2568-96-9Relevant academic research and scientific papers
Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst
Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui
supporting information, p. 18591 - 18598 (2021/06/28)
A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.
Synthesis of unsymmetrical alkyl acetals via addition of primary alcohols to allyl ethers mediated by ruthenium complexes
Krompiec, Stanislaw,Penkala, Mateusz,Kowalska, Ewelina,Penczek, Robert,Bujak, Piotr,Danikiewicz, Witold,Spolnik, Grzegorz,Kita, Andrzej,Grudzka, Iwona
experimental part, p. 1241 - 1247 (2012/06/04)
Ru-catalyzed synthesis of mixed alkyl-alkyl acetals via addition of primary alcohols to allyl ethers has been extended to include long-chain and/or functionalized substrates. The catalytic systems for these reactions were generated from RuCl2(PPh3)3 and [RuCl 2(1,5-COD)]x and phosphines [PPh3 or P(p-chlorophenyl)3] or SbPh3. Of particular importance is the almost quantitative elimination of transacetalization. The addition proceeds through allyl complexes, not via isomerization of allyl ethers - subsequent addition of ROH to vinyl ethers. The Author(s) 2011.
Facile preparation of ionic liquid functionalized magnetic nano-solid acid catalysts for acetalization reaction
Wang, Ping,Kong, Aiguo,Wang, Wenjuan,Zhu, Haiyan,Shan, Yongkui
scheme or table, p. 159 - 164 (2010/08/06)
The facile two-step preparation procedure of a novel magnetic nano-solid acid catalyst is described, which includes grafting an ionic liquid onto Fe 3O4 nanoparticles, followed by the sulfonation of phenyl groups in the ionic liquid. The catalytic performance of this novel material has been systematically studied in the acetal formation of benzaldehyde and ethylene glycol. The experimental results testify this catalyst possesses high catalytic activity with a yield of 97% under mild reaction conditions. Furthermore, the catalyst is readily separated using a permanent magnet and it is reusable without any significant decrease in catalytic activity.
[Hmim]3PW12O40: A high-efficient and green catalyst for the acetalization of carbonyl compounds
Dai, Yan,Li, Bin Dong,Quan, Heng Dao,Lü, Chun Xu
experimental part, p. 678 - 681 (2011/10/31)
[Hmim]3PW12O40 was developed and used in the acetalization of carbonyl compounds in excellent yields. The ionic liquid-heteropoly acid hybrid compound and reaction medium formed temperature-dependent phase-separation system with the ease of product as well as catalyst separation. The catalyst was recycled more than 10 times without any apparent loss of catalytic activity.
A green procedure for the protection of carbonyl compounds catalyzed by iodine in ionic liquid
Ren, Yi-Ming,Cai, Chun
body text, p. 7110 - 7112 (2015/04/15)
Aldehydes and ketones are protected with ethylene glycol in the presence of a catalytic amount of iodine in PEG ionic liquid (IL 400) under mild conditions to afford the corresponding ketals in good yields. The recovery of iodine is facilitated by the ionic liquid. The recovered catalyst was reused six times with consistent activity.
A remarkable iodine-catalyzed protection of carbonyl compounds
Banik, Bimal K.,Chapa, Marin,Marquez, Jocabed,Cardona, Magda
, p. 2341 - 2343 (2007/10/03)
We report here a remarkably simple molecular iodine-catalyzed protection method for various carbonyl compounds as ketals in a general reaction. The iodine-catalyzed reaction of mandelic acid and lactic acid with several aldehydes has furnished a highly diastereoselective synthesis of cis and trans dioxolanones.
Application of Functional Ionic Liquids Possessing Two Adjacent Acid Sites for Acetalization of Aldehydes
Li, Dongmei,Shi, Feng,Peng, Jiajian,Guo, Shu,Deng, Youquan
, p. 3582 - 3585 (2007/10/03)
Several acid functional ionic liquids, in which cations possess two adjacent acid sites, were synthesized and used for the acetalization of aldehydes with good catalytic performance under mild reaction conditions.
Highly selective isomerization of allyloxyalcohols to cyclic acetals or 1-propenyloxyalcohols
Urbala, Magdalena,Ku?nik, Nikodem,Krompiec, Stanis?aw,Rzepa, Józef
, p. 1203 - 1206 (2007/10/03)
Highly selective isomerization of allyloxyalcohols either to 1-propenyl derivatives or to cyclic acetals of propanal depending on the transition metal (Ru, Rh) complex used is described together with a proposed explanation of an alternative reaction, which permits broad application of the described method.
Synthesis of monoprotected 1,4-diketones by photoinduced alkylation of enones with 2-substituted-1,3-dioxolanes
Mosca, Raffaella,Fagnoni, Maurizio,Mella, Mariella,Albini, Angelo
, p. 10319 - 10328 (2007/10/03)
Photosensitized hydrogen abstraction from 2-alkyl-1,3-dioxolanes by triplet benzophenone gives the corresponding 1,3-dioxolan-2-yl radicals and these are trapped by α,β-unsatured ketones yielding monoprotected 1,4-diketones. With open chain ketones (3-buten-2-one and 4-penten-3-one) the yields are low and competitive pathways in part consume the radicals. With cyclic enones however, yields are good as tested with cyclopentenone, cyclohexenone and 4-hydroxy-cyclopentenone. More generally, this is a viable alternative for the synthesis of 1,4-diketones via radicals while the thermal initiation gives only low yield. The reaction cannot be extended to strongly stabilized radicals, such as the 2-phenyl-1,3-dioxolanyl radical.
Hydroxyl radical reaction rate constant and atmospheric transformation products of 2-propoxyethanol
Markgraf, Stewart J.,Semples, John,Wells
, p. 315 - 322 (2007/10/03)
The relative rate technique has been used to measure the hydroxyl radical (OH) reaction rate constant of 2-propoxyethanol (2PEOH, CH3CH2CH2OCH2CH2(OH)). 2PEOH reacts with OH with a bimolecular rate constant of (21.4±6.0)×10-12 cm3 molecule-1 s-1 at 297±3 K and 1 atm total pressure, which is a little larger than previously reported. Assuming an average OH concentration of 1×106 molecules cm-3, an atmospheric lifetime of 13 h is calculated for 2PEOH. In order to more clearly define this hydroxy ether's atmospheric reaction mechanism, an investigation into the OH+2PEOH reaction products was also conducted. The OH+2PEOH reaction products and yields observed were: propyl formate (PF, 47±2%, CH3CH2CH2OC(double bond O)H), 2 propoxyethanal (CH3CH2CH2OCH2C(double bond O)H 15±1%), and 2-ethyl-1,3-dioxolane (5.4±0.4%). The 2PEOH reaction mechanism is discussed in light of current understanding of oxygenated hydrocarbon atmospheric chemistry. The findings reported here can be related to other structurally similar alcohols and may impact regulatory tools such as ground-level ozone-forming potential calculations (incremental reactivity).
