form 5 Chemistry Folio- Soap and Detergent

Soap and Detergents

Introduction1. Cleansing agents are chemical substance used to remove grease and dirt.2. There are two type of cleansing agents :

a) Soapsb) Detergents

3. Soaps are sodium or potassium salt of fatty acids that contains 12 to 18 carbon atoms per molecule.

4. Soaps are cleansing agents made from animal fats or vegetable oil by saponification.

Soap is a salt of a compound known as a fatty acid. A soap molecule consists of a long hydrocarbon chain (composed of carbons and hydrogens) with a carboxylic acid group on one end which is ionic bonded to a metal ion, usually a sodium or potassium. The hydrocarbon end is nonpolar and is soluble in nonpolar substances (such as fats and oils), and the ionic end (the salt of a carboxylic acid) is soluble in water. The structure of a soap molecule is represented below:

O ||

CH3-CH2-CH2- CH2-CH2-CH2-CH2- CH2-CH2- CH2-CH2- CH2-CH2- CH2-CH2- C-O− Na+Non-polar hydrocarbon chain ionic end(Soluble in nonpolar substances) (Soluble in water)

Detergents are structurally similar to soaps, but differ in the water-soluble portion. Three examples of detergents are shown below.

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a sodium alkyl sulfate

a sodium alkylbenzene sulfonate

SoapThe History of Soap Manufacturing

1. Soap have been used for more than 3000 years. It was recorded that the Babylonians were making soaps around 2800 B.C.

2. The ‘Purifying Oils’ were recorded on Hebrew tablets in 4000 B.C.3. In ancients time, soap made from ashes of plants which contain sodium carbonate and potassium

carbonate. The ashes were boiled with lime (calcium oxide) to produce caustic potash (potassium hydroxide). Caustic potash is then boiled with the animal fats to produce soap.

a) Ash + Lime boiled Caustic Potash(K2CO3) (CaO) (KOH)

b) Caustic Potash + Animal Fats boiled Soap

4. In 1861, the Belgian Chemist Ernest Solvay (1838-1922) discovered the process to make soda (sodium carbonate) from common salt (sodium chloride) and calcium carbonate.

5. This process is known as the Solvay Process which produces sodium carbonate cheaply for industrial use. Sodium carbonate (often called soda or soda ash) is used for making glass, soaps and detergents.

6. Michel Chevreul (1786-1889), a French chemist, was noted for his research in the composition of animal fats is composed of fatty acids and glycerol. This discovery contributed to the rapid development of the soap and candle industry.

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Preparation of soap by saponification

1. Soap is a cleansing agents produced by the reaction between sodium hydroxide and potassium hydroxide with animal fats or vegetable oils. This reaction is known as saponification.

2. Fats and vegetable oils are large, naturally occurring ester molecules. When fats or oils are boiled with concentrated alkalis, such as sodium hydroxide, saponification occurs and the ester molecules are broken down into soap and glycerol.Fats or vegetable oils + concentrated alkalis soap +glycerol

3. Saponification is the alkaline hydrolysis of ester using alkali solutions. From the chemist aspect, soaps are sodium salts or potassium salts of long chain carboxylic acids (with 12 to 18 carbon atoms per molecule).

4. Some examples of soaps are shown below.a) Sodium palmitate, C15H31COONab) Sodium oleate, C17H33COONac) Sodium stearate, C17H35COONa

Additives such as perfume, colouring matter and sometimes antiseptics are added to soaps to enhance their marketability.

5. Glyceryl tristearates are naturally occurring esters commonly found in animal fats and vegetable oils. When the ester is boiled with concentrated sodium hydroxide solution, saponification (alkaline hydrolysis) occurs and mixture of sodium stearate (soap) and glycerol is obtained.

CH2COOC17H35 CH2OH

CHCOOC17H35 + 3NaOH CHOH

(heating)

CH2COOC17H35 3C17H35COONa + CH2OH

Glyceryl tristearate Sodium stearate (soap) Glycerol

6. The soap produced can be precipitated by adding common salt (sodium chloride) to the reaction mixture.

7. The sodium chloride added reduced the solubility of soap in water. As a result, precipitation of soap occurs.

8. The properties of soap depend on :a) The type of alkali used for saponificationb) The type of animal fats or vegetable oils used.

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9. Soaps produced from sodium hydroxide are hard, whereas soaps produced from potassium hydroxide are soft.

10. Animal fats (tallow) from cows and vegetable oils (such as palm oil or olive oil) ae used for making soap.

The structure of soap molecule

1. When soap is dissolved in water, it will dissociate and produce sodium ions and carboxylate ions (RCOO-). For example, sodium stearate dissolves in water to form sodium ions and stearate ions.

C17H35COONa (s) + water C17H35COO- (aq)sodium stearate stearate ions

+ Na + (aq)2. The active substance in soap is the carboxylate ion, for example, stearate ion. The stearate ion

consist of two parts : the ‘head’ and the ‘tail’. The ‘head’ id negatively charged and the ‘tail’ is a long hydrocarbon chain.

3. The ‘head’ contains the -C-O- ions which dissolves readily in water (hydrophilic) but does not dissolve in oil. Conversely, the ‘tail’ contains a long hydrocarbon chain which is insoluble in water (hydrophobic) but dissolves readily in oil.

4. Soaps made from palmitic acid are known as sodium palmitate. Figure 5.2 shows the structure of the palmitate ion in soaps.

5. The figure 5.3 9a) shows the molecular model of palmitate ion and Figure 5.3 (b) shows the simple representation of the structure of the palmitate ion.

(a) The molecular model of the palmitate ion.

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O

(b) The diagrammatic representation of the soap ion.

Detergents1. Detergents are synthetic cleansing agents made from hydrocarbons obtained from petroleum

fractions. Thus, detergents are petrochemicals. 2. Detergents can be classified into three main types, depending on the charge on the detergent ion.

a) Anionic detergents where the head of the detergent particle contains a negatively charged ion.Example: R – O – SO3

-Na+ (Sodium alkyl sulphate)

b) Cationic detergents where the head of the detergent particle contains a positively charged ion.Example: R – N (CH3)3

+BR-

c) Non ionic detergents

Example: R – O – CH2CH2OH

3. There are two types of anionic detergents : a) Detergent molecule with a benzene ring such as sodium

alkylbenzene sulphonate.

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Positively charged ion

Negatively charged ion

Where R represents a long hydrocarbon chain.

We can represent the detergent ion, alkylbenzene sulphonate ion, more simply as :

b) Detergent molecule without a benzene ring such as sodium alkyl sulphate.We can represent the detergent ion, alkyl sulphate ion as:

R – OSO3-

Preparation of detergents

1. The detergent, sodium alkyl sulphate can be prepared from alcohols with chain lengths of 12 to 18 carbon atoms in two steps.

Steps 1: Reaction with concentrated sulphuric acid

Step 2: Neutralisation with sodium hydroxide solution.

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2. An example of a long chain alcohol is didecan – 1 –ol, CH3(CH2)10CH2OH. The detergent

prepared from dodecan -1 –ol is called sodium dodecyl sulphate (IUPAC name) or sodium lauryl sulphate (common name). CH3(CH2)10CH2O-SO3

-Na+ .3. Sodikum alkylbenzene sulphinates, were first used in 1940s. It can be prepared in three steps. The

starting materials for making this detergents in a long chain alkene, RCH = CH2 , obtained from the cracking of petroleum.

a) Step 1 : Alkylation

Alkylation is the introduction of the alkyl group to an organic molecule.

b) Step 2 : SulphonationAlkylbenzene produced the react with concentrated sulphuric acid acid to form alkylbenzene sulphonic acid.

Sulphonation is the introduction of the sulphonic acid group, -SO3H to an organic molecule to form sulphonic acid.

c) Step 3 : NeutralisationAlkylbenzene sulphonic acid produced reacted with sodium hydroxide to form sodium alkylbenzene sulphonate, the detergent

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The structure of detergent molecule

When a detergent is dissolved in water, it dissociates to form sodium ions (Na+) and detergent ions. The detergent ions have the same basic structure as the soap ions, that is consist of two parts :

a) The ‘ head’ is the sulphate group (-OSO3-), which is negatively charged and hydrophilic

(dissolves readily in water but not in oils and grease).

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b) The ‘tail’ is the long hydrocarbon chain, which is neutral and hydrophobic (dissolves readily in oils and grease, but not in water).

alkyl sulphate ion

Alkylbenzene sulphonate ion

The cleansing of soap and detergent

1. The cleansing action of soap or detergent depends on their chemical bonding and structures.

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a) The ionic ‘head’ (negatively charged) is soluble in water (hydrophilic) but insoluble in oily layer.

b) The long hydrocarbon ‘tail’ (neutral) is insoluble in water (hydrophobic) but soluble in oily layer.

2. Oil cannot be washed away from clothing with water because oil (a covalent molecult0 is insoluble in water.

3. Lifting greasy dirt from the surface cloth. When soap or detergent is added to the dirty surface of a piece of cloth covered with a layer of oil or grease.

a) The negatively charged ‘head’ (hydrophilic) of soap ions or detergent ions dissolves in water.

b) The hydrocarbon ‘tail’ (hydrophobic) of soap or detergent ions dissolves in the layer of grease.

4. I the water is agitated slightly, the grease begins to be lifted off the surface. This cause by the forces of attraction between the water molecules and the negatively charged heads.

The cleansing action of soap

5. On further agitation during washing, the greasy dirt is lifted from the surface.6. Emulsifying dirt in water

a) Soaps and detergents can act as emulsifying agents to emulsify oils and grease.b) The process of emulsification breaks large drops of grease into smaller droplets that

floats in water. The greasy droplets repel on another because they carry the same charge. As a result, the grease is suspended in the solution.

c) When the cloth is rinsed with the water, the droplet will be carried away.d) The cleaning process become more efficient in the water containing the soap or detergent

solution is stirred

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Additives in detergents1. Modern detergents used for washing clothes usually contains a few types of additives to :

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a) Increase their cleaning power.b) Make them attractive and saleable.

2. Only about 20% of the substances in a detergent are cle4ansing agents (sodium alkyl sulphate or sodium alkylbenzene sulphonate). The other substances are additives. The examples of addictives and their functions are described as follows :

3. Builders : Sodium tripolyphosphate (Na5P3O10)a) Sodium tripolyphospathe is usd to soften hard water. In the presence of sodium

tripolyphosphate, Ca2+ ions and Mg2+ ions are removed.

b) Sodium tripolyphosphate increases the pH value of water. In this way, muddy dirt can be removed.

4. Whitening / bleaching agents : sodium perboratea) Bleaches (bleaching agents) remove coloured stains by oxidation process. When

coloured stanis are oxidized, the colour will disappear.b) The whitening (bleaching) agents commonly used in detergent are sodium perborate

(NaH2BO43H2O). Sodium perborate decomposes in hot water to release oxygen (an oxidising agent) which is responsible for the whitening (bleaching) action.

c) Unlike chlorine, oxygen does not bleach the colour of dyes are not damaging to fabrics. When properly used, the perborate bleaches make fabrics whiter than chlorine bleaches and the colourful dyes of the fabrics do not fade when dirty stains are removed.

d) Besides sodium perborate, sodium hypochlorite, (NaCIO) can also be used as bleaches in detergents. The IUPAC name of sodium hypochlorite is sodium chlorate (I).

e) Sodium hypochlorite releases chlorine that bleaches with dirty stains. However, high concentrations of chlorine can be quite damaging to fabrics. These bleaches do not work well on synthetic fabrics (polyster fabrics), often causing a yellowing rather than the desire whitening. Also chlorine causes the dyes on fabrics to fade.

5. Biological enzymes : Amylase, lipase, and proteasea) Protein stains such blood, milk, and tomato sauce cannot be removed by the ordinary

detergents because these types of stains are insoluble in water.b) Biological enzymes in detergents can break down fat and protein molecules in food

stains. The fatty acids, glycerol and amino acids produced are soluble in water and are removed during washing.

6. Brightenersa) Figure below shows the action of brighteners. The brighteners absorb the invisible ultra-

violet and re-radiate it as blue light.

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Brightener

Cloth

b) Brighteners make fabrics appear whiter and brighter because the blue light can hide any yellowing on the fabrics. Blue light added to the yellow light reflected on old fabrics make them look white.

7. Drying agents ; Sodium sulphate and sodium silicateAnhydrous sodium sulphate and sodium silicate (Na2S2O3) are used as drying agents to ensure that the detergent in powdered firm is always in a dry condition.

8. Stabilisersa) The functions of stabilizers is to prevents the formation of foam.b) In an automatic washing machine, excessive foam can stop the pump working. So,

washing powders for automatic washing machine are made using detergents that are good at removing and emulsifying grease, but do not produced foam.

9. PerfumesPerfumes are added to make clothes smell fresh and clean.

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The effectiveness of soaps and detergents as cleansing agents Advantages of soaps

1. Soaps are effective cleansing agents in soft water, that is water does not contain Mg2+ and Ca2+

ions.2. Soaps do not cause pollution problems to the environment. This is because soaps are made from

chemical found in animals and plants. This means that soaps are biodegradable, that is they can be composed by the action of bacteria.

Disadvantages of soaps

1. Soaps are ineffective in hard water, that is, water that contains magnesium and calcium salts.2. In hard water, soaps will react with Mg2+ and thus, soaps do not lather in hard water.3. Scum is grey solid that is insoluble in water. It consists of magnesium stearate and calcium

stearate.4. Soaps are not also effective in acidic water, for example rainwater containing dissolves acids. H +

ions from acids will react with soap ions to produce carboxylic acids molecular size that are insoluble in water.

5. Stearic acids and other carboxylic acids do not act as cleansing agents because they exist mainly as molecules and do not anionic hydrophilic ends (’head’) that dissolves in water.

Advantages of detergents

1. Detergents are cleansing agents that are effective in soft water as well as hard water. This is because detergents do not form scum with Mg+ and Ca2+ ions found in hard water.

2. The detergents ions (R –O – SO3- and R – SO3

- )react with Mg+ and Ca2+ ions in hard water. However, the magnesium salts and calcium salts which are formed are soluble in water. Hence, the scum is not formed and the detergents are still active in hard water and lathers easily.

3. Detergents are synthetic cleansing agents. This means that the structure of the hydrocarbon chain can be modified to produce detergents with specific properties. Nowadays, different types of detergents have been synthesised for specific uses such as shampoos and dish cleaner.

4. Furthermore, detergents are also effective in acidic water because H+ ion is acidic water do not combined with detergents ions.

Disadvantages of detergents

1. Most detergents have branched hydrocarbon chains and are non-biodegradable, that is, they cannot decomposed by bacteria. As a result, non-biodegradable detergents cause water pollution.

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2. Phosphates in detergents act as fertilizers and promote the growth of water plants and algae. When the plants die and decay, they will used up the oxygen dissolves in water. This will decrease the oxygen content in water and kill fishes and other aquatic lives.

3. Detergents produce a lot of foam in water. The layer of foam that covers the water surface will prevents oxygen from dissolving in water. This condition will cause fish and other aquatic life ti die from oxygen starvation.

4. Additives such as sodium hydrochlorite (bleaching agents) releases chlorine gas in water that is acidic. Chlorine gas is highly toxic and kills aquatic life.

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