ORGANIC CHEMISTRY

TITLE :- TO STUDY THE MONOGRAGH OF BENZOIC ACID AS PER INDIAN

PHARMACOPOEIA

BENZOIC ACID :

Molecular formula : [C7H6O2]

Molecular weight : 122.12

Category : antifungal agent; pharmaceutical aid (anti-microbial

preservatives).

Description: Colorless; light crystals, scales or neddles; slight and

characteristics.

Solubility: freely soluble in ethanol (95%),in chloroform and in ether ;

slightly soluble in water but soluble in boiling water. it is soluble in fixed oils.

Storage: store in well closed containers

STANDARDS:

Benzoic acid contains not les than 99.5%and not more than 100.5%0f
C7H6O2. Calculate with reference to the anhydrous substance.

Identification: A: warm gently 0.2g with 20ml of water , add 1ml of 1M

sodium hydroxide and filter . To the filterate add ferric chloride test solution ;
a buff colored precipitate is produced.

B : The light absorption in the range 220 to 360 nm of a 0.001% w/v solution
in methanol exhibits a maximum only at about 225nm; absorbance at about
225nm, about 0.8.
C: 1% w/v solution is acid to methyl red solution.

D: melts between 121 to 123 degree centigrade.

SYNTHESIS OF BENZOIC ACID:-

Hydrolysis of benzamide produces ammonia by the addition of either akali
salts of the acid and librate the organic acid

C6H5CONH2 + H2O  C6H5COOH + NH3

1: 1g of benzamide and 15ml of 10% aqueous sodium hydroxide solution in

100 ml of conical flask fitted with a reflux water condenser , and boil the
mixture gently 30 minutes, during which period ammonia is evolved.

2: Now cool the solution in ice water, and add concentrated HCL until the
mixture is strongly acidic.

3: Benzoic acid immediately separates.

4: Allow the mixture to stand in the ice water for a few minutes, and the filter
off the benzoic acid at the pump with cold water,and drain.

5: Recrystalline from hot water.

6: The benzoic acid is obtained as colorless crystals, melting point 121 degrre
centigrade, almost insoluble in cold water.

CHEMICAL TESTS :-
1 Clarity and color of solution :

5% w/v solution in ethanol (95%) is clear and colorless.

2 limit test for Arsenic:

Mix 5g of with 3g of anhydrous sodium bicarbonate ,add 10ml of bromine

solution and mix thoroughtly. Evaporate to dryness on a water bath, gently
ignite and dissolve the cooled residue in 16ml of brominated hydrochloric
acid and 45ml of water. Remove the excess of bromine with 2ml of stannous
chloride AsT. The resuting solution complies with the limit test for arsenic
(2ppm).

3 limit test for Heavy metals:

Not more than 10ppm , determined by the following method. Dissolve 2.0g in
25ml of acetone and add 2ml of water and 10ml of hydrogen sulphite solution
; any color produced is more intense than that of a solution prepared with
25ml of acetone , 2.0ml of lead standard solution (10ppm lead) and 10ml of
hydrogen sulphite solution.

4 Readily oxidisable substances:

Add 1ml of sulphuric acid to 100ml of wate, heat to boiling and add dropwise
0.1M poytassium permagnate until the pink color is persists for 30 seconds .
Dissolve exactly 1g of in the hot solution and titrate with 0.1M potassium
permagnate to a pink color that persists for 15 seconds ;not more than 0.5 ml
of 0.1M potassium permagnate is required .

5 Cinnamic acid:

Warm 0.1g with 0.1g of potassium permagnate and 5ml 0f dilute sulphuric
acid; no odour of benzaldehyde is developed.

6 limit test for Chlorinated compounds:

Dissolve 0.33g in 5 ml of 0.5ml of 0.5M sodium carbonate ,evaporate to

dryness and heat the residue until completely charred, keeping the
temperature below 400 degreee .Extract the residue with a mixture of 10ml 0f
water and 12ml of dilute nitric acid and filter; the filtrate complies with the
limit test for chlorides.
PROCEDURE FOR LIMIT TEST OF CLOHRIDES :

TEST SOLUTION STANDARD SOLUTION

SPECIFIC WEIGHT OF COMPOUND IS TAKE 1 ML OF 0.05845% W/V SOLUTION
DISSOLVED IN WATER OR SOLUTION IS OF SODIUM CHLORIDE IN NESSELER
PREPARED AS DIRECTED IN THE CYLINDER
PHARMACOPOEIA AND TRANSFEREDIN
NESSLER CYLINDER

ADD 1 ML OF NITRIC ACID ADD 1 ML OF NITRIC ACID

DILUTE TO 50 ML IN NASSLER CYLINDER DILUTE TO 50 ML IN NASSLER CYLINDER

ADD 1 ML OF AGNO3 SOLUTION ADD 1 ML OF AGNO3 SOLUTION

KEEP ASIDE FOR 5 MINUTES KEEP ASIDE FOR 5 MINUTES
OBSERVE THE OPALESCENCE /TURBIDITY OBSERVE THE OPALESCENCE/ TURBIDITY

ASSAY PROCEDURE FOR BENZOIC ACID :

Principle : ACID BASE TITRATION

Weigh accurately about 1.0g and dissolve in 15 ml of warm ethanol (95%)

previously neutralized to phenolphthalein solution. Add 20ml of water and
titrate with 0.5M sodium hydroxide using phenolphthalein solution as
indicator. Each ml of 0.5M sodium hydroxide is equivalent to 0.06106 g of
C7H6O2.

ASSAY CALCULATION :

SR.NO VOLUME BUERETTE READING (Ml) INDICATOR

OF
TITRAND

1 30ml INITIAL FINAL DIFFERENCE CONCONDENCE PHENOLPHTHALEIN

0 10 10 10
 𝑴×𝑽×𝑭×𝟏𝟎𝟎
𝑾×𝑴
%PURITY =

𝟎.𝟓×𝟏𝟎×𝟎.𝟎𝟔𝟏𝟎𝟔×𝟏𝟎𝟎
%PURITY = 𝟏.𝟎×𝟎.𝟓

%PURITY = 61.06%
RESULT AND OBSERVATION :-

S.NO TEST OBSERVATION

1 LIMIT TEST FOR ARSENICS PASS

2 CLARITY AND COLOR OF CLEAR AND COLORLESS
SOLUTION
3 LIMIT TEST FOR HEAVY PASS
METALS
4 READILY OXIDISABLE PASS
SUBSTANCES
5 CINNAMIC ACID NO ORDER OF
BENZALDEHYDE
6 LIMIT TEST FOR CLORINATED TURBIDITY APPEARS
COMPOUNDS
7 SULPHATED ASH PASS

MATERIAL SAFETY DATASHEET:-

1. Sulphuric acid :-
Synonym:- oil of vitriol; sulphuric acid.

Hazards identification:- Very hazards in case of skin contact, of eye contact,

of ingestion, of inhalation.
Liquid or spray mist may produce tissue damage particularly on mucus
membrane of eyes, mouth and respiratory tract.

Eye contact may produce burns.

Inhalation of the spray mist may produce severe irritation of respiratory tract.

Hazards Pictogram :-

First aid measures:-

General advice – show this safety datasheet to the doctor in attendance.

Immediate medical attention is required.

Eye contact – rinse immediately with plenty of water , also under the eyelids,
for at least 15 minutes. Immediate medical attention is required.

Skin contact – wash off immediately with plenty of water for at least 15
minutes. remove and wash the contaminated clothing and gloves.

Ingestion:- Do not induce vomiting. Never give anything by mouth to an

unconscious person. Call a physician or poison control center immediately.

Handling and storage:-

Handling – Wear personal protective equipment/face protection. Do not get

in eyes, on skin or on clothing. Use only under a chemical fume hood.

Storage :- keep containers tightly closed in a dry, cool and well – ventilated
place. Keep away from water or mist air. Corrosive area.

2 . Hydrochloric acid:-

Synonym:- muriatic acid, chlorohydric acid , spirit of salt.

Hazards statement :-Causes severe skin burns and eye damage.

Causes serious eye damage.

Harmful if swallowed.

Causes damage to organs through prolonged or repeated exposure (teeth).

Hazards pictograms :-

First aid measures:-

Ingestion – Do not induce vomiting. If victim is conscious and alert, give 2-4
cup full of milk. Consult a doctor immediately.

Inhalation – Remove patient in fresh air. Administer approved oxygen spply

if breathing has ceased. Get medical intention immediately.

Eyes – immediately flush eyes with large amount of water for atleast 30
minutes holding lids apart to ensure flushing of the entire surface.

Skin – immediately flush skin with copious quantities of water for atleast 15
minutes while removing contaminated and clothing and shoes.

Handling and storage: –

Handling –

wash thoroughtly after handling .use with adequate ventilatin. Do not get in
skin or eyes. Do not ingest or inhale.

Storage –

keep away from heat or flame . Do not store in direct sun light. Store in a cool,
dry and ventilated area. keep tightly closed.
3 . Ammonia :-

Synonym :- salts, spirits and vapours

Hazards statement :- causes severe skin burns and eye damage.

May cause respiratory irritation.

Very toxic to aquatic life.

Pictograms :-

First aid measures :-

After inhalation- move exposed individual to fresh air. Seek medical advice
if discomfort oe irritation persists.if breathing difficult , give oxygen.

After skin contact :- Wash affected area with soap and water . rinse/flush
exposed skin gently using water for 15-20 minutes. seeek medical advice .

After eye contact :- Protect unexposed eye . rinse/flush exposed eye (s)
gently using water for 15-20 minutes.

After swallowing :- rinse mouth thoroughtly. Do not induce vomiting. Have

exposed individual drink sips of water. Seek medical attention.

Handling and storage :-

Handling –

wash hands after handling. Follow good hygiene procedures when handling
chemical materials. Do not eat, drink, smoke, or use personal products .

Storage :-
provide ventilation for containers. Avoid storage near extreme heat, ignition
sources or open flame. Store in dry, cool conditions in well sealed containers.

4. benzamide :-

Synonyms :- 3 amino benzamide.

Hazards statement :- Harmful if swallowed.

Causes skin irritation.

Causes serious eye irritation.

May cause respiratory irritation.

Pictograms :-

First aid measures :- symptoms of poisoning may even occurs after several
hours; therefore medical observation for atleast 48 hours after the accident.

After inhalation :- In case of unconsciousness place patient stably in side

position for transportation.

After eye contact :- Rinsed opened eye or several minute is under running
water. If symptoms persists, consult a doctor.

After skin contact :- Immediately wash with water and soap and rinse
thoroughtly.

After swallowing :- Immediately call a doctor.

Handling And Storage :-

Handling – Wear personal protective equipment/face protection .ensure
adequate ventilation.

Avoid contact with skin , eyes or clothing . avoid dust formation.

Storage:- Keep containers tightly closed in a dry, cool and well – ventilated
place.

Strong oxidizing agents. Strong bases.

IR SPECTRA OF BENZOIC ACID:-

IR VALUES:-

SR.NO GROUP NAME REFERENCE VALUE

1 OH STRETCH 3500-2500
2 OVERTONE AND COMBINATION BANDS 2800-2500
3 C=O STRETCH 1709
4 C-O STREACH 1230
5 OUT OF PLANE OH BEND 942