SEBATIAN AROMATIK

Aromatic compounds were originally named because of their pleasant aromas. The adjective "aromatic" is used by organic chemists in a rather different way than it is normally applied. It has its origin in the observation that certain natural substances, such as cinnamon bark, wintergreen leaves, vanilla beans and anise seeds, contained fragrant compounds having common but unexpected properties. Cinnamon bark, for example, yielded a pleasant smelling compound

Aromatic hydrocarbon
Aromatic hydrocarbon sometimes called arenes. The ending- ene means that they are unsaturated like alkenes and the ar- prefix comes from the word aromatic which means smell. An organic compound that contains a benzene ring in its molecule is known as an aromatic compound. The simplest yet most important member of the aromatic hydrocarbon is benzene.

Properties of aromatic compounds

Cyclic and each atom in the ring is a center (uses a p atomic orbital to form -type bonds),ie, sp2 or sp. Ring is flat or nearly so

 High degree of unsaturation but resistant to addition reactions generally undergo electrophilic

attached to the ring). Unusually stable. -Electrons delocalized above and below plane of ring.

substitution (an electrophilic reagent replaces a hydrogen [usually]

Sources of Aromatic Compounds

1) petroleum not rich in aromatics, but has some. 2) reforming cycloalkanes from petroleum 3) coal tar and coal gas. plants > peat > lignite > bituminous (soft) coal > anthracite (hard)

Structure of Benzene
All aromatic compounds are based on benzene, C6H6, which has a ring of six carbon atoms and has the symbol:
H

or

H H

Each corner of the hexagon has a carbon atom with a hydrogen attached.

Structural formula of benzene:

The circle represents the six electrons that are delocalized about the six carbon atoms of the benzene ring

All carbon atoms in benzene are sp2-hybridized

The side-way overlap of unhybridized 2p orbitals on both sides gives a delocalized electron cloud above and below the plane of the ring

The delocalization of electrons gives benzene extra stability and determines the chemical properties of benzene

 Many simple aromatic compounds, however, have their own unique name. These are names that are not derived from the word benzene.

(methylbenzene)

(hydroxybenzene)

(phenylamine)

(benzenecarboxylic acid)

Determining Aromaticity
Criteria for aromaticity Pi bond must lie within cyclic structure Each atom in the cycle must have p orbital, forming p orbital loop All p orbitals in the loop must overlap (panarity) Huckels Rule: orbital arrangement must result in a lowering of energy electrons ( n is an interger: 0.1,2, 3) in the loop

e.g
Derermine if the following molecule is aromatic

Step 1: Do pi bond lie within a cyclic structure 3 pi bond are present each lying within the cyclic structure of benzene

Step 2: Does each atom in the cycle have p orbital forming a p orbital loop

Each atom has a p orbital forming a loop

Step 3 : Do all p orbitals overlap and lie within the same plane By rotating the molecule, we see that all orbitals lie within the same plane

Step 4: Does the molecule follow Huckels rule

6 total pi electrons 4n + 2 = 6 n=1

Conclusion: Benzene is an aromatic

Physical properties of aromatic hydrocarbons: have a fragrant smell

generally less dense than water at 20C

They are water insoluble / usually immiscible with water

soluble in organic solvents All aromatic hydrocarbons are resonance stabilized. They are also carcinogenic (cancer forming) if exposed with sufficient concentration and exposure time. They all undergo electrophilic aromatic substitutions. Most have a sweet aroma hence the reason for the name "aromatic".

Benzene Reactivity
1. Benzene tends to undergo reactions in which the stable ring is instact because of the extra chemical stability of delocalised electron ring. 2. Benzene requires a strong electrophile and a catalyst ..and then it undergoes substitution reactions, not addition.

Cl
+

Cl2

FeCl3
catalyst

HCl

substitution

compare:

Cl2
no catalyst

Cl Cl
addition

Benzene Reactivity
1. Benzene tends to undergo reactions in which the stable ring is instact because of the extra chemical stability of delocalised electron ring. 2. Benzene requires a strong electrophile and a catalyst ..and then it undergoes substitution reactions, not addition.

Cl
+

Cl2

FeCl3
catalyst

HCl

substitution

compare:

Cl2
no catalyst

Cl Cl
addition

Electrophilic Aromatic Substitution Reactions

Most characteristic reaction of aromatic compounds: Electrophilic substitution reactions

The electrophiles attack the benzene ring, replacing one of the hydrogen atoms in the reaction Electrophiles are either a positive ion (E+) or some other electron-deficient species with a partial positive charge (+)

MECHANISM
All of the reactions follow the same pattern of mechanism. The reagents combine to form a strong electrophile E+ ,and its partner (:X ), which react as follows:
ELECTROPHILIC AROMATIC SUBSTITUTION

H E+
slow

(+) E

E H
+ HX
:X

(+)

intermediate benzenium ion* resonance structures are shown by the (+) symbols

restores ring resonance

* also called a benzenonium ion

REACTION OF BENZENE
1. Nitration

reflux

( pale yellow liquid)

Conc. H2SO4 increases the rate of reaction by increasing the concentration of the electrophile, NO2+ (nitronium ion)

Reaction mechanism of nitration of benzene

The substitution reaction of benzene involves electrophilic substitution. The high density of the ve charge in the delocalised electrons of the benzene ring tends to attract electrophiles. In the nitration of benzene, the electrophile is the nitronium(nitryl) ion NO2+, generated by the reaction of concentrated sulphuric acid.

 Sulphuric acid, being a stronger acid, donates a proton to nitric acid.

BASE

ACID

The protonated nitric acid breaks up to form a molecule of water and the electrophile, the nitronium ion, NO2+

 The nitronium ion attacks the benzene ring to form a resonance stabilised cation intermediate:

 The intermediate rapidly loses a proton to either water or the hydrogensulphate ion, HSO4-, regenerates the aromatic ring and gives nitrobenzene.

2. Halogenation
Benzene reacts with chlorine and bromine in the presence of catalysts such as AlCl3, FeCl3, FeBr3, to give chlorobenzene and bromobenzene respectively. This reaction involves substitution of a halogen atom for a hydrogen atom on the aromatic ring. In the dark, benzene does not react with chlorine or bromine or iodine. This is because the halogen molecule is non-polar with no centre of positive charge to initiate electrophilic attack on the benzene ring.

 The presence of a catalyst or halogen carrier such as aluminium chloride, AlCl3, benzene is substituted by chlorine or bromine at room temperature.
AlCl3

 The catalyst AlCl3, an electron deficient compound which has only six electron in its outer shell, accepts the lone pair of electrons from one of the chlorine atoms, which induces polarisation on the clorine molecule.

Formation of the Chloronium Ion Complex

: Cl :
Al

..

.. .. Cl : ..
..+ .. Cl : Cl .. .. : Cl : .. Al Cl : .. : Cl : ..

.. : Cl ..

.. Cl : ..

: Cl : ..

: Cl : .. .. + .. Al Cl : : Cl : Cl .. .. .. : : Cl ..
chloronium ion complex

..

Chlorination of Benzene
H AlCl4 Cl

Cl2 + AlCl3

+ [ Cl AlCl4 ]
chloronium ion complex
Positive charged end of chlorine Molecule is now electrophile and Attacks the benzene ring

benzenium ion

Cl

+ HAlCl4
HCl + AlCl3

Positive charged end of chlorine molecule is now electrophile and attacks the benzene ring

 Benzene also reacts with chlorine in the presence of ultraviolet light to form, 1,2,3,4,5,6-hexachloroxyclohexene. This reaction is addition reaction.
Cl

Cl
+

Cl

3 Cl2

hv radiation warm

Cl

Cl

Cl

3.Alkylation- Friedal-Crafts Reaction

When benzene is warmed with a haloalkane in the presence of catalysts such as AlCl3, an alkylbenzene is formed

This reaction substitutes an alkyl group for a hydrogen atom on an aromatic ring.

Important step in chemical industry to produce

polystyrene, phenol and detergents

Formation of a Carbocation Complex

- AlCl3 , polarises the CH3Cl molecule ..

.. .. Cl: ..
+
CH3

.. CH3 Cl : ..

: Cl :
Al

: Cl : ..
Other aliphatic R-Cl may be used

: Cl : .. .. Cl Al Cl : .. .. : Cl : ..

: Cl : .. .. + CH3 : Cl Al Cl : .. .. : : Cl ..
(electrophile)

..

carbocation

Friedel-Crafts Alkylation
H AlCl4 CH3
Loss a proton Ion H release react with AlCl4-

CH3Cl + AlCl3

-] [ CH+ AlCl 3 4
The +ve charged methyl group attacks the benzene Ring and electrophilic substitution occurs.

CH3

+ HAlCl4
HCl + AlCl3

4. FRIEDEL-CRAFTS ACYLATION
This involve substitution of an acyl group, RCO, for a hydrogen atom on the aromatic ring. When benzene is added to ethanoyl chloride and AlCl3, under anhydrous conditions, a substitution reaction occurs and phenylethanone is formed.

Friedel-Crafts Acylation
O CH3 C Cl + AlCl 3

AlCl4 C CH3 O

+ -] [ CH3 C AlCl4
O

Loss a proton Ion H release react with AlCl4-

RCO+ is a good electrophile and Would attack the benzene ring To form substitution product

C CH3 O

+ HAlCl4 HCl + AlCl3

5.Sulphonation
This involves substitution of an SO3H group for a hydrogen atom in the aromatic ring. If benzene and conc sulphuric acid are refluxed together for several hours, benzenesulphonic acid is formed

reflux

The electrophile under these conditions is HSO3+ ion.

O
O

HO S OH +

H+ HO S O
O

H H

+ HO S

O
O + H2O

 Benzene can also be sulphonated by fuming H2SO4 ( a solution of SO3 in H2SO4 acid in the cold). - the electrophile under this conditions is SO3 ( sulphur trioxide). -sulphur trioxide carrier a large partial +ve charge on the sulphur atom.
-

S
-

O
Production of electrophile : 2H2SO4 SO3+H3O- + HSO4-

Sulfonation of Benzene
HSO4 O
+S H2SO4 . SO3

O S OH O

OH

O
H3O+ D

Loss a proton

can be reversed in boiling water or steam (acidic)

O S OH O
+ H2SO4

6.Oxidation of Benzene
Comman oxidizing agents ( KMnO4) have no effect on benzene. The benzene ring is stable to oxidation. Because of the extra chemical stability of the delocalised orbitals. Reactions which disrupt the delocalised electron system are less favourable and need higher temperature and more vigorous conditions.

 Benzene burn in air with a smoky flame to produce carbon dioxide and water. 2C6H6 + 15O2 12CO2 + 6H2O

Reaction of Bromine with Benzene, Phenol, and Toluene

Benzene and toluene do not react with bromine in the absence of a catalyst. Phenol is more reactive due to the presence of an electron donating hydroxyl group and reacts with bromine by a substitution reaction forming hydrogen bromide gas.

Methylbenzene
methylbenzene, also known as Toluene. is a clear, water-insoluble liquid with the typical smell of paint thinner, redolent of the sweet smell of the related compound benzene. Molecular formula : C7H8

Structure of Methylbenzene/ toluene

All C atoms in the ring is sp2-hybridized

The C atom in the methyl group is sp3-hybridized

The delocalized electron clouds give rise to extra stability

Reaction of Methylbenzene
The chemical reaction for methylbenzene can be divided into 2 group: i. reaction involving the alkyl side chain. ii. Reaction involving the aromatic ring ( or the nucleus)
CH3
Side chain.

Nucleus/ aromatic ring

i.

Reaction involving the alkyl group (side chain)

A. Halogenation
methylbenzene (under reflux) in the presence of strong sunlight or ultra-violet light. - Free radical substitution takes place in the side chain, proceeds in a similar way to the chlorination of methane. - Substitution takes place on the methyl group

- when chlorine is bubbled through boiling

+ HCl
(chloromethyl) benzene

CH3Cl

CHCl2

+ HCl
(dichloromethyl) benzene

CHCl2

CHCl33

+ HCl
(trichloromethyl) benzene

The actual product depends on how long the chlorine is passed through the boiling methylbenzene. The reaction may be stopped at any stage when the theoretical mass increase has been obtained.

Mechanism of chlorination:
i. Chain initiation

ii. Chain Propogation

C6H5CH3+ Cl C6H5CH2 + Cl2
iii. Termination Step

C6H5CH2

+ HCl

C6H5CH2Cl + Cl

Cl . + Cl.

Cl2

B. Oxidation
Benzene is very resistant to oxidation, being unaffected by strong oxidizing agents such as chromic acid (H2CrO4) and potassium permanganate (KMnO4). However, carbons attached to the benzene ring (benzyl groups) can frequently be oxidized.

 When alkyl benzene is heated with strong oxidising agents such as acidified potassium maganate(VII) or acidified potassium dichloromate(VI), the side chain (irrespective of its length or size) is oxidised to the acid group, - COOH.
R

+ (O)

KMnO4

 The excess carbon atoms and hydrogen atoms are oxidised to carbon dioxide and water.

+ [O]

+ H2O

CH2

+ 6[O]

+ CO2 + 2H2O

+9[O]

2 +2CO 2 + 3H2O

with milder oxidising agents such as acidified manganese(IV) oxide or acidified chromium(III) oxide, the side chain is oxidised to the aldehyde group, -CHO O

R
+ (O)

--

Benzaldehyde

 E.g:
CHO
+ 2[O]

+ H2O
Benzaldehyde

CH2CH3

CHO

+ 5[O]

+ CO2 + 2H2O
Benzaldehyde

i.

Reaction Involving the Aromatic Ring

The aromatic ring in methylbenzene is more reactive towards electrophiles that attacks the ring. Because the methyl group pushes electrons into the ring thereby increasing the electron density in the 2 (ortho) and 4 (para) position.
R R + E+
R

E + H+

+ H+
E

Halogenation
If chlorine is bubbled through methylbenzene in absence of sunlight, but presence of anhydrous aluminium chloride ( as halogen carrier) 2-chloromethylbenzene and 4chloromethylbenzene is form.
CH3 CH3
AlCl3 Room temperature

Cl + HCl

2-chloromethylbenzene

CH3

+ H 2O
Cl
4-chloromethylbenzene

 This is because the positive inductive (+I) effect

of the methyl group increases the electron charge density of the benzene ring more strongly at the 2- and 4- position. Further chlorination produces 2,4 dichloromethylbenzene.

CH3 Cl

Cl
2,4- dichloromethylbenzene

 The mechanisms are exactly the same as the substitution of chlorine into benzene
Step 1: - production of electrophile

 Step 2 :
- formation of carbocation
- when the electrophile attacks the ring, a carbocation is form which is a resonance hybrid of three structure. Ortho attack:
CH
3

CH3

CH3 Cl H Cl H

CH3 Cl + H

Cl+

3O (favourable)

2O (favourable)

2O (unfavourable)

step 3: loss of a proton to restore the stable aromatic ring

CH3 Cl

+ H+

2 - dichloromethylbenzene

Para attack:
CH
3

CH3

CH3 + + H Cl

CH3

+ Cl+
Cl
2O

+ H
3O

Cl

(favourable)

2O

Step 4 : loss of a proton to restore the stable aromatic ring

4- chloromethylbenzene

The reaction mechanism can be summarised as follow.

CH
3

CH3

CH3 Cl AlCl4Cl + HCl +AlCl3

+ Cl+

The reaction mechanism can be summarised as follow.

Nitration
Methylbenzene reacts with the mixture of conc. Nitric acid and conc sulphuric acid at 300C to produce 2-nitromethylbenzene.
CH3 CH3
Conc HNO3 + Conc H2SO4

NO2 + H 2O
2- nitomethylbenzene

30oC

CH3

+ H 2O
NO2
4 - nitomethylbenzene

 If the temperature is raised, 2

or 3 nitro groups, NO2 are introduced
CH3 NO2 O 2N CH3 NO2

NO2
2,4- dinitromethylbenzene

NO2
2,4,6- trinitromethylbenzene or TNT

Reaction with CH3I/AlCl3 ( Friedal-Crafts Alkylation)

When methylbenzene is added to iodomethane,CH3I in AlCl3 under anhydrous conditions at 200C A mixture of 1,2-dimethylbenzene and 1,4 dimethylbenzene is form CH3 CH3
+ CH3I
AlCl3 30oC

CH3 + H+
1,2- dimethylbenzene

CH3

+ H+
CH3
1,4 - dimethylbenzene

Reaction with CH3COCl/AlCl3 ( Friedal-Crafts Acylation)

This is involves substitution of an acyl group, RCO-, for a hydrogen atom on the aromatic ring in the presence of aluminium chloride White fumes of hydrogen chloride are given off CH3 CH3 O
+ CH3CCl
AlCl3 30oC

O CH3 + HCl

CH3

+ HCl

C CH 3

Reaction with SO3

When methylbenzene is added to fuming HsSO4 containing SO3 at 00C A mixture of 2-methylbenzenesulphonic acid and 4-methylbenzenesulphonic acid is obtained
CH3 CH3
+ SO3
Fuming H2SO4 0oC

SO3H + H+

CH3

2- methylbenzenesulphonic acid

+ H+
4- methylbenzenesulphonic acid

SO3H

The effect of substituent group on the benzene ring

When benzene ring contains a substituent X, the reactios of C6H5-X may be faster or slower. If X releases electron into the ring, then in benzene. X is said to activate the ring. E.g: in methylbenzene, the CH group increases the electron density of the benzene ring and therefore activates the ring, hence, methylbenzene reacts faster then benzene

 Electron releasing groups (which are ring activating) include: i. those that have an unshared par of electrons on the atom bonded to the ring which can be delocalised into the ring by extanded bonding -E.g
O
H

ii. Those without unshared pair but are electron-donating by induction,eg. Alkyl group. iii. Those with an attached atom participating in an electron-rich bond .e.g
C=C
And

Uses of Toluene
Toluene is a common solvent, able to dissolve: paints, paint thinners, many chemical reactants, rubber, printing ink, adhesives (glues), lacquer, leather tanner, and disinfectants. It can also be used as a fullerene indicator, and is a raw material for toluene diisocyanate (used in the manufacture of polyurethane foam) andexplosive trinitrotoluene (TNT). Industrial uses of toluene include dealkylation to benzene and disproportionation to a mixture of benzene andxylene. When oxidized it yields benzaldehyde and benzoic acid, two important intermediates in chemistry.

 It is also used as a carbon source for making Multi-Wall carbon nanotubes. Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments. Toluene can be used as an octane booster in gasoline fuels used in internal combustion engines. Toluene at 84% by volume, fueled all the turbo Formula 1 teams in the 1980s.

 Phenol, dikenali juga sebagai karbolik asid. Ialah terbitan-terbitan hirokarbon aromatik dalam mana satu atau lebih atom-atom hidrogen nukleus benzena telah digantikan oleh kumpulan-kumpulan hidroksil sepadan bilangannya. Fenol diterangkan sebagai monohidrik, dihidrik dan lain-lain mengikut bilangan kumpulan-kumpulan hidroksil yang melekat pada nukleus. Fenol (monohidrik) terbitan dari benzena dengan menggantikan satu atom hidrogen dengan satu kumpulan hidroksil. Mempunyai formula C6H5OH.

Phenol

Properties of phenol
Membentuk hablur (takat lebur 430C) tidak berwarna dengan berbau manis yang sangat istimewa Sangat beracun dan menyebabkan melecur bila disentuh dengan kulit. Sedikit acidic: molekul phenol mempunyai kecenderungan yang lemah utk membebaskan H+ ion daripada kumpulan hidroksil.

 Phenol mempunayai takat didih yang tinggi disebabkan oleh ikatan intermolecular hydrogen. Agak larut dalam pelarut organik Mempunyai kelarutan yang rendah di dalam air disebabkan kumpulanOH dalam phenol membentuk ikatan hydrogen pada air, manakala benzene ring mengurangkan kelarutan disebabkan terbentuknya daya van der Waals forces yang lemah di antara molecules lain.

Kegunaan fenol
Phenol merupakan bahan kimia industri yang penting. Lebi daripada fenol industri digunakan dalam pengeluaran fenol dan plastik Bahan perantaraan dalam mebuat nilon, aspirin, pembunuh runput-rampai dan bahan-bahan pencelup Sejenis penghapus hama(germicide) yang kuat

Manufacture of aspirin
The reaction id carried our by allowing sodium phenoxide to absorb carbon dioxide to form sodium phenyl carbonate The reaction of salicylic acid with ethanoic anhydride yields the pain reliever, aspirin

Antiseptic & disinfectants

They both kill germs. Antiseptic can applied to the skin while disinfectants are normally applied only to surfaces as they irritate the skin. Phenol is disinfectants but causes blistering of the skin However, its derivatives have both better germicidal properties and are safer to use as antiseptics

Manufacture of nylon 6,6

Nylon is synthetic fibre, is a condensation polymer, It is used to make nylon stockings and tights, nylon ropes, nylon bearings and carpets.

How does the -OH group modify the ring reactions?

Activation of the ring
The -OH group attached to the benzene ring in phenol has the effect of making the ring much more reactive than it would otherwise be. One of the lone pairs on the oxygen atom in the -OH group overlaps with the delocalised ring electron system.

giving a structure rather like this:

The donation of the oxygen's lone pair into the ring system increases the electron density around the ring.

REACTIONS OF PHENOL
I. Combustion of phenol
Phenol burns in a plentiful supply of oxygen to give carbon dioxide and water.

Phenol tends to burn in air with an extremely smoky flame - full of carbon particles.

REACTIONS OF PHENOL IN WHICH THE O-H IS BROKEN

The Acidity Of Phenol - suatu asid yang sangat lemah dan larutan berairnya
tidak mempengaruhi litmus - phenol agak terurai dalam air membentuk ion phenoxide ion dan hydroxonium ion.

C6H5OH + O2H

C6H50- + H30+

 Fenol agak senang larut dalam sodium hydroxide solution daripada dalam air
C6H5OH + NaOH
phenol

C6H50- Na+ + H20

Sodium phenoxide

lebih lemah daripada asid karbonik, H2CO3. tidak bertindak balas dengan carbonate ion, CO32to give carbon dioxide, CO2 Phenol adalah lebih kuat dari ethanol

Reaction with sodium

Phenol reacts vigorously with sodium to form sodium phenoxide and hydrogen

+ Na the

O-Na+ + H2

greater reactivity (in comparison to ethanol) is due to the weak acidity of phenol

Reactions of phenol involving the benzene ring

Phenol undergoes electrophilic substitution reaction more readily then benzene-the same reaction occuring more rapidly. more substitution taking place under the same conditions and less vigorous conditions being required for the same reaction.

 The hydroxyl group, -OH increase the electron density of the benzene orbitals considerably, enhancing the reactivity of phenol towords electrophiles The C-O bond in phenol has some double bond character. This is caused by the partial delocalisation of the lone pair of electrons in the oxygen atom into the benzene ring The increased charge density is greatest at the 2-,4and 6-position on the ring

Reaction with bromine

Aqueous phenol decolorise bromine water at room temperature to form a white precipitate of 2,4,6-tribromophenol. No halogen carrier is needed for this reaction.
Br

+ 3Br2/H2O
Br

Br

+ 3 HBr

2,4,6-tribromophenol

The reaction is faster in water due to the presence of the phenoxide ions, C6H5O-. In non-polar solvent the molecules are the reacting species. This reaction can be used as a simple test for the presence of phenol

Reaction with nitric acid (nitration)

Dilute nitric acid will react with phenol at room temperature to give 2nitrophenol(70%) and 4-nitrophenol.

+ HNO3

NO2

and 2-Nitrophenol
NO2

+ H2O
4-Nitrophenol

compare

this with benzene, where heating with a mixture of concentrated nitric acid and concentrated sulphuric acid is required for nitration.

Reaction with Acyl Chloride

Acyl chlorides, RCOCl and aryl chlorides,ArCOCl, react readily with phenol in alkaline solution to form esters
+ NaOH Sodium phenoxide

CH3 C Cl +
Ethanoyl chloride Phenol Phenyl methanoate (ester)

O ll

does not react with carboxylic acids to form esters

Reaction with iron(III) chloride test for phenol

Phenol produces an intense purple colour when treated with neutral irom(III) chloride. The colour is due to the presence of complex ion in which phenol forms dative bonds to iron.
3C6H5OH OH + FeCl3 (C6H5O)3 Fe + 3H+ + 3Cl-

Reduction of Phenol
Phenol can be reduces to benzene by heating it with zinc dust at 4000C
+ Zn + ZnO

BENZOIC ACID
Benzoic acid, the simplest aromatic carboxylic acid containing carboxyl group bonded directly to benzene ring Molecular formula C6H5COOH a white, crystalline organic compound. melting at 122 C (starting sublime at 100 C); boiling at 249 C. slightly soluble in water, soluble in ethanol, very slightly soluble in benzene and acetone. Its aqua solution is weakly acidic. It occurs naturally in many plants and resins. Benzoic acid is also detected in animals

Uses of benzoic acid

Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. It is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications. It is used as a rubber polymerization activators and retardants. Benzoic acid is converted to its salts and esters for the use of preservative application in foods, drugs and personal products. Sodium benzoate, sodium salt of benzoic acid, is used preferably as one of the principal antimicrobial preservatives used in foods and beverages (but it's concentration is limited usually not exceeding 0.1% because it is poisonous)

 Sodium Benzoate is also used in medications, anti-fermentation additives and tabletting lubricant for pharmaceuticals. The industrial applications are as a corrosion inhibitor, as an additive to automotive engine antifreeze coolants and in other waterborne systems, as a nucleating agents for polyolefin, as a dye intermediate, as a stabilizer in photographic processing and as a catalyst. Wide range of benzoic esters are used as solvents, dying carrier, disinfectant additive, penetrating agent and pesticides and manufacturing other compounds.