33498-48-5

Upstream product

• 110-63-4 Butane-1,4-diol 
• 802294-64-0 propionic acid 
• 123-62-6 propionic acid anhydride 
• 105-37-3 Ethyl propionate 
• 554-12-1 propanoic acid methyl ester 

Relevant academic research and scientific papers

PROCESS FOR PREPARING 1,4-BUTANDIOL MONONITRATE

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

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

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.