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Catalyst in Basic Oleochemicals View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Diponegoro University Institutional Repository Bulletin of Chemical Reaction Engineering & Catalysis, 2(2-3), 2007, 22-31 Catalyst in Basic Oleochemicals Eva Suyenty, Herlina Sentosa, Mariani Agustine, Sandy Anwar, Abun Lie, and Erwin Sutanto * Research and Development Department, PT. Ecogreen Oleochemicals Jln. Pelabuhan Kav 1, Kabil, Batam 29435, Telp/Fax: (0778)711374 Presented at Symposium and Congress of MKICS 2007, 18-19 April 2007, Semarang, Indonesia Abstract Currently Indonesia is the world largest palm oil producer with production volume reaching 16 million tones per annum. The high crude oil and ethylene prices in the last 3 – 4 years contribute to the healthy demand growth for basic oleochemicals: fatty acids and fatty alcohols. Oleochemicals are starting to replace crude oil derived products in various applications. As widely practiced in petrochemical industry, catalyst plays a very important role in the production of basic oleochemicals. Catalytic reactions are abound in the production of oleochemicals: Nickel based catalysts are used in the hydrogenation of unsaturated fatty ac- ids; sodium methylate catalyst in the transesterification of triglycerides; sulfonic based polystyrene resin catalyst in esterification of fatty acids; and copper chromite/copper zinc catalyst in the high pressure hydro- genation of methyl esters or fatty acids to produce fatty alcohols. To maintain long catalyst life, it is crucial to ensure the absence of catalyst poisons and inhibitors in the feed. The preparation methods of nickel and copper chromite catalysts are as follows: precipitation, filtration, drying, and calcinations. Sodium methy- late is derived from direct reaction of sodium metal and methanol under inert gas. The sulfonic based poly- styrene resin is derived from sulfonation of polystyrene crosslinked with di-vinyl-benzene. © 2007 CREC UNDIP. All rights reserved. Keywords: catalyst; hydrogenation; oleochemicals; transesterification 1. Introduction Oleochemicals are starting to replace crude oil Palm plantation shows high growth in the last derived products in various applications. Stearic 10 years. Indonesia has surpassed Malaysia in acid is replacing paraffin wax in candle making, palm oil production for the first time in year 2006. meanwhile natural fatty alcohol replacing synthet- Both countries produce more than 80% of total ics. The relentless climb of palm oil production and world production. Table 1 shows palm oil produc- the recent high crude oil price encourage signifi- tion from 2002 to 2006. With the ever-increasing cant growth of Indonesian basic oleochemicals. palm plantation acreage, the Indonesian palm oil In the early 20th century, the commercial pro- production will continue to increase much faster duction of fatty alcohol was derived from direct than Malaysian. On the other hand, the high crude sodium hydrogenation of sperm oil from whales (1). oil and ethylene prices in the last 3-4 years contrib- Later, many countries listed sperm whales as en- ute to the healthy demand growth for basic oleo- dangered species and banned the importation of chemicals: fatty acids and fatty alcohols . their product derivatives. The fatty alcohol produc- * Corresponding Author. Telp/Fax. (0778)711374 E-mail address: [email protected] (Erwin Sutanto) Copyright © 2007, BCREC, ISSN 1978-2993 Bulletin of Chemical Reaction Engineering & Catalysis, 2(2-3), 2007, 23 Table 1. Palm Oil Production (in thousand tones) 2002 2003 2004 2005 2006 Malaysia 11,908 13,354 13,974 14,961 15,880 Indones ia 9,370 10,600 12,380 14,000 15,900 Others 3,756 3,926 3,586 4,769 5,000 Total 25,034 27,880 29,940 33,730 36,780 Figure 1. The effect of reaction time on the polymerization of acrylonitrile: Reaction condition: 0.5 g exchanged bentonite; acrylonitrile 1.886 mol.dm-3; K2S2O8 0.03 mol.dm-3 at different temperature ers then switched their starting raw materials to oleochemicals and thus enhance their widespread tallow, lard, coconut oil, palm kernel oil, and cas- use. This paper is intended to review the catalytic tor oil. Since the mid 1950s, catalytic hydrogena- process in the production of basic oleochemicals. tion to produce fatty alcohol from natural fats and oils was proved to be more economical and re- 2. Catalytic Process in Basic Oleochemicals placed metallic sodium hydrogenation. 2.1. Unsaturated fatty acid hydrogenation It is plausible to produce fatty alcohol from Saturated fatty acids, naturally exist as direct catalytic hydrogenation of triglycerides. straight chains, do not contain any double bonds However, the catalyst and hydrogen consump- or other functional groups along the chain. tions are higher because by-product glycerin will Whereas unsaturated fatty acids are of similar be simultaneously hydrogenated to produce pro- form, except that one or more alkene functional pylene glycols and propanol. Moreover, glycerin groups exist along the chain, i.e.: each alkene sub- and glycerides were found to be poisonous to the stituting a single bond "-CH2-CH2-" part of the hydrogenation catalyst. The current practice of chain with a double bond "-CH=CH-". Unsatu- fatty alcohol production begins with separating rated fatty acids are naturally found in vegetable the glycerin from fatty acid/methyl ester before oils, including palm oil, palm kernel oil, and soy- hydrogenate the fatty acid/methyl ester further to bean oil . fatty alcohol. The modern manufacturing routes Unsaturated fatty acids are often not desir- of basic oleochemicals are shown in Figure 1. able in a number of fatty acid industrial applica- As widely practiced in petrochemical industry, tions, such as: metal stearates, rubber compound- catalysts also play a very important role in the ing, candles, waxes, and crayons. The presence of production of basic oleochemicals. The invention double bond lowers the melting point and reduces and development of highly selective catalysts of- the shelf-life and heat stability due to vulnerabil- ten improve the economic competitiveness of basic ity of the double bond toward ambient oxidation. Bulletin of Chemical Reaction Engineering & Catalysis, 2(2-3), 2007, 24 To improve the shelf-life and increase the melting point, the unsaturated fatty acids are converted to saturated fatty acids by the relatively simple hydrogenation reaction: 1 2 1 2 R − CH = CH − R − COOH + H 2 ⇔ R − CH 2 − CH 2 − R − COOH A great care on the choice of catalyst, reaction temperature, and reaction pressure should be taken to avoid hydrogen attacking the carboxyl group during the hydrogenation of double bond. The heterogeneous catalyst normally used in the hydrogenation of unsaturated fatty acids is nickel based catalyst. Figure 2 shows process flow diagram of indus- trial scale unsaturated fatty acid hydrogenation. The unsaturated fatty acid is first passed through a dryer, mixed with hydrogen, added with nickel catalyst slurry, and hydrogenated at 25 atm and 453–523 K in a buss loop or slurry reactor. The sulfur, phosphorus, bromine and nitrogen com- pound in the feed should be minimized to below 1 ppm, because they are poisons to the nickel cata- lyst. By product nickel soaps are produced as side In the reaction, a large and branched triglyceride reaction from this process. (TG) is reacted with methanol to produce diglyc- The nickel catalyst is prepared by precipitat- eride (DG) and methyl ester. DG is then reacted ing a nickel salt, usually sulfate or chloride, on an further with methanol to produce monoglyceride inert support, such as silica, alumina, or a combi- (MG) and methyl ester. Finally MG reacts with nation thereof. The precipitate is filtered, washed, methanol to produce glycerol and methyl ester. and dried. The resulting powder is then reduced All the three reaction steps are reversible and at with hydrogen at 753 – 813 K, coated with triglyc- the end of the transesterification reaction usually eride fat, chilled, and formed into pellets (2). a small percentage of MG remain in the product mixture. A process flow diagram of continuous methyl ester production by transesterification is shown in 2.2. Methyl ester by transesterification Figure 3. Natural oils or fats are mixed with ex- The reaction mechanism of transesterification cess methanol and homogeneous alkali-based can be described as follows: Figure 2. Unsaturated Fatty Acid Hydrogenation Bulletin of Chemical Reaction Engineering & Catalysis, 2(2-3), 2007, 25 catalyst at atmospheric pressure and 333 – 338 K homogeneous alkali-based catalyst. Metal alkox- in a continuous stirred tank reactor. Common ide, such as sodium methoxide, is the most effec- catalyst for transesterification is alkali-based (3), tive catalyst for transesterification due to its high due to its higher reactivity than the acid. The alkalinity. Methoxide ion easily attacks triglyc- acid-catalyzed transesterification is normally erides and releases them as methyl ester. three orders of magnitude slower than the alkali. Sodium methoxide is commercially produced Moreover, acid-based catalyst is highly corrosive. from reaction of sodium metal and methanol un- The residence time of reaction mixture in the der inert gas: stirred reactor with homogeneous alkali-based + − catalyst is about 1-2 hours. In order to achieve a 2 Na + 2CH 3OH → 2 Na OCH 3 + H 2 complete transesterification, it is often desirable to have a transesterification plant with two con- Caustic soda and potassium hydroxide can also tinuous stirred reactors in series. provide methoxide ion in methanol solution. How- The use of homogeneous alkali-based catalysts ever, water is generated: limits the choice of feedstock to refined oil with +− very low free fatty acid (FFA) because FFA con- NaOH + CH 3OH → Na OCH 3 + H 2O sumes the alkali based catalyst to produce soap in the glycerin-water. The presence of soap also in- The presence of water interfere transesterifica- creases the glycerin-water viscosity, increases the tion (4). concentration of monoglyceride in the glycerin- Figure 4 shows the typical performance of four water, and complicates the separation of fatty different alkaline catalysts in methanol solution matters from glycerin.
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