123-05-7Relevant academic research and scientific papers
SELECTIVE TRIMERIZATION OF ALIPHATIC ALDEHYDES CATALYZED BY POLYNUCLEAR CARBONYLFERRATES
Ito, Keiji,Kamiyama, Nobuhiro,Nakanishi, Saburo,Otsuji, Yoshio
, p. 657 - 660 (1983)
Aliphatic aldehydes undergo a catalytic trimerization to give 1,3-diol monoesters upon treatment with Fe3(CO)12 in pyridine or with Fe3(CO)12-pyridine N-oxide in benzene.Polynuclear carbonylferrates serve as catalyst for this transformation.
Silica gel-supported TEMPO with adsorbed NOx for selective oxidation of alcohols under mild conditions
Zhang, Hua,Fu, Luoling,Zhong, Hongmin
, p. 1848 - 1854 (2013)
A column padding silica gel was used to support 2,2,6,6- tetramethylpiperdine-1-oxyl (TEMPO) and to adsorb NOx to provide an oxidant system for the selective oxidation of alcohols. A wide range of alcohols were oxidized to the corresponding aldehydes and ketones with high selectivities and conversions using this heterogeneous catalyst under mild conditions.
Vapor-phase aldolization of n-butyraldehyde to 2-ethyl-2-hexenal over solid-base catalysts
Zhu, Wei-De,Ko, An-Nan
, p. 1237 - 1242 (2000)
Vapor-phase aldol condensation of n-butyraldehyde to 2-ethyl-2-hexenal was studied at 1 atm and 150～ 300°C in a fixed-bed, integral-flow reactor by using NaX, KX, γ-Al2O3 and Na/NaOH/γ-Al2O3 catalysts. Ion exchange of NaX zeolite with potassium acetate solution results in a decrease of crystallinity and apparent lowering of surface area, whereas the basic strength is enhanced. Treatment of γ-Al2O3 with NaOH and Na causes a large decrease of the surface area but strong enhancement of the catalyst basicity. The catalytic activity on the basis of unit surface area is in the order Na/NaOH/γ-Al2O3 > KXU > KXW > NaX>γ-Al2O3, in accordance with the relative catalyst basic strength. The molar ratio of trimeric to dimeric products increases with increasing the reaction temperature and the catalyst basic strength except for Na/NaOH/γ-Al2O3. Very high selectivity of 2-ethyl-2-hexenal (>98.5%) was observed for reactions over NaX zeolite at 150°C. Based on the FT-IR and the catalytic results, the reaction paths are proposed as follows: self-aldol condensation of n-butyraldehyde, followed by dehydration produces 2-ethyl-2-hexenal, which then reacts with n-butyraldehyde and successively dehydrates to 2,4-diethyl-2,4-octadienal and 1,3,5-triethylbenzene. For the reaction over NaX, the calculated Arrhenius frequency factor and activation energy are 314 mol/g-h and 32.6 kJ/mol, respectively.
Iron/ABNO-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones under Ambient Atmosphere
Wang, Lianyue,Shang, SenSen,Li, Guosong,Ren, Lanhui,Lv, Ying,Gao, Shuang
, p. 2189 - 2193 (2016)
We report a new Fe(NO3)3·9H2O/9-azabicyclo[3.3.1]nonan-N-oxyl catalyst system that enables efficient aerobic oxidation of a broad range of primary and secondary alcohols to the corresponding aldehydes and ketones at room temperature with ambient air as the oxidant. The catalyst system exhibits excellent activity and selectivity for primary aliphatic alcohol oxidation. This procedure can also be scaled up. Kinetic analysis demonstrates that C-H bond cleavage is the rate-determining step and that cationic species are involved in the reaction.
One-pot synthesis of C8 aldehydes/alcohols from propylene using eco-friendly hydrotalcite supported HRhCO(PPh3)3 catalyst
Sharma, Sumeet K.,Srivastava, Vivek K.,Shukla, Ram S.,Parikh, Parimal A.,Jasra, Raksh V.
, p. 277 - 286 (2007)
A multi-functional catalyst [HF/HT] containing a rhodium complex, HRh(CO)(PPh3)3 [HF] and a solid base, hydrotalcite Mg 1-xAlx(OH2)x+(CO 32-)x/n·mH2O [HT], synthesized by impregnation of [HF] onto the surface of [HT], was investigated for the one-pot synthesis of C8 aldol derivatives (aldehydes or alcohols) from propylene. The catalyst was found to be efficient to carry out hydroformylation, aldol condensation and hydrogenation reactions in one pot. The catalytic activity of [HF/HT(X)] was studied in detail as functions of Mg/Al molar ratio (X) of [HT], amount of [HF] complex and [HT], and reaction temperature. The selectivity for 2-ethylhexanal was observed to increase upon increasing X and amount of [HT]. The highest selectivity for 2-ethylhexanol was observed for [HT] Mg/Al molar ratio of 3.5 at 250°C. The kinetic profiles of the various products obtained were in agreement with the reaction pathway proposed to understand the role of the [HF/HT] catalyst on the formation of C8 aldol derivatives. Thermal stability of the [HF/HT] catalyst system was also investigated. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
Enamines from terminal epoxides and hindered lithium amides
Hodgson, David M.,Bray, Christopher D.,Kindon, Nicholas D.
, p. 6870 - 6871 (2004)
A new reactivity mode of lithium amides with epoxides leads to hindered enamines. The reaction of some of these enamines with unactivated primary and secondary alkyl halides is described, which expands the range of electrophiles that one can use in the synthesis of mono-alkylated aldehydes. Copyright
Practical and versatile oxidation of alcohol using novel Na2WO4-H2O2 system under neutral conditions
Hida, Takemasa,Nogusa, Hideo
, p. 270 - 274 (2009)
This paper presents a novel Na2WO4-H2O2 oxidation system. The oxidation of alcohol to ketone or aldehyde was carried out by using N,N-dimethylacetamide, hydrogen peroxide, and a catalytic amount of disodium tungstate dihydrate under neutral conditions. This method is very simple, practical for large-scale manufacturing, and applicable to a variety of substrates including an acid-sensitive substrate. Disodium tetraperoxotungstate dihydrate (Na2[W(O2)4]·2H2O) was isolated from a mixture of N,N-dimethylacetamide, hydrogen peroxide, and disodium tungstate dihydrate, and a proposal reaction mechanism is discussed in this paper.
Continuous catalytic "one-pot" multi-step synthesis of 2-ethylhexanal from crotonaldehyde
Seki, Tsunetake,Grunwaldt, Jan-Dierk,Baiker, Alfons
, p. 3562 - 3564 (2007)
2-Ethylhexanal is synthesized directly from crotonaldehyde over a bifunctional acidic resin-supported palladium catalyst via hydrogenation and aldol condensation in supercritical CO2. The Royal Society of Chemistry.
Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence
Harvey, Benjamin G.,Meylemans, Heather A.,Quintana, Roxanne L.
, p. 2450 - 2456 (2012)
An efficient method for the formal anti-Markovnikov hydration of 1,1-disubstituted alkenes has been developed. The utility of the process has been demonstrated by conversion of bio-derived butene oligomers into primary alcohols through initial oxidation to vicinal acetoxy-alcohols, diols, or diacetates, followed by selective dehydration/tautomerization of the diols, and hydrogenation of the intermediary aldehydes. This approach allows for the isolation of important industrial plasticizer alcohols from a renewable source. In a broader context, this pathway, which can be conducted with sustainable, conventional reagents under mild conditions, represents a unique alternative to hydroboration for a challenging subset of hindered olefins.
4-OH-TEMPO/TCQ/TBN/HCl: A Metal-Free Catalytic System for Aerobic Oxidation of Alcohols under Mild Conditions
Dong, Yanli,Zhao, Xiaomei,Liu, Renhua
, p. 1019 - 1023 (2015)
A green and economical catalyst system, 4-OH-TEMPO/TCQ/TBN/HCl, for the aerobic oxidation of a broad range of primary and secondary alcohols to the corresponding carbonyl compounds has been developed. These reactions proceed without transition-metals under mild conditions with excellent yields. A green and economical catalyst system, 4-OH-TEMPO/TCQ/TBN/HCl, for the aerobic oxidation of a broad range of primary and secondary alcohols to the corresponding carbonyl compounds has been developed. These reactions proceed without transition-metals under mild conditions with excellent yields.
