10032-05-0Relevant articles and documents
A novel application of terminal alkynes as the homogeneous catalysts for acetalization and esterification
Sekerová, Lada,Vysko?ilová, Eli?ka,?erveny, Libor,Sedlá?ek, Jan
, p. 2877 - 2882 (2019)
The theoretical study focused on the possible use of low-molecular-weight mono-as well as multifunctional terminal alkynes as catalysts for two reactions, which are known to be typically acid catalyzed - acetalization and esterification, is presented in this study. Multifunctional terminal alkynes [(diethynylbenzenes, triethynylbenzene, and tetrakis(4-ethynylphenyl)methane]were significantly more active than the monofunctional ones (cyclopropylacetylene, phenylacetylene, 3-cyclohexylprop-1-yne, 1-ethynyl-2-fluorobenzene, 1-ethynyl-4-fluorobenzene, 4-ethynyltoluene, 4-tert-butylphenylacetylene, and 2-ethynyl-α,α,α-trifluorotoluene), this fact can be partly explained by the higher amount of ethynyl groups per alkyne molecule. We confirmed that terminal ethynyl groups in low-molecular-weight alkynes can successfully act as acid catalytic centers for acetalization as well as for esterification.
Low pressure hydroformylation in the presence of alcohol promoters
Li, Baitao,Li, Xiaohong,Asami, Kenji,Fujimoto, Kaoru
, p. 836 - 837 (2002)
Active carbon supported cobalt catalyst was studied for the hydroformylation of 1-hexene in the presence of alcohol solvents at low pressure. The influence of various solvents on the hydroformylation and the CO conversion vs time on stream were investigated in detail. It was found that the heterogeneous catalyst shows excellent activity only in the alcohol solvents.
A simple one-pot procedure for the conversion of aldehydes to methyl esters
Rhee, Hakjune,Kim, Jin Yeon
, p. 1365 - 1368 (1998)
Several methyl esters were obtained by an efficient and simple one-pot procedure from the corresponding aldehydes in high yields. This procedure involves dimethyl acetal formation from aldehydes and subsequent oxidation.
A convenient and highly efficient method for the protection of aldehydes using very low loading hydrous ruthenium(III) trichloride as catalyst
Qi, Jian-Ying,Ji, Jian-Xin,Yueng, Chi-Hung,Kwong, Hoi-Lun,Chan, Albert S.C.
, p. 7719 - 7721 (2004)
A convenient method for the chemoselective protections of both aliphatic and aromatic aldehydes has been developed. Ruthenium(III) trichloride (0.1 mol %) has found to be an highly efficient catalyst in the acetalizations of aldehydes with various simple alcohols such as methanol, ethanol, or diols such as 1,2-ethylanediol and 1,3-propanediol under mild reaction conditions.
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Hassner,A. et al.
, p. 1962 - 1964 (1970)
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Metal organic frameworks as solid acid catalysts for acetalization of aldehydes with methanol
Dhakshinamoorthy, Amarajothi,Alvaro, Mercedes,Garcia, Hermenegildo
, p. 3022 - 3030 (2010)
Room temperature acetalization of aldehydes with methanol has been carried out using metal organic frameworks (MOFs) as solid heterogeneous catalysts. Of the MOFs tested, a copper-containing MOF [Cu3(BTC)2] (BTC=1,3,5-benzenetricarboxylate) showed better catalytic activity than an iron-containing MOF [Fe(BTC)] and an aluminium containing MOF [Al 2(BDC)3] (BDC=1,4-benzenedicarboxylate). The protocol was validated for a series of aromatic and aliphatic aldehydes and used to protect various aldehydes into commercially important acetals in good yields without the need of water removal. In addition, the reusability and heterogeneity of this catalytic system was demonstrated. The structural stability of MOF was further studied by characterization with powder X-ray diffraction, Brunauer-Emmett- Teller surface area measurements and Fourier-transformed infrared spectroscopic analysis of a deactivated catalyst used to convert a large amount of benzaldehyde. The performance of copper MOF as acetalization catalyst compares favourably with those of other conventional homogeneous and heterogeneous catalysts such as zinc chloride, zeolite and clay. Copyright
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Nokami,J. et al.
, p. 1045 - 1046 (1979)
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Photochemical Hydroformylation of Olefins in the Cobalt-Phosphine Catalyst System
Mori, Sadayuki,Tatsumi, Shunji,Yasuda, Masaki,Kudo, Kiyoshi,Sugita, Nobuyuki
, p. 3017 - 3022 (1991)
Cobalt-catalyzed hydroformylation of olefins was found to proceed even at ambient temperature under UV irradiation in the presence of phosphine.Extremely high selectivity toward straight-chain aldehyde (99percent in case of 1-hexene) was obtained by lower
Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
, (2020/01/13)
Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
Phosphine-ligated Ir(III)-complex as a bi-functional catalyst for one-pot tandem hydroformylation-acetalization
Liu, Huan,Liu, Lei,Guo, Wen-Di,Lu, Yong,Zhao, Xiao-Li,Liu, Ye
, p. 215 - 221 (2019/04/17)
The complexation of IrCl3?3H2O with the electron-deficient phosphines (L1-L6) respectively afforded a bi-functional catalyst possessing the dual functions of transition metal complex (IrIII-P) and IrIII-Lewis acid for tandem hydroformylation-acetalization of olefins. The best result was obtained over L5-based IrCl3?3H2O catalytic system which corresponded to 97% conversion of 1-hexene along with 92% selectivity to the target acetals free of any additive. The crystal structure of the novel IrIII-complex of IrIII-L4 indicated that the electron-deficient nature of the involved phosphine warranted Ir-center in +3 valence state without reduction, which served as the Lewis acid catalyst for the subsequent acetalization of the aldehydes as well. Moreover, as an ionic phosphine, L6-based IrCl3?3H2O system immobilized in RTIL of [Bmim]PF6 could be recycled for 6 runs without the obvious activity loss or metal leaching.
