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.
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.
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.
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.
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.
Biomass-derived dibasic acids to diesters with inorganic ligand-supported catalyst: synthesis, optimization, characterization
Chen, Zhe,Han, Sheng,Lu, Deli,Xu, Yumeng
, (2021)
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.
Method for catalyzing esterification reaction of low-carbon alcohol by using ionic liquid
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Paragraph 0041-0048, (2021/07/24)
The invention discloses a method for catalyzing low-carbon alcohol esterification reaction by ionic liquid, which comprises the following steps: mixing dianhydride or diacid, fatty alcohol and ionic liquid, heating to 100-160 DEG C by microwave, and reacting for 0.5-2 hours to obtain diester; wherein the ionic liquid is [Ps2TMEDA] [HSO4] 2 and/or [Ps2BPy] [HSO4] 2, the molar ratio of the ionic liquid to the dianhydride or diacid is 0.005-0.04, and the molar ratio of the dianhydride or diacid to the fatty alcohol is 1-5. The method is simple in process, mild in condition, convenient to operate, environment-friendly, high in double esterification degree, high in ionic liquid activity and easy to separate.
Diphosphine compound, catalyst system containing diphosphine compound and application of diphosphine compound
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Paragraph 0108-0109; 0121-0122, (2021/03/13)
The present invention provides a diphosphine compound, a catalyst system containing the same, and applications of the diphosphine compound, the diphosphine compound has a structure represented by a formula I or a formula II, a phosphorus atom and a benzene ring are connected through methylene, and a nitrogen-containing heteroaryl structure is matched, such that carbon monoxide can be easily activated after phosphorus and a metal are coordinated, and an alkoxy carbonylation reaction is facilitated. The catalyst system comprises a bimetallic catalyst and the diphosphine compound, and when the catalyst system is used for catalyzing conjugated olefin to prepare 1, 6-dicarboxylic ester compounds, the conversion rate of raw materials can be effectively improved, and the yield and regioselectivity of products are improved.
