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Soap and Detergents Introduction

1. Cleansing agents are chemical substance used to remove grease and dirt. 2 . Th e r e a r e t wo t yp e o f c l e a n s i n g a g e n t s : a ) s o a p b)Detergents

3. Soaps are sodium or potassium salt of fatty acids that c o n t a i n s 1 2 t o 1 8 c a r b o n a t o m s p e r molecule.

4. Soaps are cleansing agents made from animal fats or vegetable oil by saponification. S o a p i s a s a l t o f a c o m p o u n d k n o w n a s a f a t t y a c i d . A s o a p m o l e c u l e c o n s i s t s o f a l o n g hydrocarbon chain (composed of carbons and hydrogens) with a carboxylic acid group on oneend 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 saltof 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- CH2CH2- C-ONa+ Non-polar hydrocarbon chain ionic end (Soluble in nonpolar substances) (Soluble in water) D e t e r g e n t s a r e s tr u c t u r a l l y s i mi l a r t o s o a p s , b u t d i f f e r i n t h e wa t e r - s o l u b l e p o r t i o n. Th r e e examples of detergents are shown below.

a sodium alkyl sulphate

a sodium alkylbenzene sulfonate

The History of Soap Manufacturing 1. Soap have been used for more than 3000 years. It was recorded that the Babylonians were makingsoaps 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 potassiumcarbonate. The ashes were boiled with lime (calcium oxide) to produce caustic potash (potassiumhydroxide). Caustic potash is then boiled with the animal fats to produce soap. a ) As h Li me b o i l e d C a u s t i c P o t a s h

b ) C a u s t i c P o t a s h + An i ma l F a t s b o i l e d S o a p

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 . Th i s p r o c e s s i s k n o wn a s t h e S o l v a y P r o c e s s wh i c h p r o d u c e s s o d i u m c a r b o n a t e c h e a p l y f o r industrial use. Sodium carbonate (often 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 rapiddevelopment of the soap and candle industry.

Preparation of soap by saponification

1. Soap is a cleansing agents produced by the reaction between sodium hydroxide and potassiumhydroxide with animal fats or vegetable oils. This reaction is know as saponification. 2. Fats and vegetable oils are large, naturally occurring ester molecules. When fats or oils are boiled w i t h c o n c e n t r a t e d a l k a l i s , s u c h a s s o d i u m h yd r o x i de , s a p o n i f i c a t i o n o c c u r s a n d t h e e s t e r 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 carbonatoms per molecule) 4. Some examples of soaps are shown below Sodium palmitate, Sodium oleate, Sodium stearate, Additives such as perfume, colouring matter and sometimes antiseptics are added to soaps toenhance their marketability. 5. Glyceryl tristearates are naturally occurring esters commonly found in animal fats and vegetable oils. Concentrated sodium hydroxide solution, saponification (alkaline hydrolysis) occurs and mixture of sodium stearate (soap) and glycerol is obtained

6. The soap produced can be precipitated by salt (sodium chloride) to the reactionmixture. 7. The sodium chloride added reduced the solubility of soap in water. As a result, precipitation of soap occurs. 8. The sodium chloride added reduced the solubility of soap in water. As a result, precipitation of soap occurs. 9. T h e p r o p er ti es o f s o a p d ep e n d o n : a)The type of alkali used for saponification b)The type of animal fats or vegetable oils used. 10. S o a ps pr o d u ce d f r o m s o d i u m h y d r o x i d e a r e h a r d, w her ea s s o a ps pr o d u ce d f r o m po t a s s i u m hydroxide are 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

(aq)s

m a t

s e

t i

e o + (aq)

a n

r s

t e + Na

2. The active substance in soap is the carboxylate ion, for example, stearate ion. The stearate ionconsist of two parts : the head and the tail. The head id negatively charged and the tail is along hydrocarbon chain. 3. The head contains the -C-O ions which dissolves readily in water (hydrophilic) but does notdissolve in oil. Conversely, the tail contains a long hydrocarbon chain which is insoluble inwater (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.

Detergents 1. D e t e r g e n t s a r e s yn t h e t i c c l e a n s i n g a g e n t s ma d e f r o m h yd r o c a r b o n s o b t a i n e d f r o m p e t r o l e u m 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 chargedion. 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. T h e r e a r e t wo t yp e s o f a n i o n i c d e t e r g e n t s : a) Detergent molecule with a benzene ring such as sodium alkylbenzene sulphonate. b) Detergent without a benzene ring such as sodium alkyl sulphate.

Preparation of detergents 1. The detergent, sodium alkyl sulphate can be prepared from alcohols with chain lengths of 12 to18 carbon atoms in two steps. Steps 1: Reaction with concentrated sulphuric acid Step 2: Neutralisation with sodium hydroxide solution.

A n e x a mp l e o f a l o n g c h a i n a l c o h o l i s d i d e c a n 1 o l , C H3(CH2)10CH2OH. The detergent prepared from dodecan -1 ol is called sodium dodecyl sulphate (IUPAC name) or sodium laurylsulphate (common name). CH3(CH2)10CH2OSO3-Na+. 3. Sodikum alkylbenzene sulphinates, were first used in 1940s. It can be prepared in three steps. Thestarting materials for making this detergents in a long chain alkene, RCH = CH2, obtained fromthe cracking of petroleum. a ) S t e p 1 : A l k y l a t i o n , Alkylation is the introduction of the alkyl group to an organic molecule b ) S t e p 2 : S u l p h o n a t i o n Al k yl b e nz e n e p r o d u c e d t h e r e a c t wi t h c o n c e n t r a t e d s u l p h u r i c a c i d a c i d t o f o r malkylbenzene sulphonic acid.Sulphonation is the introduction of the sulphonic acid group, -SO3H t o a n o r g a n i c molecule to form sulphonic acid. c ) S t e p 3 : N e u t r a l i s a t i o n Alkylbenzene sulphonic acid produced reacted with sodium hydroxide to form sodiumalkylbenzene sulphonate, the detergent

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). b ) Th e t a i l i s t h e l o n g h yd r o c a r b o n c h a i n , wh i c h i s n e u t r a l a n d h yd r o p h o b i c ( d i s s o l v e s readily in oils and grease, but not in water).

Alkylbenzene sulphonate ion

Alkyl sulphate ion

T H E

C L E A N S I N G O F S O A P A N D D E T E R G E N T

1. The cleansing action of soap or detergent depends on their chemical bonding and structures.a)The ionic head (negatively charged) is soluble in water (hydrophilic) but insoluble inoily layer. b)The long hydrocarbon tail (neutral) is insoluble in water (hydrophobic) b ut soluble inoily layer. 2. O i l c a n n o t b e w a s h e d a wa y f r o m c l o t h i n g wi t h wa t e r b e c a u s e o i l ( a c o v a l e n t mo l e c u l t 0 i s 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 inwater. 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 theforces 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 . E mu l s i f yi n g d i r t i n wa t e r :

a) Soaps and detergents can act as emulsifying agents to emulsify oils and grease. b ) Th e p r o c e s s of e mu l s i f i c a t i o n b r e a k s l a r g e d r o ps o f g r e a s e i n t o s ma l l e r d r o p l e t s t h a t 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.