2598-99-4Relevant academic research and scientific papers
Efficient greener methodology for the preparation of bio-based phase change materials from lipids
Y?ld?r?m, Ayhan,K?raylar, Kaan
, p. 407 - 413 (2020/11/19)
In the present work, a new, highly efficient and simple strategy has been developed for the synthesis of long chain esters from fatty acids and fatty alcohols as phase change materials. Equivalent amounts of the selected starting compounds were taken to the esterification reaction at 110 °C in a solventless medium. In order to catalyze the esterification reaction, non-hygroscopic triphenylphosphine-sulfur trioxide adduct was used (0.83 mmol%) which is an easily accessible compound. The relevant reaction was completed in a very short time (2 h) and under optimized esterification conditions, excellent conversion were reached. The targeted mono ester compounds (15 examples) were obtained in good to excellent yields even after a simple crystallization step (72-99%). Additionally, a catalyst reuse investigation and study covering the scale-up production of stearyl stearate was also carried out. The triphenylphosphine-sulfur trioxide catalyzed solvent free process can compete with existing processes and proved to be a cheaper, practical and environmentally-friendly method for the esterification of fatty acids and alcohols.
Protic acid immobilized on solid support as an extremely efficient recyclable catalyst system for a direct and atom economical esterification of carboxylic acids with alcohols
Chakraborti, Asit K.,Singh, Bavneet,Chankeshwara, Sunay V.,Patel, Alpesh R.
supporting information; experimental part, p. 5967 - 5974 (2009/12/24)
(Chemical Equation Presented) A convenient and clean procedure of esterification is reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4-SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols has been achieved to afford the corresponding esters in excellent yields. Chiral alcohol and N-t-Boc protected chiral amino acid also resulted in ester formation with the representative carboxylic acid or alcohol without competitive N-t-Boc deprotection and detrimental effect on the optical purity of the product demonstrating the mildness and chemoselectivity of the procedure. The esters of long-chain (>C10) acids and alcohols are obtained in high yields. The catalyst is recovered and recycled without significant loss of activity. The industrial application of the esterification process is demonstrated by the synthesis of prodrugs of ibuprofen and a few commercial flavoring agents. Other protic acids such as H2SO4, HBr, TfOH, HBF4, and TFA that were adsorbed on silica gel were less effective compared to HClO4-SiO2 following the order HClO4-SiO 2 ? H2SO4-SiO2 > HBr-SiO 2 > TfOH-SiO2 ? HBF4-SiO2 ≈ TFA-SiO2. When HClO4 was immobilized on other solid supports the catalytic efficiency followed the order HClO4-SiO 2 > HClO4-K10 > HClO4-Al 2O3 (neutral) > HClO4-Al2O 3 (acidic) > HClO4-Al2O3 (basic).
Liquid-liquid biphasic synthesis of long chain wax esters using the Lewis acidic ionic liquid choline chloride·2ZnCl2
Sunitha, Sadula,Kanjilal, Sanjit,Reddy, P. Srinivasa,Prasad, Rachapudi B.N.
, p. 6962 - 6965 (2008/02/13)
The first liquid-liquid biphasic synthesis of wax esters in a Lewis acidic ionic liquid, choline chloride·2ZnCl2 by the esterification of long chain carboxylic acids with long chain alcohols is described. The reported reaction system has the advantages of both homogeneous and heterogeneous catalysis with high product yield and the ease of product as well as catalyst separation without the use of an organic solvent. The ionic liquid studied plays the dual role of solvent as well as catalyst and is recycled up to six times without any significant loss of activity.
PROCESS FOR PRODUCING CARBOXYLIC ACID ESTER AND ESTERIFICATION CATALYST
-
Page/Page column 13-14, (2008/06/13)
A process for carboxylic acid ester production by which a carboxylic acid ester comprising an alcohol and a carboxylic acid each having 10 or more carbon atoms can be produced in a high yield. The catalyst used can be reused. The process generates a small amount of wastes and is less apt to pose an environmental problem. Also provided is an esterification catalyst usable in the process. In the esterification of a C10 or higher carboxylic acid and a C10 or higher alcohol, use is made, as a catalyst, of a hydrate of a salt of at least one metal selected among aluminum, gallium, indium, iron, cobalt, nickel, zinc, zirconium, hafnium, and niobium.
Efficient esterification of long chain aliphatic carboxylic acids with alcohols over ZrOCl2·8H2O catalyst
Mantri, Kshudiram,Komura, Kenichi,Sugi, Yoshihiro
, p. 1939 - 1944 (2007/10/03)
Direct condensation of equimolar amounts of long chain carboxylic acids and alcohols could be achieved by using zirconyl chloride as an efficient catalyst. ZrOCl2·SH2O showed high activity for esterification between primary acids and alcohols; however, it was less active in the combination of branched acid and secondary alcohols to give the corresponding esters. Georg Thieme Verlag Stuttgart.
Esterification of long chain aliphatic acids with long chain alcohols catalyzed by multi-valent metal salts
Mantri, Kshudiram,Nakamura, Ryo,Komura, Kenichi,Sugi, Yoshihiro
, p. 1502 - 1503 (2007/10/03)
Some typical multi-valent metal salts, such as chloride, nitrate, sulfate, and acetate of Fe(III), Al(III), Ga(III), In(III), Zr(IV), Hf(IV), Zn(II), Co(II), Ni(II), Mn(III), Cr(III), and Cu(II) have catalytic acitivties for the esterification of saturated and unsaturated long chain aliphatic acids with long chain aliphatic alcohols. These catalysts were sponteneously separated from the reaction mixtures, and could be subjected to the recycle use for the further reactions. Copyright
