final project of msc ii

7/29/2019 Final Project of Msc II

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A PROJECT ON

SYNTHESIS OF ORGANIC PRODUCTS

SUBMITTED BY

SURALKAR PUSHPA JANARDAN

STUDENT OF

M.Sc-II ORGANIC CHEMISTRY

AFFILATED TO

UNIVERSITY OF MUMBAI

K.J.SOMAIYA COLLEGE OF SCIENCE & COMMERCE

VIDYANAGAR, VIDYAVIHAR, MUMBAI-400 077

YEAR : 2012-2013


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PROJECT REPORT

NAME :- PUSHPA JANARDAN SURALKAR SUBJECT :- ORGANIC CHEMISTRY(PART II)INSTITUTION :- K.J. SOMAIYA COLLEGE OF SCIENCE &

COMMERCE, VIDYAVIHAR(E)

MUMBAI -400077

YEAR :- 2012-2013 TEACHER INCHARG :- Mrs. SNEHAL VAIDYA TITLE OF PROJECT :- SYNTHESIS OF

1) 2-BROMOPYRIDINE,

2)4-ACETOXY METHYL BENZOATE

3) ASPIRINE

LOCATION :- OMKAR SPECIALITY CHEMICALS PVT.LTD, BADLAPUR.

DURATION :- 30th OCTOBER to 22ndNOVEMBER

SIGNATURE OF TEACHER:

SIGNATURE OF HEAD OF THE DEPARTMENT:

SIGNATUREOF EXAMINAR:


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ACKNOWLEDGEMENTI wish to express my sincere thanks to our Principal Dr. Vijay Joshi, Vice principal Dr.

Verma and Mrs. AshaRao Head of Chemistry department for giving me the permission to work

withOmkar Chemicals and having a close exposure to the industrial work.

I own my deepest gratitude to the teachers of chemistry department especially Mrs.

SnehalVaidya. This project could not be possible without their encouragement.

I wish to express my heartfelt thank to the management ofOmkar Chemicals Pvt.Ltdfor giving

me an opportunity to work their Reputed firm and helping me to complete my training

successfully

It was my honor to work under Mrs. KetakiDurve (Head of Department) and all the analyst at

Omkar Chemicals. My sincere thanks to Mr. Mahesh Gaidhane& Mrs. Swati Mane for their

constant support and guidance during my training and who spared his valuable time in helping

me to compile all the information for the project

..Lastly, I would thank all my friends for their constant motivation and support.

Sincerely

Suralkar pushpa


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K.J. SOMAIYA COLLEGE OF SCIENCE AND COMMERCE(Reaccredited by NAAC with Grade A with CGPA 3.21)

Vidyavihar (East), Mumbai - 400077

CHEMISTRY DEPARTMENTCERTIFICATE

This is to certify thatSURALKAR PUSHPA of M.Sc-II (Organic Chemistry) has successfully

completed the Industrial Project from 30TH

October 2012 to 22ND

November 2012 atOMKAR

SPECIALITY CHEMICALS,BADLAPUR, as per syllabus in Organic Chemistry for M.Sc-II,

prescribed by the University of Mumbai during the academic year2011-2012.

Signature of Project In charge

Date:

Head of Chemistry Department

Date:

Signature of Examiner

Date:


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ABSTRACTAs a chemist it is very important to study and apply the chemical principle to th

industrial application. I got this opportunity during my project training in M/s OMKA

Speciality Chemicals Ltd., Badlapur. I observed and studied the manufacturing processe

different problems faced and solutions for those problems in manufacturing of products. I als

learned to analyze the forth-coming problems and to control them.

This project report covers the manufacturing of

1)2-Bromopyridine,

2)4-Acetoxy methyl benzoate,

3)Aspirin.


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INTRODUCTION TO THE COMPANYOmkarSpeciality Chemicals Private Limited on February 24,2005 took over business

Proprietorship Firm M/s. Omkar Chemicals which was in operation since 1983 with Mr. Prav

S. Herlekar as the Proprietor. The Private Limited Company was converted into a Public Limite

Company on March 18, 2010. Company is manly engaged in the manufacture and sale

Speciality Chemicals and Intermediates for Chemical and Allied Industries.

Company has four Units at MIDC, Badlapur(E), Dist: Thane, Maharashtra, India.

The location of our Units are as under:

Unit No. 1W-92(A), MIDC, Badlapur(E), Dist:Thane-421503, State:Maharashtra. Unit No. 2F-24, MIDC, Badlapur(E), Dist: Thane-421503, State: Maharashtra. Unit No.3B-34, MIDC, Badlapur(E), Dist: Thane-421503, State: Maharashtra. Unit No.4F-10/1, MIDC, Badlapur(E), Dist: Thane-421503, State: Maharashtra.

Mr. Herlekar and his dedicated technical team enable company to develop specali

chemical intermediates: Inorganic, Organic &Organo inorganic based on selenium, iodin

molybdenum etc. Over the years, the company could establish goodwill, trust and confidence wi

a majority of domestic and overseas customers belonging to a variety of categories such a

pharmaceuticals/ bulk drugs, cosmetics & healthcare, metal finishing, ceramics & glasswar

poultry & veterinary feeds, reagents for laboratory & research application. The company

turnover has grown many folds during the last two decades and now the company has bee

renamed as M/s. OMKAR SPECIALITY CHEMICALS PVT.LTD from February 2005

encompass its various activities in a big way. Company is primarily involved in the production

Speciality Chemicals and Pharma Intermediates. These company manufactures a range

Organic, Inorganic and Orango Inorganic Intermediates. The Inorganic Intermediates includ


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Molybdenum derivatives, Selenium derivatives, Iodine derivatives, Cobalt derivatives, Bismuth

Tungsten derivatives and the organic intermediates include Tartaric acid derivatives and othe

intermediates. These products find applications in various industries like Pharmaceutica

Industry, Chemical Industry, Glass Industry, Cosmetics, Ceramic Pigments and Cattle & Poult

Feeds.The Company exports products to Europe, Canada, Asia, South America & Australia. Th

Companys association with leading organizations in India and abroad has enabled them

broaden the business, to expand the existing product range and to develop new molecules as pe

the specific demands of our valued customers. The Company has basic research capabilities an

has recently acquired M/S. :RISHICHEM RESEARCH LTD.,[W-83(C), MIDC, Badlapur] as

wholly owned subsidiary which is expected to provide a total R&D back-up to the company fo

all its future expansion and diversification programme.


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INDEX INTRODUCTION STRUCTURE AND PROPERTIES RAW MATERIALS REACTION AND MECHANISM PROCEDURE APPLICATION SPECTRUM DETAILS CALCULATION AND RESULT REFERENCES


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SYNTHESIS OF:2-BROMOPYRIDINEPRODUCT INFORMATION

PRODUCT NAME : 2-Bromopyridine

MOLECULAR WEIGHT : 158gm

STRUCTURAL FORMULA : C5H5BrN

STRUCTURE :

SOLUBILITY : Not available

BOILING POINT : 192-1940C

SPECIFIC GRAVITY : 1.657

PURITY BY GC : 90%

APPEARANCE : Clear liquid , yellow in colour


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Chemical stability and reactivity 2-bromopyridine Chemical stability: stable under normal temperature and pressure. Incompatibilities with other materials: strong oxidizing agents strong

agents-acid chlorides

Packaging and storage: Avoid contact with skin and eyes. Avoidinhalation ofvapours.Keep away from source of ignition-No smoking

Condition for safe storage: Store in cool place .keep container tightly closedin dry and well-ventilated place.

RAW MATERIALS & STIOCHIOMETRYRAW

MATERIAL

QUANTITY MOLECULAR

WEIGHT

NO. OF

MOLES

MOLE

RATIO

2-chloropyridine 300gms 113.5 2.4631 basis

NaBr 435.5gms 103 4.2290 1.6

Acetic acid 127gm 60 2.114 0.8

98%H2SO

4 528.62gms 98 5.2862 2.0

APPARATUS: Round bottom flask Temperature pocket. Dropping funnel. Heating mantle.


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Reaction:

N ClAcetic acid

2-chloropyridine

NaBr,98% H2SO4

N Br

2-bromopyridine


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Mechanism :

Step I]

Na Br

Na Br+ H2SO4 2HBr + Na2SO4

heat

Step II] Nucleophilic substitution.

NCl

+N Br

+ HClheat

2-chloropyridine 2-bromopyridine

H Br


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PROCEDURE FOR SYNTHESIS OF 2-BROMOPYRIDINE 300 gm 2-chloropyridine, 127 gm of acetic acid, and 326.5 gm of NaBr was taken in 3

neck round bottom flask, fitted with a stirrer for the reaction mixture.

Reaction mixture was heated to about at 900C. Another head of RB flask is attached to a dropping funnel. Concentrated H2SO4 and

NaBr was added through the dropping funnel.

The one remaining head of RB flask was fitted with a thermometer pocket The whole arrangement was set on heating mantle, and the temperature was constantly

noted.

As the reaction temperature increased upto 950C addition of H2SO4 was started bydropping funnel.

During the addition of H2SO4 ,reaction temperature was varying from 950C to 1260C. At 1260C heating was stopped and reaction mixture was cooled upto 100C. Heating was started at 1050C addition of remaining quantity of NaBr (109gm)and

H2SO4started by dropping funnel. During the addition temperature of reaction was

varying from 1050c to 120

0C.

At 1240C addition was completed. Reaction mixture was stirred for 2 hour. GC of the sample was constantly analysed. From GC report it was confirmed that all p-chloropyridine was converted into p-

bromopyridine.

Distillation of acetic acid: The reaction maas was taken in 2 neck RB flask and distillation unit was set up.

Unreacted acetic acid was distilled out at 900C


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Vacuum distillation of product: Distillation apparatus was set up. After recovery of acetic acid reaction maas was taken in another distillation.uni

which was attached to a vacuum source .

The whole vacuum distillation unit wass set on heating mantle. When the initial temperature was 500C distillation starts. The whole compound was distilled out at 74-750C/13mm.


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Applications: It is used as an intermediate in the pharmaceutical industry for the manufacture of :-1.Atazanavir (an antiretroviral drug),2. Carbinoxamine,3. Chloropyramine,4. triprolidine5. (antihistamine drugs),6.Disopyramide Phosphate (an antiarrythmic drug),7.Mefloquine8. (antimalarial drug),9. Pipradrol (mild CNS stimulant) etc.


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N Br

7.57

8.61

7.79

7.92

ChemNMR H-1 Estimation

Estimation Quality: blue = good, magenta = medium, red = rough

Protocol of the H-1 NMR Prediction:

Node Shift Base + Inc. Comment (ppm rel. to TMS)

CH 7.57 7.38 2-pyridine, in DMSO

0.19 1 -Br


0.02 1 -BrCH 7.79 7.38 2-pyridine, in DMSO

0.41 1 -Br


0.17 1 -Br

012345678PPM


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CALCULATION: Theoretical yield :

113.54 gm of 2-chloropyridine =158gm of 2-bromopyrridine

300gm of 2-chloropyridine =(158x300)/113.5

=417.62gm

Practical yield =365.5gm

Percentage yield = (practical yield/theriotical yield)x100= (365.5/417.62)x100

= 87.52%


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SYNTHESIS OF: 4-ACETOXY METHYL BENZOATEPRODUCT INFORMATION

PRODUCT NAME : 4-ACETOXY METHYL BENZOATE

MOLUCULAR FORMULA :C10H10O4MOLECULAR WEIGHT : 194.19

STRUCTURAL FORMULA :

PURIFIED BY GC : 80%MELTING POINT : 82-84

0C

APPEREANCE : SOLID


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Reaction:

OH

C

O

O CH3

+ C

O

CH3 C

O

O CH3

pyridine

heat

O C

O

CH3

C

O

O CH3

4-hydroxy methyl benzoate 4-acetoxy methyl bezoateAceticanhydride


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Mechanism:

Step 1:

OH

C

O

OCH3

+N

C

O

OCH3

O-

+NH

+

Heat

4-hydroxy methyl bezoate pyridine

Step2:

O

-

C

O

OCH3

+ C

O

CH3 C

O

O CH3

O C

O

CH3

C

O

OCH3

+

O

CH3 O-

4-hydroxy methyl benzoate

Heat


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PROCEDURE FOR SYNTHESIS OF: 4-ACETOXY METHYLBENZOATE

10 gm of 4-hydroxy methyl benzoate and 11.75 gm of acetic anhydride and 0.3 ml ofpyridine was taken in 3 neck round bottom flask, fitted with the stirrer for the reaction

mixture.

The whole arrangement was set on heating mantale. Reaction mixture was heated about 80 to 900C for 1-2 hrs. The GC of the sample was taken from reaction mixture is constantly analyzed. In GC report it was showing that complete amount of 4-hydroxy methylbenzoate was

converted into 4-acetoxy methylbenzoate

Reaction mixture allowed to cool. Reaction mixture was poured into ice water andprecipitate of 4-actoxy methyl benzoate was separated off and dried.

Purified by ethyl acetate and M.P was taken.


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O O

O

O

7.90 7.30

7.307.90

5.34 2.01

3.88

ChemNMR H-1 Estimation

Estimation Quality: blue = good, magenta = medium, red = rough

Protocol of the H-1 NMR Prediction:

Node Shift Base + Inc. Comment (ppm rel. to TMS)

CH 7.90 7.26 1-benzene

0.71 1 -C(=O)OC

-0.07 1 -C-O


0.11 1 -C(=O)OC

-0.07 1 -C-O


0.11 1 -C(=O)OC

-0.07 1 -C-OCH 7.90 7.26 1-benzene

0.71 1 -C(=O)OC

-0.07 1 -C-O

CH2 5.34 1.37 methylene

1.22 1 alpha -1:C*C*C*C*C*C*1

2.75 1 alpha -OC(=O)-C

CH3 2.01 0.86 methyl1.15 1 alpha -C(=O)OC

CH3 3.88 0.86 methyl

3.02 1 alpha -OC(=O)-1:C*C*C*C*C*C*1

012345678PPM


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CALCULATION: THEORETICAL YIELD:

166.17gm of4-hydroxy methyl benzoate =194.19gm of 4-acetoxy methyl benzoate

10gm of 4-hydroxy methyl benzoate = (10x194.19)/166.17

=11.68 gm

Practical yield =9.05gm Percentage yield = (practical yield/theoretical yield)x100

=9.05/11.68)x100

= 77.48%


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RESULT:

Theoretical Yield 11.68gm

Practical Yield 9.05gm

Percentage Yield 77.48%


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SYNTHESIS OF: ASPIRIN

PRODUCT INFORMATIONPRODUCT NAME : ASPIRIN

MOLECULAR WEIGHT : 180.15gm/mol

MOLUCULAR FPRMULA : C9H8O4

STRUCTURAL FORMULA :

APPEARANCE : SOLID

COLOUR : WHITE

MELTING POINT : 1350C
http://www.frca.co.uk/article.aspx?articleid=100633


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RAW MATERIALS& STIOCHIOMETRY

RAW

MATERIAL

QUANTITY MOLECULAR

WEIGHT

NO. OF

MOLES

MOLE

RATIO

Salicylic acid 200gm 138 1.45 1

Acetic anhydride 235gm 102 2.20 1.52

pyridine 6ml

APPARATUS: Round bottom flask Temperature pocket. Dropping funnel. Heating mantle.


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Reaction:

C

O

OH

OH

+ C

O

CH3 C

O

O CH3

C

O

OH

OCOCH 3pyridine

reflux

salicylic acid AceticanhydrideAspirin


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Mechanism: acetylation of salicylic acid

Step I]

COOH

OH

+

NN

+

COOH

H

O

+

Step II]

N

H

+

COOH

O

+ H3C-C-O-C-CH3

O O

COOH

OCOCH3

+

O

OH3C


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PROCEDURE FOR SYNTHESIS OF:ASPIRIN 200gm of salicylic acid ,238gm of acetic unhydride and 6ml of pyridine was taken in 3

neck round bottom flask, fitted with stirrer for the reaction system.

The whole arrangement was set on heating mantle Reaction mixture was heated at 80-900C temperature for 2-3 hrs The GC of the sample was taken from reaction mixture was constantly analyzed In GC report it was showed that the whole amount of salicylic acid was converted into

aspirin

Reaction mixture allowed to cool. Reaction mixture was poured into ice water andprecipitate of aspirine was separated off and dried.

Purified by ethyl acetate and M.P was taken


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APPLICATION OF:ASPIRIN Acetylsalicylic Acid is used in analgesics, anti-inflammatories, antipyretics

anticoagulants and anti-rheumatics. It is also used as an additive in food, animal feed,

drug and cosmetic.

Nonsteroidal Antiinflammatory Drugs (NSAIDs); chemically heterogeneous large groupsof drugs which suppress inflammation in a manner similar to steroids, but less side

effects of sedation, respiratory depression, or addiction than steroids. They are widely

used for the treatment of inflammatory disorders and painful conditions such as

rheumatoid arthritis, gout, bursitis, painful menstruation, and headache. They are

effective in the relief of pain and fever.


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CALCULATION: Theoretical yield

138.12gm of salicylic acid =180.15 gm of Aspirin

200gm of salicylic acid = (180.5x200)/138.12

=260.86gm

Practical yield =219.13gm

Percentage yield = (practical yield/theoretical yield)x100= (219.13/260.86)x100

= 84%


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RESULT:

Theoretical Yield 260.86gm

Practical Yield 219.13gm

Percentage Yield 84%


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CONCLUSION

It has been a pleasure experience to work in one of the most illustrious companies

existing in India. At the end of my training tenure, I wish to epitomize the benefits occurred over

period of 21 days. The training has certainly helped me in bridging the gap between theory and

practical. It provides me with an opportunity to learn under a different environment. I gained

quite a lot of things from this training and they are listed below:

This training offered and exposure to industrial environment, which cannot be simulated ithe collages.

I understood the scope and job responsibilities of the various departments of anengineering organization.

It enables me to get familiarized with various materials, processes, products and theirapplication.

I gained insight into the psychology of the workers and their habits and attitudes. I was able to appreciate the need for coordinated efforts of various persons at different

departments in achieving set goals and targets.

I was introduced to the latest equipments for machining and inspection.


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REFERENCES Name Reactions: A Collection of Detailed Reaction Mechanisms By Jie Jack Li

Published2003

Organic Chemistry By Clayden,Greeves, Warren And Wothers Revised Addition Reaction Mechanism And Rearrangment By S.N. Sanyal Revised Addition- 2010 Organic Chemistry ByMorrison And Boyd 2009 addition. March, Jerry(2007), Advanced organic chemistry:Reactions, mechanisms,and structure

(6th ed.)


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SAFETY DAT A SHEET:Before working in any industries with hazards chemical we must have following information of

chemicals &we must use precautionaryMeasures according for e.g. using gloves, using safety

goggles, using mask etc.

Identification of the substance of the company. Composition of ingredients. Hazards identification. Fire fighting measures. Handling and storage. Exposures control / personal protection. Physical and chemical properties. Stability and reactivity. Toxicological information. Disposal consideration. Transport information. Other information.


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final project of msc ii

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