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Cas Database

71-23-8

71-23-8

Identification

  • Product Name:1-Propanol

  • CAS Number: 71-23-8

  • EINECS:200-746-9

  • Molecular Weight:60.0959

  • Molecular Formula: C3H8O

  • HS Code:2905121000

  • Mol File:71-23-8.mol

Synonyms:Propylalcohol (8CI);1-Hydroxypropane;Ethylcarbinol;NSC 30300;Optal;Osmosolextra;Propanol;n-Propanol;n-Propyl alcohol;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF, IrritantXi

  • Hazard Codes: F:Flammable;

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH318 Causes serious eye damage H336 May cause drowsiness or dizziness

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. 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 Rinse mouth. Refer for medical attention . Contact with eyes is extremely irritating and may cause burns. Vapors irritate nose and throat. In high concentrations, may cause nausea, dizziness, headache, and stupor. (USCG, 1999) Basic Treatment: Establish a patent airway. Suction if necessary Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Lower alcohols (1-3 Carbons) and related compounds/

  • Fire-fighting measures: Suitable extinguishing media To fight fire use alcohol foam, carbon dioxide, dry chemical. Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: 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. (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. Ventilation. Remove all ignition sources. 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. Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.

  • 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 strong oxidants. Cool. Well closed. Keep in a well-ventilated room.Keep containers closed, store in cool, well ventilated place away from ignition sources.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 200 ppm (500 mg/cu m).Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 250 ppm (625 mg/cu m) [skin].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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Relevant articles and documentsAll total 699 Articles be found

Hydrogenation catalysts based on platinum- and palladium-containing nanodiamonds

Magdalinova,Kalmykov,Klyuev

, p. 33 - 39 (2014)

Platinum and palladium nanoparticles of 4-5 nm size applied at nanodiamonds have been shown to efficiently catalyze liquid-phase hydrogenation of different organic compounds (nitrocompounds, azomethines, and unsaturated hydrocarbons and alcohols) under mild conditions (T = 318 K, hydrogen pressure of 0.1 MPa, solution in ethanol). Using of palladium on nanodiamond containing 3 wt % of metal has been most efficient.

Hydrogenation of unsaturated compounds in the presence of palladium-containing modified carbon nanofibers

Osipov,Klyuev

, p. 928 - 931 (2013)

Palladium-containing carboxylated carbon nanofibers were studied as catalysts for hydrogenation of double bond >C=C in olefins, unsaturated alcohols, and acids, as well as for hydrogenation of nitroarenes. The developed catalyst is 7 times more efficient than the industrial analog (Pd/C).

Preparation of highly active heterogeneous Au@Pd bimetallic catalyst using plant tannin grafted collagen fiber as the matrix

Ma, Jun,Huang, Xin,Liao, Xuepin,Shi, Bi

, p. 8 - 16 (2013)

Au@Pd bimetallic nanoparticles (NPs) catalysts were synthesized by a seeding growth method using bayberry tannin grafted collagen fiber (BT-CF) as the matrix. In this method, Au3+ was first reductively adsorbed onto BT-CF to form Au NPs, and then they serve as the seeds for the over growth of Pd shell. The morphology of BT-CF-Au@Pd catalyst was observed by TEM and SEM, and the core-shell structure of the Au@Pd was confirmed by EDS and XRD. It was found that the as-prepared BT-CF-Au9@Pd3 catalyst showed excellent synergy effect in liquid-phase hydrogenation of cyclohexene, whose reaction time was three times faster than that catalyzed by BT-CF-Pd catalyst under the same conditions. Meanwhile, the BT-CF-Au9@Pd3 catalyst could be re-used four times without significant loss of activity. In the fourth run, the substrate conversion was still as high as 92.70%, much better than that by using commercial Pd/C catalyst (42.60%). Additionally, BT-CF-Au9@Pd3 catalyst exhibited high hydrogenation activity to various alkenes and nitro-compounds. For example, the TOF of allyl alcohol, styrene and nitrobenzene hydrogenations reached 10,980, 14,732 and 1379 mol mol-1 h-1, respectively.

An Innovative Approach for Highly Selective Direct Conversion of CO2into Propanol using C2H4and H2

Ahlers, Stefan J.,Bentrup, Ursula,Linke, David,Kondratenko, Evgenii V.

, p. 2631 - 2639 (2014)

Multifunctional catalysts are developed for converting CO2with C2H4and H2into propanol. Au nanoparticles (NP) supported on TiO2are found to facilitate this reaction. The activity and selectivity strongly depend on NP size, which can be tuned by the method of Au deposition and by promoting with K. The promoter improves the selectivity to propanol. Under optimized reaction conditions (2 MPa, 473 K, and CO2/H2/C2H4=1:1:1), CO2is continuously converted into propanol with a near-to-100 % selectivity. Catalytic tests as well as mechanistic studies by in situ FTIR and temporal analysis of products with isotopic tracers allow the overall reaction scheme to be determined. Propanol is formed through a sequence of reactions starting with reverse water–gas shift to reduce CO2to CO, which is further consumed in the hydroformylation of ethylene to propanal. The latter is finally hydrogenated to propanol, while propanol hydrogenation to propane is suppressed.

Pd nanoparticles immobilized on boehmite by using tannic acid as structure-directing agent and stabilizer: A high performance catalyst for hydrogenation of olefins

Liu, Jing,Liao, Xuepin,Shi, Bi

, p. 249 - 258 (2014)

Boehmite-supported Pd nanoparticles (Pd-TA-boehmite) were successfully synthesized by a hydrothermal method using tannic acid as the structure-directing agent as well as stabilizer. The physicochemical properties of the Pd-TA-boehmite catalyst were well characterized by XPS, XRD, N 2 adsorption/desorption, and TEM analyses. Catalytic hydrogenation of olefins was used as the probe reaction to evaluate the activity of the Pd-TA-boehmite catalyst. For comparison, the Pd-boehmite catalyst prepared without tannic acid was also employed for olefin hydrogenation. For all the investigated substrates, the Pd-TA-boehmite catalyst exhibited superior catalytic performance than the Pd-boehmite catalyst. For the example of hydrogenation of allyl alcohol, the initial hydrogenation rate and selectivity of the Pd-TA-boehmite catalyst were 23,520 mol/mol h and 99 %, respectively, while those of the Pd-boehmite catalyst were only 14,186 mol/mol h and 93 %, respectively. Additionally, the hydrogenation rate of the Pd-TA-boehmite catalyst could still reach 20,791 mol/mol h at the 7th cycle, which was much higher than that of the Pd-boehmite catalyst (5,250 mol/mol h) at the 4th cycle, thus showing an improved reusability.

Hydrogenation of Propoinaldehyde by Nickel Catalysts Supported on Al2O3, SiO2, TiO2, Ta2O5, and Nb2O5

Funakoshi, Masaki,Inoue, Hakuaki

, p. 1205 - 1208 (1987)

The hydrogenation of propionaldehyde with various nickel catalysts was studied kinetically for a wide range of reaction conditions.The catalysts were supported on Al2O3, SiO2, TiO2, Ta2O5, and Nb2O5.The reaction rates were well correlated with the irreversibly adsorbed hydrogen uptakes.A detailed analysis concluded that this reaction was structure-insensitive under all reaction conditions tested.

Solvent Effects in the Homogeneous Catalytic Reduction of Propionaldehyde with Aluminium Isopropoxide Catalyst: New Insights from PFG NMR and NMR Relaxation Studies

Muhammad, Atika,Di Carmine, Graziano,Forster, Luke,D'Agostino, Carmine

, p. 1101 - 1106 (2020)

Solvent effects in homogeneous catalysis are known to affect catalytic activity. Whilst these effects are often described using qualitative features, such as Kamlet-Taft parameters, experimental tools able to quantify and reveal in more depth such effects have remained unexplored. In this work, PFG NMR diffusion and T1 relaxation measurements have been carried out to probe solvent effects in the homogeneous catalytic reduction of propionaldehyde to 1-propanol in the presence of aluminium isopropoxide catalyst. Using data on diffusion coefficients it was possible to estimate trends in aggregation of different solvents. The results show that solvents with a high hydrogen-bond accepting ability, such as ethers, tend to form larger aggregates, which slow down the molecular dynamics of aldehyde molecules, as also suggested by T1 measurements, and preventing their access to the catalytic sites, which results in the observed decrease of catalytic activity. Conversely, weakly interacting solvents, such as alkanes, do not lead to the formation of such aggregates, hence allowing easy access of the aldehyde molecules to the catalytic sites, resulting in higher catalytic activity. The work reported here is a clear example on how combining traditional catalyst screening in homogeneous catalysis with NMR diffusion and relaxation time measurements can lead to new physico-chemical insights into such systems by providing data able to quantify aggregation phenomena and molecular dynamics.

Highly efficient hydrogenation of methyl propionate to propanol over hydrous zirconia supported ruthenium

Fan, Guangyin,Zhou, Yafen,Fu, Haiyan,Ye, Xiaoli,Li, Ruixiang,Chen, Hua,Li, Xianjun

, p. 229 - 236 (2011)

Hydrous zirconia supported ruthenium catalyst Ru/ZrO2? xH2O, prepared by co-precipitating ruthenium trichloride and zirconium oxychloride with ammonia, was able to catalyze efficiently methyl propionate to propanol under the mild conditions. In aqueous system, the propanol yield of >99% was achieved under the conditions of reaction temperature of 150 °C and hydrogen pressure of 5.0 MPa, while in non-aqueous system the maximum propanol yield was only 47.0%. FTIR spectra and hydrogenation results indicated that the high catalytic performance of Ru/ZrO2?xH2O in aqueous phase results from the cooperation effect between water as a solvent and hydroxyl groups on the surface of carrier.

Palladium-containing nanodiamonds in hydrogenation and hydroamination

Magdalinova,Kalmykov,Klyuev

, p. 299 - 304 (2012)

Palladium catalysts in the form of Pd nanoparticles supported on nanodiamonds have been studied in the hydrogenation of nitrobenzene, allyl alcohol, and cyclohexene and in the hydrogenating amination of propanal with 4-aminobenzoic acid. The ratio of two valence states of palladium, i.e., Pd 2+ and Pd0, in the catalysts has been determined by XPS. The dependence of hydrogenation reaction rate on electron density at the reaction site of nitrobenzene, allyl alcohol, cyclohexene, and 4-(propylideneamino)benzoic acid molecules has been studied using quantum chemical calculations (HF/6-31G, PCM). Pleiades Publishing, Ltd., 2012.

-

Kepner et al.

, p. 88 (1954)

-

Sulphonated "click" dendrimer-stabilized palladium nanoparticles as highly efficient catalysts for olefin hydrogenation and Suzuki coupling reactions under ambient conditions in aqueous media

Ornelas, Catia,Ruiz, Jaime,Salmon, Lionel,Astruc, Didier

, p. 837 - 845 (2008)

Water-soluble 1,2,3-triazolyl dendrimers were synthesized by "click chemistry" and used to stabilize palladium nanoparticles (PdNPs). These new "click" dendrimer-stabilized nanoparticles (DSN) are highly stable to air and moisture and are catalytically active for olefin hydrogenation and Suzuki coupling reaction, in aqueous media, under ambient conditions using a low amount of palladium (0.01 mol% Pd). Kinetic studies show high catalytic efficiency and high stability for the new "click" DSN in both reactions. The complexation of potassium tetrachloropalladate (K 2PdCl4) to the triazole ligands present in the dendritic structures was monitored by UV/vis and, after reduction, the nanoparticles were characterized by transmission electron microscopy (TEM).

Efficient hydrogenation of methyl propionate over bnehmite-Supported Ru-Pt catalyst

Zhou, Ya-Fen,Wei, Juan,Fan, Guang-Yin,Fu, Hai-Yan,Li, Rui-Xiang,Chen, Hua,Li, Xian-Jun

, p. 1034 - 1035 (2009)

The bimetallic catalyst Ru-Pt/AlOOH exhibited good catalytic performance in water for the hydrogenation of methyl propionate to 1-propanol. The selectivity to 1-propanol of 97.8% was obtained with a conversion of 89.1% at 453 K, 5MPa for 6 h. The incorporation of Pt for the improvement of the catalystic activity was attributed to promoting the reduction of Ru3+ to Ru0. Copyright

Pt-And Pd-containing nanodiamonds in hydrogenation and hydroamination reactions1

Magdalinova,Klyuev,Vershinin,Efimov

, p. 482 - 485 (2012)

The catalytic activity of platinum-And palladium-containing nanodiamonds has been investi-gated in liquid-phase nitrobenzene, allyl alcohol, and cyclohexene hydrogenation and propanal hydroami-nation with 4-Aminobenzoic acid as model reactions. The catalysts suggested are significantly more active than commercial Pd/C. The catalysts with a low metal weight content are the most effective in liquid phase catalytic hydrogenation. Pleiades Publishing, Ltd., 2012.

Towards the upgrading of fermentation broths to advanced biofuels: A water tolerant catalyst for the conversion of ethanol to isobutanol

Pellow, Katy J.,Wingad, Richard L.,Wass, Duncan F.

, p. 5128 - 5134 (2017)

Isobutanol is an ideal gasoline replacement due to its high energy density, suitable octane number and compatibility with current engine technology. It can be formed by the Guerbet reaction in which (bio)ethanol and methanol mixtures are converted to this higher alcohol in the presence of a suitable catalyst under basic conditions. A possible limitation of this process is the catalyst's water tolerance; a twofold problem given that water is produced as a by-product of the Guerbet reaction but also due to the need to use anhydrous alcoholic feedstocks, which contributes significantly to the cost of advanced biofuel production. Isobutanol formation with pre-catalyst trans-[RuCl2(dppm)2] (1) has been shown to be tolerant to the addition of water to the system, achieving an isobutanol yield of 36% at 78% selectivity with water concentrations typical of that of a crude fermentation broth. Key to this success is both the catalyst's tolerance to water itself and the use of a hydroxide rather than an alkoxide base; other catalysts explored are less effective with hydroxides. Alcoholic drinks have also been used as surrogates for the fermentation broth: the use of lager as the ethanol source yielded 29% isobutanol at 85% selectivity in the liquid phase.

Inverse Bimetallic RuSn Catalyst for Selective Carboxylic Acid Reduction

Vorotnikov, Vassili,Eaton, Todd R.,Settle, Amy E.,Orton, Kellene,Wegener, Evan C.,Yang, Ce,Miller, Jeffrey T.,Beckham, Gregg T.,Vardon, Derek R.

, p. 11350 - 11359 (2019)

Inverse bimetallic catalysts (IBCs), synthesized by sequential deposition of noble and oxophilic metals, offer potential reactivity enhancements to various reactions, including the reduction of carboxylic acids for renewable fuels and chemicals. Here, we demonstrate that an IBC comprising RuSn exhibits high selectivity for propionic acid reduction to 1-propanol, while Ru alone results in cracking. On RuSn, X-ray absorption spectroscopy identified Ru0 nanoparticles with a near-surface bimetallic Ru0Sn0 alloy and small SnOx domains. Corresponding model surfaces were examined with density functional theory to elucidate the observed selectivity difference. Only selective hydrogenation is predicted to be favorable on SnOx/Ru, with the SnOx clusters facilitating C-OH scission and Ru enabling hydrogen activation. Intrinsic barriers along nonselective pathways suggest that the RuSn alloy and SnOx resist cracking. SnOx/Ru hydrogenation activity was supported experimentally by inhibiting hydrogenation with phenylphosphonic acid, differentiating the system from fully alloyed RuSn metallic nanoparticles. Overall, this work demonstrates a plausible mechanism for selective reduction of carboxylic acids and proposes a roadmap for rational design of IBCs.

Peptide-modified dendrimers as templates for the production of highly reactive catalytic nanomaterials

Bedford, Nicholas M.,Bhandari, Rohit,Slocik, Joseph M.,Seifert, Soenke,Naik, Rajesh R.,Knecht, Marc R.

, p. 4082 - 4091 (2014)

Peptide-driven nanomaterials synthesis and assembly has become a significant research thrust due to the capability to generate a range of multifunctional materials with high spatial precision and tunable properties. Despite the extensive amount of available literature, the majority of studies report the use of free peptides to drive synthesis and assembly. Such strategies are not an entirely accurate representation of nature, as many materials binding peptides found in biological systems are sterically constrained to a larger biological motif. Herein we report the synthesis of catalytic Pd nanomaterials using constrained peptides covalently attached to the surface of small, water-soluble dendrimers. Using the R5 peptide conjugated to polyamidoamine dendrimer as a bioconjugate, Pd nanomaterials were generated that displayed altered morphologies compared to nanomaterials templated with free R5. It was discovered that the peptide surface density on the dendrimer affected the resulting nanoscale morphology. Furthermore, the catalytic activities of Pd materials templated with R5/dendrimer are higher as compared to the R5-templated Pd materials for the hydrogenation of allyl alcohol, with an average increase in turnover frequency of ~1500 mol product (mol Pd × h)-1. Small angle X-ray scattering analysis and dynamic light scattering indicate that Pd derived from R5/dendrimer templates remained less aggregated in solution and displayed more available reactive Pd surface area. Such morphological changes in solution are attributed to the constrained peptide binding motifs, which altered the Pd morphology and subsequent properties. Moreover, the results of this study suggest that constrained materials binding peptide systems can be employed as a means to alter morphology and improve resulting properties.

-

Edson

, p. 1855 (1936)

-

-

Lee,Gruber

, p. 3775 (1968)

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Size-selective hydrogenation of olefins by Dendrimer-encapsulated palladium nanoparticles

Niu,Yeung,Crooks

, p. 6840 - 6846 (2001)

Nearly monodisperse (1.7 ± 0.2 nm) palladium nanoparticles were prepared within the interiors of three different generations of hydroxyl-terminated poly(amidoamine) (PAMAM) dendrimers. These dendrimer-encapsulated catalysts (DECs) were used to hydrogenate allyl alcohol and four α-substituted derivatives in a 4:1 methanol/water mixture. The results indicate that steric crowding on the dendrimer periphery, which increases with dendrimer generation, can act as an adjustable-mesh nanofilter. That is, by controlling the packing density on the dendrimer periphery, it is possible to control access of substrates to the encapsulated catalytic nanoparticle. In general, higher-generation DECs or larger substrates resulted in lower turnover frequencies (although some interesting exceptions were noted). Although the main products of the olefin hydrogenation reactions were the corresponding alkanes, ketones were also obtained when monosubstituted α-olefins were used as substrates. NMR spectroscopy was used to measure the size selectivity of DECs for the competitive hydrogenation of allyl alcohol and 3-methyl-1-penten-3-ol. The effect on catalytic rate as a function of nanoparticle size is also briefly discussed.

HYDROGENATION CATALYSIS BY PALLADIUM CLUSTER COMPLEXES WITH PHENANTHROLINE

Berenblyum, A. S.,Mund, S. L.,Goranskaya, T. P.,Moiseev, I. I.

, p. 2041 - 2044 (1981)

-

HOMOGENEOUS HYDROGENATION OF ALDEHYDES TO ALCOHOLS WITH RUTHENIUM COMPLEX CATALYSTS

Sanchez-Delgado, R.A.,Andriollo, A.,Ochoa, O.L. De,Suarez, T.,Valencia, N.

, p. 77 - 83 (1981)

A number of ruthenium complexes catalyse the reduction of aldehydes to their corresponding alcohols in toluene solution under mild reaction conditions.The most convenient catalyst precursor is hydridochlorocarbonyltris(triphenylphosphine)ruthenium(II).Turnover numbers up to 32 000 have been achieved with this catalyst.The rate of hydrogenation is first order with respect to the substrate concentration, the catalyst concentration and the hydrogen pressure, and is also affected by acid and basic additives.

Catalytic conversion of methanol/ethanol to isobutanol - A highly selective route to an advanced biofuel

Wingad, Richard L.,Bergstr?m, Emilie J. E.,Everett, Matthew,Pellow, Katy J.,Wass, Duncan F.

, p. 5202 - 5204 (2016)

Catalysts based on ruthenium diphosphine complexes convert methanol/ethanol mixtures to the advanced biofuel isobutanol, with extremely high selectivity (>99%) at good (>75%) conversion via a Guerbet-type mechanism.

Nanoconfinement Engineering over Hollow Multi-Shell Structured Copper towards Efficient Electrocatalytical C?C coupling

Li, Jiawei,Liu, Chunxiao,Xia, Chuan,Xue, Weiqing,Zeng, Jie,Zhang, Menglu,Zheng, Tingting

supporting information, (2021/12/06)

Nanoconfinement provides a promising solution to promote electrocatalytic C?C coupling, by dramatically altering the diffusion kinetics to ensure a high local concentration of C1 intermediates for carbon dimerization. Herein, under the guidance of finite-element method simulations results, a series of Cu2O hollow multi-shell structures (HoMSs) with tunable shell numbers were synthesized via Ostwald ripening. When applied in CO2 electroreduction (CO2RR), the in situ formed Cu HoMSs showed a positive correlation between shell numbers and selectivity for C2+ products, reaching a maximum C2+ Faradaic efficiency of 77.0±0.3 % at a conversion rate of 513.7±0.7 mA cm?2 in a neutral electrolyte. Mechanistic studies clarified the confinement effect of HoMSs that superposition of Cu shells leads to a higher coverage of localized CO adsorbate inside the cavity for enhanced dimerization. This work provides valuable insights for the delicate design of efficient C?C coupling catalysts.

MOF-derived hcp-Co nanoparticles encapsulated in ultrathin graphene for carboxylic acids hydrogenation to alcohols

Dong, Mei,Fan, Weibin,Gao, Xiaoqing,Zhu, Shanhui

, p. 201 - 211 (2021/06/03)

Highly efficient conversion of carboxylic acids to valuable alcohols is a great challenge for easily corroded non-noble metal catalysts. Here, a series of few-layer graphene encapsulated metastable hexagonal closed-packed (hcp) Co nanoparticles were fabricated by reductive pyrolysis of metal-organic framework precursor. The sample pyrolyzed at 400 °C (hcp-Co@G400) presented outstanding performance and stability for converting a variety of functional carboxylic acids and its turnover frequency was one magnitude higher than that of conventional facc-centered cubic (fcc) Co catalysts. In situ DRIFTS spectroscopy of model reaction acetic acid hydrogenation and DFT calculation results confirm that carboxylic acid initially undergoes dehydroxylation to RCH2CO* followed by consecutive hydrogenation to RCH2CH2OH through RCH2COH*. Acetic acid prefers to vertically adsorb at hcp-Co (0 0 2) facet with a much lower adsorption energy than parallel adsorption at fcc-Co (1 1 1) surface, which plays a key role in decreasing the activation barrier of the rate-determining step of acetic acid dehydroxylation.

METHOD FOR PRODUCING BIO ALCOHOL FROM INTERMEDIATE PRODUCTS OF ANAEROBIC DIGESTION TANK

-

Paragraph 0057-0060; 0063; 0065-0066; 0068-0069; 0071, (2021/05/25)

The present invention relates to a method for producing a bio-alcohol by reacting a mixture of volatile fatty acid with methanol in 2 through 11 in a reactor in the presence of a 280 °C-membered alkaline earth metal catalyst or 400 °C transition metal catalyst formed based on a support.

Synthesis, crystal and structural characterization, Hirshfeld surface analysis and DFT calculations of three symmetrical and asymmetrical phosphonium salts

Delaram, Behnaz,Gholizadeh, Mostafa,Makari, Faezeh,Nokhbeh, Seyed Reza,Salimi, Alireza

, (2021/07/01)

Three stable phosphonium salts of 1,4-butanediylebis(triphenylphosphonium) dibromide I, butane-4?bromo-1-(triphenylphosphonium) bromide II and 1,3-propanediylbis(triphenylphosphonium) tetrahydroborate III were synthesized and structurally characterized. Single crystal X-ray diffraction analysis, spectroscopic methods and thermal analysis methods were used for the characterization of titled compounds. Crystallographic data showed that compound I crystallized in the triclinic crystal system with Pī space group and compound II crystallized in the monoclinic crystal system with P21/c space group. The crystal packing structures of I and II were stabilized by various intermolecular interactions, especially of C–H···π contacts. The molecular Hirshfeld surface analysis and 2D fingerprint revealed that the C···H contacts have 24.3% and 18.4% contributions in the crystal packings of compounds I and II, respectively. In addition, the H···Br (28.5%) contact has a considerable contribution to the crystal architecture of compound II. Theoretical studies were performed by DFT method to investigate the structural properties of the titled compounds. The isotopic ratio of boron in tetrahydroborate anion of compound III calculated by 1H NMR spectroscopy. The isotopic ratio for 10B/11B was 19.099 / 80.900%. Reduction of some carbonyl compounds to corresponding alcohols was performed by compound III and the optimum conditions were determined.

Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions

Sharifi, Sina,Sharifi, Hannah,Koza, Darrell,Aminkhani, Ali

, p. 803 - 808 (2021/07/20)

Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH2 or CH3 adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl3/Et3N in CH2Cl2, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl3 content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction. Graphic abstract: [Figure not available: see fulltext.].

Process route upstream and downstream products

Process route

C<sub>9</sub>H<sub>11</sub>NO<sub>3</sub>S
130436-14-5

C9H11NO3S

propan-1-ol
71-23-8

propan-1-ol

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

1-(ethylsulfanyl)-4-nitrobenzene
7205-60-9

1-(ethylsulfanyl)-4-nitrobenzene

propionaldehyde
123-38-6

propionaldehyde

Conditions
Conditions Yield
In benzene; Product distribution; Irradiation;
α-cyclodextrin-1-propanol complex
64415-06-1

α-cyclodextrin-1-propanol complex

propan-1-ol
71-23-8

propan-1-ol

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

Conditions
Conditions Yield
at 25 ℃; Equilibrium constant; binding of cyclodextrins to various guests; formation of 1:1 complexes; dissociation constants of CD-guest complexes; effect of guest alcohols on the CD-retarded hydrolysis of benzaldehyde dimethyl acetal;
bromosulfurous acid propyl ester

bromosulfurous acid propyl ester

water
7732-18-5

water

propan-1-ol
71-23-8

propan-1-ol

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

Conditions
Conditions Yield
dimethyl cis-but-2-ene-1,4-dioate
624-48-6

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

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

1-methoxy-1,4-butanediol

1-methoxy-1,4-butanediol

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

2-(4'-hydroxybutoxy)-tetrahydrofuran

4-hydroxy-butanoic acid 4-hydroxybutyl ester

4-hydroxy-butanoic acid 4-hydroxybutyl ester

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

Butane-1,4-diol

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

methyl 4-hydroxybutanoate
925-57-5

methyl 4-hydroxybutanoate

butan-1-ol
71-36-3

butan-1-ol

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

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

2-methoxytetrahydrofuran
13436-45-8

2-methoxytetrahydrofuran

4-butanolide
96-48-0

4-butanolide

propan-1-ol
71-23-8

propan-1-ol

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

2-(4'-hydroxybutoxy)-tetrahydrofuran

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

Butane-1,4-diol

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich; at 150 - 280 ℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);
98%
1%
0.4%
0.5%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

allyl alcohol
107-18-6

allyl alcohol

2-ethoxytetrahydrofuran
13436-46-9

2-ethoxytetrahydrofuran

propan-1-ol
71-23-8

propan-1-ol

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

Butane-1,4-diol

1,1-diethoxypropane
4744-08-5

1,1-diethoxypropane

Conditions
Conditions Yield
With hydrogen; acetylacetonatodicarbonylrhodium(l); at 125 ℃; for 2.5h; under 30003 Torr; Further Variations:; reagent ratios; Product distribution;
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;
propan-1-ol
71-23-8

propan-1-ol

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

propylene glycol

ethanol
64-17-5

ethanol

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

hydrogen
1333-74-0

hydrogen

Conditions
Conditions Yield
With prereduced 3 wtpercent Pt-Ir alloy particle covered with ReOx supported on silica; In water; at 189.84 ℃; for 4h; under 15001.5 Torr; Inert atmosphere; Autoclave;
3-Phenylpropenol
104-54-1

3-Phenylpropenol

propan-1-ol
71-23-8

propan-1-ol

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

Conditions
Conditions Yield
3-Phenylpropenol; With Hoveyda-Grubbs catalyst second generation; ethene; In toluene; at 80 ℃; for 2h; under 760.051 Torr; Schlenk technique;
With potassium hydroxide; tricyclohexylphosphine; In toluene; at 110 ℃; for 48h; Schlenk technique; Inert atmosphere;
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;

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