Oleochemicals fatty acid methyl esters

For most of the further uses oils and fats must be split into the so-called oleochemical base materials fatty acid methyl esters, fatty acids, glycerol and, as hy-... 

Fatty Alcohols. Fatty alcohol is considered a basic oleochemical manufactured by high-pressure hydrogenation of fatty acids or fatty acid methyl esters. The majority of the fatty alcohol produced is further subjected to various processes, such as sulfation, ethoxylation, amination, phosphatization, sulfitation, and others. 

Fats and oils are renewable products of nature. One can aptly call them oil from the sun where the sun s energy is biochemically converted to valuable oleochemicals via oleochemistry. Natural oleochemicals derived from natural fats and oils by splitting or tran -esterification, such as fatty acids, methyl esters, and glycerine are termed basic oleochemicals. Fatty alcohols and fatty amines may also be counted as basic oleochemicals, because of their importance in the manufacture of derivatives (8). Further processing of the basic oleochemicals by different routes, such as esterification, ethoxylation, sulfation, and amidation (Figure 1), produces other oleochemical products, which are termed oleochemical derivatives. 

Fatty acids and fatty acid methyl esters are probably the most important basic oleochemicals in the oleochemical industry. Fatty acids are used as starting materials for soaps, medium-chain triglycerides, polyol esters, alkanolamides, and many more. 

Fatty acid methyl esters play a major role in the oleochemical industry. Methyl esters have increasingly replaced fatty acids as starting materials for many oleo-chemicals. They are used as chemical intermediates for a number of oleochemicals, such as fatty alcohols, alkanolamides, a-sulfonated methyl esters, and many more. One other potential use of methyl esters is as a substitute for diesel oil (14). Methyl esters are clean burning with no sulfur dioxide emission. Although the heat of combustion is shghtly lower, there is no engine adjustment necessary and there is no loss in efficiency. 

Fatty acids, soaps and fatty acid methyl esters are the most extensively used oleochemicals [13]. The free fatty acids are prepared by hydrolysis of oils and fats by alkalis. This procedure named saponification proceeds at high temperature and pressure and leads to crude soaps the acidification of which gives fatty acids. They are subjected to various purification procedures, and finally isolated individually or as mixtures of carboxylic acids of the general formula RCOOH or as soaps RCOOM. The carboxylic acid methyl esters can be produced in two ways by esterification of the isolated carboxylic acid with methanol or by low-temperature... 

Fats and Oils The Raw Materials of Oleochemistry. Fats and oils are triglycerides (i.e., fatty acid esters of glycerol). They are the starting materials for the production of fatty acid methyl esters, which are important intermediates in the production of fatty alcohols and surfactants [198] by the oleochemical route, which has great ecological benefits [199]. The fatty acid methyl esters are produced either by the esterification of fatty acids after hydrolysis of the triglycerides or by direct transesterification with methanol. The overall transesterification reaction is as follows ... 

Another area of major indnstrial importance is the production of oleochemical raw materials such as fatty acids, fatty acid methyl esters, fatty alcohols, and glycerol. The company Henkel is the world s largest processor of renewable fats and oils, with a capacity of 10 t. Tailor-made catalysts are used in most oleochemical reactions. 

The principles of biodiesel synthesis are relatively simple oleochemical reactions (see Chapter 9.1) and have been known and applied for many decades (Figure 8.5)." The basic technology consists in a catalyst induced transesterification of a vegetable oil in a batch, semi-batch or continuous process to create a fatty acid methyl ester (FAME). The catalyst used is a strong base,... 

Recently we have combined two reaction sequences in supercritical media to produce aliphatic fatty alcohol mixtures for the surfactant oleochemical market. This is accomplished by using a transesterification step to synthesize fatty acid methyl esters... 

Oils and fats are also used for non-food purposes, such as the production of motor fuels, in oleochemistry and cosmetics. For these purposes, common edible oils and fats of lower quality are used. Some oils are obtained specifically for technological purposes, such as castor oil or tung oil. A typical example of the use of oils as fuel for diesel engines is the production of fatty acid methyl esters, especially from rapeseed oil. Oleochemicals from oils and fats manufacturing include fatty acids, fatty alcohols and other derivatives for the production of surfactants and subsequently detergents, paints, plastics, adhesives, building materials and many other products. 

Oleochemicals are the primary products or precursors obtained from vegetable oil and animal fats such as fatty acids, methyl esters, alcohols, amides, and glycerol for diverse applications. Rapeseed, castor, and sunflower oil contain C16, Cis long chain fatty acids. They are useful in the production of biopolymers and other adhesives and lubricants. 

Fatty acids, methyl esters and alcohols, as well as many other oleochemicals, are subjected to d. Crude fatty acids fium fat splitting (- hydrolysis) are normally distilled to produce high-quality products that have excellent color and low levels of impurities. Odor bodies and low-boiling unsaponi-... 

C and fatty alcohols when working at 180 °C. Starting from oleic acid methyl ester, yields of up to 84% were obtained. Conversions of oleochemical feedstocks with Rh catalysts were possible, too [45]. 

Raw materials. It is possible to use any fatty acid as a feed material for sulphonation but economic considerations dictate that oleochemical material be preferred. Fatty acids are readily obtained from vegetable and animal oils and fats which are fatty acid triglycerides. These are transesterified to generate glycerol and three moles of a fatty acid ester, normally a methyl ester. The methyl ester can be distilled to give a specific cut and the fatty acid finally isolated by hydrolysis or hydrogenation of the ester. It is common to use animal fats (tallow) in which case the dominant C chains are 16 and 18. 

Reactions converting acids to esters or vice versa and the exchange of ester groups are among the most widely used in fatty acid and hpid chemistry (Figure 4). They find applications from microscale preparation of methyl esters for GC analysis to the industrial production of oleochemicals and biodiesel. The exchange of groups attached to the fatty acid carboxyl is usually an equihbrium process driven to one product by an excess of one reactant or the removal of one product, and it is usually... 

Derivatives of fatty acid from coconut oil are feedstock for a number of diverse nonfood products. Coconut oU fatty acids and glycerol are released by hydrolysis or alcoholysis of the fat. The fatty acids or their methyl esters, which are subsequently fractionated, constimte the starting materials for the oleochemical industry. The byproduct, glycerol, is purified by vacuum distillation. The purified product is, among others, a component of pharmaceutical preparations, an important ingredient in toothpastes, a raw material in the manufacture of nitroglycerol, and the fluid in hydraulic jacks and shock absorbers. 

The use of methyl esters instead of fatty acids as starting materials for many oleochemicals is rapidly gaining ground because of the following advantages (14) ... 

The flow diagram for the production of oleochemicals and some of the derivatives produced is shown in Figure 16 (18). Fatty acids and methyl esters are the main products from which a variety of other derivatives can be manufactured. 

Unsaturated fatty acid esters and oils are very promising and cheap feedstocks for metathesis, which makes the metathesis reaction of interest for the oleochemical industry. The first successful metathesis conversion in this area was the selective transformation of the methyl ester of oleic acid (methyl oleate, methyl cw-9-octadecenoate), a readily accessible unsaturated ester, into equimolar amounts of 9-octadecene and dimethyl 9-octadecene-l,18-dioate, equation (1), using 1-2 mol% of a WCl6/(CH3)4Sn catalyst system at 70°C [3]. 

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