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The effect of gamma radiation on 5-hydroxymethylfurfural conversion in water and dimethyl sulfoxide

  • Nurulsafeelanaria Benwannamas , Phongphak Sataman , Somprasong Thongkham , Wilasinee Kingkam , Wiranee Sriwiang , Sakchai Laksee , Nicha Prigyai , Tanagorn Sangtawesin EMAIL logo and Threeraphat Chutimasakul EMAIL logo
Published/Copyright: March 13, 2024
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Open Chemistry
From the journal Open Chemistry Volume 22 Issue 1

Abstract

5-Hydroxymethylfurfural (HMF) is a biomass-based chemical platform that can undergo many feasible reactions. One of the most important reactions is the oxidation to 2,5-furandicarboxylic acid (FDCA), which is the monomer for bioplastic production. In this work, the radiation method was used to investigate the conversion of HMF in both aqueous (DI) and dimethyl sulfoxide (DMSO) solutions. The effects of media solvents, atmospheric gases, HMF concentrations, additive bases, and absorbed doses of gamma radiation were studied. The results showed that the media solvent played a crucial role in HMF conversion under gamma irradiation. At 30 kGy, the HMF conversions in DI and DMSO were 92.1 and 24.1%, respectively, and the oxidation products were only found in the irradiated samples under DMSO. The HMF conversion and oxidation product formation increased with the gamma radiation dose. Moreover, it was found that FDCA stability toward gamma irradiation is highly sensitive in aqueous solution but relatively stable in DMSO. The results implied the alternative promising choice of radiation method compared with traditional methods. To join the bridge, the use of a mixture solvent DI/DMSO seems considerable in the future.

Graphical abstract

Keywords: 5-hydroxymethylfurfural; gamma radiation; HMF conversion; 2,5-furandicaboxylic acid; HMF oxidation

Nomenclature

HMF

5-Hydroxymethylfurfural

FDCA

2,5-Furandicaboxylic acid

DFF

2,5-Diformylfuran

HMFCA

5-Hydroxymethyl-2-furancarboxylic acid

FFCA

5-Formyl-2-furancarboxylic acid

LCB

Lignocellulosic biomass

MF

5-Methylfurfural

BHMF

2,5-Bis(hydroxymethyl)furan

PEF

Polyethylene furanoate

PET

Polyethylene terephthalate

HPLC

High-performance liquid chromatography

DFT

Density-functional theory

LUMO

Least unoccupied molecular orbital

Na2CO3

Sodium carbonate

NaHCO3

Sodium bicarbonate

KOH

Potassium hydroxide

K2CO3

Potassium carbonate

NaOH

Sodium hydroxide

TFA

Trifluoroacetic acid

DI

Deionized water

LA

Levulinic acid

FA

Formic acid

DMSO

Dimethyl sulfoxide

DMF

Dimethyl formamide

THF

Tetrahydrofuran

ACN

Acetonitrile

1 Introduction

5-Hydroxymethylfurfural (HMF) was discovered by Düll and Kiermayer [1] in the late eighteenth century. Its versatile applications and great capabilities to replace fossil-fuel utilization allowed it to be denoted a sleeping giant and listed as one of the top ten chemical platforms for sustainable development in the chemical industry by the US Department of Energy since 2004 [2]. It can be synthesized from lignocellulosic biomass (LCB) by hydrolysis of carbohydrates into hexose sugars (i.e., glucose and fructose), followed by dehydration to HMF. Even though the concept of this process seems simple, the formation of side reactions [3], such as hydrolysis to levulinic acid (LA) and formic acid (FA) and cross polymerization to soluble polymer and insoluble humin, sometimes raises the complexity. One of the factors that was considered to improve the selectivity for HMF formation is the media solvent. The integration of a polar aprotic solvent such as dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), tetrahydrofuran (THF), acetonitrile (ACN), and acetone into the synthetic system revealed a better yield of HMF than conducting in a water-only system [4]. DMSO is the most favorable choice among those candidates due to its ability to strongly bind with both substituted groups of HMF, which enhanced its LUMO energy, suppressing the side reactions [5], as reported in Bhaumik and Dhepe [6] and Yu’s works [7].

The structure of HMF consists of a furan ring substituted by aldehyde and hydroxymethyl groups at the C2 and C5 positions, respectively. HMF is an important platform that can convert into various value-added chemicals, as shown in Scheme 1. By opening the ring or modifying the functional groups, it can undergo many feasible reactions, including rehydration to LA and FA [9], ring-opening oxidation to succinic acid [10], hydrogenation to 5-methylfurfural (MF) [11] or 2,5-bis(hydroxymethyl)furan (BHMF) [12], ring cleavage to hexanediol [13] or hexanedione [14], and condensation and hydrodeoxygenation to alkane [15]. Moreover, oxidation of its substituted groups leads to the formation of various valuable compounds, including 2,5-diformylfuran (DFF) [16], 5-hydroxymethyl-2-furancarboxylic acid (HMFCA) [17], 5-formyl-2-furancarboxylic acid (FFCA) [18], and 2,5-furandicarboxylic acid (FDCA) [19], as shown in Scheme 2 [20]. Interestingly, all compounds can be applied in many applications; DFF is the platform molecule for fine chemicals and pharmaceutical drugs [16], and HMFCA is the monomer to prepare furanic polyesters and is used for anticancer and interleukin inhibitors in the pharmacy industry [17]. FFCA is an important intermediate in the production of FDCA, which is a monomer in bioplastic production. Polymerization of FDCA with ethylene glycol produces polyethylene furanoate (PEF), which can act in a manner similar to a well-known petroleum-based polyethylene terephthalate (PET) [20].

Scheme 1 Potential chemical compounds derived from 5-HMF [8].
Scheme 1

Potential chemical compounds derived from 5-HMF [8].

Scheme 2 Oxidation pathway of HMF to FDCA.
Scheme 2

Oxidation pathway of HMF to FDCA.

In the last 20 years, over 2,000 studies on HMF-derived FDCA have been published [21], and the most commonly used method reported in the literature is conventional heating with the addition of metal catalysts and oxidizing agents [21,22]. Recently, the microwave irradiation method has also been reported [23,24]. These traditional methods showed favorable outcomes in terms of yield and selectivity. However, they required the chemical additives as well as the operation under high temperatures (100–150˚C) and high pressures (>0.3 MPa) with reaction times of 2–24 h [23], which allowed the enlargement of chemical waste and extended cost, risk of explosion, and difficulty to upscale. To the best of our knowledge, there is no report on gamma irradiation methods in this aspect. The use of gamma irradiation was believed to overcome the extreme conditions and chemical addition due to the ability to penetrate radiation and self-generate the active free radicals via excitation and ionization, as well as allow the convenience for large-scale production [25,26]. The reaction can be performed in up-scale size and can be used as the catalytic agent for large chemical production in the industries [25]. For example, radiolysis of water gives rise to both reducing agents ( e eq − , H•, H2) and oxidizing agents (HO•, H2O2, H3O+) as shown in equation (1) [27,28]:

(1) H 2 O γ → [ 2.8 ] HO • + [ 2.7 ] e aq − + [ 0.6 ] H • + [ 0.72 ] H 2 O 2 + [ 2.7 ] H 3 O + + [ 0.45 ] H 2 ,

where the values in brackets are the number of each molecule generated per 100 eV (G-value). It is worth noticing from the equation that the oxidizing species are generated in higher amounts than the reducing agent. Taking the benefit from these advantages, gamma irradiation was a novel choice for HMF oxidation.

This project provided an important opportunity to advance the understanding of the radiation process for HMF conversion. The effects of solvents (water and DMSO), atmospheric gases (air, N2, O2, and N2O), initial concentration of HMF, additives, and gamma doses were studied. Water was reported as a general solvent for the HMF reaction, which gave a high yield, but there were several by-products; however, DMSO had a few issues. The stability of FDCA and the potential oxidation products of HMF were also studied under gamma irradiation.

2 Experimental

2.1 Materials and instruments

5-Hydroxymethylfurfural (HMF), 2,5-furandicarboxylicaldehyde (DFF), and 2,5-Furandicarboxylic acid (FDCA) were purchased from Sigma-Aldrich. 5-Hydroxymethyl-2-furancarboxylic acid (HMFCA) and 5-formyl-2-furancarboxylic acid (FFCA) were purchased from TCI. The bases used in this work, including sodium hydroxide (NaOH), sodium carbonate (Na2CO3), sodium bicarbonate (NaHCO3), potassium hydroxide (KOH), and potassium carbonate (K2CO3) were purchased from Merck, ALPHA CHEMIKA, Ajax Finechem, KEMAUS, and Daejung, respectively. Trifluoroacetic acid (TFA) was purchased from Merck, and DMSO was purchased from RCI Labscan. All chemicals were of analytical grade and used as received without further purification. Methanol (HPLC grade) was purchased from Fisher Chemical. Deionized water (DI) was collected from ultra-pure water ASTM Type I, ThermoScientific, with a resistivity > 18.2 MΩ. Gamma radiation was generated from a cobalt-60 irradiator (30366 Ci) coupled with Harwell Amber Perspex dosimeter with a dose rate of 1.7 kGy/h.

2.2 Experimental setup

The experiments on HMF conversion under gamma irradiation were conducted in three duplicates. Primarily, liquid HMF was added into a 10 mL amber vial and dissolved with either DI or DMSO. In an aqueous solution, an equivalence of base was mixed into the vial. The mixture was covered and bubbled with gas for 5 min. The solution was then irradiated under gamma radiation to the target absorbed dose. The recovered sample would be worked up and subsequently analyzed by high-performance liquid chromatography (HPLC, Waters 2695) coupled with a UV-visible detector (Waters 2489) at wavelengths of 280 and 254 nm using ZORBAX C18 reverse column and 0.1% TFA/MeOH (80:20) mobile phase. The stabilities of FDCA in both solvents were also determined by a similar process under ambient conditions.

3 Results and discussion

3.1 Effect of atmospheric gases and media solvents

In this work, the conversion of HMF and the subsequent oxidation product formation under gamma irradiation were investigated. First, the experiment was conducted at 30 kGy with varied atmospheric gases and media solvents. According to radiation chemistry, the reaction system filled with oxygen or nitrous gas was assumed to scavenge electrons ( e eq − ), rendering the whole system environment to a more oxidized condition after gamma irradiation, as described in the equation (1) [29]. The system filled with nitrogen aimed to reduce the amount of dissolved oxygen in the solvent [30]. The reaction under an ambient atmosphere (without bubbling of gas) was also conducted for comparison. However, the obtained results, depicted in Figure 1, exhibited no significant difference in the HMF conversion regarding the atmospheric gas variation.

Figure 1 Effect of the atmospheric gas and media solvent variation on the conversion of HMF under gamma irradiation at 30 kGy (reaction conditions: HMF 0.1 mmol, solvent (DI or DMSO) 10.0 mL, bubbled gas: N2, O2, or N2O).
Figure 1

Effect of the atmospheric gas and media solvent variation on the conversion of HMF under gamma irradiation at 30 kGy (reaction conditions: HMF 0.1 mmol, solvent (DI or DMSO) 10.0 mL, bubbled gas: N2, O2, or N2O).

On the other hand, media solvent played an important role in the HMF conversion and oxidative products. HMF conversion in aqueous solution is much greater than in DMSO. Unfortunately, conversion up to 92.1% in aqueous solution led to other side reactions, as shown in Table 1, which is suspected to rehydrate back to LA and FA [31]. The HMF rehydration pathway is suggested to consist of the formation of 2,5-dioxo-3-hexenal, followed by the decomposition to LA and FA, as shown in Scheme 3 [9]. According to Zhang and Weitz’s report [32], 13C-labeled HMF showed that the breaking at the C1–C2 position of HMF led to the transformation of HMF to FA, and the C6 position of HMF was mapped onto the carbon of LA. The results confirmed the rehydration reaction of HMF to LA and FA (Scheme 3). In addition, the analysis of the products from the conversion of HMF in water was investigated using a liquid chromatography-mass spectrometer (LC-MS), provided in the supporting information as shown in Figure S1. There were peaks at 115 m/z, corresponding to LA, and at 127 m/z, corresponding to the remaining HMF. However, FA cannot be detected because its molecular weight is lower than that of a liquid chromatography-mass instrument.

Table 1

HMF conversion, the oxidation product yield, and selectivity induced by gamma irradiation in aqueous and DMSO solution with various atmospheric gases (reaction conditions: HMF, 0.1 mmol; solvent: 10.0 mL DI or DMSO; bubbled gas: N2, O2, or N2O, at 30 kGy)

Entry Solvent Gas HMF conversion (%) HMFCA yield (%) HMFCA selectivity (%) FFCA yield (%) FFCA selectivity (%)
1 DI Ambient 92.1 ± 1.5 ND ND ND ND
2 N2 87.8 ± 0.6 ND ND ND ND
3 O2 86.3 ± 2.1 ND ND ND ND
4 N2O 89.9 ± 3.0 ND ND ND ND
5 DMSO Ambient 21.8 ± 2.2 3.3 14.9 9.3 43.0
6 N2 21.6 ± 0.4 3.0 13.9 8.4 38.7
7 O2 24.1 ± 1.6 3.2 13.1 9.1 37.6
8 N2O 21.4 ± 0.5 3.5 16.4 8.1 37.9

Note: ND: not determined.

Scheme 3 Rehydration pathway of HMF to LA and FA [9].
Scheme 3

Rehydration pathway of HMF to LA and FA [9].

The oxidation beyond FDCA is another possibility of HMF conversion in an aqueous solution, so this assumption would later be proved by investigating FDCA stabilities under gamma irradiation in both solvents. This research focused on the investigation of the radiation effect on HMF conversion; therefore, no catalysts were used in this experiment, resulting in low selectivity of the oxidative products.

For DMSO, some HMFCA (3.0–3.5% yield) and FFCA (8.1–9.3% yield) are detected in the reaction in DMSO even when HMF conversion was only 21.4–24.1%. The relatively low conversion confirmed the tolerance of HMF in this polar aprotic solvent (DMSO). Low HMF conversion may result from the formation of reducing agents (H2, CH4, and C2H6) during gamma irradiation, as shown in equation (2) [33]. However, better selective oxidative products in HMF were oxidized to HMFCA, FFCA, and FDCA. Therefore, the further experiments were focused on using DMSO as a solvent:

(2) CH 3 SOCH 3 γ → [ 0.2 ] H 2 + [ 3.3 ] CH 4 + [ 0.49 ] C 2 H 6 + [ 1.2 ] ( CH 3 ) 2 S .

3.2 Effect of initial HMF concentration on HMF conversion at different gamma doses

As mentioned previously, HMF is more stable in DMSO and also more selective to oxidative products to the FDCA production pathway because DMSO can suppress the rehydration and polycondensation of HMF, which are the side reactions that occur in the water system [34]. Therefore, the insight experiment was then carried out in DMSO with the variation of HMF concentration to further investigate the conversion trend and the dependency of the oxidation product formation at gamma irradiations of 0, 10, 20, and 30 kGy. The HMF conversion and oxidative products increased significantly as the gamma dose increased, as shown in Figure 2. Approximately 5% of HMF conversion was found without gamma irradiation [35]. DMSO was initially associated with the hydroxyl group of HMF to form a DMSO-mediated reaction, followed by the free hydroxyl group of another HMF replacing the DMSO associated by the SN2 reaction to provide oxo-bis(5-methyl-2-furaldehyde) [35]. However, no oxidation products were found in all non-irradiated samples (0 kGy).

Figure 2 Effect of the initial HMF concentration and absorbed dose of gamma radiation variation on the conversion of HMF under gamma irradiation (reaction conditions: various HMF concentrations: 10, 25, 50, and 100 mM; DMSO, 10.0 mL; ambient gas: at 0, 10, 20, and 30 kGy).
Figure 2

Effect of the initial HMF concentration and absorbed dose of gamma radiation variation on the conversion of HMF under gamma irradiation (reaction conditions: various HMF concentrations: 10, 25, 50, and 100 mM; DMSO, 10.0 mL; ambient gas: at 0, 10, 20, and 30 kGy).

The effect of the initial HMF concentration was investigated. The HMF conversion increased as the initial concentration of HMF decreased; that is, the formation of these oxidation products required sufficient radiation energy for each concentration. The reaction may occur via the radical pathway involving bond breaking, crosslinking, or mixing. This would relate to the proposed mechanism of HMF conversion, as mentioned previously. Ramírez-Cahero and Valdivia-López [36] reported the effect of gamma radiation on furanoids, where HMF is sensitive to radiation and can decompose to a greater extent. Their results indicated that the aldehyde functional group of HMF is more favorable to oxidation than its hydroxymethyl group, leading to the high formation of HMFCA. Thus, the oxidation pathway of HMF by gamma radiation might undergo HMFCA (Scheme 1, Route 2). According to our results, the best HMF conversion was at an HMF concentration of 10 mM at 30 kGy, in which HMFCA and FFCA yields were 3.3 and 9.3%, respectively (Table 2). Notably, the yield obtained from the oxidation products is around half of the calculated conversion of HMF (Table 2). The remaining conversion may reduce to BHMF or other reduced products due to the generation of a reducing agent (H2) from radiolysis of DMSO, as shown in equation (2). There are many reports that the hydrogenation of HMF requires H2 in the reaction [37,38]

Table 2

HMF conversion, yield of the oxidation product, and selectivity induced by gamma irradiation with initial HMF concentration variation in DMSO solution (reaction conditions: various HMF concentrations: 10, 25, 50, and 100 mM; DMSO, 10.0 mL; ambient gas, at 0, 10, 20, and 30 kGy)

Entry HMF concentration (mM) Gamma dose (kGy) HMF conversion (%) HMFCA yield (%) HMFCA selectivity (%) FFCA yield (%) FFCA selectivity (%)
1 10 0 7.1 ± 1.0 ND ND ND ND
2 10 19.4 ± 2.6 1.5 7.8 ND ND
3 20 21.5 ± 1.5 2.6 12.0 7.5 34.9
4 30 21.8 ± 2.2 3.3 14.9 9.3 43.0
5 25 0 4.2 ± 2.2 ND ND ND ND
6 10 13.6 ± 1.2 ND ND ND ND
7 20 18.7 ± 3.2 2.9 15.5 3.3 17.6
8 30 21.2 ± 2.3 3.5 16.7 3.6 17.2
9 50 0 7.0 ± 2.7 ND ND ND ND
10 10 11.8 ± 4.5 ND ND ND ND
11 20 12.7 ± 2.0 0.3 2.1 2.3 18.4
12 30 15.7 ± 0.5 0.6 4.0 2.8 18.2
13 100 0 5.5 ± 1.7 ND ND ND ND
14 10 10.2 ± 1.8 ND ND ND ND
15 20 11.5 ± 2.3 0.6 5.2 3.2 27.7
16 30 13.2 ± 2.1 0.7 5.7 3.8 29.0

Note: ND: not determined.

These preliminary results show the possibility of gamma irradiation for HMF oxidation to FFCA without the addition of catalyst and base. Although this system exhibited low HMF conversion, the selectivity is approximately 50% without the catalyst and base. This shows that it is possible to increase conversion by using suitable catalysts.

3.3 Stability of FDCA under gamma irradiation

Finally, the stability of FDCA under gamma irradiation in aqueous and DMSO was determined under an ambient atmosphere at 0, 10, 20, and 30 kGy. As shown in Figure 3, FDCA is relatively stable in DMSO under gamma irradiation with the conversion in the range of 5.9–10.1%. However, in an aqueous solution, FDCA almost completely degraded at an absorbed dose of 30 kGy, where no oxidative products were detected (Table 3). The report of Pal and Saravanamurugan [39] revealed some possible conversion products of FDCA, including 2,5-dihydroxymethyl tetrahydrofuran, furoic acid, and succinic acid. Table 4 compares the conversion of HMF and FDCA conversion in DMSO at 0, 10, 20, and 30 kGy. The results demonstrated that FDCA is more stable than HMF under gamma irradiation, where FDCA conversion was 5.9–10.1%, but HMF conversion was 7.1–21.8%. The high HMF conversion was obtained after gamma irradiation due to unstable molecules of HMF [40]. Furthermore, HMF can transform to other products in H2O more than in DMSO because DMSO binds HMF stronger than H2O, leading to inhibition of side reactions of HMF. DFT calculations showed that the LUMO energy of HMF was increased in DMSO, which prevented the nucleophilic attack and reduced undesirable hydration and polycondensation reactions [41]. Likewise, FDCA is also stable in DMSO under gamma irradiation.

Figure 3 The stability of FDCA in both aqueous and DMSO solutions under gamma irradiation (reaction conditions: FDCA, 0.1 mmol; solvent: 10.0 mL DI or DMSO; ambient gas: at 0, 10, 20, and 30 kGy).
Figure 3

The stability of FDCA in both aqueous and DMSO solutions under gamma irradiation (reaction conditions: FDCA, 0.1 mmol; solvent: 10.0 mL DI or DMSO; ambient gas: at 0, 10, 20, and 30 kGy).

Table 3

FDCA conversion induced by gamma irradiation in aqueous and DMSO solutions (reaction conditions: 0.1 mmol FDCA; solvent, 10.0 mL DI or DMSO; ambient gas, at 0, 10, 20, and 30 kGy)

Entry Solvent Gamma dose (kGy) FDCA conversion (%)
1 DI 0 18.0 ± 2.0
2 10 53.3 ± 1.9
3 20 85.6 ± 3.8
4 30 97.7 ± 2.3
5 DMSO 0 5.9 ± 5.6
6 10 6.5 ± 1.8
7 20 9.3 ± 4.8
8 30 10.1 ± 1.2
Table 4

HMF and FDCA conversion induced by gamma irradiation in DMSO solution (reaction conditions: 0.1 mmol HMF or FDCA; DMSO, 10.0 mL; ambient gas, at 0, 10, 20, and 30 kGy)

Entry Solvent Gamma dose (kGy) HMF conversion (%) FDCA conversion (%)
1 DMSO 0 7.1 ± 1.0 5.9 ± 5.6
2 10 19.4 ± 2.6 6.5 ± 1.8
3 20 21.5 ± 1.5 9.3 ± 4.8
4 30 21.8 ± 2.2 10.1 ± 1.2

3.4 Comparison with other reports

In this scientific evaluation, various methodologies for the conversion of hydroxymethylfurfural (HMF) to valuable products, particularly FDCA, are examined as shown in Table 5. Among these, the radiation method, a novel approach implemented in this work, demonstrates significant potential. This method shows high HMF conversion efficiency in aqueous conditions, and when applied in DMSO solvent under base- and catalyst-free conditions it exhibits favorable selectivity for oxidation products.

Table 5

Comparison of the other reported catalysts for HMF conversion and product yield

Catalyst Additives Method Reaction conditions HMF conversion (%) Reference
— — Gamma irradiation (30 kGy) Solvent: H2O 92.1 This work
Under air conditions
Time: 51 h
— — Solvent: DMSO 21.8
Under air condition
Time: 51 h
Ru/AC H2O2, Na2CO3, NaOH Microwave heating (continuous flow) Solvent: H2O 100 Zhao et al. [23]
Under air conditions
Time: 0.5 h, 80°C
Ru/AC H2O2, Na2CO3 Heating Solvent: H2O 100 Chen et al. [42]
Under air conditions
Time: 1 h, 75°C
Mn/Fe mixed oxides NaOH Hydrothermal Solvent: H2O 93 Neațu et al. [43]
Under O2 (8 bar)
Time: 24 h, 90°C
Pt/γ-Al2O3 Na2CO3 Hydrothermal Solvent: H2O 96 Sahu et al. [44]
Under O2 (1 bar)
Time: 12 h, 140°C
γ-Fe2O3@HAP-Pd(0) K2CO3 Heating Solvent: H2O 97 Zhang et al. [45]
Under O2 (1 bar)
Time: 6 h, 100°C
Ru/C NaHCO3 Hydrothermal Solvent: DMSO/H2O 100 Liu et al. [46]
Under O2 (40 bar)
Time: 12 h, 130°C
Pt/C K2CO3 Heating Solvent: DMSO/H2O (3:1) 100 Chen et al. [34]
Under O2
Time: 10 h, 100°C
Fe3O4–CoOx — Heating Solvent: DMSO 97.2 Wang et al. [47]
Oxidant: t-BuOOH
Time: 15 h, 80°C
Pt/C–O–Mg — Hydrothermal Solvent: DMSO 21.5 Han et al. [48]
Under O2 (10 bar)
Time: 12 h, 110°C

Comparatively, Chen et al.’s approach [42], utilizing a heat method at 75°C with NaHCO3 and H2O2 in H2O, achieved a 93–100% HMF conversion rate, with an enhancement upon the addition of a Ru/AC catalyst. Zhao et al.’s methodology [23] employed microwave irradiation with a Ru/AC catalyst and Na2CO3 base in water, resulting in complete HMF conversion and high FDCA yield. Other studied methods, including the use of Mn/Fe mixed oxides [43], Pt/γ-Al2O3 [44], and γ-Fe2O3@HAP-Pd(0) [45], required additional O2 pressure and base additives to achieve conversion rates of 93–97%. In DMSO solvents, catalysts like Ru/C [46], Pt/C [34], and Fe3O4-CoOx [47] reached conversion efficiencies of 97.2–100% and FDCA yields of 59.8–93%, depending on base additives or oxidants. Moreover, Pt/C–O–Mg [48] resulted in 21.5% HMF conversion under heating without base additives. In this study, the radiation method applied in DMSO solvent resulted in 21.8% HMF conversion, with selectivities of 14.9 and 43% for HMFCA and FFCA, respectively. This method demonstrated high efficiency in HMF conversion under aqueous conditions and effective selectivity for oxidative products in DMSO under base- and catalyst-free conditions. The potential of the radiation method for converting HMF into high-value products is evident, and future work may explore the use of additives to further enhance selectivity for specific oxidation products.

4 Conclusions

In this research, the impact of atmospheric gas on the conversion of HMF was found to be minimal. However, the choice of the solvent, specifically DI and DMSO, played a significant role. Using gamma irradiation at a dose of 30 kGy in an aqueous solution, we achieved an impressive 92% conversion of HMF. However, in DI, this process led to side reactions rather than the desired oxidation to FDCA. In contrast, when using DMSO as the solvent, we observed a 24.1% conversion of HMF, leading to the formation of HMFCA and FFCA, without any additional chemicals, as DMSO itself acted as a base. No oxidation products were detected in samples that were not irradiated. Interestingly, FDCA remains stable under gamma irradiation in DMSO but is highly sensitive in an aqueous solution.

The findings of this study highlight that using an aqueous solution is effective for HMF conversion, while DMSO is advantageous for yielding oxidation products. This inspires considering the use of a mixed solvent of DI/DMSO in future experiments. However, challenges remain in enhancing the product yield and selectivity, as well as in designing suitable catalysts for these processes.

Acknowledgements

This work was supported by the Development and Promotion of Science and Technology Talents Project (DPST), Thailand Institute of Nuclear Technology (public organization) and Thailand Science Research, Innovation (TSRI), National Science, Research and Innovation Fund (NSRF), IAEA Coordinated Research Project F22081, and National Research Council of Thailand (NRCT) through Grant program N41A640180.

  1. Funding information: This work was supported by the Development and Promotion of Science and Technology Talents Project (DPST), Thailand Institute of Nuclear Technology (public organization) (Thailand Science Research and Innovation (TSRI), National Science Research and Innovation Fund (NSRF), IAEA Coordinated Research Project F2208, and National Research Council of Thailand (NRCT) through Grant program N41A640180.

  2. Author contributions: T.S., T.C., and N.B. – conceptualization; T.S., T.C., P.S., S.T., W.K. and N.B. – methodology, investigation; T.S., T.C., P.S., W.S., S.L., and N.B. – formal analysis; T.C. and N.B. – writing – original draft preparation; T.S., T.C., and N.P. – writing – review and editing; T.S. and T.C. – visualization, supervision. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: All data generated or analyzed during this study are included in this published article (and its supplementary information files).

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Received: 2023-12-26
Revised: 2024-01-22
Accepted: 2024-02-07
Published Online: 2024-03-13

© 2024 the author(s), published by De Gruyter

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

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https://doi.org/10.1515/chem-2023-0206
Keywords for this article
5-hydroxymethylfurfural; gamma radiation; HMF conversion; 2,5-furandicaboxylic acid; HMF oxidation
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  2. Porous silicon nanostructures: Synthesis, characterization, and their antifungal activity
  3. Biochar from de-oiled Chlorella vulgaris and its adsorption on antibiotics
  4. Phytochemicals profiling, in vitro and in vivo antidiabetic activity, and in silico studies on Ajuga iva (L.) Schreb.: A comprehensive approach
  5. Synthesis, characterization, in silico and in vitro studies of novel glycoconjugates as potential antibacterial, antifungal, and antileishmanial agents
  6. Sonochemical synthesis of gold nanoparticles mediated by potato starch: Its performance in the treatment of esophageal cancer
  7. Computational study of ADME-Tox prediction of selected phytochemicals from Punica granatum peels
  8. Phytochemical analysis, in vitro antioxidant and antifungal activities of extracts and essential oil derived from Artemisia herba-alba Asso
  9. Two triazole-based coordination polymers: Synthesis and crystal structure characterization
  10. Phytochemical and physicochemical studies of different apple varieties grown in Morocco
  11. Synthesis of multi-template molecularly imprinted polymers (MT-MIPs) for isolating ethyl para-methoxycinnamate and ethyl cinnamate from Kaempferia galanga L., extract with methacrylic acid as functional monomer
  12. Nutraceutical potential of Mesembryanthemum forsskaolii Hochst. ex Bioss.: Insights into its nutritional composition, phytochemical contents, and antioxidant activity
  13. Evaluation of influence of Butea monosperma floral extract on inflammatory biomarkers
  14. Cannabis sativa L. essential oil: Chemical composition, anti-oxidant, anti-microbial properties, and acute toxicity: In vitro, in vivo, and in silico study
  15. The effect of gamma radiation on 5-hydroxymethylfurfural conversion in water and dimethyl sulfoxide
  16. Hollow mushroom nanomaterials for potentiometric sensing of Pb2+ ions in water via the intercalation of iodide ions into the polypyrrole matrix
  17. Determination of essential oil and chemical composition of St. John’s Wort
  18. Computational design and in vitro assay of lantadene-based novel inhibitors of NS3 protease of dengue virus
  19. Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica
  20. Microbial dynamics and dehydrogenase activity in tomato (Lycopersicon esculentum Mill.) rhizospheres: Impacts on growth and soil health across different soil types
  21. Correlation between in vitro anti-urease activity and in silico molecular modeling approach of novel imidazopyridine–oxadiazole hybrids derivatives
  22. Spatial mapping of indoor air quality in a light metro system using the geographic information system method
  23. Iron indices and hemogram in renal anemia and the improvement with Tribulus terrestris green-formulated silver nanoparticles applied on rat model
  24. Integrated track of nano-informatics coupling with the enrichment concept in developing a novel nanoparticle targeting ERK protein in Naegleria fowleri
  25. Cytotoxic and phytochemical screening of Solanum lycopersicum–Daucus carota hydro-ethanolic extract and in silico evaluation of its lycopene content as anticancer agent
  26. Protective activities of silver nanoparticles containing Panax japonicus on apoptotic, inflammatory, and oxidative alterations in isoproterenol-induced cardiotoxicity
  27. pH-based colorimetric detection of monofunctional aldehydes in liquid and gas phases
  28. Investigating the effect of resveratrol on apoptosis and regulation of gene expression of Caco-2 cells: Unravelling potential implications for colorectal cancer treatment
  29. Metformin inhibits knee osteoarthritis induced by type 2 diabetes mellitus in rats: S100A8/9 and S100A12 as players and therapeutic targets
  30. Effect of silver nanoparticles formulated by Silybum marianum on menopausal urinary incontinence in ovariectomized rats
  31. Synthesis of new analogs of N-substituted(benzoylamino)-1,2,3,6-tetrahydropyridines
  32. Response of yield and quality of Japonica rice to different gradients of moisture deficit at grain-filling stage in cold regions
  33. Preparation of an inclusion complex of nickel-based β-cyclodextrin: Characterization and accelerating the osteoarthritis articular cartilage repair
  34. Empagliflozin-loaded nanomicelles responsive to reactive oxygen species for renal ischemia/reperfusion injury protection
  35. Preparation and pharmacodynamic evaluation of sodium aescinate solid lipid nanoparticles
  36. Assessment of potentially toxic elements and health risks of agricultural soil in Southwest Riyadh, Saudi Arabia
  37. Theoretical investigation of hydrogen-rich fuel production through ammonia decomposition
  38. Biosynthesis and screening of cobalt nanoparticles using citrus species for antimicrobial activity
  39. Investigating the interplay of genetic variations, MCP-1 polymorphism, and docking with phytochemical inhibitors for combatting dengue virus pathogenicity through in silico analysis
  40. Ultrasound induced biosynthesis of silver nanoparticles embedded into chitosan polymers: Investigation of its anti-cutaneous squamous cell carcinoma effects
  41. Copper oxide nanoparticles-mediated Heliotropium bacciferum leaf extract: Antifungal activity and molecular docking assays against strawberry pathogens
  42. Sprouted wheat flour for improving physical, chemical, rheological, microbial load, and quality properties of fino bread
  43. Comparative toxicity assessment of fisetin-aided artificial intelligence-assisted drug design targeting epibulbar dermoid through phytochemicals
  44. Acute toxicity and anti-inflammatory activity of bis-thiourea derivatives
  45. Anti-diabetic activity-guided isolation of α-amylase and α-glucosidase inhibitory terpenes from Capsella bursa-pastoris Linn.
  46. GC–MS analysis of Lactobacillus plantarum YW11 metabolites and its computational analysis on familial pulmonary fibrosis hub genes
  47. Green formulation of copper nanoparticles by Pistacia khinjuk leaf aqueous extract: Introducing a novel chemotherapeutic drug for the treatment of prostate cancer
  48. Improved photocatalytic properties of WO3 nanoparticles for Malachite green dye degradation under visible light irradiation: An effect of La doping
  49. One-pot synthesis of a network of Mn2O3–MnO2–poly(m-methylaniline) composite nanorods on a polypyrrole film presents a promising and efficient optoelectronic and solar cell device
  50. Groundwater quality and health risk assessment of nitrate and fluoride in Al Qaseem area, Saudi Arabia
  51. A comparative study of the antifungal efficacy and phytochemical composition of date palm leaflet extracts
  52. Processing of alcohol pomelo beverage (Citrus grandis (L.) Osbeck) using saccharomyces yeast: Optimization, physicochemical quality, and sensory characteristics
  53. Specialized compounds of four Cameroonian spices: Isolation, characterization, and in silico evaluation as prospective SARS-CoV-2 inhibitors
  54. Identification of a novel drug target in Porphyromonas gingivalis by a computational genome analysis approach
  55. Physico-chemical properties and durability of a fly-ash-based geopolymer
  56. FMS-like tyrosine kinase 3 inhibitory potentials of some phytochemicals from anti-leukemic plants using computational chemical methodologies
  57. Wild Thymus zygis L. ssp. gracilis and Eucalyptus camaldulensis Dehnh.: Chemical composition, antioxidant and antibacterial activities of essential oils
  58. 3D-QSAR, molecular docking, ADMET, simulation dynamic, and retrosynthesis studies on new styrylquinolines derivatives against breast cancer
  59. Deciphering the influenza neuraminidase inhibitory potential of naturally occurring biflavonoids: An in silico approach
  60. Determination of heavy elements in agricultural regions, Saudi Arabia
  61. Synthesis and characterization of antioxidant-enriched Moringa oil-based edible oleogel
  62. Ameliorative effects of thistle and thyme honeys on cyclophosphamide-induced toxicity in mice
  63. Study of phytochemical compound and antipyretic activity of Chenopodium ambrosioides L. fractions
  64. Investigating the adsorption mechanism of zinc chloride-modified porous carbon for sulfadiazine removal from water
  65. Performance repair of building materials using alumina and silica composite nanomaterials with electrodynamic properties
  66. Effects of nanoparticles on the activity and resistance genes of anaerobic digestion enzymes in livestock and poultry manure containing the antibiotic tetracycline
  67. Effect of copper nanoparticles green-synthesized using Ocimum basilicum against Pseudomonas aeruginosa in mice lung infection model
  68. Cardioprotective effects of nanoparticles green formulated by Spinacia oleracea extract on isoproterenol-induced myocardial infarction in mice by the determination of PPAR-γ/NF-κB pathway
  69. Anti-OTC antibody-conjugated fluorescent magnetic/silica and fluorescent hybrid silica nanoparticles for oxytetracycline detection
  70. Curcumin conjugated zinc nanoparticles for the treatment of myocardial infarction
  71. Identification and in silico screening of natural phloroglucinols as potential PI3Kα inhibitors: A computational approach for drug discovery
  72. Exploring the phytochemical profile and antioxidant evaluation: Molecular docking and ADMET analysis of main compounds from three Solanum species in Saudi Arabia
  73. Unveiling the molecular composition and biological properties of essential oil derived from the leaves of wild Mentha aquatica L.: A comprehensive in vitro and in silico exploration
  74. Analysis of bioactive compounds present in Boerhavia elegans seeds by GC-MS
  75. Homology modeling and molecular docking study of corticotrophin-releasing hormone: An approach to treat stress-related diseases
  76. LncRNA MIR17HG alleviates heart failure via targeting MIR17HG/miR-153-3p/SIRT1 axis in in vitro model
  77. Development and validation of a stability indicating UPLC-DAD method coupled with MS-TQD for ramipril and thymoquinone in bioactive SNEDDS with in silico toxicity analysis of ramipril degradation products
  78. Biosynthesis of Ag/Cu nanocomposite mediated by Curcuma longa: Evaluation of its antibacterial properties against oral pathogens
  79. Development of AMBER-compliant transferable force field parameters for polytetrafluoroethylene
  80. Treatment of gestational diabetes by Acroptilon repens leaf aqueous extract green-formulated iron nanoparticles in rats
  81. Development and characterization of new ecological adsorbents based on cardoon wastes: Application to brilliant green adsorption
  82. A fast, sensitive, greener, and stability-indicating HPLC method for the standardization and quantitative determination of chlorhexidine acetate in commercial products
  83. Assessment of Se, As, Cd, Cr, Hg, and Pb content status in Ankang tea plantations of China
  84. Effect of transition metal chloride (ZnCl2) on low-temperature pyrolysis of high ash bituminous coal
  85. Evaluating polyphenol and ascorbic acid contents, tannin removal ability, and physical properties during hydrolysis and convective hot-air drying of cashew apple powder
  86. Development and characterization of functional low-fat frozen dairy dessert enhanced with dried lemongrass powder
  87. Scrutinizing the effect of additive and synergistic antibiotics against carbapenem-resistant Pseudomonas aeruginosa
  88. Preparation, characterization, and determination of the therapeutic effects of copper nanoparticles green-formulated by Pistacia atlantica in diabetes-induced cardiac dysfunction in rat
  89. Antioxidant and antidiabetic potentials of methoxy-substituted Schiff bases using in vitro, in vivo, and molecular simulation approaches
  90. Anti-melanoma cancer activity and chemical profile of the essential oil of Seseli yunnanense Franch
  91. Molecular docking analysis of subtilisin-like alkaline serine protease (SLASP) and laccase with natural biopolymers
  92. Overcoming methicillin resistance by methicillin-resistant Staphylococcus aureus: Computational evaluation of napthyridine and oxadiazoles compounds for potential dual inhibition of PBP-2a and FemA proteins
  93. Exploring novel antitubercular agents: Innovative design of 2,3-diaryl-quinoxalines targeting DprE1 for effective tuberculosis treatment
  94. Drimia maritima flowers as a source of biologically potent components: Optimization of bioactive compound extractions, isolation, UPLC–ESI–MS/MS, and pharmacological properties
  95. Estimating molecular properties, drug-likeness, cardiotoxic risk, liability profile, and molecular docking study to characterize binding process of key phyto-compounds against serotonin 5-HT2A receptor
  96. Fabrication of β-cyclodextrin-based microgels for enhancing solubility of Terbinafine: An in-vitro and in-vivo toxicological evaluation
  97. Phyto-mediated synthesis of ZnO nanoparticles and their sunlight-driven photocatalytic degradation of cationic and anionic dyes
  98. Monosodium glutamate induces hypothalamic–pituitary–adrenal axis hyperactivation, glucocorticoid receptors down-regulation, and systemic inflammatory response in young male rats: Impact on miR-155 and miR-218
  99. Quality control analyses of selected honey samples from Serbia based on their mineral and flavonoid profiles, and the invertase activity
  100. Eco-friendly synthesis of silver nanoparticles using Phyllanthus niruri leaf extract: Assessment of antimicrobial activity, effectiveness on tropical neglected mosquito vector control, and biocompatibility using a fibroblast cell line model
  101. Green synthesis of silver nanoparticles containing Cichorium intybus to treat the sepsis-induced DNA damage in the liver of Wistar albino rats
  102. Quality changes of durian pulp (Durio ziberhinus Murr.) in cold storage
  103. Study on recrystallization process of nitroguanidine by directly adding cold water to control temperature
  104. Determination of heavy metals and health risk assessment in drinking water in Bukayriyah City, Saudi Arabia
  105. Larvicidal properties of essential oils of three Artemisia species against the chemically insecticide-resistant Nile fever vector Culex pipiens (L.) (Diptera: Culicidae): In vitro and in silico studies
  106. Design, synthesis, characterization, and theoretical calculations, along with in silico and in vitro antimicrobial proprieties of new isoxazole-amide conjugates
  107. The impact of drying and extraction methods on total lipid, fatty acid profile, and cytotoxicity of Tenebrio molitor larvae
  108. A zinc oxide–tin oxide–nerolidol hybrid nanomaterial: Efficacy against esophageal squamous cell carcinoma
  109. Research on technological process for production of muskmelon juice (Cucumis melo L.)
  110. Physicochemical components, antioxidant activity, and predictive models for quality of soursop tea (Annona muricata L.) during heat pump drying
  111. Characterization and application of Fe1−xCoxFe2O4 nanoparticles in Direct Red 79 adsorption
  112. Torilis arvensis ethanolic extract: Phytochemical analysis, antifungal efficacy, and cytotoxicity properties
  113. Magnetite–poly-1H pyrrole dendritic nanocomposite seeded on poly-1H pyrrole: A promising photocathode for green hydrogen generation from sanitation water without using external sacrificing agent
  114. HPLC and GC–MS analyses of phytochemical compounds in Haloxylon salicornicum extract: Antibacterial and antifungal activity assessment of phytopathogens
  115. Efficient and stable to coking catalysts of ethanol steam reforming comprised of Ni + Ru loaded on MgAl2O4 + LnFe0.7Ni0.3O3 (Ln = La, Pr) nanocomposites prepared via cost-effective procedure with Pluronic P123 copolymer
  116. Nitrogen and boron co-doped carbon dots probe for selectively detecting Hg2+ in water samples and the detection mechanism
  117. Heavy metals in road dust from typical old industrial areas of Wuhan: Seasonal distribution and bioaccessibility-based health risk assessment
  118. Phytochemical profiling and bioactivity evaluation of CBD- and THC-enriched Cannabis sativa extracts: In vitro and in silico investigation of antioxidant and anti-inflammatory effects
  119. Investigating dye adsorption: The role of surface-modified montmorillonite nanoclay in kinetics, isotherms, and thermodynamics
  120. Antimicrobial activity, induction of ROS generation in HepG2 liver cancer cells, and chemical composition of Pterospermum heterophyllum
  121. Study on the performance of nanoparticle-modified PVDF membrane in delaying membrane aging
  122. Impact of cholesterol in encapsulated vitamin E acetate within cocoliposomes
  123. Review Articles
  124. Structural aspects of Pt(η3-X1N1X2)(PL) (X1,2 = O, C, or Se) and Pt(η3-N1N2X1)(PL) (X1 = C, S, or Se) derivatives
  125. Biosurfactants in biocorrosion and corrosion mitigation of metals: An overview
  126. Stimulus-responsive MOF–hydrogel composites: Classification, preparation, characterization, and their advancement in medical treatments
  127. Electrochemical dissolution of titanium under alternating current polarization to obtain its dioxide
  128. Special Issue on Recent Trends in Green Chemistry
  129. Phytochemical screening and antioxidant activity of Vitex agnus-castus L.
  130. Phytochemical study, antioxidant activity, and dermoprotective activity of Chenopodium ambrosioides (L.)
  131. Exploitation of mangliculous marine fungi, Amarenographium solium, for the green synthesis of silver nanoparticles and their activity against multiple drug-resistant bacteria
  132. Study of the phytotoxicity of margines on Pistia stratiotes L.
  133. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part III
  134. Impact of biogenic zinc oxide nanoparticles on growth, development, and antioxidant system of high protein content crop (Lablab purpureus L.) sweet
  135. Green synthesis, characterization, and application of iron and molybdenum nanoparticles and their composites for enhancing the growth of Solanum lycopersicum
  136. Green synthesis of silver nanoparticles from Olea europaea L. extracted polysaccharides, characterization, and its assessment as an antimicrobial agent against multiple pathogenic microbes
  137. Photocatalytic treatment of organic dyes using metal oxides and nanocomposites: A quantitative study
  138. Antifungal, antioxidant, and photocatalytic activities of greenly synthesized iron oxide nanoparticles
  139. Special Issue on Phytochemical and Pharmacological Scrutinization of Medicinal Plants
  140. Hepatoprotective effects of safranal on acetaminophen-induced hepatotoxicity in rats
  141. Chemical composition and biological properties of Thymus capitatus plants from Algerian high plains: A comparative and analytical study
  142. Chemical composition and bioactivities of the methanol root extracts of Saussurea costus
  143. In vivo protective effects of vitamin C against cyto-genotoxicity induced by Dysphania ambrosioides aqueous extract
  144. Insights about the deleterious impact of a carbamate pesticide on some metabolic immune and antioxidant functions and a focus on the protective ability of a Saharan shrub and its anti-edematous property
  145. A comprehensive review uncovering the anticancerous potential of genkwanin (plant-derived compound) in several human carcinomas
  146. A study to investigate the anticancer potential of carvacrol via targeting Notch signaling in breast cancer
  147. Assessment of anti-diabetic properties of Ziziphus oenopolia (L.) wild edible fruit extract: In vitro and in silico investigations through molecular docking analysis
  148. Optimization of polyphenol extraction, phenolic profile by LC-ESI-MS/MS, antioxidant, anti-enzymatic, and cytotoxic activities of Physalis acutifolia
  149. Phytochemical screening, antioxidant properties, and photo-protective activities of Salvia balansae de Noé ex Coss
  150. Antihyperglycemic, antiglycation, anti-hypercholesteremic, and toxicity evaluation with gas chromatography mass spectrometry profiling for Aloe armatissima leaves
  151. Phyto-fabrication and characterization of gold nanoparticles by using Timur (Zanthoxylum armatum DC) and their effect on wound healing
  152. Does Erodium trifolium (Cav.) Guitt exhibit medicinal properties? Response elements from phytochemical profiling, enzyme-inhibiting, and antioxidant and antimicrobial activities
  153. Integrative in silico evaluation of the antiviral potential of terpenoids and its metal complexes derived from Homalomena aromatica based on main protease of SARS-CoV-2
  154. 6-Methoxyflavone improves anxiety, depression, and memory by increasing monoamines in mice brain: HPLC analysis and in silico studies
  155. Simultaneous extraction and quantification of hydrophilic and lipophilic antioxidants in Solanum lycopersicum L. varieties marketed in Saudi Arabia
  156. Biological evaluation of CH3OH and C2H5OH of Berberis vulgaris for in vivo antileishmanial potential against Leishmania tropica in murine models
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