5921-80-2Relevant academic research and scientific papers
One-step solvent-free aerobic oxidation of aliphatic alcohols to esters using a tandem Sc-Ru?MOF catalyst
Feng, Tingkai,Li, Conger,Li, Tao,Zhang, Songwei
, p. 1474 - 1480 (2022/03/08)
Esters are an important class of chemicals in industry. Traditionally, ester production is a multi-step process involving the use of corrosive acids or acid derivatives (e.g. acid chloride, anhydride, etc.). Therefore, the development of a green synthetic protocol is highly desirable. This work reports the development of a metal-organic framework (MOF) supported tandem catalyst that can achieve direct alcohol to ester conversion (DAEC) using oxygen as the sole oxidizing agent under strictly solvent-free conditions. By incorporating Ru nanoparticles (NPs) along with a homogeneous Lewis acid catalyst, scandium triflate, into the nanocavities of a Zr MOF, MOF-808, the compound catalyst, Sc-Ru?MOF-808, can achieve aliphatic alcohol conversion up to 92% with ester selectivity up to 91%. A mechanistic study reveals a unique “via acetal” pathway in which the alcohol is first oxidized on Ru NPs and rapidly converted to an acetal on Sc(iii) sites. Then, the acetal slowly decomposes to release an aldehyde in a controlled manner for subsequent oxidation and esterification to the ester product. To the best of our knowledge, this is the first example of DAEC of aliphatic alcohols under solvent-free conditions with high conversion and ester selectivity.
Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates
Ishida, Naoki,Kawasaki, Tairin,Murakami, Masahiro,Tosaki, Tomohiro
supporting information, p. 7683 - 7687 (2021/10/12)
A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.
SATURATED HOMOETHER MANUFACTURING METHOD FROM UNSATURATED CARBONYL COMPOUND
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Paragraph 0045-0046, (2020/05/14)
PROBLEM TO BE SOLVED: To provide a method for manufacturing saturated homoether from an unsaturated carboxyl compound at good efficiency. SOLUTION: There is provided a manufacturing method of saturated homoether using an unsaturated carboxyl compound and hydrogen as raw materials, and a catalyst in which a metal is carried on an acidic catalyst carrier. The metal of the catalyst is for example palladium, and the carrier of the catalyst is alumina, silica, silica-alumina, or the like. The unsaturated carbonyl compound as the raw material is 2-butenal, 2-ethyl-2-hexenal, 2-ethyl-2-butenal, 2-hexenal, and manufactured saturated homoether is dibuthylether, bis(2-ethylhexyl)ether, bis(2-ethylbuty)ether, dihexylether, or the like. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPO&INPIT
Photocatalytic Conversion of a FeCl3–CCl4–ROH System
Makhmutov
, p. 695 - 700 (2018/03/08)
The photocatalytic transformations of carbon tetrachloride and aliphatic primary alcohols in the presence of iron trichloride and a molar ratio of components FeCl3: CCl4: ROH = 1: 300: 2550 were studied. CCl4 is transformed into chloroform and hexachloroethane after exposure to a mercury lamp (250 W) to the FeCl3–CCl4–ROH system at 20°C, whereas the primary ROH alcohols are selectively oxidized into acetals (1,1-dialkoxyalkanes). The maximum conversion of CCl4 reaches 80%. The kinetics and mechanism of the photocatalytic conversion of the FeCl3–CCl4–ROH system are considered.
Acetals from primary alcohols with the use of tridentate proton responsive phosphinepyridonate iridium catalysts
Sahoo,Jiang,Bruneau,Sharma,Suresh,Achard
, p. 100554 - 100558 (2016/11/09)
The association of the new phosphinepyridonate ligands along with an iridium metallic precursor resulted in the selective acetalization of various primary alcohols via a formal dehydrogenative coupling reaction.
The levels of fatty alcohol dehydrogenation coupling method for preparing aldehyde-acetal
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Paragraph 0029; 0030, (2016/10/08)
The invention discloses a method for preparing acetal by dehydrogenation coupling of first-stage fatty alcohol. The method comprises the following steps: adding alcohol reaction liquid to commercial titanium dioxide P25, and simultaneously adding a precious metals source solution; vacuumizing or introducing argon under magnetic agitation; stopping vacuumizing or introducing argon after oxygen in the system is removed; turning on an ultraviolet light source; reducing a precious metal source into precious metal particles by in-situ photocatalysis, and loading to the titanium dioxide surface; carrying out dehydrogenation coupling on catalyzed alcohol to form the acetal; controlling the reaction temperature at 10-70 DEG C and the reaction time at 10-72 hours; separating a catalyst through centrifugal participation, vacuum filtration or static precipitation after the reaction is ended, and then carrying out reduced pressure distillation to remove alcohol, so as to obtain the acetal product. The method has the advantages of high selectivity, high yield, low cost and the like, and is environmental friendly, and the purity can be up to over 97%.
TiO2-photocatalytic acceptorless dehydrogenation coupling of primary alkyl alcohols into acetals
Zhang, Hongxia,Zhu, Zhenping,Wu, Yupeng,Zhao, Tianjian,Li, Li
, p. 4076 - 4080 (2014/10/15)
Primary alkyl alcohols can be directly converted into acetals and H 2via TiO2-photocatalytic dehydrogenation coupling at room temperature, with no need for any hydrogen acceptors. The reaction follows a tandem process integrating photocatalytic alcohol dehydrogenation and H +-catalytic acetalation, in which the H+ ion catalysts are provided by the alcohol dehydrogenation in real time. This approach exhibits a very high reaction rate and product selectivity, and represents a novel green process for the conversion of primary alkyl alcohols, especially for bio-renewable ethanol and 1-butanol. the Partner Organisations 2014.
Copper-catalyzed dehydrogenative coupling of arenes with alcohols
Bhadra, Sukalyan,Matheis, Christian,Katayev, Dmitry,Goo?en, Lukas J.
supporting information, p. 9279 - 9283 (2013/09/12)
What a couple! Arenes functionalized with donating groups undergo oxidative dehydrogenative coupling with alcohols in the presence of a copper/silver catalyst system. This intermolecular C-H alkoxylation provides a convenient synthetic route to the important class of aryl ethers. The catalyst system also allows the alkoxylation of benzylic C-H groups with formation of benzyl alkyl ethers. Copyright
Expanding the scope of biomass-derived chemicals through tandem reactions based on oxorhenium-catalyzed deoxydehydration
Shiramizu, Mika,Toste, F. Dean
supporting information, p. 12905 - 12909 (2014/01/06)
New modes of DODH: Oxorhenium compounds act as deoxydehydration(DODH)/acid dual-purpose catalysts to transform biomass-derived diol substrates into a variety of commodity chemical precursors. The power of this approach is highlighted by a tandem [1,3]-OH shift/DODH of 2-ene-1,4-diols and 2,4-diene-1,6-diols, and by a DODH/esterification sequence of sugar acids to unsaturated esters for the production of polymers and plasticizers. Copyright
Selective acceptorless conversion of primary alcohols to acetals and dihydrogen catalyzed by the ruthenium(II) complex Ru(PPh3) 2(NCCH3)2(SO4)
Kossoy, Elizaveta,Diskin-Posner, Yael,Leitus, Gregory,Milstein, David
experimental part, p. 497 - 504 (2012/04/23)
The complex bis(acetonitrile)bis(triphenylphosphine)ruthenium(II) sulfate [Ru(PPh3)2(NCCH3)2(SO4)], fully characterized spectroscopically and by a single crystal X-ray study, catalyzes at 110 °C the direct transformation of primary alcohols to the corresponding acetals with liberation of molecular hydrogen. The formation of acetals proceeds via direct substitution of the hydroxy group of the hemiacetal intermediate by an alcohol molecule. The closely related bis(triphenylphosphine) ruthenium(II) acetate [Ru(PPh3)2(OAc)2] catalyzes the conversion of primary alcohols to the corresponding esters rather than acetals. Copyright
