Startseite Magnetically separable Ru-containing catalysts in supercritical deoxygenation of fatty acids
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Magnetically separable Ru-containing catalysts in supercritical deoxygenation of fatty acids

  • Antonina A. Stepacheva , Yury V. Lugovoy , Oleg V. Manaenkov , Alexander I. Sidorov , Valentina G. Matveeva , Mikhail G. Sulman und Esther M. Sulman EMAIL logo
Veröffentlicht/Copyright: 27. Dezember 2019
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Pure and Applied Chemistry
Aus der Zeitschrift Pure and Applied Chemistry Band 92 Heft 6

Abstract

In the current paper, the possibility of the use of magnetically separable catalysts containing ruthenium oxide species in the supercritical deoxygenation of stearic acid for producing of the second generation of biodiesel is reported. Three different supports (silica, ceria, and hypercrosslinked polystyrene) were used for the stabilization of magnetic nanoparticles (MNPs) and Ru-containing particles. The effect of support on the magnetic properties as well as the catalytic activity of the obtained systems was studied. All synthesized catalysts were shown to provide high stearic acid conversion (up to 95 %). The highest yield of C17+ hydrocarbons (up to 86 %) was observed while using the Ru–Fe3O4-HPS system. Ru–Fe3O4-HPS was characterized by the high values of the specific surface area (364 m2/g) and saturation magnetization (4.5 emu/g). The chosen catalytic system was found to maintain its catalytic activity for a minimum of 10 consecutive cycles.

Keywords: ceria; deoxygenation; hypercrosslinked polystyrene; magnetite; MMC-18; MNPs; silica; supercritical hexane

Introduction

Mineral fossil depletion and increasing demands in transportation fuels make the researchers to develop novel routes for renewable fuel production. Last decades the synthesis of the second generation of biodiesel (bio-jet, green diesel) through deoxygenation of fatty acids and their derivatives is of great attention [1], [2], [3]. This process results in the obtaining of liquid diesel fuel characterized by low acidity and viscosity as well as high cetane number (up to 99) [4]. Deoxygenation forms diesel-range hydrocarbons through the removal of oxygen from fatty acid molecules in the presence of either transition metal sulfides, nitrides, phosphides, and oxides, or noble-metal-based catalysts [4], [5], [6], [7], [8], [9], [10], [11].

However, current problems of deoxygenation process, such as catalyst stability and selectivity and high hydrogen consumption as well as rather harsh conditions, require the development of novel approaches. One such perspective ways consist of the use of supercritical solvents for the conversion of fatty acids into the hydrocarbons. The use of supercritical fluids as a medium for the deoxygenation process can significantly decrease the process temperature as well as reaction time. In addition, some compounds such as light hydrocarbons, alcohols, and water in the supercritical state can serve as a hydrogen atom donor [10], [12], [13], [14]. The last property of supercritical fluids allows the problem of hydrogen consumption to be solved. Nowadays, supercritical water, carbon dioxide, propane, and hexane are most commonly used [15], [16], [17], [18], [19]. Hexane in the supercritical state is promised to be the most optimal medium for deoxygenation process because it has a relatively low critical point (Tc=234.5°C, Pc=3.02 MPa) and good miscibility with oils at room conditions [19]. Recently we have also reported the successful application of supercritical hexane in the deoxygenation of stearic acid [20], [21], [22]. Taking into account the cracking reactions which can proceed during the supercritical deoxygenation, the search of the catalysts accelerating the decarboxylation process is an important task.

Nowadays, catalysts with magnetic properties are of great attention. These properties minimize the catalyst loss and allow the catalyst to be fully recovered from the reaction mixture [23]. Moreover, the catalysts containing magnetic nanoparticles (MNPs) are characterized by the high specific surface area and enhanced catalytic activity due to the presence of Fe, Ni or Co-containing particles [24]. The magnetically separable catalysts have been successfully applied in biomass conversion into biofuels and chemicals [25], [26], [27]. There are several reports on the use of catalysts with magnetic properties in cellulose hydrolysis [28], [29] and hydrogenolysis [30], [31], [32], [33], [34]. MNPs are widely used as acid-base catalyst support for transesterification reactions producing the first generation of biodiesel [35], [36], [37], [38], [39], [40], [41], [42]. Recently the use of magnetically separable catalysts in hydrodeoxygenation of lignin monomers and fatty acids was reported [43], [44]. The main problems in the application of MNPs in catalytic reactions are their stabilization and prevention of aggregation as well as high sensitivity to the air oxidation [45], [46]. For these purposes, different approaches such as coating of MNPs by silica or carbon are used [47], [48], [49], [50], [51], [52], [53]. The use of different porous materials as supports is another way to stabilize the MNPs [30], [31], [32], [33], [34], [37], [38], [39], [46], [47], [56]. Moreover, the incorporation of noble metals is widely applied in order to enhance the catalytic activity of magnetically based materials [31], [34], [47], [54], [55], [56], [57]. Here we describe the possibility of the use of magnetically recoverable Ru-containing catalysts stabilized in different supports (silica, ceria, hypercrosslinked polystyrene (HPS)) in the catalytic deoxygenation of stearic acid in the medium of supercritical hexane in order to obtain diesel-like hydrocarbons from the renewable feedstock.

Experimental

Materials

Mesoporous silica gel (SiO2, Sigma-Aldrich, St. Louis, MO, USA), cerium dioxide (CeO2, Sigma-Aldrich, St. Louis, MO, USA), and HPS (MacroNet 270, MN-270, Purolight Inc., Llantrisant, Wales, UK) were crushed, and the fractions with the particle size less than 45 μm were used as catalyst supports. Iron (III) nitrate (Fe(NO3)3·6H2O, 99.0%, Sigma-Aldrich, St. Louis, MO, USA), iron (III) chloride (FeCl3·6H2O, 99.0%, Sigma-Aldrich, St. Louis, MO, USA), ruthenium (IV) hydroxochloride (RuOHCl3, 99.9%, Sigma-Aldrich, St. Louis, MO, USA)), and ruthenium (III) acetylacetonate (Ru(acac)3, 97.0%, Sigma-Aldrich, St. Louis, MO, USA) were used without purification as metal oxide precursors. Ethylene glycol (EG, 99.0%) and tetrahydrofuran (THF, 99.0%) were purchased from Macron Fine Chemicals (Macron Chemical Group, London, UK) and used as received. Ethanol (95%) was purchased from EMD (Tver, Russia) and used without purification. Stearic acid (99.9%, ChimMedService, Tver, Russia), n-hexane (C.G., ReaChim, Moscow, Russia), and nitrogen (99.9%, AGA, Tver, Russia) were used as received for deoxygenation experiments.

Catalyst preparation

Silica-based catalyst preparation

Fe3O4–SiO2 sample was prepared according to the following procedure. A mixture consisting of 2 g of Fe(NO3)3 dissolved in 10 mL of ethanol and 2.5 g of silica gel was stirred overnight in air and then dried in a vacuum at room temperature for 2 h. The powder obtained was wetted with 25 drops of EG and then heated in a quartz tube in an argon atmosphere at a temperature of 250°C for 5 h.

0.528 g of Ru(acac)3 was dissolved in 10 mL of THF and mixed with the Fe3O4–SiO2 prepared in the previous step. The mixture was stirred overnight and the resulting sample was then dried in vacuum at room temperature and wetted with 25 drops of EG. The Ru-containing sample was then heated in a quartz tube under argon to 300°C and held for 3 h.

Ceria-based catalyst preparation

Fe3O4–CeO2 sample was prepared according to the following procedure. A mixture consisting of 2 g of Fe(NO3)3 dissolved in 10 mL of ethanol and 2.5 g of ceria was stirred overnight in air and then dried in a vacuum at room temperature for 2 h. The powder obtained was wetted with 25 drops of EG and then heated in a quartz tube in an argon atmosphere at a temperature of 250°C for 5 h.

0.528 g of Ru(acac)3 was dissolved in 10 mL of THF and mixed with the Fe3O4–CeO2 prepared in the previous step. The mixture was stirred overnight and the resulting sample was then dried in vacuum at room temperature and wetted with 25 drops of EG. The Ru-containing sample was then heated in a quartz tube under argon to 300°C and held for 3 h.

HPS-based catalyst preparation

Fe3O4-HPS sample was prepared according to the following procedure. A mixture consisting of 1.45 g of FeCl3 and 0.5 g of CH3COONa·3H2O (C.G., Sigma-Aldrich, St. Louis, MO, USA) dissolved in 10 mL of ethanol and 2.5 g of HPS washed with acetone and dried was stirred overnight in air and then dried at a temperature of 60°C for 2 h. The powder obtained was wetted with 25 drops of EG and then heated in a quartz tube in an argon atmosphere at a temperature of 200°C for 5 h.

0.3856 g of RuOHCl3 was dissolved in 6 mL of a complex solvent consisting of water, methanol, and THF (1:1:4) and mixed for 15 min with the Fe3O4-HPS prepared in the previous step. The resulting sample was then dried at 70°C and dispersed in 30 mL of distilled water heated up to 70°C at pH of 10.0 adding 0.2 M solution of NaOH dropwise. The resulting sample was washed by the distilled water for neutralization and dried at 70°C overnight in the air.

The reduction of all samples was carried out before catalytic experiments by hydrogen at 300°C for 2 h in a quartz tube.

Catalyst characterization

Magnetic measurements were performed by Quantum Design MPMS XL magnetometer (Quantum Design, San Diego, CA, USA) using the systems DC measurement capabilities. The TEM images were obtained using a JEOL JEM1010 transmission electron microscope (JEOL, Tokyo, Japan). Images were analyzed with image-processing package ImageJ to estimate nanoparticle diameters. X-ray photoelectron spectroscopy (XPS) was carried out using photoelectron spectrometer ES-2403 (Russian Academy of Science, St. Petersburg, Russia) equipped with PHOIBOS-100-MCD (Specs GmbH, Zurich, Switzerland) energy analyzer and XR-50 X-ray source with a twin-anode Mg/Al. Low-temperature nitrogen physisorption measurements were carried out Beckman Coulter™ SA 3100™ (Beckman Coulter Inc., Breya, CA, USA) analyzer. X-ray fluorescence (XRF) measurements were performed by Zeiss Jena VRA-30 spectrometer (ZEISS, Jena, Germany).

Deoxygenation procedure

The stearic acid was chosen as a model compound for the deoxygenation experiments. The catalyst testing was carried out in Parr Series 5000 Multiple Reactor System (Parr Instrument Company, Moline, IL, USA) in the medium of supercritical n-hexane (Tc=234.5°C, Pc=3.02 MPa). The typical reaction conditions were the following: stearic acid concentration in n-hexane – 0.2 mol/L, pH – 6.9, catalyst mass – 0.05 g, temperature – 250°C, nitrogen pressure – 3.0 MPa, total pressure – 6.8 MPa, stirring rate – 1300rpm [20], [21]. The liquid phase analysis was performed by GCMS using gaseous chromatograph GC-2010 and mass-spectrometer GCMS-QP2010S (Shimadzu Group, Kyoto, Japan) according to the procedure described elsewhere [20], [21], [58].

Results and discussion

Catalyst characterization results

The curves of magnetization at 300 K for the synthesized samples before the incorporation of Ru-containing particles are shown in Fig. 1. The presence of hysteresis indicates the superparamagnetic properties for all samples with nearly zero coercivity and remanence that is typically for magnetite which formation was confirmed by XPS analysis (Table 1, Figure 1S) [59], [60]. The highest saturation magnetization (4.5±0.1 emu/g) was observed for the HPS supported sample allowing its fast magnetic separation from the reaction mixture. The relatively low values of saturation magnetization for Fe3O4–SiO2 and Fe3O4–CeO2 (0.8±0.05 and 0.3±0.02 emu/g, respectively) can be explained by the small size of MNPs formed on the surface of the oxide support [61], [62].

Fig. 1: Magnetization curves for magnetically separable samples.
Fig. 1:

Magnetization curves for magnetically separable samples.

Table 1:

Magnetically separable catalyst characteristics.

Sample SBET, m2/g Vp, mL/g Concentrationa, wt. %
 Surface concentrationb, wt. %
 Ru stateb Fe stateb
Ru Fe Ru Fe
HPS 1075 0.42 – – – – – –
Fe3O4-HPS 450 0.18 – 19.8 – 11.3 – Fe3O4
Ru–Fe3O4-HPS 364 0.14 2.7 19.6 18.9 11.1 RuO2 Fe3O4
SiO2 376 0.14 – – – – – –
Fe3O4–SiO2 312 0.12 – 20.0 – 15.2 – Fe3O4
Ru–Fe3O4–SiO2 277 0.10 2.0 19.7 11.0 14.7 RuO2 Fe3O4
CeO2 105 0.14 – – – – – –
Fe3O4–CeO2 85 0.10 – 19.4 – 14.6 – Fe3O4
Ru–Fe3O4–CeO2 64 0.08 1.9 19.2 10.7 13.9 RuO2 Fe3O4

  1. aAccording to XFA; baccording to XPS.

Figure 2 presents TEM images of the synthesized magnetite containing samples before Ru incorporation. The fine distribution of the MNPs on the surface of the supports is well seen. The mean size of the Fe3O4 nanoparticles was estimated to be approximately 34.3±2.5, 26.6±1.4, and 26.5±1.1 nm for Fe3O4–HPS, Fe3O4–SiO2, and Fe3O4–CeO2, respectively. The smaller size of the MNPs for silica and ceria supported samples compared to HPS supported one confirms the lower values of their saturation magnetization. The formation of large magnetite particles for the HPS supported sample can be explained by the influence of the iron precursor used. TEM images of Ru-containing samples are presented in Fig. 3. The mean diameter of ruthenium oxide (according to XPS, Figure 2S) particles was calculated to be 3.6±0.1 for Ru–Fe3O4-HPS, 2.7±0.1 for Ru–Fe3O4–SiO2, and 2.6±0.1 nm for Ru–Fe3O4–CeO2 (Fig. 3).

Fig. 2: TEM images (a – Fe3O4-HPS, b – Fe3O4–SiO2, c – Fe3O4–CeO2) and particle size distribution (d) for Fe3O4-containing samples.
Fig. 2:

TEM images (a – Fe3O4-HPS, b – Fe3O4–SiO2, c – Fe3O4–CeO2) and particle size distribution (d) for Fe3O4-containing samples.

Fig. 3: TEM images (a – Ru–Fe3O4-HPS, b – Ru–Fe3O4–SiO2, c – Ru–Fe3O4–CeO2) and particle size distribution (d) for magnetically separable catalysts.
Fig. 3:

TEM images (a – Ru–Fe3O4-HPS, b – Ru–Fe3O4–SiO2, c – Ru–Fe3O4–CeO2) and particle size distribution (d) for magnetically separable catalysts.

The study of the catalyst porosity showed the expected decrease in the specific surface area and the pore volume during the incorporation of MNPs and Ru-containing particles (Table 1) for all synthesized samples. In spite of the decrease in the surface area, the samples were found to maintain their micro-mesoporous structure (see Figures 3S-8S), however, the proportion of pores with the size below 6 nm slightly decreased. This can be assumed with the formation of magnetite and ruthenium oxide particles on the surface of the support and in the mouths of the pores, which leads to their blockage and, consequently, a decrease in the specific surface area. The formation of MNPs and RuO2 on the surface of the support is also confirmed by the high surface concentration of Fe and Ru (Table 1).

Catalyst activity in supercritical deoxygenation

The testing of the synthesized magnetically separable catalysts in the stearic acid deoxygenation in supercritical n-hexane medium showed that the catalysts allow over 95% conversion to be achieved for 70 min (Fig. 4). All samples provide a fast initial rate of the conversion during the first 20 min. Then the reaction rate significantly decreases that can be connected with the catalyst active site saturation and blockage of the pores with the adsorbed substrate and products. Ru–Fe3O4-HPS catalyst is able to provide the highest stearic acid conversion (up to 99%) because of its higher surface area and the higher concentration of Ru and Fe (Table 1).

Fig. 4: Stearic acid conversion degree in the presence of magnetically recoverable catalysts.
Fig. 4:

Stearic acid conversion degree in the presence of magnetically recoverable catalysts.

The analysis of the reaction mixture showed the presence of palmitic acid, n-octadecane, n- and i-penadecane and n- and i-heptadecane among the reaction products (Fig. 5). It is interesting that the formation of palmitic acid is observed during the first 20 min of the process may be due to the cracking of the stearic acid in the supercritical conditions, and then its consumption proceeds with the formation of pentadecane (Figure 9S).

Fig. 5: Product composition at 70 min of the deoxygenation.
Fig. 5:

Product composition at 70 min of the deoxygenation.

Noteworthy that the oxide supported catalysts showed a higher formation of palmitic acid due to the high acidity of the support. Such acceleration of the cracking reactions can be connected with the presence of iron oxide on the catalyst surface. For comparison, the Ru-containing catalyst based on HPS does not show the formation of palmitic acid during the deoxygenation at the same reaction conditions (Figure 10S). However, the catalyst without magnetic properties allows only 88% of the conversion to be reached for 70 min. Besides, no C15–C17 isomers are observed while using the Ru-HPS catalyst, indicating that the introduction of Fe3O4 provides the product isomerization (as it is seen in Figure 11S).

Thus, based on the product composition of the stearic acid deoxygenation in the medium of supercritical n-hexane in the presence of magnetically separable catalysts, the following scheme of the process can be proposed (Fig. 6).

Fig. 6: Scheme of the supercritical stearic acid deoxygenation in the presence of magnetically separable catalysts.
Fig. 6:

Scheme of the supercritical stearic acid deoxygenation in the presence of magnetically separable catalysts.

The summarized C17+ selectivity of the supercritical stearic acid deoxygenation (Fig. 7) was found to be the highest for the Ru–Fe3O4-HPS catalyst (over 86%). Silica and ceria supported systems provide about 50% of the selectivity towards the formation of C17+ hydrocarbons. Thus, the HPS based catalyst was chosen as the most optimal catalyst. The performance of the Ru–Fe3O4-HPS in the multiple reuses was tested (Table 2). It is seen that the catalyst does not show a decrease in both activity and selectivity during at least 10 consecutive cycles. Moreover, the summarized loose in the catalyst amount was estimated to be less than 0.05 wt. % indicating the full catalyst removal from the reaction mixture.

Fig. 7: C17+ selectivity in the supercritical stearic acid deoxygenation in the presence of magnetically separable catalysts.
Fig. 7:

C17+ selectivity in the supercritical stearic acid deoxygenation in the presence of magnetically separable catalysts.

Table 2:

Ru–Fe3O4-HPS productivity in multiple reuses.

Cycle Stearic acid conversion, % C17+ selectivity, % Catalyst weight lose, wt. %
1 98.8 86.7 0.003
2 98.8 86.7 0.002
3 98.8 86.7 0.002
4 98.8 86.7 0.002
5 98.8 86.7 0.003
… … … …
10 98.7 86.5 0.01

Conclusions

Three Ru-containing magnetically separable catalysts were tested in the stearic acid deoxygenation in the medium of supercritical n-hexane. All catalysts provide over 95% conversion of the substrate for 70 min. Analysis of the reaction mixture showed that the presence of Fe3O4 nanoparticles accelerates the cracking reactions forming palmitic acid during the first 20 min of the experiment. Moreover, the oxide supports allow the formation of higher amounts of palmitic acid and C15 hydrocarbons. The highest C17+ selectivity (over 86%) was observed for Ru–Fe3O4-HPS catalyst while the silica and ceria supported systems provide about 50% of C17+ hydrocarbons selectivity. The HPS supported catalytic system was found to maintain its catalytic activity and selectivity for a minimum of 10 consecutive cycles with the loose in the catalyst amount was estimated to be less than 0.05 wt. %.

Article note

A collection of papers from the 18th IUPAC International Symposium Macromolecular-Metal Complexes (MMC-18), held at the Lomonosov Moscow State University, 10–13 June 2019.

Funding source: Russian Science Foundation

Award Identifier / Grant number: 19-79-10061

Funding source: Russian Foundation for Basic Researches

Award Identifier / Grant number: 19-08-00318

Award Identifier / Grant number: 18-08-00609

Award Identifier / Grant number: 18-29-06004

Funding statement: The financial support for deoxygenation experiments was provided by the Russian Science Foundation (Funder Id: http://dx.doi.org/10.13039/501100006769, grant 19-79-10061). The financial support for catalyst analysis was provided by the Russian Foundation for Basic Researches (Funder Id: http://dx.doi.org/10.13039/501100002261, grants 19-08-00318, 18-08-00609, 18-29-06004). The authors are grateful to Dr. Liudmila Bronstein (Indiana University, USA) for the help in TEM study, and Dr. Alexey Bykov (Tver State Technical University, Russia) for the help in XPS study.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/pac-2019-1012).

Published Online: 2019-12-27
Published in Print: 2020-06-25

© 2020 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: http://creativecommons.org/licenses/by-nc-nd/4.0/

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Preface
  4. The 18th IUPAC International Symposium Macromolecular-Metal Complexes (10–13 June, 2019, Moscow – Tver – Myshkin – Uglich – Moscow)
  5. Conference papers
  6. Magnetically separable Ru-containing catalysts in supercritical deoxygenation of fatty acids
  7. Palladium nanoparticles supported on nitrogen doped porous carbon material derived from cyclodextrin, glucose and melamine based polymer: promising catalysts for hydrogenation reactions
  8. Macromolecular complexes of polyampholytes
  9. Coordination polymers based on trans, trans-muconic acid: synthesis, structure, adsorption and thermal properties
  10. Allylic hydrocarbon polymers complexed with Fe(II)(salen) as a ultrahigh oxygen-scavenging and active packaging film
  11. Removal of chromium ions by functional polymers in conjunction with ultrafiltration membranes
  12. Engineering the ABIO-BIO interface of neurostimulation electrodes using polypyrrole and bioactive hydrogels
  13. Formation of ruthenium nanoparticles inside aluminosilicate nanotubes and their catalytic activity in aromatics hydrogenation: the impact of complexing agents and reduction procedure
  14. Multifunctional carriers for controlled drug delivery
  15. Evaluation of sulfide catalysts performance in hydrotreating of oil fractions using comprehensive gas chromatography time-of-flight mass spectrometry
  16. Ni–Mo sulfide nanosized catalysts from water-soluble precursors for hydrogenation of aromatics under water gas shift conditions
  17. Combination of nanoparticles and carbon nanotubes for organic hybrid thermoelectrics
  18. Ultrafine metal-polymer catalysts based on polyconjugated systems for Fisher–Tropsch synthesis
https://doi.org/10.1515/pac-2019-1012
Schlagwörter für diesen Artikel
ceria; deoxygenation; hypercrosslinked polystyrene; magnetite; MMC-18; MNPs; silica; supercritical hexane

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Preface
  4. The 18th IUPAC International Symposium Macromolecular-Metal Complexes (10–13 June, 2019, Moscow – Tver – Myshkin – Uglich – Moscow)
  5. Conference papers
  6. Magnetically separable Ru-containing catalysts in supercritical deoxygenation of fatty acids
  7. Palladium nanoparticles supported on nitrogen doped porous carbon material derived from cyclodextrin, glucose and melamine based polymer: promising catalysts for hydrogenation reactions
  8. Macromolecular complexes of polyampholytes
  9. Coordination polymers based on trans, trans-muconic acid: synthesis, structure, adsorption and thermal properties
  10. Allylic hydrocarbon polymers complexed with Fe(II)(salen) as a ultrahigh oxygen-scavenging and active packaging film
  11. Removal of chromium ions by functional polymers in conjunction with ultrafiltration membranes
  12. Engineering the ABIO-BIO interface of neurostimulation electrodes using polypyrrole and bioactive hydrogels
  13. Formation of ruthenium nanoparticles inside aluminosilicate nanotubes and their catalytic activity in aromatics hydrogenation: the impact of complexing agents and reduction procedure
  14. Multifunctional carriers for controlled drug delivery
  15. Evaluation of sulfide catalysts performance in hydrotreating of oil fractions using comprehensive gas chromatography time-of-flight mass spectrometry
  16. Ni–Mo sulfide nanosized catalysts from water-soluble precursors for hydrogenation of aromatics under water gas shift conditions
  17. Combination of nanoparticles and carbon nanotubes for organic hybrid thermoelectrics
  18. Ultrafine metal-polymer catalysts based on polyconjugated systems for Fisher–Tropsch synthesis
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