7195-44-0Relevant academic research and scientific papers
Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA)
Deng, Jun,Liu, Xiaoqing,Li, Chao,Jiang, Yanhua,Zhu, Jin
, p. 15930 - 15939 (2015)
A bio-based epoxy monomer, diglycidyl ester of 2,5-furandicarboxylic acid (DGF) was synthesized for the first time from the renewable 2,5-furandicarboxylic acid (FDCA). For comparison study, its petroleum-based counterpart, diglycidyl ester of terephthalic acid (DGT) was also prepared. Their chemical structures were confirmed in detail by 1H NMR, 13C NMR and FT-IR before they were cured by methylhexahydrophthalic anhydride (MHHPA) and poly(propylene glycol)bis(2-aminopropyl ether) (D230), respectively. The curing behaviors were investigated using differential scanning calorimetry (DSC). The thermal mechanical properties and thermal stabilities of the cured resins were evaluated using dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA). Results showed that DGF displayed higher curing activity, elevated glass transition temperature and similar mechanical properties compared with those of the cured DGT. This study indicated that FDCA had a huge potential to replace the petroleum-based terephthalic acid in the synthesis of epoxy resins with satisfactory performance.
Synthesis method of diglycidyl p-phthalate
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Paragraph 0007; 0008; 0019-0029, (2019/01/15)
The invention discloses a synthesis method of diglycidyl p-phthalate in the field of organic synthesis. The method comprises the following steps: (1) generating a chlorohydrin intermediate by using terephthalic acid and epoxy chloropropane as raw materials, quaternary ammonium salt as a catalyst, a protic solvent and/or Lewis acid metal salt as additive(s); (2) synthesizing the diglycidyl p-phthalate by enabling the generated chlorohydrin intermediate under the action of an organic solvent and inorganic strong base. The synthesis method increases the yield of an esterification reaction and reduces the formation of by-products by adding the additive(s) to the esterification reaction. An appropriate amount of the protic solvent is added, so that the by-products of the esterification reactioncan be significantly reduced; due to the addition of an appropriate amount of Lewis acid, the yield of the esterification reaction is increased. Moreover, the synthesis method can effectively improvethe purity of the obtained diglycidyl p-phthalate crude product and reduce the difficulty of subsequent purification. The two steps are simple to operate, and post-treatment is convenient, so that the synthesis method is suitable for industrial production.
Quaternary Alkyl Ammonium Salt-Catalyzed Transformation of Glycidol to Glycidyl Esters by Transesterification of Methyl Esters
Tanaka, Shinji,Nakashima, Takuya,Maeda, Toshie,Ratanasak, Manussada,Hasegawa, Jun-Ya,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
, p. 1097 - 1103 (2018/02/14)
Catalytic transformation of glycidol while maintaining its epoxide moiety intact is challenging because the terminal epoxide that interacts with the hydroxyl group via a hydrogen bond is labile for the ring-opening reaction. We found that a quaternary alkyl ammonium salt catalyzes the selective transformation of glycidol to glycidyl esters by transesterification of methyl esters. The developed method can be applied to the synthesis of multiglycidyl esters, which are valuable epoxy resin monomers. Mechanistic studies revealed the formation of a binding complex of glycidol and quaternary alkyl ammonium salt in a nonpolar solvent and the generation of the alkoxide anion as a catalyst through the ring-opening reaction of the epoxide. Computational studies of the reaction mechanism indicated that the alkoxide anion derived from glycidol tends to abstract the proton of another glycidol rather than work as a nucleophile, initiating the catalytic transesterification. Payne rearrangement of the deprotonated glycidol, which produces a destabilized base that promotes nonselective reactions, is energetically unfavorable due to the double hydrogen bond between the anion and diol. The minimal interaction between the quaternary alkyl ammonium cation and the epoxide moiety inhibited the random ring-opening pathway leading to polymerization.
Synthesis technology of diglycidyl p-phthalate
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Paragraph 0033; 0034; 0037; 0038; 0041; 0042; 0045; 0046, (2018/09/21)
The invention relates to a technology for synthesizing diglycidyl p-phthalate and in particular relates to synthesis of the diglycidyl p-phthalate by utilizing terephthalic acid and epichlorohydrin through a step-by-step esterification-closed ring elimination-refining three-step method, and belongs to the field of organic chemical industry. In step-by-step esterification reaction, a quaternary phosphonium salt type catalyst triphenylphosphonium bromide is adopted and N,N-dimethylformamide is used as a co-solvent; the epichlorohydrin is added by three steps so as to effectively prevent excessive epichlorohydrin from self-polymerization or being polymerized with other products; in a closed ring elimination process, water is removed by vacuumizing a reaction system and a target product is prevented from being hydrolyzed to the greatest extent; a reaction technology has moderate conditions and a post-treatment technology is simple and environmentally friendly; the epoxy value and yield ofa product are relatively high and the technology is suitable for industrial production.
METHOD FOR PRODUCING GLYCIDYL ESTER
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Paragraph 0032; 0034-0038; 0040-0041, (2017/11/09)
PROBLEM TO BE SOLVED: To provide a production method which makes it possible to obtain glycidyl ester with high yields from the ester exchange reaction between ester and glycidol with a convenient catalyst in a mild reaction condition. SOLUTION: Glycidyl ester is produced by the ester exchange reaction between ester and glycidol in the presence of a polystyrene-carrying quaternary ammonium salt. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Using PTA a phthalic acid residue two glycidyl ester method (by machine translation)
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Paragraph 0018; 0019, (2017/02/09)
This invention is a kind of using PTA phthalic acid residue two glycidyl ester method, belonging to the field of organic synthesis. In accordance with the following steps: to PTA residue and epoxychloropropane as the starting material, by adding a certain amount of organic solvent, in the heating and under the action of catalyst, a epoxy ring-opening and esterification reaction, and then under the action of the inorganic alkali, a ring-closing reaction, to produce the final product phthalic acid b acid water glycerlol. The invention provides to PTA secondary residue as raw materials, has accomplished the recycling of resources, so that the cost of raw materials is greatly reduced, at the same time effectively protect the environment; the use of a solvent method greatly reduces the epoxychloropropane consumption, avoiding the problem of recovery and reuse of the epichlorohydrin, epoxy value of the product is improved and production rate, promoting the wide application of the epoxy resin. (by machine translation)
Preparation of glycidyl esters
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, (2008/06/13)
Glycidyl esters are prepared by reacting a compound containing one or more ethylenically unsaturated ester groups with hydrogen peroxide in the presence of an alkali metal or alkaline earth metal salt of tungstic acid, phosphoric acid and a phase transfer catalyst, optionally in the presence of one or more solvents.
Process for the production of aromatic glycidyl esters
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, (2008/06/13)
Aromatic mono or polycarboxylic acid glycidyl esters are obtained in good yields and high purity by transesterification of the corresponding aromatic carboxylic acid alkyl esters with glycidol in the presence of weakly toxic catalysts, namely the alkali, ammonium, and alkaline earth metal salts of pseudohalogen hydride acids with readily polarizable anions.
