Biomass-based production of trimellitic and trimesic acids

Abstract

The production of industrial chemicals with renewable biomass feedstock holds potential to aid the world in pursuing a carbon-neutral society. Trimellitic and trimesic acids are important commodity chemicals in industry that are prepared by the oxidation of petroleum-derived trimethylbenzene. To reduce the dependence on the limited oil source, we develop a potential sustainable alternative towards trimellitic and trimesic acids using biomass-based 2-methyl-2,4-pentandiol (MPD), acrylate and crotonaldehyde as starting materials. The process for trimellitic acid includes dehydration/D-A reaction of MPD and acrylate, flow aromatization over Pd/C catalyst, hydrolysis and catalytic aerobic oxidation (60% overall yield). The challenging regioselectivity issue of D-A reaction is tackled by a matched combination of temperature and deep eutectic solvent ChCl/HCO2H. Crotonaldehyde can also participate in the reaction, followed by Pd/C-catalyzed decarbonylation/dehydrogenation and oxidation to provide trimesic acid in 54% overall yield. Life cycle assessment implies that compared to conventional fossil process, our biomass-based routes present a potential in reducing carbon emissions. © 2023 Institute of Process Engineering, Chinese Academy of Sciences. Publishing services by Elsevier B.V. on behalf of KeAi Communications Co., Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Headnote

Abstract

The production of industrial chemicals with renewable biomass feedstock holds potential to aid the world in pursuing a carbon-neutral society. Trimellitic and trimesic acids are important commodity chemicals in industry that are prepared by the oxidation of petroleum-derived trimethylbenzene. To reduce the dependence on the limited oil source, we develop a potential sustainable alternative towards trimellitic and trimesic acids using biomass-based 2-methyl-2,4-pentandiol (MPD), acrylate and crotonaldehyde as starting materials. The process for trimellitic acid includes dehydration/D-A reaction of MPD and acrylate, flow aromatization over Pd/C catalyst, hydrolysis and catalytic aerobic oxidation (60% overall yield). The challenging regioselectivity issue of D-A reaction is tackled by a matched combination of temperature and deep eutectic solvent ChCl/HCO2H. Crotonaldehyde can also participate in the reaction, followed by Pd/C-catalyzed decarbonylation/dehydrogenation and oxidation to provide trimesic acid in 54% overall yield. Life cycle assessment implies that compared to conventional fossil process, our biomass-based routes present a potential in reducing carbon emissions. © 2023 Institute of Process Engineering, Chinese Academy of Sciences. Publishing services by Elsevier B.V. on behalf of KeAi Communications Co., Ltd. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Keywords: Biomass; Trimellitic acid; Trimesic acid; Deep eutectic solvent; Dehydration/D-A reaction

1. Introduction

As reported by the Intergovernmental Panel on Climate Change (IPCC), the consumption of fossil energy contributes to 2/3 of the global greenhouse gases (GHGs) emissions, thus resulting in global warming [1]. To address this critical issue, the Paris Agreement aims to limit global warming less than 1.5C in this century, which requires an achievement of carbon neutrality by 2050 [2]. A transition from fossil to renewable biomass energy holds great potential towards this goal. Generally, this emerging technology focuses on the valorization of those platform molecules obtained from the bio-refinery [3–7]. The past decade has witnessed much progress in the preparation of biobased arenes [8–15], monomers [16–25] and organonitrogen compounds [26–31]. Nonetheless, there is still plenty of room for further exploring biomass-based chemical supply chain, due to the great demand for advanced chemicals with various purposes [32].

Trimellitic and trimesic acids, featuring a benzene ring with tricarboxylic acid groups at different positions, are important commodity chemicals in industry. Trioctyl trimellitate (TOTM), an ester of trimellitic acid, is an excellent polyvinyl chloride (PVC) plasticizer with low volatility and has found extensive applications in cable insulation materials, internal electrical parts for the automotive, and flexible films [33].

Trimesic acid, an isomer of trimellitic acid, is one of the most widely used triangular linker for the assembly of metal organic frameworks (MOFs) [34]. In addition, trimesic acid can also be applied in the preparation of dendrimers [35] and polyamide desalination membranes [36]. Currently, these two chemicals are manufactured by the oxidation of petroleumderived trimethylbenzene (Scheme 1, top) [37]. To reduce the reliance on the non-renewable oil source, it is of great significance to exploit a sustainable biomass-based route for producing trimellitic and trimesic acids.

Recently, the group of Xu and Lu accomplished the synthesis of trimellitate via Diels–Alder (D-A) reaction of sugar-derived muconate with acrylate and subsequent dehydrogenation [38]. Considering muconate was produced by deoxydehydration of galactarate with excessive reductant triphenylphosphine [38], from the viewpoint of atom-economy and environmental impact, it is still highly desirable to exploit a catalytic alternative towards renewable trimellitate (or trimellitic acid). 2Methyl2,4-pentandiol (MPD) is easily prepared via domino self-aldol/ hydrogenation of acetone (Scheme 1, bottom) [39,40]. Acrylate, a simple a,b-unsaturated ester, can be made by the dehydration of renewable lactic acid or 3hydroxypropionic acid (3HP) [41,42]. Crotonaldehyde is the self-aldol product of acetaldehyde [43]. With these three platform molecules, an efficient biomass-based route is developed to access trimellitic and trimesic acids (Scheme 1, bottom). In a renewable deep eutectic solvent (DES) [44] formed by choline chloride (ChCl) and formic acid (HCO2H), MPD 1 and acrylate 2 undergo one-step dehydration and D-A reaction to produce adduct 3 in 82% yield. Since D-A reaction can generate two regioisomers, the control of the regioselectivity is a formidable challenge. The temperature and the molar ratio of ChCl/HCO2H are the main contributors to the high regioselectivity. Subsequently, Pd/C-catalyzed dehydrogenation, hydrolysis and aerobic oxidation lead to trimellitic acid 6 (four-step, overall yield 60%). Furthermore, crotonaldehyde 7 can also react with MPD 1 smoothly in ChCl/ HCO2H to deliver adduct 8, followed by Pd/C-catalyzed aromatization and oxidation to give trimesic acid 10 in 54% overall yield. We herein disclose these results.

2. Experimental

2.1. Materials

Ethyl acrylate, 2-methyl-2,4-pentandiol (MPD), choline chloride (ChCl), formic acid, dimethoxyethane (DME) and PEG-400 were provided by Aladdin Industrial Corporation. Crotonaldehyde was purchased from Energy Chemical Company [Emim]Cl was obtained from Lanzhou Institute of Chemical Physics. The commonly used solvents including Nmethyl pyrrolidone (NMP), dimethyl sulfoxide (DMSO), toluene, and 1,4-dioxane were supplied by Damao Chemical Reagent Factory. The internal standard dodecane was obtained from TCI Chemical Company. All chemicals were of analytical grade and were used without further purification. The Pd/ C catalyst was obtained from Aladdin Industrial Corporation. Nafion resin was purchased from Jiangsu Success Resin Corporation.

2.2. Preparation of deep eutectic solvent (DES) ChCl/ HCO2H

Choline chloride (ChCl, 0.075 mol, 10.5 g) and HCO2H (0.05 mol, 2.5 g) were added to a 100 mL round bottom flask. Then the mixture was stirred at 100C for 30 min until a homogenous solution with viscosity was formed. Approximately 20 mg of the sample was transferred into a NMR tube and dissolved in 0.5 mL of d6-DMSO. NMR spectra were recorded at room temperature on 400 MHz spectrometer.

2.3. One-step dehydration/D-A reaction over ChCl/ HCO2H

In a sealed tube (35 mL), 2-methyl-2,4-pentandiol (1.18 g, 10.0 mmol), ethyl acrylate (545 mL, 5.0 mmol) and ChCl/ HCO2H (molar ratio 1.5:1, 2.3636 g) were added in sequence. The system was stirred at 110C for 24 h. Alternatively, a mixture of 2-methyl-2,4-pentandiol (0.59 g, 5.0 mmol) and ChCl/HCO2H (molar ratio 1.5:1, 2.3636 g) was first stirred at 110C for 24 h. Then without separation, crotonaldehyde (410 mL, 5.0 mmol) was added and stirred at 140C for 24 h.

Upon completion, the system automatically separated into two phases. The upper layer was the D-A product, while the lower layer was byproduct water and DES ChCl/HCO2H. After cooling at 0C for a period of time, the lower layer became solid and the liquid product (upper layer) could be easily separated just by decantation. The yield and regioselectivity were determined by an Agilent GC 7890 A equipped with HP-5 column (30 m, 0.25 mm ID, 0.5 mm film) and a flame ionization detector (FID) using dodecane as the internal standard. Approximately 20 mg of the corresponding product was transferred into a NMR tube and dissolved in 0.5 mL of CDCl3. NMR spectra were recorded at room temperature on 400/700 MHz spectrometers.

2.4. Pd/C-catalyzed aromatization in a continuous flow reactor

In a fixed bed reactor, Pd/C (0.3 g) was introduced. At 220C, ethyl 2,4-dimethylcyclohex-3-ene-1-carboxylate or 2,4,6-trimethylcyclohex-3-ene-1-carbaldehyde was fed into the reactor from the bottom via a HPLC pump (flow rate: 0.04 mL min1 ) along with nitrogen gas (1.0 atm) at a flow rate of 120 mL min1 . The process flow diagram for this reaction was given in Scheme 2. After reaction for 6 h, the product was drained from the gasliquid separator and analyzed by the Agilent GC 7890 A equipped with an HP-5 column (30 m, 0.25 mm ID, 0.5 mm film) and a FID using dodecane as the internal standard. Approximately 20 mg of the corresponding product was transferred into a NMR tube and dissolved in 0.5 mL of CDCl3. NMR spectra were recorded at room temperature on 400/700 MHz spectrometers.

2.5. Production of trimellitic and trimesic acids via catalytic aerobic oxidation

To a 50 mL autoclave reactor was sequentially added 2,4dimethylbenzoic acid or mesitylene (1.0 mmol), Co(OAc)2 (5% mol/mol), Mn(OAc)2 (5% mol/mol), KBr (10% mol/mol) and acetic acid (3.0 mL). Then the autoclave was sealed and purged with 1 MPa O2 for ten times to remove the remaining air in the reactor. After that, the oxygen pressure was adjusted to 1.5 MPa and the reaction was conducted at 120C for 24 h. Upon completion, acetic acid was removed via rotary evaporation. The crude residue was crystallized with ethanol/ acetone to afford trimesic acid as a white solid. Approximately 20 mg of the corresponding product was transferred into a NMR tube and dissolved in 0.5 mL of d6-DMSO. NMR spectra were recorded at room temperature on 400/700 MHz spectrometers.

3. Results and discussion

3.1. One-step dehydration/D-A reaction between MPD and acrylate

At the outset, the solvent effects on the reaction of MPD 1 and acrylate 2 were examined at 120C with commerical solid acid Nafion resin as catalyst (Table 1). The desired one-step dehydration/D-A reaction could take place in ether solvents such as dioxane and dimethoxyethane (DME), but the yield and regioselectivity of product 3 were rather low (entries 1, 2). The protic solvents polyethylene glycol 400 (PEG-400) and water could not give better results (entries 3, 4). In comparison, strong polar aprotic solvents N-methyl pyrrolidone (NMP) and dimethyl sulfoxide (DMSO) led to an improvement in the yield and regioselectivity (entries 5, 6). When ionic liquid 1-ethyl-3-methylimidazolium chloride ([Emim] Cl) was used as reaction medium, a comparable result was obtained (entry 7). Considering biodegradable deep eutectic solvent (DES) possesses strong electrostatic force and hydrogen-bonding interactions [44,45], we further tested the transformation in neutral DES formed by ChCl and ethylene glycol (EG) or glycerol (molar ratio of 1:1). Both DESs gave rise to product 3 in better yields (entries 8, 9). The reaction in acidic DES ChCl/HCO2H took place smoothly without any catalyst, affording 3 in 65% yield with 4.9/1 regioselectivity (entry 10). ChCl/HOAc gave an inferior result (entry 11). The temperature exerted a significant impact on the outcome. The regioselectivity decreased at an elevated temperature (entry 12, GC chromatogram see Scheme 3), while lower temperatures resulted in a decline in the yield (entries 13–15). When prolonging the reaction time to 24 h at 110C, the yield of 3 remained comparable with an increased regioselectivity (entry 16, GC chromatogram see Scheme 3). The reaction did not occur in sole ChCl, while a complex mixture (diene intermediates and their dimers/trimers) was observed in HCO2H solvent (entries 17, 18). This phenomenon implies that the property of the formed DES is the key to the good performance.

Fig. 1 depicts the yield and regioselectivity of adduct 3 as a function of the molar ratio of ChCl/HCO2H. Gratifyingly, when increasing molar ratio (ChCl/HCO2H) to 1.5:1, the yield varied a little, but the regioselectivity was greatly improved to > 20/1 (GC chromatogram see Scheme 3). A further increment led to a decreased yield, although the selectivity still remained high. In contrast, increasing the amount of HCO2H gave rise to 3 in a low regioselectivity. In this case, a large excess of acid also coordinates with acrylate through hydrogen-bonding. This interaction can lower the energy barrier of D-A reaction but increase the steric hindrance of acrylate, thus leading to the formation of the other regioisomer 3'.

With the optimal DES system (ChCl/HCO2H ¼ 1.5:1) in hand, we checked its reusability for the reaction between MPD and acrylate at a moderate activity level. When the mixture was stirred at 110C for 24 h, the system automatically separated into two phases (Fig. 2b). The upper layer was the product 3, whereas the lower layer was byproduct water and DES ChCl/HCO2H. In particular, after cooling at 0C for a period of time, the lower layer became solid and product 3 (upper layer) could be easily separated just by decantation (Fig. 2c). The lower layer was dried at 60C for 1 h under vacuum to remove the byproduct water. The recovered DES was then reused for the next cycle. As shown in Fig. 3, there was no significant variation in the yield of product 3 after recycling for three times. These two salient features (i.e. facile separation and good reusability) are very advantageous in practical applications. Since the boiling point of formic acid was very close to that of water, it is necessary to confirm whether formic acid can also be removed under the vacuum conditions. Based on HPLC chromatograms of fresh and used DES ChCl/HCO2H (Figs. S3 and S4 in SI, page S11), the area of HCO2H was comparable, indicating that HCO2H could not be removed during the desiccation step. This phenomenon is likely ascribed that the hydrogen-bonding of choline chloride and formic acid is stronger than that of water and DES components.

Subsequently, the influence of molar ratio of substrates on the reaction was investigated (Fig. 4). The employment of an excessive amount of MPD 1 led to an evident enhancement in the yield. The best result (82% yield) was attained when 2.0 equivalent of MPD was used. Based on the time course analysis (Fig. S1), the yield kept increasing over time and remained constant after 22 h. Therefore, 24 h was enough to ensure the reaction efficiency.

To determine the reaction sequence, a one-pot two-step process was performed (Scheme 4). An initial dehydration of MPD in ChCl/HCO2H at 110C gave rise to a mixture of 4methylpenta-1,3-diene A and (E )-2-methylpenta-1,3-diene B with molar ratio of 1/1.5. Then acrylate 2 was introduced and the system was further stirred at 110C for 24 h. It is found that this procedure furnished the target adduct 3 (derived from diene B) in a comparable yield, while compound 3" (derived from diene A) was not detected at all. Besides, the D-A reaction between isolated dienes (A/B ¼ 1/1.5) and acrylate proceeded smoothly as well at 110C under solvent-free condition or in fresh DES ChCl/HCO2H and the desired adduct 3 was obtained in a comparable yield (Scheme 4). These results illustrate that acidic DES exerts a minimal influence on the D-A reaction, and the rate of D-A reaction between diene B and acrylate 2 is likely much faster than that of A and 2, thereby shifting the equilibrium from A towards B.

3.2. Pd/C-catalyzed aromatization of D-A adduct

The catalytic dehydrogenation of adduct 3 was then surveyed. According to the literature [46,47], commercially available Pd/C often shows good dehydrogenation activity. Accordingly, Pd/C was chosen as the catalyst to study the temperature effect in a continuous flow reactor. When the reaction was conducted at 180C under nitrogen atmosphere, the desired aromatic product 4 was indeed afforded with 62% yield. The efficiency increased with raising the temperature and reached the maximum (88%) at 220C. An inferior result was attained at higher temperature because side decarboxylation took place under this condition (Fig. 5). Notably, stability test of Pd/C catalyst revealed that there was no evident steadily over Pd/C catalyst (88% yield) and the drained product 2,4-dimethylbenzoate was hydrolyzed to 2,4-dimethylbenzoic acid in the presence of base (93% yield). A final aerobic oxidation with a catalytic amount of Mn(OAc)2, Co(OAc)2, and KBr at 120C delivered trimellitic acid in 89% yield [24]. Consequently, starting from renewable MPD and acrylate, a four-step route was established for the preparation of trimellitic acid in 60% overall yield. 3.4. Production of trimesic acid with MPD and crotonaldehyde Crotonaldehyde is a methyl substituted a,b-unsaturated aldehyde that is produced by self-aldol reaction of acetaldehyde [43]. We proposed that if crotonaldehyde could also react with MPD to yield D-A adduct, then further aromatization and oxidation would give rise to advanced chemical trimesic acid. Bearing this idea in mind, we first carried out one-step dehydration/D-A reaction of MPD 1 and crotonaldehyde 7 in ChCl/HCO2H at 110C. Disappointedly, no D-A product was observed, which was ascribed that undesired hemiacetal/acetal was formed under acidic conditions. As a result, a one-pot two-step procedure was attempted (Fig. 7). To do this, the solution of MPD and ChCl/HCO2H was stirred at 110C for 24 h. After the dehydration completed, crotonaldehyde 7 was added and the mixture was further stirred at 110C for 24 h. Through this operation, the target adduct 8 was delivered in 67% yield. The temperature decrease in the dehydrogenation activity during 24 h time on stream (Fig. 6).

3.3. A whole process for the production of trimellitic acid with MPD and acrylate

Scheme 5 shows the process for the production of trimellitic acid with MPD and acrylate. The MPD and acrylate were co-fed to the reactor containing DES ChCl/HCO2H. After stirring at 110C for 24 h, the D-A adduct (upper layer) was easily separated by decantation (82% yield), and the ChCl/HCO2H (lower layer) was reused after a desiccation treatment. Subsequently, a flow aromatization took place steadily over Pd/C catalyst (88% yield) and the drained product 2,4-dimethylbenzoate was hydrolyzed to 2,4-dimethylbenzoic acid in the presence of base (93% yield). A final aerobic oxidation with a catalytic amount of Mn(OAc)2, Co(OAc)2, and KBr at 120C delivered trimellitic acid in 89% yield [24]. Consequently, starting from renewable MPD and acrylate, a four-step route was established for the preparation of trimellitic acid in 60% overall yield.

3.4. Production of trimesic acid with MPD and crotonaldehyde

Crotonaldehyde is a methyl substituted a,b-unsaturated aldehyde that is produced by self-aldol reaction of acetaldehyde [43]. We proposed that if crotonaldehyde could also react with MPD to yield D-A adduct, then further aromatization and oxidation would give rise to advanced chemical trimesic acid. Bearing this idea in mind, we first carried out one-step dehydration/D-A reaction of MPD 1 and crotonaldehyde 7 in ChCl/HCO2H at 110C. Disappointedly, no D-A product was observed, which was ascribed that undesired hemiacetal/acetal was formed under acidic conditions. As a result, a one-pot two-step procedure was attempted (Fig. 7). To do this, the solution of MPD and ChCl/HCO2H was stirred at 110C for 24 h. After the dehydration completed, crotonaldehyde 7 was added and the mixture was further stirred at 110C for 24 h. Through this operation, the target adduct 8 was delivered in 67% yield. The temperature for the second step was screened as well. An improvement in the yield was observed with increasing the temperature and the maximum yield (82%) was achieved at 140C. A higher temperature led to a decrease in the efficiency, due to the dimerization of diene intermediates.

The aromatization of adduct 8 took place smoothly over Pd/ C catalyst in a fixed-bed reactor, giving mesitylene 9 in 75% yield via a sequential decarbonylation/dehydrogenation process (Scheme 6) [48]. A final catalytic aerobic oxidation with Co/ Mn/Br produced trimesic acid 10 in 88% yield. Hence, with MPD and crotonaldehyde as feedstocks, a three-step avenue was developed to access trimesic acid in 54% overall yield.

Based on life cycle thinking, quantitative study of chemical environmental properties can serve as a foundation for technological development and decision-making. Life cycle assessment (LCA), a strategy for quantifying a product's potential environmental impact [49], is utilized in this work to compare trimellitic and trimesic acids prepared by bio-derived or fossil routes. We used the global warming potential (GWP) to compare two chemicals from the cradle-to-gate system boundary (Fig. 8) in accordance with ISO 14040 [50] and ISO 14044 [51].

As shown in Fig. 8, the system boundary includes biomassbased raw materials production, raw materials and energy consumption, biomass conversion process, and waste treatment. For characteristic analysis, 1 kg of chemical was defined as the functional unit, as stated in the system boundary. Foreground data, such as adduct synthesis process and conversion of materials, are derived from the experimental data, while the background data, such as energy consumption, are directly obtained from the database of commercial analysis software. It should be noted that when a byproduct output is involved in the process route, the environmental burden is distributed via the mass-based allocation method. The GWP of trimellitic and trimesic acids from the fossil-based route is directly converted from the Ecoinvent database.

Carbon footprint results of two chemicals via biomass- and fossil-based pathways are shown in Fig. 9. It can be clearly seen that bio-routes have obvious advantages of carbon emission reduction compared with fossil route. Especially for trimesic acid (compound 10), the emission reduction potential of bio-route one can come up to 82%, which is mainly related to the designed synthesis method and production path. Trimellitic acid (compound 6) from the fossil route is easy to be prepared from C9 aromatics, so bio-based one shows a mild emission reduction potential of 34%.

Furthermore, in order to investigate the key emission reduction factors, we examined the cumulative contribution of the carbon footprint of bio-routes, as shown in Fig. 10. For trimesic acid, the most significant contributor is biomassbased chemicals, which comprises MPD together with crotonaldehyde and accounts for more than 47% to the GWP. The main reason is that the conversion of biomass to MPD and crotonaldehyde is a multi-step process, which weakens the carbon reduction advantages of this renewable resource. In addition, it is worth noting that the consumption of electricity and solvent significantly contributes to GWP. The GWP results for electricity and solvents accounted for 27.96% and 22.82%, respectively. Due to the reusable nature of the catalyst, its contribution to the GWP results is minimal. For trimellitic acid, there is no significant difference between its carbon footprint and that of trimesic acid, which is mainly related to the production process of biomass-based starting materials MPD and acrylate. Consequently, it is suggested that optimizing the process for the production of renewable MPD and reducing the amount of solvent can further improve the environmental profile of trimesic and trimellitic acid while also enhance the potential of biomass-based routes.

4. Conclusions

In summary, we have accomplished a potential renewable route for the production of trimellitic and trimesic acids using biomass-derived 2-methyl-2,4-pentandiol (MPD), acrylate and crotonaldehyde as the feedstocks. The avenue towards trimellitic acid includes dehydration/D-A reaction of MPD and acrylate, Pd/C-catalyzed dehydrogenation, hydrolysis and catalytic aerobic oxidation (60% overall yield). The challenging regioselectivity issue of D-A reaction was tackled by a matched combination of temperature and DES ChCl/HCO2H. Crotonaldehyde could also participate in the reaction, followed by Pd/C-catalyzed decarbonylation/dehydrogenation and oxidation to furnish trimesic acid in 54% overall yield. Life cycle assessment revealed that our biomass-based routes showed a promising potential in reducing carbon emissions compared with conventional fossil pathways. The main obstacle for the industrialization is the production of starting materials MPD, acrylate, and crotonaldehyde with biomass, which generally involves a multi-step process and is the main contributor of greenhouse gases emissions. Therefore, future endeavor to optimize the renewable process towards the starting chemicals is the key in pursuit of the industrialization.

Conflict of interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

This work was supported by the National Key R&D Program of China (no. 2022YFA1504902; 2022YFB4201802), National Natural Science Foundation of China (no. 21721004; 21801239; 22178335; 22078318), DICP (Grant: DICP I201944), the Joint Fund of the Yulin University and the Dalian National Laboratory for Clean Energy (grant: YLUDNL Fund 2021020).

Sidebar

Received 7 November 2022; revised 14 January 2023; accepted 6 February 2023 Available online 9 February 2023

Footnote

* Corresponding authors. E-mail addresses: [email protected] (Y. Hu), [email protected] (F. Wang), [email protected] (N. Li).

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Appendix A. Supplementary data

Supplementary data to this article can be found online at https://doi.org/10.1016/j.gee.2023.02.004.