Exploration into a New Dicarboxylic Acid Derived from Ricinoleic Acid for High-Performance Aluminum Electrolytic Capacitors

Mizota, Isao; Umeshima, Satoshi; Matsunaga, Sei; Isomura, Rinpei; Nakahama, Kenta; Shimizu, Makoto; Yokomori, Yorozu; Umemura, Tokihiro; Kuroki, Noburo; Kiyosawa, Junich; Tanaka, Hiroyuki

doi:10.1246/bcsj.20160267

Cited by 4 publications

(8 citation statements)

References 14 publications

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“…Due to its rigid cyclic structures, it is capable of repairing them on the surface and forming thicker layers so as to achieve the high withstand voltage . Although there are still some issues to be overcome, such as the fact that scintillation is observed from around 550 V, and the solubility in EG is slightly inferior, we concluded that the incorporation of hindered α-substituents led to excellent heat resistance and rigid ring skeletons improved the withstand voltage . The details of the correlation between molecular rigidity and withstand voltage are currently under research.…”

Section: Results and Discussionmentioning

confidence: 99%

“…On the other hand, we have started to collaborate with NICHICON Corporation to explore new chemical structure of dicarboxylic acids for the development of next-generation AECs. We reported in 2016 that dicarboxylic acids derived from ricinoleic acid showed good heat resistance and withstand higher voltage compared with sebacic acid and 1,6-DDA for AEC (Scheme c) . The solubility of these compounds in EG is, however, still a problem.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Dicarboxylic Acids Comprising an Ether Linkage and Cyclic Skeleton and Its Further Application for High-Performance Aluminum Electrolyte Capacitors

Mizota,

Yamamoto,

Kaliyamoorthy

et al. 2024

ACS Omega

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Aluminum electrolytic capacitors are essential components in all electronic devices, and it is known that their longevity depends on the performance of their electrolytes. We synthesized dicarboxylic acids having ether bonds showing the good solubility in ethylene glycol as a solvent and simultaneously developed a complete halogen removal method, which is strictly prohibited in capacitors. Moreover, the incorporation of bulky α-substituents and cyclic structures dramatically improved their heat resistance and can withstand high voltage, i.e., 764 V.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Dicarboxylic Acids Comprising an Ether Linkage and Cyclic Skeleton and Its Further Application for High-Performance Aluminum Electrolyte Capacitors

Mizota,

Yamamoto,

Kaliyamoorthy

et al. 2024

ACS Omega

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“…Oxidation of methyl ricinoleate was carried out following a reported method with slight modification. [ 20 ] PCC (5.16 g, 24 mmol) was taken in 100 mL of dichloromethane (DCM) and methyl ricinoleate (5g, 16 mmol) was added and the reaction mixture was stirred at room temperature (27 ˚C) for 12 h. After maximum conversion, the mixture was filtered on a celite‐silica bed followed by purification by column chromatography to obtain methyl 12‐oxo‐ cis ‐9‐octadecenoate as oily liquid (4.1 g, 83%). R f : 0.6 in 10% EtOAc in hexane.…”

Section: Methodsmentioning

confidence: 99%

Design and Synthesis of Sebacic Acid from Castor Oil by New Alternate Route

Bhukya

Kaki

2022

Euro J Lipid Sci & Tech

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A simple and alternate organic synthetic route for sebacic acid, a high value ten‐carbon aliphatic dicarboxylic acid from castor oil is described in this study. Castor oil methyl esters are purified to obtain methyl ester of ricinoleic acid that is used as the starting material for the preparation of sebacic acid. The hydroxyl group of methyl ricinoleate is oxidized to corresponding 12‐oxo derivative followed by isomerization of the cis 9, 10 olefinic bond to trans 10, 11 isomer. The isomerized compound is subjected to dihydroxylation followed by oxidative cleavage and subsequent methylation to obtain dimethyl decanedioate. The dimethyl decanedioate is finally hydrolyzed to obtain sebacic acid. The intermediate compounds and final product are purified and characterized by chromatographic and spectral analysis. The final compound is analyzed by 1H and 13C‐NMR as well as high resolution mass spectrometry and compared with standard compound for the confirmation of the structure. Practical Applications: The design and preparation of sebacic acid by the novel alternate route is described. Castor oil, a renewable source, is utilized as the raw material for the preparation of sebacic acid. Isomerization of the 9, 10 cis bond to 10, 11 trans bond is the key step in the synthesis of sebacic acid. The chemical transformation of castor oil to sebacic acid by newer route is investigated.

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“…After the completion of the reaction, as identified by TLC, the resulting mixture was filtered over Celite and washed well with methanol. The filtrate was collected and the solvent was removed under vacuum to get the pure product …”

Section: Methodsmentioning

confidence: 99%

“…The filtrate was collected and the solvent was removed under vacuum to get the pure product. 36 2.3.2. General Procedure for the Synthesis of Ricinoleic Acid Hydrazide 2a and 2b.…”

Section: Methodsmentioning

confidence: 99%

Glycolipid-Based Oleogels and Organogels: Promising Nanostructured Structuring Agents

Thamizhanban

Balaji

Lalitha

et al. 2020

J. Agric. Food Chem.

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Over the past few decades, the scientific community is actively involved in the development of edible structuring agents suitable for food, cosmetics, agricultural, pharmaceutical, and biotechnology applications. In particular, edible oil structuring using simple amphiphiles would be the best alternative for the currently used trans and saturated fatty acids, which cause deleterious health effects and cardiovascular problems. In this report, we have made an attempt to address the aforementioned consequences, by synthesizing a new class of structuring agents by a judicious combination of δ-gluconolactone and ricinoleic acid, compounds classified as GRAS, using simple steps in good yield. To our delight, the synthesized glycolipids self-assemble in a wide variety of vegetable oils and commercially viable glycerol, ethylene glycol, and polyethylene glycol via various intermolecular interactions to form a gel. The morphology of molecular gels was investigated by optical microscopy and FESEM analysis, which reveal the existence of a tubular architecture with a diameter ranging from 75 to 150 nm. Rheological studies disclosed the viscoelastic nature, thermal processability, and thixotropic behavior of both oleogels and organogels. Altogether, self-assembled oleogel and organogel reported in this paper would potentially be used in food, agricultural, cosmetics, pharmaceutical, and biotechnological applications.

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Exploration into a New Dicarboxylic Acid Derived from Ricinoleic Acid for High-Performance Aluminum Electrolytic Capacitors

Cited by 4 publications

References 14 publications

Synthesis of Dicarboxylic Acids Comprising an Ether Linkage and Cyclic Skeleton and Its Further Application for High-Performance Aluminum Electrolyte Capacitors

Synthesis of Dicarboxylic Acids Comprising an Ether Linkage and Cyclic Skeleton and Its Further Application for High-Performance Aluminum Electrolyte Capacitors

Design and Synthesis of Sebacic Acid from Castor Oil by New Alternate Route

Glycolipid-Based Oleogels and Organogels: Promising Nanostructured Structuring Agents

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