To Tetrahydrofuran Research Articles

The role of hard and soft segments in the thermal and mechanical properties of non-isocyanate polyurethanes produced via polycondensation reaction

Plenty of research is being conducted on non-isocyanate polyurethanes (NIPUs) to replace harmful diisocyanates in traditional polyurethanes (PUs). In this research, the role of different types of hard and soft segments was investigated in the production of NIPUs via the polycondensation route. Hard segments comprised ethylene carbonate or propylene carbonate with hexane-1,6-diamine, while the soft segments consisted of polyethylene glycol (1000 g/mol or 400 g/mol) or polypropylene glycol (1000 g/mol) and were polymerized in different molar ratios. The NIPUs were characterized for their thermal and mechanical properties. FTIR and solvent resistance to tetrahydrofuran (THF) was used to evaluate the polycondensation reaction. Thermal analysis revealed mainly mixed hard and soft segments; the selection of the hard segment had an impact on the crystallinity of the mixed phase. Promising cohesive strength results as well as lap shear strengths were found on stainless steel and beech when the right selection of components was used. The best results were achieved when propylene carbonate was used as the hard segment, and polypropylene glycol (1000 g/mol) as the soft segment precursor in 1:30 M ratio.

Ni-Mg/Al Mixed Oxides Prepared from Layered Double Hydroxides as Catalysts for the Conversion of Furfural to Tetrahydrofurfuryl Alcohol

Ni-Mg/Al mixed oxide catalysts (Ni2Al, Ni2Mg1Al, and Ni1Mg1Al) obtained from layered double hydroxides (LDHs) were tested on the one-pot production of tetrahydrofurfuryl alcohol (TFA) from furfural (FF). Upon calcination at 400 °C and reduction at 500 °C, the LDHs gave catalysts containing small nickel crystallites (<4 nm) dispersed on mixtures of metal oxides and spinel structures. Complete conversion of FF (>99.5%) was achieved on all the catalysts after 4 h at 190 °C and 5.0 MPa of H2 using 5 wt.% FF in ethanol and a furfural-to-catalyst mass ratio of 7.44 g/g. TFA evolved from the sequential hydrogenation of FF to furfuryl alcohol (FA) to TFA. Competing reaction routes involved decarbonylation of FF to furan (FUR) followed by hydrogenation to tetrahydrofuran (THF) or hydrogenolysis to n-butane (BU) and the hydrogenation of the carbonyl group in FF to form 2-methyl furan (mFUR) and its hydrogenation to 2-methyltetrahydrofuran (mTHF). A third competing route consisted of the nucleophilic addition of FF with ethanol and with FA to form acetals (such as 2-(diethoxymethyl)furan, FDA), which were later converted to difurfuryl ether (DFE) and tetrahydrofurfuryl ethyl ether (TFEE) as final products. Hydrogen pressure favored the production of TFA and diminished the formation of acetals, while temperature reduced the capacity of the catalyst to hydrogenate the furan ring, thus reducing TFA and increasing FA and FUR. An 80% yield to TFA was achieved with the Ni2Mg1Al catalysts after 6 h at 190 °C and 50 bar H2, but a variety of coproducts were present at low concentration. Testing of the catalysts in gas-phase hydrogenation conditions at atmospheric pressure revealed a poorer performance, with FA as the main product.

Oligotriarylamine-Extended Organoboranes with Tunable Electron-Donating Strength by Changing the Number of Donor Units.

Triarylborane (Ar3B) and triarylamine (Ar3N) have been widely employed to construct electronically different donor-acceptor (D-A) systems. Herein, we describe a series of A-D-A-type luminescent organoboranes L-B2Nn (n = 1, 3, 5) that show an increased number of Ar3N units as electron donors and two terminal Ar3B as acceptors. When the Ar3N moieties were extended from one to five units, their electron-donating strength was gradually enhanced and the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) energy gaps could also be tuned, which was further reflected in the red-shifted emissions from blue (λem = 458 nm) to orange (λem = 595 nm) with a decrease in Egap(elect) from 3.19 to 2.61 eV. L-B2N5 showed a huge Stokes shift (∼14 057 cm-1) and a considerably bright emission with an enhanced solid-state quantum efficiency (ΦS = 98%) compared with the other members. L-B2N3 and L-B2N5 exhibited aggregation-induced emissions (AIEs), and an apparent solvatochromic shift was also observed in the emission spectra as the solvent was changed from hexane to tetrahydrofuran (THF) (430 → 595 nm). In addition, the donor-acceptor charge-transfer character in these organoboranes caused a thermally responsive emission over a broad range.

Application of deep eutectic solvent as novel co-solvent for oil extraction from flaxseed using sonoenergy

The extraction of oil from flaxseeds were carried out using deep eutectic solvents (DESs) and organic solvents with ultrasound assisted extraction. Enhancement of solvent extraction was investigated by adding novel co-solvents in the form of DESs to tetrahydrofuran (THF) and n-hexane. COSMO-RS, UFF and DFT computational method was used to study the solubility of organic solvents and DESs for oil extraction from flaxseed. It was noted that the solvent share the same non-polar region on the σ-profiles with the flaxseed oil model. Different organic solvents were screened and it was found that n-hexane and THF can achieve the highest oil yield. The addition of DES to THF negatively impacted oil yield. On the other hand, the addition of DES to n-hexane can slightly improve the extraction yield and significantly reduce the extraction temperature in comparison to n-hexane alone. Application of DES as novel co-solvent with other organic solvents can be translated to economic benefits through reducing the energy consumption and operational risks associated with the use of flammable solvent such as n-hexane.

Combination of few-layer graphene and commercial cosmetic film for tetrahydrofuran-sensitive smart film

A shear exfoliation of graphite in Arabic gum solution is one of the interesting non-toxic methods for production of few-layer graphene. While the utilization of Arabic-based graphene is mainly as conductive ink for inkjet or screen printing of circuit for sensing or electronic device, it is noted that there is lack of works reporting on the role of this polysaccharide class-based graphene for smart vapour-driven sensing film. In this brief report, the effect of Arabic gum/graphene presence on the cosmetic oil control film (Clean and Clear®) for bending-unbending performance of vapour-driven film was investigated. It is discovered that the film was able to complete a bending cycle within 13 s while the maximum recorded bending radius was measured at 0.48 cm after exposure to tetrahydrofuran (THF) in controlled environment condition (50%rh and 25 °C). By controlling the distance between THF source and the smart film, we further show the crawling motion of this film that resembling leech with a speed of 0.5 cm/48 s.

Influence of metal ratio on alumina-supported CuPd catalysts for the production of tetrahydrofuran from succinic acid

The present research studies the influence of metal ratio on the construction of γ-Al2O3 supported CuxPdy (x + y = 10 wt%) bimetallic catalysts for the hydrogenation of succinic acid (SA) to tetrahydrofuran (THF). Synergistic effects between Cu and Pd due to alloying formation are responsible for the enhanced activity of the bimetallic catalysts compared to the monometallic ones. The Cu-rich CuPd catalysts, particularly Cu8Pd2/γ-Al2O3 and Cu6Pd4/γ-Al2O3, have emerged as the best catalysts for the production of THF with yields of 85–90%. The key factor that distinguishes them from the rest is the presence of isolated Cu components which holds the potential for further reduction of the intermediate γ-butyrolactone while restraining the hydrogenolysis of SA to butyric acid over the Pd sites.

A green and efficient vortex-assisted liquid-phase microextraction based on supramolecular solvent for UV-VIS determination of nitrite in processed meat and chicken products.

This paper describes a simple, efficient and rapid analytical method for extraction and determination of nitrite in meat and chicken products by vortex-assisted supramolecular solvent-based liquid phase microextraction (VA-SUPRAS-LPME) prior to spectrophotometric detection. The SUPRAS was rapidly formed by the addition of a colloidal decanoic acid suspension to tetrahydrofuran (THF). The validation studies were carried out in terms of linearity, limit of detection (LOD), limit of quantitation (LOQ), matrix effects, robustness, uncertainty measurement, precision, accuracy, and certified reference material (CRM) analysis using optimized experimental conditions. The LOD, LOQ, linearity and matrix effect were 0.035ngmL-1, 0.1ngmL-1, 0.1-300ngmL-1, and 9.6% respectively, with high preconcentration factor (200). The method was successfully applied for the determination of nitrite in processed products. Moreover, the results obtained by the proposed method were compared to the standard Griess method, and showed no significant differences in term of Student's t-test.

Regulation of the Metal Center and Coordinating Anion of Mononuclear Ln(III) Complexes to Promote an Efficient Luminescence Response to Various Organic Solvents.

A series of mononuclear lanthanide complexes [Ln(L1)(NO3)3], (Ln = Dy(III), 1; Tb(III), 3; and Eu(III), 4; L1 = (N1E,N2E)-N1,N2-bis((1-methyl-1H-benzo[d]imidazol-2-yl)methylene)cyclohexane-1,2-diamine) is obtained by reacting N-methylbenzimidazole-2-carbaldehyde (L2) and 1,2-cyclohexanediamine (L3) with Ln(NO3)3·6H2O under solvothermal conditions. L1 ligand is produced via an in situ Schiff base reaction of two molecules of L2 and one molecule of L3. The metal center Ln(III) is in a N4O6 environment formed by L1 and NO3-. NaSCN is added on the basis of 1 synthesis. One SCN- replaces one of the three coordinated NO3- anions in the 1 structure, and the complex [Dy(L1)(NO3)2(SCN)]·CH3CN (2) is synthesized. The complex 1 shows excellent luminescence response to petroleum ether (PET), an organic solvent. To the best of our knowledge, this study is the first to use a complex for sensing responses to PET. When the metal center is changed, the obtained mononuclear complexes 3 and 4 show an excellent luminescence response to tetrahydrofuran (THF). Lastly, 2 obtained by changing the coordinating anion shows an excellent luminescence response to dichloromethane. Herein, for the first time, we regulate the metal center and coordinating anion of lanthanide complexes to adjust the recognition and response of these complexes to different organic solvents.

A Simple, Efficient, and Eco-Friendly Method for the Preparation of 3-Substituted-2,3-dihydroquinazolin-4(1H)-one Derivatives.

A simple, cost-effective method under environmentally benign conditions is a very important concept for the preparation of 2,3-dihydroquinazolin-4(1H)-one derivatives. The present work describes an efficient and eco-friendly protocol for the synthesis of 2-amino-N-(2-substituted-ethyl)benzamide and 3-substituted-2,3-dihydroquinazolin-4(1H)-one derivatives. The novel feature of this protocol is the use of 2-methyl tetrahydrofuran (2-MeTHF) as an eco-friendly alternative solvent to tetrahydrofuran (THF) in the first step. In the second step, methanol in the presence of potassium carbonate as a catalyst was used under conventional heating or microwave irradiation, which provided an eco-friendly method to afford the target products in excellent yields and purities. NMR (1H and 13C), elemental analysis, and LC-MS confirmed the structures of all compounds. X-ray crystallography further confirmed the structure of the intermediate 2-amino-N-(2-substituted-ethyl)benzamide 3a. The molecular structure of 3a was monoclinic crystal, with P21/c, a = 13.6879 (11) Å, b = 10.2118 (9) Å, c = 9.7884 (9) Å, β = 105.068 (7)°, V = 1321.2 (2) Å3, and Z = 4.

Cyclodehydration of 1,4-butanediol over Zr-Al Catalysts: Effect of Reaction Medium.

The conversion of 1,4-butanediol (BDO) to tetrahydrofuran (THF) in aqueous phase is desirable because BDO production technology is shifting to bio-based aqueous fermentation routes. In this study, liquid-phase cyclodehydration of BDO to THF was studied in two reaction media (pure BDO and aqueous BDO feeds) at 200–240 °C using ZrO2-Al2O3 (ZA) mixed oxides, which were made with a co-precipitation method and were characterized with XRD, BET, SEM/EDX, pyridine and n-butylamine adsorptions. The maximum acidity and the largest surface area occurred at Zr/Al atomic ratios of 1/1 (ZA11) and 1/3 (ZA13), respectively. The reaction exhibited pseudo-first-order; aqueous BDO feed had much greater rate constant than pure BDO feed, ascribed to the acidic properties of adsorbed water molecules (coordinated to surface metal cations) for the former case. For pure BDO feed, linear relation was observed between rate constant and catalyst acidity, and ZA11 reached a THF yield of 90.1% at 240 °C. With aqueous BDO feed, rate constant increased linearly with increasing surface area and ZA13 reached a THF yield of 97.1% at 220 °C. The change of optimum catalyst composition with reaction medium suggests that active sites for catalyzing BDO cyclodehydration changed with the reaction environment.

An excellent colorimetric and "turn off" fluorescent probe for tetrahydrofuran based on a luminescent macrocyclic samarium(iii) complex.

In this paper we report a novel probe based on a luminescent 23-membered [1 + 1] Schiff-base macrocyclic mononuclear Sm(iii) complex Sm-2e, originating from the dialdehyde H2Qe and 1,2-bis(2-aminoethoxy)ethane precursors, which is synthesized by the Sm(iii) ion template method. X-ray structural analyses confirm that each ten-coordinate Sm(iii) center with the coordination geometry of a distorted bicapped square antiprism is fully encapsulated by a flexible macrocyclic ligand H2L2e to form a "lasso-type" architecture, and this architecture could enable efficient energy transfer in various solvents confirmed by long lifetimes (33.5-65.2 μs) and high quantum yields (0.23-0.76%) of the Sm(iii) ion. Simultaneously, complex Sm-2e could serve as a probe for sensing organic solvents. Particularly, this complex probe Sm-2e exhibits a highly selective, rapid and sensitive response to tetrahydrofuran (THF), which is easily distinguished by a large absorption shift, even visible to the naked eye, and complete fluorescence quenching. Moreover, the limit of detection for THF is about 0.20% determined by titration experiments, and good selectivity for THF could still be realized in mixture solvents. Consequently, this colorimetric and "turn off" fluorescent probe Sm-2e could be a valuable candidate as a sensor material for sensing THF which has been rarely reported.

Efficient Conversion of Cellulose to 5‐Hydroxymethylfurfural in NaHSO4/ZrO2/H2O‐THF Biphasic System

Abstract5‐hydroxymethylfurfural (HMF) is an important bio‐based platform chemical for liquid fuel production. Herein, efficient conversion of cellulose to HMF in NaHSO4/ZrO2/H2O‐THF biphasic system was investigated with a high HMF yield up to 86.5%. In the co‐catalytic system, H+ ions given from NaHSO4 was promotive to all steps of the cellulose‐to‐HMF conversion; abundant alkaline sites of ZrO2 was particularly favorable to the glucose‐to‐fructose isomerization. The accelerated conversion of glucose as well as the fast extraction of HMF from aqueous phase to tetrahydrofuran (THF) phase, favored the inhibition of humins which was generated from condensation between glucose and HMF. Only a trace amount of humins over ZrO2 was detected after reaction, which guaranteed the reusability of ZrO2 in six running experiments without any post‐treatment. The good reusability of ZrO2, the low ‐cost of NaHSO4, and the biomass‐derived THF were advantageous for potential industrial application.

Feedback System Control Optimized Electrospinning for Fabrication of an Excellent Superhydrophobic Surface.

Superhydrophobic surface, as a promising micro/nano material, has tremendous applications in biological and artificial investigations. The electrohydrodynamics (EHD) technique is a versatile and effective method for fabricating micro- to nanoscale fibers and particles from a variety of materials. A combination of critical parameters, such as mass fraction, ratio of N, N-Dimethylformamide (DMF) to Tetrahydrofuran (THF), inner diameter of needle, feed rate, receiving distance, applied voltage as well as temperature, during electrospinning process, to determine the morphology of the electrospun membranes, which in turn determines the superhydrophobic property of the membrane. In this study, we applied a recently developed feedback system control (FSC) scheme for rapid identification of the optimal combination of these controllable parameters to fabricate superhydrophobic surface by one-step electrospinning method without any further modification. Within five rounds of experiments by testing totally forty-six data points, FSC scheme successfully identified an optimal parameter combination that generated electrospun membranes with a static water contact angle of 160 degrees or larger. Scanning electron microscope (SEM) imaging indicates that the FSC optimized surface attains unique morphology. The optimized setup introduced here therefore serves as a one-step, straightforward, and economic approach to fabricate superhydrophobic surface with electrospinning approach.

PS-b-PMMA/PLA blends for nanoporous templates with hierarchical and tunable pore size

Blends of poly(styrene)-block-poly(methyl methacrylate) (PS-b-PMMA) and poly(lactide) (PLA) were deposited in the form of thin films on the surface of modified silicon wafers and exposed to tetrahydrofuran (THF) vapor annealing. It was shown that in specific experimental conditions, a core-shell morphology consisting in cylinders with a PMMA shell and a PLA core, within a continuous matrix of PS, was formed. In this case, PLA naturally segregated in the core of the PMMA cylinders, minimizing the PS/PLA interaction, which constitutes the most incompatible pair (the interaction strength between the various components was confirmed in thin films of the corresponding polymer blends). Compared to other block copolymer/homopolymer blends described in the literature, this system exhibits unexpected high increase of the characteristic lengths of the system (center-to-center distance and diameter). This was attributed to a partial solubilization of the PLA in the PMMA corona (the two polymers are highly compatible), inducing an enhanced level of PS and PLA stretching caused by the strong repulsion between these two polymers. The selective extraction of the PLA yielded to porous domains with small dimensions (6±2.5nm), reaching the performances that are currently attained in highly incompatible block polymers with low molecular weight. Further PMMA removal revealed a second porosity level, with higher pores diameter and center-to-center distance compared to the neat PS-b-PMMA system. This work highlights how PS-b-PMMA, that currently represents one of the industrial standards nanoporous template precursors, can be modified in an easy and costless approach using PLA homopolymer addition.

Gyrification-Inspired Highly Convoluted Graphene Oxide Patterns for Ultralarge Deforming Actuators

Gyrification in the human brain is driven by the compressive stress induced by the tangential expansion of the cortical layer, while similar topographies can also be induced by the tangential shrinkage of the spherical substrate. Herein we introduce a simple three-dimensional (3D) shrinking method to generate the cortex-like patterns using two-dimensional (2D) graphene oxide (GO) as the building blocks. By rotation-dip-coating a GO film on an air-charged latex balloon and then releasing the air slowly, a highly folded hydrophobic GO surface can be induced. Wrinkling-to-folding transition was observed and the folding state can be easily regulated by varying the prestrain of the substrate and the thickness of the GO film. Driven by the residue stresses stored in the system, sheet-to-tube actuating occurs rapidly once the bilayer system is cut into slices. In response to some organic solvents, however, the square bilayer actuator exhibits excellent reversible, bidirectional, large-deformational curling properties on wetting and drying. An ultralarge curvature of 2.75 mm-1 was observed within 18 s from the original negative bending to the final positive bending in response to tetrahydrofuran (THF). In addition to a mechanical hand, a swimming worm, a smart package, a bionic mimosa, and two bionic flowers, a crude oil collector has been designed and demonstrated, aided by the superhydrophobic and superoleophilic modified GO surface and the solvent-responsive bilayer system.

Nano CuO/ZSM-5 zeolite as a green and efficient catalyst for dehydration of 1,4-butanediol to tetrahydrofuran

Nano CuO/ZSM-5 zeolite was prepared and used as a catalyst for dehydration of 1,4-butanediol (BDO) to tetrahydrofuran (THF) in liquid-phase. It was found that the 4.6 wt% CuO/ZSM-5 displayed good catalytic performance, and nearly 100% of BDO conversion and more than 99% of THF selectivity could be achieved by a rotary evaporator reactor at 170 °C under the atmospheric pressure. With such mild reaction conditions, 2400 g BDO could be converted to THF over 1 g catalyst under semi-continuous operation. Characterizations with X-ray diffraction (XRD), temperature-programmed reduction (TPR), NH3-temperature programmed desorption (TPD), X-ray photoelectron spectroscopy (XPS), transmission electron microscope (TEM) and Brunauer-Emmett-Teller (BET) over fresh and used 4.6 wt% CuO/ZSM-5 were conducted. Based on the results of the characterization and catalytic performance of 4.6 wt% CuO/ZSM-5, it can be conjectured that the formed 1–3 nm CuO nanoparticles, suitable acidity of the catalyst due to the synergic interaction of CuO and ZSM-5 support promoted the dehydration of BDO to THF.

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

The ferrocenyl‐containing 3,5‐di‐tert‐butylcatechol Fc‐L‐CatH2 (2) was synthesized by the condensation of the precursor 6‐(hydrazonomethyl)‐3,5‐di‐tert‐butylcatechol 6‐(H2N–N=CH)CatH2 (1) with ferrocenecarboxaldehyde (L = –CH=N–N=CH–, Cat = 3,5‐di‐tert‐butylcatecholate, Fc = ferrocene). The exchange reaction between catechol 2 and Ph3SbBr2 in the presence of a base (Et3N) in toluene leads to the formation of the triphenylantimony(V) catecholate (Fc‐L‐Cat)SbPh3 (3) as the main product and the ionic bromotriphenylantimony(V) catecholate (Fc‐LH‐Cat)SbPh3Br (4) containing a hydraziniumylidene cation (LH = –CH=NH+–N=CH–) as the byproduct. The change of toluene to tetrahydrofuran (THF) results in the formation of 4 as the main product in nearly quantitative yield. The exchange reactions of catechol 2 with Ph2SnCl2 and SnCl4 give anionic catecholate complexes bridged with hydraziniumylidene cations even in the presence of excess base. Complexes (Fc‐LH‐Cat)SnPh2Cl (5), (Fc‐LH‐Cat)2SnPh2 (6), and (Fc‐LH‐Cat)2SnCl2 (7) were synthesized. The compounds obtained were characterized by IR spectroscopy, 1H and 13C NMR spectroscopy, elemental analysis, and cyclic voltammetry. The molecular structures of crystals of 5–7 were determined by X‐ray diffraction analysis. The formation of catecholates 4–7 with hydraziniumylidene cations is caused by intramolecular hydrogen bonding between the hydroxy and imine groups, which leads to proton transfer from the oxygen atom to the nitrogen atom of the hydrazine linker.

Lithium Enolates Derived from Pyroglutaminol: Mechanism and Stereoselectivity of an Azaaldol Addition.

A lithium enolate derived from an acetonide-protected pyroglutaminol undergoes a highly selective azaaldol addition with (E)-N-phenyl-1-[2-(trifluoromethyl)phenyl]methanimine. The selectivity is sensitive to tetrahydrofuran (THF) concentration, temperature, and the presence of excess lithium diisopropylamide base. Rate studies show that the observable tetrasolvated dimeric enolate undergoes reversible deaggregation, with the reaction proceeding via a disolvated-monomer-based transition structure. Limited stereochemical erosion stems from the intervention of a trisolvated-monomer-based pathway, which is suppressed at low THF concentrations and elevated temperature. Endofacial selectivity observed with excess lithium diisopropylamide (LDA) is traced to an intermediate dianion formed by subsequent lithiation of the monomeric azaaldol adduct, which is characterized as both a dilithio form and a trilithio dianion-LDA mixed aggregate.

Trimethylsilyl Chloride-Modified Li Anode for Enhanced Performance of Li-S Cells.

A facile and effective method to modify Li anode for Li-S cells by exposing Li foils to tetrahydrofuran (THF) solvent, oxygen atmosphere and trimethylsilyl chloride ((CH3)3SiCl) liquid in sequence is proposed. The results of SEM and XPS show the formation of a homogeneous and dense film with a thickness of 84 nm on Li metal surface. AC impedance and polarization test results show the improved interfacial stability. The interfacial resistances as well as polarization potential difference have obviously decreased as compared with that of a pristine Li anode. CV and charge-discharge test results demonstrate that more reversible discharge capacity and higher Coulombic efficiency can be achieved. Specific capacity of 760 mAh g(-1) and an average Coulombic efficiency of 98% are retained after 100 cycles at 0.5C without LiNO3 additive. Additionally, the Li-S cell with a modified Li anode displays a greatly improved rate performance with ∼425 mAh g(-1) at 5C, making it more attractive and competitive in the applications of high-power supply.

The inhibition performance in relation to the adsorption of a polymeric kinetic inhibitor towards THF hydrates in the presence of methanol, ethanol and monoethylene glycol

This report details an investigation of the adsorbability and inhibition performance of a kinetic inhibitor (KHI), namely poly(ethyleneoxide-co-vinylcaprolactam) (PEO-co-VCap-1), in relation to tetrahydrofuran (THF) hydrates in the presence of low concentrations of methanol, ethanol and monoethylene glycol during the hydrates formation process. Results from the quantitative examinations indicate that the presence of these molecules increases KHI adsorption onto the hydrate crystals and reduces the cage occupancy of THF. Improved inhibition performance of KHI by the added chemicals upon THF hydrates formation was well demonstrated in all cases. The inhibition performance was strongly correlated to the KHI adsorbability, irrespective of the type and/or concentration of the chemical additives.