cas 141-28-6, Diethyl adipate | Articles data

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Oxovanadium(V)-Induced Ring-Opening Oxygenation of Cyclic Ketones in Alcohol
Cyclic ketones underwent ring-opening oxygenation on treatment with VO(OEt)Cl2 in alcohol under oxygen to give the corresponding keto ester or diesters depending on the substituent at 2-position.This system was applicable to a catalytic reaction.
Hirao, Toshikazu,Mori, Makoto,Ohshiro, Yoshiki
p. 2399 - 2400
(1989)
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Facile esterification of sulfonic acids and carboxylic acids with triethylorthoacetate
Triethylorthoacetate was found to be surprisingly more effective than triethylorthoformate in the esterification of sulfonic acids and carboxylic acids. Using this reagent, esters of sulfonic and carboxylic acids are prepared in high yields.
Trujillo, John I.,Gopalan, Aravamudan S.
p. 7355 - 7358
(1993)
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Microwave-Assisted Nickel-Catalyzed Rapid Reductive Coupling of Ethyl 3-iodopropionate to Adipic Acid
Abstract: 3-iodopropionic acid (3-IPA) can be efficiently synthesized from the glycerol derivative glyceric acid (GA), which is a potential biomaterial-based platform molecule. In this report, ethyl 3-iodopropionate was rapidly dimerized to diethyl adipate in a microwave reactor using NiCl2·6H2O as a catalyst, co-catalyzed by Mn and the 1, 10-Phenanthroline monohydrate ligand. Under the optimum reaction conditions, diethyl adipate can be obtained with 84% yield at 90?°C in just 5?min. Diethyl adipate was hydrolyzed to obtain the adipic acid (AA) in 89% yield with an acid catalyst. AA is an important chemical and a monomer for producing a wide range of high-performance polymeric substances. This rapid coupling method is also applicable to other alkyl halides. Graphic Abstract: [Figure not available: see fulltext.]
Zhang, Linfeng,Zheng, Jing,Zou, Wenya,Shu, Yongqi,Yang, Weiran
p. 2339 - 2345
(2021/01/04)

Biomass-derived dibasic acids to diesters with inorganic ligand-supported catalyst: synthesis, optimization, characterization
Several attempts have been made to obtain aliphatic dicarboxylic diesters from esterification reaction to develop the biomass-derived platform molecules and green manufacturing processes. In this paper, Na3(H2O)6[AlMo6O18(OH)6], an Anderson-type polyoxometalate, firstly, was reported as a catalyst for diester synthesis from dicarboxylic acid to diester which showed an well productivity and selectivity characterized by 1H and 13C. Response surface methodology (RSM) integrated with the desirability function approach was used to determine the best operative conditions, and the optimal reaction parameters for maximum dipropyl succinate yield (77 ± 2.5%) were identified as 1.19?mol.% catalyst loading, 4.9:1 propanol/succinic acid ratio, 113?°C, and 9.6?h. Three batches of tests were carried for catalyst recycling with 78–75% yield even after 6 cycles of esterification. In addition, the substrate carbon chain was increased for investigation of substrate scope achieving satisfactory results and all products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy.
Chen, Zhe,Han, Sheng,Lu, Deli,Xu, Yumeng
(2021/08/23)

Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters
The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.
Yang, Ji,Liu, Jiawang,Ge, Yao,Huang, Weiheng,Ferretti, Francesco,Neumann, Helfried,Jiao, Haijun,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information
p. 9527 - 9533
(2021/03/08)

Preparation method for catalytic synthesis of adipic acid dialkyl ester by heteropolyacid
The invention relates to a preparation method for catalytic synthesis of adipic acid dialkyl ester by heteropolyacid. The method specifically comprises the following steps: 1) mixing adipic acid, alcohol and heteropolyacid, uniformly stirring, and carrying out esterification reaction; and 2) after the esterification reaction is finished, standing and filtering to remove heteropoly acid, adding a sodium carbonate aqueous solution to obtain an organic phase and a water phase, taking the organic phase, concentrating and drying to obtain the product adipic acid dialkyl ester. Compared with the prior art, the raw materials are easy to obtain, the preparation method is simple, the preparation method is economical and environmentally friendly, and the adopted catalyst has the advantages of beinghigh in reaction activity, easy to recycle and the like.
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Paragraph 0040-0041

(2021/01/15)

Compound with fragrance of dried tangerine peel and preparation method thereof, and daily essence
The invention relates to a compound with fragrance of dried tangerine peel and a preparation method thereof, and daily essence. The compound with the fragrance of dried tangerine peel has a structuralformula as described in the specification. The molecular weight of the compound with the fragrance of dried tangerine peel is larger than the molecular weight of a traditional compound with the fragrance of dried tangerine peel, and the compound provided by the invention has better fragrance retention performance and lasting fragrance retention time. Besides, the compound with the fragrance of dried tangerine peel can be used in citrus essence to improve the natural feeling and the heavy feeling of the citrus essence, and the compound has good performance in body fragrance and tail fragranceof the essence.
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Paragraph 0050-0054; 0066-0069; 0072-0075

(2020/06/09)

Method for synthesizing intermediate diethyl adipate
The invention discloses a method for synthesizing an intermediate diethyl adipate. According to the method, adipic acid, ethanol, resin D072, MgO, gamma-glycidyl ether propyl trimethoxysilane, sulfuric acid and hydrochloric acid serve as main raw materials, wherein the raw materials adopted are proportioned as follows: the volume ratio of the adipic acid to the ethanol is 2: 5; and the mass ratioof the MgO to the gamma-glycidyl ether propyl trimethoxysilane is 3: 4. According to the method disclosed by the invention, homemade Mg loaded resin is adopted as a catalyst, and the diethyl adipate is prepared by a reaction rectification coupled process; and the catalyst is moderate in reaction, good in mechanical properties and good in selectivity, is easily separated from a reaction systemand can be reused, so that the method has a relatively good industrial application prospect.
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Paragraph 0007; 0008; 0009-0025

(2019/05/15)

The diamine compound, the resin composition, the resin film, a prepreg, a laminate, a printed wiring board of semiconductor package (by machine translation)
[A] providing a low dielectric constant with a diamine compound, a diamine compound-containing resin composition, further, the resin composition obtained, resin film, prepreg, a laminate, printed circuit board and the semiconductor package. In the general formula (1) diamine compound represented by [a]. (In the general formula (1), R1 - R4 Is, independently, an alkyl group of carbon number 2 or more. R1 - R4 The, each alkyl may be the same as, or different alkyl groups. The n, is an integer of 2 or more. )[Drawing] no (by machine translation)
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Paragraph 0038; 0039

(2019/09/19)

BISMALEIMIDE COMPOUND AND INTERMEDIATE THEREOF, RESIN COMPOSITION, RESIN FILM, PREPREG, LAMINATE, PRINTED WIRING BOARD AND SEMICONDUCTOR PACKAGE
PROBLEM TO BE SOLVED: To provide a bismaleimide compound that achieves lower dielectric constants and an intermediate thereof, a resin composition containing the bismaleimide compound,and a resin film, a prepreg, a laminate, a printed wiring board and a semiconductor package obtained by using the resin composition. SOLUTION: The present invention provides a bismaleimide compound represented by general formula (1) (where R1-R4 independently represent an alkyl group having two or more carbon atoms; each of R1-R4 may represent the same alkyl group or may represent mutually different alkyl groups; n is an integer of 2 or greater). SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0054; 0055

(2019/09/20)

Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes
The direct carbonylation of 1,3-butadiene offers the potential for a more cost-efficient and environmentally benign route to industrially important adipic acid derivatives. However, owing to the complex reaction network of regioisomeric carbonylation and isomerization pathways, a selective practical catalyst for this process has thus far proven elusive. Here, we report the design of a pyridyl-substituted bidentate phosphine ligand (HeMaRaphos) that, upon coordination to palladium, catalyzes adipate diester formation from 1,3-butadiene, carbon monoxide, and butanol with 97% selectivity and 100% atom-economy under industrially viable and scalable conditions (turnover number > 60,000). This catalyst system also affords access to a variety of other di- and triesters from 1,2- and 1,3-dienes.
Yang, Ji,Liu, Jiawang,Neumann, Helfried,Franke, Robert,Jackstell, Ralf,Beller, Matthias
p. 1514 - 1517
(2020/01/08)

Electrochemical cross-coupling of biogenic di-acids for sustainable fuel production
Direct electrocatalytic conversion of bio-derivable acids represents a promising technique for the production of value-added chemicals and tailor-made fuels from lignocellulosic biomass. In the present contribution, we report the electrochemical decarboxylation and cross-coupling of ethyl hydrogen succinate, methyl hydrogen methylsuccinate and methylhexanoic acid with isovaleric acid. The reactions were performed in aqueous solutions or methanol at ambient temperatures, following the principles of green chemistry. High conversions of the starting materials have been obtained with maximum yields between 42 and 61% towards the desired branched alkane products. Besides costly Pt electrodes also (RuxTi1-x)O2 on Ti electrodes exhibited a notable activity for cross-Kolbe electrolysis. As some of the products are insoluble in water, easy product isolation and reuse of the reaction solvent is enabled via phase separation. Several side products have been identified to evaluate the efficiency of the reaction and to elucidate the factors influencing the product selectivity. The yielded alkanes and esters were assessed with regard to their potential as fuels for internal combustion engines. While the longer alkanes constitute promising candidates for the compression-ignition engine, the smaller ester represents an interesting option for the spark-ignition engine.
Holzh?user, F. Joschka,Creusen, Guido,Moos, Gilles,Dahmen, Manuel,K?nig, Andrea,Artz, Jens,Palkovits, Stefan,Palkovits, Regina
p. 2334 - 2344
(2019/05/21)

Assisted Tandem Catalytic Conversion of Acrylates into Adipic Esters
A ruthenium-catalyzed tail-to-tail dimerization of acrylates followed by hydrogenation results in the synthesis of adipic esters in one pot. An imine-ligated ruthenium complex that has good catalytic reactivity for tail-to-tail dimerization of methyl acrylate can be readily converted to a hydrogenation catalyst resulting in the assisted tandem catalytic conversion of methyl acrylate to methyl adipate.
Maity, Pradip K.,Tunge, Jon A.
p. 3419 - 3423
(2018/07/31)

DEOXYDEHYDRATION OF SUGAR DERIVATIVES
The disclosure provides methods for deoxydehydration of sugar-based derivatives using hydrogen gas as a reducing agent.
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(2017/09/09)

Hydrogen Gas-Mediated Deoxydehydration/Hydrogenation of Sugar Acids: Catalytic Conversion of Glucarates to Adipates
The development of a system for the operationally simple, scalable conversion of polyhydroxylated biomass into industrially relevant feedstock chemicals is described. This system includes a bimetallic Pd/Re catalyst in combination with hydrogen gas as a terminal reductant and enables the high-yielding reduction of sugar acids. This procedure has been applied to the synthesis of adipate esters, precursors for the production of Nylon-6,6, in excellent yield from biomass-derived sources.
Larson, Reed T.,Samant, Andrew,Chen, Jianbin,Lee, Woojin,Bohn, Martin A.,Ohlmann, Dominik M.,Zuend, Stephan J.,Toste, F. Dean
supporting information
p. 14001 - 14004
(2017/10/17)

PROCESS FOR DOUBLE CARBONYLATION OF ALLYL ALCOHOLS TO CORRESPONDING DIESTERS
The invention relates to a process for doubly carbonylating allyl alcohols to the corresponding diesters, wherein a linear or branched allyl alcohol is reacted with a linear or branched alkanol (alcohol) with supply of CO and in the presence of a catalytic system composed of a palladium complex and at least one organic phosphorus ligand and in the presence of a hydrogen halide selected from HCl, HBr and HI.
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Paragraph 0055; 0058; 0059

(2017/07/14)

Desymmetrizing Hydroformylation of Dihydromuconic Acid Diesters: Application to the Synthesis of (±)-Vindeburnol
The desymmetrizing hydroformylation of internal alkenes derived from dihydromuconic acid is described. The study of this reaction afforded easy access to polyfunction aldehydes. After the evaluation of the reactivity of the dimethyl ester derivative with various primary amines, this methodology was used to design a rapid synthesis of (±)-vindeburnol from tryptamine in only two steps.
Salacz, Laura,Charpentier, Cyrille,Suffert, Jean,Girard, Nicolas
p. 2257 - 2262
(2017/02/26)

The synthesis of di-carboxylate esters using continuous flow vortex fluidics
A vortex fluidic device (VFD) is effective in mediating the synthesis of di-esters at room temperature. Processing under ambient conditions allows for a simple and efficient synthesis, whilst operating under continuous flow addresses scalability. The rotational speed of the sample tube and the flow rate were critical variables during reaction optimization, and this relates to the behaviour of the fluid flow at a molecular level. Whilst at specific rotational speeds the tube imparts a vibrational response into the fluid flow, the flow rate dictates residence time and the ability to maintain high levels of shear stress. The combination of mechanically induced vibrations, rapid micromixing, high levels of shear stress and water evaporation results in yields up to 90% for 3.25 minutes or less residence time. These results are key for devising greener and more efficient processes both mediated by the VFD and other continuous flow platforms.
Britton, Joshua,Dalziel, Stuart B.,Raston, Colin L.
p. 2193 - 2200
(2016/04/19)

Cobalt-Catalyzed Csp3?Csp3Homocoupling
An efficient and easy method for Csp3?Csp3homocoupling was developed using cobalt bromide as catalyst. A series of functionalized alkyl bromides and alkyl chlorides were coupled in high yields under mild conditions. This reaction seems to involve a radical intermediate. (Figure presented.).
Cai, Yingxiao,Qian, Xin,Gosmini, Corinne
supporting information
p. 2427 - 2430
(2016/08/16)

Production of Diethyl Terephthalate from Biomass-Derived Muconic Acid
We report a cascade synthetic route to directly obtain diethyl terephthalate, a replacement for terephthalic acid, from biomass-derived muconic acid, ethanol, and ethylene. The process involves two steps: First, a substituted cyclohexene system is built through esterification and Diels-Alder reaction; then, a dehydrogenation reaction provides diethyl terephthalate. The key esterification reaction leads to improved solubility and modulates the electronic properties of muconic acid, thus promoting the Diels-Alder reaction with ethylene. With silicotungstic acid as the catalyst, nearly 100 % conversion of muconic acid was achieved, and the cycloadducts were formed with more than 99.0 % selectivity. The palladium-catalyzed dehydrogenation reaction preferentially occurs under neutral or mildly basic conditions. The total yield of diethyl terephthalate reached 80.6 % based on the amount of muconic acid used in the two-step synthetic process.
Lu, Rui,Lu, Fang,Chen, Jiazhi,Yu, Weiqiang,Huang, Qianqian,Zhang, Junjie,Xu, Jie
supporting information
p. 249 - 253
(2016/01/25)

Merger of Johnson-Claisen rearrangement and alkoxycarbonylation for atom efficient diester synthesis
The orthoester Johnson-Claisen rearrangement of allyl alcohol with triethyl orthoacetate for the synthesis of ethyl 4-pentenoate has been optimized, in order to allow for a selective and efficient subsequent alkoxycarbonylation using formates in an atom efficient manner. Diethyl adipate was successfully yielded in up to 89% applying very low orthoester excess, formic acid and mild reaction conditions in an innovative, one-pot procedure.
Seidensticker, Thomas,M?ller, David,Vorholt, Andreas J.
supporting information
p. 371 - 374
(2016/01/12)

ALTERNATIVE PATHWAYS TO ADIPIC ACID BY COMBINED FERMENTATION AND CATALYTIC METHODS
Processes process for producing adipate or adipic acid using biological pathways and chemical catalyzes are disclosed. Homocitric acid may be a substrate in reaction pathways leading to adipic acid or a salt thereof.
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Paragraph 0138

(2015/09/22)

ALCOHOL-MEDIATED ESTERIFICATION OF CARBOXYLIC ACIDS WITH CARBONATES
A process for making esters from organic acids by means of reacting a carboxylic acid with dialkylcarbonate in an alcohol-containing solvent without any extrinsic acid or base catalyst is described. A benefit of the preparation process is that it can make the separation and extraction of ester products simpler and more facile vis-a-vis conventional isolation techniques.
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Page/Page column 10

(2014/05/24)

PYRIDIN-2YL SULFANYL ACID ESTERS AND PROCESS FOR THE PREPARATION THEREOF
The present invention relates to Pyridin-2-yl sulfanyl acid ester compounds having antiinflammatory properties. The present invention particularly relates to novel anti-inflammatory heterocyclic acid esters of Pyridin-2-yl sulfanyl having the structure of general formula 1 which have been screened for their antiinflammatory activity with respect to inhibition of adhesion of neutrophils, isolated from human peripheral blood, onto the surface of human umbilical vein endothelial cells (HU-VEC) as a result of inhibition of the cytokine-stimulated expression of cell adhesion molecule ICAM-1. The compound RS—Z, 3-(Pyridin-2-yl sulfanyl)-propionic acid pentyl ester (structure 1a, R1=H, R2=H, R3=CH2-COOC5H11) was found to be most effective for ICAM-1 and neutrophil adhesion inhibition and was found to effectively alleviate inflammation mediated by excessive leukocyte infiltration leading to inflammatory disorders or like conditions, such as acute lung injury and acute respiratory distress syndrome in mice.
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Paragraph 0090; 0116; 0117; 0118; 0119-0126; 0150-0154

(2013/06/04)

METHOD FOR CONTINUOUSLY PREPARING CARBOXYLIC ACID ESTER
A method for continuously preparing a carboxylic acid ester is disclosed. In the method of the present invention, a vertical reactor is filled with a solid catalyst, a carboxylic acid and an alcohol are introduced into a lower part of the vertical reactor, esterification is performed to form an esterized mixture, the esterized mixture is output from an upper part of the vertical reactor, and distillation is performed to isolate the carboxylic acid ester. The method of the present invention is simple, easily controlled and environmental friendly, and has significantly high conversion rate and selectivity.
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Paragraph 0027; 0029; 0034

(2013/11/19)

Microwave-assisted aqueous Krapcho decarboxylation
The Krapcho decarboxylation of alkyl malonate derivatives has been adapted to aqueous microwave conditions. Various salt additives were examined, and both the cation and the anion impacted the facility of the reaction. A strong correlation was found between the pKa of the anion and the reaction rate, suggesting a straightforward base-catalyzed hydrolysis. Lithium sulfate gave the best results, obviating the need for DMSO co-solvent. Georg Thieme Verlag Stuttgart · New York.
Mason, Jeremy D.,Murphree, S. Shaun
supporting information
p. 1391 - 1394
(2013/07/26)

Palladium complexes with N-heterocyclic carbene ligands as catalysts for the alkoxycarbonylation of olefins
Palladium catalysts, generated from Pd(OAc)2 and 2 equiv of N,N-dialkylbenzimidazolium iodide, are effective for the alkoxycarbonylation of olefins in high yields (>90%). Alkoxycarbonylation of 1-hexene in dimethylacetamide is achieved within 24 h at 110 C using 1 mol % catalyst, 1000 psi CO, and ethanol. Reactions can be prepared in air, without the need of an acid additive to produce ethyl 2-methylhexanoate and ethyl heptanoate in approximately a 2:1 ratio.
Roberts, Gina M.,Pierce, Philip J.,Woo, L. Keith
p. 2033 - 2036
(2013/05/21)

PYRIDIN- 2 - YL SULFANYL ACID ESTERS AND PROCESS FOR THE PREPARATION THEREOF
The present invention relates to Pyridin-2-yl sulfanyl acid ester compounds having antiinflammatory properties. The present invention particularly relates to novel anti-inflammatory heterocyclic acid esters of Pyridin-2-yl sulfanyl having the structure of general formula 1 which have been screened for their antiinflammatory activity with respect to inhibition of adhesion of neutrophils, isolated from human peripheral blood, onto the surface of human umbilical vein endothelial cells (HUVEC) as a result of inhibition of the cytokine-stimulated expression of cell adhesion molecule ICAM-1. The compound RS-Z, 3-(Pyridin-2-yl sulfanyl)-propionic acid pentyl ester (structure la, R1 = H, R2 = H, R3 = CH2COOC5H11) was found to be most effective for ICAM-1 and neutrophil adhesion inhibition and was found to effectively alleviate inflammation mediated by excessive leukocyte infiltration leading to inflammatory disorders or like conditions, such as acute lung injury and acute respiratory distress syndrome in mice.
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Page/Page column 16

(2012/02/05)

A Ru-Sn-Co/AlO(OH) as a highly efficient catalyst for hydrogenation of dimethyl adipate to 1,6-hexanodiol in aqueous phase
A Ru-Sn-Co/AlO(OH) catalyst was prepared by co-impregnation, calcination, and hydrothermal reduction. The catalyst was well characterized by BET, XRD, SEM-EDX, XPS, H2-TPR, and M?ssbauer spectroscopy, and then it was applied in the hydrogenation of dimethyl adipate to 1,6-hexanodiol in aqueous phase. It was found that the addition of cobalt could stabilize Sn(IV) and the cooperation between tin and cobalt could promote the reduction of ruthenium oxide. The γ-Al2O3 in the catalyst Ru-Sn-Co/γ-Al2O3 was transformed to AlO(OH) by the hydrothermal reduction. It was suggested that the stabilized Sn(IV) and the interaction between the hydroxyl group on the surface of AlO(OH) and the solvent water played a key role to improve the conversion of dimethyl adipate and the selectivity to 1,6-hexanodiol. The conversion of dimethyl adipate and the selectivity to 1,6-hexanodiol were up to 98% and 95%, respectively, under 5 MPa of H2 and 493 K for 10 h.
Jiang, Hong-Bin,Jiang, Hai-Jun,Su, Ke,Zhu, De-Ming,Zheng, Xue-Li,Fu, Hai-Yan,Chen, Hua,Li, Rui-Xiang
p. 164 - 170
(2013/03/13)

Vapor pressures and enthalpies of vaporization of a series of the symmetric linear n -alkyl esters of dicarboxylic acids
Vapor pressures and the molar enthalpies of vaporization of the linear aliphatic alkyl esters of dicarboxylic acids R-CO2-(CH 2)n-CO2-R with n = (0 to 4) with R = C 2H5, n-C3H7, and n-C 4H9 have been determined using the transpiration method. A linear correlation of enthalpies of vaporization (at T = 298.15 K) of the esters with the number n and with Kovat's indices has been found, proving the internal consistency of measured data.
Lipp, Svetlana V.,Krasnykh, Eugenii L.,Verevkin, Sergey P.
body text
p. 800 - 810
(2011/11/05)

CYCLOHEXANE OXIDATION PROCESS BYPRODUCT DERIVATIVES AND METHODS FOR USING THE SAME
Disclosed are ester compositions, solvents, cleaning formulations, curing agents, reactive diluent solvents, controlled acid function release agents, polyol monomers, drilling mud and methods of making and using the same. Disclosed compositions include: a) about 10 to 60 weight percent methyl hydroxycaproate; b) about 20 to 80 weight percent dimethyl adipate; c) about 1 to 15 wt % of dimethyl glutarate; d) about 0.1 to 5 wt % of dimethyl succinate; e) about 0.1 to 7 wt % of at least one cyclohexanediol; and f) less than about 20 wt% oligomeric esters.
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Page/Page column 48-50

(2010/08/05)

Nickel-catalyzed cross-coupling of alkyl zinc halides for the formation of C(sp2)-C(sp3) bonds: Scope and mechanism
Optimal conditions for a general Ni-catalysed Negishi cross-coupling of alkyl zinc halides with aryl, heteroaryl and alkenyl halides have been determined. These conditions allow the reaction to take place smoothly, with low catalyst loading, and in the pr
Phapale, Vilas B.,Guisan-Ceinos, Manuel,Bunuel, Elena,Cardenas, Diego J.
supporting information; experimental part
p. 12681 - 12688
(2010/06/12)

Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer-Villiger reaction. Synthesis of dicarboxylic acid esters
The acid-catalyzed oxidation of cycloalkanones C5-C8 and C12 with hydrogen peroxide in alcohols was performed, and dicarboxylic acid esters were obtained as the major products in 53-70% yields. In the first step, geminal bishydroperoxides are generated from five-to-seven-membered cyclic ketones. The Baeyer-Villiger reaction is a side process accompanied by the formation of ω-hydroxycarboxylic acid esters.
Terent'ev, Alexander O.,Platonov, Maxim M.,Kashin, Alexey S.,Nikishin, Gennady I.
p. 7944 - 7948
(2008/12/21)

Direct oxidative cleavage of α- and β-dicarbonyls and α-hydroxyketones to diesters with KHSO5
Presented is a methodology to oxidatively cleave α-hydroxyketones and α- or β-diones using the environmentally benign reagent KHSO 5, prepared easily from Oxone, to diesters in one simple transformation. In addition, we undertook a mechanistic study to provide a plausible mechanistic interpretation. These reactions may prove to be valuable alternatives to other related metal-mediated processes.
Yan, Jun,Travis, Benjamin R.,Borhan, Babak
p. 9299 - 9302
(2007/10/03)

Synthesis of α,ω-dicarboxylic acid dimethyl esters from cycloalkanones
Reaction of cycloalkanones with [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo]benzene and subsequent treatment of α-[(2,4-dinitrobenzene)sulfonyl]oxy cycloalkanone intermediates with Oxone and PTSA in MeOH-H2O (6:1, v/v) solution provided dicarboxylic acid dimethyl esters in high yields.
Lee, Jong Chan,Ku, Chang Hoe
p. 1679 - 1680
(2007/10/03)

Microwave promoted facile synthesis of methyl and ethyl carboxylates
Microwave irradiation of carboxylic acids with trialkyl orthoacetate in solvent-free conditions afforded an efficient method for alkylation of carboxylic acids to corresponding alkyl carboxylates.
Lee, Jong Chan,Song, In-Goul,Park, Jin Young
p. 2209 - 2213
(2007/10/03)

Trans-esterification in dry media using ferric perchlorate adsorbed on silica gel
Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic grade silica gel in the presence of ethyl acetate (to be used for trans-esterification) produces a supported reagent, Fe(ClO4)3(EtOAc)6/SiO2. This reagent, has been found effective for the rapid and high yield of esters via trans- esterification on grinding in the presence of alcohols/carboxylic acids using pestle and mortar in the solid state.
Parmar, Anupama,Goyal, Rita,Kumar, Baldev,Kumar, Harish
p. 139 - 143
(2007/10/03)

Selective monoesterification of dicarboxylic acids catalysed by ion-exchange resins
Symmetrical dicarboxylic acids with 4-14 carbon atoms gave selectively the corresponding monoesters in high yields in the transesterification catalysed by strongly acidic ion-exchange resins in ester-hydrocarbon mixtures. It was found that the rate of the esterification of the dicarboxylic acids is much higher than that of the monocarboxylic acids formed. This result can explain the high selectivity for the monoester formation and can also be explained by the existence of an aqueous layer on the surface of the resins. This method of selective esterification is quite simple and practical. The Royal Society of Chemistry 1999.
Nishiguchi, Takeshi,Ishii, Yasuhiro,Fujisaki, Shizuo
p. 3023 - 3027
(2007/10/03)

Simple transformation of nitrile into ester by the use of chlorotrimethylsilane
Treatment of nitriles with alcohol and chlorotrimethylsilane at 50°C for 4 h could give esters in fair to good yields. Under similar reaction conditions, intramolecular lactonization via the concomitant nitrile and hydroxy groups in good yield were also demonstrated.
Luo, Fen-Tair,Jeevanandam, Arumugasamy
p. 9455 - 9456
(2007/10/03)

Highly chemoselective, oxyvanadium-catalysed cleavage of α-hydroxy ketones
α-Hydroxy ketones (α-ketols) can be cleaved chemoselectively with a catalytic amount of dichloroethoxyoxyvanadium under an oxygen atmosphere.
Kirihara, Masayuki,Takizawa, Shinobu,Momose, Takefumi
p. 7 - 8
(2007/10/03)

Fe2(SO4)3 · xH2O catalytic esterification of aliphatic carboxylic acids with alcohols
Treatment of various alcohols with aliphatic carboxylic acids in the presence of a catalytic amount of Fe2(SO4)3 · xH2O to give the corresponding esters in good yields.
Zhang, Gui-Sheng
p. 1159 - 1162
(2007/10/03)

α-nitrocycloalkanones as a source of α,ω,-dicarboxylic acid dimethyl esters
α,ω-Dicarboxylic acid dimethyl esters arc easily obtained by ring cleavage of α-nitrocycloalkanones. Thus, reaction of the latter compounds with three equivalents of potassium persulfate, in methanol and in presence of sulfuric acid at 80 °C, provides α,ω-dicarboxylic acid dimethyl esters in high yields. Long-chain, and alkylated α,ω-dicarboxylic acid dimethyl esters can be also efficiently obtained.
Ballini, Roberto,Bosica, Giovanna
p. 16131 - 16138
(2007/10/03)

Synthesis of 2,3-substituted cycloalkanones by ceric ammonium nitrate-promoted oxidative tandem additions of 1-ethoxy-1-[(trimethylsilyl)oxy]cyclopropane to α,β-unsaturated cycloalkenones
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Paolobelli, Anna Belli,Ruzziconi, Renzo
p. 6434 - 6437
(2007/10/03)

Simple and rapid determination of the activation parameters of organic reactions by temperature-dependent NMR spectroscopy II. Application to reversible reactions
A non-isothermal (NIT) method for evaluating the activation enthalpies and entropies of reactions in solutions was applied to several reversible reactions. This was realized by a stepwise elevation of the temperature of a reaction system using a variable-temperature apparatus comprising on NMR spectrometer and a quick collection of FID (free induction decay) at every plateau of the step. The rate from NIT experiments agreed well with the previously measured rates by the conventional methods.
Satoh, Masahiro,Hirota, Minoru
p. 2619 - 2624
(2007/10/03)

A facile conversion of halides, alcohols and olefins to esters using iron(III) perchlorate
A facile method has been developed for the esterification of halides/alcohols/olefins with carboxylic acids using iron(III) perchlorate.
Kumar,Kumar,Parmar
p. 1087 - 1094
(2007/10/02)

Carbonylation of alkyl sulfonates catalyzed by cobalt complexes
Alkyl sulfonates (R1-OSO2R2) react with carbon monoxide and alcohol (R3-OH) in the presence of catalytic amounts of Co complex and Nal to afford the corresponding esters (R1-COOR3) in moderate to good yields.
Urata, Hisao,Goto, Daisuke,Fuchikami, Takamasa
p. 3091 - 3094
(2007/10/02)

Process for the preparation of a diester of adipic acid
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(2008/06/13)

Process for the preparation of a diester of adipic acid
Process for preparing adipic acid or esters thereof by: (1) reacting 1,3-butadiene with CO and water or an alcohol with formation of pentenoic acid or esters thereof in the presence of a first carbonylation catalyst comprising a Pd compound and a polydentate ligand containing P, As or Sb, (2) isolating pentenoic acid or esters thereof from the reaction mixture, and (3) reacting the isolated pentenoic acid or esters with CO and water or an alcohol in the presence of a second carbonylation catalyst.
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(2008/06/13)

1,3-Dimethyl-2-phenylbenzimidazoline as a Novel and Efficient Reagent for Mild Reductive Dehalogenation of α-Halo Carbonyl Compounds and Acid Chlorides
1,3-Dimethyl-2-phenylbenzimidazoline (DMBI) has been found to be a powerful, chemoselective, and useful reducing agent for mild reductive dehalogenation of a variety of α-halo carbonyl compounds (halo = Br, Cl, F) and acid chlorides.The reduction of α-halo ketones, aldehydes, esters, lactones, and carboxylic acids with this new reagent in ether is quity selective and clean and generally proceeds in almost quantitative yields at moderate temperatures with no additives.The order of relative reactivities in a series of α-halo carbonyl compounds was Br>Cl>F (for halides), primary>secondary>tertiary (for substitution at the halogenated carbon), and cyclohexyl>cyclododecyl (for ring size).The reduction of α-bromocamphor with DMBI-2-d led stereospecifically to the formation of camphor-3-exo-d.Based on these results together with experiments with para-substituted DMBIs, the mechanism of the present dehalogenation reaction of α-halo carbonyl compounds is postulated to proceed via a simple linear transition state (direct SN2 displacement) featuring an attack on the halogenated carbon center by hydrogen at the C-2 position of DMBI as a hydride.Reductive dechlorination of acid chlorides to the corresponding aldehydes or aldehyde-d with DMBI or DMBI-2-d has also been achieved most effectively in the presence of an acetic acid catalyst.
Chikashita, Hidenori,Ide, Hisao,Itoh, Kazuyoshi
p. 5400 - 5405
(2007/10/02)

Process for producing cyanovaleric esters and caprolactam
Caprolactam can be produced with an economical advantage without formation of by-products in a high yield by subjecting adipic acid and adiponitrile to interchange reaction at an elevated temperature, adding an alcohol directly to the interchange reaction mixture without isolating the resulting cyanovaleric acid to esterify the cyanovaleric acid with said alcohol into a cyanovaleric ester, reducing the cyanovaleric ester with a catalyst into an aminocaproic ester, heating the aminocaproic ester in a polyhydric alcohol having a higher boiling point than that of caprolactam to convert the ester into caprolactam, isolating the caprolactam by distillation and recycling the liquid distillation residue to the system for heating said polyhydric alcohol and said aminocaproic ester.
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(2008/06/13)