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Cas Database

120-92-3

120-92-3

Identification

  • Product Name:Cyclopentanone

  • CAS Number: 120-92-3

  • EINECS:204-435-9

  • Molecular Weight:84.1179

  • Molecular Formula: C5H8O

  • HS Code:2914 29 00

  • Mol File:120-92-3.mol

Synonyms:Adipicketone;Adipin keton;Dumasin;Ketocyclopentane;Ketopentamethylene;NSC 4122;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician. Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

  • Fire-fighting measures: Suitable extinguishing media ALCOHOL FOAM, CARBON DIOXIDE, DRY CHEM. Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substance may be transported hot. For hybrid vehicles, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. If molten aluminum is involved, refer to ERG Guide 169. (ERG, 2016) 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. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. 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. Fireproof. Separated from acids. Cool. Keep in the dark. Keep in a well-ventilated room. Store only if stabilized.

  • 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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  • Manufacture/Brand:TRC
  • Product Description:Cyclopentanone
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Cyclopentanone >99.0%(GC)
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  • Product Description:Cyclopentanone >99.0%(GC)
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  • Product Description:Cyclopentanone
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  • Product Description:Cyclopentanone
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Cyclopentanone ≥99%, FG
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  • Product Description:Cyclopentanone ≥99%, FG
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Cyclopentanone ≥99%, FG
  • Packaging:5 kg
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Cyclopentanone ≥99%, FG
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Relevant articles and documentsAll total 487 Articles be found

Efficient conversion of furfural into cyclopentanone over high performing and stable Cu/ZrO2 catalysts

Zhang, Yifeng,Fan, Guoli,Yang, Lan,Li, Feng

, p. 117 - 126 (2018)

Currently, biomass transformation to produce high value-added chemicals and liquid biofuels is attracting more and more interest by the virtue of its importance in the sustainable development of human society. Herein, we reported the conversion of furfural (FFA) into cyclopentanone (CPO) in water over high performing and stable Cu/ZrO2 catalysts prepared by our developed one-pot reduction-oxidation method. It was demonstrated that surface structures and catalytic performances of catalysts could be delicately adjusted by varying the calcination temperatures for catalyst precursors. Especially, an appropriate calcination temperature of 500 °C could significantly enhance the interactions between surface Cu species and the ZrO2 support, thus greatly facilitating the formation of Cu+-O-Zr-like structure at the metal-support interface, and the resulting Cu/ZrO2 catalyst showed a superior catalytic performance with a high CPO yield of 91.3% under mild reaction conditions (i.e. a low hydrogen pressure of 1.5 MPa and 150 °C) to other metal oxides supported copper catalysts prepared by the conventional impregnation. It was revealed that in addition to surface acidic sites, surface Cu+/(Cu°+Cu+) ratio also played a key role in promoting the formation of CPO in the present Cu/ZrO2 catalytic system.

Catalytic Oxidation of Cyclopentene by O2 over Pd(II)-SBA-15 Complexes

Yue, Lumin,Wang, Zhenwei,Bao, Lele,Fu, Wei,Xu, Li,Li, Jun,Lu, Guanzhong

, p. 2269 - 2278 (2017)

Abstract: Novel catalysts with Pd(II)-picolinamide complexes anchored into the channels of mesoporous material SBA-15 were prepared for chemical transformation of cyclopentene, and characterized in details. Spectra of 29Si NMR, 13C NMR and XPS revealed the organic ligands were grafted into the SBA-15 and Pd(II) complexes formed. Spacial diversity of the complexes, especially distances from –C=O to N on pyridyl cycles, may influence electronic distribution of conjugated system and further the catalytic activity. With the help of the newly synthesized catalytic materials, a new heterogeneous oxidation system was developed for selective catalytic transformation of cyclopentene to cyclopentanone with molecular oxygen as the sole oxidant. Analytic results of the reaction mixtures indicated that all catalysts exhibited high activity, while the cat.1 and cat.2 with 2-pyridinecarbonyl or 3-pyridinecarbonyl on the ligands gave better yields of cyclopentanone. 96.2% conversion of cyclopentene and 76.3% yied of cyclopentanone were achieved over the catalyst cat.2 under the conditions of 0.7?MPa O2, 323?K and 6?h reaction. In addition, the catalysts were also appealing for easy separation and recyclable property. Graphical Abstract: [Figure not available: see fulltext.] A new heterogeneous reaction system was developed for the catalytic oxidation of cyclopentene to cyclopentanone by molecular oxygen over novel catalysts. The synthesized catalysts are comprised of Pd(II)-picolinamide complexes anchored into the channels of SBA-15. The new system was efficient for the mentioned reaction, and the catalysts were reusable.

-

Brooks

, p. 3693,3695 (1958)

-

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Brown,Hess

, p. 2206 (1969)

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PREPARATION OF KETONES BY A NOVEL DECARBALKOXYLATION OF β-KETO ESTERS: STEREOELECTRONIC ASSISTANCE TO C-C BOND FISSION

Aneja, R.,Hollis, W. M.,Davies A. P.,Eaton, G.

, p. 4641 - 4644 (1983)

Reaction of β-keto esters with the sodium derivative of propane-1,2-diol in an excess of anhydrous propane-1,2-diol causes facile decarboxylation to ketones in excellent yields.

Trinuclear triangular copper(II) clusters - Synthesis, electrochemical studies and catalytic peroxidative oxidation of cycloalkanes

Di Nicola, Corrado,Garau, Federica,Karabach, Yauhen Y.,Martins, Luisa M. D. R. S.,Monari, Magda,Pandolfo, Luciano,Pettinari, Claudio,Pombeiro, Armando J. L.

, p. 666 - 676 (2009)

The reactions of CuII carboxylates (valerate, 2-methylbutyrate, hexanoate, heptanoate) with pyrazole (Hpz) in EtOH or EtOH/water solutions easily afford the triangular trinuclear copper derivatives [Cu 3(μ3-OH)(μ-pz)3(RCOO)2(L) x] [R = CH3(CH2)3, L = H 2O, x = 1 for 5; R = CH3CH2CH(CH3), L = EtOH, x = 2 for 6; R = CH3(CH2)4, L = EtOH, x = 1 for 7; R = CH3(CH2)5, L = EtOH, x = 1 for 8] as it has been previously found for R = H, L = Hpz, x = 2, (1); R = CH3, L = Hpz, x = 1, (2); R = CH3CH2, L = EtOH, x = 1, (3) and [Cu3(μ3-OH)(μ-pz) 3-(CH3(CH2)2COO)2(MeOH) (H2O)], (4). The trinuclear structure common to 5-8 has been assigned on the basis of magnetic susceptibility studies, ESI MS, IR and UV/Vis spectroscopy as well as 1H NMR measurements. The room temp. magnetic susceptibilities of 5-8 almost correspond to the presence of a single unpaired electron for each trinuclear unit. The IR spectra exhibit signals due to the bridging μ3-OH in accordance with what was observed in the spectra of 1-4. Solid-state and MeOH solution UV/Vis spectra show the same features previously reported for 1-4 and 1H NMR spectra of 1-8 show almost identical low field signals that can be assigned to pz- hydrogens. A detailed investigation of the supramolecular structures of 1 and 4 and the single-crystal X-ray study of the polymeric paddlewheel Cu(2-methylbutyrate) 2, A, are also reported. Electrochemical experiments show that in 1-8 the CuII ions can be reduced, in distinct steps, to CuI and Cu0. All the complexes act as catalysts or catalyst precursors for the efficient peroxidative oxidation, by aqueous hydrogen peroxide in acetonitrile and at room temp., of cycloalkanes RH (cyclohexane and cyclopentane) to the corresponding cyclic alcohols and ketones, with overall yields of up to 34% and TONs up to 42. Radical pathways involving the formation of alkyl hydroperoxides (ROOH) are involved. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Synthesis of Unsaturated Spiroacetals, Cyclopentanone Derivatives, in the Presence of Natural Aluminosilicate Modified with Zirconium Cations

Abbasov,Alimardanov, Kh. M.,Abbaszade,Guseinova,Azimli

, p. 603 - 607 (2019)

Abstract: Conditions for the condensation of cyclopentanone and n-valeric aldehyde to 2-pentylidenecyclopentanone in the presence of an alcoholic solution of piperidine have been developed. The isomerization of the latter in a continuous-flow system over γ-Al2O3 yields 2-pentylcyclopent-2-en-1-one. The condensation of the obtained unsaturated ketones with ethane-1,2-diol in the presence of a heterogeneous catalyst, a natural aluminosilicate (perlite) modified with zirconyl sulfate, has been studied. The optimum conditions for the preparation of the corresponding unsaturated spiroacetals have been found. The synthesized compounds can be used as synthetic fragrances for different purposes.

Kinetics and mechanisms of the thermal decomposition of 2-methyl-1,3-dioxolane, 2,2-dimethyl-1,3-dioxolane, and cyclopentanone ethylene ketal in the gas phase. Combined experimental and DFT study

Rosas, Felix,Lezama, Jesus,Mora, Jose R.,Maldonado, Alexis,Chuchani, Gabriel,Cordova, Tania

, p. 9228 - 9237,10 (2012)

The kinetics of the gas-phase thermal decomposition of 2-methyl-1,3- dioxolane, 2,2-dimethyl-1,3-dioxolane, and cyclopentanone ethylene ketal were determined in a static system and the reaction vessel deactivated with allyl bromide. The decomposition reactions, in the presence of the free radical suppressor propene, are homogeneous, are unimolecular, and follow first-order law kinetics. The products of these reactions are acetaldehyde and the corresponding ketone. The working temperature range was 459-490 °C, and the pressure range was 46-113 Torr. The rate coefficients are given by the following Arrhenius equations: for 2-methyl-1,3-dioxolane, log k = (13.61 ± 0.12) - (242.1 ± 1.0)(2.303RT)-1, r = 0.9997; for 2,2-dimethyl-1,3-dioxolane, log k = (14.16 ± 0.14) - (253.7 ± 2.0)(2.303RT)-1, r = 0.9998; for cyclopentanone ethylene ketal, log k = (14.16 ± 0.14) - (253.7 ± 2.0)(2.303RT)-1, r = 0.9998. Electronic structure calculations using DFT methods B3LYP and MPW1PW91 with 6-31G(d,p), and 6-31++G(d,p) basis sets suggest that the decomposition of these substrates takes place through a stepwise mechanism. The rate-determining step proceeds through a concerted nonsynchronous four-centered cyclic transition state, and the elongation of the C-OCH3 bond in the direction C αδ+...OCH3δ- is predominant. The intermediate products of these decompositions are unstable, at the working temperatures, decomposing rapidly through a concerted cyclic six-centered cyclic transition state type of mechanism.

Regeneration of aldehydes and ketones from oximes using bis(trimethylsilyl)chromate

Lee,Kwak,Hwang

, p. 2425 - 2429 (1992)

Bis(trimethylsilyl) chromate transforms oximes of not only ketones but also aldehydes and 1,2-diketones to the corresponding carbonyl compounds, in high yields.

Catalytic oxidation of cycloalkanes by porphyrin cobalt(II) through efficient utilization of oxidation intermediates

Shen, Hai M.,Wang, Xiong,Guo, A. Bing,Zhang, Long,She, Yuan B.

, p. 1166 - 1173 (2020)

The catalytic oxidation of cycloalkanes using molecular oxygen employing porphyrin cobalt(II) as catalyst was enhanced through use of cycloalkyl hydroperoxides, which are the primary intermediates in oxidation of cycloalkanes, as additional oxidants to further oxidize cycloalkanes in the presence of porphyrin copper(II), especially for cyclohexane, for which the selectivity was enhanced from 88.6 to 97.2% to the KA oil; at the same time, the conversion of cyclohexane was enhanced from 3.88 to 4.41%. The enhanced efficiency and selectivity were mainly attributed to the avoided autoxidation of cycloalkanes and efficient utilization of oxidation intermediate cycloalkyl hydroperoxides as additional oxidants instead of conventional thermal decomposition. In addition to cyclohexane, the protocol presented in this research is also very applicable in the oxidation of other cycloalkanes such as cyclooctane, cycloheptane and cyclopentane, and can serve as a applicable and efficient strategy to boost the conversion and selectivity simultaneously in oxidation of alkanes. This work also is a very important reference for the extensive application of metalloporphyrins in catalysis chemistry.

Mild homogeneous oxidation and hydrocarboxylation of cycloalkanes catalyzed by novel dicopper(II) aminoalcohol-driven cores

Fernandes, Tiago A.,André, Vania,Kirillov, Alexander M.,Kirillova, Marina V.

, p. 357 - 367 (2017)

N-benzylethanolamine (Hbea) and triisopropanolamine (H3tipa) were applied as unexplored aminoalcohol N,O-building blocks for the self-assembly generation of two novel dicopper(II) compounds, [Cu2(μ-bea)2(Hbea)2](NO3)2 (1) and [Cu2(H3tipa)2(μ-pma)]·7H2O (2) {H4pma = pyromellitic acid}. These were isolated as stable and aqua-soluble microcrystalline products and were fully characterized by IR spectroscopy, ESI–MS(±), and single-crystal X-ray diffraction, the latter revealing distinct Cu2 cores containing the five-coordinate copper(II) centers with the {CuN2O3} or {CuNO4} environments. Compounds 1 and 2 were used as homogeneous catalysts for the mild oxidation of C5–C8 cycloalkanes to give the corresponding cyclic alcohols and ketones in up to 23% overall yields based on cycloalkane. The reactions proceed in aqueous acetonitrile medium at 50 °C using H2O2 as an oxidant. The effects of different reaction conditions were studied, including the type and loading of catalyst, amount and kind of acid promoter, and water concentration. Despite the fact that different acids (HNO3, H2SO4, HCl, or CF3COOH) promote the oxidation of alkanes, the reaction is exceptionally fast in the presence of a catalytic amount of HCl, resulting in the TOF values of up to 430 h?1. Although water typically strongly inhibits alkane oxidations due to the reduction of H2O2 concentration and lowering of the alkane solubility, in the systems comprising 1 and 2 we observed a significant growth (up to 5-fold) of an initial reaction rate in the cyclohexane oxidation on increasing the amount of H2O in the reaction mixture. The bond-, regio- and stereo-selectivity parameters were investigated in oxidation of different linear, branched, and cyclic alkane substrates. Both compounds 1 and 2 also catalyze the hydrocarboxylation of C5–C8 cycloalkanes, by CO, K2S2O8, and H2O in a water/acetonitrile medium at 60 °C, to give the corresponding cycloalkanecarboxylic acids in up to 38% yields based on cycloalkanes.

Highly dispersed Co and Ni nanoparticles encapsulated in N-doped carbon nanotubes as efficient catalysts for the reduction of unsaturated oxygen compounds in aqueous phase

Gong, Wanbing,Chen, Chun,Zhang, Haimin,Wang, Guozhong,Zhao, Huijun

, p. 5506 - 5514 (2018)

N-Doped carbon nanotube-encapsulated metal nanoparticles are of great interest in heterogeneous catalysis owing to their improved mass transfer ability and superior stability. Herein, a facile one-pot pyrolysis approach using melamine as the carbon and nitrogen source was developed to fabricate metal nanoparticles embedded in bamboo-like N-doped carbon nanotubes (named as Co@NCNTs-600-800 and Ni@NCNTs-600-800). The optimized Co@NCNTs-600-800 catalyst exhibited outstanding activity in furfural (FAL) selective hydrogenation to furfuryl alcohol (FOL) or cyclopentanone (CPO) in aqueous media. High yields of FOL (100%) and CPO (75.3%) were achieved at 80 °C and 140 °C, respectively. Besides, this cobalt catalyst showed very good stability and recyclability during the reaction. The synergistic effect between metallic cobalt and N-doped carbon nanotubes was systematically investigated. In addition, the as-prepared Ni@NCNTs-600-800 catalyst also exhibited remarkable activity. Under optimal conditions (100 °C and 4 MPa H2 pressure), a maximum tetrahydrofurfuryl alcohol (THFOL) yield (99.5%) was obtained in the aqueous-phase hydrogenation of FAL. The research thus highlights new perspectives for non-noble metal-based N-doped carbon nanotube catalysts for biomass transformation.

Solvent and substituent effects on the thermolysis of antimalarial fluorophenyl substituted 1,2.4-trioxanes

Cafferata, Lazaro F. R.,Rimada, Ruben S.

, p. 655 - 662 (2003)

The kinetics and mechanism of the thermal decomposition reaction of cis-6-(4-fluoropheny1)-5,6-[2-(4-fluorophenyl)-propylidene]-3, 3-tetramethylene-1,2,4-trioxacyclo-hexane (I) were investigated separately in n-hexane and in methanol solutions over the te

Dehydration of 1,5-Pentanediol over Na-Doped CeO2 Catalysts

Gnanamani, Muthu Kumaran,Jacobs, Gary,Martinelli, Michela,Shafer, Wilson D.,Hopps, Shelley D.,Thomas, Gerald A.,Davis, Burtron H.

, p. 1148 - 1154 (2018)

The effects of CeO2 doped with Na on the dehydration of 1,5-pentanediol were studied by using a fixed-bed reactor at two different temperatures (350 and 400 °C) and atmospheric pressure. For characterization, BET surface area, hydrogen temperature-programmed reduction, CO2 temperature-programmed desorption, and diffuse reflectance infrared Fourier transform spectroscopy techniques were utilized. The conversion of the diol on CeO2 was found to depend on Na loading. The selectivity to the desired product (i.e., unsaturated alcohol) increased and the selectivity to undesired products (i.e., tetrahydropyran, tetrahydropyran-2-one, cyclopentanol and cylopentanone) decreased with increasing Na content on CeO2. The basicity of hydroxyl groups or surface oxygen on CeO2 was altered with the addition of Na, and controlled the dehydration reaction pathway.

Hydrogenolysis of Furfuryl Alcohol to 1,2-Pentanediol Over Supported Ruthenium Catalysts

Yamaguchi, Aritomo,Murakami, Yuka,Imura, Tomohiro,Wakita, Kazuaki

, p. 731 - 736 (2021)

Hydrogenolysis of the furan rings of furfural and furfuryl alcohol, which can be obtained from biomass, has attracted attention as a method for obtaining valuable chemicals such as 1,2-pentanediol. In this study, we examined the hydrogenolysis of furfuryl alcohol to 1,2-pentanediol over Pd/C, Pt/C, Rh/C, and various supported Ru catalysts in several solvents. In particular, we investigated the effects of combinations of solvents and supports on the reaction outcome. Of all the tested combinations, Ru/MgO in water gave the best selectivity for 1,2-pentanediol: with this catalyst, 42 % selectivity for 1,2-pentanediol was achieved upon hydrogenolysis of furfuryl alcohol for 1 h at 463 K. In contrast, reaction in water in the presence of Ru/Al2O3 afforded cyclopentanone and cyclopentanol by means of hydrogenation and rearrangement reactions.

-

Liberman et al.

, (1972)

-

Highly selective hydrogenation of furfural to tetrahydrofurfuryl alcohol over MIL-101(Cr)-NH2 supported Pd catalyst at low temperature

Yin, Dongdong,Ren, Hangxing,Li, Chuang,Liu, Jinxuan,Liang, Changhai

, p. 319 - 326 (2018)

An efficient heterogeneous catalyst, Pd@MIL-101(Cr)-NH2, is prepared through a direct pathway of anionic exchange followed by hydrogen reduction with amino-containing MIL-101 as the host matrix. The composite is thermally stable up to 350 °C and the Pd nanoparticles uniformly disperse on the matal organic framework (MOF) support, which are attributed to the presence of the amino groups in the frameworks of MIL-101(Cr)-NH2. The selective hydrogenation of biomass-based furfural to tetrahydrofurfuryl alcohol is investigated by using this multifunctional catalyst Pd@MIL-101(Cr)-NH2 in water media. A complete hydrogenation of furfural is achieved at a low temperature of 40 °C with the selectivity of tetrahydrofurfuryl alcohol close to 100%. The amine-functionalized MOF improves the hydrogen bonding interactions between the intermediate furfuryl alcohol and the support, which is conducive for the further hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol in good coordination with the metal sites.

Hydrogenation of Furfural to Cyclopentanone under Mild Conditions by a Structure-Optimized Ni?NiO/TiO2 Heterojunction Catalyst

Chen, Shuo,Qian, Ting-Ting,Ling, Li-Li,Zhang, Wenhua,Gong, Bing-Bing,Jiang, Hong

, p. 5507 - 5515 (2020)

The catalytic conversion of biomass-derived furfural (FFA) into cyclopentanone (CPO) in aqueous solution is an important pathway to obtain sustainable resources. However, the conversion and selectivity under mild conditions are still unsatisfactory. In this study, a catalyst consisting of Ni?NiO heterojunction supported on TiO2 with optimized composition of anatase and rutile (Ni?NiO/TiO2-Re450) is prepared by pyrolysis at 450 °C. With Ni?NiO/TiO2-Re450, as catalyst, complete conversion of FFA and 87.4 % yield of CPO are achieved under mild reaction conditions (1 MPa, 140 °C, 6 h). 95.4 % FFA conversion is retained up to the fifth run, indicating the high stability of the catalyst. Multiple characterizations, control experiments, and theoretical calculations demonstrate that the good catalytic performance of Ni?NiO/TiO2-Re450 can be attributed to a synergistic effect of the Ni?NiO heterojunction and the TiO2 support. This low-cost catalyst may expedite the catalytic upgrading and practical application of biomass-derived chemicals.

Catalytic hydrogenation of furfural to tetrahydrofurfuryl alcohol using competitive nickel catalysts supported on mesoporous clays

Sunyol,English Owen,González,Salagre,Cesteros

, (2021)

Nickel catalysts supported on mesoporous clays with different acid properties, such as montmorillonite MK-10, Al-pillared montmorillonite, mesoporous Na-saponite and mesoporous H-saponite, were prepared, characterized and tested for the hydrogenation of furfural to tetrahydrofurfuryl alcohol (THFA). Clays were also modified introducing basicity through magnesium oxide in different amounts. Catalysts with higher acidity or low amounts of metallic centres favoured deactivation and/or selectivity to the non-desired products. Interestingly, the addition of MgO both neutralized the acidity of the montmorillonite supports and improved the hydrogenation of the furanic ring, resulting in higher selectivity to THFA. The best catalyst was the one prepared with montmorillonite MK-10 covered by 30 wt% of magnesium oxide and with 8.8 % of the Ni metal phase achieving total conversion and total selectivity to THFA. The activity of this catalyst was maintained after several reuses.

-

Marsh,Hermes

, p. 4506 (1964)

-

Ruthenium Trichloride Catalyst in Water: Ru Colloids versus Ru Dimer Characterization Investigations

Lebedeva, Anastasia,Albuquerque, Brunno L.,Domingos, Josiel B.,Lamonier, Jean-Fran?ois,Giraudon, Jean-Marc,Lecante, Pierre,Denicourt-Nowicki, Audrey,Roucoux, Alain

, p. 4141 - 4151 (2019)

An easy-to-prepare ruthenium catalyst obtained from ruthenium(III) trichloride in water demonstrates efficient performances in the oxidation of several cycloalkanes with high selectivity toward the ketone. In this work, several physicochemical techniques were used to demonstrate the real nature of the ruthenium salt still unknown in water and to define the active species for this Csp3-H bond functionalization. From transmission electron microscopy analyses corroborated by SAXS analyses, spherical nanoobjects were observed with an average diameter of 1.75 nm, thus being in favor of the formation of reduced species. However, further investigations, based on X-ray scattering and absorption analyses, showed no evidence of the presence of a metallic Ru-Ru bond, proof of zerovalent nanoparticles, but the existence of Ru-O and Ru-Cl bonds, and thus the formation of a water-soluble complex. The EXAFS (extended X-ray absorption fine structure) spectra revealed the presence of an oxygen-bridged diruthenium complex [Ru(OH)xCl3-x]2(μ-O) with a high oxidation state in agreement with catalytic results. This study constitutes a significant advance to determine the true nature of the RuCl3·3H2O salt in water and proves once again the invasive nature of the electron beam in microscopy experiments, routinely used in nanochemistry.

Identification, characterization, and application of three enoate reductases from Pseudomonas putida in in vitro enzyme cascade reactions

Peters, Christin,Koelzsch, Regina,Kadow, Maria,Skalden, Lilly,Rudroff, Florian,Mihovilovic, Marko D.,Bornscheuer, Uwe T.

, p. 1021 - 1027 (2014)

Enoate reductases are versatile enzymes for the enantio- and regioselective addition of hydrogen to double bonds. We identified three EREDs (XenA, XenB, NemA) from Pseudomonas putida ATCC 17453 through a sequence motif search. In addition to cloning, functional expression, and biochemical characterization of these enzymes, the enoate reductases were also applied in enzyme cascade reactions in combination with a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase to produce lactones. Good things come in threes: The identification, cloning, expression, and characterization of three enoate reductases from Pseudomonas putida reveal broad substrate scope and high stereoselectivities. Furthermore, the enoate reductases could be integrated into cascade reactions together with an alcohol dehydrogenase and a Baeyer-Villiger monooxygenase.

Simultaneous Upgrading of Furanics and Phenolics through Hydroxyalkylation/Aldol Condensation Reactions

Bui, Tuong V.,Sooknoi, Tawan,Resasco, Daniel E.

, p. 1631 - 1639 (2017)

The simultaneous conversion of cyclopentanone and m-cresol has been investigated on a series of solid-acid catalysts. Both compounds are representative of biomass-derived streams. Cyclopentanone can be readily obtained from sugar-derived furfurals through Piancatelli rearrangement under reducing conditions. Cresol represents a family of phenolic compounds, typically obtained from the depolymerization of lignin. In the first biomass conversion strategy proposed here, furfural is converted in high yields and selectivity to cyclopentanone (CPO) over metal catalysts such as Pd-Fe/SiO2 at 600 psi (~4.14 MPa) H2 and 150 °C. Subsequently, CPO and cresol are further converted through acid-catalyzed hydroxyalkylation. This C?C coupling reaction may be used to generate products in the molecular weight range that is appropriate for transportation fuels. As molecules beyond this range may be undesirable for fuel production, a catalyst with a suitable porous structure may be advantageous for controlling the product distribution in the desirable range. If Amberlyst resins were used as a catalyst, C12–C24 products were obtained whereas when zeolites with smaller pore sizes were used, they selectively produced C10 products. Alternatively, CPO can undergo the acid-catalyzed self-aldol condensation to form C10 bicyclic adducts. As an illustration of the potential for practical implementation of this strategy for biofuel production, the long-chain oxygenates obtained from hydroxyalkylation/aldol condensation were successfully upgraded through hydrodeoxygenation to a mixture of linear alkanes and saturated cyclic hydrocarbons, which in practice would be direct drop-in components for transportation fuels. Aqueous acidic environments, which are typically encountered during the liquid-phase upgrading of bio-oils, would inhibit the efficiency of base-catalyzed processes. Therefore, the proposed acid-catalyzed upgrading strategy is advantageous for biomass conversion in terms of process simplicity.

-

Brown,Ritchie

, p. 2007 (1968)

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Effect of Ni Metal Content on Emulsifying Properties of Ni/CNTox Catalysts for Catalytic Conversion of Furfural in Pickering Emulsions

Herrera,Pinto-Neira,Fuentealba,Sepúlveda,Rosenkranz,García-Fierro,González,Escalona

, p. 682 - 694 (2021)

Ni/CNTox catalysts with variable metal content have been prepared to investigate their emulsifying and catalytic properties for the liquid-phase conversion of furfural. The solid catalysts and emulsions were analyzed by several characterization techniques. The catalytic activity linearly increased with increasing Ni content (up to 10 wt.%) before dropping down again for a Ni content of 15 wt.%. The loss of catalytic activity was attributed to larger emulsion droplets formed by the inhibition of hydrophilic sites. All Ni/CNTox catalysts were highly selective to cyclopentanone as a main product, while several changes regarding secondary products were observed. Ni/CNTox catalysts with a Ni content up to 10 wt.% favor the formation of levulinic acid, while catalysts with a Ni content of 15 wt.% were selective to tetrahydrofurfuryl alcohol. This was attributed to an inhibition of the acid sites thus favoring the catalyst's hydrogenation capacity.

Aqueous phase hydrogenation of furfural to furfuryl alcohol over Pd-Cu catalysts

Fulajtárova, Katarína,Soták, Tomá?,Hronec, Milan,Vávra, Ivo,Dobro?ka, Edmund,Omastová, Mária

, p. 78 - 85 (2015)

A series of Pd, Cu and bimetallic Pd-Cu catalysts with different metals loadings on various supports were prepared for the selective hydrogenation of furfural to furfuryl alcohol in water as a solvent. In the literature are almost missing the data about the selective hydrogenation of furfural in water. Among the catalysts screened, bimetallic Pd-Cu catalysts supported on MgO and Mg(OH)2 prepared by electroless plating method showed the highest conversion and selectivity to furfuryl alcohol. The catalysts 5% Pd-5% Cu supported on MgO or Mg(OH)2 exhibited at 110°C and 0.6 MPa of hydrogen complete conversion of furfural and higher than 98% selectivity toward furfuryl alcohol after 80 min of reaction. The complete conversion of furfural and the same selectivity could be achieved after five catalytic cycles without extra catalyst treatment or reactivation. Based on physico-chemical characterization the role of Cu loading on the performance of bimetallic Pd-Cu catalysts was discussed. We assume that over Pd-Cu catalyst prepared by electroless plating method on the surface are present monometallic Pd0 sites and closely interacting bimetallic Pd0-Cu2O catalytic sites. The Cu+ sites participate on activation of CO group in furfural. The interaction between active metal species and the support also influence the performance of catalyst.

Wacker-type oxidation of cyclopentene under dioxygen atmosphere catalyzed by Pd(OAc)2/NPMoV on activated carbon

Kishi, Arata,Higashino, Takashi,Sakaguchi, Satoshi,Ishii, Yasutaka

, p. 99 - 102 (2000)

Wacker-type oxidation of cyclopentene to cyclopentanone under dioxygen atmosphere was successfully achieved by the use of Pd(OAc)2 and molybdovanadophosphate supported on activated carbon, [Pd(OAc)2-NPMoV/C], catalyst. Thus, the reaction of cyclopentene under O2 (1 atm) in aqueous acetonitrile acidified by CH3SO3H in the presence of [Pd(OAc)2-NPMoV/C] at 50°C produced cyclopentanone in 85% yield along with a small amount of cyclopentenone (1%).

One-Step Encapsulation of Bimetallic Pd–Co Nanoparticles Within UiO-66 for Selective Conversion of Furfural to Cyclopentanone

Wang, Yanling,Liu, Cun,Zhang, Xiongfu

, p. 2158 - 2166 (2020)

Abstract: The design of efficient catalysts is of important significance for the transformation of biomass into chemicals. In this work, bimetallic Pd–Co nanoparticles were encapsulated within UiO-66 to form a core–shell Pd–Co@UiO-66 catalyst via a facile one-step strategy. The as-synthesized Pd–Co@UiO-66 catalysts were characterized and applied to the selective hydrogenation of furfural (FUR) to cyclopentanone (CPO). Compared with the monometallic Pd@UiO-66, the Pd–Co@UiO-66 could demonstrate excellent performance with 96% CPO selectivity and 99% FUR conversion at 120?°C under 3?MPa H2 pressure for 12?h. It was found that trace Co had synergetic and promoting effects on the catalytic performance. The core–shell catalysts showed more outstanding recyclability than the supported catalysts, which could maintain high CPO yield after 5th runs. Graphic Abstract: [Figure not available: see fulltext.].

Characterization and reactivity of γ-Al2O3 supported Pd-Cu bimetallic nanocatalysts for the selective oxygenization of cyclopentene

Liu, Wei-Wei,Feng, Yi-Si,Wang, Guang-Yu,Jiang, Wei-Wei,Xu, Hua-Jian

, p. 905 - 909 (2016)

In this work, Pd-Cu/γ-Al2O3 is prepared by the impregnation method and investigated for selective oxygenization of cyclopentene to cyclopentanone. A series of bimetallic Pd-Cu/γ-Al2O3 nanocatalysts were prepared and the structures characterized by XRD, XPS and TEM. We determined that the obtained Pd-Cu/γ-Al2O3 (molar ratio Pd:Cu = 5:1) was an efficient catalyst for the oxygenization of cyclopentene to cyclopentanone with >95% selectivity and >85% conversion (100 °C, 1 MPa initial O2 pressure, 7 h).

Conversion of furfural to cyclopentanol on Cu/Zn/Al catalysts derived from hydrotalcite-like materials

Wang, Yuan,Zhou, Minghao,Wang, Tongzhen,Xiao, Guomin

, p. 1557 - 1565 (2015)

The Cu/Zn/Al catalysts, prepared from the calcination and reduction of hydrotalcite-like compounds containing Cu, Zn and Al, were introduced to the aqueousphase hydrogenation of furfural from pyrolysis of biomass. And the target production was cyclopentanol. The catalyst performance was investigated from the aspects of catalyst composition, calcination temperature, reaction temperature, initial hydrogen pressure and reaction time. Among all the variables, calcination temperature had a profound impact on the catalyst performance. The furfural conversion was up to nearly 100 % with a cyclopentanol yield of 84 %, when the hydrogenation reaction was carried out over 600 °C calcined hydrotalcite catalyst with a Cu/Zn/Al molar ratio of 6:9:5 at 150 °C with an initial hydrogen pressure of 4 MPa for 10 h. The features of Cu/Zn/Al catalysts were investigated via XRD, XPS, TPR, SEM and BET.

Influence of furanic polymers on selectivity of furfural rearrangement to cyclopentanone

Hronec, Milan,Fulajtárova, Katarina,Mi?u?ik, Matej

, p. 426 - 431 (2013)

The influence of furanic polymers upon the activity and selectivity of Ni, Pd, Pt catalysts in rearrangement of furfural to cyclopentanone, and its consecutive hydrogenation to cyclopentanol in an aqueous phase has been studied. The coverage of surface of

Sorption and catalysis by robust microporous metalloporphyrin framework solids

Smithenry, Dennis W.,Wilson, Scott R.,Nakagaki, Shirley,Suslick, Kenneth S.

, p. 857 - 869 (2017)

Two isostructural metalloporphyrin framework solids have been synthesized. Both frameworks contains manganese(III) metal complexes of trans-dicarboxylateporphyrins whose peripheralcarboxylates coordinate the edges of tetrahedral Zn4O+6 clusters; the two metalloporphyrins explored are Mn(III) and Co(II). The cubic interpenetrated frameworks have 72% free volume and 4 × 7 ? averaged size pores. The evacuated frameworks are robust and retain a structure open to the sorption of substrates with medium polarity. The manganese porphyrin framework catalyzes the hydroxylation of cyclic and linear alkanes with iodosylbenzene as oxidant in a size-and polarity-selective manner. In addition, the catalysis was found to occur within the pores, making this a rare case of porphyrin framework solid with interior catalysis.

Novel Technique for the Generation of Bis(polyfluoroalkyl) and Polyfluoroalkyl Nitroalkyl Nitroxides. ESR Verification of Mechanistic Propositions for the Reactions between Polyfluorodiacyl Peroxides and Carbanions Derived from Secondary Nitroalkanes

Zhao, Cheng-Xue,Jiang, Xi-Kui,Chen, Guo-Fei,Qu, Yan-Ling,Wang, Xian-Shan,Lu, Jian-Ying

, p. 3132 - 3133 (1986)

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Reductive Elimination of Ketones from Ruthenium(II) Complexes

Saunders, David R.,Mawby, Roger J.

, p. 2133 - 2136 (1984)

Complexes (R = aryl or alkyl) decompose at room temperature in CHCl3 or Me2CO solution to yield the ketones R2CO.Decomposition is intramolecular, since the complexes yield only the unsymmetrical ketones RR'CO, and the disappearance of follows simple first-order kinetics.The acyl complex also decomposes in CHCl3 solution to give (4-MeC6H4)2CO, but the decomposition is inhibited by free Me3CNC.It is believed that the ketones are formed by reductive elimination from .A ruthenium(0) product could not be isolated, but the ruthenium(II) complex Ru(CO)ClC6H4Me>(PMe2Ph)2> was obtained when the decomposition of in CHCl3 was carried out at higher temperatures.

-

Liberman et al.

, (1971)

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Catalytic Allylation of 1-Trimethylsilyloxycyclopent-1-ene into 2-Allylcyclopentanone over Palladium supported on Silica

Baba, T.,Nakano, K.,Nishiyama, S.,Tsurya, S.,Masai, M.

, p. 348 - 349 (1990)

1-Trimethylsilyloxycyclopent-1-ene can be catalytically converted into 2-allylcyclopentanone by its reaction with diallyl carbonate over palladium supported on silica.

A one-pot synthesis of 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane by hydrodeoxygenation of xylose using a palladium catalyst

Jackson, Michael A.,Blackburn, Judith A.,Price, Neil P.J.,Vermillion, Karl E.,Peterson, Steven C.,Ferrence, Gregory M.

, p. 9 - 16 (2016)

In an effort to expand the number of biobased chemicals available from sugars, xylose has been converted to 1,6,9,13-tetraoxadispiro(4.2.4.2)tetradecane in a one-pot reaction using palladium supported on silica-alumina as the catalyst. The title compound is produced in 35-40% yield under 7 MPa H2 pressure at 733 K using 3-10 wt%Pd on silica-alumina catalyst. It is isolated using a combination of liquid-liquid extractions and flash chromatography. This dimer can be converted to its monomer, 2-hydroxy-(2-hydroxymethyl)tetrahydrofuran, which ring opens under acid conditions to 1,5-dihydroxy-2-pentanone. This diol can then be esterified with vinylacetate in phosphate buffer to produce 1,5-bis(acetyloxy)-2-pentanone which is an inhibitor of mammalian 11β-hydroxysteroid dehydrogenase 1. 1H and 13C nmr spectra of each of these species are reported. The single crystal X-ray structure of the title compound is also reported. These data were collected in a temperature range of 100 K-273 K and show a solid state phase change from triclinic to monoclinic between 175 K and 220 K without a conformational change.

Copper(II) Coordination Polymers Self-Assembled from Aminoalcohols and Pyromellitic Acid: Highly Active Precatalysts for the Mild Water-Promoted Oxidation of Alkanes

Fernandes, Tiago A.,Santos, Carla I. M.,André, Vania,K?ak, Julia,Kirillova, Marina V.,Kirillov, Alexander M.

, p. 125 - 135 (2016)

Three novel water-soluble 2D copper(II) coordination polymersˉ[{Cu2(μ2-dmea)2(H2O)}2(μ4-pma)]n·4nH2O (1), [{Cu2(μ2-Hedea)2}2(μ4-pma)]n·4nH2O (2), and [{Cu(bea)(Hbea)}4(μ4-pma)]n·2nH2O (3)ˉwere generated by an aqueous medium self-assembly method from copper(II) nitrate, pyromellitic acid (H4pma), and different aminoalcohols [N,N-dimethylethanolamine (Hdmea), N-ethyldiethanolamine (H2edea), and N-benzylethanolamine (Hbea)]. Compounds 2 and 3 represent the first coordination polymers derived from H2edea and Hbea. All the products were characterized by infrared (IR), electron paramagnetic resonance (EPR), and ultraviolet-visible light (UV-vis) spectroscopy, electrospray ionization-mass spectroscopy (ESI-MS(±)), thermogravimetric and elemental analysis, and single-crystal X-ray diffraction (XRD), which revealed that their two-dimensional (2D) metal-organic networks are composed of distinct dicopper(II) or monocopper(II) aminoalcoholate units and μ4-pyromellitate spacers. From the topological viewpoint, the underlying 2D nets of 1-3 can be classified as uninodal 4-connected layers with the sql topology. The structures of 1 and 2 are further extended by multiple intermolecular hydrogen bonds, resulting in three-dimensional (3D) hydrogen-bonded networks with rare or unique topologies. The obtained compounds also act as highly efficient precatalysts for the mild homogeneous oxidation, by aqueous H2O2 in acidic MeCN/H2O medium, of various cycloalkanes to the corresponding alcohols and ketones. Overall product yields up to 45% (based on cycloalkane) were attained and the effects of various reaction parameters were investigated, including the type of precatalyst and acid promoter, influence of water, and substrate scope. Although water usually strongly inhibits the alkane oxidations, a very pronounced promoting behavior of H2O was detected when using the precatalyst 1, resulting in a 15-fold growth of an initial reaction rate in the cyclohexane oxidation on increasing the amount of H2O from ~4 M to 17 M in the reaction mixture, followed by a 2-fold product yield growth.

Aqueous phase hydrogenation of furfural to tetrahydrofurfuryl alcohol on alkaline earth metal modified Ni/Al2O3

Yang, Yanliang,Ma, Jiping,Jia, Xiuquan,Du, Zhongtian,Duan, Ying,Xu, Jie

, p. 51221 - 51228 (2016)

Al2O3 modified by alkaline earth metals M-Al2O3 (M = Mg, Ca, Sr, Ba) was synthesised by coprecipitation method. The nickel-based catalysts supported by M-Al2O3 were prepared by impregnation method. The catalysts were characterized by TEM, N2 adsorption/desorption, XRD, H2-TPR, NH3-TPD and XPS, and used for the direct hydrogenation of furfural to tetrahydrofurfuryl alcohol (THFA) in water. The reaction was demonstrated to proceed through furfuryl alcohol as an intermediate. The modification of Al2O3 by alkaline earth metals has a significant effect on the activity and selectivity of THFA. A high yield of THFA was obtained over Ni/Ba-Al2O3 under optimized conditions. Moreover, the catalyst is recyclable and reusable at least four times without significant loss of the conversion of furfural and selectivity of THFA.

Greener selective cycloalkane oxidations with hydrogen peroxide catalyzed by copper-5-(4-pyridyl)tetrazolate metal-organic frameworks

Martins, Luísa,Nasani, Rajendar,Saha, Manideepa,Mobin, Shaikh,Mukhopadhyay, Suman,Pombeiro, Armando

, p. 19203 - 19220 (2015)

Microwave assisted synthesis of the Cu(I) compound [Cu(μ4-4-ptz)]n [1, 4-ptz = 5-(4-pyridyl)tetrazolate] has been performed by employing a relatively easy method and within a shorter period of time compared to its sister compounds. The syntheses of the Cu(II) compounds [Cu3(μ3-4-ptz)4(μ2-N3)2(DMF)2]n·(DMF)2n (2) and [Cu(μ2-4-ptz)2(H2O)2]n (3) using a similar method were reported previously by us. MOFs 1-3 revealed high catalytic activity toward oxidation of cyclic alkanes (cyclopentane, -hexane and -octane) with aqueous hydrogen peroxide, under very mild conditions (at room temperature), without any added solvent or additive. The most efficient system (2/H2O2) showed, for the oxidation of cyclohexane, a turnover number (TON) of 396 (TOF of 40 h?1), with an overall product yield (cyclohexanol and cyclohexanone) of 40% relative to the substrate. Moreover, the heterogeneous catalytic systems 1-3 allowed an easy catalyst recovery and reuse, at least for four consecutive cycles, maintaining ca. 90% of the initial high activity and concomitant high selectivity.

Synthesis of azasilacyclopentenes and silanols: Via Huisgen cycloaddition-initiated C-H bond insertion cascades

Shih, Jiun-Le,Jansone-Popova, Santa,Huynh, Christopher,May, Jeremy A.

, p. 7132 - 7137 (2017)

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C-H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C-H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.

-

Nelson et al.

, p. 1580 (1971)

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Selective reduction of α,β-unsaturated aldehydes and ketones to allylic alcohols with diisobutylalkoxyalanes

Cha, Jin Soon,Kwon, Oh Oun,Kwon, Sang Yong

, p. 355 - 360 (1996)

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Selective transformation of furfural to cyclopentanone

Hronec, Milan,Fulajtarová, Katarina

, p. 100 - 104 (2012)

An entirely new route for highly selective preparation of cyclopentanone from furfural is described. It has been found that furfural dissolved in water is converted to cyclopentanone with very high selectivity at temperatures above 140 °C and hydrogen pressures > 30 bar. The selectivity of this reaction is strongly influenced by the heterogeneous catalyst and depends on the reaction conditions. Prolongation of the reaction time leads to the hydrogenation of cyclopentanone to cyclopentanol. If instead of water other solvents are used, the main products of reaction are well known hydrogenated derivatives of furfural, i.e. furfuryl alcohol, tetrahydrofurfuryl alcohol, 2-methylfuran and 2-methyltetrahydrofuran. In the presence of 5% Pt/C catalyst, 76.50 mol% yield of cyclopentanone (81.32 mol% comprehensive yield of cyclopentanone and cyclopentanol) is obtained after 30 min of reaction at 160 °C and a hydrogen pressure of 80 bar.

Hydrogenative Ring-Rearrangement of Biobased Furanic Aldehydes to Cyclopentanone Compounds over Pd/Pyrochlore by Introducing Oxygen Vacancies

Deng, Qiang,Deng, Shuguang,Gao, Rui,Li, Xiang,Wang, Jun,Zeng, Zheling,Zou, Ji-Jun

, p. 7355 - 7366 (2020)

Upgrading furanic aldehydes (such as furfural or 5-hydroxymethyl furfural) to cyclopentanone compounds (such as cyclopentanone or 3-hydroxymethyl cyclopentanone) is of great significance for the synthesis of high-value chemicals and biomass utilization. Developing an efficient reduced metal/acidic support with Lewis acidity is the key to facilitating the carbonyl hydrogenation and hydrolysis steps in the hydrogenative ring-rearrangement reaction. Herein, three pure Lewis acidic pyrochlore supports of the form A2B2O7 (La2Sn2O7, Y2Sn2O7, and Y2(Sn0.7Ce0.3)2O7-δ) with the same crystal structures and different metals are synthesized. The Lewis acidity and the surface properties of the pyrochlore can be tuned by inserting different kinds of A and B site metals. After impregnation, Pd nanoparticles with appropriate particle sizes are uniformly loaded on the surface of pyrochlore. For the reaction of the furanic aldehydes, all of these pyrochlore-based catalysts exhibit hydrogenation and hydrolysis rates that are both faster than those of traditional support-based catalysts due to the oxygen vacancy and pure Lewis acidity of the support. Among these pyrochlore-based catalysts, Pd/Y2Sn2O7 exhibits activity and selectivity that are higher than those of Pd/La2Sn2O7. Moreover, the Y2Sn2O7-based catalyst partially substituted by Ce3+ ions at the B site is more efficient, with the highest cyclopentanone yield and 3-hydroxymethyl cyclopentanone yield of 95.0percent and 92.5percent, respectively. Furthermore, the catalyst can still maintain an effective activity and stability after 4 runs. This study not only presents an efficient biobased route for the production of cyclopentanone compounds but also focuses on the acid catalytic performance of pyrochlore based on its pure Lewis acidity.

Self-assembled two-dimensional water-soluble dipicolinate Cu/Na coordination polymer: Structural features and catalytic activity for the mild peroxidative oxidation of cycloalkanes in acid-free medium

Kirillova, Marina V.,Kirillov, Alexander M.,Guedes Da Silva, M. Fatima C.,Pombeiro, Armando J. L.

, p. 3423 - 3427 (2008)

The new water-soluble 2D Cu/Na coordination polymer [Cu(μ-dipic) 2{Na2(μ-H2O)4}] n·2nH2O (1) has been synthesized by self-assembly in aqueous medium from copper(II) nitrate, dipicolinic acid (H2dipic) and sodium hydroxide in the presence of triethanolamine. It has been characterized by IR spectroscopy, FAB+-MS, elemental and single-crystal X-ray diffraction analyses, the latter featuring a layered 2D metal-organic structure that is extended to a 3D supramolecular assembly by extensive hydrogen bonding between adjacent layers and involving crystallization water molecules. Compound 1 has been shown to act as a catalyst precursor for the peroxidative oxidation of cyclohexane and cyclopentane to the corresponding cyclic ketones and alcohols by aqueous H2O2 in MeCN solution and in the absence of acid additives. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Production of cyclopentanone from furfural over Ru/C with Al11.6PO23.7 and application in the synthesis of diesel range alkanes

Shen, Tao,Hu, Ruijia,Zhu, Chenjie,Li, Ming,Zhuang, Wei,Tang, Chenglun,Ying, Hanjie

, p. 37993 - 38001 (2018)

The bio-based platform molecule furfural was converted to the high value chemical cyclopentanone over Ru/C (0.5?wt%) and Al11.6PO23.7 catalysts in good yield (84%) with water as the medium. After screening the reaction conditions, the selectivity for cyclopentanone and cyclopentanol could be controlled by adjusting the hydrogen pressure at the temperature of 433 K. Herein, we propose a new mechanism for the synergistic catalysis of a Bronsted acid and Lewis acid for the conversion of furfural to cyclopentanone through the cyclopentenone route, which is catalyzed by Ru/C and Al11.6PO23.7. In addition, based on cyclopentanone, higher octane number cyclic alkanes (>85% selectivity), which are used as hydrocarbon fuels, were synthesized via a C-C coupling reaction followed by hydrodeoxygenation.

Selective conversion of furfural to cyclopentanone or cyclopentanol using different preparation methods of Cu-Co catalysts

Li, Xing-Long,Deng, Jin,Shi, Jing,Pan, Tao,Yu,Xu, Hua-Jian,Fu, Yao

, p. 1038 - 1046 (2015)

Cu-Co catalysts, prepared by a co-precipitation method (CP) and an oxalate sol-gel method (OG), can selectively convert furfural (FFA) to cyclopentanone (CPO) or cyclopentanol (CPL), respectively. The conversion of FFA to CPO or CPL by Cu-Co catalysts were studied in aqueous solutions. We found that the product distribution was influenced by the catalyst support, Cu loading, calcination temperature, hydrogen pressure, the number of times the catalyst was reused and the preparation method of the catalyst. The surface morphology, surface area and composition of the catalysts were studied by XRD, XPS, BET, ICP-AES and TEM characterization. We found that there was a strong interaction between Cu and Co. Cu0, Cu2O and Co0 were the main active catalyst phases on the surfaces of the catalysts, but the amounts were different in the different catalysts. Cu0, Co0 and Cu2O were the active hydrogenation species, and Cu2O also played the role of an electrophile or Lewis acid to polarize the CO bond via lone pair electrons on the oxygen atom. According to XRD and XPS, the main phases on the surface of the CP catalysts were Cu0 and Cu2O. The hydrogenation activity of the CP catalyst was relatively weak and the main product was CPO. In contrast, the hydrogenation activity of the OG catalyst was high and the main product was the fully hydrogenated product CPL due to the main active phases of Co0 and Cu2O on the surface of the OG catalyst. At lower hydrogen pressure (2 MPa) and lower Cu loadings (2% for OG, 5% for CP), we obtained the highest yield of 67% CPO and 68% CPL, respectively. This journal is

Photoinduced reversible structural transformation and selective oxidation catalysis of unsaturated ruthenium complexes supported on SiO2

Tada, Mizuki,Akatsuka, Yusaku,Yang, Yong,Sasaki, Takehiko,Kinoshita, Mutsuo,Motokura, Ken,Iwasawa, Yasuhiro

, p. 9252 - 9255 (2008)

(Chemical Equation Presented) Ru experienced? Two novel coordinatively unsaturated SiO2-supported Ru complexes were prepared by photoinduced ligand elimination, accompanied by dissociative coordination of a surface OH group to the unsaturated Ru center by photoirradiation. Wavelength- and atmosphere-dependent photoinduced reversible interconversion occurs between the two Ru complexes. One of the complexes is catalytically active for the photooxidation of cycloalkanes with O2.

-

Liberman et al.

, (1971)

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An efficient method for the catalytic aerobic oxidation of cycloalkanes using 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI)

Guha, Samar K.,Ishii, Yasutaka

, p. 327 - 335 (2021/12/13)

N-Hydroxyphthalimide (NHPI) is known to be an effective catalyst for the oxidation of hydrocarbons. The catalytic activity of NHPI derivatives is generally increased by introducing an electron-withdrawing group on the benzene ring. In a previous report, two NHPI derivatives containing fluorinated alkyl chain were prepared and their catalytic activity was investigated in the oxidation of cycloalkanes. It was found that the fluorinated NHPI derivatives showed better yields for the oxidation reaction. As a continuation of our work with fluorinated NHPI derivatives, our next aim was to investigate the catalytic activity of the NHPI derivatives by introducing fluorine atoms in the benzene ring of NHPI. In the present research, 3,4,5,6-Tetrafluoro-N-Hydroxyphthalimide (F4-NHPI) is prepared and its catalytic activity has been investigated in the oxidation of two different cycloalkanes for the first time. It has been found that F4-NHPI showed higher catalytic efficiency compared with that of the parent NHPI catalyst in the present reactions. The presence of a fluorinated solvent and an additive was also found to accelerate the oxidation.

Solvent effect on the rate and direction of furfural transformations during hydrogenation over the Pd/C catalyst

Belskaya, O. B.,Likholobov, V. A.,Mironenko, R. M.

, p. 64 - 69 (2022/02/25)

The rate and directions of transformations during the liquid-phase hydrogenation of furfural with molecular hydrogen in the presence of the 5%Pd/C catalyst (at 423 K, 3 MPa) depend substantially on the chemical nature of the solvent. The main products of

Application of imidazole carbonate in preparation of chemical intermediate

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Paragraph 0036-0049, (2021/03/13)

The invention provides an application of an imidazole carbonate in preparation of a chemical intermediate cyclopentanone, which is characterized by comprising the following steps: placing cyclopentenein a reaction vessel, adding ionic liquid imidazole carbonate and a Wacker catalyst, introducing an oxygen source, stirring and heating to react at normal pressure, and carrying out after-treatment to obtain cyclopentanone. The ionic liquid imidazole carbonate is used as a solvent, the system can fully react without a high-pressure condition, the reaction time is greatly shortened, the high yieldand purity of the product can be ensured, the method is particularly suitable for industrial production, and an unexpected technical effect is achieved.

Green oxidation of amines by a novel cold-adapted monoamine oxidase mao p3 from psychrophilic fungi pseudogymnoascus sp. p3

Bia?kowska, Aneta M.,Jod?owska, Iga,Szymczak, Kamil,Twarda-Clapa, Aleksandra

supporting information, (2021/10/25)

The use of monoamine oxidases (MAOs) in amine oxidation is a great example of how biocatalysis can be applied in the agricultural or pharmaceutical industry and manufacturing of fine chemicals to make a shift from traditional chemical synthesis towards more sustainable green chemistry. This article reports the screening of fourteen Antarctic fungi strains for MAO activity and the discovery of a novel psychrozyme MAOP3 isolated from the Pseudogymnoascus sp. P3. The activity of the native enzyme was 1350 ± 10.5 U/L towards a primary (n-butylamine) amine, and 1470 ± 10.6 U/L towards a secondary (6,6-dimethyl-3-azabicyclohexane) amine. MAO P3 has the potential for applications in biotransformations due to its wide substrate specificity (aliphatic and cyclic amines, pyrrolidine derivatives). The psychrozyme operates at an optimal temperature of 30? C, retains 75% of activity at 20? C, and is rather thermolabile, which is beneficial for a reduction in the overall costs of a bioprocess and offers a convenient way of heat inactivation. The reported biocatalyst is the first psychrophilic MAO; its unique biochemical properties, substrate specificity, and effectiveness predispose MAO P3 for use in environmentally friendly, low-emission biotransformations.

Chromium-Catalyzed Production of Diols From Olefins

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Paragraph 0111, (2021/03/19)

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Process route upstream and downstream products

Process route

Cyclopentanol
96-41-3

Cyclopentanol

acetophenone
98-86-2

acetophenone

1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

cyclopentanone
120-92-3

cyclopentanone

Conditions
Conditions Yield
With potassium hydroxide; carbonylbis(trifluoroacetato)bis(triphenylphosphine)ruthenium; at 140 ℃; Equilibrium constant; Thermodynamic data; ΔG (gas);
potassium hydroxide; Ru(CF3CO2)CO(PPh3)2; at 140 ℃; for 4h; Equilibrium constant;
potassium hydroxide; Ru(CF3CO2)CO(PPh3)2; at 140 ℃; for 5h; Equilibrium constant; Rate constant;
1,3-Dichloropropane
142-28-9

1,3-Dichloropropane

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

glycidyl methyl ether
930-37-0

glycidyl methyl ether

1,2-Epoxyhexane
1436-34-6

1,2-Epoxyhexane

2,3-Dichloroprop-1-ene
78-88-6

2,3-Dichloroprop-1-ene

2-chloroallyl alcohol
5976-47-6

2-chloroallyl alcohol

1,2,2-trichloropropane
3175-23-3

1,2,2-trichloropropane

1,2-Dichloropropane
26198-63-0,78-87-5

1,2-Dichloropropane

cis-1,3-Dichloropropene
10061-01-5

cis-1,3-Dichloropropene

1,2,3-trichloro-1-propene
13116-58-0

1,2,3-trichloro-1-propene

(1Z)-1,2,3-trichloroprop-1-ene
96-19-5,13116-58-0,13116-57-9

(1Z)-1,2,3-trichloroprop-1-ene

1,3,3-trichloro-propene
2953-50-6

1,3,3-trichloro-propene

1<i>t</i>,3,3-trichloro-propene
2598-01-8

1t,3,3-trichloro-propene

chlorodibromomethane
124-48-1

chlorodibromomethane

1,1,2-trichloropropane
598-77-6

1,1,2-trichloropropane

2,3-Dichloro-1-propanol
616-23-9

2,3-Dichloro-1-propanol

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

1,2,3-trichloropropane
96-18-4

1,2,3-trichloropropane

3,3-dichloropropene
563-57-5

3,3-dichloropropene

3,3-dichloroallyl chloride
2567-14-8

3,3-dichloroallyl chloride

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

allyl alcohol
107-18-6

allyl alcohol

hydroxy-2-propanone
116-09-6

hydroxy-2-propanone

chloroacetone
78-95-5

chloroacetone

cyclopentanone
120-92-3

cyclopentanone

chlorobenzene
108-90-7

chlorobenzene

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

isopropyl alcohol

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

(E)-1,3-dichloro-prop-1-ene
10061-02-6

(E)-1,3-dichloro-prop-1-ene

Conditions
Conditions Yield
With sodium hydroxide; water; at 45 - 62.4 ℃; under 112.511 - 750.075 Torr; Product distribution / selectivity;
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

3,4-dihydro-2<i>H</i>-pyran
110-87-2

3,4-dihydro-2H-pyran

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9,26354-94-9

3,4,5,6-tetrahydro-2H-pyran-2-one

propan-1-ol
71-23-8

propan-1-ol

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

ethanol
64-17-5

ethanol

pentan-1-ol
71-41-0

pentan-1-ol

2,2-dimethoxy-3-octanol
19841-72-6

2,2-dimethoxy-3-octanol

4-pentenyl propionate
30563-30-5

4-pentenyl propionate

4-pentenyl pentanoate
30563-32-7

4-pentenyl pentanoate

Cyclopentanol
96-41-3

Cyclopentanol

cyclohexyl cyclohexanecarboxylate
15840-96-7

cyclohexyl cyclohexanecarboxylate

cyclopentanone
120-92-3

cyclopentanone

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
Conditions Yield
With air pretreated CeO2; at 350 ℃; under 760.051 Torr; Flow reactor;
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

3,4-dihydro-2<i>H</i>-pyran
110-87-2

3,4-dihydro-2H-pyran

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9,26354-94-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

ethanol
64-17-5

ethanol

pentan-1-ol
71-41-0

pentan-1-ol

2,2-dimethoxy-3-octanol
19841-72-6

2,2-dimethoxy-3-octanol

4-pentenyl propionate
30563-30-5

4-pentenyl propionate

4-pentenyl pentanoate
30563-32-7

4-pentenyl pentanoate

Cyclopentanol
96-41-3

Cyclopentanol

cyclohexyl cyclohexanecarboxylate
15840-96-7

cyclohexyl cyclohexanecarboxylate

cyclopentanone
120-92-3

cyclopentanone

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
Conditions Yield
With H2 pretreated ZnO-modified CeO2; at 350 ℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

3,4-dihydro-2<i>H</i>-pyran
110-87-2

3,4-dihydro-2H-pyran

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9,26354-94-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

ethanol
64-17-5

ethanol

pentan-1-ol
71-41-0

pentan-1-ol

2,2-dimethoxy-3-octanol
19841-72-6

2,2-dimethoxy-3-octanol

4-pentenyl propionate
30563-30-5

4-pentenyl propionate

4-pentenyl pentanoate
30563-32-7

4-pentenyl pentanoate

cyclohexyl cyclohexanecarboxylate
15840-96-7

cyclohexyl cyclohexanecarboxylate

cyclopentanone
120-92-3

cyclopentanone

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
Conditions Yield
With H2 pretreated MnOx-modified CeO2; at 350 ℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

3,4-dihydro-2<i>H</i>-pyran
110-87-2

3,4-dihydro-2H-pyran

2-Methylcyclopentanone
1120-72-5

2-Methylcyclopentanone

n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

ethanol
64-17-5

ethanol

pentan-1-ol
71-41-0

pentan-1-ol

2,2-dimethoxy-3-octanol
19841-72-6

2,2-dimethoxy-3-octanol

4-pentenyl propionate
30563-30-5

4-pentenyl propionate

4-pentenyl pentanoate
30563-32-7

4-pentenyl pentanoate

cyclohexyl cyclohexanecarboxylate
15840-96-7

cyclohexyl cyclohexanecarboxylate

cyclopentanone
120-92-3

cyclopentanone

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

Conditions
Conditions Yield
With H2 pretreated Na2O-modified CeO2; at 350 ℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;
2,3,4,5-tetrahydropyridine
505-18-0

2,3,4,5-tetrahydropyridine

cyclopentanone
120-92-3

cyclopentanone

Conditions
Conditions Yield
With chloroform; sulfuric acid;
chloroform
67-66-3,8013-54-5

chloroform

cyclopentyl azide
33670-50-7

cyclopentyl azide

sulfuric acid
7664-93-9

sulfuric acid

2,3,4,5-tetrahydropyridine
505-18-0

2,3,4,5-tetrahydropyridine

cyclopentanone
120-92-3

cyclopentanone

Conditions
Conditions Yield
furfural
98-01-1

furfural

acetone
67-64-1

acetone

2-methylfuran
534-22-5

2-methylfuran

4-(furan-2-yl)butan-2-one
699-17-2

4-(furan-2-yl)butan-2-one

cyclopentanone
120-92-3

cyclopentanone

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

4-(furan-2-yl)butan-2-ol
6963-39-9,71638-59-0

4-(furan-2-yl)butan-2-ol

Conditions
Conditions Yield
With hydrogen; In isopropyl alcohol; at 180 ℃; for 3h; under 31029.7 Torr; Autoclave;
10.5 %Chromat.
12.1 %Chromat.
12.5 %Chromat.
8.8 %Chromat.
6.8 %Chromat.
furfural
98-01-1

furfural

acetone
67-64-1

acetone

furan
110-00-9

furan

2-methylfuran
534-22-5

2-methylfuran

4-(furan-2-yl)butan-2-one
699-17-2

4-(furan-2-yl)butan-2-one

cyclopentanone
120-92-3

cyclopentanone

4-(furan-2-yl)butan-2-ol
6963-39-9,71638-59-0

4-(furan-2-yl)butan-2-ol

Conditions
Conditions Yield
With hydrogen; In isopropyl alcohol; at 180 ℃; for 3h; under 31029.7 Torr; Autoclave;
8.2 %Chromat.
13.9 %Chromat.
40.9 %Chromat.
13.1 %Chromat.
5.3 %Chromat.

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