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Cas Database

109-99-9

109-99-9

Identification

  • Product Name:Tetrahydrofuran

  • CAS Number: 109-99-9

  • EINECS:203-726-8

  • Molecular Weight:72.1069

  • Molecular Formula: C4H8O

  • HS Code:2932.11

  • Mol File:109-99-9.mol

Synonyms:NCI-C60560;Polytetrahydrofuran;Oxacyclopentane;Tetramethylene oxide;Hydrofuran;Tetrahydrofuraan;Tetraidrofurano;Butane .alpha.,.delta.-oxide;Oxolane;Tetrahydrfuran;Furan, tetrahydro-;Tetrahydrofuranne;THF;Cyclotetramethylene oxide;Furan,tetrahydro-;Furanidine;Diethylene oxide;Butane, 1,4-epoxy-;Tetra hydro furan;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi,FlammableF

  • Hazard Codes:Xi,F,Xn

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH319 Causes serious eye irritation H335 May cause respiratory irritation H351 Suspected of causing cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Product Description:Tetrahydrofuran (stabilized with BHT) [Solvent for Determination of Vinyl Chloride Monomer] >99.0%(GC)
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Relevant articles and documentsAll total 270 Articles be found

Anodization of bismuth doped TiO2 nanotubes composite for photocatalytic degradation of phenol in visible light

Ali, Imran,Kim, Seu-Run,Kim, Sung-Pil,Kim, Jong-Oh

, p. 31 - 37 (2017)

Bismuth doped TiO2 photocatalyst was synthesized in a one-step electrochemical anodization method. Bismuth nitrate Bi(NO3)3 was used as a bismuth source. The obtained samples were characterized by FE-SEM, XRD, EDX and XPS. The optimum synthesis conditions for bismuth doping were 1.0 M bismuth nitrate in an ethylene glycol electrolyte with anodization at 40 V for 2 h. Compared with undoped TiO2 nanotubes, bismuth doped TiO2 photocatalyst showed a higher photocatalytic activity by a factor of 4.0 for phenol degradation under visible light irradiation. The optimum phenol degradation using a photoelectrocatalytic method was observed at a 0.5 V external bias, and this degradation rate was 5.2 times faster than that observed for undoped TiO2 nanotubes. The doped bismuth TiO2 nanotubes are favorable for the separation of photo-induced electrons and holes, reducing the recombination of charges, and promoting the formation of hydroxyl radicals and superoxides that degrade phenol.

Mechanistic Study on Deoxydehydration and Hydrogenation of Methyl Glycosides to Dideoxy Sugars over a ReO x-Pd/CeO2Catalyst

Cao, Ji,Hasegawa, Jun-Ya,Hosaka, Ryu,Nakagawa, Yoshinao,Nakayama, Akira,Tamura, Masazumi,Tomishige, Keiichi

, p. 12040 - 12051 (2020)

We found that nonprotected methyl glycosides with cis-vicinal OH groups could be converted to the corresponding methyl dideoxy glycosides by deoxydehydration and consecutive hydrogenation (DODH + HG) over a ReOx-Pd/CeO2 catalyst with gaseous H2. In the study, the reactivity of the methyl glycosides in DODH was clearly lower than that of simple cyclic vicinal diols, such as cis-1,2-cyclohexanediol and cis-1,2-cyclopentanediol, and the reactivity of the methyl glycosides was also different. Herein, we investigated the reactivity difference based on kinetic studies and density-functional theory (DFT) calculations. The kinetic studies suggest that the reactivity difference between the methyl glycosides and the simple diols is derived from the OH group of methyl glycosides except the cis-vicinal diols, and that the reactivity difference among the methyl glycosides will be associated with the configuration of the substituents adjacent to the cis-vicinal diols, while the reaction mechanism of DODH is suggested to be basically similar judging from almost the same reaction orders with respect to the substrate concentration and H2 pressure in all substrates. The adsorption and transition states of methyl α -l- rhamnopyranoside and methyl α-l-fucopyranoside, which have a large reactivity difference (methyl α-l-rhamnopyranoside? methyl α-l-fucopyranoside), were estimated by DFT calculations with ReOx/CeO2 as the active site of the ReOx-Pd/CeO2 catalyst, showing that the main difference is the activation energy in DODH of these substrates (65 kJ mol-1 for methyl α-l-rhamnopyranoside and 77 kJ mol-1 for methyl α-l-fucopyranoside), which was also supported by the results of Arrhenius plots (63 and 73 kJ mol-1 for methyl α-l-rhamnopyranoside and methyl α-l-fucopyranoside, respectively). The activation energy was influenced by the torsional angle of the substituents adjacent to the cis-vicinal OH groups, which is derived from the interaction of the OH group adjacent to the cis-vicinal OH groups and the surface hydroxy groups on CeO2.

-

Klute,Walters

, p. 506,507 (1946)

-

Structure, activity, and selectivity of bimetallic Pd-Fe/SiO2 and Pd-Fe/Γ-Al2O3 catalysts for the conversion of furfural

Pino, Natalia,Sitthisa, Surapas,Tan, Qiaohua,Souza, Talita,López, Diana,Resasco, Daniel E.

, p. 30 - 40 (2017)

The conversion of furfural has been investigated in vapor and liquid phases over a series of supported monometallic Pd and bimetallic Pd-Fe catalysts. Over the monometallic Pd/SiO2 catalyst, the decarbonylation reaction dominates, yielding furan as the main product. By contrast, over the bimetallic Pd-Fe/SiO2 catalyst a high yield of 2-methylfuran is obtained with much lower yield to furan. Interestingly, changing the catalyst support affects the product distribution. For instance, using γ-Al2O3 instead of SiO2 as support of the bimetallic catalyst changed the dominant product from 2-methylfuran to furan. That is, Pd-Fe/γ-Al2O3 behaves more like monometallic Pd/SiO2 than bimetallic Pd-Fe/SiO2. A detailed characterization of the catalysts via XPS, XRD, and TEM indicated that a Pd-Fe alloy is formed on the SiO2 support but not on the γ-Al2O3 support. Theoretical density functional theory calculations suggest that on the Pd-Fe alloy binding of the furan ring to the surface is weakened compared to on pure Pd. This weakening disfavors the ring hydrogenation and decarbonylation paths, while the oxophilic nature of Fe atoms enhances the interaction of the C[dbnd]O and the OH groups with the metal surface, which favors the C[dbnd]O hydrogenation and C–O bond cleavage paths. The presence of the solvent has a less pronounced effect, but clearly has a stronger inhibition on C–C bond cleavage (decarbonylation to furan) than on C–O bond cleavage (hydrogenolysis to methylfuran).

Insights into the Oxidation State and Location of Rhenium in Re-Pd/TiO2 Catalysts for Aqueous-Phase Selective Hydrogenation of Succinic Acid to 1,4-Butanediol as a Function of Palladium and Rhenium Deposition Methods

Ly, Bao Khanh,Tapin, Beno?t,Aouine, Mimoun,Delichere, Pierre,Epron, Florence,Pinel, Catherine,Especel, Catherine,Besson, Michèle

, p. 2161 - 2178 (2015)

ReOx-Pd/TiO2 catalysts prepared from different 2 wt %Pd/TiO2 catalysts using two protocols for the deposition of the Re promoter (successive impregnation and catalytic reduction) were characterized by different techniques to better understand the nature of the active and selective sites implied in the aqueous-phase hydrogenation of succinic acid to 1,4-butanediol. Regardless of the support and Re introduction method, it was established that varying amounts of Pd and Re were in very close proximity without electronic interaction in the reduced catalysts. A high fraction of Re always remained partially oxidized to generate a bimetallic catalyst that can provide the necessary bifunctional sites to enable the selective hydrogenolysis of the intermediate γ-butyrolactone to 1,4-butanediol. Depending on the method of promotion, the ReOx species that interact with Pd were deposited as clusters with different spatial Re-Re interactions.

Hydrodeoxygenation of vicinal OH groups over heterogeneous rhenium catalyst promoted by palladium and ceria support

Ota, Nobuhiko,Tamura, Masazumi,Nakagawa, Yoshinao,Okumura, Kazu,Tomishige, Keiichi

, p. 1897 - 1900 (2015)

Heterogeneous ReOx-Pd/CeO2 catalyst showed excellent performance for simultaneous hydrodeoxygenation of vicinal OH groups. High yield (> 99%), turnover frequency (300 h-1), and turnover number (10 000) are achieved in the reaction of 1,4-anhydroerythritol to tetrahydrofuran. This catalyst can be applied to sugar alcohols, and mono-alcohols and diols are obtained in high yields (≥ 85%) from substrates with even and odd numbers of OH groups, respectively. The high catalytic performance of ReOx-Pd/CeO2 can be assigned to rhenium species with + 4 or + 5 valence state, and the formation of this species is promoted by H2/Pd and the ceria support.

Hydrogenation of succinic acid to tetrahydrofuran (THF) over ruthenium-carbon composite (Ru-C) catalyst

Hong, Ung Gi,Kim, Jeong Kwon,Lee, Joongwon,Lee, Jong Kwon,Song, Ji Hwan,Yi, Jongheop,Song, In Kyu

, p. 466 - 471 (2014)

Ruthenium-carbon composite (Ru-XC) catalysts prepared by a single-step surfactant-templating method were pre-graphitized at different temperature (X = 200, 250, 300, 350, and 400 C), and they were applied to the liquid-phase hydrogenation of succinic acid to tetrahydrofuran (THF). The effect of pre-graphitization temperature on the catalytic performance of Ru-XC catalysts (X = 200, 250, 300, 350, and 400 C) was investigated. It was observed that Ru-XC composite catalysts showed different textural properties depending on pre-graphitization temperature. In the liquid-phase hydrogenation of succinic acid to tetrahydrofuran (THF), conversion of succinic acid and yield for THF showed volcano-shaped trends with respect to pre-graphitization temperature. In other words, an optimal pre-graphitization temperature was required to achieve maximum catalytic performance of Ru-XC catalysts. Yield for THF in the hydrogenation of succinic acid increased with decreasing ruthenium particle size of Ru-XC catalysts. Among the catalysts tested, Ru-300C, which had the smallest ruthenium particle size, showed the highest yield for THF.

Photocatalytic hydrogenation of furan to tetrahydrofuran in alcoholic suspensions of metal-loaded titanium(IV) oxide without addition of hydrogen gas

Nakanishi, Kousuke,Tanaka, Atsuhiro,Hashimoto, Keiji,Kominami, Hiroshi

, p. 20206 - 20212 (2017)

The use of metal co-catalysts broadens the application of photocatalytic reduction without the use of dihydrogen (H2) gas. We examined photocatalytic hydrogenation of furan, a representative heterocyclic compound and a compound derived from biomass, in alcoholic suspensions of metal-loaded titanium(iv) oxide (TiO2) under a H2-free condition and we found that furan was almost quantitatively hydrogenated to tetrahydrofuran with a high apparent quantum efficiency of 37% at 360 nm when palladium was used as a co-catalyst. Effects of different metal co-catalysts, different amounts of the co-catalyst, the type of TiO2, the type of alcohol, light wavelength and reusability for furan hydrogenation were investigated. Based on the results, the functions of TiO2 and the co-catalyst and the reaction process are discussed.

Importance of Zeolite Wettability for Selective Hydrogenation of Furfural over Pd@Zeolite Catalysts

Wang, Chengtao,Liu, Zhiqiang,Wang, Liang,Dong, Xue,Zhang, Jian,Wang, Guoxiong,Han, Shichao,Meng, Xiangju,Zheng, Anmin,Xiao, Feng-Shou

, p. 474 - 481 (2018)

The metal-catalyzed selective hydrogenation of biomass-derived molecules is in great demand but is challenging due to the complex reaction pathways. Herein, we report a persuasive example for achieving selective hydrogenation of furfural over Pd catalysts by controllable sorption of molecules in zeolite micropores. The key to this success is fixation of Pd nanoparticles inside of silicalite-1 zeolite with controllable wettability (Pd@S-1-OH) by functionalizing silanol groups into the zeolite framework. In the hydrogenation of furfural as a model reaction, the Pd@S-1-OH catalyst with appropriate hydrophilicity exhibits extraordinary selectivity for the formation of furan, giving furan selectivity as high as >99.9% with a complete conversion of furfural, outperforming the conventional Pd nanoparticles supported on zeolite crystals (Pd/S-1) and S-1 zeolite fixed Pd catalysts without an artificially functionalized silanol group (Pd@S-1). The extraordinary performance of Pd@S-1-OH is reasonably attributed to the controllable diffusion of molecules within the hydrophilic zeolite micropores, which favors the adsorption of furfural and a series of byproducts but promotes the desorption of furan. Very importantly, Pd@S-1-OH is stable and gives the furan productivity of ~583.3 g gPd-1 day-1 in a continuous test.

The selectively regulated vapour phase dehydrogenation of 1,4-butanediol to γ-butyrolactone employing a copper-based ceria catalyst

Bhanushali, Jayesh T.,Prasad, Divya,Patil, Komal N.,Babu, Gurram Venkata Ramesh,Kainthla, Itika,Rao, Kamaraju Seetha Rama,Jadhav, Arvind H.,Nagaraja, Bhari Mallanna

, p. 11968 - 11983 (2019)

The growing pursuit of the viable application of γ-butyrolactone (GBL) as an industrially important product offers the possibility to use 1,4-butanediol (1,4-BDO) as a potential reactant. In this regard, different proportions of copper-based ceria catalysts (5, 10, 15, and 20CC) were synthesized using a wet impregnation method and their catalytic activities were tested for the vapour phase dehydrogenation of 1,4-BDO to GBL at temperatures from 240-300 °C. The synthesized copper-based ceria catalysts (5CC, 10CC, 15CC, and 20CC) were characterized using various analytical tools and the consequent results revealed that the activities of the CC catalysts were influenced by the physicochemical properties of the materials. In order to determine the influence of various supports on the catalytic activity, the addition of 10 wt% copper (Cu) to TiO2, Al2O3, ZnO, ZSM-5, and SBA-15 supports was carried out, and the respective influence on the catalytic activity was also experimentally established. The most outstanding catalytic activity was seen for the 10 wt% copper-based ceria catalyst, with a high conversion of 93% and selectivity of 98% at 240 °C. Factors like a high surface area, and better dispersion and basicity of active sites had a marked impact on the catalytic activity. Mechanistic analysis suggested that 1,4-BDO undergoes dehydrogenation over the copper surface to give 4-hydroxybutanal, followed by hemiacetylation and subsequent dehydrogenation to give GBL as the selective product. In terms of the stability of the catalysts, the 10 wt% copper-based ceria catalyst maintained a stable GBL selectivity of 98% for up to 7 h on-stream.

In situ DRIFTS for the mechanistic studies of 1,4-butanediol dehydration over Yb/Zr catalysts

Mi, Rongli,Hu, Zhun,Yang, Bolun

, p. 138 - 151 (2019)

To study the effect of acid-base properties of catalysts on 1,4-butanediol (BDO) dehydration to 3-buten-1-ol (BTO), Yb/Zr catalysts with different Yb content were synthesized by a wet impregnation method. The texture property, crystalline form and surface

Catalytic Dehydration of 1,4-Butanediol over Mg?Yb Binary Oxides and the Mechanism Study

Hu, Zhun,Mi, Rongli,Yang, Bolun,Yi, Chunhai

, (2020)

In this study, Mg?Yb binary oxides were synthesized using different MgO concentrations and investigated for the catalytic dehydration of 1,4-butanediol (BDO) into 3-buten-1-ol (BTO). The physicochemical properties of the catalysts were characterized by N

The Elimination Kinetics of Methoxyalkyl Chlorides in the Gas Phase. Evidence for Neighboring Group Participation

Chuchani, Gabriel,Martin, Ignacio

, p. 431 - 433 (1986)

The rates of elimination of 3-methoxy-1-chloropropane and 4-methoxy-1-chlorobutane have been determined in a seasoned, static reaction vessel over the temperature range of 410-490 deg C and the pressure range of 56-181 torr.The reactions are homogeneous and unimolecular, follow a first-order rate low, and are invariant to the presence of a twofold or greater excess of the radical chain inhibitor toluene.The overall rate coefficients are given by the following Arrhenius equations: for 3-methoxy-1-chloropropane, logk1(s-1)=(12.92+/-0.48)-(226.0+/-6.8) kJ mol-1(2.303RT)-1; for 4-methoxy-1-chlorobutane, logk1(s-1)=(12. 9+/-0.26)-(218.1+/-3.5) kJ mol-1(2.303RT)-1.The CH3O group in 4-methoxy-1-chlorobutane has been found to assist anchimerically the elimination reaction, where dehydrochlorination and tetrahydrofuran formation arise from an intimate ion pair type of mechanism.The partial rates for these parallel eliminations have been determined and reported.Participation of the CH3O in 3-methoxy-1-chloropropane is barely detected.The present results give further evidence of intimate ion pair mechanism through neighboring group perticipation in the gas-phase elimination of certain types of organic molecules.

-

Goodings,Wilson

, p. 4798 (1951)

-

-

Gillis

, p. 651,653 (1960)

-

Palladium–Ruthenium Catalyst for Selective Hydrogenation of Furfural to Cyclopentanol

Mironenko,Belskaya,Lavrenov,Likholobov

, p. 339 - 346 (2018)

Bimetallic Pd–Ru/C catalyst was shown to be much more active in the aqueous-phase hydrogenation of furfural (473 K, 8 MPa) in comparison with both Pd/C and Ru/C catalysts. The enhanced hydrogenation activity manifested itself as an increased yield of cyclopentanol (77%) at a complete conversion of furfural. The observed synergistic effect between palladium and ruthenium in the tested reaction can be related to changes in the electronic state and particle size of supported metals upon interaction with each other and the Pd–Ru alloy formation.

Selective hydrogenolysis of 2-furancarboxylic acid to 5-hydroxyvaleric acid derivatives over supported platinum catalysts

Asano, Takehiro,Takagi, Hiroshi,Nakagawa, Yoshinao,Tamura, Masazumi,Tomishige, Keiichi

, p. 6133 - 6145 (2019)

The conversion of 2-furancarboxylic acid (FCA), which is produced by oxidation of furfural, to 5-hydroxyvaleric acid (5-HVA) and its ester/lactone derivatives with H2 was investigated. Monometallic Pt catalysts were effective, and other noble metals were not effective due to the formation of ring-hydrogenation products. Supports and solvents had a small effect on the performance; however, Pt/Al2O3 was the best catalyst and short chain alcohols such as methanol were better solvents. The optimum reaction temperature was about 373 K, and at higher temperature the catalyst was drastically deactivated by deposition of organic materials on the catalyst. The highest yield of target products (5-HVA, δ-valerolactone (DVL), and methyl 5-hydroxyvalerate) was 62%, mainly obtained as methyl 5-hydroxyvalerate (55% yield). The byproducts were mainly ring-hydrogenation compounds (tetrahydrofuran-2-carboxylic acid and its ester) and undetected ones (loss of carbon balance). The catalyst was gradually deactivated during reuses even at a reaction temperature of 373 K; however, the catalytic activity was recovered by calcination at 573 K. The reactions of various related substrates were carried out, and it was found that the O-C bond in the O-CC structure (1,2,3-position of the furan ring) is dissociated before CC hydrogenation while the presence and position of the carboxyl group (or methoxy carbonyl group) much affect the reactivity.

NMR-DETECTION OF INTERMEDIATES DURING HOMOGENEOUS HYDROGENATION OF DIENES USING PARAHYDROGEN

Bargon J.,Kandels, J.,Kating, P.,Thomas, A.,Woelk, K.

, p. 5721 - 5724 (1990)

1.The 1H-NMR spectra of the reaction products of hydrogenations using parahydrogen reveal information about intermediates and thus the reaction mechanism. 2.Due to its high signal enhancement the method is uniquely suited for reactions, where the catalyst itself becomes chemically modified.

Catalytic conversion of furan to gasoline-range aliphatic hydrocarbons via ring opening and decarbonylation reactions catalyzed by Pt/γ-Al 2O3

Runnebaum, Ron C.,Nimmanwudipong, Tarit,Doan, Jonathan,Block, David E.,Gates, Bruce C.

, p. 664 - 666 (2012)

Conversion of furan in the presence of H2 catalyzed by Pt/γ-Al2O3 at 573 K and 1.4 bar leads to the formation of alkanes and alkenes, some in the gasolinerange, including C7 hydrocarbons, butenes, propene, and propane.

Versatile dual hydrogenation-oxidation nanocatalysts for the aqueous transformation of biomass-derived platform molecules

Garcia-Suarez, Eduardo J.,Balu, Alina Mariana,Tristany, Mar,Garcia, Ana Beatriz,Philippot, Karine,Luque, Rafael

, p. 1434 - 1439 (2012)

Carbon-supported Pd nanoparticles have been proved to be efficient dual hydrogenation-oxidation nanocatalysts in both the selective aqueous oxidation of benzyl alcohol and the hydrogenation of furfural in water under microwave irradiation. Nanocatalysts b

Hydro-Oxygenation of Furfural in the Presence of Ruthenium Catalysts Based on Al-HMS Mesoporous Support

Roldugina,Shayakhmetov,Maksimov,Karakhanov

, p. 1306 - 1315 (2019)

Ru-containing catalyst based on an Al-HMS mesoporous aluminosilicate was synthesized. The mesoporous support and the catalyst on its basis were characterized by the methods of low-temperature desorption/adsorption of nitrogen, temperature-programmed desorption of ammonia, transmission electron microscopy, X-ray photoelectron microscopy, and energy-dispersive X-ray fluorescence analysis. The synthesized catalyst was investigated in the hydrodeoxygenation of the model compound of bio-oil, furfural, in the presence of H2O. The reaction was carried out at initial hydrogen pressures of 1–7 MPa at 200°C–300°C temperature range. The results revealed that the synthesized catalyst displayed a high activity in the hydrotransformation of furfural. The conversion was 100% in 1 hr at a 5 MPa hydrogen pressure and 200°C.

Dehydration of 1,5-pentanediol over bixbyite Sc2-xYb xO3 catalysts

Sato, Fumiya,Sato, Satoshi

, p. 129 - 133 (2012)

Vapor-phase dehydration of 1,4- and 1,5-alkanediols was investigated over three scandium ytterbium mixed oxides, Sc2-xYbxO 3 (x = 0.5, 1.0, and 1.5), to produce the corresponding unsaturated alcohols. In the dehydration of

Entropies of organolithium aggregation based on measured microsolvation numbers

Knorr, Rudolf,Menke, Thomas,Ferchland, Kathrin

, p. 468 - 472 (2013)

The recent measurement (J. Am. Chem. Soc.2008, 130, 14179-14188) of the microsolvation numbers of monodentate, nonchelating ethereal donor ligands coordinating to the monomers and dimers of two sterically shielded =C(aryl)-Li compounds permits the determination of well-founded dimerization enthalpies (ΔH0) and entropies (ΔS0) from properly formulated equilibrium constants, which must include the concentrations of the free donor ligands. The monomers are found to dimerize endothermically (ΔH0 > 0) in [D8]toluene solution in the presence of the donor tBuOMe or THF, but only slightly exothermically (ΔH 0 = -0.5 kcal per mol of dimer) with the donor Et2O. The dimerization entropies ΔS0 (in cal mol-1 K -1) with the respective equivalents of released donor ligands are 7.2 and 11.0 (with 2 equiv of tBuOMe in the two cases), 6.1 (with 2 Et 2O), and 34.1 (with 4 THF). It is shown that the improper omission of microsolvation from the equilibrium constant (a usual practice when the ligand numbers are not known) can lead to contaminated aggregation entropies ΔSψ, which may deviate considerably from the true entropies ΔS0. A method is provided for estimating the required microsolvation numbers from 13C/Li NMR coupling constants 1JC,Li for less congested organolithium types whose coordinated and free donor ligands cannot be distinguished by NMR integration.

Effects of Ligand Halogenation on the Electron Localization, Geometry and Spin State of Low-Coordinate (β-Diketiminato)iron Complexes

Bellows, Sarina M.,Brennessel, William W.,Holland, Patrick L.

, p. 3344 - 3355 (2016)

This contribution explores the influences of incorporating electron-withdrawing CF3and halide groups into (β-diketiminato)iron complexes of tetrazene and isocyanide. The synthesis of a new halogenated β-diketimine (LCF3,ClH) was accomplished by two different methods, including a novel microwave-assisted synthesis that improves the yield of the difficult condensation. Treatment of an iron(II) complex of this ligand with reductant and azide gives two diiron complexes with novel tetrazenes as bridging ligands. Structural and M?ssbauer data show that the bridging tetrazene is a radical anion. The halogenation of the supporting ligand also influences iron(I) complexes of the type [LFe(CNtBu)2], which are low-spin and square-planar with alkyl substituents but high-spin and pseudotetrahedral with halogen substituents. DFT calculations suggest that the changes from halogenation come from a combination of steric and electronic effects, and that the electronic influence of ligand halogenation is minor.

Ortho-directed lithiation of ω-phenoxy alcohols

Salteris, Constantinos S.,Kostas, Ioannis D.,Micha-Screttas, Maria,Heropoulos, George A.,Screttas, Constantinos G.,Terzis, Aris

, p. 5589 - 5592 (1999)

ω-Phenoxy alcohols, PhO(CH2)(n)OH (n = 2-7), have been subjected to metalation with 2 equiv of n-butyllithium in tetrahydrofuran/methylcyclohexane solvent. Reaction of the resulting lithiated compounds with carbon dioxide (n = 2-7), benzaldehyde (n = 2-6), benzophenone (n = 2, 3), dimethylformamide (n = 2), ethyl formate (n = 2), and chlorodiphenylphosphine (n = 3) afforded the corresponding ortho- substituted hydroxyalkoxybenzenes in yields ranging from 45 to 83%. The synthesis is also reported of five new bis[o-(ω-hydroxyalkoxy)phenyl]mercury compounds (n = 2-6), four crystal structures of which have been determined.

Displacement of the THF solvent molecule from (η5-C5H5)Mn(CO)2THF by simple two electron donor ligands: Evidence for a dissociative mechanism and determination of the Mn-THF bond strength

Coleman, Jodi E.,Dulaney, Kim E.,Bengali, Ashfaq A.

, p. 65 - 71 (1999)

The reaction between CpMn(CO)2THF (Cp=η5-C5H5, THF=tetrahydrofuran) and nitrogen containing ligands is studied in THF solution. In all cases the products of the reaction are the known CpMn(CO)2L complexes (L=piperidine, 4-acetylpyridine). The reaction of the solvated complex with both ligands studied proceeds through a purely dissociative mechanism. In good agreement with previous thermochemical measurements, kinetic analysis yields an average value of 24.0±3.0 kcal mol-1 for the CpMn(CO)2-THF bond dissociation energy. The results of the present study clarify the relationship between metal-solvent bond strengths obtained by kinetic methods and those obtained by thermochemical measurements.

Catalytic transfer hydrogenation/hydrogenolysis for reductive upgrading of furfural and 5-(hydroxymethyl)furfural

Scholz, David,Aellig, Christof,Hermans, Ive

, p. 268 - 275 (2014)

The sequential transfer hydrogenation/hydrogenolysis of furfural and 5-hydroxymethylfurfural to 2-methylfuran and 2,5-dimethylfuran was studied over in situ reduced, Fe2O3-supported Cu, Ni, and Pd catalysts, with 2-propanol as hydrogen donor. The remarkable activity of Pd/Fe 2O3 in both transfer hydrogenation/hydrogenolysis is attributed to a strong metal-support interaction. Selectivity towards hydrogenation, hydrogenolysis, decarbonylation, and ring-hydrogenation products is shown to strongly depend on the Pd loading. A significant enhancement in yield to 62%, of 2-methylfuran and 2-methyltetrahydrofuran was observed under continuous flow conditions.

Synthesis of common-sized heterocyclic compounds by intramolecular cyclization over halide cluster catalysts

Nagashima, Sayoko,Sasaki, Tomoaki,Kamiguchi, Satoshi,Chihara, Teiji

, p. 764 - 766 (2015)

Five- to seven-membered common-sized heterocyclic compounds containing an oxygen, sulfur, or nitrogen were synthesized by the intramolecular condensation of α,ω-hydroxy, mercapto, or amino alkanes, respectively, over halide cluster complexes as a thermally stable molecular solid weak acid catalyst in the gas phase at temperatures ≥150 °C. From ω- mercapto and ω-amino alcohols, cyclic sulfides and amines were obtained, respectively. These unimolecular reactions are thermodynamically and kinetically favored.

-

Heine,Siegfried

, p. 489 (1954)

-

One-pot synthesis of 1-butylpyrrolidine and its derivatives from aqueous ammonia and 1,4-butandiol over CuNiPd/ZSM-5 catalysts

Long, Yan,Liu, Shimin,Ma, Xiangyuan,Lu, Liujin,He, Yude,Deng, Youquan

, p. 16708 - 16712 (2020)

The synthesis of 1-butylpyrrolidine and its derivatives (1-butylpyrrolidine with a little of 1-butenylpyrrolidines) was developed via a one-pot method from ammonia and 1,4-butandiol. Here, the product of 1-butylpyrrolidine was emphatically investigated, and the yield was 76% under the optimized conditions. Such a route was realized through successive N-alkylation using aqueous ammonia as the nitrogen source over the CuNiPd/ZSM-5 catalyst, which was prepared by a simple incipient wetness method. In this route, 1,4-butandiol not only participated in the formation of the N-heterocycle, but also acted as an alkylating reagent. This work offers a straightforward, economical route for 1-butylpyrrolidine and its derivatives. This journal is

Liquid phase chemo-selective catalytic hydrogenation of furfural to furfuryl alcohol

Sharma, Rajesh V.,Das, Umashankar,Sammynaiken, Ramaswami,Dalai, Ajay K.

, p. 127 - 136 (2013)

Novel Cu:Zn:Cr:Zr based catalysts were developed for the hydrogenation of furfural to furfuryl alcohol. Physio-chemical characterizations of the catalysts were performed by using XRD, BET, FTIR, TPR, NH3-TPD, ICP-MS, SEM, TEM, CO-chemisorption, and XANES techniques. Among all the catalysts prepared, the catalysts Cu(3):Zn(2):Cr(1):Zr(3) and Cu(3):Zn(2):Cr(1):Zr(4), referred as Cat-C and Cat-D, respectively are the best ones to demonstrate high activity and selectivity profile. Cat-C and Cat-D exhibited 100% conversion and 96% selectivity at 170 ± 2 °C and 2 MPa of hydrogen pressure. The role of constituent metals in the catalyst was delineated. Incorporation of Zn increases the activity for furfural conversion whereas Zr contributes significantly to the selectivity of furfuryl alcohol. It was also found that Zr loading not only increases the acidity of the catalyst but also helps in the dispersion of metallic Cu. The particle size of metallic Cu was found to be in the range of 17-19 nm as confirmed by TEM, XRD and CO chemisorption techniques. XANES analysis confirmed the presence of copper in Cu0 and Cu 2+ oxidation states in Cat-C (freshly reduced) and Cat-C (fresh), respectively. Hydrogenation of furfural to furfuryl alcohol follows a pseudo-first order reaction with an the apparent activation energy of 24.4 kcal/mol. Cat-C was recycled at least 4 times for the hydrogenation of furfural with no loss of activity and selectivity when compared to the fresh catalyst.

Shape and ligand effect of palladium nanocrystals on furan hydrogenation

Sun, Changyong,Cao, Zhou,Wang, Jiandian,Lin, Liangbiao,Xie, Xiaowei

, p. 2567 - 2574 (2019)

The Pd nanocrystals, including cubes, octahedra and wire, were prepared by shape-controlled solution phase reduction. The shape-dependent effect of Pd, and the effect of residual halogen ions and PVP, were investigated in selective hydrogenation of furan to tetrahydrofuran (THF). It was found that the residual halogen ions and PVP on the surface of Pd nanocrystals possibly reduced the hydrogenation activity and in turn it prevented the further reaction such as ring opening, so high selectivity towards THF was achieved even at high temperature. The 5-fold twinned wire displayed poor activity in furan hydrogenation due to a large amount of strongly adsorbed iodide ion residues covering most of the Pd active sites. An appropriate PVP residue is necessary, which can effectively maintain the shape and size stability of the Pd nanocube and octahedron, although the residual PVP partially blocks active Pd sites and reduces the activity for furan hydrogenation. The Pd nanocube enclosed by {100} facets exhibited about two times higher turnover frequency and lower apparent activation energy compared to the octahedron enclosed by {111} facets, suggesting a significant shape-dependent effect.

Interfacial effect of Pd supported on mesoporous oxide for catalytic furfural hydrogenation

Lee, Hojeong,Nguyen-Huy, Chinh,Jeong Jang, Eun,Lee, Jihyeon,Yang, Euiseob,Lee, Man Sig,Kwak, Ja Hun,An, Kwangjin

, p. 291 - 300 (2021)

Highly dispersed Pd is loaded onto different types of mesoporous oxide supports to investigate the synergetic metal-support effect in catalytic furfural (FAL) hydrogenation. Ordered mesoporous Co3O4, MnO2, NiO, CeO2, and Fe2O3 are prepared by the nanocasting and the supported Pd on mesoporous oxide catalysts are obtained by the chemical reduction method. It is revealed that mesoporous oxides play an important role on Pd dispersion as well as the redox behavior of Pd, which determines the final FAL conversion. Among the catalysts used, Pd/Co3O4 shows the highest conversion in FAL hydrogenation and distinct product selectivity toward 2-methylfuran (MF). While FAL is converted via two distinct pathways to produce either furfuryl alcohol (FA) via aldehyde hydrogenation or MF via hydrogenolysis, MF as a secondary product is derived from FA via the hydrogenolysis of C–O over the Pd/Co3O4 catalyst. It is revealed that FAL is hydrogenated to FA preferentially on the Pd surface; then the secondary hydrogenolysis to MF from FA is further promoted at the interface between Pd and Co3O4. We confirm that the reaction pathway over Pd/Co3O4 is totally different from other catalysts such as Pd/MnO2, which produces FA dominantly. The characteristics of the mesoporous oxides influence the Pd-oxide interfaces, which determine the activity and selectivity in FAL hydrogenation.

Liquid phase hydrodeoxygenation of furfural over laponite supported NiPMoS nanocatalyst: Effect of phosphorus addition and laponite support

Krishnan, P. Santhana,Umasankar,Tamizhdurai,Mangesh,Shanthi

, (2021)

Unsupported and laponite supported NiPMoS catalysts were prepared under the hydrothermal method and investigated for liquid-phase hydrodeoxygenation of furfural in a high-pressure batch reactor at 423 ?K ? 463 ?K under 20 ?bar H2 pressure. The reaction significantly produced 94% of furfural conversion with 75% yield of 2-MF on NiPMoS catalyst whereas, NiPMoS/Lap catalyst exhibited 28% of 2-MF yield with complete conversion at 463 ?K under 20 ?bar H2 pressure in toluene solvent. The influence of process parameters such as reaction temperature, reactant volume, catalyst compositions, and hydrogen pressure on furfural conversion and product yield was investigated in detail. The high reactivity and synergetic effect of the NiPMoS catalyst are due to added phosphorus, which has a profound influence on the structure of the catalyst, thereby increasing surface acidity, basicity, hydrogen consumption, and a number of MoS2 fringes and the dispersion of MoS2 on the surface of the support. The catalysts were characterized based on HRTEM, H2, CO2, and NH3 TPD, FT–IR, FT–Raman, DRS UV–Vis, XRD, N2–physisorption, and TGA. Recyclability, N2–physisorption, and XRD results confirm the stability and practical applicability of the catalyst for industrial applications.

Heine et al.

, p. 4778 (1953)

Chromium-free Cu?Mg/γ-Al2O3-an active catalyst for selective hydrogenation of furfural to furfuryl alcohol

Arundhathi, Racha,Newalkar, Bharat L.,Reddy, Panyala Linga,Samanta, Chanchal

, p. 41120 - 41126 (2020)

Development of a chromium (Cr)-free hydrogenation catalyst is very important to replace the existing hazardous Cr based catalyst used in the furfural hydrogenation to furfuryl alcohol. Herein, we report synthesis of well-dispersed copper nanoparticles supported on hydrothermally stable magnesium doped alumina (Cu?Mg/γ-Al2O3) for selective hydrogenation of furfural to furfuryl alcohol. The prepared catalyst was characterized by X-ray Photoelectron Spectroscopy (XPS), Auger Electron Spectroscopy (AES), Powder X-ray Diffraction (PXRD), Surface Area Analysis (SAA), High Resolution-Transmission Electron Microscopy (HR-TEM), Temperature Programmed Reduction/Desorption (TPR/TPD) and Inductively Coupled Plasma-Atomic Emission Spectroscopy (ICP-AES) to understand textural properties of the catalyst. The prepared catalyst was found to be highly active and selective with 99% conversion of furfural and 94% selectivity for furfuryl alcohol under solvent free conditions at 443.15 K and 2 MPa of hydrogen pressure. It was also observed that the Cu?Mg/γ-Al2O3 catalyst is reusable (up to six runs) while maintaining its high activity and selectivity (≥94%) in the hydrogenation of furfural to furfuryl alcohol. This journal is

Synthesis and reactivity of naphthalene complexes of ytterbium

Bochkarev, M. N.,Trifonov, A. A.,Fedorova, E. A.,Emelyanova, N. S.,Basalgina, T. A.,et al.

, p. 217 - 224 (1989)

The complexes formulated as C10H8Ybx(THF)y (X = 1-2, y = 2-4) have been obtained as black pyrophoric powders by reactions of anhydrous ytterbium diiodide with a lithium naphthalide in THF.The reactions of samarium and europium iodide

Mechanism of formation of tetrahydrofuran in the catalytic hydrogenation of dialkyl succinates

Timofeev,Bazanov,Zubritskaya

, p. 1537 - 1541 (2010)

The kinetics of formation of tetrahydrofuran from dibutyl succinate were studied. The mechanism of catalytic hydrogenation of dialkyl succinates was found to involve consecutive formation of ?-butyrolactone, butane-1,4-diol, and tetrahydrofuran. Parameters of kinetic equations that properly describe the system of concurrent and consecutive reactions were determined.

Heterogeneous CaO-ZrO2 acid-base bifunctional catalysts for vapor-phase selective dehydration of 1,4-butanediol to 3-buten-1-ol

Zhang, Qian,Zhang, Yin,Li, Haitao,Gao, Chunguang,Zhao, Yongxiang

, p. 233 - 239 (2013)

A series of acid-base bifunctional CaO-ZrO2 catalysts was prepared simply by the impregnation method and evaluated for the vapour-phase dehydration of 1,4-butanediol (BDO). The effects of CaO content and calcination temperature on the catalytic properties of the CaO-ZrO2 catalysts were investigated. It was found that the catalyst with 12.5 wt% CaO and at a calcination temperature of 650°C exhibited favorable catalytic performance and good stability for the selective dehydration of BDO to 3-buten-1-ol (BTO). The maximum BTO selectivity and BDO conversion reached 68.9% and 94.6%, respectively. The formation of by-product, THF, was markedly suppressed. These catalysts were characterized by N2 physisorption, XRD, FT-IR spectra, NH3-TPD and CO2-TPD. The results indicated that the CaO-ZrO2 catalysts showed higher basicity density and similar acidity density compared to unmodified ZrO2 due to the formation of Ca-O-Zr Hetero-linkage by CaO introduction. The catalytic performance depended on the coexistence of acidic and basic sites on the surface of catalysts.

Furfural hydrodeoxygenation (HDO) over silica-supported metal phosphides – The influence of metal–phosphorus stoichiometry on catalytic properties

Lan, Xuefang,Pestman, Robert,Hensen, Emiel J.M.,Weber, Thomas

, p. 181 - 193 (2021)

The gas-phase hydrodeoxygenation (HDO) of furfural, a model compound for bio-based conversion, was investigated over transition metal phosphide catalysts. The HDO activity decreases in the order Ni2P ≈ MoP > Co2P ≈ WP ? Cu3P > Fe2P. Nickel phosphide phases (e.g., Ni2P, Ni12P5, Ni3P) are the most promising catalysts in the furfural HDO. Their selectivity to the gasoline additives 2-methylfuran and tetrahydro-2-methylfuran can be adjusted by varying the P/Ni ratio. The effect of P on catalyst properties as well as on the reaction mechanism of furfural HDO were investigated in depth for the first time. An increase of the P stoichiometry weakens the furan-ring/catalyst interaction, which contributes to a lower ring-opening and ring-hydrogenation activity. On the other hand, an increasing P content does lead to a stronger carbonyl/catalyst interaction, i.e., to a stronger η2(C, O) adsorption configuration, which weakens the C1[sbnd]O1 bond (Scheme 1) in the carbonyl group and enhances the carbonyl conversion. Phosphorus species can also act as Br?nsted acid sites promoting C1[sbnd]O1 (Scheme 1) hydrogenolysis of furfuryl alcohol, hence contributing to higher production of 2-methylfuran.

Preparation of Er2O3 nanorod catalyst without using organic additive and its application to catalytic dehydration of 1,4-butanediol

Sato, Fumiya,Yamada, Yasuhiro,Sato, Satoshi

, p. 593 - 594 (2012)

Er2O3 nanorods were successfully prepared with hydrothermal treatment without using organic additives such as surfactant, fatty acid, or alcohol. Er2 O3 nanorods were obtained under high temperature and/or long reaction times. Er2O3 nanorods mainly exposed {440} and {400} facets on the surface. Er2O3 nanorods showed excellent catalytic activity compared to commercial Er2O3 nanoparticles in the dehydration of 1,4-butanediol to produce 3-buten-1-ol.

-

Eliel,Traxler

, p. 4049,4051 (1956)

-

Colloidal and Nanosized Catalysts in Organic Synthesis: XXIV. Study of Hydrogenation of Furan and Its Derivatives in the Presence of MgO-Supported Nickel and Cobalt Nanoparticles

Gendler, T. A.,Mokhov, V. M.,Nebykov, D. N.,Popov, Yu. V.,Shemet, V. V.,Shirkhanyan, P. M.

, p. 931 - 935 (2020)

Abstract: The processes of hydrogenation of furan and its derivatives (2-methylfuran, furfuryl alcohol, and furfural) in plug-flow type reactor under atmospheric hydrogen pressure at 20–220°С in the presence of supported nickel nanoparticles prepared via chemical reduction have been investigated. It has been found that nickel nanoparticles supported on magnesium oxide surface are the most reactive and stable under the considered conditions. This catalyst allows the corresponding hydrogenation products with 100percent yield and complete conversion of the substrate.

Conversion of 1,4-Butanediol to Furan Compounds on Cobalt Catalysts in the Liquid Phase

Geiman, I. I.,Bulenkova, L. F.,Lazdin'sh, A. A.,Veinberg, A. K.,Slavinskaya, V. A.,Avots, A. A.

, p. 314 - 316 (1981)

The transformation of 1,4-butanediol on cobalt catalysts applied to kieselguhr in the liquid phase under periodic and continuous conditions was investigated.When the reaction is carried out under periodic conditions, the principal reaction products are 2,3-dihydrofuran, tetrahydrofuran, and γ-butyrolactone.An increase in the selectivity of the formation of 2,3-dihydrofuran as the temperature is raised was established. 2,3-Dihydrofuran is obtained in 63-73 mole percent yields under optimum conditions. 2,3-Dihydrofuran is converted to tetrahydrofuran when the process is carried out under continuous conditions on a tableted cobalt catalyst.

-

Holtz et al.

, p. 3175,3178 (1973)

-

Investigating hydrogenation and decarbonylation in vapor-phase furfural hydrotreating over Ni/SiO2 catalysts: Propylene production

Chen, Szu-Hua,Tseng, Ya-Chun,Yang, Sheng-Chiang,Lin, Shawn D.

, (2021)

Furfural can be mass-produced from lignocellulose biomass and can be a platform chemical for producing valuable chemicals. In this study, we examine Ni/SiO2 catalysts for the conversion of furfural under a hydrogen atmosphere. The reactivity an

Reduction of Dicarboxylic Acid Anhydride with 2-Propanol over Hydrous Zirconium Oxide

Takahashi, Kyoko,Shibagaki, Makoto,Matsushita, Hajime

, p. 262 - 266 (1992)

The reduction of dicarboxylic acid anhydrides with 2-propanol proceeded efficiently over hydrous zirconium oxide to give the corresponding lactones and cyclic ethers.Secondary and primary alcohols, with the exception of methanol, are able to act as hydride donors in this reduction.The reduction proceeded as nearly second order concerning the concentration of 2-propanol and minus order concerning that of acid anhydride.These results suggest that the reduction was preferred under lower concentrations of acid anhydride and higher concentrations of 2-propanol.The selectivity of lactone or ether could be changed by the reaction temperature or the molar ratio of dicarboxylic acid anhydride to alcohol.

Efficient aqueous hydrogenation of biomass platform molecules using supported metal nanoparticles on Starbons

Luque, Rafael,Clark, James H.,Yoshida, Kenta,Gai, Pratibha L.

, p. 5305 - 5307 (2009)

An efficient protocol for the hydrogenation of platform molecules (e.g. succinic acid) in aqueous environments using supported metal nanoparticles on polysaccharide derived mesoporous carbonaceous materials is reported for the first time.

Hydrogenation of succinic acid to tetrahydrofuran (THF) over rhenium catalyst supported on H2SO4-treated mesoporous carbon

Hong, Ung Gi,Park, Hai Woong,Lee, Joongwon,Hwang, Sunhwan,Yi, Jongheop,Song, In Kyu

, p. 141 - 148 (2012)

Mesoporous carbon (MC) prepared by a surfactant-templating method was treated with different H2SO4 concentration (X = 0, 0.2, 0.4, 0.6, 0.8, and 1.0 M) for use as a support (MC-X) for rhenium catalyst. Rhenium catalysts supported on H2SO4-treated mesoporous carbons (Re/MC-X) were then prepared by an incipient wetness impregnation method, and they were applied to the liquid-phase hydrogenation of succinic acid to tetrahydrofuran (THF). The effect of H2SO4 treatment on the physicochemical properties and catalytic activity of Re/MC-X catalysts (X = 0, 0.2, 0.4, 0.6, 0.8, and 1.0) was investigated. It was observed that MC-X supports showed different pore characteristics depending on H2SO 4 concentration. As a result, Re/MC-X catalysts showed different rhenium particle size. In the liquid-phase hydrogenation of succinic acid to tetrahydrofuran (THF), conversion of succinic acid and yield for THF showed volcano-shaped curves with respect to H2SO4 concentration. Thus, an optimal H2SO4 concentration was required to achieve maximum catalytic performance of Re/MC-X. Yield for THF in the hydrogenation of succinic acid increased with decreasing rhenium particle size of Re/MC-X catalysts. Among the catalysts tested, Re/MC-0.4 with the smallest rhenium particle size showed the highest yield for THF.

-

Heisig

, p. 525 (1939)

-

PRODUCTION METHOD OF CYCLIC COMPOUND

-

Paragraph 0057-0058; 0062-0063, (2021/05/05)

PROBLEM TO BE SOLVED: To provide an industrially simple production method of a cyclic compound. SOLUTION: A production method of a cyclic compound includes a step to obtain a reduced form (B) by reducing an unsaturated bond in a ring structure of an aromatic compound (A) by means of catalytic hydrogenation of the aromatic compound (A) or its salt using palladium carbon as a catalyst under a normal pressure, in which the aromatic compound (A) has one or more ring structures selected from a group consisting of a five membered-ring, a six membered-ring, and a condensed ring of the five membered-ring or the six membered-ring with another six membered-ring, a hetero atom can be included in the ring structure, and the aromatic compound (A) can have one or two side chains bonded to the ring structure and does not have any carbon-carbon triple bond in the side chain. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

H2-Free Selective Dehydroxymethylation of Primary Alcohols over Palladium Nanoparticle Catalysts

Yamaguchi, Sho,Kondo, Hiroki,Uesugi, Kohei,Sakoda, Katsumasa,Jitsukawa, Koichiro,Mitsudome, Takato,Mizugaki, Tomoo

, p. 1135 - 1139 (2020/12/29)

The dehydroxymethylation of primary alcohols is a promising strategy to transform biomass-derived oxygenates into hydrocarbon fuels. In this study, a novel, highly efficient, and reusable heterogeneous catalyst system was established for the H2-free dehydroxymethylation of primary alcohol using cerium oxide-supported palladium nanoparticles (Pd/CeO2). A wide range of aliphatic and aromatic alcohols including biomass-derived alcohols were converted into the corresponding one-carbon shorter hydrocarbons in high yields in the absence of any additives, accompanied by the production of H2 and CO. Pd/CeO2 was easily recovered from the reaction mixture and reused, retaining its high activity, thus, providing a simple and sustainable methodology to produce hydrocarbon fuels from biomass-derived oxygenates.

Process route upstream and downstream products

Process route

Butane-1,4-diol
110-63-4

Butane-1,4-diol

pyrrolidine
123-75-1

pyrrolidine

4-Aminobutanol
13325-10-5

4-Aminobutanol

Conditions
Conditions Yield
With ammonia; CrZMS-5; at 300 ℃; for 4h;
48.0 % Chromat.
(4-Hydroxy-butyl)-trimethyl-ammonium; hydroxide
58390-09-3

(4-Hydroxy-butyl)-trimethyl-ammonium; hydroxide

homoalylic alcohol
627-27-0

homoalylic alcohol

methoxy-1 butene-3
4696-30-4

methoxy-1 butene-3

4-dimethylamino-1-butanol
13330-96-6

4-dimethylamino-1-butanol

dimethylamino-1 methoxy-4 butane
33962-95-7

dimethylamino-1 methoxy-4 butane

Conditions
Conditions Yield
at 110 - 120 ℃; Product distribution;
tetrahydrofuran-3-carboxaldehyde
79710-86-4

tetrahydrofuran-3-carboxaldehyde

3-methyltetrahydrofuran
13423-15-9

3-methyltetrahydrofuran

3-tetrahydrofuranmethanol
124391-75-9,124506-31-6,15833-61-1

3-tetrahydrofuranmethanol

Conditions
Conditions Yield
With isopropyl alcohol; at 280 - 330 ℃; for 4 - 6h;
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

1-methoxy-1,4-butanediol

1-methoxy-1,4-butanediol

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

4-hydroxy-butanoic acid 4-hydroxybutyl ester

4-hydroxy-butanoic acid 4-hydroxybutyl ester

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

methyl 4-hydroxybutanoate
925-57-5

methyl 4-hydroxybutanoate

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; at 190 ℃; under 46504.7 Torr; Gas phase;
79.1%
10.4%
5.3%
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

2-(4'-hydroxybutoxy)-tetrahydrofuran
64001-06-5

2-(4'-hydroxybutoxy)-tetrahydrofuran

Butane-1,4-diol
110-63-4

Butane-1,4-diol

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich; at 150 - 280 ℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);
98%
1%
0.4%
0.5%
4-butanolide
96-48-0

4-butanolide

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-hydroxybutanoic acid
591-81-1

4-hydroxybutanoic acid

succinic acid
110-15-6

succinic acid

terephthalic acid
100-21-0

terephthalic acid

acetic acid
64-19-7,77671-22-8

acetic acid

propionic acid
802294-64-0,79-09-4

propionic acid

(2E)-but-2-enedioic acid
110-17-8,26099-09-2

(2E)-but-2-enedioic acid

Conditions
Conditions Yield
With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2; at 110 ℃; for 170 - 1009h; Product distribution / selectivity;
0.04%
0.28%
4.34%
0%
1.24%
0%
0%
85.51%
0%
0.86%
3-tetrahydrofuranmethanol
124391-75-9,124506-31-6,15833-61-1

3-tetrahydrofuranmethanol

3-methyltetrahydrofuran
13423-15-9

3-methyltetrahydrofuran

dihydro-4-methyl-2(3H)-furanone
64190-48-3,65284-00-6,70470-05-2,1679-49-8

dihydro-4-methyl-2(3H)-furanone

(+/-)-2-methyl-1-butanol
137-32-6

(+/-)-2-methyl-1-butanol

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; Catalyst C prepared in Example C (nickel on mixed silica-zirconia support Zr:Si:Ni 10:28:1); In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst A prepared in Example A comprising nickel, molybdenum, and hydrous zirconia Zr:Mo:Ni 50:1:20; In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst B prepared in Example Bcomprising nickel, molybdenum, and hydrous zirconia Zr:Mo:Ni 30:1:10; In water; at 280 - 300 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst D prepared in Example D (nickel on the mixed silica-zirconia support Zr:Si:Ni 10:5:2); In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst E prepared in Example E (nickel on mixed silica-zirconia Zr:Si:Ni 1:1:1); In water; at 300 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst F prepared in Example F (nickel and niobium - containing zirconia catalyst Zr:Nb:Ni 20:1:10); In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst H prepared in Example H (nickel molybdate reduced under hydrogen Mo:Ni 1:1); In water; at 280 - 300 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
With hydrogen; Catalyst J prepared in Example J (nickel-molybdenum catalyst Mo:Ni 1:1); In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
3-tetrahydrofuranmethanol
124391-75-9,124506-31-6,15833-61-1

3-tetrahydrofuranmethanol

3-methyltetrahydrofuran
13423-15-9

3-methyltetrahydrofuran

dihydro-4-methyl-2(3H)-furanone
64190-48-3,65284-00-6,70470-05-2,1679-49-8

dihydro-4-methyl-2(3H)-furanone

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; Catalyst G prepared in Example G (nickel on mixed silica-alumina Al:Si:Ni 1:1:1); In water; at 280 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
3-tetrahydrofuranmethanol
124391-75-9,124506-31-6,15833-61-1

3-tetrahydrofuranmethanol

3-methyltetrahydrofuran
13423-15-9

3-methyltetrahydrofuran

dihydro-4-methyl-2(3H)-furanone
64190-48-3,65284-00-6,70470-05-2,1679-49-8

dihydro-4-methyl-2(3H)-furanone

(+/-)-2-methyl-1-butanol
137-32-6

(+/-)-2-methyl-1-butanol

Conditions
Conditions Yield
With hydrogen; Criterion Catalyst 424 (C-424) comprising 3.0-4.5 weight percent nickel on alumina modified with phosphorus (6.0-9.0percent) and molybdenum (16.5-22.5percent) oxides; In water; at 280 - 300 ℃; for 1h; under 10336 - 41329.1 Torr; Product distribution / selectivity;
With hydrogen; Catalyst F prepared in Example F (nickel and niobium - containing zirconia catalyst Zr:Nb:Ni 20:1:10); In water; at 250 ℃; for 1h; under 10336 Torr; Product distribution / selectivity;
D-sorbitol
50-70-4

D-sorbitol

TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

2,5-dimethyltetrahydrofuran
1003-38-9

2,5-dimethyltetrahydrofuran

methanol
67-56-1

methanol

propan-1-ol
71-23-8

propan-1-ol

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

3-methyl-cyclopentanone
1757-42-2,6195-92-2

3-methyl-cyclopentanone

propylene glycol
57-55-6,63625-56-9

propylene glycol

ethanol
64-17-5

ethanol

n-hexan-3-ol
623-37-0

n-hexan-3-ol

2-methylpentan-1-ol
105-30-6

2-methylpentan-1-ol

(S)-Ethyl lactate
687-47-8

(S)-Ethyl lactate

pentan-1-ol
71-41-0

pentan-1-ol

vinyl formate
692-45-5

vinyl formate

n-hexan-2-one
591-78-6

n-hexan-2-one

n-hexan-3-one
589-38-8

n-hexan-3-one

Isopropyl acetate
108-21-4

Isopropyl acetate

3-Hydroxy-2-pentanone
3142-66-3,113919-08-7

3-Hydroxy-2-pentanone

acetic acid
64-19-7,77671-22-8

acetic acid

propionaldehyde
123-38-6

propionaldehyde

2-Pentanone
107-87-9

2-Pentanone

propionic acid
802294-64-0,79-09-4

propionic acid

1-Hydroxy-2-butanone
5077-67-8

1-Hydroxy-2-butanone

2,5-hexanedione
110-13-4

2,5-hexanedione

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

acetone
67-64-1

acetone

pentan-3-one
96-22-0

pentan-3-one

isobutyric Acid
79-31-2

isobutyric Acid

butanone
78-93-3

butanone

iso-butanol
78-92-2,15892-23-6

iso-butanol

hexanoic acid
142-62-1

hexanoic acid

Isosorbide
652-67-5

Isosorbide

butyric acid
107-92-6

butyric acid

2.3-butanediol
513-85-9

2.3-butanediol

hexan-1-ol
111-27-3

hexan-1-ol

valeric acid
109-52-4

valeric acid

Conditions
Conditions Yield
platinum on carbon; In water; for 3h; Direct aqueous phase reforming;

Global suppliers and manufacturers

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  • VD BIOTECH LIMITED
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  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:30
  • Country:China (Mainland)
  • Hangzhou Dingyan Chem Co., Ltd
  • Business Type:Trading Company
  • Contact Tel:86-571-86465881,86-571-87157530,86-571-88025800
  • Emails:sales@dingyanchem.com
  • Main Products:95
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  • LIDE PHARMACEUTICALS LIMITED
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-25-58409506
  • Emails:lide@lidepharma.com
  • Main Products:56
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
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