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107-18-6Relevant articles and documents
Selective pyrolysis of bifunctional compounds: gas-phase elimination of carbonate-ester functionalities
Al-Azemi, Talal F.,Dib, Hicham H.,Al-Awadi, Nouria A.,El-Dusouqui, Osman M.E.
, p. 4126 - 4134 (2008)
Compounds containing both carbonate and ester functionalities were synthesized and then subjected to online-GC gas-phase pyrolysis. The carbonate groups were cleaved selectively in all elimination reactions. The end products of the reaction were found to be affected by the nature of the substrate. The presence of hydrogen and carbonyl substituents on the carbon β to the carbonate group resulted in further product decomposition through a concerted six-membered transition state. Results from flash vacuum pyrolysis (FVP) and analysis of the GC data indicate that the cleavage of the carbonate group is fast, and that the slower secondary decomposition reactions are independent of the presence of the carbonate group. Spectroscopic analyses of the products are reported.
Highly selective transfer hydrogenation of α,β-unsaturated carbonyl compounds using Cu-based nanocatalysts
Siddqui, Nazia,Sarkar, Bipul,Pendem, Chandrashekar,Khatun, Rubina,Sivakumar Konthala,Sasaki, Takehiko,Bordoloi, Ankur,Bal, Rajaram
, p. 2828 - 2837 (2017)
Simultaneous dehydrogenation of cyclohexanol to cyclohexanone and hydrogenation of α,β-unsaturated carbonyl compounds to corresponding α,β-unsaturated alcohols was carried out in a single pot reaction without addition of any external hydrogen donor. Cu nanoclusters supported on nanocrystalline MgO were found to be the active catalyst for the chemoselective transfer hydrogenation of unsaturated carbonyl compounds to produce the corresponding alcohols with very high yields. Transfer hydrogenation of cyclohexanol and cinnamaldehyde produced cyclohexanone and cinnamyl alcohol with 100% selectivity. This Cu/MgO catalyst can be easily recovered and recycled up to more than five times without any significant loss of activity, which confirmed the true heterogeneous nature of this catalyst. Several α,β-unsaturated compounds were also tested for this reaction and it was found that for all the cases the yield is >95%. The ease of handling without requiring high pressure H2 or a hazardous hydrogen source makes this transfer hydrogenation more practical and useful.
IR study of alkene allylic activation on magnesium ferrite and alumina catalysts
Busca, Guido,Finocchio, Elisabetta,Lorenzelli, Vincenzo,Trombetta, Marcella,Rossini, Stefano A.
, p. 4687 - 4694 (1996)
The interaction of propene and butenes with oxydehydrogenation catalyst, MgFe2O4, and with an isomerization catalyst, γ-Al2O3, have been studied by FTIR spectroscopy.Allyloxy species (prop-2-en-1-oxides from propene and but-3-en-2-oxide from but-1-ene) were observed over MgFe2O4, while allyl species (prop-2-en-1-yl from propene, but-3-en-2-yl from but-1-ene and 2-methylprop-2-en-1-yl from isobutene), thought to be ?-bonded to Al3+ ions, were observed over γ-Al2O3.It is proposed that on all cases the allylic C-H bond is heterolytically broken at cation-anion couples (Mn+O2-) to give rise to anionic allyls.However, when the cation is reducible, as on the Fe3+ centers of magnesium ferrite, the allyl anion is further rapidly oxidized to allyloxy species that, at high temperature, can act as cationic allyls which interact weakly with oxide anions.From propene, the cationic allyls can act as symmetric species, as is expected for acrolein synthesis.
The remarkable promotion of in situ formed Pt-cobalt oxide interfacial sites on the carbonyl reduction to allylic alcohols
Li, Chenyue,Ke, Changxuan,Han, Ruirui,Fan, Guoli,Yang, Lan,Li, Feng
, p. 78 - 87 (2018)
Pt catalysts attract increasing attention for selectively hydrogenating α,β-unsaturated aldehydes to produce allylic alcohols, thanks to their relatively satisfactory selectivity towards the reduction of C[dbnd]O bond over C[dbnd]C bond. Here, new carbon supported cobalt oxide-decorated platinum nanocatalysts for highly selective hydrogenation of cinnamaldehyde were fabricated via a facile composite precursor route. As-fabricated cobalt oxide-decorated Pt catalyst at a Co/Pt atomic ratio of 0.6 was found to exhibit an exceptional catalytic performance with an extremely high 99% yield of cinnamyl alcohol under mild reaction conditions (2 MPa H2 and 80 °C). In contrast to that of the undecorated Pt one, the intrinsic activity of the cobalt oxide-decorated Pt-based one, i.e. the turnover frequency for cinnamaldehyde conversion (4.19 s?1), was significantly increased by 9.5 times. The present catalyst system presents a particularly dramatic enhancement in catalytic performance, in comparison with other Pt-based hydrogenation catalysts previously reported. Such exceptional catalytic efficiency was probably corelated with unique geometric and electronic modifications of Pt particles by CoOx species, thereby giving rise to both the increased exposed active metal surface and the favorable electron-rich state of Pt0 species. Correspondingly, the rate of cinnamaldehyde conversion could be improved and the adsorption of the carbonyl group could be strengthened. This synergy between CoOx species and Pt sites is accounted for the observed superiority of CoOx-decorated Pt catalyst to Co-free Pt one in selective hydrogenation of carbonyl compounds.
DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES III-DECOMPOSITION DU PEROXYDE D'ALLYLE ET DE t-BUTYLE DANS LES ETHERS ET LES CYCLANES: EPOXY-2,3 PROPANATION DE CES SOLVANTS
Maillard, B.,Montaudon, E.,Rakotomanana, F.,Bourgeois, M. J.
, p. 5039 - 5044 (1985)
Product analysis of the thermolysis of allyl t-butyl peroxide in cyclohexane and tetrahydrofuran shows that an important induced decomposition of the peroxide occurs by the addition of radicals derived from the solvent, to the peroxide double bond, followed by an intramolecular homolytic displacement of the t-butoxyl group.Such a reaction is a 2,3-epoxypropanation of the solvent in which the initiator is decomposed.The reaction is shown to be general, by using other ethers and cycloalkanes as solvents.
EFFECT OF THE STRUCTURE OF SUBSTITUTED PROPARGYL AND ALLYL ALCOHOLS ON THE RATE OF THEIR LIQUID PHASE HYDROGENATION ON A Pd-Ru ALLOY MEMBRANE CATALYST
Karavanov, A. N.,Gryaznov, V. M.
, p. 1593 - 1596 (1989)
The rates of hydrogenation of substituted propargyl and allyl alcohols in the liquid phase on a Pd-Ru alloy membrane catalyst are described by a two-parameter Taft equation which takes into account the inductive and steric effects of the substituents.The values of the parameters at 363 K with H2 at atmospheric pressure are: ρ* = -0.20, δ = 0.10 and ρ+ = -1.1, δ = 1.3 respectively.
Co-metathesis of ethylene and olefinic compounds in ionic liquids
Greish, Alexander A.,Kustov, Leonid M.,Vasnev, Alexander V.
, p. 329 - 330 (2011)
Tungsten(VI) chloride dissolved in the ionic liquids is capable of catalyzing metathesis of 4-octene and co-metathesis of 4-penten-1-ol with ethylene; the latter reaction is preceded by double bond shift in the starting alkenol.
The decomposition of aliphatic N-nitro amines in aqueous sulfuric acid. Bisulfate as a nucleophile
Cox, Robin A.
, p. 1774 - 1778 (1996)
In aqueous sulfuric acid, aliphatic N-nitro amines decompose to N2O and alcohols. An excess acidity analysis of the observed rate constants for the reaction shows that free carbocations are not formed. The reaction is an acid-catalyzed SN2 displacement from the protonated aci-nitro tautomer, the nucleophile being a water molecule at acidities below 82-85% H2SO4, and a bisulfate ion at higher acidities. Bisulfate is the poorer nucleophile by a factor of about 1000. Twelve compounds were studied, of which results obtained for nine at several different temperatures enabled calculation of activation parameters for both nucleophiles. The reaction appears to be mainly enthalpy controlled. The intercept standard-state rate constants are well correlated by the σ* values for the alkyl groups; the slopes are negative, with a more negative value for the slower bisulfate reaction. Interestingly the m?m* slopes also correlate with σ*, although the scatter is bad.
Selective hydrogenation of the C=O bond in acrolein through the architecture of bimetallic surface structures
Murillo, Luis E.,Goda, Amit M.,Chen, Jingguang G.
, p. 7101 - 7105 (2007)
In the current study we have performed experimental studies and density functional theory (DFT) modeling to investigate the selective hydrogenation of the C=O bond in acrolein on two bimetallic surface structures, the subsurface Pt-Ni-Pt(111) and surface Ni-Pt-Pt(111). We have observed for the first time the production of the desirable unsaturated alcohol (2-propenol) on Pt-Ni-Pt(111) under ultra-high vacuum conditions. Furthermore, our DFT modeling revealed a general trend in the binding energy and bonding configuration of acrolein with the surface d-band center of Pt-Ni-Pt(111), Ni-Pt-Pt(111), and Pt(111), suggesting the possibility of using the value of the surface d-band center as a parameter to predict other bimetallic surfaces for the selective hydrogenation of acrolein.
Synthesis of allyl alcohol as a method to valorise glycerol from the biodiesel production
Wormann, Michael,Maier, Martin E.
, p. 15314 - 15317 (2019)
Reaction of triglycerides with trimethyl orthoformate in presence of camphorsulfonic acid (CSA) gave the fatty acid methyl esters (FAMEs, 4) in good yield. However, under these conditions, the protected glycerol could not be obtained. Formation of orthoesters 9 was possible in a separate reaction using very weak acidic conditions, namely catalytic amounts of pyridinium para-toluenesulfonate (PPTS). Subjecting the orthoesters 9 to thermolysis at 270 °C gave allyl alcohol (11) with good efficiency.