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Extraction of Aromatics from Naphtha with Ionic Liquids

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Extraction of Aromatics from Naphtha with Ionic Liquids Ionic Liquids 28-07-2005 14:51 Pagina 1 Extraction of Aromatics from Naphtha with Ionic Liquids from Aromatics of Extraction Uitnodiging Ionic liquids are organic salts that are liquid at low temperatures From Solvent Development (<100 °C) and consist of large organic cations and anions such as Hierbij wil ik u van harte uitnodigen to Pilot RDC Evaluation tetrafluoroborate, chloride, etc. The application of ionic liquids for voor het bijwonen van de openbare verdediging van mijn proefschrift, extraction processes is promising because of their non-volatile getiteld nature. The ionic liquid [mebupy]BF4 is suitable as an extractant for aromatic hydrocarbons from aliphatic hydrocarbons and was Extraction of Extraction of selected for tests in a pilot scale Rotating Disc Contactor (RDC). The pilot plant RDC provided good results: small droplets and a Aromatics from high column capacity. Naphtha with An economic evaluation was made for the separation of toluene Aromatics from from a mixed toluene/heptane stream with [mebupy]BF4 and Ionic Liquids compared to the extraction with sulfolane. The total investment costs in the sulfolane process were about M€ 86 for a naphtha Naphtha with op vrijdag 9 september 2005 feed of 300 ton/hr, containing about 10% aromatic hydrocarbons. om 15:00 uur The process with the ionic liquid was estimated to be M€ 56, in zaal 2 van gebouw de Spiegel van de Universiteit Twente. including an ionic liquid inventory of M€ 20. The main conclusion of the process evaluation is that development of ionic liquids which Ionic Liquids Voorafgaande aan de verdediging zal ik om 14:45 uur een korte inleiding geven show a high aromatic distribution coefficient with a reasonable Geert Wytze Meindersma over de inhoud van dit proefschrift. aromatic/aliphatic selectivity could reduce the investment costs of Na afloop van de promotie is er een the aromatic/aliphatic separation to about M€ 25 to 30. receptie op dezelfde lokatie. Wytze Meindersma tel. 053 489 2607 Geert Wytze Meindersma [email protected] Paranimfen: Anita Podt [email protected] Bill de Rave ISBN 90-365-2231-5 [email protected] STELLINGEN behorende bij het proefschrift EXTRACTION OF AROMATICS FROM NAPHTHA WITH IONIC LIQUIDS FROM SOLVENT DEVELOPMENT TO PILOT RDC EVALUATION Geert Wytze Meindersma, Universiteit Twente (09-09-2005) 1. Het gebruik van activiteitscoëfficiënten bij oneindige verdunning om de verdelingscoefficiënt en de selectiviteit voor extractie te bepalen, geeft bij normale concentraties geen exact beeld van de waarden van deze parameters, hooguit een indicatie. Dit proefschrift, hoofdstuk 4. 2. Door de bijna oneindige variatie in kat- en anionen van ionische vloeistoffen zouden er theoretisch 1018 verschillende ionische vloeistoffen zijn. Deze enorme verscheidenheid heeft echter in de praktijk weinig nut. Dit proefschrift, hoofdstuk 4. 3. Aan het begin van elk project in toegepast onderzoek dient een ruwe economische evaluatie van mogelijke procesroutes plaats te vinden om aan te geven in welke richting het onderzoek dient te gaan. Dit proefschrift, hoofdstukken 1, 2 en 7. 4. Veel onderzoekers gaan uit van een “me-too” houding, zo ook bij onderzoek op het gebied - van ionische vloeistoffen, waar velen nog steeds werken met PF6 -houdende ionische vloeistoffen, terwijl aangetoond is dat hiermee HF-vorming kan plaatsvinden. Dit proefschrift, hoofdstuk 4. 5. Bij de selectie van een ionische vloeistof als extractant voor de aromaat/alifaat scheiding is de verdelingscoefficiënt van de aromaat veel belangrijker dan de aromaat/alifaat selectiviteit om tot redelijke apparaatdimensies te komen. Dit proefschrift, hoofdstuk 7. 6. Onderzoekers presenteren de resultaten van hun onderzoek naar nieuwe methoden dikwijls als positief, waar conventionele methoden betere, hetzij effectievere, hetzij economisch interessantere, resultaten opleveren. Dit proefschrift, hoofdstukken 4 en 6. 7. “Papier is geduldig” is een uitdrukking die ook in de wetenschap van toepassing is. 8. Veel Nederlandse politici hebben zich niet gerealiseerd dat de in de Londense Underground hoorbare waarschuwing “mind the gap between the train and the platform” volledig op hen van toepassing is. Opgetekend op 2 juni 2005, na de uitslag van het Europese Referendum. 9. Een minister van Onderwijs, Cultuur en Wetenschap, die terecht opmerkt dat met de huidige stand van de wetenschap niet alle vragen beantwoord kunnen worden, dient onafhankelijk fundamenteel onderzoek te bevorderen en geen populistisch debat over “intelligent design” aan te zwengelen. Opgetekend in mei 2005. PROPOSITIONS belonging to the thesis EXTRACTION OF AROMATICS FROM NAPHTHA WITH IONIC LIQUIDS FROM SOLVENT DEVELOPMENT TO PILOT RDC EVALUATION Geert Wytze Meindersma, University of Twente (09-09-2005) 1. The use of activity coefficients at infinite dilution for the determination of distribution coefficients and the selectivity at extraction does not produce accurate values of these parameters at normal concentrations, but gives at most an indication thereof. This thesis, chapter 4. 2. There are claimed to be 1018 possible combinations in ionic liquids, because of the endless possible variation of the cations and anions, but this variety has little usefulness in practice. This thesis, chapter 4. 3. A crude economic evaluation of possible process routes in applied research should be carried out at the start of each project in order to indicate in which direction the research should go. This thesis, chapters 1, 2 and 7. 4. Many researchers have a “me-too” attitude, also true in the ionic liquid field, where a lot of - them still use PF6 -containing ionic liquids, while it has been shown that HF formation is quite probable with these ionic liquids. This thesis, chapter 4. 5. The aromatic distribution coefficient has a much larger impact than the aromatic/ aliphatic selectivity in selecting an ionic liquid for aromatic/aliphatic separations in order to arrive at reasonable dimensions for the equipment. This thesis, chapter 7. 6. Researchers often present the results of their project in a positive way, while conventional methods sometimes produce better results with respect to effectiveness or economics. This thesis, chapters 4 and 6. 7. “Paper won’t blush” is an expression which is also applicable in science. 8. Many Dutch politicians do not realise that the announcement in the London Underground “mind the gap between the train and the platform” completely applies to themselves. Written down on June 2, 2005, after the Dutch European Referendum. 9. A Secretary of Education, Culture and Science, who rightly remarks that with the current state of science not all questions can be answered, should promote fundamental research and should not initiate a popular debate on “intelligent design”. Written down in May 2005. From Solvent Development to Pilot RDC Evaluation Extraction of Aromatics from Naphtha with Ionic Liquids Promotiecommissie Voorzitter Prof. dr. ir. A. Bliek Universiteit Twente Promotor Prof. dr. ir. A.B. de Haan Universiteit Twente Assistent-promotor Dr. ir. N.J.M. Kuipers Universiteit Twente Leden Prof. dr.-Ing. M. Wessling Universiteit Twente Prof. dr. ir. J.A.M. Kuipers Universiteit Twente Prof. dr. ir. J.T.F. Keurentjes Technische Universiteit Eindhoven Dr. ir. C.J. Peters Technische Universiteit Delft Prof. dr. M.P. Atkins Imperial College, London, UK The research in this thesis was funded by DSM Research bv, Geleen, The Netherlands and by SenterNovem (project 344150/3401). Extraction of aromatics from naphtha with ionic liquids From solvent development to pilot RDC evaluation Meindersma, G.W. Thesis, University of Twente, The Netherlands ISBN 90-365-2231-5 Cover design: Jo Molenaar, [deel 4] ontwerpers, Enschede Printed by Febodruk, Enschede Copyright © G.W. Meindersma, Enschede, 2005 All rights reserved. EXTRACTION OF AROMATICS FROM NAPHTHA WITH IONIC LIQUIDS FROM SOLVENT DEVELOPMENT TO PILOT RDC EVALUATION PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Universiteit Twente, op gezag van de rector magnificus, prof.dr. W.H.M. Zijm, volgens besluit van het College van Promoties in het openbaar te verdedigen op vrijdag 9 september 2005 om 15.00 uur door Geert Wytze Meindersma geboren op 4 augustus 1947 te Tilburg Dit proefschrift met bijbehorende stellingen is goedgekeurd door de promotor Prof. dr. ir. A.B. de Haan en de assistent-promotor Dr. ir. N.J.M. Kuipers VOORWOORD De klassieke openingszin luidt: “Het is af!!”. Dit proefschrift is nu, gelukkig, inderdaad af, maar het werk aan ionische vloeistoffen nog lang niet. Als alles gaat zoals we verwachten, wordt het onderzoek voortgezet. Dit proefschrift was niet tot stand gekomen zonder hulp, aanwijzingen, raad en aansporingen van anderen. Allereerst wil ik mijn promotor André de Haan bedanken voor het feit dat hij voor mijn aanstelling aan de UT heeft gezorgd en voor de grote vrijheid van handelen die ik tijdens het promotieonderzoek heb genoten. Zijn kritiek was steeds opbouwend en stimulerend. Norbert Kuipers wil ik graag bedanken voor het kritisch doorlezen van diverse hoofdstukken, waarbij hij vele waardevolle suggesties heeft gedaan, die het geheel hebben verbeterd. De gehele vakgroep Scheidingstechnologie was en is heel gezellig: er heerst een goede en collegiale sfeer en ik hoop dit nog enige jaren te kunnen meemaken. Daarvoor bedank ik van harte de promovendi Karin, Fahong, Boris, Johan, Bart, Maartje, Jeroen (ook voor het beantwoorden van mijn vragen op computergebied), Thijs, Maksym, Daleen, Renze, Katarina, Paul, Lara, Tanja, Meritxell,
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