Soap Hydrolysis

A combination of 2 parts of caustic soda and 1 part of sodium carbonate is often used in single stage boiling. Soda-ash softens the water while interacting with Ca and Mg salts (if such are present) it creates an active reaction of the medium which is most favourable for the formation of stable emulsions and suspensions increases fibre swelling, thus contributing to the release of impurities from the fibre neutralises fatty acids contained in the fabric by soap formation obviates soap hydrolysis in the presence of wool reduces the adherence of detergents to wool in the alkaline medium conditions. 

Fats are hydrolysed to glycerol and fatty acids by boiling with acids and alkalis, by superheated steam and by the action of lipases. If alkalis are used for hydrolysis, the fatty acids combine with the alkalis to form soaps. Alkaline hydrolysis is therefore sometimes called saponification. 

SNG Substitute natural gas. soaps Sodium and potassium salts of fatty acids, particularly stearic, palmitic and oleic acids. Animal and vegetable oils and fats, from which soaps are prepared, consist essentially of the glyceryl esters of these acids. In soap manufacture the oil or fat is heated with dilute NaOH (less frequently KOH) solution in large vats. When hydrolysis is complete the soap is salted out , or precipitated from solution by addition of NaCl. The soap is then treated, as required, with perfumes, etc. and made into tablets. 

The term fat is applied to solid esters of fatty acids with glycerol (glycerides) if the fat is liquid at the ordinary temperature, it is conventionally called a fatty oil, vegetable oil or animal oil. The acids which occur most abundantly are palmitic ticid CH3(CHj),4COOH, stearic acid CH3(CH2)isCOOH and oleic acid CH3(CH2),CH=CH(CH2),C00H. Upon hydrolysis, fats yield glycerol and the alkali salts of these acids (soaps) ... 

Ester hydrolysis in base is called saponification, which means soap making Over 2000 years ago the Phoenicians made soap by heating animal fat with wood ashes Animal fat is rich m glycerol triesters and wood ashes are a source of potassium car bonate Basic hydrolysis of the fats produced a mixture of long chain carboxylic acids as their potassium salts... 

Saponification (Section 20 11) Hydrolysis of esters in basic solution The products are an alcohol and a carboxylate salt The term means soap making and denves from the process whereby animal fats were converted to soap by heating with wood ashes... 

Soaps (Section 19 5) Cleansing substances obtained by the hydrolysis of fats m aqueous base Soaps are sodium or potassium salts of unbranched carboxylic acids having 12-18 carbon atoms... 

Manufacture of Fatty Acids and Derivatives. Splitting of fats to produce fatty acids and glycerol (a valuable coproduct) has been practiced since before the 1890s. In early processes, concentrated alkaU reacted with fats to produce soaps followed by acidulation to produce the fatty acids. Acid-catalyzed hydrolysis, mostly with sulfuric and sulfonic acids, was also practiced. Pressurized equipment was introduced to accelerate the rate of the process, and finally continuous processes were developed to maximize completeness of the reaction (105). Lipolytic enzymes maybe utilized to spHt... 

Hydrolysis cmdes are generally of a better quaHty than soap—lye cmdes with a composition of ca 88% glycerol, <1% ash (Httle or no salt), and <1.5% organic residue. 

Saponification can proceed direcdy as a one-step reaction as shown above, or it can be achieved indirectly by a two-step reaction where the intermediate step generates fatty acids through simple hydrolysis of the fats and oils and the finishing step forms soap through the neutralization of the fatty acid with caustic soda. There are practical considerations which must be addressed when performing this reaction on a commercial scale. 

The quaHty, ie, level of impurities, of the fats and oils used in the manufacture of soap is important in the production of commercial products. Fats and oils are isolated from various animal and vegetable sources and contain different intrinsic impurities. These impurities may include hydrolysis products of the triglyceride, eg, fatty acid and mono/diglycerides proteinaceous materials and particulate dirt, eg, bone meal and various vitamins, pigments, phosphatides, and sterols, ie, cholesterol and tocopherol as weU as less descript odor and color bodies. These impurities affect the physical properties such as odor and color of the fats and oils and can cause additional degradation of the fats and oils upon storage. For commercial soaps, it is desirable to keep these impurities at the absolute minimum for both storage stabiHty and finished product quaHty considerations. 

Commercially, soap is most commonly produced through either the direct saponification of fats and oils with caustic or the hydrolysis of fats and oils to fatty acids followed by stoichiometric (equal molar) neutralization with caustic. Both of these approaches yield workable soap in the form of concentrated soap solutions (- 70% soap). This concentration of soap is the target on account of the aqueous-phase properties of soap as well as practical limitations resulting from these properties. Hence, before discussing the commercial manufacturing of soap, it is imperative to understand the phase properties of soap. 

Fatty Acid Neutralization. Another approach to produce soap is through the neutralization of fatty acids with caustic. This approach requires a stepwise process where fatty acids are produced through the hydrolysis of fats and oils by water, followed by subsequent neutralization with appropriate caustics. This approach has a number of inherent benefits over the saponification process. 

Amidosulfonates. Amidosulfonates or A/-acyl-A/-alkyltaurates, are derived from taurine, H2NCH2CH2S02Na, and are effective surfactants and lime soap dispersants (Table 9). Because of high raw material cost, usage is relatively small. Technically, amidosulfonates are of interest because they are stable to hydrolysis, unaffected by hard water, and compatible with soap. They have been used in soap—surfactant toilet-bar formulations. With shorter, acyl groups, they make excellent wetting agents. 

The main reason for loss of dry in water-borne paints is the hydrolysis of the metal soap. In the presence of water the drier is first hydrated. These hydrates are unstable and result in hydrolysis of the metal soap and subsequently the insolubiUty of the basic metal soap. 

Ba.sic Hydrolysis. Throughout most of history, soap was manufactured by boiling an ester with aqueous alkaU. In this reaction, known as saponification, the ester is hydroly2ed with a stoichiometric amount of alkaU. The irreversible formation of carboxylate anion drives the reaction to completion. 

Hydrolysis by Steam. High pressure steam, 4.5—5.0 MPa (650—725 psi), at 250°C in the absence of a catalyst hydroly2es oils and fats to the fatty acids and glycerol (20). The reaction is commonly carried out continuously in a countercurrent method. The glycerol produced during the reaction is continuously extracted from the equiUbrium mixture with water. A yield of 98% can be achieved. Currentiy, the preferred method to produce soaps is steam hydrolysis of fats followed by alkaU neutrali2ation of the fatty acids. 

Acylglycerols can be hydrolyzed by heating with acid or base or by treatment with lipases. Hydrolysis with alkali is called saponification and yields salts of free fatty acids and glycerol. This is how soap (a metal salt of an acid derived from fat) was made by our ancestors. One method used potassium hydroxide potash) leached from wood ashes to hydrolyze animal fat (mostly triacylglycerols). (The tendency of such soaps to be precipitated by Mg and Ca ions in hard water makes them less useful than modern detergents.) When the fatty acids esterified at the first and third carbons of glycerol are different, the sec-... 

Hydrolysis of animal fats in the presence of strong base leads to glycerol and salts of long-chain carboxylic acids. The latter are known as soaps . 

The catalytic oxidation of long-chain paraffins (C18-C30) over manganese salts produces a mixture of fatty acids with different chain lengths. Temperature and pressure ranges of 105-120°C and 15-60 atmospheres are used. About 60 wt% yield of fatty acids in the range of C12-C14 is obtained. These acids are used for making soaps. The main source for fatty acids for soap manufacture, however, is the hydrolysis of fats and oils (a nonpetroleum source). Oxidation of paraffins to fatty acids may be illustrated as ... 

Ester hydrolysis in basic solution is called saponification, after the Latin word sapo, meaning "soap." As we ll see in Section 27.2, soap is in fact made by boiling animal fat with base to hydrolyze the ester linkages. 

An important reaction of fats is the reverse of ester formation. They hydrolyze, or react with water, just as disaccharides do. Usually hydrolysis is carried out in aqueous Ca(OH)2, NaOH, or KOH solution. Because of long use in the preparation of soap from fats, the alkaline hydrolysis reaction (6) is called saponification. 

Saponification (the hydrolysis of a fat to a soap under strongly alkaline BW conditions)... 

The raw materials for the manufacture of soap, the alkali salts of saturated and unsaturated C10-C20 carboxylic acids, are natural fats and fatty oils, especially tallow oil and other animal fats (lard), coconut oil, palm kernel oil, peanut oil, and even olive oil. In addition, the tall oil fatty acids, which are obtained in the kraft pulping process, are used for soap production. A typical formulation of fats for the manufacture of soap contains 80-90% tallow oil and 10-20% coconut oil [2]. For the manufacture of soft soaps, the potassium salts of fatty acids are used, as are linseed oil, soybean oil, and cottonseed oil acids. High-quality soap can only be produced by high-quality fats, independent of the soap being produced by saponification of the natural fat with caustic soda solution or by neutralization of distilled fatty acids, obtained by hydrolysis of fats, with soda or caustic soda solutions. Fatty acids produced by paraffin wax oxidation are of inferior quality due to a high content of unwanted byproducts. Therefore in industrially developed countries these fatty acids are not used for the manufacture of soap. This now seems to be true as well for the developing countries. 

The reaction of step 2 is carried out by heating the reagents with various acid catalysts, such as orthophosphoric acid or its acid salts, bringing the pH down to 2.3-3.2 [4]. The Igepon A type of surfactant is quite susceptible to hydrolysis, particularly on the alkaline side, as is characteristic for most esters of carboxylic acids. It is therefore used most advantageously at a fairly neutral pH, such as combination soap-syndet toilet bars. 

Stein and Baumann [14] studied the hydrolytic stability of MES and found the hydrolysis rate to be very slow in the pH range of 3-9.5 even at a temperature of 80°C. MES possesses good washing, foaming, and lime soap dispersing properties as well as ready biodegradability and a low acute oral toxicity. 

Some direct dyes are sensitive to reduction or hydrolysis under alkaline conditions, particularly if temperatures above 100 °C are used (section 3.1.3) pH 6 is frequently favoured for stability and this can usually be achieved using ammonium sulphate. A few dyes give optimal results under alkaline conditions, using sodium carbonate or soap the tetra-amino dye Cl Direct Black 22 (12.22) is an example. Whether or not an addition is needed will depend on whether alkali is already present in the commercial brand. 

Twitchell An early process for the acid-catalyzed hydrolysis of animal and vegetable fats for the production of glycerol and soap. The catalyst was a mixture of sulfonated oleic and naphthenic acids and sulfuric acid, known as Twitchell saponifier. Invented in 1897 by E. Twitchell and commercialized by Joslin, Schmidt Company, Cincinnati, OH. The British soapmakers at that time, Joseph Crosfield Sons, did not use it because the products were considered to be too dark in color. 

J. Lucassen, Hydrolysis and precipitates in carboxylate soap solutions, J. Phys. Chem., 70(1966) 1824. 

To purify the soap 20-30 g. are dissolved in boiling water, salted out from the hot solution, and again allowed to solidify. In this way the small amount of alkali in the crude product is removed. The soap, however, remains alkaline to litmus and turmeric papers. The hydrolysis of the quite pure soap is, however, not sufficiently extensive, the concentration of OH-ions not sufficiently large, for phenolphthalein to be coloured. 

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