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Cas Database

104-76-7

104-76-7

Identification

  • Product Name:2-Ethylhexanol

  • CAS Number: 104-76-7

  • EINECS:203-234-3

  • Molecular Weight:130.23

  • Molecular Formula: C8H18O

  • HS Code:29339990

  • Mol File:104-76-7.mol

Synonyms:2-Ethyl-1-hexanol;2-Ethyl-1-hexyl alcohol;2-Ethylhexylalcohol;Conol 10WS;Ethylhexanol;G 301;NSC 9300;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn; IrritantXi

  • Hazard Codes:Xn,Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory 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 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 . Anesthesia, nausea, headache, dizziness; mildly irritating to skin and eyes. (USCG, 1999) /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. This chemical is combustible. 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. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. 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. Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.

  • 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. Separated from strong oxidants and strong bases. Store in an area without drain or sewer access. Ventilation along the floor.Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

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

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  • Manufacture/Brand:Usbiological
  • Product Description:2-Ethyl-1-hexanol
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  • Product Description:2-Ethyl-1-hexanol >99.5%(GC)
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  • Product Description:2-Ethyl-1-hexanol for synthesis. CAS 104-76-7, chemical formula CH CH CH CH CH(C H )CH OH., for synthesis
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Relevant articles and documentsAll total 113 Articles be found

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Haeusermann

, p. 1211,1214 (1951)

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Preparation and catalytic performance of NiO-MnO2/Nb2O5-TiO2 for one-step synthesis of 2-ethylhexanol from n-butyraldehyde

An, Hualiang,Li, Sibo,Wang, Yanji,Zhang, Jiaxun,Zhao, Xinqiang

, (2021)

One-pot synthesis of 2-ethylhexanol(2EHO) from n-butyraldehyde is of commercialimportance. The promotion of 2EHO selectivity requires suppressing direct hydrogenation of n-butyraldehyde. In this work, a series of NiO-MOx/Nb2O5-TiO2 catalysts were prepared and utilized by means of reduction-in-reaction technique, aiming at delaying the formation of metal sites and suppressing the direct hydrogenation. NiO-MnO2/Nb2O5-TiO2 with a Ni/Mn mass ratio of 10 and NiO-MnO2 loading of 14.3 wt% shows the best catalytic performance; 2-EHO selectivity could reach 90.0% at a complete conversion of n-butyraldehyde. Furthermore the catalyst could be used for four times without a substantial change in its catalytic performance.

Non-Oxidative Dehydrogenation Pathways for the Conversion of C2-C4 Alcohols to Carbonyl Compounds

Shylesh, Sankaranarayanapillai,Kim, Daeyoup,Ho, Christopher R.,Johnson, Gregory R.,Wu, Jason,Bell, Alexis T.

, p. 3959 - 3962 (2015)

Gold nanoparticles (NPs) supported on hydrotalcite (Au/HT) are highly active and selective catalysts for the continuous, gas-phase, non-oxidative dehydrogenation of bioderived C2-C4 alcohols. A sharp increase in turn over frequency (TOF) is noted when the size of Au NPs is less than 5 'nm relating to the strong synergy between metallic Au NPs and the acid-base groups on the support surface. It is shown that catalytic activity depends critically on Au NP size, support composition, and support pretreatments. A reaction pathway elucidated from kinetic isotope effects suggests that the abstraction of β-H by Au NPs (C-H activation) is the rate-determining step in the dehydrogenation of bioderived C2-C4 alcohols. All that′s good is gold: Gold nanoparticles supported on calcined hydrotalcite (Au/HT) are highly active and very selective catalysts for the continuous, gas-phase, non-oxidative dehydrogenation of bioderived C2-C4 alcohols.

Reaction of ethanol over hydroxyapatite affected by Ca/P ratio of catalyst

Tsuchida, Takashi,Kubo, Jun,Yoshioka, Tetsuya,Sakuma, Shuji,Takeguchi, Tatsuya,Ueda, Wataru

, p. 183 - 189 (2008)

The mineral hydroxyapatite [HAP; Ca10(PO4)6(OH)2] is the chief component of animal bones and teeth. It also is known to function as a catalyst with both acid and base sites, depending on the manner in which it is synthesized. We closely studied the reaction of ethanol over HAP using catalysts of different Ca/P molar ratios. These were prepared by controlling the pH of the solution during precipitation synthesis. We found that the distribution of acid sites and basic sites on the catalyst surface varied with the Ca/P ratio of HAP. The yields of ethylene, 1-butanol, and 1,3-butadiene were correlated with the ratio of acid sites and basic sites. We further found that yields of higher alcohols, such as 1-butanol, that are known as Guerbet alcohols and are characteristic products of ethanol over HAP, are functions of the probability of ethanol activation (α) on the catalyst surface.

Catalytic Upgrading of Ethanol to n-Butanol via Manganese-Mediated Guerbet Reaction

Kulkarni, Naveen V.,Brennessel, William W.,Jones, William D.

, p. 997 - 1002 (2018)

Replacement of precious metal catalysts in the Guerbet upgrade of ethanol to n-butanol with first-row metal complex catalysts is highly appreciated due to their economic and environmental friendliness. The manganese pincer complexes of the type [(RPNP)MnBr(CO)2] (R = iPr, Cy, tBu, Ph or Ad) are found to be excellent catalysts for upgrading ethanol to n-butanol. Under suitable reaction conditions and with an appropriate base, about 34% yield of n-butanol can be obtained in high selectivity. A detailed account on the effect of the temperature, solvent, nature, and proportion of base used and the stereoelectronic effects of the ligand substituents on the catalytic activity of the catalysts as well as the plausible deactivation pathways is presented.

Transformations of butyraldehyde in the presence of catalysts based on large-pore molecular sieves VPI-5 and AlPO4-8

Isakov, Ya. I.,Minachev, Kh. M.,Tome, R.,Tissler, A.,Oehlmann, G.,et al.

, p. 2004 - 2010 (1994)

It was found that zeolite-like ctystalline aluminophosphates VPI-5, Si-VPI-5, and Mn-VPI-5 as well as those derived from them, AlPO4-8, SAPO4-8, and MnAPO4-8, are capable of catalyzing aldol condensation and crotonization of butyraldehyde (BA).Pd/AlPO4-8 is catalytically active in hydrocondensation of BA with H2 at atmospheric pressure.The activities in BA conversion to 2-ethylhexane-3-ol-1-al increase in following order: Mn-VPI-5 +NaX (CsNaX), but they are much more stable.Pd/AlPO4-8 catalyzes BA conversion to 2-ethylhexanal even in the absence of H2 feed to the reaction zone.The influence of catalyst pretreatments and experimental conditions on the catalyst structures and catalytic activities is discussed. - Key words: butyraldehyde; condendation; crystalline aluminophosphates; molecular sieves; VPI-5; AlPO4-8; catalysis.

A STUDY OF POLYFUNCTIONAL ZEOLITE CATALYSTS. COMMUNICATION 7. CATALYTIC PROPERTIES OF METAL-M1+NaX ZEOLITE SYSTEMS IN THE HYDROCONDENSATION OF BUTYRALDEHYDE

Minachev, Kh. M.,Isakov, Ya. I.,Isakova, T. A.,Usachev, N. Ya.

, p. 274 - 279 (1986)

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SODIUM SULFIDE AS A SELECTIVE REDUCING REAGENT FOR ALDEHYDES TO ALCOHOLS. USE OF ALUMINA AS AN EFFECTIVE CATALYST

Kamitori, Yasuhiro,Hojo, Masaru,Masuda, Ryoichi,Yamamoto, Masaki

, p. 253 - 254 (1985)

Intrinsic reactivity of sodium sulfide is well controlled by impregnating it on alumina, so that aldehydes can be readily reduced to the corresponding alcohols, while ketones, esters and even nitro compounds are all inert toward this reagent.

Direct self-condensation of bio-alcohols in the aqueous phase

Xu, Guoqiang,Lammens, Tijs,Liu, Qiang,Wang, Xicheng,Dong, Linlin,Caiazzo, Aldo,Ashraf, Nadim,Guan, Jing,Mu, Xindong

, p. 3971 - 3977 (2014)

Bio-alcohols (e.g. ethanol, butanol) are primarily obtained as diluted aqueous solutions from biomass fermentation, and thus the subsequent isolation is a very costly process. So the direct transformation of bio-alcohols in water will have great advantages. This study describes the development of catalysts used for the self-condensation of bio-alcohols in water (that mimic the primary fermentation solutions). Efficient iridium catalysts have been developed rationally from homogeneous to heterogeneous, and the immobilized catalysts could be reused without any loss of activity, which is very important for the development of practical processes. The expected self-condensation could be realized with 80-90% selectivity in water and air. Such a protocol might be used for producing butanol from ethanol solution directly, which is an improved higher-alcohol biofuel. Other useful chemicals, such as 2-ethylhexanol, could also be obtained from renewable resources through this condensation reaction. This journal is the Partner Organisations 2014.

Conversion of ethanol into linear primary alcohols on gold, nickel, and gold–nickel catalysts

Chistyakov,Zharova,Tsodikov,Nikolaev,Krotova,Ezzhelenko

, p. 803 - 811 (2016)

The direct conversion of ethanol into the linear primary alcohols CnH2n+1OH (n = 4, 6, and 8) in the presence of the original mono- and bimetallic catalysts Au/Al2O3, Ni/Al2O3, and Au–Ni/Al2O3 was studied. It was established that the rate and selectivity of the reaction performed under the conditions of a supercritical state of ethanol sharply increased in the presence of Au–Ni/Al2O3. The yield of target products on the bimetallic catalyst was higher by a factor of 2–3 than that reached on the monometallic analogs. Differences in the catalytic behaviors of the Au, Ni, and Au–Ni systems were discussed with consideration for their structure peculiarities and reaction mechanisms.

Antimicrobial and Antioxidant Potential of Berberisinol, a New Flavone from Berberis baluchistanica

Pervez, Samreen,Saeed, Muhammad,Ali, Muhammad Shaiq,Fatima, Itrat,Khan, Haroon,Ullah, Irfan

, p. 247 - 251 (2019)

A new flavone, berberisinol (1), has been isolated from the EtOAc fraction of the MeOH extract of Berberis baluchistanica, along with known compounds, palmatine (2), berberine (3), 8-oxoberberine (4), β-sitosterol (5), oleanolic acid (6), and gallic acid (7), isolated for the first time from this species. Spectroscopic techniques including two-dimensional NMR were used for structural elucidation. Berberisinol (1) showed significant antibacterial and antioxidant potential.

Cascade engineered synthesis of 2-ethyl-1-hexanol from n-butanal and 2-methyl-1-pentanol from n-propanal using combustion synthesized Cu/Mg/Al mixed metal oxide trifunctional catalyst

Patankar, Saurabh C.,Yadav, Ganapati D.

, p. 223 - 233 (2017)

2-Ethyl-1-hexanol (2-EH) is a commercially important chemical that requires cost effective catalytic processes for synthesis. The cascade engineered synthesis of 2-EH was done in a single pot from n-butanal using solventless conditions with trifunctional mixed metal oxide containing 5% Cu and Mg/Al ratio of 3. This trifunctional catalyst was made by combustion synthesis technique which resulted in a porous network with narrow pore size distribution. The catalyst was characterized before and after reuse by FTIR, XRD, SEM, TEM, CO2-TPD, NH3-TPD, TPR, TGA and nitrogen BET analysis. The kinetics of reaction and selectivity profile of 2-EH are reported. The work was extended to one pot cascade engineered synthesis of 2-methyl-1-pentanol (2-MP) from n-propanal using the same catalyst. There was a significant effect of molecular size on rate of reaction and selectivity of the product. This is the first ever report on the one pot synthesis of 2-MP from n-propanal.

Decomposition of trichlorobenzene with different radicals generated by alternating current electrolysis in aqueous solution

Nakamura, Akinobu,Hirano, Keiji,Iji, Masatoshi

, p. 802 - 803 (2005)

Trichlorobenzenes can be easily decomposed by alternating current electrolysis in aqueous solution. The mechanism of the decomposition was found to be based on selective redox reactions with different radicals - hydrogen atoms and hydroxyl radicals - generated by water electrolysis. Copyright

Hydrogenation of 2-Ethylhexenal Using Supported-Metal Catalysts for Production of 2-Ethylhexanol

Liu, Guoxiu,Liu, Shiwei,Liu, Siyuan,Yu, Shitao,Li, Lu,Liu, Fusheng,Xie, Congxia,Song, Xiuyan

, p. 987 - 995 (2017)

Abstract: The catalytic hydrogenation of 2-ethylhexenal was investigated over Pd supported on ZrO2, CeO2, Al2O3, MCM-41, MAS-7 and SBA-15. The activities and the selectivities of the catalysts were strongly affected by the nature of the support. Pd/ZrO2 had an excellent catalytic performance for the hydrogenation. The superior dispersion of Pd on the support ZrO2, and the stable structure of active components on ZrO2 as well as the synergistic effect of the bifunctional metal-support interaction enhanced the catalytic performance of Pd/ZrO2. The conversion of 2-ethylhexenal and the selectivity for 2-ethylhexanol were 100 and 99.1% respectively when the reaction was carried out at 240 °C for 7?h. The product was easily separated from the catalyst and the catalyst was of good reusability when it was repeated six times. In addition, the aggregation of Pd nanoparticles and the coking of ZrO2 the catalysts were the main cause for the catalyst deactivation. Graphical Abstract: [Figure not available: see fulltext.]

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Dvornikoff,Farrar

, p. 540 (1957)

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Base catalyzed hydrolysis of aerosol OT in aqueous and aquo-dioxane media

Mukherjee,Moulik,Mukherjee

, p. 1063 - 1074 (1994)

The OH- ion catalyzed hydrolysis of AOT and sodium mono-methyl succinate m aqueous and aquo-dioxane media has been studied. The second-order rate constant for the former has been found to be nearly ten times slower than that of the latter. At AOT concentrations above CMC, the rate constants become insensitive to the concentration in the studied range of temperature, 25 °C-40 °C. The activation parameters for the kinetic process have been found to be reasonable, negative entropy of activation has supported a stable transition state complex. A good enthalpy-entropy compensation of the kinetic process has been found both for AOT and sodium monomethyl succinate in aqueous and aquo-dioxane media supporting similar nature of the transition state complexes in the hydrolytic reactions. The enthalpies of hydrolysis of AOT and the half ester of succinic acid in aqueous and aquo-dioxane media have been also reported.

Successive vapour phase Guerbet condensation of ethanol and 1-butanol over Mg-Al oxide catalysts in a flow reactor

Larina, Olga V.,Valihura, Karina V.,Kyriienko, Pavlo I.,Vlasenko, Nina V.,Balakin, Dmytro Yu.,Khalakhan, Ivan,?endak, Toma?,Soloviev, Sergiy O.,Orlyk, Svitlana M.

, (2019)

The successive vapour phase condensation of ethanol and 1-butanol (via Guerbet reaction) in a flow reactor under atmospheric pressure was studied over catalytic Mg-Al oxide compositions. Wherein the vapour phase condensation of 1-butanol to 2-ethyl-1-hexanol in flow has been investigated for the first time. The acid/base capacity ratio, which is determined by the Mg/Al ratio, is an important characteristic for the activity and selectivity of Mg-Al oxide catalysts in the abovementioned processes. The carbon chain length of the reacting alcohols, an arrangement of surface active sites and other steric factors also have an impact on Guerbet condensation in the vapour phase. High productivity of Mg-Al oxide system to the Guerbet alcohols: 1-butanol – 25 g/(Lcat·h), 2-ethyl-1-hexanol – 19 g/(Lcat·h), has been achieved. The results have shown a prospect of successive conversion realization: 1) ethanol → 1-butanol; 2) 1-butanol → 2-ethyl-1-hexanol for the production of 2-ethyl-1-hexanol from ethanol.

Electronic and steric factors for enhanced selective synthesis of 2-ethyl-1-hexanol in the Ir-complex-catalyzed Guerbet reaction of 1-butanol

Xu, Zhanwei,Yan, Peifang,Liang, Changhui,Jia, Songyan,Liu, Xiumei,Zhang, Z. Conrad

, p. 1586 - 1592 (2021)

1-Butanol is a potential bio-based fermentation product obtained from cellulosic biomass. As a value-added chemical, 2-ethyl-1-hexanol (2-EH) can be produced by Guerbet conversion from 1-butanol. This work reports the enhanced catalytic Guerbet reaction of 1-butanol to 2-EH by a series of Cp*Ir complexes (Cp*: 1,2,3,4,5-pentamethylcyclopenta-1,3-diene) coordinated to bipyridine-type ligands bearing an ortho-hydroxypyridine group with an electron-donating group and a Cl? anion. The catalytic activity of the Cp*Ir complex increased by increasing the electron density of the bipyridine ligand when functionalized with the para-NMe2 and ortho-hydroxypyridine groups. A record turnover number of 14047 was attained. A mechanistic study indicated that the steric effect of the ethyl group on the α-C of 2-ethylhexanal (2-EHA) and the conjugation effect of C=C–C=O in 2-ethylhex-2-enal (2-EEA) benefits the high selectivity of 2-EH from 1-butanol by inhibiting the cross-aldol reaction of 2-EHA and 2-EEA with butyraldehyde. Nuclear magnetic resonance study revealed the formation of a carbonyl group in the bipyridine-type ligand via the reaction of the Cp*Ir complex with KOH.

THE RUTHENIUM COMPLEX-CATALYZED REDUCTION OF KETONES BY FORMIC ACID

Watanabe, Yoshihisha,Ota, Tetsuo,Tsuji, Yasushi

, p. 1585 - 1586 (1980)

An equimolar mixture of a ketone and formic acid was heated without solvent at 125 degC for 3 h in the presence of catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II) to give the corresponding secondary alcohols in excellent yields.

Hollow Ni-Co-B amorphous alloy nanospheres: Facile fabrication via vesicle-assisted chemical reduction and their enhanced catalytic performances

Wei,Zhao,Peng,Zhang,Bian,Li,Li

, p. 19253 - 19259 (2014)

In this paper, we develop a simple vesicle-assisted chemical reduction approach for synthesizing hollow Ni-Co-B nanospheres. With various characterization techniques, the resulting Ni-Co-B nanospheres are identified as amorphous alloys with a hollow chamber. Coexistence of NiII and CoII species plays a significant role in fabricating hollow nanospheric structures, because only solid nanoparticles can be obtained in the presence of a mono-metallic precursor. During liquid-phase hydrogenation of 2-ethyl-2-hexenaldehyde, hollow Ni-Co-B catalyst displays significant bi-site catalysis from bimetals and delivers much greater activity as well as better selectivity than associated with the dense Ni-Co-B catalyst. Additionally, this catalyst is also easily handled in liquid-phase reactions due to its lower density and magnetic property. The material design concept presented in this work opens a new avenue for the development of hollow non-noble metallic nanospheres and will draw more attention in the foreseeable future.

Isakov et al.

, (1972)

Guerbet Reaction over Strontium-Substituted Hydroxyapatite Catalysts Prepared at Various (Ca+Sr)/P Ratios

Silvester, Lishil,Lamonier, Jean-Fran?ois,Lamonier, Carole,Capron, Micka?l,Vannier, Rose-No?lle,Mamede, Anne-Sophie,Dumeignil, Franck

, p. 2250 - 2261 (2017)

The Guerbet reaction of ethanol to heavier products was performed over a series of extensively characterized Sr-substituted hydroxyapatites (HAPs) with different (Ca+Sr)/P ratios, and thus different structural, textural, and acid–base properties. The acid–base properties were correlated with the reactivity of the solids and an optimal ratio between the amount of acid and basic sites was determined (ca. 4), whereas the ethanol conversion was mainly depending on the specific surface area of the solids. The stoichiometric 100 mol % Sr-substituted sample (SrAp-100) was especially efficient in higher alcohols production, which can be illustrated by a total alcohol selectivity (76.4 %) higher than that of all the other solids at a 13 % ethanol isoconversion.

Direct synthesis of 2-ethylhexanol via n-butanal aldol condensation-hydrogenation reaction integration over a Ni/Ce-Al2O3 bifunctional catalyst

Liang, Ning,Zhang, Xiaolong,An, Hualiang,Zhao, Xinqiang,Wang, Yanji

, p. 2959 - 2972 (2015)

Direct synthesis of 2-ethylhexanol from n-butanal via the reaction integration of n-butanal self-condensation with 2-ethyl-2-hexenal hydrogenation is of crucial interest for industrial production of 2-ethylhexanol. Furthermore, as an important and versatile chemical, n-butanol can be produced simultaneously by reaction integration. In the present work, several bifunctional catalysts based on γ-Al2O3 were prepared by the impregnation method and were characterized by means of H2-TPR, XRD, TEM and H2-TPD, and their catalytic performance for direct synthesis of 2-ethylhexanol from n-butanal was investigated. The results showed that Co/Al2O3 had a low activity for hydrogenation and Cu/Al2O3 had a high selectivity for the hydrogenation of the C=O group while a Ru/Al2O3 catalyst only favored the hydrogenation of n-butanal to n-butanol. Among them, the Ni/Al2O3 catalyst showed the best catalytic performance and the yield of 2-ethylhexanol was the highest (49.4%). Ce-modified Ni/Al2O3 enhanced the competitiveness of aldol condensation versus hydrogenation of n-butanal and improved the selectivity of 2-ethylhexanol; the yield of 2-ethylhexanol rose to 57.8%. Then the influence of preparation conditions on the catalytic performance of Ni/Ce-Al2O3 was investigated and the suitable preparation conditions were obtained as follows: Ni loading = 10%, calcined at 550 °C for 5 h, and reduced at 570 °C for 4 h. The effect of reaction conditions on the integration reaction catalyzed by Ni/Ce-Al2O3 was investigated and the suitable reaction conditions were obtained as follows: weight percentage of Ni/Ce-Al2O3 = 15%, reaction temperature = 170 °C, reaction pressure = 4.0 MPa and reaction time = 8 h. Under the above reaction conditions, the yield of 2-ethylhexanol attained 66.9% and that of n-butanol was 18.9%. In addition, the components existing in the integration reaction system were identified by GC-MS analysis, and the main by-products were n-butyl butyrate, 2-ethylhexyl butyrate, n-butyric acid, etc. Based on the analysis of the reaction system, a reaction network for the direct synthesis of 2-ethylhexanol from n-butanal was proposed. Finally, an evaluation of the reusability of Ni/Ce-Al2O3 showed that the recovered Ni/Ce-Al2O3 catalyst lost its catalytic activity for the hydrogenation of the C=O group. The main reason for deactivation was that Ni species were covered by the flaky boehmite γ-AlO(OH) formed from the hydration of γ-Al2O3 in the reaction process.

Efficient conversion of ethanol to 1-butanol and C5-C9 alcohols over calcium carbide

Wang, Dong,Liu, Zhenyu,Liu, Qingya

, p. 18941 - 18948 (2019)

Production of 1-butanol or alcohols with 4-9 carbon atoms (C4-C9 alcohols) from widely available bio-ethanol has attracted much interest in recent years in academia and industry of renewable chemicals and liquid fuels. This work discloses for the first time that calcium carbide (CaC2) has a superior catalytic activity in condensation of ethanol to C4-C9 alcohols at 275-300 °C. The 1-butanol yield reached up to 24.5% with ethanol conversion of 62.4% at the optimized conditions. The by-products are mainly alcohols with 5-9 carbons besides 2-butanol, and the total yield of all the alcohols reached up to 56.3%. The reaction route was investigated through controlled experiments and quantitative analysis of the products. Results indicated that two reaction routes, aldol-condensation and self-condensation, took place simultaneously. The aldol-condensation route involves coupling of ethanol with acetaldehyde (formed from ethanol dehydrogenation) to form 2-butenol, which is subsequently hydrogenated to 1-butanol. The alkynyl moiety in CaC2 plays an important role in the catalytic pathways of both routes and affords the good activity of CaC2. CaC2 is converted to acetylene [C2H2] and calcium hydroxide [Ca(OH)2] simultaneously by the H2O that was generated from the condensation of alcohols.

Metal-Organic Framework-Derived Guerbet Catalyst Effectively Differentiates between Ethanol and Butanol

Neumann, Constanze N.,Rozeveld, Steven J.,Yu, Mingzhe,Rieth, Adam J.,Dincǎ, Mircea

, p. 17477 - 17481 (2019)

RuNi nanoparticles supported on a metal-organic framework (RuNi?MOF) and formed in situ from a ruthenium complex enclosed inside a nickel-based MOF act as a highly active catalyst for the Guerbet reaction of ethanol to 1-butanol, providing turnover numbers up to 725 000 Ru-1. Negligible activity of the RuNi?MOF ethanol upgrading catalyst system toward chemically similar 1-butanol makes it possible to synthesize the competent Guerbet substrate 1-butanol with >99% selectivity.

-

Magnani,McElvain

, p. 813,819 (1938)

-

-

Miller,Bennett

, p. 33,34 (1961)

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Highly Efficient Process for Production of Biofuel from Ethanol Catalyzed by Ruthenium Pincer Complexes

Xie, Yinjun,Ben-David, Yehoshoa,Shimon, Linda J. W.,Milstein, David

, p. 9077 - 9080 (2016)

A highly efficient ruthenium pincer-catalyzed Guerbet-type process for the production of biofuel from ethanol has been developed. It produces the highest conversion of ethanol (73.4%, 0.02 mol% catalyst) for a Guerbet-type reaction, including significant amounts of C4 (35.8% yield), C6 (28.2% yield), and C8 (9.4% yield) alcohols. Catalyst loadings as low as 0.001 mol% can be used, leading to a record turnover number of 18 ?209. Mechanistic studies reveal the likely active ruthenium species and the main deactivation process.

Catalytic performance of Ni/Γ-Al2O3 for hydrogenation of 2-ethyl-2-hexenal

Zhao, Lili,Wang, Yi,An, Hualiang,Zhao, Xinqiang,Wang, Yanji

, p. 74 - 77 (2018)

The effect of reaction conditions on the catalytic performance of Ni/γ-Al2O3 was investigated and the result showed that Ni/γ-Al2O3 showed excellent catalytic activity. However, the catalytic performance of the recovered Ni/γ-Al2O3 catalyst declined dramatically. The fresh and the recovered catalysts were comparatively analyzed by means of XRD, XPS and FT-IR techniques. The result demonstrated that the main reason for the activity decline of the recovered Ni/γ-Al2O3 catalyst is that the surface Ni has been reoxidized to NiO. After calcination and reduction, the recovered Ni/γ-Al2O3 catalyst could be reused four times without a significant decrease in its catalytic performance.

Thermally induced structural transformations of linear coordination polymers based on aluminum tris(diorganophosphates)

D?bowski, Maciej,?okaj, Krzysztof,Ostrowski, Andrzej,Zachara, Janusz,Wiecińska, Paulina,Falkowski, Pawe?,Krztoń-Maziopa, Anna,Florjańczyk, Zbigniew

, p. 16480 - 16491 (2018)

The thermal transitions of inorganic-organic hybrid polymers composed of linear aluminum tris(diorganophosphate) chains with a general formula of catena-Al[O2P(OR)2]3 (where R = C1-C8 alkyl group or phenyl moiety) have been studied by means of DSC, powder XRD, TGA and TG-QMS, as well as optical spectroscopy. DSC and XRD reveal that most of them undergo reversible structural transformations in the solid state between ?100 and 200 °C caused by the changes in conformation of their organic substituents; however, a translational displacement of the rigid polymeric chains occurs only in the case of the derivative bearing long 2-ethylhexyl groups, which becomes liquid at about 140 °C. The thermal decomposition of the studied polymers begins between 200 and 265 °C depending on the type of organic substituent R decorating their aluminophospate core. TGA combined with mass spectrometry of the evolved gaseous products shows that the pyrolytic decomposition of Al[O2P(OR)2]3 proceeds either through β-elimination of olefin (for compounds with C2-C8 aliphatic ligands), or a homolytic cleavage of the P-OR bond (for methyl and phenyl derivatives); both processes are accompanied by condensation of the newly formed POH groups and liberation of water. Powder XRD, FTIR and SEM analyses of the solid residues indicate that thermolysis of Al[O2P(OR)2]3 accompanied by olefin elimination leads to the formation of condensed aluminum phosphates, mainly aluminum cyclohexaphosphate, exhibiting porous morphology. On the other hand, thermal degradation of methyl or phenyl derivatives results in amorphous aluminophosphate residues, and the latter contains conducting carbonaceous phases.

Covalent Adaptable Networks Using β-Amino Esters as Thermally Reversible Building Blocks

Du Prez, Filip E.,Guerre, Marc,Taplan, Christian

supporting information, p. 9140 - 9150 (2021/07/01)

In this study, β-amino esters, prepared by the aza-Michael addition of an amine to an acrylate moiety, are investigated as building blocks for the formation of dynamic covalent networks. While such amino esters are usually considered as thermally nondynamic adducts, the kinetic model studies presented here show that dynamic covalent exchange occurs via both dynamic aza-Michael reaction and catalyst-free transesterification. This knowledge is transferred to create β-amino ester-based covalent adaptable networks (CANs) with coexisting dissociative and associative covalent dynamic exchange reactions. The ease, robustness, and versatility of this chemistry are demonstrated by using a variety of readily available multifunctional acrylates and amines. The presented CANs are reprocessed via either a dynamic aza-Michael reaction or a catalyst-free transesterification in the presence of hydroxyl moieties. This results in reprocessable, densely cross-linked materials with a glass transition temperature (Tg) ranging from -60 to 90 °C. Moreover, even for the low Tg materials, a high creep resistance was demonstrated at elevated temperatures up to 80 °C. When additional β-hydroxyl group-containing building blocks are applied during the network design, an enhanced neighboring group participation effect allows reprocessing of materials up to 10 times at 150 °C within 30 min while maintaining their material properties.

READILY BIODEGRADABLE ALKOXYLATE MIXTURES

-

Paragraph 0040-0043, (2021/05/14)

A mixture of octanols, nonanols and decanols is useful for the preparation of alkoxylates, which alkoxylates may be used as surfactants, which surfactants have surprisingly good biodegradability.

Hydrogen borrowing catalysis using 1° and 2° alcohols: Investigation and scope leading to α and β branched products

Frost, James R.,Cheong, Choon Boon,Akhtar, Wasim M.,Caputo, Dimitri F.J.,Christensen, Kirsten E.,Stevenson, Neil G.,Donohoe, Timothy J.

supporting information, (2021/04/07)

The alkylation of a variety of ketones using 1° or 2° alcohols under hydrogen borrowing catalysis is described. Initial research focused on the α-alkylation of cyclopropyl ketones with higher 1° alcohols (i.e. larger than MeOH), leading to the formation of α-branched products. Our search for additional substrates with which to explore this chemistry led us to discover that di-ortho-substituted aryl ketones were also privileged scaffolds, with Ph? (C6Me5) ketones being the optimal choice. Further investigations revealed that this motif was crucial for alkylation with 2° alcohols forming β-branched products, which also provided an opportunity to study diastereoselective and intramolecular hydrogen borrowing processes.

Room temperature depolymerization of lignin using a protic and metal based ionic liquid system: an efficient method of catalytic conversion and value addition

Mehta, Mohit J.,Kulshrestha, Akshay,Sharma, Shweta,Kumar, Arvind

, p. 1240 - 1247 (2021/02/26)

Lignin is one of the most abundant biopolymer which can be utilized to synthesize various chemicalsviaits depolymerization. However, depolymerization of lignin generally occurs under very harsh conditions. Herein, we report the efficient depolymerization of ligninviadissolution in a mixed ionic liquid system: ethyl ammonium nitrate (EAN) + prolinium tetrachloromanganate(ii) [Pro]2[MnCl4] at 35 °C and under atmospheric pressure conditions. The high dissolution of lignin in ethyl ammonium nitrate provided a large number of H-bonding sites leading to the cracking of lignin and subsequent oxidative conversion by [Pro]2[MnCl4]viathe formation of metal-oxo bonding between Mn and lignin molecules. The extracted yield of vanillin was found to be 18-20% on lignin weight basisviaGC-MS analysis. The depolymerization of lignin was confirmed by SEM, FT-IR and PXRD analysis. Since lignin contains UV-absorbing functional groups, the regenerated biomass after the recovery of the depolymerized products was further utilized to synthesize a UV-shielding material. The constructed films from such a material exhibited a high SPF value of 22 and were found to be very effective by limiting the UV degradation of rhodamine B thus making the lignin valorization process economically viable and environmentally sustainable.

Process route upstream and downstream products

Process route

pentanal
110-62-3

pentanal

butyraldehyde
123-72-8

butyraldehyde

2-propylheptan-1-ol
10042-59-8

2-propylheptan-1-ol

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

2-propylhexanol
817-46-9

2-propylhexanol

2-ethylheptanol
817-60-7

2-ethylheptanol

Conditions
Conditions Yield
pentanal; butyraldehyde; With sodium hydroxide; In water; at 20 - 130 ℃; for 3.25h;
With hydrogen; In water;
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

1-Decanol
112-30-1

1-Decanol

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

acetaldehyde

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

butan-1-ol
71-36-3

butan-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
Conditions Yield
With deficient carbonate-containing hydroxyapatites (HapD); at 300 - 400 ℃; Reagent/catalyst; Temperature; Overall yield = 14 %; Catalytic behavior; Inert atmosphere;
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;
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;
alkaline lignin

alkaline lignin

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

1-(3-methoxy-4-hydroxyphenyl)ethanone
498-02-2

1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions
Conditions Yield
With 1-butyl-3-methyl imidazolium tetrachloromanganate(II); ethylammonium nitrate (EAN); at 35 ℃; for 6h;
10%
2-ethyl hexanol ester of hexadecanoic acid
29806-73-3

2-ethyl hexanol ester of hexadecanoic acid

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

Conditions
Conditions Yield
With water;
benzoic acid, butyl ester
136-60-7

benzoic acid, butyl ester

sodium butanolate
2372-45-4

sodium butanolate

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

Velate 368
5444-75-7

Velate 368

propiophenone
495-40-9

propiophenone

butan-1-ol
71-36-3

butan-1-ol

Conditions
Conditions Yield
at 180 ℃;
2-ethylhexenal
645-62-5

2-ethylhexenal

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

2‐ethylhex‐2‐en‐1‐ol
50639-00-4

2‐ethylhex‐2‐en‐1‐ol

Conditions
Conditions Yield
With Co59B41; hydrogen; In ethanol; at 99.84 ℃; for 5h; under 7500.75 Torr; Autoclave;
2-ethylhexenal
645-62-5

2-ethylhexenal

d,l-2-ethylhexanal
123-05-7

d,l-2-ethylhexanal

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

2‐ethylhex‐2‐en‐1‐ol
50639-00-4

2‐ethylhex‐2‐en‐1‐ol

Conditions
Conditions Yield
With butan-1-ol; at 180 ℃; for 4h; under 11103.3 Torr; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere;

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