105-99-7Relevant articles and documents
Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer-Villiger reaction. Synthesis of dicarboxylic acid esters
Terent'ev, Alexander O.,Platonov, Maxim M.,Kashin, Alexey S.,Nikishin, Gennady I.
, p. 7944 - 7948 (2008)
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.
The synthesis of di-carboxylate esters using continuous flow vortex fluidics
Britton, Joshua,Dalziel, Stuart B.,Raston, Colin L.
, p. 2193 - 2200 (2016)
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.
Synergism of microwaves and immobilized enzyme catalysis in synthesis of adipic acid esters in nonaqueous media
Yadav, Ganapati D.,Lathi, Piyush S.
, p. 1699 - 1705 (2005)
Low-energy microwave irradiation leads to enhancement by a factor of up to 2.63 in comparison with conventional heating in immobilized lipase-catalyzed esterification of adipic acid with various alcohols and this effect is due to the greater frequency of collision, without any change in activation energy of the two modes of heating. Copyright Taylor & Francis, Inc.
Assisted Tandem Catalytic Conversion of Acrylates into Adipic Esters
Maity, Pradip K.,Tunge, Jon A.
, p. 3419 - 3423 (2018)
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.
Zirconia-supported rhenium oxide as an efficient catalyst for the synthesis of biomass-based adipic acid ester
Lin, Jinchi,Song, Haiyan,Shen, Xiaoru,Wang, Binju,Xie, Shunji,Deng, Weiping,Wu, Deyin,Zhang, Qinghong,Wang, Ye
, p. 11017 - 11020 (2019)
Synthesis of adipic acid, a key monomer of nylon-66 and polyurethane, from biomass is highly attractive for establishing green and sustainable chemical processes. Here, we report that zirconia-supported rhenium oxide (ReOx/ZrO2) efficiently catalyses the deoxydehydration of cellulose-derived d-glucaric acid, offering adipic acid ester with a yield of 82% by combining with a Pd/C catalyst in subsequent reactions.
Synthesis of carboxylic acid esters in the presence of micro- and mesoporous aluminosilicates
Grigor'Eva,Suleimanova,Agliullin,Kutepov
, p. 773 - 779 (2014)
The catalytic properties of zeolites HY, HBeta, and HZSM-12 and of mesoporous amorphous aluminosilicate in liquid-phase esterification of aliphatic (monobasic C1-C18, dibasic C6, C10) and aromatic (benzoic, trimellitic, phthalic) carboxylic acids with butanol were studied. Zeolite HBeta appeared to be the most active catalyst. Procedures were developed for preparing esters in the presence of zeolitic catalyst HBeta, ensuring 100% selectivity of ester formation at 90-98% conversion of the acid.
Approaches for scale-up of microwave-promoted reactions
Bowman, Matthew D.,Holcomb, Jennifer L.,Kormos, Chad M.,Leadbeater, Nicholas E.,Williams, Victoria A.
, p. 41 - 57 (2008)
In this report, we look at a range of classes of reaction involving microwave heating and show how different processing techniques can be used to address scale-up needs. We look at both batch and continuous-flow processing. We have shown that when using batch methodologies working using an open reaction vessel offers operational advantages while still giving good yields of desired products. In cases where open-vessel conditions are not amenable or where particularly volatile or toxic reagents are used, parallel sealed vessels can offer an alternative approach. For continuous-flow processing, homogeneity of the reaction mixture is key. When the mixture is homogeneous, it is possible to move from small-scale sealed-vessel conditions to the continuous-flow apparatus without any modification of reaction conditions or loss in product yield. When either the starting materials or the product mixture contains particulate matter, continuous processing can prove a challenge, but reoptimization of reaction conditions as well as reduction of the concentration may allow these difficulties to be overcome.
Ionic liquid-mediated deoxydehydration reactions: Green synthetic process for bio-based adipic acid
Shin, Nara,Kwon, Sohyun,Moon, Sojeong,Hong, Chae Hwan,Kim, Young Gyu
, p. 4758 - 4765 (2017)
A novel recyclable Re-catalyzed deoxydehydration (DODH) reaction was developed with an ionic liquid (IL) as a reaction medium for an efficient synthesis of adipic acid (1), one of the commercially important dicarboxylic acids, from biomass galactaric acid. The carefully designed solubility of ILs allowed a homogeneous DODH reaction to produce muconate 3 in excellent yields, a key intermediate for 1. Use of the IL also enabled an efficient separation of the DODH product 3 from the reaction mixture by simple decantation. The recovered IL layer containing the expensive Re catalyst was reused up to four times, yielding 3 without much decrease in yields. The target compound 1 was also produced in an excellent yield with the catalytic hydrogenation of 3 followed by the acidic hydrolysis. Thus, the overall process for bio-based adipic acid would become much more cost-effective, eco-friendly, and industrially viable, which could be applied to various biomass conversions.
Convenient selective monoesterification of α, ω-dicarboxylic acids catalyzed by ion-exchange resins
Saitoh, Masahiko,Fujisaki, Shizuo,Ishii, Yasuhiro,Nishiguchi, Takeshi
, p. 6733 - 6736 (1996)
Symmetric dicarboxylic acids, ranging from pentanedioic acid to tetradecanedioic acid, gave selectively the corresponding monoesters in high yields in the transesterification catalyzed by strongly acidic ion-exchange resins in ester/octane mixtures.
Synthesis of esters of dioxane alcohols and their performance as plasticizers for polyvinyl chloride compounds
Glazko,Gur'yanova,Levanova,Kozlova,Neiman
, p. 950 - 954 (2005)
A procedure was developed for preparing a plasticizer for polyvinyl chloride compounds from the fraction of dioxane alcohols. The main physicochemical properties of the new plasticizer were determined. Items prepared from formulations containing the new plasticizer were fabricated and tested in laboratory.
