RECOVERY AND REUSE OF ETHYL ACETATE IN

RANITIDINE PROCESS

St. Joseph’s College of Arts and Science (Autonomous)

Cuddalore – 1.
In partial fulfillment of the requirements of the award of the degree of

BACHELOR OF SCIENCE IN CHEMISTRY

Submitted by

M. KOWSALYA
Reg. No: A15CHE23

Mr. S. IMMANUEL M.Sc., B.Ed., M.Phil.,

DEPARTMENT OF CHEMISTRY

ST. JOSEPH’S COLLEGE OF ARTS AND SCIENCE (AUTONOMOUS)

CUDDALORE – 607 001

APRIL – 2018
 CERTIFICATE

This is to certify that this project entitled (RECOVERY AND REUSE OF

ETHYL ACETATE IN RANITIDINE PROCESS) preparation of submitted to
St. Joseph’s College of Arts and Science (Autonomous) in partial fulfillment for
the award of the Degree of Bachelor in Science in Chemistry is a bonafide record
of word carried out by M. KOWSALYA (Reg. No: A15CHE23) under my
guidance of the academic period 2015 – 2018.

Head of the Department Project Guide

Principal

Submitted for viva – voce examination held on ……………

Signature of the Examiner

1………………….….. 2………………………..
 ACKNOWLEDGEMENT

I am especially grateful to thank our secretary Rev. Fr. G. PETER

RAJENDRAM, M.A., M.Sc., M.Ed., M.Phil., for his devotion to his students’
education and success.

I would never have been able to finish my dissertation without the guidance
of out Head of the department, Mr. A. AMALORPAVADOSS, M.Sc., B.Ed.,
M.Phil., for extending an excellent moral support.

I have had the great pleasure on my project under the guidance and supervision of
my internal guide, Mr. S. IMMANUEL M.Sc., B.Ed., M.Phil., Asst. Professor,
Department of Chemistry, St. Joseph’s College Arts and Science
(Autonomous), Cuddalore for suggestions and motivation is getting this
dissertation completed.

Without the support, patience and guidance of the following people, this
study would not have been completed. It is to them that I owe my deepest
gratitude. Over the past twenty years, I have received love, support and
encouragement from my parents, D. MURUGAN and M. RAJESHWARI have
sustained me throughout my life.

Finally I thank my fellow friends. They were always supporting me and

encouraging me with their best wishes.

KOWSALYA. M
(Reg. No: A15CHE23)
 DECLARATION

I hereby declare that this project entitled (RECOVERY AND REUSE OF

ETHYL ACETATE IN RANITIDINE PROCESS) of submitted to the St.
Joseph’s College Arts and Science (Autonomous), Cuddalore – 607 001, in partial
fulfillment of the requirement for the award of the degree of Bachelor of Science in
Chemistry is a record of original project work done by me under the supervision
and guidance of Mr. S. IMMANUEL M.Sc., B.Ed., M.Phil., Asst. Professor in
Chemistry, St. Joseph’s College Arts and Science (Autonomous), Cuddalore – 607
001and the project has not formed the basis for the award of any Degree / Diploma
/ Associateship / Fellowship or other similar titled to, any candidate of any other
University.

Signature of the candidate

KOWSALYA. M
(Reg. No: A15CHE23)
CONTENT
 CONTENT

CHAPTER
NO TITLE
1 INTRODUCTION

2 AIM AND SCOPE

3 MATERIALS AND METHODS

4 RESULTS AND DISCUSSION

5 CONCLUSION

6 REFERENCE
 PROFILE OF SHASUN CHEMICALS AND
DRUG LIMITED

 In 1976 incorporated as private limited company – “ Shasun Chemicals

(Madras) Private Limited” – at Chennai in South India.

 Shasun is derived from the name of the founder, late Shri. Shanakail Jain
and his wife Smt. Sundaribai.

 Shasun means ‘Leadership’ in Hindi.

 Shasun is a leading India manufacturer of active pharmaceutical

ingredients and their intermediates.

 Shasun has created a strong product portfolio, building on its R&D

expertise, regulatory capabilities and large scale production capacities.

 In 1977 – First production facility established at Velachery, Chennai for

manufacture of Analgin (anti – pyretic) with a capacity of 3 MT per month.

 In 1986 – Second production facility established at Pondicherry for

manufacture of ibuprofen (anti – inflammatory) with a capacity of 5 MT.

 In 1991 – Third production facility established at Cuddalore for manufacture

of Ranitidine HCI (anti – ulcerative).

 Ibuprofen capacity at Pondicherry increased to 40 MT per month.

  In 1992 – Converted into Public Limited Company.

 Name of the Company changed to “Shasun chemicals And Drug Limited”.

 In 1993 – Ibuprofen production capacity increased to 3,000 MT per year

none of the largest in the world.

 In 1999 – Ranked first among Indian pharmaceutical companies based on

performance index by the Economic Times.

AWARDS RECEIVED

 In 1993 received the prestigious “Trishul” award for exports during 1990 –
91 from CHEMEXCIL (Export Promotion Council, Government of India).

 In 1996 – ISO 9002 certification from BVOI

 Awarded ‘Certificate of Merit’, for outstanding export performance during

1993 – 94 by CHEMEXCIL.

 In 1999 IAO 9002 re – certification form BVOI

LEADERSHIP IN ACTION

From a modest beginning in 1976, Shasun has acquired a worldwide

reputation for the manufacture of Active Pharmaceutical Ingredients (APIs) and
their intermedited. The Company’s products are exported to customers in more
than forty countries across Europe, North America, and Latin America & Asia.
 Shasun is one of the largest producers of Ibuprofen worldwide. It is also one
of the major producers of Ranitidine in India. The company enjoys leadership
status in the anti – inflammatory and anti – ulcerative segments. Shasun is ranked
as major exports from India.

Shasun USA Inc., the U.S. subsidiary reflects Shasun’s increasing commitment
to international markets.

Recently, Shasun has entered into a partnership with Austin Chemical

Company, USA to undertake contract research and contact manufacturing for
multinational pharmaceutical companies. Shasun also has an ongoing partnership
with Chirotec, UK for manufacture of S-Napoxen, and with Nagase & Co., Japan
for manufacture of S+ Ibuprofen.

Shasun’s unique combination of high volume production, manufacturing

competitiveness, resource and expertise enables it to meet ever growing global
demands and expectations.

Shasun’s manufacturing units both at Pondicherry and Cuddalore boast of

modern well – equipped laboratories managed by experts, who monitor quality
during the entire manufacturing process, right form raw materials to finished
products.
 CUDDALORE FACILITY

Overview

 Multi product, CGMP complaint facility.

 Dedicated facilities for manufacture of products and intermediates.
 Largest exported from India for Ranitidine and its intermediates.
 Direct Compressible Ranitidine and its intermediates.
 Major exporter of Nizatidine & its intermediates.
 Manufacturing different polymorphs of Ranitidine to be must stringent
specifications in the world.
 Customers include Glaxo (India) and Glaxo welcome (Singapore), the
innovator of Ranitidine.
 Established in 1991.

Regulatory information

 USFDA inspected for Ranitidine and Nizatidine in June 1999.

 Presently the only USFDA inspected site for Nizatidine.
 Drug Master file (DMF) for Ranitidine field in USA, UK, Europe and
Autralia.
 CoS for Ranitidine HCI Form I obtained from EP.
Research & Development

Key features

 Working as a Contract Research organization.

 Plot plant facility.

 Fully equipped instrumentation laboratory.

 Capability to scale – up from gram to kilogram to multi – tons

 CGMP / non – CGMP products.

 Wide range of chemical synthesis capabilities. Especially for APIs and

their intermediated.

 Access to highly sophisticated instruments like NMR / X – Ray diffraction

etc.

 Well – stocked information Resource Centre with on-line search facility.

 A team of qualified doctorates and scientists working round the clock.

 Geared for regulatory inspection.

 Scaled – up three APIs and four intermediates to commercial production.

 Tie – up with Austin Chemical Co., USA.

 Shasun has field DMFs (Drug Master Files) in more than ten countries and has
also obtained the full – key regulatory approvals:

 European Certificate of suitability (CoS) for Ibuprofen & Ranitidine.

 Therapeutic Goods, Administration, Australia, Certificate for Ibuprofen and
Ranitidine.
 Medicine cannot Agency, UK for Ibuprofen.
 US FDA for Ibuprofen, Ranitidine and Nizatidine.

PRODUCT SPECIFICATION

Ibuprofen is intech class of drugs called Non – Steroidal Anti –

inflammatory Drugs (NSAIDs). Ibuprofen works by reducing hormones that cause
inflammation and pain in the body.

It is used to reduce the fever, pain, inflammation, and stuffiness caused by

many conditions, such as osteoarthritis, rheumatoid arthritis, and abdominal
cramps associated with menstruation.

Ranitidine is in a class of drugs called Histamine Receptor Antagonists,

Ranitidine works by decreasing the amount of acid your stomach products.

Ranitidine is used to treat and prevent ant ulcers in the stomach and
intestines, Ranitidine is also used to treat conditions in which the stomach
producers too much acid and conditions in which acid comes up into the esophagus
and causes heartburn, such as gastroesophagael reflux disease (GERD).
 Nizatidine is in a class of drugs called Histamine Receptor Antagonists.
Nizatidine works by decreasing the amount of acid your stomach produces.
It is used to treat and prevent ulcers in the stomach and intestines.
Nizatidine is also used to treat conditions in which the stomach produces too much
acid and conditions in which acid comes up into the esophagus and causes
heartburn, such as gastro esophageal reflux disease (GERD)

Strategy for the future

 Commercializing R & S products & get into long contracts.

 Exports of generics.
 With world class muff, facilities Shasun can leverage on low domestic
production cost to enter into sourcing arrangement with MNCs.
 Leverage on low cost advantage & storing chemical synthesis skills to enter
into collaborative research alliances with MNCs.
 Diversity into formulation business.
 Offering contract manufacturing for strategic partners.
 Wherever necessary acquire technologies for quicker to world markets.
Other Area

 Focus on enhancing knowledge asset by filling patents for won – infringing

processors.
 Focus on Biopharmaceuticals.
INTRODUCTION
 INTRODUCTION

My Project deals with “Recovery and reuse of ethyl acetate in Ranitidine

Process”

Ranitidine:-

It is a classes of drug called Histamine Receptor antagonists Ranitidine

decreases the secretion of HCl in stomach.

Ranitidine is used to treat and prevent from antiulcer in the stomach and
ranitidine is also used to treat conditions in which the stomach produces too much
acid and conditions in which acid comes up into the esophagus and cause heartbeat
such as gastro esophageal reflux disease.

History and therapeutic category:-

Ranitidine is a new histamine H2 receptor antagonist which unlike

cime6tidine that contains an imidazole ring has a furane ring structure. This
substituted amino-alkyl furane derivative is more potent than cimetidine in
inhibition o gastric acid secretion induced by various stimuli.

The drug has been used in the treatment of duodenal and gastric ulceration.
In the recommended dosage of 150 mg twice daily. Ranitidine is as effective as
cimetidine and has therefore the advantage of less frequent dosing and fever and
side effects.

Ranitidine appears to be the drug in treatment of zollinger – Ellison

syndrome. M The compound is given orally as a tablet (150 mg of ranitidine base )
and as an injection solution (50 mg/5ml).
 The first synthesis of ranitidine was report6ed in 1973 followed by
pharmacological and clinical studies in 1979 and 1980. Finally ranitidine was
introduced on to the market in 1981.

Chemical name:

The chemical name for ranitidine is N-[2-[[[5-[(dimethy1 amino) methyl]

methy1] thio] ethy1]-N-methyl-2-nitor-1, 1-ethane diamine.

Generic Name : Ranitidine

Trade Name : Zantac

Drug class : Histamine (H2) blocks

Available : Capsules, Tablets, injection, syrup, granules.

Why prescribed:

To treat ulcer of the stomach and duodenum conditions that cause increased
stomach acid production (such as zollinger-Ellision syndrome)

How it Works:

Ranitidine blocks the action of histamine which in turn decrease the stomach
secretion of HCl acid. Once stomach acid production is decreased, the body is
better able to heal itself.

Structure:
Molecular formulae : C13 H22N4O3S

Molecular weight : 314.41

Melting point : 69-70

Apperarance, colour and odour :

Ranitidine is marked only as the hydrocholoride salt. It is a white to

yellowish solid with little (or) No odour. A slight sulfer-mercaptane odour may be
present.

Range of frequency :

Adults-Oral doles 150mg 2 times daily in the morning and at bedtime (or)
300 mg once daily before bedtime.

Injuction:

 50 mg/ 5ml every 6 to 8 hours.

 Patinents with zollinger-Ellision syndrome may require upto 6g per day taken
oraly.

Storage:

 Store away from heat and direct light.

 Keep liquid form freezing.
 Avoid liquid form freezing.
 Avoid alcohol, ranitidine may increase blood alcohol levels.
 Ranitidine is not recommended for young patients although it has not been
shown to cause any side effects.

Overdose symptoms :

Vomiting, diarrhea,, breathing problems, rapid heartbeat, delirium.

Disease intractions :-

Patients with kidney disease should not use ranitidine (or) should use it in
smaller or limited. Doses under careful supervision by a physician.

Concept :-

In the production of ranitidine base, ethyl acetate is used as a solvent and it

was recover from ranitidine base mother liquid by following process.

Ethyl acetate is an ester. It is non-polar solvent and liquid at room

temperature. It is sparingly soluble in water but liberally miscible with organic
solvent. Hence it is used as a very good elevent in chromatographic techniques
and a good solvent is drug industry.

Ethyl acetate becomes unstable only in presence of strong oxidizing agent

and strong alkalies. Its boiling points is 77c, it can be easily recovered and reused
in my project.

The mother liquid is effluent left from the production of ranitidine base. It
combines mostly of ethyl acetate CHCl3, and little bit of Ranitidine base. The
effluent is directly dumped in to the effluent treatment plant.

The cost of ethyl acetate for 1 litre is 42Rs. Ethyl acetate required for one batch
800 litre. About two to three batches are moving per day.

So because for this requirement and high cort, I done my project work on
recovery and reuse of ethyl acetate.
Ethyl Acetate :-

Ethyl acetate also known as acetic acid ethyl ester, ethyl ethanoate, acetic
ether of acetic ester, is a clear, flammable liquid with a characteristic, not un
pleasant smell like certain glues or nail polish removers. From the chemical point
of view it is an ester with formula : CH3COOHCH2CH3. It may be formed
(along with acetic acid) as a contaminate in wine that has been exposed to air.
Ethyl acetate is used as a solvent in glues and nail polish remover, in chemical
reactions, and for extractions.

Ethyl acetate is a non-polar (lipophilic) to weakly polar (hydrophilic) aprotic

solvent with an 8% solubility in water. Ethyl acetate is not stable in the presence
of strong aqueous bases and acids.

Chemistry of ethyl acetate :-

Ethyl acetate is an ester that is synthesized from acetic acid and ethanol in
the presence of strong acid like H2SO4 in an esterification reaction. The two
reactants and the H2SO4 Catalyst are heated under reflux for approximately 40 min.

H2SO4

CH3CH2OH + CH3COOH -------------------> CH3COOCH2CH3 + H2O

Heating
 The reaction is reversible and produces an equilibrium yield is low. Unless

driven to right by removal of water. The yield can also be increased by using an

avid chloride (CH3COCl), INSTEAD OF CARBOXYLIC ACID. This is usually

performed in the presence of a base such as pyridine (to remove HCl) and since in

does not result in equilibrium more of the ester is produced. It is unstable in the

presence of strong base like sodium hydroxide or strong acid like HCl and it is

hydrolysed back in to the ethanol and acetic acid especially at elevated

temperature.

Properties of ethyl acetate :-

Ethyl acetate is a colorless liquid. It is sparingly soluble in water but readily

soluble in organic solvents.

Esters generally are not very soluble in water, they are quite volatile as they

cannot undergo hydrogen bonding due to lack of - OH groups.

 Ethyl acetate can dissolve up to 3% water and has solubility of 8% in water
at room temperature. At elevated temperature its miscibility with water is much
higher. The refractive index of ethyl acetate is 1.370.

Physical Properties:-

Ethyl acetate

Systematic name Ethyl acetate

Other names Acetic acid ethyl ester ethyl
ethanoate acetic ester
Molecular formula C4H8O2
Molecular mass 8811g/mol
Appearance Clear, colorless liquid
Odour Pleasant fruity odour
Properties
Density and phase 0.897 g/cm2, liquid
Solubility in water 8.3g/100ml (200oC)
Solubility in ethanol, acetone, diethyl Miscible
ether, benzene
Melting point -83.60C (189.55K)
Boiling point 77.10C (335.25 K)
Critical temperature 250.110C (523.26 K)
Viscosity 0.426 at 250oC
Relative Polarity 0.228
Relative Density H2O =1 0.9
Specific gravity 0.902
Vapour Density (Air = 1) 3.0
Vapour pressure 76mm Hg
Auto ignition temperature 4270C
Explosive limits vol% in air 2.2 – 11.5
Dipole moment 1.78 D
Main hazards Flammable & Irritant
Flash point -40 C
Thermodynamic data Phase behavior Solid liquid, gas
Spectral data UV, IR, NMR, MASS
Related carboxylate esters Methyl acetate Butyl acetate
Related compounds Acetic acid

Chemical Properties :-

Ethyl acetate is a flammable liquid and an explosion hazard. It is slightly

soluble in water, but soluble in most organic solvent such as CHCl3, alcohol and

ether. It is flammable, dangerous fire and explosion risk. Moderately toxic by

inhalation and skin absorption. Irritating to eyes and skin.

Consumer products which may contain Ethyl acetate” : Some of the consumer

products containing ethyl acetate are automotive and machinery paints, inks,

lubricating oils, moisturizing creams, finger nail polish, enamels and removers,

paint thinners, premoistened towlettes, resin and rubber adhesives, and artificial

flavourings. It is found in wines.

Environmental effects :

1. Environmental Fate: Ethyl acetate evaporates to a gas if released as a

liquid. Ethyl acetate is a volatile organic chemical (VOC) and will
contribute to the formation of smog.

2. Environmental Transport: Industrial emission of ethyl acetate can

produce elevated, concentration in the atmosphere around the source. Ethyl
acetate that makes its way into the ground, and does not evaporate, will
eventually end up in the ground water.

3. Relative hazard to the environment: On an environmental spectrum of 0-

3 ethyl acetate registers 1. A score of 3 represents a very high hazard top the
environment and 0 a negligible hazard. Factors that are taken into account
to obtain this ranking include the extent of the material’s toxic or poisonous
nature and/ or its lack of toxicity, and the measure of its ability to remain
active in the environment and whether it accumulates in living organisms.
Uses of ethyl acetate:

1. Ethyl acetate is a very effective poison for use in insect collection and study
(entomology)
2. In a jar charged with ethyl acetate, the vapors will kill the collected (usually
adult) insect quickly without destroyed it.
3. Ethyl acetate is used as a solvent for varnishes, dry cleaning, stains fats and
nitrocellulose.
4. It is released during the production of artificial skin and leather and during
the preparation of photographic films and plates.
5. It is released during the production of artificial skin and leather and during
the preparation of photographic films and plates.
6. Ethyl acetate is used as a solvent in nail polish remover, base coats and other
manicuring products.
7. Used as solve in preparation of plastic, organic synthesis, smokeless
powders, pharmaceuticals drug and synthetic fruit essence.
AIM AND SCOPE
AIM AND SCOPE

AIM:-

The aim of the project is given below:

I. Preparation of Ranitidine base

II. To check the reusability of ethyl acetate in Ranitidine process

SCOPE:-

As we known that the usage of chemicals are maximum in industries, the cost of
chemicals are also increasing from day by day. Based on the above objectives we
can manage the usage of ethyl acetate economically in industries. It also reduces
the cost of product. The method impresses several chemist to put forward this idea
for possible products. This method is not a much difficult one, to follow and it is a
simplest method.
MATERIALS AND METHODS
 MATERIALS AND METHODS

Preparation of Ranitidine Base:

Raw Materials:
i) N-methyl, S-methyl nitro ethane (NMSM)
ii) Cystofur (RI2)
iii) Toluene
iv) Chloroform
v) Ethyl acetate
vi) Hexane
vii) Potassium Hydroxide
viii) Water
Process Flow chart:

Cystrofur Purified Water NMSM

Condensation reaction

Toluene

Washings

Toluene Layer

Potassium Hydroxide solution Aqueous layer

pH adjustment
CHCl3

Extraction
 Filtered organic layer

Aqueous layer

Distillation
ETHYL ACETATE

CHCl3 (Recovered)

Distillation
ETHYL ACETATE

CHCl3 + ETHYL ACETATE

COOLING MIXTURE

RANITIDINE BASE
CRYSTAL SLURRY

NITROGEN

FILTRATION

MOTHER LIQUID

CHILL ETHYL ACETATE HEXANE

Washings

Wet Ranitidine base

REACTION:

Process description:-

1. NMSM was first taken in RBF. To this water was added, followed by 10

min stirring. To this cystofur was added and stirred up to completion of

reaction.

2. Toluene was added to the mixture in rbf and stirred for 30 minutes. Allow

to settle down. Separate the organic layer and discard it. To the Aq. Layer

added toluene and stirred for 10minutes. Allow to settle down separate the

organic layer and Aq. Layer. Discard the organic layer.

3. To aq. Layer mass, KOH dissolved in water was added and adjust the P H to

10.5 and CHCl3 was added. Stirred the mixture for 30min than allow to

settle down. Separate the organic layer 1 and added CHCl3 to aq. layer,
 stirred separate the organic layer 2 discard the aq. layer, combine the organic

layer 1 and 2 and water was added. Stirred and separate the organic layer.

Distilled the organic layer in vacuum at temperature 490C.

4. Ethyl Acetate was added to the reaction mass to remove the traces of CHCl3

by distillation again chcl3 to the reaction mass and stir for 15 minutes. Cool

the mixture to 10-150C for 1 hour. Filter the mass, wet product formed.

5. The wet product was washed with chilled ethyl acetate and followed by

chilled hexane Died the product under nitrogen atmosphere at 30-350C,

ranitidine base product is crystallized.

Recovery of ethyl acetate:-

Ethyl acetate mother liquid is obtained from filtration of ranitidine base and

it was purified as follows

1. Vaccum Distillation:-

Into a 2lit RVF flask added 1500 ml of ethyl acetate mother liquid and set the

vacuum 180-190m bar and distill out completely at temperature range of 45-500C.

Ethyl acetate - 1430ml

Residue - 65ml

Vapour loss - 5ml

Atmospheric distillation:-

In to a liter single neak RBF added above recovery ethyl acetate 1430 and

by atmospheric distillation. Collect the ethyl acetate at different temperature.

Fraction Temperature Volume collection

I 74-760c 130ml

II 76-770C 1020ml

III 77.5-780C 150ml

IV Residue 60ml

V Vapour loss 70ml

RESULTS AND DISCUSSION
RESULTS AND DISCUSSION :-

The analysis of second fraction is given below

Moisture content – 0.26 %

GC Result:-

1. Ethyl acetate - 99.05%

2. Toluene - 0.63%

3. Chloroform - 0.23%
Preparation of Ranitidine base : -

(i) Preparation of Ranitidine base using Fresh Ethyl acetate :

Preparation of Ranitidine base and process description as

described above and crystallization using fresh ethyl acetate.

Sl. No Batch size Analytical Report Remarks

Input : 50 g LOD - 0.09 % 1. Fresh ethyl

Trail 1 Output : 58 g M. pt - 71.8oC acetate used for –

IR - Complies crystallization

2. Filtration to be

carried out in

nitrogen atm.
(ii) Preparation of Ranitidine base using Recovery ethyl acetate

Preparation of Ranitidine base and process description are described

above and crystallization using Recovery ethyl acetate.

SL. No Batch size Analytical Report Remarks

Trail 2 Input : 50 g LOD - 0.10 % 1. Recovery ethyl

Output : 57 g M. pt - 72oC acetate used for

IR - Complies crystallization.

2. Filtration to be

carried out in

Nitrogen atm.
CONCLUSION
 CONCLUSION

The recovery of ethyl acetate during the preparation of ranitidine base and

reuse of the same has the following advantage.

i. The ethyl acetate obtained from ranitidine process cannot be

reused. Because it has impurities and the purity one 99.09%. But the generated

ethyl acetate can be reused after purification.

ii. The purity of ethyl acetate after distillation is 99.99%

iii. The ethyl acetate is important raw material of ranitidine process.

iv. So finally we conclude that this project is a good satisfactory

method and useful of our life.

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- Mercky index

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By Kalsi

- Roberts, Journals of the society of chemical industry.

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- smprimer/gc/gc.html

- Analytical chemistry

By Gopalan

- Organic Chemistry

Y.R. SHARMA

- Organic Chemistry

Paul And Arunpaul

- Google.com

- Ranitidine in pharmaceutical Industry