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Preconcentration of morphine in urine sample using a green and solvent-free microextraction method

  • Bamdad Riahi-Zanjani , Mahdi Balali-Mood , Zarrin Es’haghi , Ahmad Asoodeh and Adel Ghorani-Azam EMAIL logo
Published/Copyright: May 25, 2019
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 8 Issue 1

Abstract

The ability of extraction and preconcentration of small amounts of substances from biological samples is very important in medical toxicology. On the other hand, minimal use of organic solvents is an important issue to prevent environmental damage. In the present study, we developed a new solid phase microextraction fiber using plant extracts as sorbent for extraction and preconcentration of morphine in urine sample. For this purpose, raw carbon nanotubes (CNTs) were functionalized with tobacco extracts. Functionalization was confirmed by Fourier transform infrared (FTIR) and Raman spectroscopy in addition to scanning electron microscope (SEM) images. The functionalized CNTs were coated on polypropylene hollow fiber. The results of HPLC analysis showed that the produced fiber could preconcentrate a very low concentration of morphine (0.25 ng/ml) in small volume of urine samples. Limit of detection (LOD) and limit of quantification (LOQ) for the produced fiber were determined 0.25 ng/ml and 0.825 ng/ml, respectively, and recovery of the fiber was determined 89% at LOQ. The produced fiber provided a recyclable and solvent free method for extraction of a trace amount of morphine, which can be successfully used for up to 30 times with no significant loss in the extraction efficiency.

Keywords: HPLC; plant; green chemistry; morphine; nanocomposite; preconcentration; hollow fiber-solid phase microextraction (HF-SPME)

1 Introduction

All drugs are metabolized in the body and most of them have half-life of less than 72 h, so there is a limited time for detection of the drugs in biological samples [1]. Also, since the considerable forensic decisions are made on the basis of the levels of analytes in biological samples, accuracy of the detection method in appropriate time is critical [2]. There are numerous confirmatory methods for detection of analytes in biological samples such as HPLC, and GC-mass. Preconcentration of the analytes during conventional sample preparation is considered as an essential part of analyte detection in these methods [3]. However, sample preparation has some drawbacks such as high solvent use and subsequent environmental damage. Preconcentration methods with good efficiency such as microextraction techniques have been developed for detection of small amount of analytes. Solid phase microextraction (SPME) method is considered as a method of desire for extraction of small amount of abused drugs [4,5].

Although microextraction techniques may enhance the sample preparation methods, they are usually associated with some disadvantage such as noncompatibility with biological system [6,7]. Many of the chemicals used in the microextraction methods are not biodegradable and may be dangerous and cause environmental damage [8]. Plants extracts and herbal products are generally considered as a promising therapeutic option for treatment of various diseases [9,10]. But in recent years, it is believed that herbal products can be used as sorbent in diagnostic medicine and biosensor technology. In this regards, it is now believed that using environmentally safe method such as plant-based sorbent may enhance the safety of sample preparation as well as the efficiency of extraction method in analytical sciences.

Recently, plant extract or other herbal products have attracted attentions for use in diagnostic purposes. Since, tobacco extracts contain numerous types of active constituents such as terpenes, alcohols, and polyphenols with different functional groups, including carboxylic acids, and nitrogen-containing compounds, it is expected that morphine can efficiently bind to the nanofiber functionalized with tobacco extract. Hence, in this study, we aimed to develop a SPME fiber for preconcentration and detection of morphine in urine sample using tobacco extract as the sorbent. In addition, we aimed to develop a green and solvent free method for preconcentration of morphine without any time-consuming sample preparation.

2 Materials and methods

2.1 Chemicals and apparatus

Chemicals including acetone, N,N-Dimethylformamide (DMF), 1-octanol, and acetonitrile (ACN) were purchased from Merck (Darmstadt, Germany). Morphine was obtained from a collaborator laboratory of Mashhad University of medical sciences, Mashhad, Iran. A standard solution of morphine with a concentration of 1000 ng/ml in deionized water was provided and then stored at 4°C until analysis. HPLC-grade water and acetonitrile were purchased from Merck.

A Fourier-transform infrared spectrophotometer (FTIR-8400S, Shimadzu, Japan) and a Raman spectrophotometer (Teksan, Takram P50C0R10, with an excitation wavelength of 532 nm) were used to respectively investigate the functional groups of the synthesized nanomaterials and successful modification of the carbon nanotubes (CNTs). To evaluate the structure of the produced fiber in addition to the synthesized nanomaterial, a scanning electron microscope (SEM) (TESCAN MIRA3-FEG, Czech Republic) was used. Moreover, to measure pH values of the solutions a digital pH meter with glass electrode (Metrohm-744, Switzerland) was applied. All experiments were performed in triplicate at room temperature (22 ± 0.5°C), otherwise it is stated.

2.2 Extraction of tobacco products

Tobacco products were extracted by sonication of the tobacco leaves in ultrasonic bath. For this purpose, 50 g dried tobacco leaves were washed with deionized water and then were sonicated in ultrasonic bath at 60°C for 8 h. Afterwards, the extracts were filtered through 0.45 μm polytetrafluoroethylene (PTFE) membrane and then lyophilized and kept at 4°C for subsequent uses.

2.3 Synthesis of nanomaterial

The nanotubes were carboxylated prior to functionalization as previously described [4]. For synthesis of nanomaterial, the carboxylated CNTs were functionalized with the lyophilized tobacco extracts. For this purpose, 20 mg CNTs and 5 mg herbal products (lyophilized tobacco extracts) were dissolved in DMF (10 ml) and sonicated for 1 h at 60°C. Subsequently, 10 mg sodium nitrite (NaNO2) was added to the solution and sonicated for additional 12 h. The resulted materials were then filtered through 0.45 μm PTFE membrane and washed twice with deionized water. Afterwards, the synthesized nanomaterials were dried overnight at 50°C under vacuum and used in the study.

2.4 Preparation of nanomaterial reinforced hollow fiber

To improve the stability of fibers in addition to other benefits such as simplicity, and selectivity of microextraction technique, hollow fiber (HF) was used for production of SPME fiber. HF is a porous polypropylene fiber with 200 μm thickness and the inner diameter of 600 μm. Hence on structural point of view, the adsorption of analytes may increase in HFs, since adsorption can occur at both inner and outer space of the fiber. For this purpose, HFs were sonicated in acetone for 5 min to remove the impurities as well as other possible contaminations and then sonicated in octanol for 20 min. The synthesized nanomaterials was added to the solution and sonication was continued for 6 h at 45°C, so that the inner side as well as the pores and the surface of HFs were coated with the synthesized nanomaterials functionalized with the tobacco products. The fibers were then dried for use.

2.5 Sample preparation and HPLC analysis

For sample preparation, a serial dilution of morphine (0.1-100 ng/ml) was prepared in urine. For adsorption of the morphine, the fiber was inserted into the sample and sonicated for 5 min. Afterwards, the fiber was washed with 200 μl of the washing solution containing water/methanol (80/20) by sonication for 2 min. To optimize the

microextraction process, functionality of the fiber was evaluated at a range of pH (4-12) and temperature (10°C-50°C) and in the absence or presence of the salts (NaCl and CaCl2). HPLC (Knauer, Berlin, Germany) system with C18 HPLC column (10 × 250 mm) was used to measure the preconcentrated morphine in urine sample. Since the retention times of morphine is 4.3-5 min, HPLC analysis was performed over a period of 10 min in isocratic mode. Acetonitrile-sodium acetate (10:90, v/v; sodium acetate buffer 0.01 M; pH 4) was used as the mobile phase with a flow rate of 0.6 ml/min. According to UV-Visible spectrophotometer measurements, the UV detection wavelength was set at 285 nm.

3 Results

3.1 Characterization and morphology of the synthesized nanocomposite

Physiochemical properties of the synthesized nanomaterial including successful functionalization and the size of nanomaterials were confirmed by FTIR analysis, Raman measurements and SEM imaging, respectively. Microscopic analysis revealed that the nanocomposites are homogeneously distributed, and functionalized with molecules that have amine, carbonyl, hydroxyl and other functional groups as confirmed by FTIR spectroscopic technique. FTIR spectra showed that functionalization of the synthesized nanocomposite has been successfully completed (Figure 1). The peak at 3537 cm-1 corresponds to OH group. Amide bound (NH stretch) was shown at 3439 cm-1. In addition, a frequency at 1727 was attributed to C=O group of amide bound. Also, the peak at 1686 cm-1 is a result of formation of amide (C=O stretch). Raman measurements also confirmed that the structure of CNTs have been modified after carboxylation and functionalization. According to the data of Raman measurements, changes in intensities of the peaks related to the defects in the graphitic structure (D), and tangential vibration of the carbon atoms of the nanotube (G) indicated modification of CNTs (Figure 2). SEM images also showed the homogenous structure of the nanocomposite and microstructure of the fiber (Figures 3a and 3b).

Figure 1 FTIR spectra of the carbon nanotube functionalized with tobacco extract.
Figure 1

FTIR spectra of the carbon nanotube functionalized with tobacco extract.

Figure 2 Raman spectra of the raw CNT, carboxylated CNT and tobacco-functionalized CNT.
Figure 2

Raman spectra of the raw CNT, carboxylated CNT and tobacco-functionalized CNT.

Figure 3 SEM image of the carbon nanotube functionalized with tobacco extract (a), and microstructure of the hallow fiber (b).
Figure 3

SEM image of the carbon nanotube functionalized with tobacco extract (a), and microstructure of the hallow fiber (b).

3.2 Detection of morphine in urine sample and optimization of microextraction process

For detection of the preconcentrated morphine by HPLC, 15 μl of the solution was injected into HPLC system. HPLC data showed that, without microextraction process, morphine could not be detected in urine samples containing lower concentration of morphine (≤10 ng/ml). However, microextraction with the produced fiber could concentrate the morphine by more than 20-fold, since 0.25 ng/ml of morphine in urine sample was also detectable after microextraction.

The efficiency of microextraction was evaluated at different environmental conditions including temperature, pH, extraction time, and the presence of salts. The results showed that the optimum condition for microextraction was 5 min at 40°C in sonication bath (Figures 4a and 4b). On the other hand, our findings showed that salt such as NaCl, and CaCl2 reduces the efficiency of microextraction process (Figure 4c). The results also showed that the morphine can more efficiently bind to the fiber at neutral pH of around pH = 6 (Figure 4d). In addition, the prepared nanofiber showed a suitable stability at the defined conditions (optimum pH, temperature, time of extraction, and without salt), where the fiber was used for 30 times with no considerable loss in its extraction efficiency.

Figure 4 Effect of time (a), temperature (b), salts (c), and pH (d) on microextration efficiency of the SPME fiber.
Figure 4

Effect of time (a), temperature (b), salts (c), and pH (d) on microextration efficiency of the SPME fiber.

3.3 Validation of the produced fiber in real sample

To investigate the validity of the produced fiber performance in real samples, morphine-positive urine samples from patients admitted to the poisoned patients department of Imam Reza hospital, Mashhad, Iran, which had been subjected to be discarded were collected and applied to morphine detection. Findings confirmed that the produced fiber can preconcentrate the morphine in urine samples (Figures 5a and 5b). The results also demonstrated that adsorption of morphine to the fiber in morphine-positive urine samples tracks a linear range at two levels (0.25-10 ng/ml and 10-1000 ng/ml). Furthermore, limit of quantification (LOQ) and the limit of detection (LOD) were found to be 0.825 and 0.25 ng/ml, respectively. Recovery of the fiber was also measured 89% at LOQ level.

Figure 5 HPLC chromatograms of the morphine preconcentrated with the SPME method. The chromatograms show morphine peak before (a) and after microextraction (b).
Figure 5

HPLC chromatograms of the morphine preconcentrated with the SPME method. The chromatograms show morphine peak before (a) and after microextraction (b).

4 Discussion

Detection of small amount of analytes in biological samples is of great importance particularly in forensic medicine. This is particularly important when only a small amount of analyte is available in biological sample due to taking a low-dose of the drugs or even passing a long time after the last taking of the medication [11,12]. Extraction and preconcentration is promising approach for detection of these trace analytes; however, this method has some shortcoming such as non-biodegradability and non-biocompatibility with the environment. Moreover, a comprehensive global effort has been recently started to reduce hazardous wastes of chemical origin in addition to developing

economical, cost-effective, and safe method for analysis of chemicals and toxicants in the reference laboratories as well as in clinical practices for diagnostic purposes [13]. In addition, to overcome the disadvantages of routine microextraction technique, recent studies have focused on developing green methods with the lowest solvent use as possible using biocompatible nanomaterials [14]. For this reason, plant extracts or other purified herbal products are the era of interest for many researchers in green chemistry or diagnostic medicine, and recent findings showed that herbal products or plant extract can be used at different stages of method development [15,16]. In the present study, tobacco extracts containing different products with various functional groups were used as sorbent of morphine in the sample. The use of plant extract as a selective sorbent for microextraction and preconcentration of cadmium as a trace analyte in the water and fruit samples had been previously reported [17]. Also, the advantages of green extraction method using herbal products over chemical methods have been emphasized. Theoretically, the main purpose of green extraction method is developing new extraction processes or new alternative solvents using renewable and biodegradable plant resources to minimize hazardous chemical wastes [18]. Some of the most important advantages of plant-based analyte extraction in comparison with conventional chemical methods include fewer environmental damages due to fewer solvent use, cost-effective procedure especially in mass production, and no further necessity to use high temperature, pressure, and other hazardous chemicals during preparation of the fiber [19].

Nowadays, plant-based extraction techniques are used for extraction and preconcentration of high-quality natural products from plant in addition to their byproducts [20, 21, 22]. It has been reported that biodegradable aminophenol-functionalized resin can be used for green determination and preconcentration of metal ions including copper (Cu), zinc (Zn), lead (Pb) and cadmium (Cd) in drinking tap water [23]. Solid phase extraction and preconcentration method using a natural sorbent based on cotton roll dyed by quinalizarin has also been successfully applied for determination of 14 rare earth elements as well as uranium with acceptable accuracy, precision and significant enrichment factor [24]. Other environmental friendly method has also been successfully used for preconcentration and

simultaneous determination of cobalt (Co) and lead (Pb) in waste water sample using 8-hydroxyquinoline (oxine) as a chelating agent [25].

So far, plant extract or herbal products have not been used as sorbent for separation or analytical purpose. In the present study, a new SPME fiber was designed and produced that was recyclable after the extraction process is completed. Also, since non-chemical agents of plant origin was used for preparation of the fiber, it can be considered as less hazardous to the environment as well as the operators. Findings showed that the produced fiber could efficiently adsorb the morphine in the water and urine samples. Specificity of the fiber to the morphine was relatively high, since by increasing the concentration of morphine in the urine sample, morphine molecules were more successful in competition with other analytes present in the urine. This could be partly due to higher binding affinity of morphine to the surface sorbent of the produced fiber. Findings of the current research may help to develop a new green and solvent-free method for extraction of analytes, especially drugs of abuse.

5 Conclusion

Findings of the current study suggested that the provide method could improve the efficiency of morphine detection. In addition, the described method is a green analytical method with the lowest use of chemical solution in which a biodegradable fiber could be used for several times with no significant loss in concentrating capacity.

Acknowledgment

The results described in this paper were parts of PhD thesis in toxicology, supported by the Vice Chancellor for Research of Mashhad University of Medical Sciences with grant No: 930829.

  1. Conflict of interest: There is no conflict of interest between the authors.

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Received: 2018-10-10
Accepted: 2019-03-26
Published Online: 2019-05-25
Published in Print: 2019-01-28

© 2019 Riahi-Zanjani et al., published by De Gruyter

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

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  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-2019-0023
Keywords for this article
HPLC; plant; green chemistry; morphine; nanocomposite; preconcentration; hollow fiber-solid phase microextraction (HF-SPME)
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  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
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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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  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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  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
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  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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