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Cas Database

60-29-7

60-29-7

Identification

  • Product Name:Diethyl ether

  • CAS Number: 60-29-7

  • EINECS:200-467-2

  • Molecular Weight:74.1228

  • Molecular Formula: C4H10O

  • HS Code:2909 11 00

  • Mol File:60-29-7.mol

Synonyms:Ether(6CI);Ethyl ether (8CI);1,1'-Oxybisethane;3-Oxapentane;Anaesthetic ether;Anesthesia ether;Anesthetic ether;Diethyl oxide;Ethoxyethane;Ethyl oxide;NSC 100036;Pronarcol;Sulfuric ether;Ethyl ether;Ethane, 1,1'-oxybis-;

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Safety information and MSDS view more

  • Pictogram(s):HighlyF+, HarmfulXn, ToxicT

  • Hazard Codes:F+,Xn,T,F

  • Signal Word:Danger

  • Hazard Statement:H224 Extremely flammable liquid and vapourH302 Harmful if swallowed 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. Artificial respiration may be needed. 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. Give one or two glasses of water to drink. Refer for medical attention . Vapor inhalation may cause headache, nausea, vomiting, and loss of consciousness. Contact with eyes will be irritating. Skin contact from clothing wet with the chemical may cause burns. (USCG, 1999) INHALATION: Cough. Sore throat. Drowsiness. Vomiting. Headache. Labored breathing. Unconsciousness. First aid: Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. SKIN: Symptoms: Dry skin. 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: Dizziness. Drowsiness. Vomiting. First aid: Rinse mouth. Do NOT induce vomiting. Give plenty of water to drink. Refer for medical attention.

  • Fire-fighting measures: Suitable extinguishing media Water may be ineffective ... But water should be used to keep fire-exposed containers cool. Use water spray dry chemical, foam, or carbon dioxide. Behavior in Fire: Vapor is heavier than air and may travel considerable distance to a source of ignition and flash back. Decomposes violently when heated. (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. Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Spills and leakage: Absorb with paper. Evaporate completely all spilt surface. Dispose by burning the paper after complete ventilation of vapor.

  • 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. See Chemical Dangers. Cool. Keep in the dark. Store only if stabilized.Separate from oxidizing materials. Store in a cool, dry, well-ventilated area. Avoid sunlight.

  • Exposure controls/personal protection:Occupational Exposure limit valuesNIOSH questioned whether the PEL proposed by OSHA for ethyl ether [TWA 400 ppm; STEL 500 ppm] was adequate to protect workers from recognized health hazards.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 441 Articles be found

Ethylation of Ethanol in the Gas Phase

Audier, H. E.,Monteiro, C.,Robin, D.

, p. 146 (1989)

-

Novel amorphous mesoporous 0.25Cr2O3–0.75ZrO2nanomaterials synthesized by a surfactant-assisted hydrothermal method for ethanol oxidation

Mahmoud, Hala R.

, p. 954 - 963 (2016)

Novel mesoporous 0.25Cr2O3–0.75ZrO2nanomaterials were successfully synthesized via hydrothermal method in the presence of anionic, cationic and non-ionic surfactants, namely, SDS, CTAB and Triton X-100, respectively. The effect of different surfactants and their concentrations on the physicochemical properties and the catalytic activity of the catalysts were studied by the XRD, HR-TEM, FT-IR, BET, UV–vis/DR, NH3-TPD and ethanol oxidation techniques. XRD results indicated that all the as-prepared nanomaterials were amorphous materials. The morphology study demonstrated that the sample with CTAB has the smallest particle size while that with SDS has the largest value. The catalysts prepared with non-ionic and cationic surfactants have the highest surface area and the pore volume while those prepared with anionic or without surfactant have the smallest values. Additionally, the surface area of the catalysts decreases with increasing the surfactant content. The optical study indicated that the absorption peak of the nanomaterials shifts towards the short wavelength by changing the various surfactants. It is well-observed by NH3-TPD that the non-ionic and cationic surfactants enhanced the amount of acidic sites on the catalyst surface. These results indicate that the catalytic activity of mesoporous catalysts can be improved effectively by the addition of non-ionic and cationic surfactants.

Study of the Ethylation of Ethanol by Using a Dual-cell Fourier Transform Mass Spectrometer

Bjarnason, Asgeir

, p. 847 - 848 (1989)

-

Oniumsilica-immobilized-Keggin acids: Acidity and catalytic activity for ethyl tert-butyl ether synthesis and acetic acid esterification with ethanol

Kovalchuk,Kochkin,Sfihi,Zaitsev,Fraissard

, p. 247 - 257 (2009)

Keggin heteropolyacids were immobilized on functionalized silica as their onium (γ-propyl-N-pyridinium, γ-propyl-N-methyl and γ-propyl-N-butyl-imidazolium) salts. Interaction between HPA and the surface-grafted onium cations affords acid salts. In contrast to bare silica, impregnated with HPA, these materials have monoanionic dispersions of HPA on the surface and superior resistance to HPA leaching in polar media. The greatest stability of the Keggin structure and resistance to leaching were found for H4SiW12O40-(SiW)-, and the lowest for H3PMo12O40-(PMo)-based samples. In the two model reactions tested, the liquid-phase synthesis of ETBE and the esterification of AcOH with EtOH, these solids display good catalytic performance (activity per anion, up to 150 and 25 h-1, respectively) and relative high structural stability. Catalysts having a greater coverage of organic functions (revealed by comparing two pyridinium salts) and hydrophobic cations (by comparing two imidazolium salts) have the best performance. Amongst the heteropolyacids studied, H4SiW12O40 is the most active and promising for catalyst design.

Heterogeneous Parahydrogen-Induced Polarization of Diethyl Ether for Magnetic Resonance Imaging Applications

Salnikov, Oleg G.,Svyatova, Alexandra,Kovtunova, Larisa M.,Chukanov, Nikita V.,Bukhtiyarov, Valerii I.,Kovtunov, Kirill V.,Chekmenev, Eduard Y.,Koptyug, Igor V.

, p. 1316 - 1322 (2021)

Magnetic resonance imaging (MRI) with the use of hyperpolarized gases as contrast agents provides valuable information on lungs structure and function. While the technology of 129Xe hyperpolarization for clinical MRI research is well developed, it requires the expensive equipment for production and detection of hyperpolarized 129Xe. Herein we present the 1H hyperpolarization of diethyl ether vapor that can be imaged on any clinical MRI scanner. 1H nuclear spin polarization of up to 1.3 % was achieved using heterogeneous hydrogenation of ethyl vinyl ether with parahydrogen over Rh/TiO2 catalyst. Liquefaction of diethyl ether vapor proceeds with partial preservation of hyperpolarization and prolongs its lifetime by ≈10 times. The proof-of-principle 2D 1H MRI of hyperpolarized diethyl ether was demonstrated with 0.1×1.1 mm2 spatial and 120 ms temporal resolution. The long history of use of diethyl ether for anesthesia is expected to facilitate the clinical translation of the presented approach.

-

Hori,Oike,Hukusima

, (1940)

-

THE SURFACE STRUCTURE AND CATALYTIC PROPERTIES OF ONE-ATOMIC LAYER AMORPHOUS NIOBIUM-OXIDE ATTACHED ON SiO2

Asakura, Kiyotaka,Twasawa, Yasuhiro

, p. 859 - 862 (1986)

A SiO2-attached one-atomic layer amorphous niobium-oxide catalyst was prepared by the two-stage attaching reaction between silanol groups and Nb(OC2H5)5 followed by chemical treatments with H2O and O2.The one-atomiclayer Nb oxide catalyst was found to be active and selective for ethene formation from ethanol.

Evans,Sutton

, p. 794 (1913)

-

Skaerblom

, (1928)

-

-

Bansal,Freeman

, p. 4173 (1970)

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Solvent effects in liquid-phase dehydration reaction of ethanol to diethylether catalysed by sulfonic-acid catalyst

Vanoye, Laurent,Zanota, Marie-Line,Desgranges, Audrey,Favre-Reguillon, Alain,De Bellefon, Claude

, p. 276 - 280 (2011)

The liquid-phase dehydration of ethanol to diethylether over heterogeneous sulfonic-acid catalysts was carried out in a stirred batch reactor. The different Amberlyst catalysts were found to have similar activities for this reaction; even though Amberlyst 70 showed a lower acid capacity compensated by a higher specific activity. By comparing the conversion of ethanol as a function of reaction mixture composition, it was found that reaction rates greatly depended on ethanol concentration but also on reaction mixture polarity. The swelling of the used resins could not explain the observed variations of initial reaction rate since this effect was observed both with resins and with homogeneous catalyst, i.e. p-toluenesulfonic acid. The initial ethanol concentration has a complex effect on initial reaction rates that could not be correlated by usual kinetic models. Taking account of the intrinsic reactivity trends of the SN2 etherification reaction, a strong dependence was found between solvent properties and initial reaction rate.

Dabrowski et al.

, p. 297,309, 311 (1970)

Conversion of ethanol and glycerol to olefins over the Re- and W-containing catalysts

Zharova,Chistyakov,Zavelev,Kriventsov,Yakimchuk,Kryzhovets,Petrakova,Drobot,Tsodikov

, p. 337 - 345 (2015)

The catalytic conversion of a mixture of ethanol and glycerol over the Re - W/Al2O3 catalysts was studied. The Re - W binary system exhibits a non-additive cocatalytic effect in the conversion of ethanol and its mixture with glycerol into the fraction of olefins C4 - C9. The non-additive increase in the catalytic activity is associated with the specific structure of the binuclear metallocomplex precursors, due to which the supported metals are arranged in the immediate vicinity from each other on the support surface and intensively interact to form Re7+. The study of the combined conversion of ethanol and glycerol made it possible to find an optimum ratio of the reactants in the initial mixture. The yield of target hydrocarbons attains 50 wt.% based on the amount of carbon passed through the reactor.

Kremann

, p. 211,245, 275, 671 (1910)

Catalytic activity of heteropoly tungstate catalysts for ethanol dehydration reaction: Deactivation and regeneration

Verdes, Orsina,Sasca, Viorel,Popa, Alexandru,Suba, Mariana,Borcanescu, Silvana

, p. 123 - 132 (2021)

The pure and palladium doped 12-tungstophosphoric acid - H3PW12O40 (HPW) and its cesium salts CsxH3-xPW12O40 (x = 1, 2, 2.25 and 2.5) were prepared and characterized by thermal analysis, FTIR, XRD, BET and XPS methods. In this paper were determined the optimal reaction temperature and the effect of palladium on the coke content during the dehydration of ethanol in the temperature range of 200?350 °C. Above 300 °C, a strong deactivation of the catalysts was caused by coke formation. The catalytic tests demonstrate that by supporting the HPW and PdyPW (y = 0.15, 0.2 and 0.25) on mesoporous molecular sieve SBA-15 the catalytic activity in ethanol dehydration reaction was improved. Palladium doping of HPW/SBA-15 significantly decreases the formation of coke deposit. The formation of coke during the ethanol dehydration does not affect the Keggin structure which led us to conclude that such catalysts can be regenerated in air and regain their catalytic activity for a short time.

One-pot synthesis of inorganic-organic hollow microsphere solid-acid catalysts in a W/O microemulsion system

Okada, Tomohiko,Mishima, Shozi,Yoshihara, Shingo

, p. 32 - 33 (2009)

Acid-supporting hollow microspheres were successfully prepared through a novel synthetic procedure on the introduction of a catalytic active species in the void space; one-pot synthesis was achieved by addition of 12-tungstophosphoric acid to the aqueous phase in a water-in-oil emulsion and simultaneous formation of a polyorganosiloxane shell (precursors are in oil phase) through sol-gel reactions. The resulting solid was porous and was active as solid-acid catalyst as shown by vapor-phase dehydration of ethanol. Copyright

An Unusually Acidic and Thermally Stable Cesium Titanate CsxTi2- yMyO4 (x = 0.67 or 0.70; M = vacancy or Zn)

Maluangnont, Tosapol,Wuttitham, Boonyawat,Hongklai, Panisa,Khunmee, Pongsatorn,Tippayasukho, Sorawat,Chanlek, Narong,Sooknoi, Tawan

, p. 6885 - 6892 (2019)

Proton-free, alkali-containing layered metal oxides are thermally stable compared to their protonic counterparts, potentially allowing catalysis by Lewis acid sites at elevated temperatures. However, the Lewis acidic nature of these materials has not been well explored, as alkali ions are generally considered to promote basic but to suppress acidic character. Here, we report a rare example of an unusually acidic cesium-containing oxide CsxTi2-yMyO4 (x = 0.67 or 0.70; M = Ti vacancy or Zn). These lepidocrocite-type microcrystals desorbed NH3 at >400 °C with a total acidity of 410 μmol g-1 at a specific surface area of only 5 m2 g-1, without the need for lengthy proton-ion exchange, pillaring, delamination, or restacking. The soft and easily polarized Cs+ ion essentially drives the formation of the Lewis acidic site on the surfaces as suggested by IR of sorbed pyridine. The two-dimensional layered structure was preserved after the oxide was employed in the ethanol conversion at 380 °C, the temperature at which the protonic form could have converted to anatase. The structure was also retained after the NH3 temperature-programmed desorption measurement up to 700 °C. The production of ethylene from ethanol, well-known to occur over acid sites, unambiguously confirmed the acidic nature of this cesium titanate.

Greenwood, N. N.,McGinnety, J. A.,Owen, J. D.

, (1972)

Gilman et al.

, p. 1034,1038,1039 (1954)

Preparation and Catalytic Properties of New SiO2-attached Nb-dimer Catalyst: Regulation of Acidity-Basicity by the number of Metal Atoms in Surface Active Sites

Ichikuni, Nobuyuki,Asakura, Kiyotaka,Iwasawa, Yasuhiro

, p. 112 - 113 (1991)

New Nb dimers on an SiO2 surface, prepared from the reaction between 5-C6H5)H-μ-(η5,η1-C5H4)>2 and surface OH groups, are found to have an oxygen-bridged dimeric structure, as characterised by extended X-ray fine structure (EXAFS), which is active and selective for the dehydratation of ethanol in contrast to the dehydrogenation ability of the Nb monomer catalyst.

A study of commercial transition aluminas and of their catalytic activity in the dehydration of ethanol

Phung, Thanh Khoa,Lagazzo, Alberto,Rivero Crespo, Miguel Angel,Sanchez Escribano, Vicente,Busca, Guido

, p. 102 - 113 (2014)

Conversion of ethanol was investigated over four commercial aluminas prepared by different industrial procedures and one commercial silica-alumina. Characterization was performed by TEM, XRD, SBET and porosity measurements, and IR spectroscopy of the surface OH groups and of adsorbed CO and pyridine. Different features are attributed to different phases (γ-, δ-, θ-Al2O3) and different impurities (Na +, Cl-). Total conversion of ethanol with >99% selectivity to ethylene is achieved at 623 K over the purer Al2O 3 catalyst (Na 3+ sites in a tetrahedral environment located on edges and corners of the nanocrystals. Ethanol adsorbs dissociatively on Lewis acid-base pair sites but may also displace water and/or hydroxyl groups from Lewis acidic Al3+ sites forming the active intermediate ethoxy species. Surface ethoxy groups are supposed to be intermediate species for both diethyl ether and ethylene production. Silica-alumina also works as a Lewis acid catalyst. The slightly lower activity on surface area basis of silica-alumina than aluminas attributed to the lower density of Lewis acid sites and the absence of significant basicity.

Effect of Au nanoparticles on the activity of TiO2 for ethanol upgrading reactions

Quesada,Arreola-Sánchez,Faba,Díaz,Rentería-Tapia,Ordó?ez

, p. 23 - 33 (2018)

This article analyses the role of gold nanoparticles supported on TiO2 for the gas-phase ethanol condensation. Previously, the original P25 surface was modified for increasing the Au-Ti interaction, in order to minimize the thermal deactivation. Catalysts were tested both in absence and presence of hydrogen (523–673 K, WHSV = 7.9 h?1; yEtOH= 0.32; yH2= 0-0.1; 0.1 MPa). Parent TiO2 is mainly selective for dehydration reactions yielding diethyl ether (favoured at low temperatures) and ethylene (favoured at higher temperatures). The presence of Au in the catalyst promotes dehydrogenation pathways, yielding acetaldehyde, as well as condensation products (mainly butanol, with selectivities close to 10%). According to DRIFT spectroscopy results, the strong ethanol adsorption on the TiO2 surface justifies the low yields and the high relevance of side-reactions produced by inter- or intra- molecular dehydration routes (diethyl ether, and ethylene formation). The gold addition minimizes this adsorption and enhances the main route by a double role: an improvement in the dehydrogenation rate (yielding more acetaldehyde) and an enhancement in the hydrogenation steps.

Catalytic activity of LiZr2(PO4)3 nasicon-type phosphates in ethanol conversion process in conventional and membrane reactors

Ilin, Andrey B.,Orekhova, Natalia V.,Ermilova, Margarita M.,Yaroslavtsev, Andrey B.

, p. 29 - 36 (2016)

In this paper synthesis and catalytic properties of new catalysts based on double lithium-zirconium phosphate (LiZr2(PO4)3) with monoclinic NASICON-type structure, doped by indium, niobium and molybdenum are discussed. The obtained samples with particle size of 50-300 nm were characterized by X-ray diffraction, scanning electron microscopy and X-ray microanalysis. The synthesized samples exhibit catalytic activity in the dehydration and dehydrogenation reactions of ethanol conversion. The main products were acetaldehyde, diethyl ether, hydrogen, C2- and C4-hydrocarbons. Indium- and molibdenum-doped samples were characterized by high activity in dehydrogenation processes, while niobium-doped was more active in dehydration processes. The highest selectivity in diethyl ether formation was achieved for LiZr2(PO4)3 and Nb-doped samples (90 and 60% at 300°C). The highest hydrogen yield (up to 60%) was obtained with the use of In-doped catalyst. LiZr2(PO4)3 and Mo-doped samples are also noticeable for high C4-hydrocarbons formation, selectivity to which reaches 60% at 390°C. Use of a 100% hydrogen selective palladium-ruthenium alloy membrane increases hydrogen yield by 20%.

Product Control in Conversion of Ethanol on MIL-101(Cr) with Adjustable Br?nsted Acid Density

Ming, Zheng,Wang, Yingli,Zhang, Tiexin,Li, Lingyun,Duan, Chunying,Liu, Zhongmin

, p. 6234 - 6240 (2020)

MIL-101(Cr) with adjustable Br?nsted acid density was prepared via post-synthetic sulfation strategy, which was carried out with sulfuric acid in the presence of trifluoromethanesulfonic anhydride, using nitromethane as solvent. XRD, TG, EDS, XPS, IR, NH3-TPD and acid-base titration were used to characterize structure and acidity. Adopting conversion of ethanol as a probe reaction, gas-solid catalytic characteristics on MIL-101(Cr) and post-synthetic sulfated MIL-101(Cr) in a micro fixed-bed reactor were studied by continuous feeding. Combined with the regulation of reaction parameters, selective production of ethylene (100 %) or diethyl ether (99 %) could be achieved.

Novel synthesis of homogenous CsxWO3 nanorods with excellent NIR shielding properties by a water controlled-release solvothermal process

Guo, Chongshen,Yin, Shu,Zhang, Peilin,Yan, Mei,Adachi, Kenji,Chonan, Takeshi,Sato, Tsugio

, p. 8227 - 8229 (2010)

Nanosize homogenous rod-like tungsten bronze CsxWO3 with excellent NIR shielding ability was successfully synthesized by a novel and facile water controlled-release solvothermal process (WCRSP).

Chemical surface functionalization of bulk poly (p-phenylene sulfide) yields a stable sulfonic acid catalyst

Zwettler, Niklas,Engb?k, Jakob S.,Lundsgaard, Rasmus,Paranowska, Irena,Nielsen, Tina E.,Clyens, Stuart,Christiansen, Jens,Andersen, Morten ?.

, p. 47 - 54 (2015)

Catalytic materials are important in industrial chemistry; these materials must be inexpensive and easy to process as well as resistant to chemicals, heat and structural loads. Poly (p-phenylene sulfide) (PPS) is a widely used and exceptionally resistant thermoplast. We demonstrate that the superficial regions of polymerized bulk PPS can be sulfonated using either SO3 or acetyl sulfate, yielding a solid core of unaltered PPS with a sulfonic acid-functionalized surface. The SO3 method was the most efficient and achieved 0.9 mmol H+ per gram of polymer. We show that the sulfonated surfaces function as durable solid acid catalysts for the dehydration of ethanol to diethyl ether. We also develop a simple method for the formation of porous PPS structures based on compression molding and porogen leaching. Based on these results, we suggest that surface functionalization of bulk PPS can be used to develop a novel class of moldable, easily produced and durable heterogeneous catalysts.

Calingaert,Soroos,Hnizda

, p. 392 (1942)

Dehydration of ethanol over copper and cerium phosphotungstates supported on MCM-41

Trakarnpruk, Wimonrat

, p. 168 - 170 (2013)

The selective dehydration of 80% ethanol to diethyl ether on copper and cerium phosphotungstates supported on MCM-41 was carried out; the latter showed higher activity.

Rigid Arrangements of Ionic Charge in Zeolite Frameworks Conferred by Specific Aluminum Distributions Preferentially Stabilize Alkanol Dehydration Transition States

Bates, Jason S.,Di Iorio, John R.,Gounder, Rajamani,Hibbitts, David,Hoffman, Alexander J.,Nimlos, Claire T.,Nystrom, Steven V.

, p. 18686 - 18694 (2020)

Zeolite reactivity depends on the solvating environments of their micropores and the proximity of their Br?nsted acid sites. Turnover rates (per H+) for methanol and ethanol dehydration increase with the fraction of H+ sites sharing six-membered rings of chabazite (CHA) zeolites. Density functional theory (DFT) shows that activation barriers vary widely with the number and arrangement of Al (1–5 per 36 T-site unit cell), but cannot be described solely by Al–Al distance or density. Certain Al distributions yield rigid arrangements of anionic charge that stabilize cationic intermediates and transition states via H-bonding to decrease barriers. This is a key feature of acid catalysis in zeolite solvents, which lack the isotropy of liquid solvents. The sensitivity of polar transition states to specific arrangements of charge in their solvating environments and the ability to position such charges in zeolite lattices with increasing precision herald rich catalytic diversity among zeolites of varying Al arrangement.

Janczak

, (1930)

A new method for quantifying iodine in a starch-iodine matrix

Manion, Bruce A.,Holbein, Bruce E.,Marcone, Massimo F.,Seetharaman, Koushik

, p. 2698 - 2704 (2010)

A rapid and sensitive method for quantifying iodine in intact starch granules using gas chromatography is described with detection limits as low as 0.2% (w/w) iodine in starch. Sample preparation includes NaBH4 reduction of the various iodine species associated with starch to the colorless soluble iodide ion, followed by its quantitative derivatization to EtI using Et3O+BF4- in CH2Cl2. Identification and quantification of EtI is carried out by extraction and injection of the EtI so generated in CH2Cl2 into a gas chromatography-mass spectrometer (GC-MS). Routine quantification of EtI was then performed using GC with a flame ionization detector (GC-FID). Results for different iodine:potassium iodide ratios of the initially bound iodine and for seven different starch matrices showed that in all cases regression coefficients for the standards were high (R2 >0.96).

Ethanol dehydration on silica-aluminas: Active sites and ethylene/diethyl ether selectivities

Phung, Thanh Khoa,Busca, Guido

, p. 110 - 115 (2015)

Commercial silica-alumina catalysts prepared by different procedures have been characterized. Both present strong Lewis acidity together with Br?nsted sites able to protonate pyridine. No evidence of "zeolitic" bridging OH's but significant heterogeneity of terminal silanol groups, part of which are likely "pseudobridging", was found. Similar high activity in ethanol conversion but markedly different selectivities to ethylene and diethyl ether were found. They are less active than both zeolites and γ-Al2O3. Lewis sites with alumina-like acidobasic neighbor are more selective for ethylene production while Lewis sites with silica-like covalent neighbor are more selective for diethyl ether.

Alvorado

, p. 790 (1928)

-

Hayashi

, (1957)

-

EFFECT OF THE NATURE OF THE CARRIER AND REDUCTION CONDITIONS ON THE PROPERTIES OF RHENIUM CATALYSTS OF HYDROGENATION OF ETHYL ACETATE

Avaev, V. I.,Ryashentseva, M. A.,Minachev, Kh. M.

, p. 15 - 19 (1988)

-

-

Alexander,Horn,Munro

, (1938)

-

Direct conversion of ethanol into ethylene oxide on gold-based catalysts: Effect of CeOx and Li2O addition on the selectivity

Lippits,Nieuwenhuys

, p. 142 - 149 (2010)

Results are presented concerning the behavior of alumina-supported gold catalysts and the effects of addition of Li2O and CeOx on the oxidation, dehydrogenation and dehydration reactions of ethanol. Pure alumina mainly acts as an acidic catalyst and produces diethyl ether and ethylene. Gold particles play an important role in converting ethanol into ethylene oxide and acetaldehyde. Addition of Li2O influences the selectivity by suppressing the formation of diethyl ether and ethylene. With the Au/Li2O/Al2O3 catalysts, a high selectivity toward ethylene oxide can be obtained. The influence of the oxygen concentration on the gas flow is investigated. It is suggested that at low concentrations, the role of oxygen is mainly to prevent coke formation on the catalytic surface.

-

Boswell,Dilworth

, p. 1494 (1925)

-

Ethanol dehydration and dehydrogenation on γ-Al2O3: Mechanism of acetaldehyde formation

DeWilde, Joseph F.,Czopinski, Christopher J.,Bhan, Aditya

, p. 4425 - 4433 (2014)

Steady state kinetics and measured pyridine inhibition of ethanol dehydration and dehydrogenation rates on γ-alumina above 623 K show that ethanol dehydrogenation can be described with an indirect hydrogen transfer mechanism to form acetaldehyde and ethane and that this mechanism proceeds through a shared surface intermediate with ethylene synthesis from ethanol dehydration. Ethane is produced at a rate within experimental error of acetaldehyde production, demonstrating that ethane is a coproduct of acetaldehyde synthesis from ethanol dehydrogenation. Steady state kinetic measurements indicate that acetaldehyde synthesis rates above 623 K are independent of co-fed water partial pressure up to 1.7 kPa and possess an ethanol partial pressure dependence between 0 and 1 (Pethanol = 1.0-16.2 kPa), consistent with ethanol dehydrogenation rates being inhibited only by ethanol monomer surface species. The surface density of catalytically active sites for ethylene and diethyl ether production were estimated from in situ pyridine titration experiments to be ~0.2 and ~1.8 sites nm-2, respectively, at 623 K. Primary kinetic isotope effects for ethylene and acetaldehyde are measured only when the C-H bonds of ethanol are deuterated, verifying that C-H bond cleavage is kinetically limiting for both products. The proposed indirect hydrogen transfer model for acetaldehyde synthesis is consistent with experimentally observed reaction rate dependences and kinetic isotope effects and highlights the complementary role of hydrogen adatom removal pathways in the formation of aldehydes on Lewis acidic systems. (Chemical Equation Presented).

HYDROGENATION OF ETHYL ACETATE OH Re/γ-Al2O3 CATALYST

Minachev, Kh. M.,Avaeav, V. I.,Ryashentseva, M. A.

, p. 280 - 283 (1986)

-

A comparative study of direct versus post-synthesis alumination of mesoporous FSM-16 silica

Zimowska,Michalik-Zym,Kry?ciak-Czerwenka,Dula,Socha,Pamin,Bazarnik,Bahranowski,Olejniczak,Lityńska-Dobrzyńska,Serwicka

, p. 623 - 631 (2016)

Al-FSM-16 mesoporous silicas were synthesized either by direct method, from Al-kanemite (Al-FSM-16/D), or by post-synthesis impregnation of purely siliceous FSM-16 with Al(NO3)3 (Al-FSM-16/P) and characterized with XRD, XRF, SEM, TEM, nitrogen sorption isotherms, 27Al and 29Si MAS NMR, FTIR, XPS, NH3-TPD, FTIR of pyridine adsorption and catalytic decomposition of ethanol. Only substitutional Al sites exist in Al-FSM-16/D, while in Al-FSM-16/P some Al remains in extra-lattice positions. Upon transformation of Al-FSM-16/D into hydrogen form a certain amount of extra-framework Al is formed. Direct alumination introduces a higher degree of structural disorder. In Al-FSM-16/D, Al is preferentially accumulated at inner pore walls, while in Al-FSM-16/P external surface is Al-rich. Post-synthesis alumination is more efficient in introducing acid sites into FSM-16. The generated acidity is of Br?nsted and Lewis nature, the latter being stronger than the former.

Morphology-dependent phase transformation of γ-Al2O3

Lee, Jaekyoung,Jeon, Himchan,Oh, Dong Gun,Szanyi, Janos,Kwak, Ja Hun

, p. 58 - 68 (2015)

The phase transformations of platelet- and rod-shaped γ-Al2O3 were investigated and compared to that of a commercial sample by XRD, BET surface area measurements, transmission electron microscopy (TEM), solid state 27Al-NMR, and ethanol temperature programmed desorption (TPD) after sequential annealing in air up to 1100 °C. After annealing at 1100 °C, commercial γ-Al2O3 mostly transformed into α-Al2O3 with drastic surface area reduction (from 200 m2/g to 25 m2/g). Interestingly, platelet- and rod-shaped γ-Al2O3 which showed exactly the same XRD patterns transformed into different phases upon the high temperature calcinations. Platelet-shaped γ-Al2O3 transformed into θ-phase while the rod-shaped γ-Al2O3 transformed into the δ-phase and not to the α-polymorph. Both platelet- and rod-shaped aluminas retained significantly higher surface area (~60 m2/g) than the commercial one after the same treatment at 1100 °C. These results suggest that the phase transformation in γ-Al2O3 is strongly affected by not only the crystal structure of the starting material, but its morphology as well. Ethanol TPD from platelet- and rod-shaped alumina after 1100 °C annealing, showed significantly different desorption profiles which suggest different surface characteristics even though they had almost the same surface areas. These different phase transformations were also supported by solid state 27Al-NMR. After 1100 °C annealing commercial alumina showed the presence of mostly octahedral Al3+ ions, but the other two samples displayed even higher number of tetrahedral Al3+ ions than the initial γ-Al2O3. Morphological changes were also confirmed by TEM. All these results consistently suggest the morphology-dependent phase transformations of γ-Al2O3 and the improved thermal stability of platelet- and rod-shaped γ-Al2O3 in comparison to a commercial γ-Al2O3.

-

Clark,Graham,Winter

, p. 2753 (1925)

-

Efficient dehydration of ethanol on the self-organized surface layer of H3PW12O40 formed in the acidic potassium tungstophosphates

Matachowski,Drelinkiewicz,Lalik,Ruggiero-Miko?ajczyk,Mucha,Kry?ciak-Czerwenka

, p. 290 - 299 (2014)

The aim of present work was to evaluate a role of the secondary structures of the K2HPW12O40 and K2.5H 0.5PW12O40 salts in their catalytic activity for vapour-phase dehydration of ethanol. Particular attention was directed to the role of H3PW12O40 (HPW) existing as a self-organized surface layer, which covers partially or entirely the K 3PW12O40 core. The results showed that both salts are much more active than bulk HPW. It turned out that the dehydrated protons present in the studied salts transform ethanol to ethylene much easier than the hydrated protons existing in the HPW. The ammonia sorption measurements demonstrated that the [N2H7]+ adducts were formed easier on the surface of the K2HPW12O40 salt whereas the formation of the NH4+ cations dominated in the bulk HPW. The structures of potassium tungstophosphates after catalytic reaction were investigated by the FT-IR, XRD and N2-sorption methods. A self-organized surface layer of HPW in the K2HPW12O 40 salt was unstable because it transformed to the crystalline HPW, due to the reaction temperature as well as to the presence of ethanol or water (dehydration product). However, the structure of the K2HPW 12O40 salt can be partially restored after ageing for a month at ambient temperature in air with the relative humidity of 25%. In contrast, the secondary structure of the K2.5H0.5PW 12O40 salt remained practically unchanged after catalytic reaction. It makes this salt a very promising catalyst for the ethanol dehydration, with the conversion of 99.4% and the selectivity to ethylene attaining ca. 100% at 448 K.

Method for quantifying redox site densities in metal oxide catalysts: Application to the comparison of turnover frequencies for ethanol oxidative dehydrogenation over alumina-supported VOx, MoOx, and WOx catalysts

Nair, Hari,Baertsch, Chelsey D.

, p. 1 - 4 (2008)

Isothermal anaerobic titration with ethanol as a probe molecule is proposed as an accurate technique to quantify active redox site densities in supported metal oxide catalysts. It is shown that the number of active redox sites for VOx-Al2O3, MoOx-Al2O3, and WOx-Al2O3 catalysts is a function of both the metal atom and its oxide surface density, but the intrinsic redox rate per active site is independent of both of these factors. Thus, the difference in steady-state redox rates per metal atom is due only to differences in the number of redox sites under reaction conditions.

Valentin

, p. 498 (1950)

Nanocrystalline h-rth zeolite: An efficient catalyst for the low-temperature dehydration of ethanol to ethene

Lee, Jeong Hwan,Lee, Sujin,Hong, Suk Bong

, p. 2035 - 2039 (2018)

The low-temperature dehydration of bioethanol is an environmentally benign route to ethene production. Here we compare the catalytic properties of a series of cage-based small-pore zeolites with different framework structures, acid strengths, and/or crystallite sizes for ethanol dehydration at 200 8C under wet conditions (H2 O/EtOH = 0.2). Among the zeolites studied here, nanocrystalline H-RTH was found to be considerably more effective than H-mordenite, the best catalyst for this reaction known to date, which can be rationalized by product shape selectivity. Whereas the acidity of this zeolite also plays a crucial role in selectively forming ethene, its nanocrystallinity is primarily responsible for the observed high catalyst durability.

Dehydration of methanol and ethanol over silica-supported heteropoly acids in the gas phase: Surface-type versus bulk-type catalysis mechanism

Al-Faze, Rawan,Finch, Amy,Kozhevnikov, Ivan V.,Kozhevnikova, Elena F.

, (2020)

Dehydration of MeOH to dimethyl ether and EtOH to diethyl ether and ethene was studied at the gas-solid interface in the presence of bulk and SiO2-supported Keggin heteropoly acids (HPAs) H3PW12O40 (PW) and H4SiW12O40 (SiW) as catalysts. The catalysts were prepared by HPA impregnation from water and MeOH. Their acid strength, texture and structural integrity was characterised using NH3 adsorption calorimetry, BET, XRD and DRIFT spectroscopy. The strength of acid sites in HPA/SiO2 catalysts increased monotonously with HPA loading. In the dehydration of MeOH and EtOH, the turnover reaction rate for PW catalysts was higher than for SiW catalysts in agreement with their acid strength. HPA catalysts prepared from water and MeOH had a very close acid strength and showed similar activities in alcohol dehydration. The steady-state catalyst activity was found to correlate with the density of catalyst proton surface sites rather than with the HPA loading. This indicates that alcohol dehydration occurred via a mechanism of surface-type HPA catalysis at the gas-solid interface rather than a bulk-type (pseudo-homogeneous) catalysis.

Sulfated zirconia foams synthesized by integrative route combining surfactants, air bubbles and sol-gel transition applied to heterogeneous catalysis

Alves-Rosa, Marinalva A.,Martins, Leandro,Hammer, Peter,Pulcinelli, Sandra H.,Santilli, Celso V.

, p. 6686 - 6694 (2016)

Sulfated zirconia ceramic foams were produced by the sol-gel process using air-liquid foam and surfactants as dual pore templates. The results showed the presence of high porosity (until 93%) and surface area (105 m2 g-1), and a hierarchical structure of pore sizes in the range of macro (between 10 and 76 μm), and meso-scales (?6 nm). The hierarchical porous structure and pore wall texturization of ceramic foams produced by this process, besides the presence of strong acid sites, certify these materials as heterogeneous catalysts for dehydration reactions.

Nature of Zirconium Phosphite as an Acidic Catalyst

Wan, Ben-Zu,Cheng, Soofin,Anthony, Rayford G.,Clearfield, Abraham

, p. 1419 - 1424 (1991)

The nature of acidic sites on layered zirconium phosphite has been characterized by IR spectra, thermal analysis and catalytic dehydration of ethanol.The catalytic behaviour was compared with that of α-zirconium phosphate.The reaction sequences for ether and ethen formation were studied by analysing the kinetic data.The Broensted acidity of monohydrogen orthophosphate groups was considered to be the common active site on α-zirconium phosphate and the zirconium phosphite sample calcined at 673 K.For the latter compound, the phosphite groups on the exterior surface were found to be oxidised to phosphate by calcination in air.The uncalcined sample of zirconium phosphite exhibited a different catalytic behaviour.Its selectivity for diethyl ether was the highest among the catalysts studied.The dehydration activity of this compound was presumed to be due to the polar P-H bonds in the phosphite groups.

Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy

Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael

supporting information, p. 1481 - 1487 (2022/03/07)

We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.

Selective Preparation of Olefins through Conversion of C2 and C3 Alcohols on NASICON-Type Phosphates

Ermilova, M. M.,Il’in, A. B.,Orekhova, N. V.,Yaroslavtsev, A. B.

, p. 693 - 700 (2021/07/26)

Abstract—: We have studied the catalytic activity of LiZr2(PO4)3-based NASICON-type phosphates for conversion of C2 and C3 aliphatic alcohols with the aim of selectively preparing C2–C4 olefins. Selectivity has been controlled via partial heterovalent substitutions of In3+ or Nb5+ for Zr4+ or Mo for phosphorus. We have investigated the structure and morphology of the synthesized catalysts. The nature of the dopants has been shown to play a key role in determining the selectivity of the catalysts studied. Partial In3+ substitution for Zr4+ improves the dehydrogenating properties of the materials, whereas partial substitutions of Nb5+ for Zr4+ and Mo6+ for P5+ improve their dehydrating properties. We have demonstrated the possibility of highly selective preparation of ethylene and butylenes from ethanol and of propylene from propanol-1 and propanol-2.

Selective Butene Formation in Direct Ethanol-to-C3+-Olefin Valorization over Zn-Y/Beta and Single-Atom Alloy Composite Catalysts Using in Situ-Generated Hydrogen

Allard, Lawrence F.,Assary, Rajeev S.,Cordon, Michael J.,Krause, Theodore R.,Kropf, A. Jeremy,Li, Zhenglong,Lin, Fan,Liu, Dongxia,Miller, Jeffrey T.,Purdy, Stephen C.,Unocic, Kinga A.,Wang, Huamin,Wegener, Evan C.,Yang, Ce,Zhang, Junyan,Zhou, Mingxia

, p. 7193 - 7209 (2021/06/30)

The selective production of C3+olefins from renewable feedstocks, especially via C1and C2platform chemicals, is a critical challenge for obtaining economically viable low-carbon middle-distillate transportation fuels (i.e., jet and diesel). Here, we report a multifunctional catalyst system composed of Zn-Y/Beta and “single-atom” alloy (SAA) Pt-Cu/Al2O3, which selectively catalyzes ethanol-to-olefin (C3+, ETO) valorization in the absence of cofed hydrogen, forming butenes as the primary olefin products. Beta zeolites containing predominately isolated Zn and Y metal sites catalyze ethanol upgrading steps (588 K, 3.1 kPa ethanol, ambient pressure) regardless of cofed hydrogen partial pressure (0-98.3 kPa H2), forming butadiene as the primary product (60% selectivity at an 87% conversion). The Zn-Y/Beta catalyst possesses site-isolated Zn and Y Lewis acid sites (at ~7 wt % Y) and Br?nsted acidic Y sites, the latter of which have been previously uncharacterized. A secondary bed of SAA Pt-Cu/Al2O3selectively hydrogenates butadiene to butene isomers at a consistent reaction temperature using hydrogen generatedin situfrom ethanol to butadiene (ETB) conversion. This unique hydrogenation reactivity at near-stoichiometric hydrogen and butadiene partial pressures is not observed over monometallic Pt or Cu catalysts, highlighting these operating conditions as a critical SAA catalyst application area for conjugated diene selective hydrogenation at high reaction temperatures (>573 K) and low H2/diene ratios (e.g., 1:1). Single-bed steady-state selective hydrogenation rates, associated apparent hydrogen and butadiene reaction orders, and density functional theory (DFT) calculations of the Horiuti-Polanyi reaction mechanisms indicate that the unique butadiene selective hydrogenation reactivity over SAA Pt-Cu/Al2O3reflects lower hydrogen scission barriers relative to monometallic Cu surfaces and limited butene binding energies relative to monometallic Pt surfaces. DFT calculations further indicate the preferential desorption of butene isomers over SAA Pt-Cu(111) and Cu(111) surfaces, while Pt(111) surfaces favor subsequent butene hydrogenation reactions to form butane over butene desorption events. Under operating conditions without hydrogen cofeeding, this combination of Zn-Y/Beta and SAA Pt-Cu catalysts can selectively form butenes (65% butenes, 78% C3+selectivity at 94% conversion) and avoid butane formation using onlyin situ-generated hydrogen, avoiding costly hydrogen cofeeding requirements that hinder many renewable energy processes.

CATALYTIC CONVERSION OF ETHANOL TO 1-/2-BUTENES

-

Paragraph 0013-0022; 0026-0046, (2021/06/11)

Simple and economical conversion of aqueous ethanol feed streams into butenes by a single step method using transition metal oxides on a silica supports under preselected processing conditions. By directly producing a C4-rich olefin mixture from an ethanol containing stream various advantages are presented including, but not limited to, significant cost reduction in capital expenses and operational expenses.

Process route upstream and downstream products

Process route

ethanol
64-17-5

ethanol

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

diethyl ether

1-ethoxypentane
17952-11-3

1-ethoxypentane

Conditions
Conditions Yield
With sulfuric acid; Npr2: Diamylen; Npr3: Aethylamylketone; Npr4: Methylhexylketon;
ethanol
64-17-5

ethanol

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene
15148-19-3

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene

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

diethyl ether

diethyl sulphite
623-81-4

diethyl sulphite

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With copper dichloride; for 24h; Product distribution; Ambient temperature; other reagent;
91%
70%
93.6 % Chromat.
1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene
15148-19-3

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene

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

diethyl ether

diethyl sulphide
70-29-1

diethyl sulphide

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

Conditions
Conditions Yield
With ethanol; copper dichloride; at 22 ℃; Rate constant; pseudo-first-order rate constants for ethanolysis reactions;
ethanol
64-17-5

ethanol

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

diethyl ether

hydrogen iodide
10034-85-2

hydrogen iodide

ethyl iodide
75-03-6

ethyl iodide

Conditions
Conditions Yield
at 80 ℃; im Rohr;
diethyl ether
60-29-7,927820-24-4

diethyl ether

ethane
74-84-0

ethane

ethene
74-85-1

ethene

carbon monoxide
201230-82-2

carbon monoxide

hydrogen
1333-74-0

hydrogen

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

acetaldehyde

Conditions
Conditions Yield
With La0.8Sr0.2Fe0.8Cr0.2O3; water; at 700 ℃; for 240h; Reagent/catalyst; Inert atmosphere; Flow reactor;
2-phenoxy-1-phenylethanone
721-04-0

2-phenoxy-1-phenylethanone

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

diethyl ether

1-ethoxy-1-phenylethane
3299-05-6

1-ethoxy-1-phenylethane

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

ethylbenzene

2-phenoxy-1-phenylethanol
4249-72-3

2-phenoxy-1-phenylethanol

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With nitrogen; water; In ethanol; at 280 ℃; for 4h; Autoclave;
ethanol
64-17-5

ethanol

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

diethyl ether

hydrogen
1333-74-0

hydrogen

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

acetaldehyde

Conditions
Conditions Yield
With 2.5O4P(3-)*0.5Li(1+)*2Zr(4+)*0.5MoO4(2-); In neat (no solvent); at 420 ℃; Temperature; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Flow reactor;
ethanol
64-17-5

ethanol

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

diethyl ether

octanol
111-87-5

octanol

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

(E/Z)-2-buten-1-ol
6117-91-5,542-72-3

(E/Z)-2-buten-1-ol

ethene
74-85-1

ethene

2-ethyl-1-butanol
97-95-0

2-ethyl-1-butanol

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

acetaldehyde

butan-1-ol
71-36-3

butan-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
Conditions Yield
With strontium deficient apatite 50 molpercent; at 300 - 400 ℃; for 4h; Flow reactor;
ethanol
64-17-5

ethanol

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

diethyl ether

octanol
111-87-5

octanol

Ethyl hexanoate
123-66-0

Ethyl hexanoate

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

(E/Z)-2-buten-1-ol
6117-91-5,542-72-3

(E/Z)-2-buten-1-ol

ethene
74-85-1

ethene

2-ethyl-1-butanol
97-95-0

2-ethyl-1-butanol

butyl ethyl ether
628-81-9

butyl ethyl ether

ethyl n-hexyl ether
5756-43-4

ethyl n-hexyl ether

acetic acid butyl ester
123-86-4

acetic acid butyl ester

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

carbon dioxide

carbon monoxide
201230-82-2

carbon monoxide

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

acetaldehyde

ethyl acetate
141-78-6

ethyl acetate

hexanal
66-25-1

hexanal

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

butanone
78-93-3

butanone

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

iso-butanol

butan-1-ol
71-36-3

butan-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
Conditions Yield
at 295 ℃; Autoclave; Supercritical conditions;
ethanol
64-17-5

ethanol

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

diethyl ether

octanol
111-87-5

octanol

Ethyl hexanoate
123-66-0

Ethyl hexanoate

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

(E/Z)-2-buten-1-ol
6117-91-5,542-72-3

(E/Z)-2-buten-1-ol

ethene
74-85-1

ethene

2-ethyl-1-butanol
97-95-0

2-ethyl-1-butanol

butyl ethyl ether
628-81-9

butyl ethyl ether

acetic acid butyl ester
123-86-4

acetic acid butyl ester

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

carbon dioxide

carbon monoxide
201230-82-2

carbon monoxide

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

acetaldehyde

ethyl acetate
141-78-6

ethyl acetate

hexanal
66-25-1

hexanal

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

butanone
78-93-3

butanone

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

iso-butanol

butan-1-ol
71-36-3

butan-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
Conditions Yield
at 275 ℃; for 5h; under 76005.1 Torr; Pressure; Time; Catalytic behavior; Autoclave; Supercritical conditions;

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