acid anhydride and alcohol

ChemInform Abstract: An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate.. To balance the reaction, each MNBA accepts the atoms of one water molecule from its starting materials, changing itself into two molecules of the amine salt of 2-methyl-6-nitrobenzoic acid, and thus, terminating the reaction. 2.0 TABLE 1 InCl3 (1.1 mmol Conversion of tert-butanol (%) Acetic anhydride They proposed the following reaction mechanism for the acetate ion catalyzed reaction: Catalysis by tertiary amines has been proposed by Fischer (10) to proceed by the base opening the anhydride ring to form an internal salt that then reacts with an epoxide group to yield an alkoxide ester as shown in Reactions 19-20. Inorganic acetates (e.g. This invention provides a process for the selective esterification of a tertiary alcohol(I) represented by a formula: by its reaction with an organic acid anhydride (II) represented by a formula: to produce an organic tertiary ester(III) represented by a formula: wherein, n is an integer having value greater than or equal to 1; R3 is H (hydrogen) or a chemical group selected from the group consisting of halogen, NH2, NO2, OH, SO3H, (preferably hydrogen); and R1, R2, and R4 are organic chemical groups, each comprising both carbon and hydrogen atoms selected from the group consisting of COOH, CnH2n+1, C6H5, (phenyl), substituted phenyl, OCnH2n+1, CnH2n−, OCnH2nC6H5, CnH2n—C6H5, and the like, wherein n is an integer having a value equal to or greater than 1 (preferably selected from methyl, ethyl, propyl, butyl and phenyl groups) using a reusable solid catalyst (IV), represented by a formula: wherein, M is a chemical element selected from Ga (gallium), In (indium), Zn (zinc), Fe (iron) or a mixture of two or more thereof (preferably selected from Ga, In and mixture thereof); Z is a halogen selected from Cl (chlorine), Br (bromine), I (iodine) or a mixture thereof (preferably Cl); y is an integer having a value of 2 or 3, depending upon the valence requirement of M; S is a porous solid support on which MZy is deposited; and c is a loading of MZy on the support, S, expressed as the mmols of MZy deposited per gram of the support, S, in the range from about 0.01 mmol g−1 to about 10.0 mmol g−1 (preferably from 0.02 mmol g−1 to 2.5 mmol g−1); said process comprising: contacting a mixture of (I) and (II) in the absence or presence of a non aqueous solvent with the fine particles of (IV) in a stirred batch reactor provided with a reflux water condenser at atmospheric pressure at the reaction conditions, such that the mole ratio of (II) to (I) is in the range from about 0.1 to about 10.0 (preferably from 0.5 to 2.0); the weight ratio of (IV) to (I+II) is in the range from about 0.005 to about 0.5 (preferably from 0.01 to 0.2); the reaction temperature is below about 80° C. (preferably between 10° C. and 50° C.); and the reaction period is in the range from about 0.1 h to about 50 h (preferably from 0.2 h to 10.0 h); ii) removing the solid catalyst (IV) from the reaction mixture by filtration; and. 0.03 Selectivity for tertiary ester (%) Thus, destabilizing the reactant and stabilizing the product increase the equilibrium constant. 100 30 A large number of chemical groups are known to be present in different organic compounds. The formation of the side products, water and iso-olefin, in the process of this invention is very small relative to the formation tertiary ester (III) and carboxylic acid (V). Acetic anhydride Isobutylene and Decomposition of maleic anhydride as a function of temperature. al., have reported the esterification of tert-butanol by an acid bromide or acid chloride, having formula RCOCl(or Br), wherein R is an organic group, to a tertiary ester having formula RCOOC(CH3)3, using activated basic alumina catalyst with catalyst to tertbutanol and acid bromide or chloride wt/wt ratio of above about 2.0 at room temperature for 9-15 h [Ref. RESULTS OF THE ESTERIFICATION OF T-BUTYL ALCOHOL WITH AN ACID ANHYDRIDE The catalysts given in Tables 1-3were prepared as follows: The InCl3 (1.1 mmol g−1)/Mont K-10 catalyst was prepared by depositing 2.43 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The ZnBr2 (1.1 mmol g−1)/Mont K-10 catalyst was prepared by depositing 2.48 g anhydrous ZnBr2 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The FeCl3 (1.1 mmol g−1)/Mont K-10 catalyst was prepared by depositing 1.78 g anhydrous FeCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The GaCl3 (4.6 mmol g−1)/Mont K-10 catalyst was prepared by depositing 8.1 g anhydrous GaCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The InCl3 (2.3 mmol g−1)/Si—MCM-41 catalyst was prepared by depositing 5.09 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g Si—MCM-41 by incipient wetness technique followed by drying at 120° C. for 8 h. The InCl3, (1.1 mmol g−1)/Mont KSF catalyst was prepared by depositing 2.43 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite KSF clay by incipient wetness technique followed by drying at 120° C. for 8 h. The InCl3 (0.5 mmol g−1)/Mont K-10 catalyst was prepared by depositing 1.11 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The InCl3 (0.02 mmol g−1)/Mont K-10 catalyst was prepared by depositing 0.044 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The GaCl3 (0.5 mmol g−1)/Mont K-10 catalyst was prepared by depositing 0.9 g anhydrous InCl3 (Aldrich) from its acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. The InCl3 (0.5 mmol g−1) and GaCl3 (0.5 mmol g−1)/Mont K-10 catalyst was prepared by depositing the mixture of 1.11 g anhydrous InCl3 (Aldrich) and 0.9 g anhydrous GaCl3 (Aldrich) from their acetonitrile solution on 10 g montmorillonite K-10 clay by incipient wetness technique followed by drying at 120° C. for 8 h. In the incipient wetness technique, the volume of impregnation solution is just sufficient to completely wet solid to be impregnated and there is no free solution in the impregnation mixture.

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