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Cas Database

107-87-9

107-87-9

Identification

  • Product Name:2-Pentanone

  • CAS Number: 107-87-9

  • EINECS:203-528-1

  • Molecular Weight:86.1338

  • Molecular Formula: C5H10O

  • HS Code:2914.19

  • Mol File:107-87-9.mol

Synonyms:4-Methyl-2-butanone;Ethylacetone;Methyl n-propyl ketone;Methyl propyl ketone;NSC 5350;Propylmethyl ketone;2-Pentanone ( Methyl propyl ketone);

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,HarmfulXn

  • Hazard Codes:F,Xn

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH302 Harmful if swallowed 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 Remove contaminated clothes. Rinse skin with plenty of water or shower. 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 Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Exposure can cause irritation of eyes, nose and throat. (USCG, 1999) INHALATION. Symptoms: Cough. Dizziness. Drowsiness. Dullness. Headache. Sore throat. First aid: Fresh air, rest. Refer for medical attention. SKIN: Symptoms: Dry skin. Redness. First aid: Remove contaminated clothes. Rinse skin with plenty of water or shower. EYES: Symptoms: Redness. Pain. First aid: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. INGESTION: Symptoms: Abdominal pain. Nausea. First aid: Rinse mouth. Do NOT induce vomiting. Refer for medical attention.

  • Fire-fighting measures: Suitable extinguishing media In case of fire: keep drums, etc., cool by spraying with water. AFFF, alcohol-resistant foam, powder, carbon dioxide. Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon dioxide and carbon monoxide, may be formed when involved in fire. Behavior in Fire: Flashback along vapor trail may occur. (USCG, 1999) 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. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

  • 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.Store in tightly closed containers in a cool, well ventilated area away from oxidizers. Where possible, automatically pump liquid from drums or other storage containers to process containers. Sources of ignition such as smoking and open flames are prohibited where this chemical is handled, used or stored. Metal containers involving the transfer of 5 gallons or more of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Wherever this chemical is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 150 ppm (530 mg/cu m).Biological 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:AHH
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Relevant articles and documentsAll total 327 Articles be found

Isobutanol and methanol synthesis on copper catalysts supported on modified magnesium oxide

Xu, Mingting,Gines, Marcelo J. L.,Hilmen, Anne-Mette,Stephens, Brandy L.,Iglesia, Enrique

, p. 130 - 147 (1997)

Alcohols are selectively produced from CO/H2 on K-CuMgCeOx catalysts, but synthesis rates are strongly inhibited by CO2 formed during reaction. Reaction pathways involve methanol synthesis on Cu, chain growth to C2+ alcohols, and metal-base bifunctional coupling of alcohols to form isobutanol. Ethanol reactions on K-Cu0.5Mg5CeOx show that Cu catalyzes both alcohol dehydrogenation and aldol condensation reactions. CeO2 increases Cu dispersion and MgO surface area and K decreases Cu dispersion, but increases the density of basic sites. Reactions of acetaldehyde and 13C-labeled methanol lead to 1-13C-propionaldehyde, a precursor to isobutanol. The density and strength of basic sites were measured using a 12CO2/13CO2 isotopic jump method that probes the number and chemical properties of basic sites available at typical isobutanol synthesis temperatures. K or CeO2 addition to CuMgOx increases the density and strength of basic sites and the rates of base-catalyzed ethanol condensation reactions leading to acetone and n-butyraldehyde. The presence of CO in the He carrier during temperature-programmed surface reactions of ethanol preadsorbed on Cu0.5Mg5CeOx decreases the rate of base-catalyzed condensation reactions of preadsorbed ethanol, possibly due to the poisoning of basic and Cu sites by the CO2 formed from CO via water-gas shift reactions.

An In-Situ Self-regeneration Catalyst for the Production of Renewable Penta-1,3-diene

Feng, Ruilin,Qi, Yanlong,Liu, Shijun,Cui, Long,Dai, Quanquan,Bai, Chenxi

, p. 9495 - 9498 (2021)

Catalyst deactivation is a problem of great concern for many heterogeneous reactions. Here, an urchin-like LaPO4 catalyst was easily developed for pentane-2,3-diol dehydration; it has an impressive ability to restore the activity in situ by itself during the reaction, accounting for its high stability. This facilitates the efficient production of renewable penta-1,3-diene from pentane-2,3-dione via a novel approach, where penta-2,3-diol was obtained as an intermediate in 95 % yield under mild conditions.

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Van Volkenburgh et al.

, p. 3595 (1949)

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Bailey et al.

, p. 2997 (1972)

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SOME THERMAL TRANSFORMATION CHARACTERISTICS OF DIHYDROSYLVAN

Karakhanov, E. A.,Karzhavina, N. P.,Brezhnev, L. Yu.

, p. 191 - 192 (1982)

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Oxidation by a "H2O2-vanadium complex-pyrazine-2-carboxylic acid" reagent 5. Oxidation of lower alkanes with the formation of carbonyl compounds

Shul'pin, G. B.,Drago, R. S.,Gonzalez, M.

, p. 2386 - 2388 (1996)

Lower alkanes (ethane, propane, n-butane, n-pentane) are readily oxidized in acetonitrile solvent by H2O2 with vanadate anion - pyrazine-2-carboxylic acid (PCA), as the catalyst at 75 deg C and pressure of ca. 3 atm to produce predominantly or exclusively ketones (aldehydes).Isobutane is transformed selectively into tert-butyl alcohol.The oxidation of cyclohexane at 26 deg C in acetone or acetic acid is less efficient than in acetonitrile.The reaction does not occur in tert-butyl alcohol.

Catalytic aerobic oxidation of alcohols by Fe(NO3)3-FeBr3

Martín, Sandra E,Suárez, Darío F

, p. 4475 - 4479 (2002)

Selective aerobic oxidation of secondary and benzylic alcohols was efficiently accomplished by the binary catalyst system Fe(NO3)3-FeBr3 under air at room temperature. The oxidation developed in mild conditions and showed

A structure/catalytic activity study of gold(i)-NHC complexes, as well as their recyclability and reusability, in the hydration of alkynes in aqueous medium

Fernández, Gabriela A.,Chopa, Alicia B.,Silbestri, Gustavo F.

, p. 1921 - 1929 (2016)

We conducted a structure/catalytic activity study of water-soluble gold(i) complexes-supporting sulfonated NHC ligands-in the hydration of alkynes in pure water or water nsp;:nsp;methanol (1nsp;:nsp;1), as well as their recyclability. Comparative studies were carried out with the addition of different silver salts. Our results indicate that the bulkier complex is the most effective and that the addition of methanol as co-solvent not only shortens reaction times but also stabilizes the less bulky complexes.

Relative and absolute kinetic studies of 2-butanol and related alcohols with tropospheric Cl atoms

Ballesteros, Bernabe,Garzon, Andres,Jimenez, Elena,Notario, Alberto,Albaladejo, Jose

, p. 1210 - 1218 (2007)

A newly constructed chamber/Fourier transform infrared system was used to determine the relative rate coefficient, ki, for the gas-phase reaction of Cl atoms with 2-butanol (k1), 2-methyl-2-butanol (k 2), 3-methyl-2-butanol (k3), 2,3-dimethyl-2-butanol (k4) and 2-pentanol (k5). Experiments were performed at (298 ± 2) K, in 740 Torr total pressure of synthetic air, and the measured rate coefficients were, in cm3 molecule-1 s -1 units (±2σ): k1 = (1.32 ± 0.14) × 10-10, k2 = (7.0 ± 2.2) × 10 -11, k3 = (1.17 ± 0.14) × 10-10, k4 = (1.03 ± 0.17) × 10-10 and k5 = (2.18 ± 0.36) × 10-10, respectively. Also, all the above rate coefficients (except for 2-pentanol) were investigated as a function of temperature (267-384 K) by pulsed laser photolysis-resonance fluorescence (PLP-RF). The obtained kinetic data were used to derive the Arrhenius expressions: k1(T) = (6.16 ± 0.58) × 10 -11exp[(174 ± 58)/T], k2(T) = (2.48 ± 0.17) × 10-11exp[(328 ± 42)/T], k3(T) = (6.29 ± 0.57) × 10-11exp[(192 ± 56)/T], and k 4(T) = (4.80 ± 0.43) × 10-11exp[(221 ± 56)/T] (in units of cm3 molecule-1 s-1 and ±σ). Results and mechanism are discussed and compared with the reported reactivity with OH radicals. Some atmospheric implications derived from this study are also reported. This journal is the Owner Societies.

A thermodynamic study of the ketoreductase-catalyzed reduction of 2-alkanones in non-aqueous solvents

Tewari, Yadu B.,Schantz, Michele M.,Phinney, Karen W.,Rozzell, J. David

, p. 89 - 96 (2005)

Equilibrium constants K have been measured for the reactions (2-alkanone + 2-propanol = 2-alkanol + acetone), where 2-alkanone = 2-butanone, 2-pentanone, 2-hexanone, 2-heptanone, and 2-octanone and 2-alkanol = 2-butanol, 2-pentanol, 2-hexanol, 2-heptanol, and 2-octanol. The solvents used were n-hexane, toluene, methyl tert-butyl ether (MTBE), and supercritical carbon dioxide SCCO 2 (pressure P - 10.0 MPa). The temperature range was T - (288.15 to 308.27) K. Chiral analysis of the reaction products showed that the enzyme used in this study was stereoselective for the 2-octanone reaction system, i.e. only (S)-(+)-2-octanol was formed. For the reactions involving butanone, pentanone, and hexanone, the products were racemic mixtures of the respective (S)-(+)-2-alkanol and the (R)-(-)-2-alkanol. Chiral analysis showed that for the 2-heptanone reaction system, the 2-alkanol product was a mixture of (S)-(+)-2-heptanol and (R)-(-)-2-heptanol, at the respective mole fractions of 0.95 and 0.05. The equilibrium constant for the reaction system involving 2-butanone carried out in n-hexane was measured at several temperatures. For this reaction, the values for the thermodynamic reaction quantities at T= 298. 15 K are: K= 0.838±0.013; the standard molar Gibbs free energy change ΔrgHm° = (0.44±0.040) kJ · mol-1; the standard molar enthalpy change ΔrgHm° = -(1.2±1.7) kJ mol-1, and the standard molar entropy change ΔrgHm° = -(5.5±5.7) J K-1 mol-1. Interestingly, inspection of the values of the equilibrium constants for these reactions carried out in n-hexane, toluene, MTBE, and SCCO2 shows that these values are comparable and have little dependence on the solvent used to carry out the reaction. The values of the equilibrium constants decrease monotonically with increasing value of the number of carbons Nc and trend towards a limiting value of ≈0.30 for Nc > 8. Published by Elsevier Ltd.

Developing an efficient catalyst for controlled oxidation of small alkanes under ambient conditions

Nagababu, Penumaka,Yu, Steve S.-F.,Maji, Suman,Ramu, Ravirala,Chan, Sunney I.

, p. 930 - 935 (2014)

The tricopper complex [CuICuICuI(7-N- Etppz)]1+, where 7-N-Etppz denotes the ligand 3,3′-(1,4- diazepane-1,4-diyl)bis[1-(4-ethyl piperazine-1-yl)propan-2-ol], is capable of mediating facile conversion of methane into methanol upon activation of the tricopper cluster by dioxygen and/or HO at room temperature. This is the first molecular catalyst that can catalyze selective oxidation of methane to methanol without over-oxidation under ambient conditions. When this CuICu ICuI tricopper complex is activated by dioxygen or H 2O2, the tricopper cluster harnesses a "singlet oxene", the strongest oxidant that could be used to accomplish facile O-atom insertion across a C-H bond. To elucidate the properties of this novel catalytic system, we examine here methane oxidation over a wider range of conditions and extend the study to other small alkanes, including components of natural gas. We illustrate how substrate solubility, substrate recognition and the amount of H2O2 used to drive the catalytic oxidation can affect the outcome of the turnover, including regiospecificity, product distributions and yields of substrate oxidation. These results will help in designing another generation of the catalyst to alleviate the limitations of the present system. This journal is the Partner Organisations 2014.

Product distributions from the OH radical-induced oxidation of n-Pentane and isopentane (2-Methylbutane) in Air

Heimann, Gerald,Warneck, Peter

, p. 677 - 688 (2006)

Hydroxyl radicals, generated by photolysis of H2O2. were reacted with n-pentane and isopentane in air in the absence of nitrogen oxides. The observed product distributions were compared with similar data derived by computer simulations, based on the known reaction mechanisms, to determine relative probabilities for hydrogen abstraction at different sites of the parent compounds and to estimate branching ratios and relative rate coefficients for cross-combination reactions between different peroxy radicals. For n-pentane. the distribution of the pentanols indicates probabilities for hydrogen abstraction, in percent, of q1= 9.1 ± 0.7. q 2 = 56.1 ± 1.8, and q3 = 34.8 ± 1.3. which agree with predictions based on the algorithm proposed by Atkinson. Branching ratios needed to harmonize calculated and observed product distributions are somewhat larger than, although still within the error ranges of. the values found by us previously Comparison between experimental and calculated data confirms the isomerization and decomposition constants recently established for the three pentoxyl radical isomers. The product distribution for isopentane. which is dominated by acetone, acetaldehyde. 2-methyl-butan-2-ol. and 2-methyl-butan-2-hydroperoxide, is in harmony with the predicted oxidation mechanism. Probabilities for hydrogen abstraction from isopentane were estimated to occur to 12% at the primary. 28% at the secondary, and 60% at the tertiary sites, again in agreement with predictions based on the algorithm of Atkinson.

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Grove,J.F.

, p. 2261 - 2263 (1971)

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Reactions in the Photocatalytic Conversion of Tertiary Alcohols on Rutile TiO2(110)

Courtois, Carla,Eder, Moritz,Schnabl, Kordula,Walenta, Constantin A.,Tschurl, Martin,Heiz, Ulrich

, p. 14255 - 14259 (2019)

According to textbooks, tertiary alcohols are inert towards oxidation. The photocatalysis of tertiary alcohols under highly defined vacuum conditions on a titania single crystal reveals unexpected and new reactions, which can be described as disproportionation into an alkane and the respective ketone. In contrast to primary and secondary alcohols, in tertiary alcohols the absence of an α-H leads to a C?C-bond cleavage instead of the common abstraction of hydrogen. Surprisingly, bonds to methyl groups are not cleaved when the alcohol exhibits longer alkyl chains in the α-position to the hydroxyl group. The presence of platinum loadings not only increases the reaction rate but also opens up a new reaction channel: the formation of molecular hydrogen and a long-chain alkane resulting from recombination of two alkyl moieties. This work demonstrates that new synthetic routes may become possible by introducing photocatalytic reaction steps in which the co-catalysts may also play a decisive role.

Enantioselective oxidation of secondary alcohols by the flavoprotein alcohol oxidase from Phanerochaete chrysosporium

Tjallinks, Gwen,Martin, Caterina,Fraaije, Marco W.

, (2021)

The enantioselective oxidation of secondary alcohols represents a valuable approach for the synthesis of optically pure compounds. Flavoprotein oxidases can catalyse such selective transformations by merely using oxygen as electron acceptor. While many flavoprotein oxidases preferably act on primary alcohols, the FAD-containing alcohol oxidase from Phanerochaete chrysosporium was found to be able to perform kinetic resolutions of several secondary alcohols. By selective oxidation of the (S)-alcohols, the (R)-alcohols were obtained in high enantiopurity. In silico docking studies were carried out in order to substantiate the observed (S)-selectivity. Several hydrophobic and aromatic residues in the substrate binding site create a cavity in which the substrates can comfortably undergo van der Waals and pi-stacking interactions. Consequently, oxidation of the secondary alcohols is restricted to one of the two enantiomers. This study has uncovered the ability of an FAD-containing alcohol oxidase, that is known for oxidizing small primary alcohols, to perform enantioselective oxidations of various secondary alcohols.

Rhodium(I)-Catalyzed Biphasic Isomerization of Allylic Alcohols

Alper, Howard,Hachem, Khaled

, p. 2269 - 2270 (1980)

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Wet carbon-based solid acid/potassium bromate as an efficient heterogeneous reagent for oxidation of alcohols under mild conditions

Zali, Abbas,Shokrolahi, Arash

, p. 1064 - 1069 (2008)

Wet carbon-based solid acid and potassium bromate were used as new reagent for oxidation of alcohols to their corresponding aldehyde or ketone derivatives in dichloromethane with good yields. Copyright Taylor & Francis Group, LLC.

Stereochemistry of the Hydrogenolysis of Oxacycloalkanes on Metal Catalysts

Bartok, Mihaly,Notheisz, Ferenc

, p. 667 - 668 (1980)

On the basis of reaction kinetics, H-D exchange, and i.r. studies of the hydrogenolysis of oxirans and oxolans, the opposite regio- and stereo-selectivities of Pt and Ni are interpreted, a new reaction mechanism is proposed, and it is shown experimentally that the reaction mechanism depends inter alia on the steric structure of the molecule.

Bifunctional condensation reactions of alcohols on basic oxides modified by copper and potassium

Gines, Marcelo J. L.,Iglesia, Enrique

, p. 155 - 172 (1998)

Alcohol dehydrogenation and condensation reactions are involved in chain growth pathways on Cu/MgCeOx promoted with potassium. These pathways lead to the formation of isobutanol with high selectivity via reactions of higher alcohols with methanol-derived C1 species in reaction steps also relevant to higher alcohol synthesis from CO/H2 mixtures at higher pressures on K-Cu/MgCeOx catalysts. Ethanol reactions on K-CUyMg5CeOx show that both Cu and basic sites participate in alcohol dehydrogenation and aldol condensation steps leading to n-butyraldehyde and acetone. Chain growth occurs by condensation reactions involving a metal-base bifunctional aldol-type coupling of alcohols. Reactions of 12C2H5OH-13C2H 4O mixtures show that direct condensation reactions of ethanol can occur without requiring the intermediate formation of gas phase acetaldehyde. Reactions of C2H5OH/D2 mixtures show that Cu sites increase the rate of aldol condensation by introducing recombinative desorption sites that remove hydrogen atoms formed in C-H activation steps leading to the unsaturated aldol-type species required for chain growth. Reactions of acetaldehyde and 13C-labeled methanol lead predominantly to 1-13C-propionaldehyde and 2-13C-isobutyraldehyde, both of which lead to isobutanol during CO/H2 reactions. Mixtures of propionaldehyde and 13C-labeled methanol lead to singly-labeled isobutyraldehyde. Chain growth to C2+ alcohols occurs via addition of a methanol-derived C1 species to adsorbed oxygen-containing intermediates. The gradual appearance of 13C in the unlabeled reactant within these mixtures shows that aldol coupling reactions are reversible. Reverse aldol condensation reactions after intramolecular hydride transfer lead to the formation of acetone from ethanol. Isobutyraldehyde is a preferred end-product of aldol-type chain growth reactions of alcohols because it lacks the two α-hydrogens required for subsequent chain growth. 998 Academic Press.

A versatile bi-metallic copper-cobalt catalyst for liquid phase hydrogenation of furfural to 2-methylfuran

Srivastava, Sanjay,Jadeja,Parikh, Jigisha

, p. 1649 - 1658 (2016)

Liquid phase hydrogenation of furfural (FFR) to 2-methyl furan (2-MF) was examined using noble metal free, Cr-free, bi-metallic Cu-Co catalysts. Three supported bi-metallic catalysts (Cu-Co/SiO2, Cu-Co/H-ZSM-5, and Cu-Co/γ-Al2O3) with various Cu/Co molar ratios (x/y = 1, 2, and 4) with fixed Cu loading (x = 10 wt%) were prepared by the impregnation method. The physico-chemical properties of various catalysts were studied by using XRD, N2-sorption, SEM, TEM, TPR, TPD, XANES/EXAFS and CHNS methods. The results confirmed the formation of spinel CuCo2O4 oxides, and much higher dispersion of Cu on acidic supports such as H-ZSM-5 and γ-Al2O3. However, the absence of a spinel CuCo2O4 oxide was observed in Cu-Co/SiO2via XANES/EXAFS results. XRD and TEM results revealed the formation of bigger Cu particles in Cu-Co/SiO2. In the catalytic activity studies, Cu-Co/γ-Al2O3 catalyzed the hydrogenation of furfural with 98.8% conversion, resulting in maximal selectivity of 2-MF due to the presence of maximal Cu-CoOx sites. The H-ZSM-5 supported catalyst had marginally less 2-MF selectivity, whereas the silica supported catalyst exhibited maximum selectivity towards furfuryl alcohol (FOL) because of the large copper particles. H2-TPR and EXAFS results revealed that the incorporation of cobalt metal improves the reducibility of Cu-catalysts, thus improving the catalytic activity. Bi-metallic Cu-Co/γ-Al2O3 catalysts displayed higher activity as compared to their monometallic counterpart, and Cu-Co/γ-Al2O3 (x/y = 1) exhibited the best catalytic performance with 78% selectivity to 2-MF at 220°C and 4 MPa.

Oxidation of Alcohols with H2O2 Catalyzed by Titanium Silicalite-1

Maspero, Federico,Romano, Ugo

, p. 476 - 482 (1994)

Primary and secondary alcohols are oxidised by H2O2 in the presence of titanium silicalite-1 to carbonylic compounds.Reaction rates follow the general trend secondary primary methanol.Rates are sensitive to position effects of the OH group, to chain branching effects, and to molecular size of the alcohol.Kinetic orders with respect to H2O2 are generally close to zero, while those with respect to the alcohol are strongly affected by the solvent used.The kinetic pattern is interpreted in terms of an interaction of the lattice titanium atom of titanium silicalite-1 with H2O2.The kinetic order with respect to the alcohol can be interpreted either in terms of titanium-alcohol adducts or with a selective alcohol sorption in the catalyst pores.The reaction pattern is consistent with a process taking place essentially inside the zeolite channels, with a transition-state-restricted shape-selectivity.The nature of the titanium hydroperoxide involved in the intermediate complex is discussed.

[α-PW12O40]3- immobilized on ionic liquid-modified polymer as a heterogeneous catalyst for alcohol oxidation with hydrogen peroxide

Lang, Xianjun,Li, Zhen,Xia, Chungu

, p. 1610 - 1616 (2008)

Ionic liquid-modified polystyrene resin beads were demonstrated to be an appropriate support for polyoxometalate. In this heterogeneous catalytic system, alcohols can be efficiently oxidized to corresponding carbonyl groups with H2O2 in CH3CN. The catalyst can be easily recovered by filtration and recycled without apparent loss of catalytic performance. Copyright Taylor & Francis Group, LLC.

New efficient aerobic oxidation of some alcohols with dioxygen catalysed by N-hydroxyphtalimide with vanadium co-catalysts

Figiel, Pawel J.,Sobczak, Jaroslaw M.,Ziolkowski, Jozef J.

, p. 244 - 245 (2004)

New efficient vanadium co-catalysts have been developed for the oxidation of some alcohols with O2 catalysed by N-hydroxyphthalimide (NHPI). Various alcohols (primary and secondary) were selectively oxidized by O 2 under mild conditions in the presence of a catalytic amount of NHPI as a radical-producing agent combined with small amounts of vanadium complexes with or without the addition of a simple salt (e.g. LiCl) or base (e.g. pyridine).

Highly selective C=C bond hydrogenation in α,β-unsaturated ketones catalyzed by hectorite-supported ruthenium nanoparticles

Khan, Farooq-Ahmad,Vallat, Armelle,Süss-Fink, Georg

, p. 168 - 173 (2012)

Metallic ruthenium nanoparticles intercalated in hectorite (particle size ~7 nm) were found to catalyze the specific hydrogenation (conversion 100%, selectivity > 99.9%) of the carbon-carbon double bond in α,β- unsaturated ketones such as 3-buten-2-one, 3-penten-2-one, 4-methyl-3-penten-2- one. The catalytic turnovers range from 765 to 91,800, the reaction conditions being very mild (temperature 35 °C and constant hydrogen pressure 1-10 bar). After a catalytic run, the catalyst can be recycled and reused without loss of activity and selectivity

Photodecomposition of iodopentanes in air: Product distributions from the self-reactions of n-pentyl peroxyl radicals

Heimann, Gerald,Benkelberg, Heinz-Jrgen,Bge, Olaf,Warneck, Peter

, p. 126 - 138 (2002)

Product distributions from the 254-nm photooxidation of the three iodopentane isomers were explored as a technique for studying the self-reactions of individual pentyl peroxyl radicals (in air at ambient temperature and pressure). Pentanols and the associated carbonyl compounds (pentanal or pentanones) were major products as expected. Other major products resulted from the isomerization of pentan-1-oxyl and pentan-2-oxyl radicals, but their nature could not be identified. Minor products were alcohols and carbonyl compounds arising from the decomposition of pentoxyl radicals. Diols and mixed hydroxycarbonyl compounds from cross-combination reactions were essentially absent, in contrast to expectation. The observed product distributions were evaluated to derive branching ratios for the radical-preserving pathways of the self-reactions, 0.42 ± 0.17, 0.46 ± 0.10, 0.39 ± 0.08, for pentan-1-yl peroxyl, pentan-2-yl peroxyl, and pentan-3-yl peroxyl, respectively. Rate coefficients derived for the decomposition of the corresponding pentoxyl radicals, relative to their reaction with oxygen, are (5.1 ± 0.5) × 1018, (1.0 ± 0.2) × 1018, and (3.2 ± 0.3) × 1018 molecule cm-3, respectively. Rate constants for the isomerization of pentan-1-oxyl and pentan-2-oxyl were estimated from the contributions of isomerization products to the total amounts of products as (4.0 ± 1.1) × 105 s-1 and (1.0 ± 2.0) × 105 s-1, respectively.

Bioorganometallic chemistry: Co-factor regeneration, enzyme recognition of biomimetic 1,4-NADH analogs, and organic synthesis; tandem catalyzed regioselective formation of N-substituted-1,4-dihydronicotinamide derivatives with [Cp*Rh(bpy)H]+, coupled to chiral S-alcohol formation with HLADH, and engineered cytochrome P450s, for selective C-H oxidation reactions

Lo, H. Christine,Ryan, Jessica D.,Kerr, John B.,Clark, Douglas S.,Fish, Richard H.

, p. 38 - 52 (2017)

Two novel tandem catalysis approaches for the chiral synthesis of S-alcohols from reduction of their prochiral ketones with Horse Liver Alcohol Dehydrogenase (HLADH), and selective C-H oxidation reactions with protein engineered Cytochrome P450s, are presented. We utilized a co-factor regeneration procedure with three biomimetic NAD+ models that do not contain the pyrophosphate, nor the adenosine group, and either/or a ribose, N-1-benzylnicotinamide triflate, 1, N-4-methoxybenzylnicotinamide triflate, 2, and β-nicotinamide-5′-ribose methyl phosphate, 3, in conjunction with in situ formed [Cp*Rh(bpy)H]+ from [Cp*Rh(bpy)(H2O)]2+ (Cp*?=?η5-C5Me5, bpy?=?2,2'-bipyridyl) and the hydride source, sodium formate, to regioselectively provide their 1,4-NADH analogs, N-benzyl-1,4-dihydronicotinamide, 4, N-4-methoxybenzyl-1,4-dihydronicotinamide, 5, and 1,4-dihydronicotinamide-5′-ribose methylphosphate, 6. Surprisingly, the 1,4-NADH biomimics, 4 and 6, were recognized, in the second tandem catalysis approach, by the natural 1,4-NADH dependent enzyme, HLADH, for catalyzed, highly enantioselective conversions of prochiral ketones to chiral S-alcohols. For example, with phenethylmethyl ketone and benzylmethyl ketone, the corresponding chiral alcohols were formed in >93% ee (S-enantiomer). Thus, 1,4-NADH biomimetic model recognition by HLADH does not significantly depend on the presence of the ribose, pyrophosphate, or adenosine groups to provide chiral products. We will also propose a plausible active site (HLADH)Zn-H intermediate, generated via a hydride transfer from bound 4/6 to Zn, for the enzymatic reduction of prochiral aryl/alkyl ketones to their chiral aryl/alkyl S-alcohols. Furthermore, the use of protein engineered cytochrome P450 enzymes provided improved molecular recognition of the above mentioned 1,4-NADH biomimetic co-factors, 4 and 5, for selective C-H oxidation reactions. For example, 1,4-NADH dependent mutants of natural 1,4-NAD(P)H dependent P450 BM-3 and 1,4-NADH dependent P450 CAM, with biomimetic co-factors 4 and 5, provided selective oxidation of p-nitrophenoxydecanoic acid to ω-oxydecanocarboxylic acid and p-nitrophenol, via C-H hydroxylation and β-hydrogen elimination, while oxidation of camphor provided hydroxycamphor, respectively. We will discuss the various parameters that effect molecular recognition of the biomimics, including protein engineering of both P450 BM-3 and P450 CAM enzymes, while determining the effect of the co-factor regeneration procedure on HLADH and P450 enzyme activity. These important observations have created new paradigms for the synthesis of organic compounds of interest, with the economically more favorable biomimics of NAD+, 1,4-NADH, and 1,4-NAD(P)H as co-factors, in tandem with the use of [Cp*Rh(bpy)(H)]+ as a regioselective catalytic reagent for co-factor regeneration.

A novel method for the synthesis of aldehydes and ketones

Pérez G.,Pérez G.,Zavala S.,Pérez G.,Guadarrama M.

, p. 3011 - 3014 (1998)

A new method for the preparation of aldehydes and ketones from alkylnitrites and BF2.Et2O or anhydrous ZnCl2 is described. Twelve different nitrites were tested obtaining yields over 90%. When these Lewis acids were substituted by anhydrous AlCl3, the yield decreased to a value below 20%.

Cr-free Cu-catalysts for the selective hydrogenation of biomass-derived furfural to 2-methylfuran: The synergistic effect of metal and acid sites

Dong, Fang,Zhu, Yulei,Zheng, Hongyan,Zhu, Yifeng,Li, Xianqing,Li, Yongwang

, p. 140 - 148 (2015)

Our work focuses on exploring Cr-free Cu-catalysts for the highly efficient conversion of biomass-derived furfural to value-added bio-fuel 2-methylfuran. Three supported Cu-catalysts (Cu/SiO2, Cu/Al2O3, and Cu/ZnO) were prepared by the typical precipitation method, and Cu/SiO2 catalyst exhibited the best catalytic performance with an 89.5% yield to 2-MF. A series of characteristic results indicated that the high yield of 2-methylfuran on Cu/SiO2 catalyst was assigned to synergistic effect of metal and the weak acid sites. Among them, Cu/ZnO catalyst exhibited maximum furfuryl alcohol selectivity because of the large Cu particles, while Cu/Al2O3 catalyst had low 2-methylfuran selectivity due to the insufficient weak acid sites. For Cu/SiO2 catalyst, the highly dispersed Cu particles and the strong metal-support interaction are propitious to its superior catalytic activity. Therefore, copper species are composed on different supports as a result of the different interaction of metal-support to affect their catalytic activity, while products selectivity is related to the acidic property of catalyst. In addition, temperature programmed desorption of furfural indicated that the adsorption-desorption properties of catalyst surface species would influence the rate of furfural hydrogenation.

A series second-first-order mechanism for the oxidation of primary and secondary alcohols by Cr(VI) reagents

Agarwal, Seema,Tiwari,Sharma

, p. 1963 - 1974 (1990)

Based on the experimental data, a definite mechanism for the oxidation of primary and secondary alcohols with PCC and two newly synthesized Cr(VI) reagents has been proposed. The reaction has been shown to be a series reaction rather than a simple one step reaction as reported in the literature. The mechanism proposed has been exemplified by taking 2-pentanol as an example. The kinetic isotope studies have also been performed.

REGIOSELECTIVE PREPARATION OF KINETIC TRIMETHYLSILYL ENOL ETHERS FROM β-KETO SILANES

Yamamoto, Yohsuke,Ohdoi, Keisuke,Nakatani, Masayuki,Akiba, Kin-ya

, p. 1967 - 1968 (1984)

Kinetic trimethylsilyl enol ethers were prepared regioselectively by the two-step method, i.e., trimethylsilyl triflate catalyzed rearrangement of β-keto silanes which were prepared from trimethylsilylmethylcopper and acid chlorides.

Sato,Cvetanovic

, p. 953,955 (1959)

Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

Chu, Qingyan,He, Guangke,Xi, Yang,Wang, Ping,Yu, Haoxuan,Liu, Rui,Zhu, Hongjun

, p. 46 - 50 (2018)

A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.

TRANSFORMATION OF ORGANIC COMPOUNDS IN THE PRESENCE OF METAL COMPLEXES I. TRANSFORMATION OF UNSATURATED ALCOHOLS WITH METAL COMPLEX CATALYSTS

Felfoeldi, K.,Bartok, M.

, p. C37 - C40 (1985)

The transformations of unsaturated alcohols (2-hexen-3-ol, 1-penten-4-ol, 1-penten-4-ol and 2-methylenecyclohexanol) were studied under identical experimental conditions in the presence of various Rh and Ru complexes (RhCl(PPh3)3, RhH(PPh3)4, RhCl3*3H2O, RhCl3*3H2O + PPh3, Rh(COD)Cl2, Rh(COD)Cl2 + PPh3, RhCl2(PPh3)3 and RuH2(PPh3)4).Several aspects of both the unsaturated alcohol and the complex exertconsiderable effects on the extent of the main reactions; isomerization to ketone and double-bond migration.

In operando XAS investigation of reduction and oxidation processes in cobalt and iron mixed spinels during the chemical loop reforming of ethanol

Carraro,Vozniuk,Calvillo,Nodari,La Fontaine,Cavani,Agnoli

, p. 20808 - 20817 (2017)

FeCo2O4 and CoFe2O4 nanoparticles have been studied as oxygen carriers for the Chemical Loop Reforming (CLR) of ethanol. By using in operando X-ray absorption spectroscopy we have followed in real time the chemical and structural changes that take place on the materials as a function of temperature and reactive atmosphere (i.e. ethanol/water streams). During the first step of CLR for both oxides the most active chemical species are the cations in the tetrahedral sites, irrespective of their chemical nature. Quite rapidly the spinel structure is transformed into a mix of wüstite-type oxide and metal alloys, but the formation of a metal phase is easier in the case of cobalt, while iron shows a marked preference to form wüstite type oxide. Despite the good reducibility of FeCo2O4 imparted by the high amount of cobalt, its performance in the production of hydrogen is quite poor due to an inefficient oxidation by water steam, which is able to oxidize only the outer shell of the nanoparticles. In contrast, CoFe2O4 due to the residual presence of a reducible wüstite phase shows a higher hydrogen yield. Moreover, by combining the structural information provided by X-ray absorption spectroscopy with the analysis of the byproducts of ethanol decomposition we could infer that FeCo2O4 is more selective than CoFe2O4 for the selective dehydrogenation of ethanol to acetaldehyde because of the higher amount of Fe(iii) ions in tetrahedral sites.

Reaction of metal alkoxides with 3-alkyl-substituted acetylacetone derivatives - Coordination vs. hydrodeacylation

Puchberger, Michael,Rupp, Wolfgang,Bauer, Ulrike,Schubert, Ulrich

, p. 1289 - 1294 (2004)

Reaction of Ti(OiPr)4 or Zr(OPr)4 with 1 or 2 molar equiv of the 3-alkyl-substituted acetylacetone derivatives 3-acetyl-6-trimethoxysilylhexane-2-one or 3-acetylpentane-2-one not only gives the corresponding β-diketonate complexes but also results in about 15% hydrodeacylation of the β-diketone. With the stronger Lewis acid Al(O sBu)3 hydrodeacylation prevails. Hydrodeacylation is suppressed when a 1:5 ratio of metal alkoxide and β-diketone is reacted.

Mn-trimethyltriazacyclononane/ascorbic acid: A remarkably efficient catalyst for the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide

Berkessel, Albrecht,Sklorz, Christoph A.

, p. 7965 - 7968 (1999)

The system comprised of manganese(II) acetate or sulfate, 1,4,7-trimethyl-1,4,7-triazacyclononane (TMTACN) and ascorbic acid efficiently catalyzes the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide. For example, in the presence of as little as 0.03 mol% of Mn2+, methyl acrylate is converted to its epoxide in 97% yield. Under the same conditions, 2-pentanol yielded 2-pentanone in almost quantitative yield. With E- and Z-1-deuterio-1-octene as substrates, the epoxidation was shown to proceed with almost exclusive (94±2%) retention of configuration.

Zeolite supported permanganate: An efficient catalyst for selective oxidation of enamines, alkylarenes and unsaturated alcohols

Sreekumar,Padmakumar, Raghavakaimal

, p. 5143 - 5146 (1997)

Potassium permanganate supported on zeolite can be used for the selective oxidation of various enamines, alkylarenes and unsaturated alcohols to the corresponding ketones, in good yield. Arenes were selectively oxidized at the benzylic position. If the benzylic carbon is secondary, ketones are obtained, and alcohols are produced if the benzylic position is tertiary. In contrast unsaturated secondary alcohols selectively undergo oxidation to the corresponding olefinic ketones without affecting the carbon-carbon double bonds.

-

Bassette,Day

, p. 482 (1960)

-

-

Meerwein

, p. 249 (1913)

-

A new strategy for the efficient synthesis of 2-methylfuran and γ-butyrolactone

Zhu, Yu-Lei,Xiang, Hong-Wei,Li, Yong-Wang,Jiao, Haijun,Wu, Gui-Sheng,Zhong, Bing,Guo, Guang-Qing

, p. 208 - 210 (2003)

A novel process involving the coupling of the hydrogenation of furfural and the dehydrogenation of 1,4-butanediol has been studied in the vapor phase for the synthesis of 2-methylfuran (2-MF) and γ-butyrolactone γ-BL) over the same Cu-based catalyst. It was found that hydrogen and heat energy are utilized with high efficiency in this process.

Controlled Monooxygenation of n- and Isoalkanes with Molecular Oxygen Catalyzed in Nonheme Iron Complex/Hydroquinone Systems

Funabiki, Takuzo,Kashiba, Koji,Toyoda, Takehiro,Yoshida, Satohiro

, p. 2303 - 2306 (1992)

Linear and branched alkanes are monooxygenated with O2 in nonheme iron complex/hydroquinone systems.Selectivity to form either alcohols or carbonyl compounds was controlled by the pyridine concentration.Reactivity of dfferent types of C-H bonds was affected by the substituents of hydroquinones, suggesting that hydroquinones are located in the vicinity of an active center in the product formation step.

-

Fry et al.

, p. 1252 (1960)

-

-

Djerassi et al.

, (1960)

-

-

Royals

, p. 1508 (1945)

-

A direct imaging of amphiphilic catalysts assembled at the interface of emulsion droplets using fluorescence microscopy

Gao, Jinbo,Zhang, Yongna,Jia, Guoqing,Jiang, Zongxuan,Wang, Shouguo,Lu, Hongying,Song, Bo,Li, Can

, p. 332 - 334 (2008)

An amphiphilic fluorescent catalyst Q9[EuW10O 36] (Q = [(C18H37)2N +(CH3)2]), assembled in the interface of emulsion systems, was directly imaged by fluores

Thermochemical Studies of Carbonyl Reactions. 2. Steric Effects in Acetal and Ketal Hydrolysis

Wiberg, Kenneth B.,Squires, Robert R.

, p. 4473 - 4478 (1981)

A calorimetric determination of the enthalpies of hydrolysis of a series of alkyl-substituted dimethyl acetals is reported.These data are critically compared with the enthalpies of hydrolysis from an analogous set of aliphatic dimethyl ketals derived from 2-alkanones.The acetals exhibit a significantly attenuated range in their enthalpies of hydrolysis relative to that for ketal hydrolysis.The free energies of acetal formation in solution were modeled by measurements of the corresponding free energies of hemiacetal formation from the aldehydes in neutral methanol.The observed free-energy differences are satisfactorily correlated with the Taft Es steric substituent constant scale, but the corresponding acetal enthalpy data vary in a complex manner.The role of entropy in determining kinetic and equilibrium steric effects in a variety of other systems is discussed.Preliminary molecular mechanics calculations on these systems indicate the importance of bond angle bending in evaluating the torsional potential at a carbonyl group.Many of the compounds were found to possess several conformations having comparable energies.

Decarboxylation and simultaneous reduction of silver(I) β-ketocarboxylates with three types of coordinations

Hatamura, Mariko,Yamaguchi, Shunro,Takane, Shin-Ya,Chen, Yu,Suganuma, Katuaki

, p. 8993 - 9003 (2015)

A series of silver(I) β-ketocarboxylates were prepared by reaction of β-ketocarboxylic acids with silver nitrate in the presence of diethanolamine. The silver(I) β-ketocarboxylates decomposed over a narrow temperature range to form metallic silver, CO2, and the corresponding ketones. In addition, products derived from radical intermediates were detected by mass spectroscopic analysis for some silver(I) β-ketocarboxylates. Infrared and solid state 13C-NMR spectra of silver(I) β-ketocarboxylates suggested the presence of two types of structures involving a carbonyl group in addition to the dimeric eight-membered ring structure as in the structure of silver(I) stearate. The silver(I) β-ketocarboxylate model compound used was HCOCH2COOAg and its structures were determined using density functional theory (DFT) and atoms-in-molecules (AIM) methods. Three types of coordinations around the Ag ion differing significantly in Ag-O bond strengths were found. Based on the calculated structures and experimental results, the relationships between the structures and decomposition temperatures are discussed in terms of the thermal decomposition process.

Kinetics and mechanism of the oxidation of alcohols by tetrapropylammonium perruthenate

Chandler, W. David,Wang, Zhao,Lee, Donald G.

, p. 1212 - 1221 (2005)

2-Propanol is oxidized by tetrapropylammonium perruthenate (TPAP) in a reaction that is second order in TPAP and first order in 2-propanol. One of the products, believed to be ruthenium dioxide, is an effective catalyst for the reaction, making it an autocatalytic process. The rate of oxidation is relatively insensitive to the presence of substituents. Primary kinetic deuterium isotope effects are observed when either the hydroxyl or the α hydrogen is replaced by deuterium. The only product obtained from the oxidation of cyclobutanol is cyclobutanone, indicating that the reaction is a two-electron process. Tetrahydrofuran is oxidized at a rate that is several orders of magnitude slower than that observed for 2-propanol, suggesting that the reaction of TPAP with alcohols may be initiated by formation of perruthenate esters. A tentative mechanism consistent with these observations is proposed.

PALLADIUM AND PHASE TRANSFER CATALYZED OXIDATION OF OLEFINS TO KETONES. SENSITIVITY OF THE REACTION TO THE NATURE OF THE PHASE TRANSFER AGENT.

Januszkiewicz, Krzysztof,Alper, Howard

, p. 5159 - 5162 (1983)

Terminal olefins can be converted to ketones in good yields, and under mild conditions, using phase transfer catalysis; the quaternary ammonium salt governs the course of the react ion.

-

Lochow,Miller

, p. 3020 (1976)

-

Production of renewable 1,3-pentadiene over LaPO4 via dehydration of 2,3-pentanediol derived from 2,3-pentanedione

Bai, Chenxi,Cui, Long,Dai, Quanquan,Feng, Ruilin,Liu, Shijun,Qi, Yanlong

, (2022/02/07)

1,3-Pentadiene plays an extremely important role in the production of polymers and fine chemicals. Herein, the LaPO4 catalyst exhibits excellent catalytic performance for the dehydration production of 1,3-pentadiene with 2,3-pentanediol, a C5 diol platform compound that can be easily obtained by hydrogenation of bio-based 2,3-pentanedione. The relationships of catalyst structure-acid/base properties-catalytic performance was established, and an acid-base synergy effect was disclosed for the on-purpose synthesis of 1,3-pentadiene. Thus, a balance between acid and base sites was required, and an optimized LaPO4 with acid/base ratio of 2.63 afforded a yield of 1,3-pentadiene as high as 61.5% at atmospheric pressure. Notably, the Br?nsted acid sites with weak or medium in LaPO4 catalyst can inhibit the occurrence of pinacol rearrangement, resulting in higher 1,3-pentadiene production. In addition, the investigation on reaction pathways demonstrated that the E2 mechanism was dominant in this dehydration reaction, accompanied by the assistance of E1 and E1cb.

A Synergistic Magnetically Retrievable Inorganic-Organic Hybrid Metal Oxide Catalyst for Scalable Selective Oxidation of Alcohols to Aldehydes and Ketones

Mittal, Rupali,Awasthi, Satish Kumar

, p. 4799 - 4813 (2021/09/30)

Herein, we report a synergistic silica coated magnetic Fe3O4 catalyst functionalized with nitrogen rich organic moieties and immobilized with cobalt metal ion (FNP-5) for selective oxidation of alcohols to aldehydes and ketones using tert-butyl hydroperoxide (TBHP) as oxidant. The catalyst was rigorously characterized via several techniques which delineate its core-shell structure, magnetic behavior, phase and crystal structure. The Co(III) acts as the active catalytic center for selective oxidation reaction. The control reactions revealed radical mechanistic pathway assisted by the synergism induced by the inorganic-organic hybrid nature of FNP-5. The other features of current protocol involve neat reaction conditions, high TOF values, scalability of product and low E-factor value (1.92). Moreover, FNP-5 could be effortlessly separated via an external magnet, displays recyclability over eight catalytic cycles and exhibits structural integrity even after rigorous use. Overall, these results manifest the understanding of synergistic architectures as sustainable surrogates for selective oxidation reactions.

Hydration of Alkynes to Ketones with an Efficient and Practical Polyoxomolybdate-based Cobalt Catalyst

Xie, Ya,Wang, Jingjing,Wang, Yunyun,Han, Sheng,Yu, Han

, p. 4985 - 4989 (2021/10/12)

Hydration of alkynes to ketones is one of the most atom economical and universal methods for the synthesis of carbonyl compounds. However, the basic reaction usually requires organic ligand catalysts or harsh reaction conditions to insert oxygen into the C≡C bond. Here, we report an inorganic ligand supported cobalt (III) catalyst, (NH4)3[CoMo6O18(OH)6], which is supported by a central cobalt (III) mononucleus and a ring-shaped pure inorganic ligand composed of six MoVIO6 octahedrons to avoid the disadvantages of expensive and unrecyclable organic ligand catalysts or noble metal catalysts. Under mild conditions, the cobalt (III) catalyst can be used for the hydration of alkynes to ketones. The catalyst is non-toxic, green, and environment friendly. The catalyst can be recycled at least six times with high activity. According to control experiments, a reasonable mechanism is provided.

Chromium-Catalyzed Production of Diols From Olefins

-

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.

Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor

Morimoto, Mariko,Cao, Wendy,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean

supporting information, p. 2108 - 2114 (2021/02/06)

Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.

Process route upstream and downstream products

Process route

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;
diethyl ether
60-29-7,927820-24-4

diethyl ether

2-ethyl-1-phenyl-1,3-butanedione
39581-96-9

2-ethyl-1-phenyl-1,3-butanedione

2-ethyl-1-phenyl-butane-1,3-diol

2-ethyl-1-phenyl-butane-1,3-diol

benzaldehyde
100-52-7

benzaldehyde

2-Pentanone
107-87-9

2-Pentanone

propiophenone
495-40-9

propiophenone

Conditions
Conditions Yield
at 60 ℃; under 110326 - 147102 Torr; Hydrogenation;
(+/-)-2-pentanol
6032-29-7,13403-73-1

(+/-)-2-pentanol

(S)-2-pentanol
26184-62-3

(S)-2-pentanol

(R)-2-pentanol
31087-44-2,13403-73-1

(R)-2-pentanol

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
With whole lyophilised cells of Rhodococcus ruber DSM; acetone; In phosphate buffer; at 30 ℃; for 38h; pH=8.0;
With [bis(acetoxy)iodo]benzene; potassium bromide; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese; In dichloromethane; at 20 ℃; for 1h; Further Variations:; Solvents; Product distribution; Kinetics;
With [bis(acetoxy)iodo]benzene; potassium bromide; In dichloromethane; water; at 20 ℃; for 1h; Title compound not separated from byproducts.;
With NADP; In acetone; at 50 ℃; for 22h; pH=8; Resolution of racemate;
(+/-)-2-pentanol; With 36Zn(2+)*6O(2-)*12C40H44O12S4(4-)*12Mn(3+)*12C30H34N2O6(4-)*21H2O*38C3H7NO; In dichloromethane; water; for 0.0833333h; Resolution of racemate;
With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide; In dichloromethane; water; at 0 ℃; for 0.5h; Reagent/catalyst; Optical yield = 86 %ee; enantioselective reaction;
(+/-)-2-pentanol
6032-29-7,13403-73-1

(+/-)-2-pentanol

(S)-2-pentanol
26184-62-3

(S)-2-pentanol

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
(+/-)-2-pentanol; With Br(1-)*C75H107Cl2Mn2N8O4(1+); potassium bromide; In dichloromethane; water; at 20 ℃; for 0.166667h;
With [bis(acetoxy)iodo]benzene; In dichloromethane; water; optical yield given as %ee;
3-penten-2-ol
1569-50-2

3-penten-2-ol

2,2,2-trifluoroethyl dodecanoate
70253-78-0

2,2,2-trifluoroethyl dodecanoate

(S)-2-pentanol
26184-62-3

(S)-2-pentanol

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
With porcine pancreatic lipase; hydrogen; Yield given. Multistep reaction; 1.) Et2O, 78 h, 2.) 5percent Pd-C, 20.75 h;
10%
Cyclopropyl methyl ketone
765-43-5

Cyclopropyl methyl ketone

(S)-2-pentanol
26184-62-3

(S)-2-pentanol

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
at 80 - 160 ℃; under 95616 Torr; Hydrogenation;
2-methylfuran
534-22-5

2-methylfuran

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

(S)-2-pentanol
26184-62-3

(S)-2-pentanol

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
at 150 ℃; Hydrogenation;
ethene
74-85-1

ethene

acetone
67-64-1

acetone

pent-4-en-2-one
13891-87-7

pent-4-en-2-one

3-penten-2-one
625-33-2

3-penten-2-one

hept-6-en-2-one
21889-88-3

hept-6-en-2-one

4-oxopentyl acetate
5185-97-7

4-oxopentyl acetate

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
With copper diacetate; manganese triacetate; In acetic acid; at 85 ℃; for 4h; under 38000 Torr; Product distribution; Mechanism; other solvents, var. conc. of reagents, var. pressure, var. reagent (MnO2);
10 % Turnov.
18 % Turnov.
30 % Turnov.
28 % Turnov.
14 % Turnov.
1-methylcyclobutanol
20117-47-9

1-methylcyclobutanol

decane-2,9-dione
16538-91-3

decane-2,9-dione

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
With manganese triacetate; In acetic acid; at 100 ℃; for 0.05h;
36%
1-methylcyclobutanol
20117-47-9

1-methylcyclobutanol

1,3-diacetoxypropane
628-66-0

1,3-diacetoxypropane

decane-2,9-dione
16538-91-3

decane-2,9-dione

2-Pentanone
107-87-9

2-Pentanone

Conditions
Conditions Yield
With manganese triacetate; In acetic acid; at 100 ℃; for 0.05h;
36%
41%

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