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Separation of Formic Acid/3-Methyl-2-Butanone, Formic

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Separation of Formic Acid/3-Methyl-2-Butanone, Formic Separation of formic acid/3-methyl-2-butanone, formic acid/acetic acid/4-methyl-2-pentanone, formic acid/4-methyl-2-pentanone and m-xylene/o-xylene by extractive distillation by George Bentu A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science in Chemical Engineering Montana State University © Copyright by George Bentu (1990) Abstract: Extractive distillation processes were developed to break the formic acid-3-methyl-2-butanone azeotrope, and the close boiling mixtures of formic acid-4-methyl-2-pentanone, acetic acid-4-methyl-2-pentanone, and m-xylene-o-xylene. Initial screening of potential extractive agents was carried out for each system in an Othmer vapor-liquid equilibrium still. More than one hundred and twenty agents were investigated overall. Subsequent testing of effective agents was carried out in two perforated-plate columns, which after calibration were found to have the equivalent of 3.5 and 7.3 theoretical plates. SEPARATION OF FORMIC ACID/3-METHYL-2-BUTANONE, FORMIC ACID/ACETIC ACID/4-METHYL-2-PENTANONE, FORMIC ACID/4-METHYL-2-PENTANONE AND m-XYLENE/o-XYLENE BY EXTRACTIVE DISTILLATION by George Bentu A thesis submitted in partial fulfillment of the requirements for the degree of Master of Science in Chemical Engineering MONTANA STATE UNIVERSITY Bozeman, Montana October, 1990 i i APPROVAL of a thesis submitted by George Bentu This thesis has been read by each member of the thesis committee and has been found to be satisfactory regarding content, English usage, format, citations, bibliographic style, and consistency, and is ready for submission to the College of Graduate Studies. i W q YLwrI ^ p. Date Chairperson, Graduate Comdiittee Approved for the Major Department Y y / 3 ? ,/? 9 6 TT Date Hdflo, Major Department Approved for the College of Graduate Studies /9 ?o Date :e DeanDeaGraduate STATEMENT OF PERMISSION TO USE In presenting this thesis in partial fulfillment of the requirements for a master’s degree at Montana State University, I agree that the Library shall make it available to borrowers under rules of the Library. Brief quotations from this thesis are allowable without special permission, provided that accurate acknowledgement of source is made. Permission for extensive quotation from or reproduction of this thesis may be granted by my major professor, or in his absence, by the Dean of Libraries when, in the opinion of either, the proposed use of the material is for scholarly purposes. ""Any copying or use of the material in this thesis for financial gain shall not be allowed without my written permission. Signature if Date £7 >/If I $ iv TABLE OF CONTENTS Page BACKGROUND............................................................................................................. I Extractive Distillation.......................................................................................... 5 Azeotropic Distillation......................................................................................... I Selection of Extractive Agent............................................................................... 7 THEORETICAL ASPECTS............................................................................. 10 Thermodynamics of Vapor-Liquid Equilibrium.............................................. -.10 Relative Volatility........................................................................................................ 12 The Fenske Total-Reflux Equation......................................................................... 14 Altering Relative Volatility........................................................................................ 18 Selectivity....................................................................................................................... 18 Factors Affecting Selectivity...................................................................................... 19 Use of Solubility Parameters and Polarity Diagrams........................................... 20 RESEARCH OBJECTIVES............................................................................................ 22 SYSTEMS TO BE SEPARATED........................................................................ 23 Formic Acid/3-Methyl-2-Butanone........................................................................... 23 Formic Acid/Acetic Acid/4-Methyl-2-Pentanone.................................................. 23 Formic Acid/4-Methyl-2-Pentanone............................................................. 24 m-Xylehe/o-Xylene............................................................................... 24 EXPERIMENTAL AND ANALYTICAL EQUIPMENT............. .............................. 27 Othmer Vapor-Liquid Equilibrium Still.................................................................. 27 Perforated-Plate Column.............................................................................. 29 Extractive Agent Recovery........................................................................................ 31 Gas Chromatograph.................................................................................................... 33 EXPERIMENTAL PROCEDURE.................................................................................. 34 Operation of the Othmer Still................................................................................... 34 Calibration of the Perforated-Plate Column.......................................................... 34 Extractive Distillation in the Perforated-Plate Column...................................... 35 V TABLE OF CONTENTS Continued Page RESULTS....................................................................................................................... 38 Formic Acid/3-Methyl-2-Butanone.................................................. 38 Formic Acid/Acetic Acid/4-Methyl-2-Pentanone.................................................... 42 Formic Acid/4-Methul-2-Pentanone......................................................................... 47 m-Xylene/o-Xylene................................................................... .51 .. DISCUSSION................................................................................................................ 56 Data from the Othmer Still..................................................................................... 56 Data from the Perforated-Plate Column................................................................ 57 Viscosity Effect on Tray Efficiency......................... ;........................................ 60 Polarity Diagrams....................................................................................................... 61 s u m m a r y a n d conclusions ..... .......................................................................... 68 RECOMMENDATIONS FOR FUTURE RESEARCH........................................... 69 REFERENCES CITED................................................................................................ 70 . v i LIST OF TABLES Table Page 1. Favorable characteristics of an extractive agent............................................ 8 2. Relative volatility-vs.-theoretical plates-vs.-column cost.......... ....................................................................................... 17 3. Effective agents for formic acid/3-methyl-2-butanone containing sulfolane....................................................... 38 4. Ineffective agents for formic acid/3-methyl-2-butanone............................... 40 5. Effective agents for formic acid/G-methyl-2-butanone using DMSO................................................................... 41 6. Column results for formic acid/3-methyl-2-butanone using sulfolane..........................................'............. 42 7. Column results for formic acid/3-methyl-2-butanone using DMSO................................................................... 42 8. Effective extractive distillation agents for 4-methyl-2-pentanone from formic acid........... ........................................ 43 9. Potential agents containing sulfolane which are ineffective.......... ............ 44 10. Effective extractive distillation agents for 4-methyl-2-pentanone from acetic acid............................................................. 45 11. Ineffective potential extractive agents containing sulfolane for 4-methyl-2-pentanone from acetic acid............................................ 46 12. Column results for formic acid/acetic acid/4-methyl-2-peiitanone using sulfolane................................................... 47 13. Effective agents for formic acid/4-methyl-2-pentanone using DMFA................................................................ 48 14. Effective agents for formic acid/4-methyl-2-pentanone using D M A A ................................................ 48 v i i LIST OF TABLES - Continued 15. Column results for formic acid/4-methyl-2-pentanone using DMAA..................................................... 51 16. Effective agents for m-xylene/o-xylene using esters.................................... 51 17. Column results for m-xylene/o-xylene using esters..................................... , .255 18. Comparison of relative volatility values obtained from the plate column and Othmer still....................................... r*® 19. Solubility parameters at 25®C............... .'....................................................... 63 ! v i i i LIST OF FIGURES Figure Page 1. Fractional distillation column........................................................................
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