cas 637-78-5, ISOPROPYL PROPIONATE | Articles data

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USE OF ALCOHOLS AS SOURCES OF HYDROGEN IN THE TRANSFORMATION OF CO-OLEFIN MIXTURES
A study has been made of the catalytic activities of various ruthenium complexes in the synthesis of ketones from olefin-carbon monoxide mixtures and an alcohol as source of hydrogen: major side products were shown to be the alkyl propionates and ethane.The effects of base, concentration of catalyst (for RuCl3- and Ru3(CO)12-based systems), pressure, temperature, CO/olefin ratio and the water content of the alcohol have been examined.
Isnard, P.,Denise, B.,Sneeden, R.P.A.,Cognion, J.M.,Durual, P.
p. 169 - 178
(1982)
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Manganese-Mediated C-C Bond Formation: Alkoxycarbonylation of Organoboranes
Alkoxycarbonylations are important and versatile reactions that result in the formation of a new C-C bond. Herein, we report on a new and halide-free alkoxycarbonylation reaction that does not require the application of an external carbon monoxide atmosphere. Instead, manganese carbonyl complexes and organo(alkoxy)borate salts react to form an ester product containing the target C-C bond. The required organo(alkoxy)borate salts are conveniently generated from the stoichiometric reaction of an organoborane and an alkoxide salt and can be telescoped without purification. The protocol leads to the formation of both aromatic and aliphatic esters and gives complete control over the ester's substitution (e.g., OMe, OtBu, OPh). A reaction mechanism was proposed on the basis of stoichiometric reactivity studies, spectroscopy, and DFT calculations. The new chemistry is particularly relevant for the field of Mn(I) catalysis and clearly points to a potential pathway toward irreversible catalyst deactivation.
Van Putten, Robbert,Filonenko, Georgy A.,Krieger, Annika M.,Lutz, Martin,Pidko, Evgeny A.
supporting information
p. 674 - 681
(2021/04/02)

Method for preparing propionate by ester alcohol exchange
The invention discloses a method for preparing propionate by ester alcohol exchange, and relates to a method for preparing propionate. According to the invention, the method for synthesizing propionate by ester alcohol exchange of methyl propionate and various alcohols (including monohydric alcohols such as ethanol, propanol, butanol, tert-butanol, isopropanol, cyclohexanol, allyl alcohol and thelike, dihydric alcohols such as 1,3-propylene glycol and the like, glycerol and the like) is adopted, and methyl propionate and the alcohols are used as raw materials to carry out a reaction under catalysis of alkaline ionic liquid, soluble strong alkali or solid alkali to prepare higher propionate and methanol. According to the method, the synthetic route is short, and the reaction product is taken out through azeotropic extraction of the methyl propionate and methanol, so that the reaction is more thorough, and the target product is directly obtained by one step. The product obtained by thereaction only contains propionate and methanol, the whole reaction process is concise and efficient and is free of pollution, no byproducts are generated, and great significance is achieved for large-scale and low-cost production of propionate.
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Paragraph 0038-0039

(2019/07/04)

Hydrogenation of Ketones and Esters Catalyzed by Pd/C?SiO2
Hydrogenation of unsaturated ketones and esters with molecular hydrogen on the 5%Pd/C?SiO2 heterogeneous catalyst has been studied. The reaction direction and yield are determined by the starting compounds structure. Hydrogenation of unsaturated ketones containing phenyl group at the double carbon–carbon atom is accompanied by the reduction of the ketone group into the alcohol one. Hydrogenation of unsaturated esters is accompanied by transesterification.
Akchurin,Baibulatov,Dokichev
p. 195 - 198
(2018/03/26)

Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions
In this work, a new Fe3O4/AlFe/Te nanocomposite was synthesized by a one-step sol–gel method. The Fe3O4 magnetic nanoparticles (MNPs) were prepared and then mixed with aluminum telluride (Al2Te3) in an alkali medium to produce the desired catalyst. After characterization of the Fe3O4/AlFe/Te nanocomposite by SEM, TEM, EDS, XRD, and ICP analyses, it was used in the esterification reaction. This heterogeneous catalyst showed high catalytic activity in the esterification of commercially available carboxylic acids with various alcohols to produce the desired esters at high conversions under neat conditions. The Fe3O4/AlFe/Te nanocomposites were separated from the reaction mixture via an external magnet and re-used 8 times without significant loss of catalytic activity.
Alavi, Seyed Jamal,Sadeghian, Hamid,Seyedi, Seyed Mohammad,Eshghi, Hossein,Salimi, Alireza
(2017/11/23)

Selective Hydrodeoxygenation of Alkyl Lactates to Alkyl Propionates with Fe-based Bimetallic Supported Catalysts
Hydrodeoxygenation (HDO) of methyl lactate (ML) to methyl propionate (MP) was performed with various base-metal supported catalysts. A high yield of 77 % MP was obtained with bimetallic Fe–Ni/ZrO2 in methanol at 220 °C and 50 bar H2. A synergistic effect of Ni increased the yield of MP significantly when using Fe–Ni/ZrO2 instead of Fe/ZrO2 alone. Moreover, the ZrO2 support contributed to improve the yield as a phase transition of ZrO2 from tetragonal to monoclinic occurred after metal doping giving rise to fine dispersion of the Fe and Ni on the ZrO2, resulting in a higher catalytic activity of the material. Interestingly, it was observed that Fe–Ni/ZrO2 also effectively catalyzed methanol reforming to produce H2 in situ, followed by HDO of ML, yielding 60 % MP at 220 °C with 50 bar N2 instead of H2. Fe–Ni/ZrO2 also catalyzed HDO of other short-chain alkyl lactates to the corresponding alkyl propionates in high yields around 70 %. No loss of activity of Fe–Ni/ZrO2 occurred in five consecutive reaction runs demonstrating the high durability of the catalyst system.
Khokarale, Santosh Govind,He, Jian,Schill, Leonhard,Yang, Song,Riisager, Anders,Saravanamurugan, Shunmugavel
p. 681 - 687
(2018/02/13)

Efficient Palladium-Catalyzed Alkoxycarbonylation of Bulk Industrial Olefins Using Ferrocenyl Phosphine Ligands
The development of ligands plays a key role and provides important innovations in homogeneous catalysis. In this context, we report a novel class of ferrocenyl phosphines for the alkoxycarbonylation of industrially important alkenes. A basic feature of our ligands is the combination of sterically hindered and amphoteric moieties on the P atoms, which leads to improved activity and productivity for alkoxycarbonylation reactions compared to the current industrial state-of-the-art ligand 1,2-bis((di-tert-butylphosphino)methyl)benzene). Advantageously, palladium catalysts with these novel ligands also enable such transformations without additional acid under milder reaction conditions. The practicability of the optimized ligand was demonstrated by preparation on >10 g scale and its use in palladium-catalyzed carbonylations on kilogram scale.
Dong, Kaiwu,Sang, Rui,Fang, Xianjie,Franke, Robert,Spannenberg, Anke,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias
supporting information
p. 5267 - 5271
(2017/04/27)

PROCESS FOR HYDROGENOLYSIS OF ALPHA-HYDROXY ESTERS OR ACIDS USING A HETEROGENEOUS CATALYST
The present invention relates to a method for hydrogenolysis of alpha-hydroxy esters or acids, comprising reacting the alpha-hydroxy ester or acid in the presence of a heterogeneous catalyst. The present invention also relates to a method for producing propionic acid ester, and the use of any of the methods for the production of propionic acid esters, such as alkyl propionate.
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Page/Page column 26

(2017/01/31)

An extremely efficient and green method for the acylation of secondary alcohols, phenols and naphthols with a deep eutectic solvent as the catalyst
The typical deep eutectic solvent [CholineCl][ZnCl2]3, easily prepared from choline chloride and zinc chloride, is green and useful for the acylation of secondary alcohols, phenols, and naphthols with acid anhydrides. Its efficiency allows the acylation of sterically hindered secondary alcohols and acid anhydrides to proceed in high yield under mild condition. The catalyst is cheap, easy to handle, conveniently synthesized in a single step, and recyclable for several times without significant loss of catalytic activity.
Nguyen, Hai Truong,Tran, Phuong Hoang
p. 98365 - 98368
(2016/10/31)

Exceptional activity of gallium(III) chloride and chlorogallate(III) ionic liquids for Baeyer–Villiger oxidation
Baeyer–Villiger oxidation of cyclic ketones, using H2O2 as the oxidising agent, was systematically studied using a range of metal chlorides in different solvents, and in neat chlorogallate(III) ionic liquids. The extremely high activity of GaCl3 in promoting oxidation with H2O2, irrespective of solvent, was reported for the first time. The activity of all other metal chlorides was strongly solvent-dependent. In particular, AlCl3 was very active in a protic solvent (ethanol), and tin chlorides, SnCl4 and SnCl2, were active in aprotic solvents (toluene and dioxane). In order to eliminate the need for volatile organic solvent, a Lewis acidic chlorogallate(III) ionic liquid was used in the place of GaCl3, which afforded typically 89–94% yields of lactones in 1–120 min, at ambient conditions. Raman and 71Ga NMR spectroscopic studies suggest that the active species, in both GaCl3 and chlorogallate(III) ionic liquid systems, are chlorohydroxygallate(III) anions, [GaCl3OH], which are the products of partial hydrolysis of GaCl3 and chlorogallate(III) anions; therefore, the presence of water is crucial.
Markiton, Magdalena,Chrobok, Anna,Matuszek, Karolina,Seddon, Kenneth R.,Swadzba-Kwasny, Ma?gorzata
p. 30460 - 30467
(2019/01/14)

A fructose-based biomass catalytic conversion systems furan derivatives
A method for preparing furan derivatives by catalytic conversion of fructose-based biomass is characterized by: taking biomass such as fructose, cane sugar, inulin and the like as raw materials, taking low-boiling-point alcohols comprising aliphatic alcohols or alicyclic alcohols all with six or less than six carbon atoms as a solvent, and under the effect of a catalyst, performing reactions comprising hydrolysis, dehydration, etherfication and the like for coupling so as to obtain furan derivatives such as 5-alkoxymethyl furfural, levulinate esters, 5-hydroxymethylfurfural and the like. The method has the advantages of high raw material utilization rate, high in-situ coupling efficiency in the dehydration and etherfication reactions, and easily separated and purified system.
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Paragraph 0022

(2017/02/09)

Transfer Hydrogenation of Nitriles, Olefins, and N-Heterocycles Catalyzed by an N-Heterocyclic Carbene-Supported Half-Sandwich Complex of Ruthenium
In the presence of KOBut, N-heterocyclic carbene-supported half-sandwich complex [Cp(IPr)Ru(pyr)2][PF6] (3) (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) catalyzes transfer hydrogenation (TH) of nitriles, activated N-heterocycles, olefins, and conjugated olefins in isopropanol at the catalyst loading of 0.5%. The TH of nitriles leads to imines, produced as a result of coupling of the initially formed amines with acetone (produced from isopropanol), and showed good chemoselectivity. Reduction of N-heterocycles occurs for activated polycyclic substrates (e.g., quinoline) and takes place exclusively in the heterocycle. The TH also works well for linear and cyclic olefins but fails for trisubstituted substrates. However, the C = C bond of α,β-unsaturated esters, amides, and acids is easily reduced even for trisubstituted species, such as isovaleriates. Mechanistic studies suggest that the active species in these catalytic reactions is the trihydride Cp(IPr)RuH3 (5), which can catalyze these reactions in the absence of any base. Kinetic studies are consistent with a classical inner sphere hydride-based mechanism of TH.
Mai, Van Hung,Nikonov, Georgii I.
p. 943 - 949
(2016/05/09)

Process for the preparation of propionic acid methyl ester
The invention relates to a preparation method of propionate, belonging to the technical field of preparation of organic substances. Propanoic acid and monobasic alcohol are subjected to esterification reaction under the action of a gel-type strong-acid ion exchange resin catalyst to generate the propionate. The gel-type strong-acid ion exchange resin is a hydrogen-type styrene-stilbene copolymer with sulfonate group, and the pore size of the resin is less than 8nm. The preparation method provided by the invention uses the catalyst to effectively adsorb the reaction impurities and enhance the product purity; and the catalyst has the advantages of favorable catalytic effect and low corrosivity, and can be easily separated from the product.
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Paragraph 0064; 0065; 0066; 0067j; 0068; 0069

(2016/12/22)

Continuous flow Fischer esterifications harnessing vibrational-coupled thin film fluidics
Rapid Fischer esterification reactions occur under solventless, continuous flow conditions in dynamic thin films. This methodology uses limited catalyst, require no additional heat input and occurs within the confinements of an inexpensive vortex fluidic device (VFD). The associated mechanoenergy is primarily delivered from two types of vibration, which are manifested in sharp increases in the yield of the reactions. These vibrations promote the existence of Faraday waves that alter the instantaneous shear rates of the reactants within the rotating tube. Tuning the rotational speed of the device allows harmonic vibrations to be utilized in the synthesis of alkyl-based esters within both a high and low contact angle NMR tube. This journal is
Britton, Joshua,Dalziel, Stuart B.,Raston, Colin L.
p. 1655 - 1660
(2015/02/02)

Comparison of the performance of commercial immobilized lipases in the synthesis of different flavor esters
In this work, it is compared the performance of three commercial lipase preparations (Novozym 435, Lipozyme TL-IM, and Lipozyme RM-IM) in the synthesis of flavor esters obtained by esterification of acetic, propionic, and butyric acids using ethanol, isopropyl alcohol, butanol, or pentanol. A comprehensive comparison was performed verifying activities of these three enzyme preparations versus the different couples of substrates, checking the obtained yields. In general, the longer the acid chain, the higher the reaction yields. Novozym 435 was the most efficient enzyme in most cases, and only Lipozyme RM-IM offered better results than Novozym 435 in the production of ethyl butyrate. Reactions with butyric acid showed the highest conversion rates using all biocatalysts. Using optimal substrates, the reactions catalyzed by the three enzymes were optimized using the response surface methodology, and the catalytic performance of the biocatalysts in repeated batches was assessed. After optimization, yields higher than 90% were obtained for all three enzymes, but Lipozyme TL-IM needed four-times more biocatalyst content than the other two preparations. Novozym 435 kept over 80% of its activity when reused in 9 successive batches, whereas Lipozyme RM-IM can be reused 5 times and Lipozyme TL-IM only 3 times. In general, Novozym 435 showed to be more suitable for these reactions than the other two enzyme preparations.
Martins, Andrea B.,Da Silva, Alexandre M.,Schein, Mirela F.,Garcia-Galan, Cristina,Zachia Ayub, Marco A.,Fernandez-Lafuente, Roberto,Rodrigues, Rafael C.
p. 18 - 25
(2014/05/06)

Determination of steric effect on the esterification of different alcohols with propanoic acid over cation-exchange resin catalyst Dowex 50Wx4
This paper describes the application of LFER in the form of Taft correlation to understand the mechanism of the esterification of propanoic acid with different alcohols over heterogeneous catalyst, Dowex 50Wx4. The rate constant (k1) in the rate equation decreases with change of alcohols in the order methanol, ethanol, n-propyl, n-butyl, n-pentyl, iso-butyl, iso-propyl and sec-butyl (2-buthanol). The reaction of propanoic acid with alcohols fits the Taft equation, log k1.kCH3 = 1.0061 Es K 0.0012, which implies that the steric effect of the substituent governs that reaction and the mechanism is similar between the different alcohols. The experimental results were modelled according to a simple second-order model. It was found that the equilibrium constant of this reaction does not depend on the structure of the organic alcohols, and has for 333 K the value 4.04. by Oldenbourg Wissenschaftsverlag, Munchen.
Erdem, Beyhan,Cebe, Mustafa
experimental part
p. 125 - 136
(2011/04/24)

Molecular iodine in ionic liquid: A green catalytic system for esterification and transesterification
Esterification of carboxylic acids and transesterification of-ketoesters with alcohols have been developed using a catalytic amount of iodine in polyethylene glycol (PEG) ionic liquid (IL 1000) to afford the corresponding esters in good yields. By simple separation of the ionic-liquid phase containing the iodine, the system of I2/IL 1000 can be reused several times. Copyright
Ren, Yiming,Cai, Chun
scheme or table
p. 1670 - 1676
(2010/08/03)

PRODUCTION OF ESTERS
This invention relates to a process for the hydroesterification of olefins in which a hydrocarbon stream containing olefins is reacted with CO and an alcohol in the presence of a catalyst to form a hydrocarbon stream containing esters, wherein the alcohol has more than one carbon atom. The hydroesterification reaction is typically carried out in the presence of a catalyst comprising cobalt and a nitrogen-containing additive such as pyridine and the olefins may be branched. The invention also relates to a process for preparing an alkoxylated ester suitable for use as a surfactant molecule in detergent formulations.
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Page/Page column 22

(2008/06/13)

Polymer-supported ytterbium perfluorooctanesulfonate [Yb(OPf)3]: A recyclable catalyst for organic reactions
Amberlyst A-21, a kind of well-known and cheap polymeric material, was treated with ytterbium perfluorooctanesulfonate [Yb(OPf)3] giving a reagent with a ytterbium loading of 1.34 (wt%). The polymer-supported fluorous ytterbium catalyses the highly efficient nitration, esterification, Fridel-Crafts acylation, and aldol condensation. The catalyst can be recovered by simple filtration and used again without a significant loss of catalytic activity. The protocol avoids the use of fluorous solvents during the reaction or workup, which are expensive and can leach in small amounts.
Yi, Wen-Bin,Cai, Chun
p. 524 - 528
(2008/12/22)

Solid acids in liquid phase esterification
Catalytic activity of different protonated zeolites such as HY, Hβ, HZSM5 and sulfated oxides such as SO42-/Al 2O3, SO42-/SiO2, SO 42-/ZrO2 in the esterification of propionic acid with various alcohols (C1-C5) over solid acids as catalysts has been investigated. The catalysts have been characterized for their total surface acidity, BET surface area and sulfur content in sulfated catalysts. Catalytic activity studies have been conducted in liquid phase under refluxing conditions. A systematic study has been made to find out the effects of nature of alcohols, amount of the catalyst and the duration of reaction in the synthesis of propionate esters. Product analysis has been done quantitatively by gas chromatography and qualitatively by GC-MS. All the catalysts have been found to be active towards the formation of propionate esters as the major reaction product. A good correlation between the concentration of acid sites and the catalytic activity of the catalysts has been observed.
Nagaraju,Mohamed Shamshuddin
p. 1165 - 1170
(2007/10/03)

Novel desilylation of alpha-dimethylsilyl esters by electrochemically generated superoxide ion
Electrochemical reduction of oxygen in the presence of an alpha-dimethylsilyl ester results in removal of the dimethylsilyl group. The reaction presumably proceeds by a mechanism involving electrochemically-generated superoxide ion.
Kaimakliotis, Christos,Fry, Albert J.
p. 5859 - 5861
(2007/10/03)

Dioxomolybdenum(VI) complexes as catalytic neutral esterification agents
Esterification reactions of carboxylic acids with different alcohols in neutral nonaqueous media have been carried out in excellent yields using catalytic amounts of dioxomolybdenum(VI) complexes of the type [MoO2L2] (where LH = acetylacetone, salicylaldehyde, o-aminophenol, 8-hydroxyquinoline, and 2-acetyl pyridoxime). The reactions of propionic acid with primary, secondary and tertiary alcohols in the presence of catalytic amounts of MoO2(acac)2 result in higher yields of the esters with primary alcohols, compared to those with secondary or tertiary alcohols. The results of the esterification reactions of propionic acid with methanol and tertiary butanol in the presence of different dioxomolybdenum(VI) complexes suggest that the homogeneous catalysts are better than heterogeneous analogues.
Nag, Purnima,Bohra, Rakesh,Mehrotra, Ram C.
p. 86 - 88
(2007/10/03)

Structure-function correlation in lipase catalysed esterification reactions of short and medium carbon chain length alcohols and acids
An attempt has been made to correlate the carbon chain lengths of acids and alcohols to the extent of esterification in the Rhizomucor miehei lipase catalyzed esterification reactions involving acids of carbon chain length C2-C5 and alcohols of carbon chain length C1-C8.
Divakar, Soundar
p. 1919 - 1922
(2007/10/03)

Zinc promoted mild and efficient method for the esterification of acid chlorides with alcohols
The esterification of variety of acid chlorides with alcohols in the presence of zinc is described. The easy formation of t-butyl and pivaloyl esters are the additional importance of this procedure.
Yadav,Reddy, Gondi Sudershan,Srinivas, Dale,Himabindu, Konuru
p. 2337 - 2342
(2007/10/03)

A new simplified method for esterification of secondary and tertiary alcohols
Esters of secondary and tertiary alcohols have been synthetized in the absence of solvent and catalyst and only under the effect of temperature with high yields.
Kammoun,Le Bigot,Delmas,Boutevin
p. 2777 - 2781
(2007/10/03)

Kinetics of Catalysed Esterification of Propionic Acid with various Alcohols using Synthetic Cation Exchange Resin
Kinetics of esterification of ethyl, 2-propyl and 1-butyl alcohols with propionic acid have been investigated using SBPF (styrene-butadiene-phenolformaldehyde) synthetic cation exchange resin (in H+- form). The experimental data are found to fit a second order bimolecular kinetic equation. The influence of molecular weight, structure of alcohols, amount of catalyst (H+-ion), molar raito of reactants and reaction temperature on the specific rate constant and percent conversion have been investigated. The esterification reaction rate constant (K1) and the percent conversion (XAe, %) for different alcohols with propionic acid have been calculated and compared. It is found to decrease with increasing molecular weight and branching of alcohols : 2-propanol 1-butanol ethanol.
Awad,Salem,Swelam
p. 467 - 469
(2007/10/03)

Oxygen Atom Transfer With Niobocene Ketenes; Baeyer-Villiger Chemistry with Unusual Regioselectivities
Niobocene ketene complex 1 has been utilized as an oxygen atom transfer reagent, converting ketones and aldehydes to esters and carboxylic acids.The steric properties of compound 1 give rise to a series of relative migratory aptitudes that differs from those seen for peracids.The process may be rendered catalytic in 1 with methyltrifluoromethyldioxirane (4). Key Words: Baeyer-Villiger reaction, niobocene complexes, ketenes, oxygen transfer, dioxiranes
Fermin, Maria C.,Bruno, Joseph W.
p. 7545 - 7548
(2007/10/02)

Synthesis of 1,4-Keto Esters and 1,4-Diketones via Palladium-Catalyzed Acylation of Siloxycyclopropanes. Synthetic and Mechanistic Studies
The reaction of a variety of siloxycyclopropanes with acid chlorides in the presence of a catalytic amount of a palladium/phosphine complex gives 1,4-dicarbonyl compounds to good yield. 1-Alkoxy-1-(trialkylsiloxy)-cyclopropanes react with both aromatic and aliphatic acid chlorides in chloroform to give 1,4-keto esters.Synthesis of 1,4-diketones by the acylation of 1-alkyl- or 1-aryl-1-siloxycyclopropanes has been achieved by carrying out the reaction if HMPA under 10-20 atm of carbon monoxide.Kinetic studies and product analysis revealed the unique mechanism of this reaction, which involves rate-determining cleavage of the strained cyclopropane carbon-carbon bond with a coordinatively unsaturated acylpalladium chloride complex.Ab initio calculations of hydroxylated cyclopropane model compounds showed that the unique reactivities of the siloxycyclopropanes may be correlated with the molecular orbital properties of these compounds rather than their ground-state structural properties.
Fujimura, Tsutomu,Aoki, Satoshi,Nakamura, Eiichi
p. 2809 - 2821
(2007/10/02)

An Unexpected Outcome of the Reaction between β-Lactones and Dissolved Potassium
An unexpected novel reaction between β-propiolactones and a solution of potassium containing 18-crown-6, involving C-C bond scission in the β-lactone ring, provides a convenient route to enolate anions.
Jedlinski, Zbigniew,Kowalczuk, Marek,Misiolek, Andrzej
p. 1261 - 1262
(2007/10/02)

SYNTHESIS OF 4-KETO PIMELATES BY PALLADIUM-CATALYZED CARBONYLATIVE SYMMETRICAL COUPLING OF SILOXYCYCLOPROPANES
Treatment of 1-alkoxy-1-siloxycyclopropane with a catalytic amount of a palladium/phosphine complex in chloroform under carbon monoxide atmosphere gives 4-keto pimelate.
Aoki, Satoshi,Nakamura, Eiichi,Kuwajima, Isao
p. 1541 - 1542
(2007/10/02)