Conversion of glucose into 5-hydroxymethylfurfural by carbonaceous solid acid catalysts loaded with Brønsted acid and Lewis acid in biphasic system

doi:10.21203/rs.3.rs-2699224/v1

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Conversion of glucose into 5-hydroxymethylfurfural by carbonaceous solid acid catalysts loaded with Brønsted acid and Lewis acid in biphasic system

https://doi.org/10.21203/rs.3.rs-2699224/v1

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published 14 Aug, 2023

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Biomass-derived 5-Hydroxymethylfurfural (HMF) is a vital platform compound for synthesizing biofuel and various high-value chemicals. This work prepared carbonaceous solid catalysts with Brønsted acid and Lewis acid using pine biomass as raw materials through metal chloride impregnation, carbonization, and sulfonation. Catalysts were then applied to convert glucose into HMF in a biphasic system involving NaCl solution and gamma-valerolactone. The results showed good catalytic reactivity for carbonaceous solid catalysts. The experiment of PC-Al-SO₃H catalyzed glucose obtained 85.62 mol% glucose conversion and 45.40 mol% HMF yield at 160°C and 6 h. HMF yield and glucose conversion were significantly improved compared to uncatalyzed control experiments. Further, by using PC-2Al-SO₃H as the catalyst, we were able to obtain an optimum HMF yield of 59.62 mol%. Furthermore, under the same conditions, PC-2Al-SO₃H showed good cycle stability, with a decrease in the yield of less than 5 mol% after 5 cycles.

5-hydroxymethylfurfural

carbonaceous solid acid catalysts

glucose

biphasic system

Sustainable biofuel and chemical production using renewable and carbon-neutral biomass resources could cope with fossil resource depletion and global climate change [1–3]. 5-hydroxymethylfurfural (HMF) derived from biomass is an essential intermediate platform compound, which can be converted into bio-liquid fuels and various high-value chemicals, such as 2,5-dimethylfuran (DFF), 2,5-furan dicarboxylic acid (FDCA), and levulinic acid (LA) [4–8]. Fructose and glucose can be degraded into HMF [9]. In mild conditions, fructose can easily convert HMF because it contains a five-ring structure similar to HMF [4]. However, due to its high cost [10], there are better raw materials than fructose for synthesizing HMF. Natural monosaccharides, such as glucose, can be used to prepare HMFs [5, 11].

The conversion of glucose to HMF can occur in two ways [12, 13]. The first method is the isomerization of glucose to fructose, followed by the dehydration of fructose to HMF, which were catalyzed by Lewis acid and Brønsted acid, respectively; The second is glucose directly produces HMF with the Brønsted acid. With Brønsted acid only, the conversion of glucose to HMF requires high activation energy [14], resulting in the difficult conversion at low temperature. For example, Garces et al. [15] used HCl to catalyze glucose degradation at 383 K for 4 h, obtaining a glucose conversion rate of only 38%. In contrast, the activation energy of glucose conversion to HMF is lower as Brønsted acid and Lewis acid are synergistic[16]. Therefore, the catalytic system composed of Brønsted acid and Lewis acid can effectively catalyze the conversion of glucose to HMF under mild conditions.

Homogeneous catalytic systems consisting of homogeneous acid and soluble metal salts can produce a high HMF yield for glucose thoroughly mixed with the catalyst [11, 17, 18]. However, homogeneous catalysts pose severe environmental pollution risks, difficult separation and recovery after reaction, and severe equipment erosion [19, 20].

Heterogeneous solid catalysts such as ion exchange resins, molecular sieves, and metal oxides have been developed in recent years to overcome the shortcomings of homogeneous catalytic systems [21–27]. In an impregnation-calcination method, Shen et al. [25] used a sulfated natural attapulgite (ATP)-based catalyst (SO₄²⁻/In₂O₃-ATP) to catalyze glucose conversion, resulting in a 40.2% yield of HMF. In a study by Rezayan et al. [27], bifunctional phosphate Gallia (GaP) solid catalysts were prepared by solid-state grinding and applied to glucose-to-HMF transformation, resulting in a 65.72% yield of HMF. However, the cost of preparation of the above solid catalysts is high. The carbonaceous solid acid catalysts prepared from biomass are simple to prepare, low-cost, and thermally stable [28].

Furthermore, biochar comprises oxygen-containing functional groups, such as hydroxyl and carboxyl, which can act as carriers of catalytic sites [29, 30]. Mazzotta et al. [31] used TiO₂ and p-toluenesulfonic acid to modify glucose-based solid carbon and obtained carbon catalysts (GluTsOH-Ti) containing Brønsted acid and Lewis acid catalytic sites. When glucose was converted to HMF using the catalyst, 48 mol% of HMF was produced, and HMF yield increased by 38 mol% over the control experiment without the catalyst. Furthermore, metal chlorides also exhibited excellent Lewis acidity [17, 18]. However, there are few studies on loading metal chlorides as Lewis acids to biochar to prepare solid acid catalysts.

The solvent plays a crucial role in the preparation of HMF from glucose. Water is the most commonly used solvent since it is eco-friendly and cheap [32]. However, in the acidic aqueous phase, HMF is easily degraded into LA [33]. HMF yield is decreased by side reactions that form by-products between glucose, HMF, and intermediates [34–36].

According to Xiong et al. [37], most of the generated HMF was degraded by solid acids to catalyze glucose in an aqueous phase, and the yield of HMF was only 4.2 mol%. HMF can be produced in higher yields by forming biphasic solvents with organic solvents such as tetrahydrofuran (THF) and γ-valerolactone (GVL) [38–40]. To avoid HMF degradation and side reactions, organic solvents are used to extract and separate the generated HMF from the aqueous phase. Shen et al. [41] found that GVL was better than THF, n-butanol, toluene, n-hexanol, and methyl isobutyl ketone in sodium chloride solution for the extraction of HMF. Huang et al. [42] also found that for a GVL: H₂O volume ratio of 10:1, the yield of HMF catalyzed by carbon-based solid acid catalyst (SC-CCA) was 78.1%, while the yield of HMF was only 3.5% in pure water. These results indicate that water/GVL solvent can produce a high yield of HMF. Furthermore, two-phase solvents can cope with carbonaceous solid acid catalysts' poor mass transfer efficiency, leading to longer reaction time.

This paper aims to synthesize carbonaceous solid acid catalysts loaded with Brønsted/Lewis acid catalytic sites using pine biomass as a raw material via impregnation, carbonization, and sulfonation. Various properties were studied using XRD, FTIR, SEM, BET, and Py-IR to characterize the above-prepared catalysts. A biphasic solvent of NaCl-H₂O/GVL was also used to evaluate the catalytic activity of the catalysts for converting glucose to HMF. Furthermore, the cycle stability of the catalyst was investigated without regeneration.

Materials

D (+)-glucose, D (-)-fructose, NaCl, H₂SO₄ (98%), and H₃PO₄ (85%) were purchased from Sinopharm Chemical Reagent Co., Ltd. AlCl₃∙6H₂O, CrCl₃∙6H₂O, ZnCl₂, FeCl₃, and LA (99%) were purchased from Macklin Biochemical Co., Ltd. GVL (98%) and MgCl₂ were purchased from Aladdin Biochemical Technology Co., Ltd. HMF (99.9%) was purchased from Bide Pharmatech Co., Ltd. All purchased chemicals were analytical grade and used without further purification.

Catalysts preparation

In a typical process, 5 g AlCl₃∙6H₂O and 5 g pine powder were added into 50 mL 0.5 mol/L H₃PO₄ solutions. The mixture was impregnated at 60°C for 48 h and dried at 105°C for 12 h. Metal chlorides such as ZinCl₂, MgCl₂, and FeCl₃ were also used for impregnation. After grinding, the solid powder obtained was carbonized for 1 h under an N₂ atmosphere at 550°C. Afterward, the carbonized powder was mixed with 98% H₂SO₄ (carbon mass to H₂SO₄ volume ratio at 1:5), followed by continuous sulfonation at 150°C for 10 h. After the sulfonation reaction, the mixture was cooled to room temperature and diluted with deionized water. The sulfonated carbon was separated from the mixture and then washed with hot deionized water exceeding 80°C until the filtrate was neutral and free of sulfate ions. Sulfonated carbons that had been washed were dried at 105°C to yield carbonaceous solid catalysts with the name PC-M-SO₃H (M = Al, Zn, Mg, Fe). A similar procedure was also performed without the addition of metal to PC-SO₃H for comparison. Furthermore, PC was prepared without metal impregnating and sulfonation, and PC-Al was prepared with Al-impregnated carbon without sulfonation. To alter the Lewis acid strength of the catalyst, 10 g AlCl₃∙6H₂O and 5 g pine powder were mixed to obtain PC-2Al Then, the catalyst of PC-2Al-SO₃H was prepared by the same sulfonation method.

Catalysts characterization

An X-ray diffractometer (XRD, PANalytical X'Pert PRO) was used to study the structural characteristics of prepared carbonaceous solid catalysts (λ = 0.1541nm). Working voltage and current were 40 kV and 40 mA, respectively. The patterns were collected with 2θ range from 10–80° at a step of 0.02°. Infrared Fourier transforms spectroscopy (FT-IR, Nicolet iS20) was used to detect the functional groups of catalysts in the range of 400–4000 cm^− 1 wavenumber. Each sample was mixed with KBr and pressed into tablets. SEM (Zeiss Gemini 500) was used to characterize the surface morphology of catalysts. The element distribution on the surface of the catalysts was examined using energy-dispersive X-ray spectroscopy (EDS, Esprit 2.0). Specific surface area and pore structure were determined using nitrogen adsorption-desorption (BET, ASAP 2010). Additionally, the Brønsted acid and Lewis acid strength distribution on the catalyst was determined using pyridine infrared spectroscopy (Py-IR, Tensor 27).

Catalytic activity test

HMF was converted from glucose using a heating reactor with a temperature indicator and magnetic stirring (DF-101s). In a typical catalytic experiment, 0.2 g glucose, 0.1 g catalyst, 0.8 g NaCl, 5 mL deionized water, and 10 mL GVL were added into a test tube. Reactions were carried out at a temperature ranging from 145–170°C and at a time ranging from 3–9 h. The test tube was cooled rapidly with a fan to room temperature as soon as the reaction was complete. After that, a 0.22 µm pore size organic filter membrane was used to separate the solid catalyst. To prepare the sample for analysis, the organic and aqueous phases were separated and diluted ten-fold with water.

Product analysis

High-performance liquid chromatography (HPLC, Agilent 1200) was used to quantitatively analyze glucose, fructose, HMF, and LA. A differential refractive detector and an ultraviolet detector were used as detectors. A column of BioRad HPX-87H (7.8 mm × 300 mm) was adopted. The mobile phase was 5 mmol/L H₂SO₄ with a flow rate of 0.5 mL∙min^− 1. The temperature of the column and detectors was 60°C. Each sample with 25 µL was injected and completely eluted within 60 minutes. Furthermore, glucose and fructose peak areas were detected by differential refractive signals, while ultraviolet detection signals detected HMF and LA. The following formulae were used to calculate glucose conversion and product yield:

$$Glucose conversion \left(mol\%\right)=\frac{Moles of carbon atom of reacted glucose}{Moles of carbon atom ofstaring glucose}\times 100\%$$

$$Product yield \left(mol\%\right)=\frac{Moles of carbon atom of product generated}{Moles of carbon atom of staring glucose}\times 100\%$$

Catalyst characterization

The XRD patterns of PC-SO₃H and PC-Al-SO₃H are shown in Fig. 1. A (002) plane diffraction peak corresponds to 23° of non-oriented structural properties of carbon in the catalyst [19]. As the degree of non-orientation increases, the diffraction peak of the (002) plane is broadened [43]. Therefore, AlCl₃-impregnated catalysts have little non-orientation. The (101) plane weak diffraction peak of carbon material appears at 2θ of 43°, which is caused by the graphitization of the carbon material [44]. Graphitization of carbonaceous catalysts improves their thermal stability to a certain degree. Furthermore, the characteristic AlPO₄ peaks appeared at 20°, 26°, and 36° for the PC-Al-SO₃H, indicating that AlCl₃ was dissolved in H₃PO₄ solution resulted in AlPO₄ [37].

The FT-IR spectra of carbon materials and carbonaceous solid acid catalysts are shown in Fig. 2. It is evident from all samples that the O-H band at 3434 cm^− 1 [45] shows the presence of vast amounts of -OH groups on the surface of catalysts. A low-intensity peak observed at 2930 cm^− 1, 850 cm^− 1, and 760 cm^− 1 was attributed to stretching vibrations of the C-H bond [46]. C = O and C = C peaks were found at 1710 cm^− 1 and 1612 cm^− 1, respectively [47]. Similarly, a characteristic O = S = O peak was observed in both PC-SO₃H and PC-Al-SO₃H [19], indicating that SO₃H groups were successfully introduced by sulfonation with H₂SO₄.

SEM images of PC-SO₃H and PC-Al-SO₃H at different magnitudes are shown in Fig. 3. Both catalysts exhibited microspheres and irregular pore structures. Compared with PC-SO₃H, the PC-Al-SO₃H exhibits larger microspheres and pore sizes. In addition, Fig. 4 shows the EDS spectra of the catalysts. The S element was detected in PC-SO₃H, while S and Al were found in PC-Al-SO₃H. The results were consistent with the characterization results obtained from XRD and FTIR.

The N₂ adsorption-desorption characterization of PC-SO₃H and PC-Al-SO₃H is shown in Fig. 5 (a). It could be seen that the curves of PC-SO₃H were the type of Ⅰ isotherm [48], while those of PC-Al-SO₃H was the type of Ⅳ isotherm [49]. Figure 5 (b) shows the pore size distribution of the catalysts. A majority of the PC-SO₃H was less than 5 nm in size, indicating that the catalyst is rich in micropores. However, PC-Al-SO₃H has micropores, mesopores, and macropores, which is evident from its pore size distribution. Table 1 shows the catalysts' BET surface area, pore volume, and average pore size. The specific surface area, total pore volume, and average pore size of PC-SO₃H were 990.1 m²∙g^− 1, 0.5 cm³∙g^− 1, and 2.6 nm, respectively. The activation effect of H₃PO₄ effectively increases the specific surface area of carbon materials [50]. PC-Al-SO₃H had a lower specific surface area and pore volume than PC-SO₃H, with only 12.4 m²∙g^− 1 and 0.02 cm³∙g^− 1, respectively. As H₃PO₄ reacts with metal salts without activation, the metal compound will block the pore structure, which would decrease specific surface area and pore volume [51]. However, the average pore size of PC-Al-SO₃H was 7.3 nm, which also proved that the catalyst mainly had mesoporous which would improve the catalyst's permeability and conversion efficiency [52].

Table 1

Physical properties of synthesized carbonaceous solid acid catalysts
Samples	Surface properties
Samples	S_BET^a (m²∙g^− 1)	V_p^b (cm³∙g^− 1)	D_p^c (nm)
PC-SO₃H	990.1	0.5	2.6
PC-Al-SO₃H	12.4	0.02	7.3

a BET surface area.

b Total pore volume.

c BJH desorption diameter.

The Py-IR spectra of PC-SO₃H, PC-Al-SO₃H, and PC-2Al-SO₃H are shown in Fig. 6. Some peaks at 1540 cm^− 1 and 1643 cm^− 1 were the characteristic peaks of Brønsted acid, while at 1445 cm^− 1, 1575 cm^− 1 and 1606 cm^− 1 were the absorption peaks of Lewis acid [53–55]. In addition, Brønsted acid and Lewis acid have a co-absorption peak at 1490 cm^− 1 [31, 56]. PC-SO₃H only contains Brønsted acid, while PC-Al-SO₃H and PC-2Al-SO₃H simultaneously contain Brønsted acid and Lewis acid. According to the peak area integral, the Lewis acid and Brnsted acid of PC-Al-SO₃H are 42.11 mol∙g^− 1and 6.55 mol∙g^− 1, respectively. Contrary to this, PC-2Al-SO₃H has both a strong Lewis acid and a weak Brnsted acid, the amounts of each being 53.69 mol∙g^− 1 and 4.68 mol∙g^− 1, respectively.

Conversion of glucose into HMF

Figure 7 shows the effects of reaction temperature (145–175°C) on glucose conversion and HMF yield as PC-Al-SO₃H was the catalyst. The glucose conversion increased continuously from 37.09 mol% to 97.17 mol% as the reaction temperature increased from 145°C to 175°C. However, the yield of HMF was increased first and then decreased. The maximum HMF yield was 45.40 mol% and the LA yield was 31.31 mol% at 160°C. At 175°C, the HMF yield decreased to 25.57 mol%, and the LA yield increased to 45.79 mol%. High temperatures may accelerate the degradation of HMF and produce various by-products [16, 57]. These experiment results showed that PC-Al-SO₃H catalysts could produce high yields of HMF at 160°C.

Figure 8 shows the effects of reaction time (3–9 h) on glucose conversion and HMF yield as PC-Al-SO₃H was the catalyst. As a result of extending the reaction time from 3 h to 9 h, glucose conversion increased from 59.42 mol% to 94.95 mol%. These results indicate that glucose needs a long time to be converted completely. However, the excessive extension of time would cause a low HMF yield. As the reaction time was 6 h, the best HMF yield of 45.40 mol% was achieved. With the reaction time extended to 9 h, the yield of HMF decreased to 29.49 mol%, while the yield of LA approached 54.23 mol%. It proved that most HMF were degraded into LA as lengthened the reaction time. An extended reaction time was required for PC-Al-SO₃H-catalyzed glucose because glucose is relatively stable at 160°C and has solid catalyst transfer resistance [58]. As a result, HMF was degraded to LA and produced other by-products [14, 15], reducing its yield. The optimal conditions for converting glucose to HMF with PC-Al-SO₃H were 160°C for 6 h.

Figure 9 shows the catalytic activity of PC-Al-SO₃H during the experiment. HMF and LA were the primary products catalyzed by PC-Al-SO₃H at 160°C for 6 h. In addition, glucose conversion reached 85.62 mol%, and HMF yield was 45.40 mol%. Without a catalyst, glucose conversion, and HMF yields were only 22.22 mol% and 11.780 mol%, respectively. Mazzotta et al. [31] prepared a heterogeneous carbonaceous catalyst (GluTsOH-Ti) to catalyze the conversion of glucose in the DMSO/water biphasic solvent. According to their results, the yield of HMF was 48 mol%, similar to this study. Thus, the PC-Al-SO₃H has good catalytic activity. The experiments also revealed that glucose could be converted to HMF in one step by using PC-SO₃H as a catalyst. However, the glucose conversion and HMF yield were lower than PC-Al-SO₃H, 56.54 mol% and 32.82 mol%, respectively. Therefore, the carbonaceous solid acid catalysts containing both Brønsted acid and Lewis acid were preferred for translating glucose to HMF when the conditions were mild.

Figure 10 shows the catalytic performance of various catalysts prepared by mixing metal chlorides such as AlCl₃, ZnCl₂, MgCl_2, and FeCl₃ with pine biomass during impregnation. Most catalysts have a higher glucose conversion rate and HMF yield than those of PC-SO₃H, which suggests that Lewis acids are successfully introduced to the catalysts with these metal chlorides. Catalysts modified by metal chlorides differed in their catalytic performance. It can be known that the catalytic activity of these catalysts was PC-Al-SO₃H > PC-Mg-SO₃H > PC-Zn-SO₃H > PC-Fe-SO₃H. AlCl₃ was mixed with pine biomass to improve catalyst performance to prepare a catalyst with the best catalytic performance.

Figure 11 shows the catalytic performance of PC-2Al-SO₃H in converting glucose into HMF. According to the results, glucose conversion, HMF yield, and LA yield were 86.53 mol%, 59.62 mol%, and 25.28 mol%, respectively. The conversion of glucose was similar to the experimental result when catalyzed by PC-Al-SO₃H, whereas HMF yield increased and LA yield decreased. Additionally, the total yield of HMF and LA was estimated to be close to that of glucose conversion, which indicated that the main products of glucose conversion were HMF and LA. As a result, the catalyst with strong Lewis acid reduces the degradation of HMF into LA and prevents the formation of by-products, resulting in a high yield of HMF.

Multicycle performance of the carbonaceous solid acid catalyst

Low production costs rely on carbonaceous solid catalysts' recycling stability. Glucose was more efficiently converted to HMF by PC-2Al-SO₃H. In the recycling experiments, the catalyst was separated after the reaction by filtration, washed with massive deionized water, dried at 105 for 12 h, and reused. As shown in Fig. 12, PC-2Al-SO₃H demonstrated high recycling stability by reducing the yield of HMF from 59.62 mol% to 54.82 mol% after regeneration 5 times, and the reduction was less than 5 mol%. According to a study, glucose adsorption and HMF by-product detachment from catalyst surfaces can lead to catalyst deactivation, resulting in a decrease in glucose conversion and HMF yield [19, 59].

This work prepared a carbonaceous solid acid catalyst using pine powder via metal chloride impregnation, carbonization, and sulfonation with Brønsted acid and Lewis acid. The catalysts were applied to convert glucose into HMF in a biphasic system involving NaCl solution and γ-valerolactone. The main findings and conclusions were as follows.

(1) Characterization results of the PC-Al-SO₃H catalyst showed that AlPO₄ was formed during AlCl₃ impregnation, which introduced Lewis acid to the catalyst. SO₃H groups formed by sulfonation with H₂SO₄ played the role of Bronsted acid. Compared with the sulfonated catalyst PC-SO₃H without AlCl₃ impregnation, PC-Al-SO₃H exhibited larger microspheres and pore sizes, which would improve the catalyst's permeability and conversion efficiency of glucose.

(2) Effects of reaction temperature, reaction time, types of catalyst, and loading amounts of metal chloride during impregnation on the conversion of glucose to HMF were examined. Compared with the catalyst of PC-SO₃H loaded with only Bronsted acid, PC-Al-SO₃H increased glucose conversion and HMF yield. A catalyst PC-2Al-SO₃H achieved an 86.53 mol% glucose conversion and a 59.62 mol% HMF yield at 160°C and 6 h. The more essential Lewis acid through PC-2Al-SO₃H results in a higher HMF yield while a lower yield of LA results.

(3) Stability test of the PC-2Al-SO₃H catalyst revealed that the prepared catalyst generally presented good performance with only slightly decreased HMF yield during multicycle experiments. The yield of HMF slightly decreased from 59.62 mol% to 54.82 mol% after 5 cycles of glucose conversion without catalyst regeneration.

Ethical Approval

Not applicable.

Competing interests

The authors declare no conflict of interests.

Authors' contributions

HG contributed to Investigation, Data curation, Formal analysis, and Writing—original draft. LH contributed to Supervision, Writing—review & editing, Conceptualization, and Funding acquisition. HB contributed to Writing—review & editing. ZW contributed to Investigation, Data curation. JX contributed to Investigation, Data curation. CZ contributed to Data curation. XY contributed to Data curation. All authors read and approved the final manuscript.

Funding

This work was financially supported by the National Key Research and Development Program of China (2018YFB1501402).

Availability of data and materials

The datasets used or analysed during the current study are available from the corresponding author on reasonable request.

A.T. Hoang, H.C. Ong, I.M.R. Fattah, C.T. Chong, C.K. Cheng, R. Sakthivel, Y.S. Ok, Fuel Process. Technol. 223, (2021) htttps://doi.org/10.1016/j.fuproc.2021.106997
P. Gautam, Neha, S.N. Upadhyay, S.K. Dubey, Fuel. 273, (2020) htttps://doi.org/10.1016/ j.fuel.2020.117783
K. Alper, K. Tekin, S. Karagoz, A.J. Ragauskas, Sustainable Energy & Fuels. 4, 4390 (2020) htttps:// doi.org/10.1039/d0se00784f
Q.D. Hou, X.H. Qi, M.N. Zhen, H.L. Qian, Y.F. Nie, C.Y.L. Bai, S.Q. Zhang, X.Y. Bai, M.T. Ju, Green Chemistry. 23, 119 (2021) htttps://doi.org/10.1039/d0gc02770g
L.F. Chen, Y.H. Xiong, H. Qin, Z.W. Qi, Chemsuschem. 15, (2022) htttps://doi.org/10.1002/ cssc.202102635
Q.S. Kong, X.L. Li, H.J. Xu, Y. Fu, Fuel Process. Technol. 209, (2020) htttps://doi.org/10.1016/ j.fuproc.2020.106528
X. Kong, Y.F. Zhu, Z. Fang, J.A. Kozinski, I.S. Butler, L.J. Xu, H. Song, X.J. Wei, Green Chem. 20, 3657 (2018) htttps://doi.org/10.1039/c8gc00234g
L. Hu, L. Lin, Z. Wu, S.Y. Zhou, S.J. Liu, Renewable & Sustainable Energy Reviews. 74, 230 (2017) htttps://doi.org/10.1016/j.rser.2017.02.042
S.P. Teong, G.S. Yi, Y.G. Zhang, Green Chem. 16, 2015 (2014) htttps://doi.org/10.1039/c3gc42018c
A.I. Torres, M. Tsapatsis, P. Daoutidis, Computers & Chemical Engineering. 42, 130 (2012) htttps:// doi.org/10.1016/j.compchemeng.2011.12.013
V. Choudhary, S.H. Mushrif, C. Ho, A. Anderko, V. Nikolakis, N.S. Marinkovic, A.I. Frenkel, S.I. Sandler, D.G. Vlachos, J. Am. Chem. Soc. 135, 3997 (2013) htttps://doi.org/10.1021/ja3122763
I.K.M. Yu, D.C.W. Tsang, Bioresource Technology. 238, 716 (2017) htttps://doi.org/10.1016/ j.biortech.2017.04.026
H. Li, S. Yang, S. Saravanamurugan, A. Riisager, Acs Catalysis. 7, 3010 (2017) htttps://doi.org/ 10.1021/acscatal.6b03625
W.Q. Wei, S.B. Wu, Chemical Engineering Journal. 307, 389 (2017) htttps://doi.org/10.1016/ j.cej.2016.08.099
D. Garces, E. Diaz, S. Ordonez, Ind. Eng. Chem. Res. 56, 5221 (2017) htttps://doi.org/10.1021/ acs.iecr.7b00952
M. Nahavandi, T. Kasanneni, Z.S. Yuan, C.C. Xu, S. Rohani, Acs Sustainable Chemistry & Engineering. 7, 11970 (2019) htttps://doi.org/10.1021/acssuschemeng.9b00250
W.Z. Guo, H.J. Heeres, J. Yue, Chem. Eng. J. 381, (2020) htttps://doi.org/10.1016/ j.cej.2019.122754
Y.J. Pagan-Torres, T.F. Wang, J.M.R. Gallo, B.H. Shanks, J.A. Dumesic, ACS Catal. 2, 930 (2012) htttps://doi.org/10.1021/cs300192z
J. Zhang, J.Z. Chen, J. Energy Chem. 25, 747 (2016) htttps://doi.org/10.1016/j.jechem.2016.06.005
A. Munyentwali, H. Li, Q.H. Yang, Applied Catalysis a-General. 633, (2022) htttps://doi.org/ 10.1016/j.apcata.2022.118525
J.J. Wang, J.W. Ren, X.H. Liu, J.X. Xi, Q.N. Xia, Y.H. Zu, G.Z. Lu, Y.Q. Wang, Green Chem. 14, 2506 (2012) htttps://doi.org/10.1039/c2gc35699f
I. Jimenez-Morales, M. Moreno-Recio, J. Santamaria-Gonzalez, P. Maireles-Torres, A. Jimenez-Lopez, Appl. Catal. B-Environ. 164, 70 (2015) htttps://doi.org/10.1016/j.apcatb.2014.09.002
T.D. Swift, H. Nguyen, Z. Erdman, J.S. Kruger, V. Nikolakis, D.G. Vlachos, J. Catal. 333, 149 (2016) htttps://doi.org/10.1016/j.jcat.2015.10.009
H.T. Kreissl, K. Nakagawa, Y.K. Peng, Y. Koito, J.L. Zheng, S.C.E. Tsang, Journal of Catalysis. 338, 329 (2016) htttps://doi.org/10.1016/j.jcat.2016.03.007
Y. Shen, Y.R. Kang, J.K. Sun, C. Wang, B. Wang, F. Xu, R.C. Sun, Chinese Journal of Catalysis. 37, 1362 (2016) htttps://doi.org/10.1016/s1872-2067(15)61096-8
M.N. Catrinck, E.S. Ribeiro, R.S. Monteiro, R.M. Ribas, M.H.P. Barbosa, R.F. Teofilo, Fuel. 210, 67 (2017) htttps://doi.org/10.1016/j.fuel.2017.08.035
A. Rezayan, K. Wang, R.F. Nie, J.S. Wang, T.L. Lu, Y.S. Zhang, C.C. Xu, Journal of Catalysis. 414, 186 (2022) htttps://doi.org/10.1016/j.jcat.2022.09.004
A. Mahajan, P. Gupta, Environmental Chemistry Letters. 18, 299 (2020) htttps://doi.org/10.1007/ s10311-019-00940-7
Z.K. Zhang, Z.Y. Zhu, B.X. Shen, L.N. Liu, Energy. 171, 581 (2019) htttps://doi.org/10.1016/ j.energy.2019.01.035
X. Sun, H.K. Atiyeh, M.X. Li, Y. Chen, Bioresource Technology. 295, (2020) htttps://doi.org/ 10.1016/j.biortech.2019.122252
M.G. Mazzotta, D. Gupta, B. Saha, A.K. Patra, A. Bhaumik, M.M. Abu-Omar, ChemSusChem. 7, 2342 (2014) htttps://doi.org/10.1002/cssc.201402007
K. Ke, H.R. Ji, X.N. Shen, F.O. Kong, B. Li, Polymers. 13, (2021) htttps://doi.org/10.3390/ polym13132096
F.R. Tao, H.L. Song, L.J. Chou, RSC Adv. 1, 672 (2011) htttps://doi.org/10.1039/c1ra00088h
T.M.C. Hoang, E.R.H. van Eck, W.P. Bula, J.G.E. Gardeniers, L. Lefferts, K. Seshan, Green Chemistry. 17, 959 (2015) htttps://doi.org/10.1039/c4gc01324g
G. Tsilomelekis, M.J. Orella, Z.X. Lin, Z.W. Cheng, W.Q. Zheng, V. Nikolakis, D.G. Vlachos, Green Chem. 18, 1983 (2016) htttps://doi.org/10.1039/c5gc01938a
D. Jung, P. Korner, A. Kruse, Biomass Convers. Biorefinery. 11, 1155 (2021) htttps://doi.org/ 10.1007/s13399-019-00507-0
S.S. Xiong, C. Luo, Z.H. Yu, N. Ji, L.J. Zhu, S.R. Wang, Green Chemistry. 23, 8458 (2021) htttps://doi.org/10.1039/d1gc01968f
Y. Yang, C.W. Hu, M.M. Abu-Omar, Green Chem. 14, 509 (2012) htttps://doi.org/10.1039/ c1gc15972k
C.D. Jin, N. Xiang, X. Zhu, E. Shuang, K.C. Sheng, X.M. Zhang, Appl. Catal. B-Environ. 285, (2021) htttps://doi.org/10.1016/j.apcatb.2020.119799
P.X. Yan, M. Xia, S.S. Chen, W.Y. Han, H.L. Wang, W.B. Zhu, Green Chem. 22, 5274 (2020) htttps://doi.org/10.1039/d0gc01446j
F. Shen, S. Sun, X. Zhang, J.R. Yang, M. Qiu, X.H. Qi, Cellulose. 27, 3013 (2020) htttps://doi.org/ 10.1007/s10570-020-03008-w
F. Huang, W.Z. Li, T.W. Zhang, D.W. Li, Q.Y. Liu, X.F. Zhu, L.L. Ma, Res. Chem. Intermed. 44, 5439 (2018) htttps://doi.org/10.1007/s11164-018-3432-y
D. Zeng, Q. Zhang, S. Chen, S. Liu, G. Wang, Microporous Mesoporous Mater., (2016)
M.H. Zong, Z.Q. Duan, W.Y. Lou, T.J. Smith, H. Wu, Green Chemistry. 9, 434 (2007) htttps:// doi.org/10.1039/b615447f
M. Nasrollahzadeh, N.S.S. Bidgoli, N. Shafiei, F. Momenbeik, International Journal of Biological Macromolecules. 182, 59 (2021) htttps://doi.org/10.1016/j.ijbiomac.2021.03.191
G.P. Perez, M.J. Dumont, Chemical Engineering Journal. 382, (2020) htttps://doi.org/10.1016/ j.cej.2019.122766
R.S. Thombal, V.H. Jadhav, Applied Catalysis a-General. 499, 213 (2015) htttps://doi.org/10.1016/ j.apcata.2015.04.021
H.Y. Song, C. Xing, B. Li, W.Z. Shen, Chemistryselect. 1, 301 (2016) htttps://doi.org/10.1002/ slct.201500013
M. Kruk, M. Jaroniec, Chemistry of Materials. 13, 3169 (2001) htttps://doi.org/10.1021/cm0101069
A. Ates, Biomass Conversion and Biorefinery. htttps://doi.org/10.1007/s13399-021-01838-7
C.W. Jiang, J.D. Zhu, B. Wang, L. Li, H. Zhong, Chinese Journal of Chemical Engineering. 26, 1270 (2018) htttps://doi.org/10.1016/j.cjche.2018.02.031
A. Taguchi, F. Schuth, Microporous and Mesoporous Materials. 77, 1 (2005) htttps://doi.org/ 10.1016/j.micromeso.2004.06.030
L. Li, T.I. Koranyi, B.F. Sels, P.P. Pescarmona, Green Chemistry. 14, 1611 (2012) htttps://doi.org/ 10.1039/c2gc16619d
F.F. Wang, J. Liu, H. Li, C.L. Liu, R.Z. Yang, W.S. Dong, Green Chemistry. 17, 2455 (2015) htttps:// doi.org/10.1039/c4gc02131b
A. Penkova, L.F. Bobadilla, F. Romero-Sarria, M.A. Centeno, J.A. Odriozola, Applied Surface Science. 317, 241 (2014) htttps://doi.org/10.1016/j.apsusc.2014.08.093
R. Khumho, S. Yousatit, C. Ngamcharussrivichai, Catalysts. 11, (2021) htttps://doi.org/10.3390/ catal11080887
M. Rezaie, M. Dinari, A.N. Chermahini, M. Saraji, A. Shahvar, International Journal of Biological Macromolecules. 165, 1129 (2020) htttps://doi.org/10.1016/j.ijbiomac.2020.09.258
S.H. Dhawane, E.G. Al-Sakkari, G. Halder, Catalysis Letters. 149, 3508 (2019) htttps://doi.org/ 10.1007/s10562-019-02905-5
F. Guo, Z. Fang, T.J. Zhou, Bioresour. Technol. 112, 313 (2012) htttps://doi.org/10.1016/ j.biortech.2012.02.108

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Conversion of glucose into 5-hydroxymethylfurfural by carbonaceous solid acid catalysts loaded with Brønsted acid and Lewis acid in biphasic system

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Journal Publication

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Abstract

Figures

Introduction

Experimental

Materials

Catalysts preparation

Catalysts characterization

Catalytic activity test

Product analysis

Results And Discussion

Catalyst characterization

Conversion of glucose into HMF

Multicycle performance of the carbonaceous solid acid catalyst

Conclusions

Declarations

References

Additional Declarations

Status:

Journal Publication

Version 1