6963-44-6Relevant academic research and scientific papers
Lipase-mediated selective acetylation of primary alcohols in ethyl acetate
de Souza, Ernane C.,Romero-Ortega, Moises,Olivo, Horacio F.
supporting information, p. 287 - 290 (2017/12/29)
An environmental friendly process to selectively acetylate primary alcohols was demonstrated. The esterification process consists of treatment of a primary alcohol in the presence of immobilized C. antarctica lipase (Novozyme-435) in ethyl acetate at room temperature. Primary alcohols were acetylated in the presence of secondary alcohols and phenols.
Design of a highly active silver-exchanged phosphotungstic acid catalyst for glycerol esterification with acetic acid
Zhu, Shanhui,Gao, Xiaoqing,Dong, Fang,Zhu, Yulei,Zheng, Hongyan,Li, Yongwang
, p. 155 - 163 (2013/09/02)
A series of highly active, selective, and stable silver-exchanged phosphotungstic acid (AgPW) catalysts were prepared, characterized, and evaluated for bio-derived glycerol esterification with acetic acid to produce valuable biofuel additives. The structures, morphologies, acidities, and water tolerance of these samples were determined by FTIR, Raman, XRD, SEM-EDX, FT-IR of pyridine adsorption, and H2O-TPD. Several typical acidic catalysts were also performed for comparison. Among them, partially silver-exchanged phosphotungstic acid (Ag1PW) presented exceptionally high activity, with 96.8% conversion within just 15 min of reaction time and remarkable stability, due to the unique Keggin structure, high acidity as well as outstanding water-tolerance property. A plausible reaction mechanism was also proposed. In addition, this Ag1PW catalyst exhibited universal significance for esterification, holding great potential for a wide range of other acid-catalyzed reactions.
Iron(III) tosylate catalyzed acylation of alcohols, phenols, and aldehydes
Baldwin, Neil J.,Nord, Anna N.,O'Donnell, Brendan D.,Mohan, Ram S.
, p. 6946 - 6949 (2013/01/15)
Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.
Polystyrene-supported GaCl3: A new, highly efficient and recyclable heterogeneous Lewis acid catalyst for acetylation and benzoylation of alcohols and phenols
Rahmatpour, Ali
, p. 1048 - 1054 (2013/02/22)
A new, simple and highly chemoselective method for both acetylation and benzoylation of alcohols and phenols with acetic anhydride in the presence of polystyrene-supported gallium trichloride (PS/GaCl3) as a highly active and reusable heterogeneous Lewis acid catalyst is presented. In this catalytic system, primary, secondary and tertiary alcohols as well as phenols were converted to the corresponding acetates and benzoates with high yields. The heterogenized catalyst is of high reusability and stability in the acetylation reactions and was recovered several times with negligible loss in its activity or a negligible catalyst leaching, and also there is no need for regeneration. Remarkably, a selective mono-acetylation of symmetrical diols can be achieved chemoselectively by employing the same catalyst.
Organocatalytic chemoselective monoacylation of 1,n-linear diols
Yoshida, Keisuke,Furuta, Takumi,Kawabata, Takeo
supporting information; experimental part, p. 4888 - 4892 (2011/06/22)
Matters of length: Exclusive or predominant monoacylation of 1,n-linear diols took place in the presence of 1 when the chain length of linear diols was equal to or shorter than five carbon atoms. The chemoselectivity of acylation between 1,5-pentanediol (n=5) and 1,6-hexanediol (n=6) was 5.2, and that between 1,5-pentanediol and its monoacylate was 113. Copyright
Synthesis and reactivity studies of a new reagent, ethyltriphenylphosphonium tribromide
Jamir, Latonglila,Alimenla,Kumar, Anil,Sinha, Dipak,Sinha, Upasana B.
experimental part, p. 147 - 155 (2011/03/17)
A new reagent, ethyltriphenyl phosphonium tribromide (ETPPTB), has been synthesized and studied. Results show that the reagent is quite efficient for various reactions such as organic bominations, acylations, and isothiocyanate preparation. Copyright
Simple and efficient method for acetylation of alcohols, phenols, amines, and thiols using anhydrous NiCl2 under solvent-free conditions
Meshram, Gangadhar,Patil, Vishvanath D.
experimental part, p. 4384 - 4395 (2010/04/29)
Solvent-free acetylation of alcohols, phenols, amines, and thiols with acetic anhydride (Ac2O) in the presence of 0.1mol% (13mg) anhydrous NiCl2, an inexpensive and easily available catalyst, is described. Excellent yields, short reaction time, and mild reaction conditions are important features of this method.
A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3·6H2O as a catalyst under solvent-free conditions
Reddy, T. Srikanth,Narasimhulu,Suryakiran,Mahesh, K. Chinni,Ashalatha,Venkateswarlu
, p. 6825 - 6829 (2007/10/03)
A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers excellent yields of the mono acetates of 1,3-, 1,4- and 1,5-diols.
Cobalt(II)-catalyzed direct acetylation of alcohols with acetic acid
Velusamy, Subbarayan,Borpuzari, Sarbani,Punniyamurthy
, p. 2011 - 2015 (2007/10/03)
Cobalt(II) chloride hexahydrate (CoCl2·6H2O) efficiently catalyzes the acetylation of alcohols with AcOH in high yields. This protocol is also effective with other carboxylic acids, trifluoroacetic acid, propanoic acid, phenylacetic acid and benzoic acid, affording the corresponding acylated products in moderate to good yields. Removal of water is not necessary in these reactions. The catalyst can be filtered and recycled without loss of activity.
Lipase-catalysed selective monoacylation of 1,n-diols with vinyl acetate
Framis, Victoria,Camps, Francisco,Clapés, Pere
, p. 5031 - 5033 (2007/10/03)
A simple enzymatic methodology for the selective monoacetylation of 1,n-diols (n=5,8) using vinyl acetate is reported. Monoacetylation excesses of 81-87% at 74-90% 1,n-diol conversions were obtained in toluene and diisopropyl ether using Thermomyces lanuginosus lipase (TLL) immobilised on polypropylene powder as catalyst.
