1572-92-5Relevant articles and documents
Preparation method of 1,4-butanediol and dicarboxylic acid ester thereof
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Paragraph 0054; 0055, (2019/10/01)
The invention relates to a preparation method of 1,4-butanediol and a dicarboxylic acid ester thereof. Specifically, the preparation method of 1,4-butanediol and the dicarboxylic acid ester thereof comprises the following steps: performing hydrodecarbonylation esterification ring-opening on a furoic acid compound, a trifluoromethanesulfonate, a hydrogenation catalyst in a carboxylic acid solvent to obtain a 1,4-butanediol dicarboxylic acid ester. The method has the characteristics of simple process, easy purification, high yield, green safety, and the like, and is suitable for large-scale industrial production.
Esterification of carboxylic acids with alkyl halides using imidazolium based dicationic ionic liquids containing bis-trifluoromethane sulfonimide anions at room temperature
Jadhav, Arvind H.,Lee, Kyuyoung,Koo, Sangho,Seo, Jeong Gil
, p. 26197 - 26208 (2015/10/20)
Task-specific room temperature ionic liquids (RTILs) composed of symmetrical N-methylimidazolium rings linked with a short oligo (ethylene glycol) chain (cationic part) and bis-trifluoromethane sulfonimide (NTf2, anionic part) were successfully synthesized, and their physicochemical properties were determined by various modern analytical techniques. The catalytic activity of the synthesized RTILs was evaluated in the esterification reaction of acids with alkyl halides in solvent-free conditions at room temperature. From the screening test, all the synthesized RTILs showed a high yield with significant selectivity for respective esters in a very short reaction time. Especially, 0.1 equimolar of RTIL-1 ([tetraEG(mim)2][NTf2]2) was found to be, the most efficient and reusable catalyst for this reaction. As a result, 100% conversion and up to a 94% yield of the respective ester product was obtained in a 30 min reaction time. This might be due to their synergetic effect of Lewis acidity, wide liquid range, and high miscibility compared to the other homogeneous and heterogeneous catalysts. Beside this, RTIL was easily separated from the reaction mixture and reused several times without any significant loss of catalytic activity and structural property. The present dicationic ionic liquids (ILs) under a solvent-free catalytic system were found to be kinetically fast, naturally benign, and achieved good yields for esterification of carboxylic acids with alkyl halides.
PROCESS FOR PREPARING 1,4-BUTANDIOL MONONITRATE
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Page/Page column 25-27; 28, (2009/03/07)
The present invention relates to a process for the preparation of 1,4-butanediol mononitrate as intermediate for large scale preparation of high purity nitrooxybutyl ester of pharmaceutically active compounds.
Convenient Selective Monoacylation of 1,n-Diols Catalyzed by Ion-Exchange Resins
Nischiguchi, Takeshi,Fujisaki, Shizuo,Ishii, Yasuhiro,Yano, Yoshihiro,Nishida, Akiko
, p. 1191 - 1195 (2007/10/02)
Several 1,n-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were selectively monoacylated by transestrification in ester/octane solvent mixtures catalyzed by strongly acidic ion-exchange resisns.This method of selective esterification is quite simple and practical.The selectivity for monoester formation and initial rates of monoester formation depended on the ester/octane ratio of the solvents.The reasons for the selectivity are as follows: (1) The sulfonic acid-type ion-exchange resins usually contain 50-80percent water, and a strongly acidic aqueous layer is formed on the surface of the resins. (2) A partition equilibrium between the aqueous layer and the aprotic ester/octane layer is setup, and diols have higher partition coefficients than the product monoesters. (3) Acylation of the alcohols occurs in the aqueous layer and/or at the interface between the aqueous and the nonaqueous liquid layer. (4) The formed monoesters move away from the aqueous layer into the aprotic layer.
Highly Selective Monoacylation of Symmetric Diols Catalyzed by Metal Sulfates Supported on Silica Gel
Nishiguchi, Takeshi,Kawamine, Katsumi,Ohtsuka, Tomoko
, p. 312 - 316 (2007/10/02)
Several 1,α-diols, ranging from 1,2-ethanediol to 1,16-hexadecanediol, were monoacylated with high selectivity by reaction with esters in the presence of metal sulfates or hydrogen sulfates, like Ce(SO4)2 and NaHSO4, supported on silica gel.Symmetrical secondary diols were also selectively monoformylated, by reaction with ethyl formate.This method of selective esterification is simple and practical.The yield of monoester depends upon both the composition and the volume of the solvent (an ester/alkane mixture).Unsupported NaHSO4 also catalyzed monoacylation, but the selectivity was less than in monoacylations catalyzed by the supported reagent.The selectivity can be explained by the following reasons: (1) monoacylated products are formed selectively because the diol, but not the monoester, is preferentially adsorbed on the surface of the catalysts, where esterification then occurs, and (2) thin diol layers are formed on the surface of the catalysts due to limited solubility of the diols in the solvent.
Preparation of Carboxylate Esters of Polyhydric Alcohols by Using a Sulfonated Charcoal Catalyst
Prager, Rolf H.,Yurui, Zhang
, p. 1003 - 1005 (2007/10/02)
Ethane-1,2-diol, propane-1,2-diol, butane-1,4-diol and propane-1,2,3-triol are readily esterified by carboxylic acids in near quantitative yields in the presence of a sulfonated charcoal catalyst.
