A mixture of salicylaldehyde (4.0 mmol), 1-naphthylacetic anhydride (4.0 mmol) and activated Ba(OH)2 (C-200-0.5 g) in equimolar mixture of (C2H5OH–H2O) (1:1) (30 mL) was irradiated with dual-frequency ultrasound by keeping the above mixture in ultrasonic bath operating at 40 kHz and simultaneously irradiating 20 kHz frequency from probe-type ultasonicator in the same test tube containing the mixture for 90 min. The progress and completion of reaction were checked by thin-layer chromatography. Then the mixture was poured into cold water and acidified with hydrochloric acid. So formed, the precipitates were filtered, dried and recrystallised from methanol to get 3-(1-naphthyl) coumarin as a colourless solid. A similar reaction between 2-hydroxyacetophenone and 1-naphthylacetic anhydride provided 4-methyl-3-(1-naphthyl) coumarin. Substituted 3-(1-naphthyl) coumarins and 4-methyl-3-(1-naphthyl) coumarins were synthesised, whose structures were confirmed by IR and 1H NMR (CDCl3).

  • 3-(1-Naphthyl)coumarin (Ia)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 7.27–7.94 (m, 12H, Ar–H and H-4).

  • 7-Methyl-3-(1-naphthyl)coumarin (Ib)

    IR (KBr) cm−1: 1,719 (C═O), 1H NMR (CDCl3) δ, ppm: 2.38 (s, 3H, CH3) and 7.31–7.92 (m, 11H, Ar–H and H-4).

  • 8-Methoxy-3-(1-naphthyl)coumarin (Ic)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 3.82 (s, 3H, OCH3) and 7.1–7.84 (m, 11H, Ar–H and H-4).

  • 7-Chloro-3-(1-naphthyl)coumarin (Id)

    IR (KBr) cm−1: 1,719 (C═O), 1H NMR (CDCl3) δ, ppm: 7.28–7.96 (m, 11H, Ar–H and H-4).

  • 7-Bromo-3-(1-naphthyl)coumarin (Ie)

    IR (KBr) cm−1: 1,720 (C═O), 1H NMR (CDCl3) δ, ppm: 7.21–7.95 (m, 11H, Ar–H and H-4).

  • 4-Methyl-3-(1-naphthyl)coumarin (If)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 2.16 (s, 3H, CH3) and 7.30–7.93 (m, 11H, Ar–H and H-4).

  • 7-Chloro-4-methyl-3-(1-naphthyl)coumarin (Ig)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 2.14 (s, 3H, CH3) and 7.39–7.96 (m, 10H, Ar–H and H-4).

    3-Phenylcoumarins were synthesised by reacting 2-hydroxybenzaldehydes with phenylacetic anhydride in activated Ba(OH)2/water–ethanol medium under ultrasound irradiations for 60 min. The method has been used efficiently for preparing various substituted 3-phenylcoumarins whose structures were confirmed by IR and 1H NMR (CDCl3) spectral data.

  • 3-Phenylcoumarin (IIa)

    IR (KBr) cm−1: 1,716 (C═O), 1H NMR (CDCl3) δ, ppm: 7.10–7.66 (m, 10H, Ar–H and H-4).

  • 7-Chloro3-phenylcoumarin (IIb)

    IR (KBr) cm−1: 1,720 (C═O), 1H NMR (CDCl3) δ, ppm: 7.31–7.95 (m, 9H, Ar–H and H-4).

  • 7-Bromo-3-phenylcoumarin (IIc)

    IR (KBr) cm−1: 1,719 (C═O), 1H NMR (CDCl3) δ, ppm: 7.28–7.89 (m, 9H, Ar–H and H-4).

  • 7-Methyl-3-phenylcoumarin (IId)

    IR (KBr) cm−1: 1,719 (C═O), 1H NMR (CDCl3) δ, ppm: 2.23 (s, 3H,CH3), 7.21–7.65 (m, 9H, Ar–H and H-4).

  • 8-Methoxy-3-phenylcoumarin (IIe)

    IR (KBr) cm−1: 1,720 (C═O), 1H NMR (CDCl3) δ, ppm: 3.85 (s, 3H, OCH3), 6.70–7.72 (m, 9H, Ar–H and H-4).

  • 3-(p-Methoxyphenyl)coumarin (IIf)

    IR (KBr) cm−1: 1,720 (C═O), 1H NMR (CDCl3) δ, ppm: 3.84 (s, 3H, OCH3), 6.87–7.79 (m, 8H, Ar–H and H-4).

  • 7-Chloro-3-(p-methoxyphenyl)coumarin (IIg)

    IR (KBr) cm−1: 1,714 (C═O), 1H NMR (CDCl3) δ, ppm: 3.91 (3H, OCH3), 6.99–7.81 (m, 8H, Ar–H and H-4).

  • 7-Bromo-3-(p-methoxyphenyl)coumarin (IIh)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 3.86 (3H, OCH3), 6.98–7.67 (m, 8H, Ar–H and H-4).

  • 7-Methyl-3-(p-methoxyphenyl)coumarin (IIi)

    IR (KBr) cm−1: 1,718 (C═O), 1H NMR (CDCl3) δ, ppm: 3.85 (s, 3H, OCH3), 2.22 (s, 3H, CH3), 6.95–7.82 (m, 8H, Ar–H and H-4).

  • 8-Methoxy-3-(p-methoxyphenyl)coumarin (IIj)

IR (KBr) cm−1: 1,716 (C═O), 1H NMR (CDCl3) δ, ppm: 3.84, 3.90 (2s, 3H each, 2 OCH3), 6.89–7.77 (m, 8H, Ar–H and H-4).

3 Results

A mixture of salicylaldehyde, 1-naphthylacetic anhydride and Ba(OH)2 in equimolar mixture of (C2H5OH–H2O) (1:1) (30 mL) was irradiated with dual-frequency ultrasound for 90 min using an ultrasonic bath (40 kHz) and probe (20 kHz; see Scheme 1). The progress of reaction was checked with the help of thin-layer chromatography. After workup, the compound was separated out and recrystallised with methanol. The melting point of the compound thus obtained was 153–154°C; and in IR, it showed absorption at 1,718 cm−1, which are assigned to C═O stretching frequency. In 1H NMR, it showed multiplet at 7.27–7.94 due to 12 protons (Ar–H and H-4). Based on the data, it was found that the compound was 3-(1-naphthyl) coumarin and its derivatives were prepared (see Table 1).

Scheme 1 Synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins.
Scheme 1

Synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins.

Table 1

Characterisation of data of compounds I (a–g)

CompoundRR1R2M.Pt. (lit) (°C)IR (cm−1): (C═O)Yield (%)1H NMR (CDCl3) δ (ppm)
IaHHH153–154 (154–155) [17]1,718857.27–7.94 (m, 12H, Ar–H and H-4)
IbHHCH3131–132 (132–133) [17]1,719802.38 (s, 3H, CH3) and 7.31–7.92(m, 11H, Ar–H and H-4)
IcHOCH3H149–150 (151–153) [17]1,718803.82 (s, 3H, OCH3) and 7.1–7.84 (m, 11H, Ar–H and H-4)
IdHHCl152–154 (153–154) [17]1,719847.28–7.96 (m, 11H, Ar–H and H-4)
IeHHBr123–125 (126–127) [17]1,720827.21–7.95 (m, 11H, Ar–H and H-4)
IfCH3HH187–189 (188–90) [17]1,718822.16 (s, 3H, CH3) and 7.30–7.93 (m, 11H, Ar–H and H-4)
IgCH3HCl184–186 (185–186) [17]1,718842.14 (s, 3H, CH3) and 7.39–7.96 (m, 10H, Ar–H and H-4)

A similar reaction between 2-hydroxyacetophenone and 1-naphthylacetic anhydride provided 4-methyl-3-(1-naphthyl) coumarin. 3-Phenylcoumarins were also prepared by reacting 2-hydroxybenzaldehydes with phenylacetic anhydrides (Scheme 2). 3-Phenylcoumarin showed IR absorption at 1,716 cm−1 and 1H NMR multiplet at 7.10–7.66 due to 10 protons. Using the above procedure, various compounds were synthesised (see Table 2).

Scheme 2 Synthesis of 3-phenylcoumarins.
Scheme 2

Synthesis of 3-phenylcoumarins.

Table 2

Characterisation of data of compounds II(a–j)

CompoundRR1R2M.Pt. (lit) (°C)IR (cm−1): (C═O)Yield (%)1H NMR (CDCl3) δ (ppm)
IIaHHH139–40 (140–141) [21]1,716867.10–7.66 (m, 10H, Ar–H and H-4)
IIbHHCl194–196 (195–196) [21]1,720907.31–7.95 (m, 9H, Ar–H and H-4)
IIcHHBr195–196 (194–196) [21]1,719877.28–7.89 (m, 9H, Ar–H and H-4)
IIdHHCH3141–44 (144–45) [21]1,719852.23 (s, 3H,CH3), 7.21–7.65 (m, 9H, Ar–H and H-4)
IIeHOCH3H121–123 (122–123) [36]1,720803.85 (s, 3H, OCH3), 6.70–7.72 (m, 9H, Ar–H and H-4)
IIfOCH3HH141–142 (143–144) [21]1,720823.84 (s, 3H, OCH3), 6.87–7.79 (m, 8H, Ar–H and H-4)
IIgOCH3HCl190–191 (190–192) [21]1,714833.91 (3H, OCH3), 6.99–7.81 (m, 8H, Ar–H and H-4)
IIhOCH3HBr200–202 (201–202) [21]1,718843.86 (3H, OCH3), 6.98–7.67 (m, 8H, Ar–H and H-4).
IIiOCH3HCH3140–142 (142–143) [21]1,718823.85 (s, 3H, OCH3), 2.22 (s, 3H, CH3), 6.95–7.82 (m, 8H, Ar–H and H-4).
IijOCH3OCH3H184–185 (185–186) [21]1,716803.84, 3.90 (2 s, 3H each, 2 OCH3), 6.89–7.77 (m, 8H, Ar–H and H-4)

4 Conclusions

To sum up, we have developed an effective procedure for one-pot green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins, without the use of toxic reagents and solvents. The synergistic effect of the combined use of 40 kHz ultrasonic bath and 20 kHz probe resulted in only one final purification step, reduced reaction time, and increased yields. It is conclusively observed that rapid synthesis of coumarins is one of the potential applications of this method.

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Received: 2020-03-18
Revised: 2020-06-23
Accepted: 2020-06-30
Published Online: 2020-08-01

© 2020 Neeraj Vashisth et al., published by De Gruyter

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

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  30. Adsorption of l-α-glycerophosphocholine on ion-exchange resin: Equilibrium, kinetic, and thermodynamic studies
  31. Microwave-assisted green synthesis of silver nanoparticles using dried extracts of Chlorella vulgaris and antibacterial activity studies
  32. Preparation of graphene oxide/chitosan complex and its adsorption properties for heavy metal ions
  33. Green synthesis of metal and metal oxide nanoparticles from plant leaf extracts and their applications: A review
  34. Synthesis, characterization, and electrochemical properties of carbon nanotubes used as cathode materials for Al–air batteries from a renewable source of water hyacinth
  35. Optimization of medium–low-grade phosphorus rock carbothermal reduction process by response surface methodology
  36. The study of rod-shaped TiO2 composite material in the protection of stone cultural relics
  37. Eco-friendly synthesis of AuNPs for cutaneous wound-healing applications in nursing care after surgery
  38. Green approach in fabrication of photocatalytic, antimicrobial, and antioxidant zinc oxide nanoparticles – hydrothermal synthesis using clove hydroalcoholic extract and optimization of the process
  39. Green synthesis: Proposed mechanism and factors influencing the synthesis of platinum nanoparticles
  40. Green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins using dual-frequency ultrasonication
  41. Optimization for removal efficiency of fluoride using La(iii)–Al(iii)-activated carbon modified by chemical route
  42. In vitro biological activity of Hydroclathrus clathratus and its use as an extracellular bioreductant for silver nanoparticle formation
  43. Evaluation of saponin-rich/poor leaf extract-mediated silver nanoparticles and their antifungal capacity
  44. Propylene carbonate synthesis from propylene oxide and CO2 over Ga-Silicate-1 catalyst
  45. Environmentally benevolent synthesis and characterization of silver nanoparticles using Olea ferruginea Royle for antibacterial and antioxidant activities
  46. Eco-synthesis and characterization of titanium nanoparticles: Testing its cytotoxicity and antibacterial effects
  47. A novel biofabrication of gold nanoparticles using Erythrina senegalensis leaf extract and their ameliorative effect on mycoplasmal pneumonia for treating lung infection in nursing care
  48. Phytosynthesis of selenium nanoparticles using the costus extract for bactericidal application against foodborne pathogens
  49. Temperature effects on electrospun chitosan nanofibers
  50. An electrochemical method to investigate the effects of compound composition on gold dissolution in thiosulfate solution
  51. Trillium govanianum Wall. Ex. Royle rhizomes extract-medicated silver nanoparticles and their antimicrobial activity
  52. In vitro bactericidal, antidiabetic, cytotoxic, anticoagulant, and hemolytic effect of green-synthesized silver nanoparticles using Allium sativum clove extract incubated at various temperatures
  53. The green synthesis of N-hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines with acidic ionic liquid as catalyst
  54. Effect of KMnO4 on catalytic combustion performance of semi-coke
  55. Removal of Congo red and malachite green from aqueous solution using heterogeneous Ag/ZnCo-ZIF catalyst in the presence of hydrogen peroxide
  56. Nucleotide-based green synthesis of lanthanide coordination polymers for tunable white-light emission
  57. Determination of life cycle GHG emission factor for paper products of Vietnam
  58. Parabolic trough solar collectors: A general overview of technology, industrial applications, energy market, modeling, and standards
  59. Structural characteristics of plant cell wall elucidated by solution-state 2D NMR spectroscopy with an optimized procedure
  60. Sustainable utilization of a converter slagging agent prepared by converter precipitator dust and oxide scale
  61. Efficacy of chitosan silver nanoparticles from shrimp-shell wastes against major mosquito vectors of public health importance
  62. Effectiveness of six different methods in green synthesis of selenium nanoparticles using propolis extract: Screening and characterization
  63. Characterizations and analysis of the antioxidant, antimicrobial, and dye reduction ability of green synthesized silver nanoparticles
  64. Foliar applications of bio-fabricated selenium nanoparticles to improve the growth of wheat plants under drought stress
  65. Green synthesis of silver nanoparticles from Valeriana jatamansi shoots extract and its antimicrobial activity
  66. Characterization and biological activities of synthesized zinc oxide nanoparticles using the extract of Acantholimon serotinum
  67. Effect of calcination temperature on rare earth tailing catalysts for catalytic methane combustion
  68. Enhanced diuretic action of furosemide by complexation with β-cyclodextrin in the presence of sodium lauryl sulfate
  69. Development of chitosan/agar-silver nanoparticles-coated paper for antibacterial application
  70. Preparation, characterization, and catalytic performance of Pd–Ni/AC bimetallic nano-catalysts
  71. Acid red G dye removal from aqueous solutions by porous ceramsite produced from solid wastes: Batch and fixed-bed studies
  72. Review Articles
  73. Recent advances in the catalytic applications of GO/rGO for green organic synthesis
https://doi.org/10.1515/gps-2020-0042
Keywords for this article
ultrasonication; naphthyl coumarins; 1-naphthylacetic anhydride; 3-phenylcoumarins; phenylacetic anhydride
Creative Commons
BY 4.0

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  28. Catalytic performance of the biosynthesized AgNps from Bistorta amplexicaule: antifungal, bactericidal, and reduction of carcinogenic 4-nitrophenol
  29. Optical and antimicrobial properties of silver nanoparticles synthesized via green route using honey
  30. Adsorption of l-α-glycerophosphocholine on ion-exchange resin: Equilibrium, kinetic, and thermodynamic studies
  31. Microwave-assisted green synthesis of silver nanoparticles using dried extracts of Chlorella vulgaris and antibacterial activity studies
  32. Preparation of graphene oxide/chitosan complex and its adsorption properties for heavy metal ions
  33. Green synthesis of metal and metal oxide nanoparticles from plant leaf extracts and their applications: A review
  34. Synthesis, characterization, and electrochemical properties of carbon nanotubes used as cathode materials for Al–air batteries from a renewable source of water hyacinth
  35. Optimization of medium–low-grade phosphorus rock carbothermal reduction process by response surface methodology
  36. The study of rod-shaped TiO2 composite material in the protection of stone cultural relics
  37. Eco-friendly synthesis of AuNPs for cutaneous wound-healing applications in nursing care after surgery
  38. Green approach in fabrication of photocatalytic, antimicrobial, and antioxidant zinc oxide nanoparticles – hydrothermal synthesis using clove hydroalcoholic extract and optimization of the process
  39. Green synthesis: Proposed mechanism and factors influencing the synthesis of platinum nanoparticles
  40. Green synthesis of 3-(1-naphthyl), 4-methyl-3-(1-naphthyl) coumarins and 3-phenylcoumarins using dual-frequency ultrasonication
  41. Optimization for removal efficiency of fluoride using La(iii)–Al(iii)-activated carbon modified by chemical route
  42. In vitro biological activity of Hydroclathrus clathratus and its use as an extracellular bioreductant for silver nanoparticle formation
  43. Evaluation of saponin-rich/poor leaf extract-mediated silver nanoparticles and their antifungal capacity
  44. Propylene carbonate synthesis from propylene oxide and CO2 over Ga-Silicate-1 catalyst
  45. Environmentally benevolent synthesis and characterization of silver nanoparticles using Olea ferruginea Royle for antibacterial and antioxidant activities
  46. Eco-synthesis and characterization of titanium nanoparticles: Testing its cytotoxicity and antibacterial effects
  47. A novel biofabrication of gold nanoparticles using Erythrina senegalensis leaf extract and their ameliorative effect on mycoplasmal pneumonia for treating lung infection in nursing care
  48. Phytosynthesis of selenium nanoparticles using the costus extract for bactericidal application against foodborne pathogens
  49. Temperature effects on electrospun chitosan nanofibers
  50. An electrochemical method to investigate the effects of compound composition on gold dissolution in thiosulfate solution
  51. Trillium govanianum Wall. Ex. Royle rhizomes extract-medicated silver nanoparticles and their antimicrobial activity
  52. In vitro bactericidal, antidiabetic, cytotoxic, anticoagulant, and hemolytic effect of green-synthesized silver nanoparticles using Allium sativum clove extract incubated at various temperatures
  53. The green synthesis of N-hydroxyethyl-substituted 1,2,3,4-tetrahydroquinolines with acidic ionic liquid as catalyst
  54. Effect of KMnO4 on catalytic combustion performance of semi-coke
  55. Removal of Congo red and malachite green from aqueous solution using heterogeneous Ag/ZnCo-ZIF catalyst in the presence of hydrogen peroxide
  56. Nucleotide-based green synthesis of lanthanide coordination polymers for tunable white-light emission
  57. Determination of life cycle GHG emission factor for paper products of Vietnam
  58. Parabolic trough solar collectors: A general overview of technology, industrial applications, energy market, modeling, and standards
  59. Structural characteristics of plant cell wall elucidated by solution-state 2D NMR spectroscopy with an optimized procedure
  60. Sustainable utilization of a converter slagging agent prepared by converter precipitator dust and oxide scale
  61. Efficacy of chitosan silver nanoparticles from shrimp-shell wastes against major mosquito vectors of public health importance
  62. Effectiveness of six different methods in green synthesis of selenium nanoparticles using propolis extract: Screening and characterization
  63. Characterizations and analysis of the antioxidant, antimicrobial, and dye reduction ability of green synthesized silver nanoparticles
  64. Foliar applications of bio-fabricated selenium nanoparticles to improve the growth of wheat plants under drought stress
  65. Green synthesis of silver nanoparticles from Valeriana jatamansi shoots extract and its antimicrobial activity
  66. Characterization and biological activities of synthesized zinc oxide nanoparticles using the extract of Acantholimon serotinum
  67. Effect of calcination temperature on rare earth tailing catalysts for catalytic methane combustion
  68. Enhanced diuretic action of furosemide by complexation with β-cyclodextrin in the presence of sodium lauryl sulfate
  69. Development of chitosan/agar-silver nanoparticles-coated paper for antibacterial application
  70. Preparation, characterization, and catalytic performance of Pd–Ni/AC bimetallic nano-catalysts
  71. Acid red G dye removal from aqueous solutions by porous ceramsite produced from solid wastes: Batch and fixed-bed studies
  72. Review Articles
  73. Recent advances in the catalytic applications of GO/rGO for green organic synthesis
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