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Reactive Distillation SANDMEYER PRIZE 2003 799 CHIMIA 2003, 57, No.12 Chimia 57 (2003) 799–801 © Schweizerische Chemische Gesellschaft ISSN 0009–4293 Process for the Continuous Production of Fatty Acid Esters via Reactive Distillation Claudia von Scala*, Peter Moritz, and Peter Fässler Sandmeyer Prize Laureates 2003 Abstract: Sulzer Chemtech develops chemical processes in close collaboration with its customers that lead to lower operating and investment costs as well as reduced environmental impact, while at the same time increasing the yield. In this context, innovative technologies and collaboration in global teams play an important role. This is exemplified by the continuous production of fatty acid esters using reactive distillation. Keywords: Esterification · Fatty acid esters · Katapak · Reactive distillation · Sandmeyer Prize Fatty Acid Esters Reactive Distillation Processes of applications can be found in the article of Götze et al. [2]. Furthermore, Sulzer Food, textiles, and cosmetic applications Reactive distillation, i.e. the combina- Chemtech has developed many processes comprise the largest use of fatty acid esters. tion of chemical reaction and distillative using reactive distillation. The scope of Other uses for fatty acid esters are in the product separation in one equipment, offers supply for the reactive distillation technol- processing of rubbers and plastics, metal several advantages over conventional ogy provided by Sulzer Chemtech can in- treatment, synthetic lubricants, and various processes in which the reaction and the clude the process design, pilot tests and test household products. Methyl esters are used product separation are done in series, espe- runs, basic engineering, and the supply of mainly as intermediate raw material for fur- cially for reactions limited by equilibrium Katapak and other distillation column inter- ther chemical conversion into other esters, constraints. As the products in reactive dis- nals. The design of these plants incorpo- amides, ester sulfonates, and fatty alcohols. tillation are continuously separated from rates modern methods for process synthe- Fatty acids, mainly from vegetable the reaction zone, no limiting chemical sis. In addition, Sulzer Chemtech has a sources such as palm trees, soybean, equilibrium can be established and thus the broad know-how and experience in the dis- coconuts, rapeseed or sunflowers, are reaction velocity is maintained at a high tillation of fatty acids, gained during the last mainly produced in the tropical belt, espe- rate, resulting in greater yields. Other ben- 30 years of business in this field. cially in South East Asia, India, China, and efits of reactive distillation can include the Brazil. Processing into fatty acid esters – minimization of side reactions and the uti- esterification – is done mainly in Europe, lization of the heat of reaction for the mass Japan, or the USA. transfer within the same column. Therefore In the esterification reaction, a fatty acid the capital investment and operating costs (e.g. palmitic, myristic, stearic acid) reacts are significantly lower with reactive distil- with an alcohol (e.g. 2-propanol, ethanol, lation than for conventional processes. Ex- butanol, 2-ethyl-1-hexanol) to form the cor- amples for successful applications of reac- respondent fatty acid ester and water. This tive distillation have, among others, been reaction is equilibrium limited, i.e. if at reported for esterifications, etherifications, least one of the products is not removed, the alkylations and isomerizations [1]. conversion will not be complete. Sulzer Chemtech has developed a spe- cial structured catalytic packing, named Katapak, to be used in reactive distillation Fig. 1. Katapak, structured catalytic packing columns (Fig. 1). In this packing, the cata- lyst particles are immobilized between two *Correspondence: Dr. C. von Scala Sulzer Chemtech Ltd. sheets of metal wire gauze. Therefore, con- Conventional Semi-Batch Process P.O. Box 65 ventional catalyst particles can be used, e.g. CH–8404 Winterthur the ones normally recommended by the Esterification of fatty acids with differ- Tel.: +41 52 262 61 41 Fax: +41 52 262 00 68 process or lisense owner. Technical infor- ent alcohols is nowadays mainly performed E-Mail: [email protected] mation of this packing type and further field in a semi-batch mode in large stirred tank SANDMEYER PRIZE 2003 800 CHIMIA 2003, 57, No.12 reactors. A large vessel is filled with the fat- about 100–120 °C. The reactivity of fatty sis. About 15% of the sites were lost be- ty acid mixture to be esterified and heated acids is, however, lower compared with tween the first and the second samples, but up to temperatures above 100 °C. Catalyst shorter acid molecules, and in order to the decrease in reactivity was less intense in is added to the mixture and the whole batch achieve sufficient conversion it was neces- the next samples and stabilized with time. is held at reaction temperature. Alcohol is sary to find solid acid catalysts which are continuously fed to the reaction mixture active in the temperature range of 120–140 and the resulting water is continuously re- °C. By-product formation was also an issue Final Design moved from the column together with the to be considered. A catalyst screening with excess alcohol by a column situated above various potential solid acids was performed In October 2001, after the evaluation of the vessel. Through continuous removal of at the University of Oldenburg, Germany, the pilot tests and based on the process sim- the water produced during the process it is in February 2001. The catalyst chosen was ulation results, the equipment of the plant possible to drive the reaction to completion. a Rohm and Haas cation exchange resin es- was designed. Already by the end of 2001 it At the end the reaction mixture is further pecially developed for the above tempera- was possible to present to the customer an heated and vacuum is applied to remove the ture range. The reaction kinetics were also offer for the production plant. In March excess alcohol and water still present in the determined and used to plan the pilot test 2002, after clarification of the final details, batch. program. the customer ordered the plant, which is While batch processes have the advan- now in the start-up phase. Sulzer Chemtech tage of flexibility in multi-product opera- has also applied for a patent for this pro- tion for small production capacities, their Pilot Tests cess. lower productivity is limiting for larger pro- The total development time of the duction volume. Further disadvantages of After a suitable catalyst was found, the process of less than two years is extremely batch processes are the product quality pilot reactive distillation experiments were short. The development time of similar degradation due to relatively long exposure started in June 2001. In these experiments a processes, from the synthesis in laboratory to heat and the necessity of emptying, part of the future production plant was re- scale to commercial realization, is normal- cleaning and refilling between each batch. produced in small scale to find the optimal ly significantly longer. Through the combi- The catalysts used are normally liquid process conditions and to determine the in- nation of experiences in the field of reac- acids, e.g. sulphuric acid. These acids have fluence of the most important design pa- tion, distillation and membrane technology to be neutralized and separated, generating rameters, like reflux ratio and internal col- a process was realized which has the poten- large amounts of waste products and waste- umn loads on the behaviour of the system. tial to replace in many cases the conven- water. The first pilot tests were performed in a re- tional batch production of fatty acid esters. active distillation column with 50 mm di- ameter at atmospheric pressure. These tests Development of the New Process showed that a higher temperature, i.e. a Process Description higher pressure, in the reactive distillation One of the most important producers column was required. The general tenden- The following description shows the ba- and processors of palm oil and palm oil cies of the system, like the effect of reactant sic principles and suggests a possible pro- products in Malaysia planned to increase its ratio and other distillation parameters, were cess set-up. Depending on (among others) portfolio with fatty acid esters and ap- determined. the raw material composition, the alcohol proached Sulzer Chemtech Singapore in Following the pilot tests at ambient used, the site conditions, and the product the middle of 2000. Sulzer’s idea to devel- pressure, an additional test series was car- specifications, various alternatives can be op a new continuous process with reactive ried out in August 2001 at a higher pressure proposed, fitted to the customer’s individ- distillation utilizing solid catalysts instead (between 3 and 5 bars), with the aim to de- ual requirements. of building a conventional system readily termine the optimal reaction temperature in In this example, the esterification of iso- attracted the attention of the customer. Un- the reactive distillation column. The pro- propyl palmitate with isopropyl alcohol is til now, this technology had not been im- duced ester was distilled and the resulting described (Fig. 2): Palmitic acid (PA) is plemented for the production of fatty acid product was sent to the customer for quali- first reacted with isopropyl alcohol (IPA) in esters. The Malaysian customer was, how- ty analysis. The vapour pressure of the es- a pre-reactor. The pre-reacted stream is then ever, convinced of the potential advantages ter was also determined. All the data pro- introduced into the reactive distillation col- of the technology, so that at the beginning duced in these tests enabled Sulzer Chem- umn, which operates at slight elevated pres- of 2001 he placed an order for the process tech to carry out the scale-up from pilot to sure.
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