Vanadium incorporation in montmorillonite clays for oxidative diesel

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Kinetics, Catalysis, and Reaction Engineering

Vanadium incorporation in montmorillonite clays for oxidative diesel desulfurization Mariele I. S. De Mello, Eledir V Sobrinho, Victor Teixeira da Silva, and Sibele B. C. Pergher Ind. Eng. Chem. Res., Just Accepted Manuscript • DOI: 10.1021/acs.iecr.8b03232 • Publication Date (Web): 24 Oct 2018 Downloaded from http://pubs.acs.org on October 27, 2018

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Vanadium incorporation in montmorillonite clays for oxidative diesel desulfurization Mariele I. S. de Mello†, Eledir V. Sobrinho†, Victor Teixeira da Silva§, Sibele B. C. Pergher†* †Pós-Graduação

em Química – PPGQ, Universidade Federal do Rio Grande do Norte, Laboratório de Peneiras Moleculares, LABPEMOL. Instituto de Química. Natal, RN 59078-970, Brazil. §Programa de Engenharia Química, NUCAT, Universidade Federal do Rio de Janeiro, P.O. Box 68502, Rio de Janeiro, RJ 21941-914, Brazil (in memoriam) Corresponding authors: e-mail: [email protected], [email protected] Key words Clay, montmorillonite, pillared clays, K10, KSF, vanadium, oxidative desulfurization HIGHLIGHTS -

The incorporation of vanadium did not compromise the structure of the materials.

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The K-10 1% V catalyst showed the best result, reaching 58% oxidized dibenzothiophene.

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Support acidity, V distribution and specific area appear to influence oxidation activity.

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Materials with higher accessibility (K-10) and higher V contents (KSF) were more active.

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Diesel desulfurization was achieved by ODS in the presence of V clay-based catalysts.

Abstract: Burning fossil fuels containing significant amounts of sulfur compounds generates toxic and pollutant products, and removal of these sulfur compounds is of substantial interest to the oil industry. To achieve this, new technologies, such as oxidative desulfurization, are being developed with the aim of increasing the removal of these contaminants at lower costs. In this work, commercial clays (K-10 and KSF), a natural clay (Poço A) and a its pillarized (Poço A PILC) were impregnated with 1% vanadium for the oxidation and


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extraction of dibenzothiophene (DBT) in commercial diesel charge. The catalysts were characterized by XRD, textural analysis and SEM. The products obtained in the catalytic tests performed were analyzed by GC-FID gas chromatography.

The vanadium-

impregnated K-10 and KSF clays showed the best results regarding DBT oxidation, with yields of 33 and 58%, respectively. However, all clays yielded good results for extraction of the organic compound while avoiding oxidation. . 1. Introduction Fossil fuels, such as diesel fuel and gasoline, are contaminated by sulfur compounds along with other N-heterocyclics and metal compounds. The direct combustion of these fuels results in environmental pollution, emission of SOx (cause of acid rain) and the greenhouse effect due to CO2 emissions

1–4.

In addition to environmental pollution, these

emissions present a risk to human health, as they are highly toxic, corrosive, induce catalyst poisoning, reduce product value and increase operating costs 5. The desulfurization of fuels has received increasing attention in the global research community due to the increasingly stringent regulations and fuel specifications in many countries aimed at better environmental protection

6–8.

Refinement of crude oil to final products requires

desulfurization of the oil 9 because the reduction of sulfur and aromatic content also reduces particulate emissions by diesel engines 10,11. Hydrodesulfurization (HDS) has traditionally been used in refineries to reduce the content of organosulfur compounds in fuels by using high pressures and high temperatures in the presence of hydrogen 12–14. This process is highly efficient for the removal of thiols, sulfides, and some thiophene derivatives but is less effective for benzothiophene and dibenzothiophene and their derivatives, which have sterically hindered groups

11,15–18.

This

has stimulated the development of alternative or complementary technologies for deep desulfurization by HDS 19–21. Oxidation desulfurization (ODS) is a promising method that displays several special advantages, such as mild reaction conditions (ambient pressure and relative low temperatures), high selectivity, and favorable performance for the desulfurization of sterically hindered sulfur compounds

22–24.

As its name implies, oxidative desulfurization



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involves the chemical reaction between an oxidant and sulfur, which facilitates desulfurization. As a rule, ODS converts organic sulfur compounds to sulfoxides and/or sulfones by oxidizing agents and catalysts and then removes them by distillation, extraction or adsorption 22,25–30. The oxidation process itself leads to the removal of a substantial portion of the existing sulfur and enables efficient removal of the remaining sulfur compounds even with solvents such as methanol, which are not as effective for the selective extraction of nonoxidized sulfur compounds. Thus, this combined process is capable of significantly removing sulfur compounds in oil fractions at acceptable yields 31,32. The oxidation process does not have harmful effects on the distillation profile and other characteristics of the distillate. Sulfur-containing compounds are oxidized using appropriate oxidants and extracted by polar compounds 17,33,34. The heterogeneous catalysts used in ODS show a wide range of metals or metal oxides and supports, such as the metals zinc, cobalt, iron, vanadium, molybdenum, phosphorus, and tungsten

35–40.

As supports, alumina

41,42,

molecular sieves

2,11,14,43–47

and

the oxides themselves 16 are used. Recently, our group reported an oxidative desulfurization study using vanadium incorporated in different zeolitic structures, observing an activity of approximately 80% and that porous structures and accessibility play important roles in the activity 48. The use of lamellar materials, such as clays, would be an interesting approach to avoid the accessibility limitation problem due to the zeolitic pore size. In the literature, there are few reports on the use of clays

49–53

as supports in catalysts for this process, and

most studies have used clays in the desulfurization process by adsorption. Therefore, the aim of this study was to evaluate the clays as supports for vanadiumbased catalysts for the oxidative desulfurization process of a commercial diesel fuel. Two commercially treated montmorillonite clays with acids, one natural montmorillonite clay and one pillar montmorillonite clay were used for this purpose. 2. Experimental 2.1 Materials


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All reagents were used without pretreatment. Commercial diesel S1800 (BR Distributor) with a maximum sulfur content of 1800 ppm doped with 1000 ppm of dibenzothiophene was used. Dibenzothiophene (Aldrich, 98%), representing the sulfur species in diesel, was selected to evaluate the reactivity in ODS. Acetonitrile (Vetec, 99.8%) was used as the solvent extractor, and hydrogen peroxide (aqueous solution 30 wt%) was used as the oxidizing agent. Aldrich commercial clays (K-10 and KSF) and natural clay from the Neuquén region of Argentina supplied by the Colorminas company (called Poço A) were used, and this natural clay was pillarized (Poço A PILC)

54.

The pillarization process aims at

increasing basal spacing and creating micropores by inserting large cations such as polyhydroxy cations of Al. First the solution of the pillaring agent is prepared and then mixed in the clay previously swollen in water. Subsequently the material is calcined to stabilize the pillars. The vanadium source used as the active phase was ammonium metavanadate (Nuclear, 99%). 2.2 Synthesis and characterization of catalysts Impregnation of the active phase (1 wt.% V) was performed at 80 °C for 2 hours under reflux employing a solid/liquid ratio of 2 g / 20 mL. Then, the solvent was evaporated in a rotary evaporator maintained at 90 °C, and the samples were then oven dried at 80 °C. After the drying step, the samples were calcined at 500 °C for 3 h. To evaluate the amount of metal impregnated in the supports in the reaction, two catalysts with 5 and 9 wt. % V supported on KSF clay were used. The catalysts were characterized by X-ray diffraction (XRD) performed on Shimadzu equipment (model XRD-7000) using copper radiation (CuKα, λ = 1.5418 Å) and operated at 30 kV and 30 mA. Data were collected in the 2θ range from 3 to 65°. Information on the specific area of the material and distribution of pore sizes was obtained by the textural analysis of nitrogen adsorption using the BET method. Prior to the analysis, approximately 100 mg of the samples were vacuum-treated at of 300 °C for 3 h. The measurements were carried out at the temperature of liquid N2 (77 K). The morphology of several samples was studied by scanning electron microscopy using a scanning electron microscope (model ESEM-XL30 PHILIPS, voltage of 30.00 kV and amperage of 30.00



mA). Prior to the analysis, the samples were coated with a gold layer to avoid the appearance of charges on the surface that could lead to distortions in the image. 2.3 Catalytic experiments The catalytic oxidation of DBT using hydrogen peroxide (Vetec, 30% wt.%) as the oxidizing agent and acetonitrile (Vetec, 99.8%) as the solvent was performed in an Erlenmeyer flask using an orbital shaker. In a typical experiment, 100 mg of the catalyst was suspended while stirring at 200 rpm in 10 mL of a mixture containing 1000 mg/L dibenzothiophene (Aldrich, 98%) added to commercial diesel (S1800) and acetonitrile (diesel/solvent ratio of 2:1). To initiate the reactions, half the amount of oxidizing agent was added and when half of the reaction time was completed, the remainder of hydrogen peroxide (total amount used 0.5 mL and H2O2/BDT = 90) at a constant temperature of 55 °C for 2 hours. The product of the reaction was filtered to remove the catalyst, and to remove the water generated during the reaction by the decomposition of hydrogen peroxide, anhydrous sodium sulfite was added (Kinetic, PA). The phases (oil / solvent) were separated, and the reaction products (solvent phase) were quantitatively analyzed by GC-FID (Varian CP-3800) after filtration and possibly a settling step using a CPSil 5CB capillary column (30 m x 0.53 mm x 5 μm). 3. Results and discussion 3.1 Catalyst Characterization X-ray diffraction was used to identify the phases in the supports and catalysts, and the results are shown in Figure 1. The materials showed a characteristic diffractogram of the smectite family (montmorillonites, 2 theta ≈ 6°), and the interlamellar spacing of clays was detected according to the Bragg equation (λ = 2d sinθ) as indicated in Figure 1. Note that all supports contained quartz as an impurity (2 theta ~ 27°); however, no peaks in the V2O5 phase were observed (2 theta = 15.4, 20.2, 26.1, 31.2 among others), indicating that it was very dispersed or presented as small crystallites not observable by XRD (smaller than 3-4 nm, usually the limit of detection of this technique) or as an amorphous or poorly crystalline phase.


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Analysis of diffractograms of the acid-treated commercial clays (K-10 and KSF) supports and catalysts showed that both presented (001) reflections, but upon being impregnated and calcined, these reflections were shifted or disappeared. With impregnation and calcination, the K-10 clay showed disappearance of the characteristic (001) reflection of this lamellar material. This sample already presented a structural disorder due to the very severe acid treatment, as indicated by the manufacturer; the procedure (impregnation and calcination) carried out in this support caused more disorder in the structure, leading to the disappearance of the (001) reflection. Prior to the calcination process, this sample had a basal spacing of d (001) = 15.75 Å. For the KSF clay, a (001) reflection shift to the right (according to the order of the Bragg angle) was observed after calcination, as expected for this type of material. This is because the water loss of the material occurs upon heating during calcination, promoting the reduction of the basal spacing of 13.49 Å to 9.99 Å after calcination. The clays, both the natural clay (Poço A) and the natural pillar clay (Poço A PILC), were calcined prior to being subjected to the impregnation process. For the Poço A clay, the (001) reflection was shifted in the support due to calcination. This shift was maintained after impregnation and calcination. The (001) reflection represented a basal spacing of 9.60 Å in the support, and the same basal spacing was observed for the catalysts, indicating that the procedure performed on the support did not alter the structure of the material. For the Poço A pillar clay (Poço A PILC), a shift of the (001) reflection to the left was observed relative to the natural Poço A clay. This displacement was generated by the pillarization process, providing evidence that the pillarization was successful because there was an increase in the interlamellar spacing. The (001) reflection, which previously represented the basal spacing of 9.60 Å, shifted to 17.89 Å after pillarization. With the impregnation process, this displacement was maintained, i.e., the impregnation did not alter the structure of the material.



Figure 1: X-ray diffractograms of the clays before and after impregnation with vanadium: K-10, KSF, Poço A and Poço A PILC. N2 adsorption analysis of the clays are presented in Table 1. Note that for the Poço A clay, an area of 49 m2/g was suitable for natural clays (10-70 m2/g), and when this same clay was pillarized, an increase in the specific area, given by the increase in accessibility by the insertion of the pillars, was observed. For K-10 clay disordering during the acid treatment, the lamellae become more accessible, and consequently, an area increase (224 m2/g) occurred; however, the milder acid treatment for the KSF clay did not significantly alter its specific area. When we observed the BET area values after the vanadium impregnation, a reduction in the magnitude of the corresponding original support occurred for all the catalysts, representing a reduction of approximately 6% for the K-10 1% V catalyst and a more significant reduction for the KSF 1% V catalyst of approximately 58%. This suggests a deposition of the oxide on the surface or between the blades of the material instead of cation exchanges. In the Poço PILC clay, the pores may have been blocked, limiting the access of nitrogen because the basal spacing remained the same, but the specific area decreased. A small loss of structural disorganization with the vanadium incorporation procedure was not ruled out.


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Table 1: Specific area and pore volume of pure and vanadium-impregnated clays calculated from adsorption data Material

ABET AMicro

AExt

VTotal

VBJH

VMicro

KSF

12

12

0

0.019

0.018

n.d.

KSF 1%V

5

5

0

0.007

0.022

0.003

K10

224

n.d.

224

0.230

0.270

n.d.

K10 1%V

210

n.d.

210

0.286

0.269

n.d.

Poço A

49

24

25

0.061

0.059

0.012

Poço A 1%V

24

13

11

0.034

0.037

0.006

Poço A PILC

216

180

36

0.132

0.037

0.092

Poço A PILC 1%V

129

104

25

0.086

0.032

0.054

*ABET: specific area obtained by the BET method (total area); Amicro: specific area related to the contribution of micropores obtained by the t-plot method; Aext: specific external area obtained by the difference between ABET and Amicro; Vtotal: total volume of pores obtained for p/po = 0.99; Vmicro: pore volume referring to the contribution of micropores obtained by the t-plot method; VBJH: pore volume referring to the contribution of mesopores obtained by the BJH method; n.d.: not determined.

To better understand, an outline of the organization of the clay structure and the location of the vanadium oxides is presented in Figure 1. The K-10 clay showed greater structural disorder compared to the KSF clay and mainly in relation to the other clays, both natural and pillarized, due to the more severe acid treatment used in its production. It is also possible to visualize the increase around the Poço A clay via the pillarization, producing Poço A PILC. In addition, according to the results obtained by X-ray diffraction and N2 adsorption/desorption analysis, we predicted the location of the oxides in the structures. In the pillarized clay, the oxides were specifically located in the pores of the structure, generating blocking; therefore, we observed a significant reduction in the specific area for this sample. For the natural clay, the oxides are preferably located outside the pores, more specifically on the outer surface of the structure. The micrographs obtained by scanning electron microscopy (SEM) analysis did not show significant differences in the morphologies of the samples. All the samples showed the morphological pattern of smectite clays. These clays occur frequently in fine-grained



aggregates that may be lamellar 55, like the structures observed in the analyzed samples. No aggregates were observed, indicating that V is found in the interlamellar region. 3.2 Catalytic Tests Results The reaction system contains two liquid phases, one consisting of the commercial diesel doped with DBT (1000 ppm) and the other consisting of the solvent extractor (acetonitrile) and a solid phase of the catalyst. Therefore, the results obtained in the oxidation experiment by GC analysis of the solvent phase are shown in Figure 2. Two products were observed as a result, extraction and the sulfone of DBTs. The extraction product was performed under the same conditions of the oxidation process. Total removal of the sulfur added to the diesel in the form of DBT was observed. The efficiency of desulfurization was determined by both the solvent extraction process (Figure 2a), because organosulfur compounds have a polar characteristic due to the electronegativity of the sulfur atom, as well as by oxidation (Figure 2b) and subsequent extraction. In this case, oxidation alters the polarity of these compounds to sulfone, thus facilitating their extraction into the aqueous medium. Sulfonate (DBTO) conversions ranged from 12 to 58%. The catalysts supported with KSF and K-10 impregnated with vanadium showed the highest conversions (33 and 58%, respectively) compared to the other clays. However, all clays (supports or impregnated) yielded good results in extraction of the organic compound. As discussed above, the KSF and K-10 clays with vanadium showed the best oxidation results compared to the other samples. These materials differ in relation to their specific area and acidity. The KSF clay presents a smaller area than the K-10 clay. Both materials have Brönsted acidity by the acid treated, in the case of KSF this treatment is in milder conditions compared to K-10, so the superficial area of K-10 is higher than KSF. 56. Thus, we can relate the performance of these two catalysts to the area and the type of acidity. In K-10, because the acid treatment is more severe, a greater amount of aluminum is removed, compromising the structure of the material. In this case, the acidic sites present in the system were more diluted. The activity may also be related to the strength of the support acid sites, where materials with stronger acid sites show better performance in comparison with the other clays.


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Figure 2: The extraction (a) and oxidation (b) of the catalytic tests on the clays. During this study, a reaction was performed with a higher percentage of vanadium impregnating the KSF clay support. The X-ray diffraction results of the clays containing 5% and 9% vanadium as well as the carrier and the catalyst impregnated with 1% for comparison are shown in Figure 3. In this range of 2 theta (5-65 °), as shown in Figure 1 for the carrier and for the catalysts impregnated with 1% vanadium, only diffraction peaks corresponding to the phase of the clays were observed. However, when larger amounts (5



and 9%) were impregnated, additional reflections corresponding to the crystalline phase of V2O5 were observed, as proven by the comparison with the V2O5 standard - ICSD 15798 (vertical lines of the diffractogram).

Figure 3: X-ray diffraction of clays impregnated with 5% and 9% vanadium. The 5% KSF and 9% KSF catalysts were used to examine whether the amount of the metal affected the amount of oxidized product at the end of the process. The result is shown in Figure 4.


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Figure 4: Reactions of KSF clay with different vanadium contents. Upon impregnating KSF with 5% vanadium, the amount of oxidized dibenzothiophene doubled, indicating that the vanadium content also influences the oxidation process. This same result was verified in other studies in the literature, as Cedeño-Caero et al. 57 found that vanadium species act as the active phase in the oxidation of DBTS to DBTS sulfones. The authors also observed that the activity increased with increasing amounts of V but only up to the formation of a vanadium monolayer on the carrier. For the studied materials, this monolayer achieved the following contents: 12% V/Ti, 15% V/Al-Ti and 6% V/Nb. For vanadium values above these levels, the oxidation activities decreased slightly, which was attributed to the dimeric amount and polymer chains of the VO4 units, which gradually increased and formed polymeric vanadium oxide species. As an example, for Vx/Nb catalysts, although the highest overall sulfur removal was obtained with 20% V/Nb, the DBTS sulfone yield increased with V contents up to 6 wt.% and then decreased when the V content increased beyond this value. This agreed with the observations for the KSF clay with 9% vanadium. Likewise, the catalyst containing 9% vanadium having a low oxidation activity can be explained by the possible formation of clusters by the oxides (V2O5 reflections observed in the diffractogram), which would consequently block the pores, facilitated by the low specific area of this clay.



4. Conclusion The removal of sulfur compounds present in the diesel fuel was performed efficiently, yielding greater than 100%, depending on the reactivity of each catalyst. The incorporation of vanadium did not compromise the structure of the materials, and in some materials, a decrease in the specific area was observed, proving the incorporation of the metallic oxides within the structure. Analysis of the reaction results showed that among the catalysts, the K-10 catalyst impregnated with 1% vanadium exhibited the best result, reaching 58% oxidized dibenzothiophene. However, increasing the amount of impregnated vanadium showed that the highest oxidation was obtained with an intermediate value of vanadium, which was 5% in this study. The acidity of the supports as well as the vanadium distribution and specific area appear to influence the oxidation activity. Materials with higher accessibility (K10) and higher vanadium contents (KSF) were more active. In conclusion, desulfurization of diesel fuel can be achieved by the ODS process in the presence of vanadium-based catalysts and support clays. Acknowledgements Sibele Pergher and Mariele I S. de Mello thank CNPq for financial support. References (1)

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Vanadium incorporation in montmorillonite clays for oxidative diesel

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