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OLEOCHEMICALS Moving downstream There is a wide range of The move downstream from basic more transparent. oleochemicals (oils, fatty acids and But what will your competitive choices for palm oil operators glycerine) to derivatives can seem quite advantage be that will lead customers to wishing to move downstream alluring. It seems as if almost everyone buy from you? Higher product quality, is doing it these days, either through lower costs (perhaps due to a more into oleochemical derivatives. acquisitions or internal development. advanced technology) or perhaps superior What are the most promising Moving into derivatives can lead to new technical service? Perhaps you can fill customers, the capturing of additional demand by being the only manufacturer in products, their applications revenue from existing customers and your country or region. higher utilisation of raw materials. Moving into specialities is also an and the production However, as with any important option. These include pharmaceutical processes involved? decision, especially one that impacts actives and speciality ingredients for on a company’s strategic focus, the cosmetics, among others. The sales of Thomas Blocher ramifications of the decision should be specialities often yield higher margins. thoroughly investigated to avoid, or But while specialities can command properly plan for, possible risks. higher prices, they can often require a higher level of technology, application Myriad choices experience, safety requirements and new There are myriad choices when it comes raw materials. to oleochemical derivatives and deciding Commodities and specialities both have which to produce can be challenging. their advantages and disadvantages and An obvious first step might be to move moving downstream at all carries risks. into downstream commodities such as With this in mind, Buss ChemTech detergent alcohols – these technologies has developed a simplified road map are usually well known and the transition of oleochemical derivatives including to the new technology may not be such some of the products that can be made a big leap. The market size is easier to from palm fatty acids and their related estimate and supply chains can be a little technologies (see diagram above). u 20 OFI – MARCH/APRIL 2020 www.ofimagazine.com OLEOCHEMICALS Narrow range surfactants can be incorporated into alkyl ether sulfates The advantages of palm fatty acids or mixed with other anionic surfactants and exhibit beneficial properties such as reduced irritation to skin/eyes and lower free alcohol content. The catalyst and its method of addition are the key to achieving these narrow range compounds. The catalyst is typically a so-called ‘double metal cyanide’ type - a di-metal compound with a cyano group. Methyl ester ethoxylates (MEE) This special narrow range ethoxylate was seen as a potential low-cost replacement for higher cost fatty alcohol feedstocks. However, the market has not quite lived up to its promise yet. As with other narrow range ethoxylates, the catalyst plays a significant role, including how and when it is dosed. Original players in this area from 1990 were Henkel, Vista and Lion. Today, several others, including some large names in the chemical industry, also have the technology but none is as yet Palm oil serves as an important feedstock for oleochemicals, with Malaysia and known to license the technology. Indonesia being the dominant producers of fatty acids and fatty alcohols in Southeast Asia. EHS considerations Palm oil chiefly comprises palmitic acid C16 (44–45%) and oleic acid, C18:1 (39– Ethoxylation poses some challenges the 40%), along with linoleic acid, C18:2 (10–11%) and a trace amount of linolenic acid, potential producer will need to consider: C18:3. Palm kernel oil (PKO) is characterised by its high level of shorter and medium sourcing EO, the flammability of EO and fatty acid chain lengths (mostly C12 and C14). the regulation of regulated by-products. Over two thirds of oleochemicals derivatives are used in the manufacture of The challenges of sourcing EO are well surfactants. With its ‘two for one’ nature, oil palm is a flexible feedstock for a variety of reported. Naturally, free capacity must products that provides something for practically everyone: the longer fatty-acid chains be found in the quantity and location preferred for liquid detergents or the shorter chains required by surface cleaners. desired. Finding capacity should become And unique in oleochemicals as compared to petrochemicals, the various sources easier with new crackers coming on line. of fatty acids are often interchangeable. With the highest productivity of all crops, oil However, the shipment of EO is highly palm - if suitably (sustainably) managed - makes for one of the most efficient sources of regulated so unless your desired location feedstock for surfactants, one of the most important segments in the chemical industry. is near an EO source, you may find significant challenges. Not only are new truck and rail routes rarely approved, even u Ethoxylates catalyst. The reactor is pressurised with requests from new clients on existing Ethoxylates are non-ionic surfactants nitrogen and heated to about 150°C. routes are often rejected. Thus, potential with applications in numerous markets Typically 2-9 units of EO are added to producers must be prepared to consider including personal care, biotechnology, each alcohol for commodity surfactant or locating their plant near an EO source. pharmaceuticals, oil-well, food, surfactant intermediates. For specialities, EO is extremely flammable and its agriculture, textiles and coatings. other starters can be used and the units mixtures with air are explosive. When They can be used as detergents (in of EO added can reach as high as 100. heated, it may rapidly expand, causing laundry and surface cleaners); emulsifiers A wide range of products are obtained fire and explosion. EO in the presence of (in emulsions, creams and ointments); as a result. The degree of ethoxylation water can hydrolyse to ethylene glycol wetting agents (for adhesives, paints and generally determines the surfactant and form polyethylene oxide, which is coatings and electroplating processes); properties. eventually oxidised by air and leads to dispersants (for pigments and crop hotspots that can trigger to explosive protection and other biocides); stabilisers Narrow range ethoxylates decomposition. Each major technology (emulsion polymers) and as corrosion With conventional catalysts such as supplier has its own safety procedures inhibitors (in metal working fluids). KOH and sodium hydroxide (NaOH), a including nitrogen blanketing and Typical oleochemical compounds that distribution of ethoxymers is obtained. For designing equipment to withstand an are ethoxylated are fatty acids, alcohols, example, if a 9-mole ethoxylate is targeted explosion. amines, polyglycerol esters, triglycerides using a conventional catalyst, a broad As a byproduct of the ethoxylation and sorbitan esters. range of ethoxylates will result, with the process, dioxane can contaminate The sterotypical ethoxylation process degree of ethoxylation being anywhere cosmetics and personal care products involves treating a fatty alcohol with from three to 30 moles of EO. such as deodorants, shampoos, ethylene oxide (EO) and potassium A much tighter distribution can be toothpastes and mouthwashes. It is hydroxyide (KOH) which serves as a obtained with narrow range catalysts. irritating to the eyes and respiratory tract 22 OFI – MARCH/APRIL 2020 www.ofimagazine.com OLEOCHEMICALS and exposure may cause damage to the example, has many uses, among them the central nervous system, liver and kidneys. preparation of substituted imides, amides And since dioxane is highly soluble in ‘Oil palm, if suitably and acid anhydrides, the esterification water, it does not readily bind to soils of alcohols and the synthesis of organic but readily leaches to groundwater. It and sustainably compounds. is also resistant to naturally-occurring An older method to produce fatty acid biodegradation processes. Due to these managed, makes for chlorides is to react dry hydrogen chloride properties, a dioxane plume is often with isopropenyl stearate in solution or much larger than the associated solvent one of the most in the molten state to form high purity plume. Stripping and other methods are stearoyl chloride. The acid chloride is used to reduce the amount of dioxane to efficient sources of formed by the displacement of acetone acceptable levels. from the isopropenyl stearate. feedstock for A more recently developed route Fatty amines commercialised in the past decade is the Another class of oleochemical derivatives chlorination of the fatty acid through a are fatty amines and the chemical surfactants’ reaction with phosgene. This colourless products derived from them. They gas is very toxic but it is a valuable are used in many industries including industrial reagent and building block in cosmetics, mining, agriculture and between the fatty acid and ammonia synthesis of pharmaceuticals and other pharmaceuticals. Fatty amines can be sub- at high temperatures (>250°C) and in organic compounds. classified as nitriles; primary, secondary the presence of a metal oxide catalyst Due to the obvious safety concerns, and tertiary amines; diamines; and (such as alumina or zinc oxide) to give the phosgene is often produced and quaternary ammonium salts. fatty nitrile. The fatty amine is obtained consumed within the same plant. Thus, These last