1. http://chemistry.about.com/library/weekly/blsapon.

htm

Soap and Saponification

Preparation & Chemical Structure One of the organic chemical reactions known to ancient man was the preparation of soaps through a reaction calledsaponification. Natural soaps are sodium or potassium salts of fatty acids, originally made by boiling lard or other animal fat together with lye or potash (potassium hydroxide). Hydrolysis of the fats and oils occurs, yielding glycerol and crude soap.
Related Resources Acids and Bases CHEM 101 Chemistry Glossary How Does Soap Clean? How to Make Soap

In the industrial manufacture of soap, tallow (fat from animals such as cattle and sheep) or vegetable fat is heated with sodium hydroxide. Once the saponification reaction is complete, sodium chloride is added to precipitate the soap. The water layer is drawn off the top of the mixture and the glycerol is recovered using vacuum distillation.

2. http://www.digipac.ca/chemical/mtom/contents/chapter3/making_soap.htm

Making Soap
Perhaps a little over one hundred years ago, commercial soap did not exist. Soap was made in the kitchens of houses across the world. The preparation of soap is a simple job, but illustrates an important difference between science and technology. Soap can be made from a strong base and fat. In days gone by, the strong base was often created by gathering the ashes from wood fires. These ashes contain large quantities of potassium hydroxide (and since the ashes were collected under the pots in the kitchen, potassium hydroxide became known as potash, though today the word potash usually refers to potassium chloride). The fat was usually animal fat, for example bacon grease, or melted beef fat (tallow). When boiled together the product was soap. Doubtlessly, one of our pre-historic ancestors discovered this reaction when animal fat, rendered from meat cooking over an open fire, fell into the ashes. Later on, the potash was replaced by lye (sodium hydroxide). Though our ancestors knew the technology, they did not know or understand the science of the chemistry involved. Fats and oils are chemically the ester of an organic acid and glycerol. They are known as triglycerides, since they have three fatty acid molecules attached to each of the carbons in the glycerol skeleton. The reaction between a strong base and a fat is called saponification, and can be represented by the following chemical reaction between olive oil and sodium hydroxide:

Because the hydroxides are quite hard to clean completely from the soap, the soap remained fairly corrosive. Doing large quantities of laundry would cause severe irritation to the skin. Upper class people did not do laundry. Instead, it was done by the poor and downtrodden in society widows or deserted women who "took in

washing", and at certain times in North America in particular, by the Chinese. These poor people often had no other source of income. Soap is not used a lot anymore. Because the science behind soap making is known we understand what is taking place with the atoms and molecules when we make soap we have been able to produce better technological products. Most of the cleaning agents we call soaps are really detergents. Detergents have the same characteristic property as soap that is they let water attach to oil and grease molecules but are much less affected by hard water. You will use a variation of this ancient procedure in this lab in which you make a small quantity of soap by the reaction of sodium hydroxide and vegetable oil.

Caution
Sodium hydroxide is extremely corrosive and will cause intense burns to the skin or eyes. Wear eye protection at all times while doing this experiment. If you should spill any on your skin, wash immediately with large quantities of cold water, and report the incident to your teacher.

Materials:

about 2 mL of vegetable oil, or 1.5 g of fat about 15 mL of a 50-50 mixture of ethanol and water containing approximately 15 g of solid NaOH in every 100 mL of solution 2 - 18 x 150 mm test tubes solid stirring rod 400 mL beaker about 3/4 full of hot water Bunsen burner, ring stand, and gauze mat, or electric hot plate 50 mL beaker ice water (about 50 mL) wire screen, or cheesecloth gauze

Procedures: 1. Put the fat or oil into the test tube. Different fats will give different products. Members of the class may wish to experiment with different fats or oils to see the characteristics of the resulting soaps. The advantage of using a vegetable oil is that it

is more obvious when you have produced soap, since the product will be in the solid state. 2. Pour in about 10 mL of the alcohol-water-NaOH mixture. 3. Set up a hot water bath (either place the 400 mL beaker and water on a stand over a Bunsen burner, or use an electric hot plate). Stand the test tube and its contents in the hot water bath. Heat the water to boiling, and keep it boiling gently. 4. Stir the mixture in the test tube every few minutes. CAUTION: be extremely careful doing this. The soap that is produced will cause the products to foam. If stirred too fast the soap and hydroxide can foam out of the test tube, and potentially cause serious chemical burns. If this happens, IMMEDIATELY remove the stirring rod and wait for the reaction to slow down. As it is heated, the ethanol will evaporate. Add more of the alcohol-water-NaOH mixture periodically, to maintain an approximately constant level of liquid in the test tube. Heat and stir for about 15 minutes. While doing this, get a test tube about 3/4 full of saturated NaCl brine solution, and put it into your hot water bath as well. 5. After heating, remove the test tube with the soap mixture from the water bath (use a clamp on the test tube so that you do not burn yourself). Pour the solution into the 50 mL beaker. As the mixture cools, you should see soap forming as a waxy layer. Break this up with your stirring rod. Pour the hot brine solution into the now empty test tube, then add it to the contents of the beaker. Use your stirring rod to clean as much of the soap as possible from the test tube. 6. Decant the soap using a wire screen or cheesecloth to keep from losing small particles of soap. Wash the soap at least twice with 20 mL portions of ice water. After the last washing, pour the soap out onto several layers of paper towel, and blot as much water from it as you can. Allow the soap to dry. Note: you will probably detect the corrosiveness of your soap from its effect on the paper. If the paper towel turns brown, this is due to the reaction of the residual NaOH left in your soap. 7. Put a small piece of your soap into a test tube containing distilled water, a similar piece into a test tube containing tap water, and a third into a test tube of artificial hard water (can be prepared by dissolving 0.2 g of CaCl2 in 1 L of water). Shake each tube vigorously and record the results. Repeat this same procedure with about the same amount of a commercial soap. Note and record any differences. It is not a good idea to use this soap for washing your hands. Unless you wash it thoroughly, and/or neutralize any remaining NaOH with an acid, the soap is likely to be very corrosive.

3. http://summerbeemeadow.com/content/properties-soapmaking-oils

Properties of soap making oils

What makes different oils different?

On Soap, Oils and Fatty Acids...

Soap is a chemical substance, created by combining fatty acids, an alkali and heat in a water medium. Fatty acids are chemical components of oils ("oils" includes fats and butters, too). There are various fatty acid varieties, each differing in molecular composition. When used in soapmaking, each fatty acid variety will make a soap that has its own unique characteristics. Different oils used in soapmaking have differing proportions of these various fatty acids. Therefore, chosen "recipe" combinations of specific oils mixed together in soapmaking can result in combined fatty acids compositions tailored to make soaps with desired characteristics. An understanding of this ability to tailor our oils mix and thereby control our fatty acids mix is essential in designing successful soap recipe formulas. I know this is a rather "heavy" paragraph, but please read it carefully as understanding this is crucial to being able to best use the information presented below.

Some Fatty Acids and their Resulting Soap Characteristics:

Lauric Acid: Linoleic Acid: Myristic Acid: Oleic Acid: Palmitic Acid: Ricinoleic Acid: Stearic Acid: Hard bar, excellent cleansing, lots of fluffy lather, can be drying to skin Conditioning, silky feel Hard bar, cleansing, fluffy lather Conditioning, slippery feel, stingy lather, kind to skin Hard bar, cleansing, stable lather Softer bar, conditioning, moisturizing, lots of fluffy, stable lather, kind to skin Hard, long lasting bar, stable lather

Some notes on using this information:

Note that a given oil can have a fairly wide range of percentages of any constituent fatty acid and can be somewhat different from different sources. The fatty acids composition information below is indicative of the properties of each oil listed and of soap made from that oil, but know that oils

formulation for soapmaking is an art and not an exact science. Each oil will also have a percentage of "non saponifiable" components that do not become soap themselves, but rather remain in the soap you make and add their own characteristics to that soap. These may include non-oil plant materials, vitamins, minerals, etc. that may nourish the skin or provide other benefits. Two types of information are presented for each oil: Characteristics of soap made with the oil and characteristics of the oil itself when used to superfat soap or in a direct skin contact use such as massage oil. Experience with testing your own recipe formulas is important! Contributes to: soap hardness, stable lather, conditioning, silky feel, quicker trace. Palm oil makes a hard bar that cleans well and is also mild. It is a good substitute for animal tallow in allvegetable soaps. Palm oil is processed from the flesh of the fruit of tropical oil palm plants. This oil is solid at cool temperatures, becomes slushy at warm temperatures and a golden, clear liquid at higher temperatures.

Palm Oil

Palmitic 43-45% Oleic 38-40% Linoleic 9-11% Stearic 4-5% Myristic 1%

1. "Soaps and Detergents." UXL Encyclopedia of Science. 2002. Retrieved August 20, 2011 from Encyclopedia.com:http://www.encyclopedia.com/doc/1G2-3438100584.html

Soaps and Detergents

UXL Encyclopedia of Science | 2002 | 700+ words | Copyright

Soaps and detergents

A detergent is a cleaning agent. Detergents can be classified into one of two general categories: natural soaps (or just soaps) and synthetic detergents (or syndets). Both soaps and syndets have many similarities, particularly with regard to their molecular structures and the way they clean objects.

The structure of soaps and detergents

Both soaps and syndets consist of very long molecules. A model of such molecules is shown below: CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CHCOO, Na
+

The characteristic of all such molecules is that they have very different ends. The left end of the above molecule is said to be hydrophobic, meaning it "hates water." That end of the molecule is attracted by fats and oils, but not by water. The right end of the molecule above is said to be hydrophilic, meaning it "loves water." That end of the molecule is attracted by water but not by fats and oils. Most of the dirt that collects on clothing, dishes, and our bodies is surrounded by a thin layer of oil. Simply washing an object with water is not a very effective way of getting the object clean because oil and water do not mix with each other. But suppose that a detergent, either a soap or a syndet, is added to the wash water. In that case, detergent molecules line up with one end attached to the oily dirt and the other end attached to water molecules. When the object is scrubbed or agitated, the oil-covered dirt attached to detergent molecules, which are also attached to water molecules, is removed from clothing, dishes, or human skin. The dirtdetergent-water combination can then disappear down the drain.

Soaps
No one knows exactly when soap was discovered. It was apparently used by the Phoenicians as early as the sixth century b.c. Modern methods of soapmaking were not perfected, however, until late in the eighteenth century. In 1790, French chemist Nicholas Leblanc (17421806) invented a process for making caustic soda (sodium hydroxide) from common table salt (sodium chloride). His invention made it possible to manufacture soap inexpensively from ordinary raw materials. Soap is made by heating together fats or oils with water solutions of sodium hydroxide (lye). Molecules of fats and oils are very long molecules, like the one shown above. They do not have the charged group at the end of the molecule (COO, Na ) as shown in that structure, however. The charged group is obtained from the sodium hydroxide with which the fat or oil is mixed. Anyone can make his or her own soap simply by boiling a fat and lye together in a metal pot. The soap produced, however, would normally not be very pleasant to use. It would probably contain some left-over lye, which is very harsh. Washing with lye soap gets things clean but can be very damaging to human skin.
+

Today, soaps contain a number of ingredients to make them more pleasant to use. These ingredients include perfumes and coloring agents. Soaps may also be whipped into a lather when they are still liquid, to make them float; pressed into very hard bars, to make them last longer; or treated in other ways to give them special properties.

Synthetic detergents
Soap is one of the greatest chemical products ever invented by humans. It is highly effective in getting objects clean and in killing bacteria. But soap also has its disadvantages. Perhaps the most important of these disadvantages is its tendency to form precipitates in hard water. Hard water gets its name because of the fact that it is hard to make suds when trying to use soap in it. Perhaps you have seen the grayish scum that forms in a bathtub or a wash basin after you've taken a bath or washed some clothes in well water. The scum is a precipitate formed when soap reacts with the chemicals that make water hard. Washing with soap in hard water is a wasteful activity. The first thing that happens when you add soap to hard water is that the soap reacts with chemicals to form scum. In a way, you are just throwing away the first batch of soap you add because it can not be used to clean anything. Once all the chemicals in hard water are used up, then any additional soap can be used for cleaning something. Syndets do not have this problem. When a syndet is added to hard water, no precipitate is formed. The syndet is ready to go to work immediately to start cleaning something. The discovery of syndets in the 1940s had, therefore, a very dramatic effect on the soap market. In 1940, more than three billion pounds of soap were manufactured in the United States. Five years later, that number had risen to almost four billion pounds. In the same year, the first syndets began to appear on the market. After 1945, the amount of soap produced began to fall, while the amount of syndets began to increase. By 1970, about one billion pounds of soap was produced in the United States compared to nearly six billion pounds of syndets. As with soaps, syndets are always a mixture of substances that includes more than the cleaning agent itself. These additives include brighteners, bleaching agents, fillers, "builders," and perfumes and coloring agents.

2. "detergent." The Columbia Encyclopedia, Sixth Edition. 2008. Retrieved August 20, 2011 from Encyclopedia.com:http://www.encyclopedia.com/doc/1E1-detergen.html

detergent
The Columbia Encyclopedia, Sixth Edition | 2008 | Copyright detergent , substance that aids in the removal of dirt. Detergents act mainly on the oily films that trap dirt particles. The detergent molecules have a hydrocarbon portion, soluble in oil, and an ionic portion, soluble in water. The detergent acts as an emulsifier, i.e., by bridging the water and oil phases, it breaks the oil into tiny droplets suspended in water. The disruption of the oil film allows the dirt particles to become solubilized. Soap, the sodium salt of long-chain fatty acids, is a good detergent although it has some disadvantages, e.g., it forms insoluble compounds with certain salts found in hard water thus diminishing its effectiveness, and in acid solutions, frequently used in industry, it is decomposed (thus precipitating the free fatty acid of the soap). Synthetic detergents were produced experimentally in France before the middle of the 19th cent. and were further developed in Germany during World War I. However, not until the 1930s were chemical processes developed that made production in quantity feasible in any country. Synthetic detergents were first developed for commercial use in the 1950s. Detergents are classified as anionic, or negatively charged, e.g., soaps; cationic, or positively charged, e.g., tetraalkyl ammonium chloride, used as fabric softeners; nonionic, e.g., certain esters made from oil, used as degreasing agents in industry; and zwitterionic, containing both positive and negative ions on the same molecule. Detergents are incorporated in such products as dry-cleaning solutions, toothpastes, antiseptics, and solutions for removing poison sprays from vegetables and fruit. Laundry detergent preparations may contain substances called builders, which enhance cleansing; however, phosphatecontaining builders have been found to contribute to eutrophication of waterways and their use has been banned in many areas. Detergents that can be decomposed by microorganisms are termed biodegradable. Detergents are important chemicals used for enhanced petroleum recovery.