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Organosolv Pulping. a Review and Distillation Study Related to Peroxyacid Pulping

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Organosolv Pulping. a Review and Distillation Study Related to Peroxyacid Pulping ORGANOSOLV PULPING ESA A review and distillation study related to peroxyacid MUURINEN pulping Department of Process Engineering OULU 2000 ESA MUURINEN ORGANOSOLV PULPING A review and distillation study related to peroxyacid pulping Academic Dissertation to be presented with the assent of the Faculty of Technology, University of Oulu, for public discussion in Savonsali (Auditorium L 4), Linnanmaa, on June 30th, 2000, at 12 noon. OULUN YLIOPISTO, OULU 2000 Copyright © 2000 Oulu University Library, 2000 Manuscript received 16 May 2000 Accepted 18 May 2000 Communicated by Professor Juhani Aittamaa Doctor Jorma Sundquist ISBN 951-42-5661-1 ALSO AVAILABLE IN PRINTED FORMAT ISBN 951-42-5660-3 ISSN 0355-3213 (URL: http://herkules.oulu.fi/issn03553213/) OULU UNIVERSITY LIBRARY OULU 2000 To Paula and Dijon Muurinen, Esa, Organosolv pulping, a review and distillation study related to peroxyacid pulping Department of Process Engineering, University of Oulu, FIN-90014 University of Oulu, Finland 2000 Oulu, Finland (Manuscript received 16 May 2000) Abstract More than 900 papers related to organosolv pulping have been reviewed in this thesis. From the information included in those papers it can be concluded that organosolv pulping processes are still in a developing stage and are not yet ready to seriously threat the position of the kraft process as the main pulp manufacturing process in the world. Distillation seems to be the main alternative as the process for recovering the solvent in organosolv pulping. A good reason for this is that using simple distillation no potentially harmful components are introduced to the process. The effect of the feed composition on the operation of a separation sequence in an organosolv process using aqueous formic and acetic acids and corresponding peroxyacids was studied. When simple distillation was used as the separation method the effect was found to be significant. The unideal nature of the formic acid-acetic acid-water mixture, the separation of which was studied, makes the ternary composition space divide into four distillation regions. Which region the feed is located in, obviously determines the economy of the distillation sequence. Shortcut calculation methods cannot be recommended for use in designing a distillation sequence for the ternary mixture studied, but they give useful information for the comparison of such sequences. They were used to choose a limited number of alternatives for studies with rigorous calculation methods. Minimum work of separation can also be used to make a satisfying estimate for the relative easeness of separation of the formic acid-acetic acid-water mixture. Thermal integration using pinch technology was also tested and found to be very useful for decreasing the thermal energy consumptions of distillation processes. Thermodynamic efficiencies for separating the formic acid-acetic acid-water mixture by simple distillation were estimated. They were found to be lower than the average value for distillation presented in literature. Keywords: solvent recovery, pinch analysis, formic acid, acetic acid Acknowledgements This research work was carried out in the Mass and Heat Transfer Process Laboratory of the Department of Process Engineering, University of Oulu, Finland, in 1994-1999. I would like to thank my supervisor, Professor Jorma Sohlo, for his encouragement and valuable comments during this research. I want to acknowledge Professor Juhani Aittamaa and Dr. Jorma Sundquist for their review of the thesis and for their useful recommendations. The financial support from Oulun yliopiston tukisäätiö, Jenny ja Antti Wihurin rahasto and Tekniikan edistämissäätiö is gratefully acknowledged. Oulu, May 2000 Esa Muurinen Contents Abstract Acknowledgements Contents 1. Introduction............................................................................................... 13 2. Pulping with organic chemicals.....................................................................16 2.1. Alcohols............................................................................................16 2.1.1. Methanol.................................................................................. 16 2.1.1.1. Catalyzed methanol pulping........................................... 17 2.1.1.2. Methanol in sulphite pulping......................................... 20 2.1.1.3. The ASAM process...................................................... 21 2.1.1.4. Methanol in soda pulping.............................................. 29 2.1.1.5. The Organocell process..................................................31 2.1.1.6. Other alkaline methanol processes................................... 36 2.1.1.7. Methanol lignins..........................................................37 2.1.1.8. Summary....................................................................39 2.1.2. Ethanol.................................................................................... 39 2.1.2.1. Catalyzed and autocatalyzed ethanol pulping..................... 40 2.1.2.2. The Alcell process........................................................49 2.1.2.3. Alkaline ethanol pulping............................................... 57 2.1.2.4. Ethanol in sulphite pulping............................................62 2.1.2.5. Simulation of ethanol pulping........................................63 2.1.2.6. The kinetics and mechanism of delignification................... 64 2.1.2.7. Ethanol lignins............................................................65 2.1.2.8. Summary....................................................................66 2.1.3. Other alcohols........................................................................... 67 2.1.3.1. Propanol and isopropanol...............................................67 2.1.3.2. Butanol...................................................................... 68 2.1.3.3. Glycols...................................................................... 70 2.1.3.4. Summary....................................................................73 2.2. Organic acids...................................................................................... 73 2.2.1. Formic acid............................................................................... 73 2.2.1.1. Pulping and bleaching with formic acid............................ 74 2.2.1.2. The Milox process........................................................75 2.2.1.3. Milox bleaching...........................................................79 2.2.1.4. Solvent recovery in Milox pulping..................................80 2.2.1.5. The chemistry of Milox pulping..................................... 84 2.2.1.6. Summary....................................................................85 2.2.2. Acetic acid................................................................................ 85 2.2.2.1. Acetic acid pulping and bleaching....................................85 2.2.2.2. Peroxyacetic acid..........................................................92 2.2.2.3. Acetosolv pulping........................................................96 2.2.2.4. Acetocell pulping.........................................................99 2.2.2.5. Formacell pulping........................................................99 2.2.2.6. Summary................................................................. 100 2.2.3. Other organic acids................................................................... 100 2.2.4. Salts of organic acids................................................................ 101 2.2.5. Summary................................................................................102 2.3. Phenol and cresols............................................................................. 102 2.3.1. Phenol....................................................................................102 2.3.2. Cresols...................................................................................106 2.3.3. Summary................................................................................108 2.4. Ethyl acetate.....................................................................................109 2.5. Amines and amine oxides....................................................................110 2.5.1. Ethylenediamine.......................................................................110 2.5.2. Hexamethylene diamine............................................................. 111 2.5.3. Methylamine........................................................................... 112 2.5.4. Ethanolamine.......................................................................... 112 2.5.5. Amine oxides...........................................................................113 2.6.6. Summary................................................................................113 2.6. Ketones........................................................................................... 114 2.7. Dioxane...........................................................................................117 2.8. Other organic compounds....................................................................120 2.9. Summary.........................................................................................122 3. Solvent recovery in peroxyacid pulping.........................................................124 3.1. The search for feasible separation methods..............................................125 3.1.1. Wells and Rose.......................................................................
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