Google Scholar, P. Phukan, Tetrahedron Lett. Lett. A. Khalafi-Nezhad, A. Parhami, M.N. follow a several-step procedure designed to isolate the ester product as a pure substance (free from acetic acid and butanol as well as the H 2SO 4 catalyst and H 2O side product). As the reaction proceeds and most of the by-product water is removed from the reaction mixture, the boiling point of the reaction mixture typically increases. RELEASE AND REASSIGNMENT;ASSIGNOR:HARRIS N.A., SUCCESSOR BY MERGER WITH HARRIS TRUST AND SAVINGS BANK;REEL/FRAME:016641/0277, Owner name: M. Ueda, H. Oikawa, J. Org. The reactor is charged with 82 parts of the residue from the previous reaction and an amount of recovered distillate from the previous reaction containing 205 parts of 2-ethylhexanol. Chem. 100 (2000) 1025, K. Tanaka, Solvent-free Organic Synthesis, Wiley-VCH, GmbH and KGaA, Weinheim, 2004, M.S. 1 More particularly, this invention relates to a continuous batch process for preparing esters from mono- or dihydric alcohols and benzoic acid that may contain at least trace amounts of at least one of the three isomeric phthalic acids or phthalic anhydride. This esterification using the benzoic acid and methanol is known as Fisher esterification. PubMed Google Scholar. 4 (2007) 271, A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A. Parhami, A.R. 4 (2007) 229, A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Z.M. https://doi.org/10.1007/BF03245996, Over 10 million scientific documents at your fingertips, Not logged in Ber. 2-ethylhexanol is a preferred monohydric alcohol, based on its cost and availability. J.S. Soc. A distillation was conducted using a reflux ratio of 1:1. 0. When substantially no additional water is collected as a distillate, which typically requires from 1 to about 24 hours, depending upon the amount of benzoic acid reactant, catalyst, number of hydroxyl groups on the alcohol and reaction temperature, distillation of the unreacted alcohol from the reaction mixture is begun. 344 g of methyl benzoate was recovered for the concluding merchandise. Devani, U.S. Pathak, J.R. Patel, Indian. II (1997) 1493. 344g % Output = % Output = Discussion. 54 (1980) 1567. Soc., In press, A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. 70 (2005) 8625. By continuing you agree to the use of cookies. Copyright © 2007 Elsevier Ltd. All rights reserved. In accordance with the law governing equilibrium reactions, removal of the water from the reaction mixture will increase the relative concentration of the desired ester in the reaction mixture. 1437 parts of a distillate containing 99.8 weight percent of the desired ester were collected. A. Khalafi-Nezhad. The unreacted 2-ethylhexanol was distilled from the reaction mixture by heating the contents of the distillation flask to boiling under a pressure of 25 mm mercury. 37 (1971) 3453. The three intermediate reactions yielded 1308.9, 1506.7 and 1476.5 parts by weight, respectively, of a distillate containing over 99.5 percent by weight of the desired ester. Chem. Trans. Lett. Khosropour, K. Esmaeilpoor, A. Moradie, J. Iran. (Power controller setting ~ 6. Nejabat, J. Iran. Chem. PROCEDURE SAFETY PRECAUTIONS - AVOID BURNS--PAY ATTENTION TO WHICH PARTS OF YOUR APPARATUS BECOME HOT. The mixture remaining in the distillation flask from which the ester had been distilled was then allowed to cool, at which time it was combined with the reactants used in the next esterification reaction. ► CALB lipase is deactivated by both temperature and benzoic acid. Soc., Perkin. Chem. The acid catalysed reaction between benzoic acid and methanol may be represented as: This esterification using the benzoic acid and methanol is known as Fisher esterification. 0.0236 2 Babu, M. Mittal, Tetrahedron 57 (2001) 7047. K. Wakasugi, A. Nakamura, Y. Tanabe, Tetrahedron Lett. V.K. The failure of the prior art to teach distillation of esters derived from aromatic acids and alcohols containing more than about 6 carbon atoms in the absence of steam suggests that conventional distillation of these esters is not feasible, particularly on a commercial scale, even under reduced pressures. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran, A. Khalafi-Nezhad, A. Parhami & A. R. Moosavi Zare, Department of Chemistry, Payame Nour University of Bushehr, Bushehr, 1698, Iran, You can also search for this author in The reaction between benzoic acid and the alcohol(s) is conducted in a reactor equipped with means for heating the contents at least to the boiling point, under atmospheric pressure, of the alcohol used as one of the reactants. When the vapor temperature reached 182° C. the first phase of the distillation was discontinued. Some of these undesired products may impart color to the residue. 3 B. Castro, G. Evin, C. Selve, R. Seyer, Synthesis (1977) 413. Collection of the desired ester is begun when the vapor temperature reaches the boiling point of this ester. 2 (2005) 319, M.R. Trans. Zahedi, H. Abbasi, K. Tabar-Heidar, J. Iran. Unreacted Benzoic Acid (parts) 0.2008 In these conditions, the most active lipase among those tested for this synthesis was lipase B isozyme from Candida antarctica (CALB), obtaining conversion values higher than 80% and a significant selectivity to α-MBG. BA The boiling points of benzoic acid esters prepared using the present method are typically from 50 to 300 degrees C. under pressures of from 1 to 100 mm. Brown, F. Rajabi, J. Iran. S. Hashimoto, I. Furukawa, Bull. Shah, K.M. The heating times, amounts of water collected during each of the three reactions and the amount of unreacted benzoic acid remaining following the reactions are recorded in Table 1. 62 (1989) 539, P.A. ► Stability of CALB differs depending on the activity of interest: hydrolytic or synthetic. Nejabat, Synth. The chemical reaction for esterification is given below. Swirl to mix the reactants, add 2-3 boiling stones, attach a condenser, and heat the mixture at reflux for 1 hour. Volokna (1975) (4) 27-8. 0.0000 Suitable dihydric alcohols for use in the method of the present invention, based on their cost and availability, include but are not limited to ethylene glycol, propylene glycol, 1,4-butanediol and 1,6-hexanediol. As discussed in the preceding section with relation to reaction residues, the amount of recovered alcohol withheld is sufficient to establish a steady state concentration of impurities in the benzoic acid ester produced during succeeding reactions of a series. Assigned to VELSICOL CHEMICAL LLC (F/K/A VELSICOL CHEMICAL CORPORATION, VELSICOL CHEMICAL LLC (F/K/A VELSICOL CHEMICAL CORPORATION. The reaction is tolerant of varying substitution patterns on both the benzoic acid and phenol components. The enzymatic reaction of benzoic acid and glycerol in the absence of organic solvents to obtain the 1- or 3-monobenzoate glycerol (α-MBG) is studied. Katritzky, C.O. 0.1916 Moosavi Zare, A. Parhami, J. Iran. The Combined Chemical Dictionaries on CD-ROM, Version 6.1, Chapman and Hall, 2003. 46 (2005) 147, H. Ito, T. Tada, M. Sudo, Y. Ishida, T. Hino, K. Saigo, Org. The ratio of volume of liquid collected to that returned to the reactor is referred to as the reflux ratio. Place 10.00 g of benzoic acid and 25 mL of methanol in a 125 mL round bottomed flask, and carefully pour 3.0mL of concentrated sulfuric acid down the walls of the flask. The advantage of titanium compounds is their stability, which allows the catalyst to be recycled and used in up to 4 or more successive reactions with no significant loss of catalytic activity, and their high boiling point, which ensures that the catalyst will not distill together with the desired ester. 42 (1980) 163. Adams, J.R. Lewis, J.G. Chem. Chem. Acta 61 (1975) 1675. J.E. - 67.225.241.229. 3.30 H. Eshghi, M. Rafei, M.H. Chem. Percent of Total Peak Areas 2. HARRIS TRUST AND SAVINGS BANK, AS AGENT, ILLINOIS, Free format text: Chiriac, Rev. The unreacted alcohol recovered by distillation during a previous esterification reaction can be used as a portion of the alcohol for a subsequent reaction. Part of Springer Nature. 0.0000 Because this type of esterification is usually an equilibrium reaction, to favor formation of the desired ester a stoichiometric excess of the alcohol reactant is typically used and the water formed as a by-product is continuously removed. We believe this methodology will … Esterification runs were batch wise performed with a concentration of enzyme of 30 g/L, changing the initial concentration of the acid in glycerol from 20 to 60 g/L, and temperature from 50 to 70 °C. TABLE 1 Place 10.00 g of benzoic acid and 25 mL of methanol in a 125 mL round bottomed flask, and carefully pour 3.0mL of concentrated sulfuric acid down the walls of the flask. Imanzadeh, A. Khalafi-Nezhad, A. Zare, A. Hasaninejad, A.R.

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