Tetrahydrofuran Solvent Research Articles

Advanced vat photopolymerization 3D printing of silicone rubber with high precision and superior stability

Abstract Silicone rubber (SR) is a versatile material widely used across various advanced functional applications, such as soft actuators and robots, flexible electronics, and medical devices. However, most SR molding methods rely on traditional thermal processing or direct ink writing three-dimensional (3D) printing. These methods are not conducive to manufacturing complex structures and present challenges such as time inefficiency, poor accuracy, and the necessity of multiple steps, significantly limiting SR applications. In this study, we developed an SR-based ink suitable for vat photopolymerization 3D printing using a multi-thiol monomer. This ink enables the one-step fabrication of complex architectures with high printing resolution at the micrometer scale, providing excellent mechanical strength and superior chemical stability. Specifically, the optimized 3D printing SR-20 exhibits a tensile stress of 1.96 MPa, an elongation at break of 487.9%, and an elastic modulus of 225.4 kPa. Additionally, the 3D-printed SR samples can withstand various solvents (acetone, toluene, and tetrahydrofuran) and endure temperatures ranging from −50 °C to 180 °C, demonstrating superior stability. As a demonstration of the application, we successfully fabricated a series of SR-based soft pneumatic actuators and grippers in a single step with this technology, allowing for free assembly for the first time. This ultraviolet-curable SR, with high printing resolution and exceptional stability performance, has significant potential to enhance the capabilities of 3D printing for applications in soft actuators, robotics, flexible electronics, and medical devices.

A [Zn4O(fcCO2)6] oxocarboxylate cluster: synthesis, chemical and physical properties

Abstract The reaction of the ferrocene derivative Fe(ƞ 5-C5H4CO2H)(ƞ 5-C5H4CH=CH2) (=fcCO2H) (1) with the zinc reagents [Zn(OAc)2]·xH2O (OAc = acetate; 2a, x = 0; 2b, x = 2) or ZnEt2 (3) in non-aqueous solvents toluene or tetrahydrofuran resulted in the formation of the cluster [Zn4O(fcCO2)6] (4). The structure of 4 in the solid state has been determined by single-crystal X-ray diffraction analysis. Cluster 4 crystallizes in the triclinic space group P 1 ‾ $\overline{1}$ . In 4, the cluster core is set-up by four zinc(II) ions which are forming the vertices of a tetrahedron with a μ 4-oxygen atom in its center. Six μ-fcCO2 units bridge the edges of the tetrahedron. IR spectroscopy confirms with ∆ν CO2 = 91 cm−1 (∆ν CO2 = ν CO2,asym − ν CO2,sym) the μ-bridging character of the fcCO2 entities. Cyclic voltammetry studies showed a reversible redox event at E°′ = 245 mV versus FcH/FcH+ (FcH = Fe(ƞ 5-C5H5)2) for 4 with the six fcCO2 redox events superimposed. High-resolution ESI-TOF measurements verified the identity of 4.

Modulating Interfacial Solvation via Ion Dipole Interactions for Low-Temperature and High-Voltage Lithium Batteries.

Extending the stability of ether solvents is pivotal for developing low-temperature and high-voltage lithium batteries. Herein, we elucidate the oxidation behavior of tetrahydrofuran with ternary BF4 -, PF6 - and difluoro (oxalato) borate anions and the evolution of interfacial solvation environment. Combined in situ analyses and computations illustrate that the ion dipole interactions and the subsequent formation of ether-Li+-anion complexes in electrolyte rearrange the oxidation order of solvated species, which enhances the electrochemical stability of ether solvent. Furthermore, preferential absorption of anions on the surface of high-voltage cathode favors the formation of a solvent-deficient electric double layer and an anti-oxidation cathode electrolyte interphase, inhibiting the decomposition of tetrahydrofuran. Remarkably, the formulated electrolyte based on ternary anion and tetrahydrofuran solvent endows the LiNi0.8Co0.1Mn0.1O2 cathode with considerable rate capability of 5.0 C and high capacity retention of 93.12 % after 200 cycles. At a charging voltage of 4.5 V, the Li||LiNi0.8Co0.1Mn0.1O2 cells deliver Coulombic efficiency above 99 % at both 25 and -30 °C.

Modulating Interfacial Solvation via Ion Dipole Interactions for Low‐Temperature and High‐Voltage Lithium Batteries

AbstractExtending the stability of ether solvents is pivotal for developing low‐temperature and high‐voltage lithium batteries. Herein, we elucidate the oxidation behavior of tetrahydrofuran with ternary BF4−, PF6− and difluoro (oxalato) borate anions and the evolution of interfacial solvation environment. Combined in situ analyses and computations illustrate that the ion dipole interactions and the subsequent formation of ether‐Li+‐anion complexes in electrolyte rearrange the oxidation order of solvated species, which enhances the electrochemical stability of ether solvent. Furthermore, preferential absorption of anions on the surface of high‐voltage cathode favors the formation of a solvent‐deficient electric double layer and an anti‐oxidation cathode electrolyte interphase, inhibiting the decomposition of tetrahydrofuran. Remarkably, the formulated electrolyte based on ternary anion and tetrahydrofuran solvent endows the LiNi0.8Co0.1Mn0.1O2 cathode with considerable rate capability of 5.0 C and high capacity retention of 93.12 % after 200 cycles. At a charging voltage of 4.5 V, the Li||LiNi0.8Co0.1Mn0.1O2 cells deliver Coulombic efficiency above 99 % at both 25 and −30 °C.

An integrated off-lattice kinetic Monte Carlo (KMC)-molecular dynamics (MD) framework for modeling polyvinyl chloride dehydrochlorination

In this study, a three-dimensional off-lattice kinetic Monte Carlo-Molecular Dynamics (KMC-MD) simulation framework [Comp. Mat. Sci. 229, 112421 (2023)] is used to investigate the dehydrochlorination/conjugation transformation of polyvinyl chloride (PVC) in sodium hydroxide (NaOH) with atomistic resolutions at experimental timescales (103 – 106 s). Our framework enables an examination of the competing reaction pathways and molecular-scale changes influenced by various solvents (acetone, ethylene glycol, triethylene glycol, tetrahydrofuran, and bio-derived solvents), as well as the influence of varying molecular weight distributions, NaOH concentrations, and temperatures. The algorithm simulates bond cleavage and formation during the KMC stages, whereas the MD stage is dedicated to the relaxation and thermalization of the PVC-NaOH-solvent system. The framework allows us to capture important configurational aspects (mixing, correlations, clustering, etc.) that are not accessible with a traditional microkinetic model, and it potentially allows us to perform benchmarking at experimental timescales.

Efficient and fully non-halogen solution processed Cs2AgBiBr6 perovskite solar cell

For traditional hole transport material (HTM) 2,2′,7,7′-tetrakis(N,N′-di-pmethoxyphenylamino)9,9′-spirbiuorene(Spiro-OMeTAD) used in Cs2AgBiBr6 perovskite solar cell (PSC), the strong dependence of its performance on the hygroscopic and volatility additives, together with the mismatched energy level with Cs2AgBiBr6 and gold electrodes, are considered to be the two key factors restricting the improvement of performance. Considering this, we reported a series of dopant-free D-π-D type HTMs comprising of FNP as donor unit and Cz-Mp dimer linked benzene as π-bridge, termed o-PCz, m-PCz, and p-PCz by adjusting the linkage position of π-bridge moieties. HTM p-PCz with planar rigid structure, exhibits higher hole mobility and better film morphology compared with o-PCz and m-PCz. Notably, o-PCz, m-PCz, and p-PCz all show good dissolvability in non-halogenated solvent tetrahydrofuran (THF), making it possible to fabricate Cs2AgBiBr6 PSCs with full non-halogenated solution process. As a result, the dopant-free p-PCz based Cs2AgBiBr6 PSC device achieved an efficiency of 2.44 % with enhanced ambient and thermal stability. Hence, the successful development of dopant-free p-PCz would make a great contribution for efficient and stable lead-free Cs2AgBiBr6 PSCs with full non-halogenated solution process.

Advancing optical transparency in 3D‐printed PLA parts using chemical post‐processing

AbstractFused filament fabrication (FFF) is an increasingly popular three‐dimensional (3D) printing technology known for its ability to produce complex 3D models at a low‐cost using polymer materials. Despite its advantages, the poor surface finish and high layer resolution in FFF‐printed parts have hindered its wider adoption, particularly for applications requiring high transparency. Thus, the current study investigates the transparency evaluation of chemically post‐processed 3D‐printed transparent polylactic acid (PLA) parts, focusing on enhancing optical transparency. Fused Filament Fabrication was employed to produce transparent parts made from PLA filament, which were subsequently treated at various time settings using various solvents, including tetrahydrofuran (THF), chloroform or trichloromethane (TCM), and ethyl acetate (EA). This study examines the impact of chemical post‐processing on the surface roughness, transparency, mechanical properties, and dimensional accuracy of solvent treated parts. It has been found that the THF solvent with 40 s of immersion time resulted in a maximum transmittance of 74.66% and minimum surface roughness of 1.777 μm. Based on this finding a case study was also conducted to apply the findings of the current investigation to a practical application. The findings highlight the potential of chemical‐based post‐processing techniques to improve the optical properties of 3D printed PLA, offering a promising approach for applications in optics, medical devices, and consumer goods requiring transparent components.Highlights Effect of chemical post‐processing on 3D‐printed PLA parts was investigated. Tetrahydrofuran, chloroform, and ethyl acetate were used as solvents. Surface roughness, transparency, hardness, and dimensional accuracy were analyzed. Reported a maximum transmittance of 74.66% and minimum surface roughness of 1.777 μm.

Synthesis of well-defined poly(p-alkoxystyrene) by anionic polymerization in the presence of di-n-butylmagnesium

This study demonstrates the necessity of introducing di-n-butylmagnesium (n-Bu2Mg) additives to synthesize precisely controlled polymers through anionic polymerization of p-alkoxystyrene monomers at −40 °C. Without additives, 4-tert-butoxystyrene (BSt) and 4-(1-ethoxy ethoxy) styrene (EESt) are polymerized using sec-butyllithium (s-BuLi) in tetrahydrofuran (THF) solvent, yielding a molecular weight distribution (MWD) of 1.36. However, the MWD is strictly controlled to 1.05–1.06 after adding n-Bu2Mg in more than 30 times the amount of s-BuLi, resulting in an accurately designed molecular weight. Therefore, n-Bu2Mg effectively suppresses side reactions that could occur at the polymerization temperature of −40 °C in the Schlenk reactor. Interestingly, the polymerization reaction of styrene monomer proceeds when n-Bu2Mg is mixed in THF solvent at −40 °C for an extended period, even without s-BuLi. This result suggests that, despite being a weak anionic initiator, n-Bu2Mg can initiate polymerization due to the lower electron density of the styrene double bond compared to BSt or EESt. Based on these results, a precise copolymer with a narrow molecular weight distribution can be synthesized by initiating polymerization with s-BuLi within 20 s of adding n-Bu2Mg to the mixed monomers of styrene and EESt.

Electronic effect tuned ion-dipole interactions for low-temperature electrolyte design of LiFePO4-based lithium-ion batteries

Poor low-temperature performance is one of the major challenges hindering the widespread use of lithium-ion batteries. Modulation of Li+ solvation structure to facilitate desolvation process is an important strategy in electrolyte engineering under low temperature. Herein, different electronic effect groups including electron-withdrawing groups (CH2Cl) and electron-donating groups (CH3), are introduced in the weakly solvated solvent tetrahydrofuran (THF), respectively, to compare their effects on the ion-dipole interaction in the electrolyte and thus the regulation of Li+ solvation structure. Theoretical calculations combined with characterization demonstrates that the introduction of electron-withdrawing groups CH2Cl in the solvent can reduce the electron cloud density of oxygen in the THF solvent molecule, weaken the binding energy between Li+ and the solvent, and lead to more anions participating in solvation shell of Li+ and coordinating with Li+, thus accelerating the desolvation kinetics of Li+. This electrolyte-design strategy based on electronic effect tuned ion-dipole interactions has notably increased the cycling stability of the LiFePO4||Li half-cell at –20 °C, that is, it not only increases the capacity by about 10 mAh g−1 at the rate of 0.2 C, but also maintains the capacity retention rate at 97.4 % after 100 cycles. This study reveals an important electrolyte design strategy at the molecular level.

Estimation of Electric Dipole Moment by Solvatochromism, Computational Method, and Study of the Effect of Solvents by Preferential Solvation of 6 - Methoxy-4-(4-Nitro-Phenoxy Methyl)-Chromen-2-One (6mnpm).

At room temperature, the absorption and fluorescence properties of coumarin 6-Methoxy-4-(4-nitro-phenoxy methyl)-chromen-2-one (6MNPM) are investigated in pure organic solvents and a combination of acetonitrile (ACN) and tetrahydrofuran (THF). The pure solvents' influence on spectral characteristics is examined by applying theories such as Kamlet and Catalan's multiple linear regression techniques, Reichardt's microscopic solvent polarity parameter, and the Lippert-Mataga polarity function. The significant role of solute-solvent interactions in pure solvents, particularly dielectric interaction and hydrogen bonding. However, hydrogen bonding interactions dominate the contribution of dielectric interactions. The electric dipole moments of both the ground as well as excited states had been calculated using the Solvatochromic method. The value of the excited state electric dipole moment and the redshifts of the emission spectra show that the emitting singlet state has an intramolecular charge transfer (ICT) character. From Catalan's linear regression, we found that di-polarity has a much smaller influence than polarizability. By solvation study, we conclude that Tetrahydrofuran solvent is preferred over Acetonitrile.

Solvatochromism, preferential solvation and excited state dipole moments of flufenamic acid in different solvent polarities

The influence of pure solvent and binary solvent mixtures on the optical properties of non-steroidal anti-inflammatory drug (NSAID) molecule, specifically flufenamic acid (FLA), has been studied using absorption and fluorescence spectroscopic techniques. A bathochromic shift is observed in the emission wavelength of FLA with an increase in the solvent polarity of pure solvents, attributed to the highest stability of the excited state. The spectral properties are correlated with Lippert–Mataga, solvent polarity parameter, Kamlet, and Catalan solvent polarity parameters, suggesting that both general and specific solvent effects influence the spectral properties, with general solvent effects dominating over specific solvent effects. Preferential solvation studies have been carried out in tetrahydrofuran (THF) and water solvent mixture, revealing variations in the preference for solvation of FLA as a function of the mole fraction of water. Solvatochromic data are utilized to estimate the excited state dipole moment in pure solvents using different solvatochromic methods, revealing that the excited state dipole moment of FLA is higher than its ground state counterpart. The increase in dipole moment in the excited state compared to the ground state is explained based on intramolecular charge transfer (ICT), with elaboration and discussion on the possible resonance structure corresponding to ICT, inferring the more polar nature of the excited state compared to the ground state. The effect of solute polarizability on the excited state dipole moment and change in dipole moment is also discussed.

Harvesting the tuning mechanism of strategic polychrome and white light emission in NapH dye based on excited state intermolecular proton transfer

Organic white light emitting (WLE) materials have sparked a research boom due to their promising applications in display devices, artificial lighting, and molecular sensors. However, the complex luminescence mechanism of full-spectra emitting materials has limited the development of white light materials with high stability and reproducibility. In this study, building on the full-spectra luminescent naphthimide dye (NapH) introduced by Xu et al., (Chin. Chem. Lett. 35(2024), 108348), we report the solvent-sensitive excited state proton transfer (ESPT) properties and white light emission mechanism in NapH. Our theoretical research results show that the ESPT process of NapH molecule is hindered in the low-polar solvent tetrahydrofuran (THF), so only the blue fluorescence from the Enol* is observed in the experiment. In contrast, in polar solvents such as water (H2O) and methanol (MeOH), the formation of strong intermolecular hydrogen bonds successfully initiates the ESPT process, leading to the dual fluorescence observed in experiments, with blue emission from the Enol* and red emission from the Nap anion. In essence, different solvent environments can adjust several emission colors. Furthermore, we theoretically verify that the optimal white light emission can be achieved when the mixed solvent ratio of dimethyl sulfoxide (DMSO) and dioxane (DIOX) is 5:5, which aligns well with experimental results. More importantly, we elucidate the specific WLE mechanism from multiple perspectives, including potential energy curves and electron spectra. Our work not only displays the interaction models of NapH molecule in various solvents, but also reveals the underlying luminescence mechanism, thus providing a valuable theoretical reference for the development and advancement of new white light materials.

Multigram synthesis of 2-vinylpyridine using bio-renewable 2-methyl tetrahydrofuran solvent

The present work reports the synthesis of 2-vinylpyridine in multigram synthetic approach as it has tremendous application in pharmaceutical science as well as in material science and industries. This present method emphasizes the usage of commercially available inexpensive raw materials and bio renewable solvents. Nontoxic TCCA was used as green chlorinating reagent and its corresponding bi-product obtained in the course of the reaction is biodegradable in nature. This entire three step procedure does not require any chromatographic techniques and the product is obtained in 95% yield with > 98% purity.

Synthesis and biological activity of some new podophyllotoxin bearing pyrimidine moiety

Podophyllotoxin (PPT), a naturally occurring aryltetralin-type lignan obtained from Podophyllin, an ethanolic extract of Podophyllum peltatum L. (syn. P. hexandnum Royle), exhibits marked biological activity as strong antineoplastic drugs and antiviral agents. Chemical transformations performed on PPT resulted in analogs which also display potent cytotoxic, antiviral, and immunosuppressive activities. In the present research, ten new compounds of PPTs 2a-l bearing pyrimidine moiety were synthesized by the reaction of PPT (1) with 2-methyl sulphonyl pyrimidines in the presence of tetrahydrofuran solvent and base sodium hydride. All the synthesized compounds were tested for antimicrobial activities.. KEYWORDS :4,6-Dimethoxy-2-methylsulfonylpyrimidine, Antimicrobial activity, Podophyllotoxin.

Sodium dispersion-mediated reductive dimerization of benzylic halides for symmetrical bibenzyls: Column-free applications to natural products

We report a method for the synthesis of symmetrical bibenzyls by the reductive dimerization of benzylic halides using sodium dispersion (SD). SD, a reagent consisting of sodium particles dispersed in mineral oil, has recently attracted attention as a safer but more reactive source of sodium than sodium lump. We have found that the reductive dimerization of benzylic halides proceeds within 1 h at room temperature in tetrahydrofuran (THF) solvent using SD as a reducing agent. This method is highly sustainable for the synthesis of symmetrical bibenzyls since it uses sodium, which is abundant on earth. As the SD-derived mineral oil in the crude product can be readily removed, three natural products were synthesized on a gram scale without the need for column chromatography. The utility of this reaction was also exemplified by a decagram-scale reaction using 2-methyltetrahydrofuran, known as a green alternative solvent to THF.

Exploring Cyclopentannulation as an Effective Synthetic Tool to Design Polycyclic Aromatic Hydrocarbon AIEgens for Bioimaging.

Synthesis of various polycyclic aromatic hydrocarbons (PAHs) from a palladium-catalyzed [3 + 2] cyclocondensation reaction is reported herein. The design strategy consisted of reacting the sterically hindered 1,2-bis(3,5-ditert-butylphenyl)acetylene 2 with myriad brominated anthracene and pyrene surrogates, resulting in the formation of target molecules MCP1-2 and DCP1-3, which exhibited excellent solubility in commonly used organic solvents and unveiled prominent aggregation-induced emission (AIE) characteristics in tetrahydrofuran and water solvent mixtures. Calculations using density functional theory (DFT) were utilized to validate both the contorted structures of the target molecules and their electronic conjugation featuring HOMO-LUMO band gaps (ΔE) in the range of ∼2.88 to 2.97 eV for the monocylopentannulated PAHs MCP1-2, and between ∼2.23 to 2.41 eV for the dicyclopentannulated PAHs DCP1-3. Furthermore, the biomedical features of DCP2 were investigated in cell-imaging experiments employing the RAW 264.7 macrophage cell line as a model system showing a high biocompatibility for DCP2, thus paving the way for its potential application in bioimaging. These findings underscore the significance of the target compounds as prominent AIEgens with exceptional photophysical properties and biocompatibility, therefore promoting them as valuable tools for bioimaging applications.

Fine-tuning the photophysical properties of Imidazo[1,2-a]pyridine-based dyes by the change in substituent and solvent media: DFT and TD-DFT studies

In the present work, photophysical properties of the nine excited-state intramolecular proton transfer (ESIPT) active 2-(2 -hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP)-based dyes A1-A9 (X= H, Me, F, Cl, OMe, OH, CN, NO2 and CF3) were investigated at PBE0/6-31++G(d,p) and M06-2X/6-31++G(d,p) levels of theory in the gas phase and solvent media. The structural parameters, relative energies, vibrational spectra, photophysical properties, potential energy curves, natural bond orbital (NBO) charges, hole and electron isosurfaces, electron density properties and reduced density gradient (RDG) spikes were computed. The H-bonding is strengthened at the S1 state by comparing infrared vibrational spectra, the relevant bond length and bond angle, electron density properties and RDG analysis. The results revealed that ESIPT in the A1-A7 and A9 in the gas phase is a barrier-less process, while there is an energy barrier for the A8 (X=NO2). In polar solvents, it is predicted that the ESIPT process only in A5 and A6 is a barrier-less process. The A2, A4 and A5 exhibited the greatest redshift in the keto fluorescence emission in tetrahydrofuran solvents. The significant Stokes shift observed in the S1-K emission of certain dyes makes these molecules highly appealing for various applications such as chemosensors, fluorescent probes, laser dyes and optoelectronic devices.

Organic-organic interfacial polymerization for the ultrathin polyamide organic solvent nanofiltration membranes

There is an increasing demand for advanced membranes that exhibit both high perm-selectivity and good stability in organic solvents, particularly for organic solvent nanofiltration (OSN). Traditional methods of synthesizing thin films using conventional interfacial polymerization (CIP) have been limited by the use of water-soluble monomers, which has hindered the development of high-performance membranes. To address this issue, a new method called organic-organic interfacial polymerization (OOIP) has been proposed. This method allows for the use of aromatic amines that are not water-soluble in the fabrication of ultrathin polyamide (PA) (<40 nm) thin film composite (TFC) membranes. By investigating five different organic solvents (tetrahydrofuran, acetone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide) with varying water content as the organic phase for a water-insoluble benzidine monomer, two diffusion models of monomers were identified that resulted in different membrane structures and degrees of network crosslinking. The ultrathin PA membranes produced using tetrahydrofuran-H2O and N,N-dimethylformamide-H2O, along with solvent activation, demonstrated high methanol permeances of 11.4 L m−2 h−1 bar−1 and 6.0 L m−2 h−1 bar−1, respectively, while maintaining exceptional rejections of over 99.0 % for small molecules with molecular weights greater than 452 g mol−1. The OOIP method is scalable and reproducible, making it suitable for large-scale membrane production. This innovative approach shows great potential for advancing OSN technology and providing efficient and cost-effective separation solutions for various industries.

Thiadiazole-thiazole derivatives as potent anti-tubercular agents: Synthesis, biological evaluation, and In silico docking studies

The present study focuses on research findings related to the development and assessment of thiadiazole-linked thiazole derivatives as promising anti-tubercular agents. We present the synthesis data of eleven new compounds (4a-4k) and confirm their structures using spectroscopic techniques. Subsequently, the compounds were screened for their anti-tuberculosis activities against M. tuberculosis H37Ra. The results demonstrated that compounds 3 and 4b exhibited minimum inhibitory concentration (MIC) of 3.90 μg/mL and 7.81 μg/mL, respectively. In-vitro, studies for few compounds exhibited high antioxidant activity against DPPH and OH radical scavengers along with minimal to no cytotoxicity against RBCs which is a promising result. Investigation of molecular docked conformations revealed different molecular interactions such as hydrogen bonds, halogen bonds, and interactions involving Pi electron cloud. The study sheds light on conserved interactions with residues like Met131, Val163, His90 and Gln161 from the tubercular MCAT enzyme. Interestingly, the synthetic chemistry reveals that the employment of tetra-n-butylammonium bromide (TBAB) plays a crucial role for N-butylation and it also expedites the reaction in tetrahydrofuran solvent.

The liquid-phase hydrogenation of TMCB for preparation of CBDO by fluorine-modified Ruthenium-Stannum bimetallic catalysts

A series of Ruthenium-Stannum bimetallic catalysts were prepared using the isovolumetric impregnation method and investigated for the liquid-phase hydrogenation of 2,2,4,4-tetramethyl-1,3-cyclobutanedione to its corresponding 2,2,4,4-tetramethyl-1,3-cyclobutanediol. The effects of the reaction temperature and pressure, fluorine-modified alumina, reaction solvent, and catalyst particle size on the catalytic performance were discussed. The optimum reaction conditions were obtained with a temperature of 80 ℃, a hydrogen pressure of 4.0 MPa, and a reaction solvent of tetrahydrofuran. In addition, characterization techniques, such as BET, XRD, TEM, NH3-TPD, and Py-IR, showed that the active component nanoparticles were effectively introduced into the alumina carriers, and the alumina was modified by a low concentration of NH4F solution (0.05 mol/L), which ensured that the complete conversion of 2,2,4,4-tetramethyl-1,3-cyclobutanedione was obtained while maintaining a selectivity of over 95 % for the 2,2,4,4-tetramethyl-1,3-cyclobutanediol.