Non-Hydrocarbon Esters 1.

. General formula: CnH2n+1COOCmH2m+1 Where n = 0, 1, 2, 3 and m = 1, 2, 3 (n and m = number of carbon) RCOOR where R and R represented the same or different alkyl groups. 2. Esters are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 3. The functional group in ester is carboxylate group, COO -. CnH2n+1COOH + CmH2m+1OH > CnH2n+1COOCmH2m+1 + H2O

First part: taken from the alcohol (alkyl group) Second part: taken from the carboxylic acid (-oic to -oate) Molecular formula of Prepared from ester HCOOC2H5 CH3COOCH3 CH3COOC3H7 C2H5COOC2H5 Odour Banana Pineapple Orange Apple Ethanol + Methanoic acid Methanol + Ethanoic acid Propanol + Ethanoic acid Ethanol + Propanoic acid

Name of ester Ethyl methanoate Methyl ethanoate Propyl ethanoate Ethyl propanoate Name 3-metylbutyl acetate Ethyl butanoate Octyl ethanoate Isoamyl isovalerate

4. Physical properties of ester

Simple esters are colourless liquid and are found in fruits and flowers. Esters have sweet pleasant smell. Esters are covalent compounds. Esters are insoluble in water but soluble in organic solvent. Esters are less dense than water. Esters are neutral and cannot conduct electricity. The higher and more complex esters have higher boiling points and less volatile.

Natural sources:

Vegetable oils (palm oil) and liquids esters can be found in plants derived from glycerol and fatty acids. Fats are solid esters (milk fat) derived from glycerol and fatty acids. Waxes (beewax) are solid ester derived from long-chain fatty acids and long-chain alcohols. Preparation of cosmetics and perfumes (esters are volatile and have sweet smell).

5. Uses of Esters

Synthetic esters used as food additives (artificial flavour). Natural esters serves as storage reserve of energy in living things. In plant, wax (esters) helps to prevent dehydration and attack of microorganisms. Esters used as solvents for glue and varnishes. Esters used to make plastics softer. Esters used to produce polyester (threads and synthetics fabrics) Esters used to produce soap and detergents.

Non-Hydrocarbon Fats 1. Fatrs are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms. 2. Fats (lipids / triglycerides) are belonging to the group in ester. 3. Natural esters are formed from glycerol and fatty acids. Name of fat Molecular formula of ester Types of fatty acids Lauric acid* Palmitic acid* Stearic acid* Oleic oxide ** Linolenic acid*** * Saturated: C-C single bonds ** Unsaturated (monounsaturated): C=C double bonds *** Unsaturated (polyunsaturated): C=C double bonds 4. Animal fats have higher percentage of saturated fatty acids than unsaturated fatty acids. 5. Plant oils have higher percentage of unsaturated fatty acids than saturated fatty acids. 6. Physical properties of fats Saturated Types of fatty acids Bonding Melting point Sources Cholesterol State at room temperature C-C single bonds single higher animals high solid Unsaturated C=C double bonds double lower plants low liquid CH3(CH2)10COOH CH3(CH2)14COOH CH3(CH2)16COOH CH3(CH2)7CH=CH(CH2)7COOH Saturated Saturated Saturated Unsaturated Unsaturated

Linoleic acid*** CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH

CH3CH2CH=CHCH2CH=CHCH2CH=CH(CH2)7COOH Unsaturated

Fats (animal) in general are solids at room temperature and acted as:

thermal insulator protective cushion to protect the vital organ provide energy and stored in body carry Vitamin A, D, E, K (insoluble in water) Example: butter, fish oil (liquid in room temperature) Fats (plant) are called oils. Oils are liquids at room temperature. Example: olive oil, peanut oil, palm oil and bran oil Unsaturated fats can be converted into saturated fats by hydrogenation (additional reaction) in 200C and 4 atm in the presence of nickel catalyst. Example: production of margarine from sunflower oil of palm oil.

7. Chemical properties of fats

8. Effect of fats Fatty food produce high energy but high consumption of fatty food will results:

obesity raise the level of cholesterol deposition will cause block the flow of blood which lead to stroke and heart attack. It is extracted from fresh oil palm fruits. Palm oil extracted from the pulp of the fruits.

9. Palm oil

Steps in extraction of palm oil: 1. sterilising (oil palm fruit)

2. stripping 3. digestion (crushing the husk and fruit and separate the oil by heating) 4. squeezed out the oil 5. extraction (separate the oil from water) 6. purification the oil (palm oil is treated with phosphoric acid and then steam is passed through to separate the acid) 7. vacuum Palm kernel oil extracted from the kernel or seed. Steps in extraction of palm oil: 1. sterilising (oil palm fruit)

2. stripping 3. crushing the husk and fruit

4. extracting kernel oil 5. purification (purify the oil from kernel) Goodness in palm oil:

higher proportion of unsaturated fats. easy to digest and absorb. rich in vitamin A (carotenoid) rich in vitamin E (tocophenols and tocotrienols) resist oxidation in high temperature.

Polymers 1. Polymer many small units (monomers) joining together to formed large molecule. 2. Polymer can be classified into two groups:

synthetic polymers / man-made polymers (polythene; PVC polyvinyl chloride; artificial silk; and polypropene) natural polymers (natural rubber; starch; cellulose; and proteins) General formula: Cx(H2O)y with the ratio of H:O = 2:1 Carbohydrates have cyclic structure. Monomer: glucose (C6H12H6) Reaction to form polymer: condensation reaction (- H2O) Protein consists of carbon, hydrogen, oxygen and nitrogen (some have sulphur, phosphorus and other elements) Monomer: amino acids Amino acids have two functional group which are carboxyl group (-COOH) and amino group(NH2) Reaction to form polymer: condensation reaction (- H2O) Extracted from the latex of rubber tree (Hevea brasiliensis) which the tree originates from Brazil. A molecule of rubber contains 5000 isoprene units. Monomer: isoprene, C5H8 or 2-methylbuta-1,3-diene. Reaction to form polymer: additional polymerisation (one of the double bond in isoprene becomes single bond)

3. Natural polymer: Carbohydrates (polysaccharides) (starch, glycogen and cellulose)

4. Natural polymer: Protein (polypeptide)

5. Natural polymer: Natural rubber

6. Structure of rubber molecule

Latex is colloid (35% rubber particles and 65% water).

Rubber particle contains rubber molecules which are wrapped by a layer of negatively-charged protein membrane. Same charge of rubber molecules repels each other. This prevent rubber from coagulate.

7. Coagulation process of latex The process for the coagulation of latex is summarised as: 1. Acid (H+) can neutralise the negatively-charged protein membrane. Example of acid: formic acid, methanoic acid, suphuric acid and hydrochloric acid. 2. The rubber molecules will collide after the protein membrane is broken. 3. Rubber molecules (polymers) are set free 4. Rubber molecules combine with one another (coagulation). 8. Natural coagulation process of latex For the natural coagulation of latex: 1. Latex is exposed to air without adding acid (duration overnight). produce acid) 9. Prevent coagulation process of latex The following are latex coagulation prevention method: 1. Alkaline / Basic solution is added to the latex. Example: ammonia (NH3). charged hydroxide ion / OH- from ammonia solution. 10. Properties of natural rubber

2. Coagulation process occurs in slower pace due to the bacteria (microorganism) action which

2. Positively-charged hydrogen ion / H+ produced by bacteria can be neutralised by negatively-

elastic cannot withstand heat (become sticky and soft above 50C; decompose above 200C; hard and brittle cooled) easily oxidised (present of C=C) insoluble in water (due to the long hydrocarbon chains) soluble in organic solvent (propanone, benzene, petrol etc.)

11. Vulcanisation of rubber Vulcanisation process of hardening rubber and increases rubber elasticity by heating it withsulphur or sulphur compounds. Methods:

heating natural rubber with sulphur at 140C using zinc oxide as catalyst or dipping natural rubber in a solution of disulphur dichloride (S2Cl2) in methylbenzene.

12. Properties of vulcanisation of rubber

The sulphur atoms are added to double bonds in the natural rubber molecules to formdisulphide linkages (-C-S-S-C-) / sulphur cross-links between the long polymer chains. Therefore, vulcanised rubber is more elastics and stronger.

This increases the molecular size and the intermolecular forces of attraction between rubber molecules. Therefore, vulcanised rubber is more resistant to heat (does not become soft and sticky when hot).

This also reduces the number of carbon-carbon double bonds in rubber molecules. Therefore, vulcanised rubber is more resistant to oxygen, ozone, sunlight and other chemicals.

13. Comparison between the properties of vulcanised rubber and unvulcanised rubber Properties Double bonds Melting point Elasticity Vulcanised rubber Decreases (formation of sulphur cross-links) High (presence of sulphur) More elastic (sulphur crosslinks prevents the polymer chain or rubber from slipping past. Strength and hardness Strong and hard (depends on Weak and soft (polymer degree of vulcanisation) chain of rubber will break when rubber is over stretched. Resistant to heat Oxidation Resistant to oxidation (reduction of number of double bonds per rubber molecule) 14. R & D of rubber

Unvulcanised rubber More number of double bonds Low Less elastics

Resistant to heat

Poor resistant to heat Easily oxidised by oxygen, UV light (presence of many double bonds per rubber molecules)

RRIM Rubber Research Institute of Malaysia MRB Malaysian Rubber Board Rubber Technology Centre Various local higher institutions of learning