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Cas Database

111-87-5

111-87-5

Identification

  • Product Name:1-Octanol

  • CAS Number: 111-87-5

  • EINECS:203-917-6

  • Molecular Weight:130.23

  • Molecular Formula: C8H18O

  • HS Code:2905161000

  • Mol File:111-87-5.mol

Synonyms:Caprylic alcohol;n-Octanol;n-Octyl alcohol;1-Hydroxyoctane;AI3-02169;Alcohol C-8;Alfol 8;C8 alcohol;CCRIS 9099;Caprylic alcohol;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes: Xi:Irritant;

  • Signal Word:Warning

  • Hazard Statement:H319 Causes serious eye irritationH412 Harmful to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. In case of skin contact Rinse and then wash skin with water and soap. In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Irritates skin and eyes. (USCG, 1999) 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. 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. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.; Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.; Methods and materials for containment and cleaning up Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids

  • 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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Relevant articles and documentsAll total 637 Articles be found

Nametkin,Tanewa

, (1943)

Oxidation of zinc organometallics prepared by hydrozincation or carbozincation using oxygen

Klement, Ingo,Luetjens, Henning,Knochel, Paul

, p. 3161 - 3164 (1995)

Organozinc compounds prepared by the hydrozincation or carbazincation of functionalized unsaturated molecules can be directly oxidized by oxygen affording alcohols after reductive workup in satisfactory yields.

Regioselective addition of stannylcyanocuprates to acetylenic ethers: A chemical and spectroscopic study

Cabezas,Oehlschlager

, p. 432 - 442 (1994)

The reactions of acetylenic ether 1 with higher order cuprates 2a, 2b and 2c were studied chemically and spectroscopically. Conditions were developed to efficiently and regioselectively prepare α- and β-stannylvinyl ethers. 1H and 13C NMR studies of these reactions suggest that in the presence of HMPA, higher order stannylcyanocuprate, (Bu3Sn)2Cu(CN)Li2, 2a, exists in equilibrium with Gilman cuprate, (Bu3Sn)2CuLi.

Electrophilic Etherification of α-Heteroaryl Carbanions with Monoperoxyacetals as a Route to Ketene O, O- And N, O-Acetals

Paris, Timothy J.,Schwartz, Chris,Willand-Charnley, Rachel

, p. 2369 - 2384 (2021)

Alkyl ketene acetals are useful reactants in a variety of synthetic processes, and yet, there are limited routes to their formation as isolable products. We now report the successful synthesis and isolation of heteroaryl ketene acetals through intermolecular transfer of alkoxyl (δ+OR) from electrophilic peroxides to lithiated benzofurans, indoles, and pyridines. Primary and secondary peroxyacetals enable selective transfer of the nonanomeric alkoxy group in moderate to high yield; substrates bearing an electron-donating substituent show enhanced reactivity toward electrophilic oxygen. Heteroaryl ketene acetals are remarkably stable throughout traditional purification techniques; the superior stability of ketene N,O-acetals compared to ketene O,O-acetals is presumably due to increased aromaticity of the indole and pyridine structures. The presented method overcomes typical problems associated with alkyl ketene acetal synthesis as reported products withstood workup and flash column chromatography procedures.

Highly selective and stable ZnO-supported bimetallic RuSn catalyst for the hydrogenation of octanoic acid to octanol

Hidajat, Marcel Jonathan,Hwang, Dong-Won,Yun, Gwang-Nam

, (2021)

The chemoselective hydrogenation of biomass-derived carboxylic acids is promising for the development of biorefineries. Herein, the selective conversion of octanoic acid to octanol over bimetallic RuSn/ZnO in a fixed-bed continuous reactor system, is reported. Almost complete conversion (99.4 %) of octanoic acid was achieved, with a remarkably high selectivity to octanol (93.0 %), when using specific reaction conditions (300°C, a weight hourly space velocity (WHSV) of 2 h?1, and 30 atm H2). Characterizations of the catalysts by BET, CO pulse chemisorption, ICP-AES, XRD, XPS and STEM-EDS revealed that the addition of Sn to Ru/ZnO resulted in the formation of a Ru3Sn7 alloy phase as well as SnOx. Comparison with Ru/ZnO catalyst gives an insight that the presence of Ru3Sn7 alloy was most likely the active site and it significantly improved the hydrogenation activity and selectivity to octanol. The SnOx and ZnO favored the formation of octyl octanoate by esterification of the formed octanol and octanoic acid, although it was successfully suppressed by optimizing the reaction conditions. Long-term stability tests revealed that RuSn/ZnO retained its activity for 1000 h with no coke formation. This study reveals the potential of RuSn/ZnO for the valorization of medium-chain fatty acids into value-added chemicals.

Identification of a marine NADPH-dependent aldehyde reductase for chemoselective reduction of aldehydes

Li, Guangyue,Ren, Jie,Wu, Qiaqing,Feng, Jinhui,Zhu, Dunming,Ma, Yanhe

, p. 17 - 22 (2013)

A putative aldehyde reductase gene from Oceanospirillum sp. MED92 was overexpressed in Escherichia coli. The recombinant protein (OsAR) was characterized as a monomeric NADPH-dependent aldehyde reductase. The kinetic parameters Km and kcat of OsAR were 0.89 ± 0.08 mM and 11.07 ± 0.99 s-1 for benzaldehyde, 0.04 ± 0.01 mM and 6.05 ± 1.56 s-1 for NADPH, respectively. This enzyme exhibited high activity toward a variety of aromatic and aliphatic aldehydes, but no activity toward ketones. As such, it catalyzed the chemoselective reduction of aldehydes in the presence of ketones, as demonstrated by the reduction of 4-acetylbenzaldehyde or the mixture of hexanal and 2-nonanone, showing the application potential of this marine enzyme in such selective reduction of synthetic importance.

A facile zirconium(IV) chloride catalysed selective deprotection of t-butyldimethylsilyl (TBDMS) ethers

Sharma,Srinivas,Radha Krishna, Palakodety

, p. 4689 - 4691 (2003)

A simple and efficient protocol for the selective deprotection of t-butyldimethylsilyl (TBDMS) ethers using 20 mol% ZrCl4 in 20-45 min and in high yields, is reported, wherein it is demonstrated that acid and base sensitive groups and allylic and benzylic groups are unaffected.

Engineering carboxylic acid reductase for selective synthesis of medium-chain fatty alcohols in yeast

Hu, Yating,Zhu, Zhiwei,Gradischnig, David,Winkler, Margit,Nielsen, Jens,Siewers, Verena

, p. 22974 - 22983 (2020)

Medium-chain fatty alcohols (MCFOHs, C6 to C12) are potential substitutes for fossil fuels, such as diesel and jet fuels, and have wide applications in various manufacturing processes. While today MCFOHs are mainly sourced from petrochemicals or plant oils, microbial biosynthesis represents a scalable, reliable, and sustainable alternative. Here, we aim to establish a Saccharomyces cerevisiae platform capable of selectively producing MCFOHs. This was enabled by tailoring the properties of a bacterial carboxylic acid reductase from Mycobacterium marinum (MmCAR). Extensive protein engineering, including directed evolution, structure-guided semirational design, and rational design, was implemented. MmCAR variants with enhanced activity were identified using a growth-coupled high-throughput screening assay relying on the detoxification of the enzyme’s substrate, medium-chain fatty acids (MCFAs). Detailed characterization demonstrated that both the specificity and catalytic activity of MmCAR was successfully improved and a yeast strain harboring the best MmCAR variant generated 2.8-fold more MCFOHs than the strain expressing the unmodified enzyme. Through deletion of the native MCFA exporter gene TPO1, MCFOH production was further improved, resulting in a titer of 252 mg/L for the final strain, which represents a significant improvement in MCFOH production in minimal medium by S. cerevisiae.

Intrinsic isotope effects suggest that the reaction coordinate symmetry for the cytochrome P-450 catalyzed hydroxylation of octane is isozyme independent

Jones,Rettie,Trager

, p. 1242 - 1246 (1990)

The mechanism of the ω-hydroxylation of octane by three catalytically distinct, purified forms of cytochrome P-450, namely, P-450(b), P-450(c), and P-450(LM2), was investigated by using deuterium isotope effects. The deuterium isotope effects associated with the ω-hydroxylation of octane-1,1,1-2H3, octane-1,8-2H2, and octane-1,1,8,8-2H4 by all three isozymes were determined. From these data the intrinsic isotope effects were calculated and separated into their primary and secondary components. The primary intrinsic isotope effect for the reaction ranged from 7.69 to 9.18 while the secondary intrinsic isotope effect ranged from 1.13 to 1.25. Neither the primary nor secondary isotope effect values were statistically different for any of the isozymes investigated. These data are consistent with a symmetrical transition state for a mechanism involving initial hydrogen atom abstraction followed by hydroxyl radical recombination which is essentially independent of the specific isozyme catalyzing the reaction. It is concluded that (1) in general the porphyrin-[FeO]3+ complex behaves as a source of a triplet-like oxygen atom, (2) the regioselectivity for the site of oxidation is dictated by the apoprotein of the specific isozyme of cytochrome P-450 catalyzing the reaction, and (3) the maximum primary intrinsic isotope effect for any cytochrome P-450 catalyzed oxidation of a carbon center is about 9, assuming no tunneling effects.

Dod-S-Me and methyl 6-morpholinohexyl sulfide (MMS) as new odorless borane carriers

Patra, Pranab K.,Nishide, Kiyoharu,Fuji, Kaoru,Node, Manabu

, p. 1003 - 1006 (2004)

Odorless Dod-S-Me (1) and MMS (3) are developed as efficient borane carriers. The yields of hydroborations and reductions with borane complex 2 of 1 are very high and the recovery of 1 after the reaction is quantitative. The borane complexes 4 and 5 of 3 are also useful. In the latter case chromatographic separation is unnecessary when excess oxidizing agent (alkaline H2O2) is used after hydroboration.

-

Gingras,Waters

, p. 3508,3511 (1954)

-

Cambie et al.

, p. 919 (1978)

2-pyridylsilyl group as a multifunctional 'phase tag' for solution phase synthesis

Yoshida, Jun-ichi,Itami, Kenichiro,Mitsudo, Koichi,Suga, Seiji

, p. 3403 - 3406 (1999)

2-Pyridyldimethylsilyl (2-PyMe2Si) group was found to serve as effective 'phase tag' for acid-base extraction for solution phase synthesis. Acid-base extraction of octyl(2-pyridyl)dimethylsilane gave rise to 98% recovery. The introduction of 2-PyMe2Si group to organic molecules was easily accomplished by Rh catalyzed hydrosilylation of alkenes with 2- PyMe2SiH. The removal of 2-PyMe2Si group was achieved by the oxidation with H2O2/KF (Tamao oxidation). In order to demonstrate the utility of 2- PyMe2Si group as a 'phase tag', a sequential multi-step transformation was conducted. The products of each steps were easily isolated by acid-base extraction, and were sufficiently pure for the direct use in the next step of the sequence.

Experimental study of chemical equilibria in the liquid-phase reaction between 1-octanol and ethanol to 1-ethoxyoctane

Guilera, Jordi,Ramirez, Eliana,Iborra, Montserrat,Tejero, Javier,Cunill, Fidel

, p. 2076 - 2082 (2013)

The equilibrium constants for the liquid-phase dehydration reaction between 1-octanol and ethanol to 1-ethoxyoctane (EOE) and water and the dehydration reaction between two ethanol molecules to ethoxyethane (DEE) and water were determined over Amberlyst 70 in the temperature range (410 to 463) K in a batch reactor. Both reactions were greatly shifted to products at the chemical equilibrium. In particular, product concentrations found for EOE synthesis were higher than those measured for DEE formation. Besides, both liquid-phase etherification reactions proved to be exothermic, with a reaction enthalpy change of (-18.9 ± 1.3) kJ·mol-1 for EOE synthesis and (-13.1 ± 0.9) kJ·mol-1 for DEE one, at 298 K. The EOE standard formation enthalpy value of (-436 ± 7) kJ·mol -1, in good agreement with the estimated value by a modified Benson method, and the EOE standard molar entropy value in the liquid phase of (434 ± 11) J·mol-1·K-1, slightly underestimated by the Benson method, are found.

Novel Cu and Cu2In/aluminosilicate type catalysts for the reduction of biomass-derived volatile fatty acids to alcohols

Harnos, Szabolcs,Onyestyak, Gyoergy,Barthos, Robert,Valyon, Jozsef,Stolcova, Magdalena,Kaszonyi, Alexander

, p. 1954 - 1962,9 (2012)

This work relates to the consecutive reduction of short chain carboxylic acids (volatile fatty acids, VFAs) to alcohols as main products. Acetic acid (AA) was used as a reactant to model the VFAs that can be produced by either thermochemical or biological biomass degradation. The amorphised zeolite supported copper catalysts (Cu/SiAl), especially the In-modified CuIn/SiAl catalysts, showed high hydroconversion activity and selectivity for alcohol, ester and aldehyde. Catalysts containing dispersed copper particles in amorphous aluminosilicate were obtained by dehydrating and H2-reducing Cu-forms of low-silica synthetic zeolites (A, X, P). The activity of the highly destructed Cu-aluminosilicates was found to depend on the structure of the zeolite precursor. The formation of ethyl acetate could be suppressed by adding water to the AA feed and by modifying the catalyst, e.g. by In2O 3 additive. In the catalysts modified by In2O3 additive formation of copper-indium alloy phase (Cu2In intermetallic compound) was detected resulting in a different selectivity than the one recorded for the Cu/SiAl.

REDUCTION OF ALDEHYDES AND KETONES WITH TETRAALKYLAMMONIUM BOROHYDRIDES

Raber, Douglas J.,Guida, Wayne C.,Shoenberger, Douglas C.

, p. 5107 - 5110 (1981)

Misinterpretations regarding the selectivity of tetraalkylammonium borohydride reductions in dichloromethane are resolved.Tetrabutylammonium borohydride offers several advantages, but both it and tetraethylammonium borohydride are highly useful synthetic reagents.

Modulation of photodeprotection by the sunscreen protocol

Eivgi, Or,Levin, Efrat,Lemcoff, N. Gabriel

, p. 740 - 743 (2015)

A protocol for the selective photoremoval of alcohol protecting groups modulated by the presence of auxiliary light absorbing molecules is presented. Thus, by this method, a single light source was used to selectively remove a specific protecting group in the presence of another chromophore with a lower molar absorption coefficient. The use of a molecular sunscreen, either internal or external, was found to be crucial to achieve high selectivities.

In Vivo Reduction of Medium- to Long-Chain Fatty Acids by Carboxylic Acid Reductase (CAR) Enzymes: Limitations and Solutions

Horvat, Melissa,Winkler, Margit

, p. 5076 - 5090 (2020)

Fatty aldehyde production by chemical synthesis causes an immense burden to the environment. Within this study, we explored a sustainable, aldehyde-selective and mild alternative approach by utilizing carboxylic acid reductases (CARs). CARs from Neurospora crassa (NcCAR), Thermothelomyces thermophila (TtCAR), Nocardia iowensis (NiCAR), Mycobacterium marinum (MmCAR) and Trametes versicolor (TvCAR) were overexpressed in E. coli K-12 MG1655 RARE (DE3) and screened for medium- to long-chain fatty acid (C6–C18) reduction. MmCAR showed the broadest tolerance towards all carbon-chain lengths and was selected for further investigations of fatty aldehyde synthesis in whole cells. To yield relevant product concentrations, different limitations of CAR whole-cell conversions were elucidated and compensated. We coupled an in vitro cofactor recycling system to a whole-cell biocatalyst to support cofactor supply and achieved 12.36 g L?1 of octanal (STY 0.458 g L?1 h?1) with less than 1.5 % of 1-octanol.

Smith

, p. 25,39 (1974)

Ternary (Cu, Ni and Co) Nanocatalysts for Hydrogenation of Octanal to Octanol: An Insight into the Cooperative Effect

Valand, Jignesh,Dasireddy, Venkata D. B. C.,Singh, Sooboo,Friedrich, Holger B.

, p. 525 - 538 (2017)

Abstract: Ternary metal oxides (Cu–Ni–Co) with different wt% loadings were supported on alumina by using an ultrasonic cavitation-impregnation method. A comparative silica catalyst was also prepared. Powder X-ray diffraction (XRD) showed the presence of the metal oxides on the surface of the supports and from in situ XRD results, the formation of metallic phases under a reducing atmosphere were observed. Temperature-programmed desorption (TPD) revealed the presence of Lewis and Br?nsted acidic sites in the catalysts. The metals supported on alumina showed a better dispersion compared to that on the silica support. All the catalysts were tested for the hydrogenation of octanal in a mixture of 10% octanal in octanol in a continuous flow fixed bed reactor by varying the pressure, temperature and hydrogen molar ratios. Under the hydrogenation conditions, the trimetallic catalysts (with Cu, Ni and Co) showed best catalytic performance for octanal hydrogenation when compared to bimetallic catalysts. The conversion of octanal and the selectivity towards octanol increased in proportion to an increase in the total metallic content and metal dispersion. The alumina based catalysts showed better activity compared to the silica catalyst due to higher metal dispersion. The silica supported catalyst showed a high selectivity towards C24 acetal due to its higher acidity and the product distribution over all the catalysts is in agreement with the distribution of acidic sites. Graphical Abstract: [Figure not available: see fulltext.]

Pentaco-ordinate Silicon Compounds in Synthesis: Chemo- and Stereo-selective Reduction of Carbonyl Compounds using Trialkoxy-substituted Silanes and Alkali Metal Alkoxides

Hosomi, Akira,Hayashida, Hisashi,Kohra, Shinya,Tominaga, Yoshinori

, p. 1411 - 1412 (1986)

Carbonyl compounds are reduced with trialkoxy-substituted silane to the corresponding alcohols chemo- and stereo-selectively in the presence of alkali metal alkoxide under mild conditions; reduction occurs very smoothly by using an alkoxide derived from pinacol as a bidentate ligand.

A Remarkable Inversion in the Selective Oxidation of Organoboranes and Thioethers

Brown, Herbert C.,Mandal, Arun K.

, p. 916 - 917 (1980)

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Bacterial CYP153A monooxygenases for the synthesis of omega-hydroxylated fatty acids

Honda Malca, Sumire,Scheps, Daniel,Kuehnel, Lisa,Venegas-Venegas, Elena,Seifert, Alexander,Nestl, Bettina M.,Hauer, Bernhard

, p. 5115 - 5117 (2012)

CYP153A from Marinobacter aquaeolei has been identified as a fatty acid ω-hydroxylase with a broad substrate range. Two hotspots predicted to influence substrate specificity and selectivity were exchanged. Mutant G307A is 2- to 20-fold more active towards fatty acids than the wild-type. Residue L354 is determinant for the enzyme ω-regioselectivity.

Quantitative Evaluation of the Effect of the Hydrophobicity of the Environment Surrounding Br?nsted Acid Sites on Their Catalytic Activity for the Hydrolysis of Organic Molecules

Miura, Hiroki,Kameyama, Shutaro,Komori, Daiki,Shishido, Tetsuya

, p. 1636 - 1645 (2019)

Sulfo-functionalized siloxane gels with a variety of surface hydrophobicities were fabricated to elucidate the effect of the environment surrounding the Br?nsted acid site on their catalytic activity for the hydrolysis of organic molecules. A detailed structural analysis of these siloxane gels by elemental analysis, X-ray photoelectron spectroscopy, Fourier-transformed infrared (FT-IR), and 29Si MAS NMR revealed the formation of gel catalysts with a highly condensed siloxane network, which enabled us to quantitatively evaluate the hydrophobicity of the environment surrounding the catalytically active sulfo-functionality. A sulfo group in a highly hydrophobic environment exhibited excellent catalytic turnover frequency for the hydrolysis of acetate esters with a long alkyl chain, whereas not only conventional solid acid catalysts but also liquid acids showed quite low catalytic activity. Detailed kinetic studies corroborated that the adsorption of oleophilic esters at the Br?nsted acid site was facilitated by the surrounding hydrophobic environment, thus significantly promoting hydrolysis under aqueous conditions. Furthermore, sulfo-functionalized siloxane gels with a highly hydrophobic surface showed excellent catalytic activity for the hydrolytic deprotection of silyl ethers.

Nickel catalyzed hydroboration with catecholborane

Kabalka,Narayana,Reddy

, p. 1019 - 1023 (1994)

Hydroborations of alkenes and alkyne with catecholborane were found to be catalyzed by activated nickel powder.

Indium, as an efficient co-catalyst of Cu/Al2O3 in the selective hydrogenation of biomass derived fatty acids to alcohols

Onyestyák, Gy?rgy,Harnos, Szabolcs,Kalló, Dénes

, p. 19 - 24 (2012)

Octanoic acid (OA) as model reactant of medium chain length, and its reduced products, octanal and octanol were hydroconverted over different components of a CuIn/Al2O3 composite catalyst. A fixed-bed flow through reactor was used at 21 bar total pressure in the temperature range of 240-360 °C. Fatty acid hydroconversion activity of alumina supported Cu catalyst and mainly the yield of selectively produced octanol can be greatly increased by In2O3 doping, suppressing the dehydration side reactions. Appearance of metallic indium on alumina supported reduced copper catalyst can arrest the consecutive catalytic reaction at the alcohol formation step prior to further dehydration to ether or alkenes. An industrial, conventionally used Adkins catalyst (72 wt.% CuCr2O4 and 28 wt.% CuO) and the novel bimetallic composite (CuIn/Al2O 3) were compared: both produce octanol with high selectivity, but the new chromium-free fatty acid hydrogenation catalyst is more active, nearly as active as earlier investigated NiIn/Al2O3.

Deprotection of Acetals and Silyl Ethers Using Some ?-Acceptors

Tanemura, Kiyoshi,Suzuki, Tsuneo,Horaguchi, Takaaki

, p. 290 - 292 (1994)

Hydrolysis of dodecanol dimethyl acetal and dodecyl silyl ethers in MeCN-H2O was examined using a catalytic silyl amount of ?-acceptors such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), tetracyanoethylene (TCNE), 7,7,8,8-tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (TCNQF4), and chloranil (CA).Cleavage of dodecyl triethylsilyl ether with TCNQ and CA was caused by room light.By application of DDQ-catalyzed deprotection of acetals to hydrolysis of tetrahydropyranyl ethers, the corresponding alcohols were obtained in quantitative yields.

A unique structural distribution pattern discovered for the cerebrosides from starfish Asterias amurensis

Yamaguchi, Ryosuke,Kanie, Yoshimi,Kanie, Osamu,Shimizu, Yoshitaka

, p. 115 - 122 (2019)

Cerebroside is an important family of the mono-glycosylated ceramides involved in the larger family of glycosphingolipid and sulfatide. Cerebroside is synthesized from ceramide by the transfer of glucose from UDP-glucose, and degraded back to ceramide, which plays an important role at the epidermis protecting interior of the body as a barrier. Because cerebroside is regarded as the source molecule of ceramide and is amphiphilic in nature, cerebroside is considered valuable as the ingredient of cosmetic lotion. Various sources can be considered as raw material of cerebrosides. Starfish is considered as one of such potent source. However, the structure of the ceramide part of cerebroside is not fully investigated. Therefore, the individual structures of cerebroside molecules need to be identified including sphingosine and fatty acyl group composition to assess the potential of the molecule. We investigated and determined the structures of cerebrosides in starfish Asterias amurensis using LC-MS, GC-MS, tandem mass spectrometry (MS/MS), and 1H NMR. We also discovered a characteristic structure distribution that was divided into three major groups: 1) a group composed of a relatively long sphingosine (C22) and a short length of fatty acyl group (less than C16), 2) a group composed of a typical C18 sphingosine and long fatty acyl groups (greater than C23), and 3) a group composed of C18 sphingosine and fatty acyl groups with their length less than C18. The calculated Log P values of cerebrosides ranging from 9 to 11 covered about 80% of the molecules that were in the range of those used in cosmetics, thus showing the potential usefulness of starfish Asterias amurensis as a source of raw material for cerebrosides.

Effects of Organic Modifiers on a Palladium Catalyst in the Competitive Hydrogenation of 1-Octene Versus Octanal: An Evaluation of Solid Catalysts with an Ionic Liquid Layer

Miller, Stuart F.,Friedrich, Holger B.,Holzapfel, Cedric W.,Dasireddy, Venkata D. B. C.

, p. 2628 - 2636 (2015)

The competitive hydrogenation between 1-octene and octanal has been investigated with a ≈5% palladium on alumina catalyst prepared in situ with the following organic modifiers: pyridine, 1-methylimidazole, 1,3-dimethylimidazole methylsulfate, 1,3-dimethylimidazole bis(trifluoromethylsulfonyl)imide and methyltri-sec-butylphosphonium methylsulfate. The results of these investigations indicate that the ionic liquid modifiers have significant and specific effects on catalytic performance, for example, certain systems can completely suppress octanal conversion. In addition, analytical techniques reveal that the matrix and quantity of organic species on the used catalysts are different if different ionic liquids are used as modifiers. Surface studies also reveal that the modifiers have a noticeable effect on the crystallite size and chemisorption properties of the catalysts.

Hydroboration. 59. Thexylchloroborane-Methyl Sulfide. A New Stable Monohydroborating Agent with Exceptional Regioselectivity

Brown, Herbert C.,Sikorski, James A.,Kulkarni, Surendra U.,Lee, Hsiupu D.

, p. 863 - 872 (1982)

Under selected conditions, the hydroboration of 2,3-dimethyl-2-butene with 1 equiv of BH2Cl*SMe2 proceeds cleanly in solution (CH2Cl2, ClCH2CH2Cl, Et2O) or under neat conditions to give exclusively the monohydroboration product, thexylchloroborane-methyl sulfide (ThxBHCl*SMe2).Stock solutions of ThxBHCl*SMe2 in CH2Cl2 or Et2O have unusual thermal stability at ambient temperatures or below.The hydroboration of reactive olefins, such as terminal or unhindered disubstituted alkenes, with ThxBHCl*SMe2 proceeds quantitatively with high regiospecificity in CH2Cl2,ClCH2CH2Cl, Et2O, and THF to produce isomerically pure thexylalkylchloroborane intermediates.Subsequent oxidation produces the desired alcohols in nearly quantitative yield with high regiospecificity.With less reactive olefins, such as 1-methylcyclopentene, cyclohexene, or α-pinene, 11B NMR showed that the desired thexylalkylchloroborane products were contaminated with alkyldichloroborane species, indicating that a significant amount of product redistribution had occured.This was reflected in a lower observed regioselectivity in the hydroboration of some less reactive alkenes with ThxBHCl*SMe2.

Highly active and selective platinum(0)-carbene complexes. Efficient, catalytic hydrosilylation of functionalised olefins

Marko, Istvan E.,Sterin, Sebastien,Buisine, Olivier,Berthon, Guillaume,Michaud, Guillaume,Tinant, Bernard,Declercq, Jean-Paul

, p. 1429 - 1434 (2004)

Readily available N-heterocyclic platinum-carbene complexes 1 are highly efficient catalysts for the regioselective hydrosilylation of alkenes. These novel organometallics tolerate a wide range of functional and protecting groups, can be stored for prolonged periods of time and are particularly active (TON > 106).

OXIDATIVE CLEAVAGE OF SILICON-CARBON BOND WITH TRIMETHYLAMINE-N-OXIDE. NEW ACCESS TO PRIMARY ALCOHOLS AND ALDEHYDES FROM TERMINAL ALKENES AND ALKYNES

Sakurai, Hideki,Ando, Masatomo,Kawada, Nobuo,Sato, Kazuhiko,Hosomi, Akira

, p. 75 - 76 (1986)

Oxidative cleavage of carbon-silicon bond of organosilanes with trimethylamine-N-oxide is achieved under mild conditions.The reaction occurs chemoselectively irrespective of the presence of amino and thio groups to give formally anti-Markovnikov hydration product of 1-alkenes and 1-alkynes via hydrosilylation.

Improving the catalytic behavior of Ni/Al2O3 by indium in reduction of carboxylic acid to alcohol

Onyestyák, Gy?rgy,Harnos, Szabolcs,Kalló, Dénes

, p. 184 - 188 (2011)

Octanoic acid (OA) was used as reactant with medium chain length to model the aliphatic carboxylic acids which can be produced by catalytic, thermochemical or biological degradation of biomass. A flow through reactor was applied at 21 bar total pressure (in general 20 bar hydrogen and 1 bar octanoic acid partial pressures) and 240-360°C. Fatty acid conversion activity of alumina supported Ni catalysts and the yield of selectively produced alcohol can be increased drastically by In2O3 doping. Appearance of metallic indium can effectively direct the step by step catalytic reduction to alcohol formation over partly reduced Ni catalysts instead of chain shortening hydrodecarbonylation. On comparing a commercial, conventionally used Adkins catalyst (consisting of 72 wt.% CuCr2O4 and 28 wt.% CuO) and novel bimetallic alumina supported composite (InNi/Al2O 3) producing alcohol with high selectivity, the chromium-free, environmental benign hydrogenation catalyst seems to be much more active.

Regulation of Iron-Catalyzed Olefin Hydroboration by Ligand Modifications at a Remote Site

Tseng, Kuei-Nin T.,Kampf, Jeff W.,Szymczak, Nathaniel K.

, p. 411 - 415 (2015)

An amide-derived N,N,N-Fe(II) complex catalyzes the hydroboration of alkenes at room temperature. Alkylation of a remote site on the ligand backbone was used as a late-stage modification to provide a more electrophilic complex as determined by electrochemical studies. The alkylated variant, compared to the parent complex, catalyzes olefin hydroboration with an increased reaction rate and exhibits distinct regioselectivity for internal alkene hydroboration. (Figure Presented).

Alkyne [2 + 2 + 2] Cyclotrimerization Catalyzed by a Low-Valent Titanium Reagent Derived from CpTiX3 (X = Cl, O- i-Pr), Me3SiCl, and Mg or Zn

Okamoto, Sentaro,Yamada, Takeshi,Tanabe, Yu-Ki,Sakai, Masaki

, p. 4431 - 4438 (2018)

Inter-, partially intra-, and intramolecular [2 + 2 + 2] cycloadditions of alkynes were catalyzed by a low-valent titanium species generated in situ from the reduction of CpTi(O-i-Pr)3, CpTiCl3, or Cp?TiCl3 with Mg or Zn powder in the presence of Me3SiCl. The role of Me3SiCl as an additive in the reaction mechanism is discussed.

Brown et al.

, p. 4233,4240 (1960)

Amides as Nucleophiles: Reaction of Alkyl Halides with Amides or with Amides and Water. A New Look at an Old Reaction

Brace, Neal O.

, p. 1804 - 1811 (1993)

Heating of formamide with an alkyl halide (with or without water) affords a mild, nonhydrolytic, high-yield synthesis of alcohols and formate esters.Yet the way in which substitution on the alkyl halide actually occurs remains obscure.To explore this question, thermal reaction of 1-bromooctane (1a) with formamides (HC(O)NHR, R=H, Me; 2a, 2b) was studied quantitatively.Major products are 1-octanol (3) and n-octyl formate (5); minor products are 1-octene (4), di-n-octyl ether (6), and N-octylformamide (7, from 2a, only).Solid coproduct is HC(=NR)NHR + Br(1-) (e.g., 8a, R=H, methanimidamide hydrobromide).Analogously, 1a and N-methylformamide (2b) give alkylated products 3,5, and 6 along with 8b (R=Me). 1-Iodooctane (1b) reacts similarly.Probe samples show that 1-octanol (3) is first formed, followed by 5 and 6.Occurence of 8a-c is key to a mechanistic interpretation of the reaction.An imidate ("salt I"), e.g., from 1a and 2b, is first formed and reacts with amide 2b to give and 3.Now alcohol 3 is converted to ester 5 and 8b by reaction with this same formylamidine.Water, if present, adds to the imidate and gives a new tetrahedral intermediate that cleaves to ester 5 and amide salt, RNH3X.Analogous reaction steps are proposed to generate side products 4, 6, and 7.Alkylation of formamide by C6F13CH2CH2I (1c) is considerably slower and less efficient than alkylation by 1-bromooctane.This result stands in sharp contrast to fast, efficient reaction of 1c with N-methylformamide or with DMF and water.

An efficient oxidative cleavage of carbon-silicon bonds by a dioxygen/hydroquinone system

Tamao,Hayashi,Ito

, p. 6533 - 6536 (1989)

Carbon-silicon bonds in alkylalkoxysilanes readily undergo cleavage by dioxygen in the presence of hydroquinone derivatives to give the corresponding alcohols in good yields. The real oxidant is dry hydrogen peroxide generated in situ. The oxidation proceeds with complete retention of configuration at an sp3 carbon center.

Thexylchloroborane. A Versatile Reagent for the Preparation of Mixed Thexyldiorganoboranes

Zweifel, George,Pearson, Norman R.

, p. 5919 - 5920 (1980)

-

H2-driven biotransformation of n-octane to 1-octanol by a recombinant Pseudomonas putida strain co-synthesizing an O2-tolerant hydrogenase and a P450 monooxygenase

Lonsdale, Thomas H.,Lauterbach, Lars,Honda Malca, Sumire,Nestl, Bettina M.,Hauer, Bernhard,Lenz, Oliver

, p. 16173 - 16175 (2015)

An in vivo biotransformation system is presented that affords the hydroxylation of n-octane to 1-octanol on the basis of NADH-dependent CYP153A monooxygenase and NAD+-reducing hydrogenase heterologously synthesized in a bacterial host. The hydrogenase sustains H2-driven NADH cofactor regeneration even in the presence of O2, the co-substrate of monooxygenase.

Unveiling the dual role of the cholinium hexanoate ionic liquid as solvent and catalyst in suberin depolymerisation

Ferreira, Rui,Garcia, Helga,Sousa, Andreia F.,Guerreiro, Marina,Duarte, Filipe J. S.,Freire, Carmen S. R.,Calhorda, Maria Jose,Silvestre, Armando J. D.,Kunz, Werner,Rebelo, Luis Paulo N.,Silva Pereira, Cristina

, p. 2993 - 3002 (2014)

Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liquid during suberin depolymerisation and during cleavage of standard compounds carrying key chemical functionalities was herein investigated. A clear demonstration that the ionic liquid catalyses the hydrolysis of acylglycerol ester bonds was attained herein, both experimentally and computationally (DFT calculations). This behaviour is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favourable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, whilst most of the linear aliphatic esters remained intact. The study emphasises that the ionic liquid plays the dual role of solvent and catalyst and leads to suberin efficient extraction through a mild depolymerisation. It is also one of the few reports of ionic liquids as efficient catalysts in the hydrolysis of esters.

Influence of sorption to dissolved humic substances on transformation reactions of hydrophobic organic compounds in water. Part II: Hydrolysis reactions

Georgi, Anett,Trommler, Ulf,Reichl, Annett,Kopinke, Frank-Dieter

, p. 1452 - 1460 (2008)

The effect of dissolved humic acid (HA) on two types of hydrolysis reactions was investigated: (I) dehydrochlorination of γ-hexachlorocyclohexane (HCH) and 1,1,2,2-tetrachloroethane (TeCA) as a reaction involving hydroxide ions (OH-) and (II) hydrolysis of 1-octyl acetate (OA) which is catalyzed by H+ at the applied pH value (pH 4.5). The rate of TeCA hydrolysis was not affected by addition of 2 g l-1 of HA at pH 10 (k′ = 0.33 h-1) but HCH hydrolysis was significantly inhibited (k′ = 4.6 × 10-3 h-1 without HA and 2.8 × 10-3 h-1 at 2 g l-1 HA). HCH is sorbed by 51% whereas TeCA sorption is insignificant at this HA concentration. Sorbed HCH molecules are effectively protected due to electrostatic repulsion of OH- by the net negative charge of the HA molecules. In contrast, OA hydrolysis at pH 4.5 (k′ = 1.6 × 10-5 h-1) was drastically accelerated after addition of 2 g l-1 HA (k′ = 1.1 × 10-3 h-1). The ratio of the pseudo-first-order rate constants of the sorbed and the freely dissolved ester fraction is about 70. H+ accumulation in the microenvironment of the negatively charged HA molecules was suggested to contribute to the higher reaction rate for the sorbed fraction in case of this H+-catalyzed reaction. Analogous effects from anionic surfactants are known as micellar catalysis.

MOF-derived Cu@C catalyst for the liquid-phase hydrogenation of esters

Zhao, Yujun,Wu, Xiaoqian,Zhou, Jiahua,Wang, Yue,Wang, Shengping,Ma, Xinbin

, p. 883 - 886 (2018)

MOF derived core-shell Cu@C was prepared by the pyrolysis of Cu-BTC and applied in the liquid-phase hydrogenation of ester. The severe aggregation of copper species was inhibited by the carbon shell. Compared with traditional Cu/AC-H2 catalyst, Cu@C-N2 displayed higher activity in the hydrogenation of butyl butyrate due to its higher Cu dispersion. Further reduction of Cu@C-N2 catalyst in H2 greatly improved the activity, as a result of the appropriate ratio of Cu+/Cu0, which can activate both ester and H2 molecules.

Mild and efficient tetrahydropyranylation and deprotection of alcohols catalyzed by heteropoly acids

Molnar, Arpad,Beregszaszi, Timea

, p. 8597 - 8600 (1996)

A simple, mild and effective method to form 2-tetrahydropyranyl ethers of alcohols and phenol and the removal of this protective group in the presence of heteropoly acids as catalysts are described.

Electrocatalytic hydrogenation of octyl aldehyde over Pd catalysts

Cirtiu, Ciprian M.,Menard, Hugues

, p. 475 - 478 (2007)

The electrocatalytic hydrogenation (ECH) of octyl aldehyde (octanal) to octyl alcohol (octan-1-ol) was investigated using commercial Pd/alumina catalysts in aqueous ethanol. The influence of different parameters, such as catalyst support, current intensity, polarity of solvent, supporting electrolyte, and octanal concentration, on the electrocatalytic hydrogenation of octanal was studied.

Hydrolysis of Water-insoluble Esters by Octadecyl Immobilized H-ZSM-5 Catalyst in a Water-Toluene System

Ogawa, Haruo,Tensai, Koh,Taya, Kazuo,Chihara, Teiji

, p. 1246 - 1247 (1990)

In the hydrolysis of water-insoluble esters in a water-toluene system octadecyltrichlorosilane-treated ZSM-5, which floated at the interface of the two liquids, was observed to be a solid interface catalyst.

A Remarkably Simple Class of Imidazolium-Based Lipids and Their Biological Properties

Wang, Da,Richter, Christian,Rühling, Andreas,Drücker, Patrick,Siegmund, Daniel,Metzler-Nolte, Nils,Glorius, Frank,Galla, Hans-Joachim

, p. 15123 - 15126 (2015)

A series of imidazolium salts bearing two alkyl chains in the backbone of the imidazolium core were synthesized, resembling the structure of lipids. Their antibacterial activity and cytotoxicity were evaluated using Gram-positive and Gram-negative bacteria and eukaryotic cell lines including tumor cells. It is shown that the length of alkyl chains in the backbone is vital for the antibiofilm activities of these lipid-mimicking components. In addition to their biological activity, their surface activity and their membrane interactions are shown by film balance and quartz crystal microbalance (QCM) measurements. The structure-activity relationship indicates that the distinctive chemical structure contributes considerably to the biological activities of this novel class of lipids. Lipids! A series of imidazolium salts bearing two alkyl chains in the backbone were synthesized, resembling the structure of lipids. The biological activity resulting from their surface activity and membrane interaction are shown (see figure), which were determined by the alkyl chain length.

Selective Electroenzymatic Oxyfunctionalization by Alkane Monooxygenase in a Biofuel Cell

Abdellaoui, Sofiene,Chen, Hui,Kummer, Matthew J.,Malapit, Christian A.,Minteer, Shelley D.,You, Chun,Yuan, Mengwei

, p. 8969 - 8973 (2020)

Aliphatic synthetic intermediates with high added value are generally produced from alkane sources (e.g., petroleum) by inert carbon–hydrogen (C?H) bond activation using classical chemical methods (i.e. high temperature, rare metals). As an alternative approach for these reactions, alkane monooxygenase from Pseudomonas putida (alkB) is able to catalyze the difficult terminal oxyfunctionalization of alkanes selectively and under mild conditions. Herein, we report an electrosynthetic system using an alkB biocathode which produces alcohols, epoxides, and sulfoxides through bioelectrochemical hydroxylation, epoxidation, sulfoxidation, and demethylation. The capacity of the alkB binding pocket to protect internal functional groups is also demonstrated. By coupling our alkB biocathode with a hydrogenase bioanode and using H2 as a clean fuel source, we have developed and characterized a series of enzymatic fuel cells capable of oxyfunctionalization while simultaneously producing electricity.

Novel hydroborating agents from Silylamine-boranes

Soderquist, John A.,Medina, Jesus R.,Huertas, Ramon

, p. 6119 - 6122 (1998)

Exhibiting a broad spectrum of hydroboration reactivities, seven (7) new silylamine-borane complexes (1) were efficiently prepared from diborane and the corresponding silylated amines (2). Most are crystalline solids which are air-stable, concentrated borane sources. All provide convenient alternatives to other hydroborating agents, 2 undergoing complete hydrolysis to volatile and/or water soluble by-products upon aqueous work-up, thereby greatly facilitating the isolation of the borane-derived reaction products.

Asymmetric transformation of enones with Synechococcus sp. PCC 7942

Shimoda, Kei,Kubota, Naoji,Hamada, Hiroki,Yamane, Shin-Ya,Hirata, Toshifumi

, p. 2269 - 2272 (2004)

Asymmetric transformation of enones was investigated with cultured cells of Synechococcus sp. PCC 7942 (a cyanobacterium). The cells reduced both the endocyclic C-C double bond of s-trans enones and the exocyclic C-C double bond of s-cis enones with high enantioselectivity to afford optically active α-substituted (S)-ketones under illumination. In addition, the reduction of the double bond of these enones was accompanied by the formation of saturated alcohols. The cells preferentially reduced simple aliphatic ketones rather than cyclic ones to the corresponding (S)-alcohols with excellent enantioselectivity.

Regiodivergent Reductive Opening of Epoxides by Catalytic Hydrogenation Promoted by a (Cyclopentadienone)iron Complex

De Vries, Johannes G.,Gandini, Tommaso,Gennari, Cesare,Jiao, Haijun,Pignataro, Luca,Stadler, Bernhard M.,Tadiello, Laura,Tin, Sergey

, p. 235 - 246 (2022/01/03)

The reductive opening of epoxides represents an attractive method for the synthesis of alcohols, but its potential application is limited by the use of stoichiometric amounts of metal hydride reducing agents (e.g., LiAlH4). For this reason, the corresponding homogeneous catalytic version with H2 is receiving increasing attention. However, investigation of this alternative has just begun, and several issues are still present, such as the use of noble metals/expensive ligands, high catalytic loading, and poor regioselectivity. Herein, we describe the use of a cheap and easy-To-handle (cyclopentadienone)iron complex (1a), previously developed by some of us, as a precatalyst for the reductive opening of epoxides with H2. While aryl epoxides smoothly reacted to afford linear alcohols, aliphatic epoxides turned out to be particularly challenging, requiring the presence of a Lewis acid cocatalyst. Remarkably, we found that it is possible to steer the regioselectivity with a careful choice of Lewis acid. A series of deuterium labeling and computational studies were run to investigate the reaction mechanism, which seems to involve more than a single pathway.

BiCl3-Facilitated removal of methoxymethyl-ether/ester derivatives and DFT study of -O-C-O- bond cleavage

Pacherille, Angela,Tuga, Beza,Hallooman, Dhanashree,Dos Reis, Isaac,Vermette, Mélodie,Issack, Bilkiss B.,Rhyman, Lydia,Ramasami, Ponnadurai,Sunasee, Rajesh

supporting information, p. 7109 - 7116 (2021/05/03)

A simple method for the cleavage of methoxymethyl (MOM)-ether and ester derivatives using bismuth trichloride (BiCl3) is described. The alkyl, alkenyl, alkynyl, benzyl and anthracene MOM ether derivatives, as well as MOM esters of both aliphatic and aromatic carboxylic acids, were deprotected in good yields. To better understand the molecular roles of BiCl3and water for MOM cleavage, two possible binding pathways were investigated using the density functional theory (DFT) method. The theoretical results indicate the differential initial binding site preferences of phenolic and alcoholic MOM substrates to the Bi atom and suggest that water plays a key role in facilitating the cleavage of the MOM group.

Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)

Hendy, Cecilia M.,Jui, Nathan T.,Lian, Tianquan,Smith, Gavin C.,Xu, Zihao

supporting information, p. 8987 - 8992 (2021/07/01)

We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.

KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols

Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian

supporting information, p. 12776 - 12779 (2021/12/10)

Selective reduction of aldehydes and ketones to their corresponding alcohols with KB3H8, an air- and moisture-stable, nontoxic, and easy-to-handle reagent, in water and THF has been explored under an air atmosphere for the first time. Control experiments illustrated the good selectivity of KB3H8 over NaBH4 for the reduction of 4-acetylbenzaldehyde and aromatic keto esters. This journal is

Process route upstream and downstream products

Process route

methanol
67-56-1

methanol

di-n-octyl ether
629-82-3

di-n-octyl ether

octanol
111-87-5

octanol

1,1-dimethoxyoctane
10022-28-3

1,1-dimethoxyoctane

Conditions
Conditions Yield
In acetic acid; for 5.4h; Yield given; electrolysis: platinum-plate anode, carbon-rod cathode, Bu4NBF4, 20 F/mol, 0.5 A, 20 V;
4-tetrahydrofuran-2-yl-butan-2-ol
3208-43-3,4527-76-8

4-tetrahydrofuran-2-yl-butan-2-ol

2-butanyltetrahydrofuran
1004-29-1

2-butanyltetrahydrofuran

octanol
111-87-5

octanol

di-n-octyl ether
629-82-3

di-n-octyl ether

Conditions
Conditions Yield
With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen; at 150 ℃; for 15h; under 90009 Torr; Reagent/catalyst; Ionic liquid;
58.6%
27.1%
9.1%
With 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen; at 150 ℃; for 15h; under 90009 Torr; Reagent/catalyst; Ionic liquid;
25.8%
44.9%
26.1%
With N,N,N-tributyl-1-(4-butylsulfonic acid)-aminium bis(trifluoromethylsulfonyl)imide; hydrogen; at 150 ℃; for 15h; under 90009 Torr; Reagent/catalyst; Ionic liquid;
11.7%
41.5%
34.5%
With 5 wt% ruthenium/carbon; hydrogen; at 150 ℃; for 15h; under 90009 Torr; Ionic liquid;
furfural
98-01-1

furfural

acetone
67-64-1

acetone

2-butanyltetrahydrofuran
1004-29-1

2-butanyltetrahydrofuran

octanol
111-87-5

octanol

di-n-octyl ether
629-82-3

di-n-octyl ether

Conditions
Conditions Yield
furfural; acetone; With sodium hydroxide; at 20 ℃; for 15h;
With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen; at 120 ℃; for 2h; under 90009 Torr; Ionic liquid;
With hydrogen; at 150 ℃; for 60h; under 90009 Torr; Acidic conditions; Ionic liquid;
23.5%
32.5%
19.8%
furfural; acetone; With sodium hydroxide; at 20 ℃; for 16h;
With ruthenium-carbon composite; hydrogen; at 120 ℃; for 2h; under 90009 Torr; Ionic liquid;
With ruthenium-carbon composite; hydrogen; at 150 ℃; for 60h; under 90009 Torr; Ionic liquid;
4-(furan-2-yl)but-3-en-2-one
623-15-4

4-(furan-2-yl)but-3-en-2-one

2-butanyltetrahydrofuran
1004-29-1

2-butanyltetrahydrofuran

octanol
111-87-5

octanol

di-n-octyl ether
629-82-3

di-n-octyl ether

Conditions
Conditions Yield
4-(furan-2-yl)but-3-en-2-one; With ruthenium-carbon composite; 1-(4-butylcarboxylic acid)-3-(n-butyl)-imidazolium bis(trifluoromethylsulfonyl)imide; hydrogen; at 120 ℃; for 2h; under 90009 Torr; Ionic liquid;
With hydrogen; at 150 ℃; for 45h; under 90009 Torr; Reagent/catalyst; Acidic conditions; Ionic liquid;
5.4%
48.4%
44.2%
4-(furan-2-yl)but-3-en-2-one; With 5 wt% ruthenium/carbon; hydrogen; at 120 ℃; for 2h; under 90009 Torr;
With hydrogen; at 150 ℃; for 60h; under 90009 Torr; Ionic liquid;
Conditions
Conditions Yield
With oxygen; at 450 ℃; Reagent/catalyst; Temperature; Catalytic behavior; Mechanism; Gas phase;
4-tetrahydrofuran-2-yl-butan-2-ol
3208-43-3,4527-76-8

4-tetrahydrofuran-2-yl-butan-2-ol

2-butanyltetrahydrofuran
1004-29-1

2-butanyltetrahydrofuran

octane
111-65-9

octane

octanol
111-87-5

octanol

di-n-octyl ether
629-82-3

di-n-octyl ether

Conditions
Conditions Yield
With ruthenium-carbon composite; hydrogen; toluene-4-sulfonic acid; at 150 ℃; for 15h; under 90009 Torr; Reagent/catalyst;
8.7%
24.7%
51.9%
8.5%
4-tetrahydrofuran-2-yl-butan-2-ol
3208-43-3,4527-76-8

4-tetrahydrofuran-2-yl-butan-2-ol

2-butanyltetrahydrofuran
1004-29-1

2-butanyltetrahydrofuran

octane
111-65-9

octane

octanol
111-87-5

octanol

Conditions
Conditions Yield
With hydrogen; In n-heptane; at 175 ℃; for 18h; under 37503.8 Torr; Autoclave;
61 %Chromat.
10 %Chromat.
7 %Chromat.
octyl benzylcarbamate

octyl benzylcarbamate

methanol
67-56-1

methanol

octanol
111-87-5

octanol

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen; In toluene; at 130 ℃; for 48h; under 15001.5 Torr;
81 %Spectr.
99 %Chromat.
98 %Chromat.
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

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

acetaldehyde

trans-Crotonaldehyde
123-73-9,4170-30-3

trans-Crotonaldehyde

octanol
111-87-5

octanol

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

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

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

ethyl acetate
141-78-6

ethyl acetate

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

5-hexanolide
823-22-3,26991-67-3

5-hexanolide

butan-1-ol
71-36-3

butan-1-ol

hexan-1-ol
111-27-3

hexan-1-ol

Conditions
Conditions Yield
With pyridine; titanium(IV) oxide; hydrogen; In water; at 229.84 ℃; for 6h; under 757.576 Torr; Inert atmosphere;

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