SYNTHESIS AND CHARACTERIZATION OF

PHENLY BENZOATE AND O-NITROPHENOL

FROM PHENOL BY ACITYLATION REACTION

A project report submitted to

Mumbai University.
As a partial fulfilment for the award of degree of
MASTER OF SCIENCE
(Organic Chemistry)

By

Sahil Suhas Sawant

Under the Guidance of

Mr. S. P. Patil
D.B.J. College, Chiplun

DEPARTMENT OF CHEMISTRY
D.B.J. COLLEGE, CHIPLUN
2022-2023.
 DBJ COLLEGE CHIPLUN
DEPARTMENT OF CHEMISTRY
(Post-Graduate section)

CERTIFICATE

This is to certified that Mr. Sahil Suhas Sawant of the

MSc (part-II) Organic Chemistry Class has satisfactorily
completed the Research project experimental Study of
“SYNTHESIS AND CHARACTERIZATION OF PHENLY
BENZOATE AND O-NITROPHENOL FROM PHENOL BY
ACITYLATION REACTION”As prescribed by the
University of Mumbai, under my guidance, during the
academic year 2022-23.

Teacher Incharge Head

Date:- Department Of Chemistry
2
 ACKNOWLEDGEMENT

I have a great pleasure to thank Prof. Mr. S. P. Patil Sir for

their initiation, encouragement & valuable guidance to
complete this project work.
I am also thankful to the laboratory staff for providing
me apparatus & chemicals.
I also sincerely thank to my parents, friends, teachers,
supporting staff of department & the Principal.

3
 Declaration
I undersigned hereby declare that the Research project work entitled
SYNTHESIS AND CHARACTERIZATION OF PHENLY
BENZOATE AND O-NITROPHENOL FROM PHENOL
BY ACITYLATION REACTION is done under the guidance
of Mr. S. P. Patil Sir in organic chemistry at D B.J. college,
Chiplun & this is my original work.

The empirical results in this project report are based on my own

experiments which I had done at college laboratory. I will not
publish this in full or in parts in any format without prior permission
from the institute

Date:- Sahil Suhas Sawant

Place:- Chiplun ( MSc- II)

D.B.J. College Chiplun

4
 INDEX

Sr. No. CONTENT Page No.

01] 6
Abstract

02] 7
Objective of the work

03] 8
Introduction and literature survey

04] 9-21
MSDS

05] 22 - 34
Experimental work

06] 35
Results

07] 36
Conclusion

08] 37-38
Recommended References

5
SYNTHESIS AND CHARACTERIZATION OF PHENLY
BENZOATE AND O-NITROPHENOL FROM PHENOL
BY ACITYLATION REACTION

ABSTRACT

Acetylation is a reaction that introduces an acetyl

functional group into an organic chemical functional
group into an organic chemical compound namely the
substiutiuon of acetyl group for a hydrogen atom while
decetylation is the removal of an acyl group from an
oganic chemical compound.
In chemistry acetylation is an organic esterification
reaction with acetic acid subcompounds are turned as
acetate ester or simply acetates.
More specifically, the existing invention focus in
the synthesis of phenyl benzoate and O-nitrophenol
from phenol by acetylation reaction

6
 OBJECTIVE OF THE WORK

 To use the acetylation reaction for the synthesis of phenyl

benzoate and O-nitrophenol from phenol
 Learn the principle of Schottman-Bauman reaction
 Master the operation of recrystalisation

7
INTRODUCTION AND LITERATURE SURVEY

Synthesis of phenyl benzoate from phenol is an example of

Schotten. Baumann Reaction where phenols react with an aromatic acid
chloride in the presence of an excess of a base at room temperature to
form an ester. In this reaction, phenol is shaken with benzoyl chloride
and excess amount of sodium hydroxide solution, it is benzoylated to
give the ester, phenyl benzoate. The phenol is first converted into the
ionic compound sodium hydroxide to give sodium phenoxide (sodium
phenate) by dissolving in sodium hydroxide solution. The phenoxide
ions reacts more rapidly with benzoyl chloride than the original phenol
does, but even so you have to shake it with benzoyl chloride for about
15 minutes. Solid phenyl benzoate is formed.to give phenyl benzoate.
When phenol is treated with allyl bromide in the presence of
potassium carbonate and acetone, the product is almost entirely allyl
phenyl ether. This undergoes ready thermal rearrangement to give 2-
allylphenol, which is an example of the Claisen rearrangement. A
protropic shift may be induced to effect double bond migration in the
side chain by heating the allyl phenyl ether with methanolic potassium
hydroxide when 2-(prop-1-enyl) phenol is formed.
 MATERIAL SAFETY DATA SHEET
Phenol
1. HAZARDS IDENTIFICATION
Emergency Overview
Highly toxic
Corrosive
Combustible
Appearance Clear, Two-Layer Physical State Liquid Odor Phenolic, Medicinal

Potential Health
Effects Acute Toxicity
Eyes Corrosive.
Skin Very toxic in contact with skin. Corrosive, causes burns. readily absorbed
through skin.
Inhalation Very toxic by inhalation. corrosive ,causes burns.
Ingestion Very toxic if swallowed. Corrosive, causes burns.

Chronic Effects No known effect based on information supplied.

Aggravated Medical Conditions None known.

Environmental Hazard See Section 12 for additional Ecological Information.

2. COMPOSITION/INFORMATION ON INGREDIENTS

Chemical Name CAS-No Weight %

Phenol 108-95-2 95-100

3. FIRST AID MEASURES

Eye Contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a
physician.
Skin Contact Wash skin with soap and water.

Inhalation Move to fresh air. If breathing becomes difficult, give oxygen.

Ingestion Clean mouth with water and afterwards drink plenty of water.

Notes to Physician Treat symptomatically.

4. FIRE-FIGHTING MEASURES

Flammable Properties combustible liquid.

Flash Point Not determined

Suitable Extinguishing Media Dry chemical, CO2, water spray or regular foam.

Hazardous Combustion Products Carbon oxides

Explosion Data
Sensitivity to Mechanical Impact Not sensitive.
Sensitivity to Static Discharge Not sensitive.

Protective Equipment and Precautions for Firefighters As in any fire, wear self-contained breathing apparatus pressure-
demand, MSHA/NIOSH (approved or
equivalent) and full protective gear.

NFPA Health Hazard - Flammability - Stability- Physical and Chemical

Hazards -

5. ACCIDENTAL RELEASE MEASURES

Personal Precautions Avoid contact with skin, eyes and clothing. Use personal protective
equipment. Ensure
adequate ventilation
.

Methods for Containment Prevent further leakage or spillage if safe to do so.

Methods for Cleaning Up Cover with dry lime or soda ash. Pick up and transfer to properly labeled containers.
Ventilate area and wash spill site after material pickup is complete.

6. HANDLING AND STORAGE

Handling Handle in accordance with good industrial hygiene and safety practice. Light
Sensitive.

Storage Keep containers tightly closed in a dry, cool and well-ventilated place.
Protect from light.

7. EXPOSURE CONTROLS / PERSONAL PROTECTION

Chemical Name ACGIH TLV OSHA PEL NIOSH IDLH
Phenol TWA: 5 ppm TWA: 19 mg/m3 IDLH: 250 ppm
108-95-2 TWA: 5 ppm Ceiling: 15.6 ppm
(vacated) TWA: 19 mg/m3 Ceiling: 60 mg/m3
(vacated) TWA: 5 ppm TWA: 19 mg/m3
Skin TWA: 5 ppm
 8. PHYSICAL AND CHEMICAL PROPERTIES
Appearance Clear Two-Layer Odor Phenolic, Medicinal
Physical State Liquid
Flash No information Autoignition Temperature No information available
Point available
Boiling Point/Range No information available
Flammability Limits in Air No information available
Explosion Limits No information available

Solubility No information available Evaporation Rate No information available

Vapor Density No information available.

9. STABILITY AND REACTIVITY

Stability Stable under recommended storage conditions.

Incompatible Products Strong oxidizing agents. Strong acids. Strong bases.

Conditions to Avoid Protect from light.

Hazardous Decomposition Products Carbon oxides.

Hazardous Polymerization Hazardous polymerization does not occur.

10. TOXICOLOGICAL INFORMATION

Acute Toxicity

Product Information Very toxic by inhalation, in contact with skin, or if swallowed. Corrosive,
causes burns.

Chemical Name LD50 Oral LD50 Dermal LC50 Inhalation

Phenol 317 mg/kg ( Rat ) 525 mg/kg ( Rat ) 316 mg/m3( Rat ) 4 h
630 mg/kg ( Rabbit )

Chronic Toxicity

Target Organ Effects Kidney, Liver, Central nervous system (CNS)

11. ECOLOGICAL INFORMATION

Ecotoxicity
Harmful to aquatic organisms.
Chemical Name Toxicity to Algae Toxicity to Fish Microtox Daphnia Magna (Water
Flea)
Phenol EC50 = 150 mg/L 96 h LC50 5 - 12 mg/L EC50 21 - 36 mg/L 30 min LC50 = 13 mg/L 48 h
Oncorhynchus mykiss 96 h EC50 = 23.28 mg/L 5 min EC50 = 23.0 mg/L 48 h
LC50= 23.88 mg/L Lepomis EC50 = 25.61 mg/L 15 min
macrochirus 96 h EC50 = 28.8 mg/L 5 min
LC50= 24 mg/L Pimephales EC50 = 31.6 mg/L 15 min
promelas 96 h
LC50= 27.8 mg/L
Brachydanio rerio 96 h
LC50= 40 mg/L Poecilia
reticulata 96 h
LC50= 8.9 mg/L
Oncorhynchus mykiss 96 h

Chemical Name Log Pow

Phenol = 1.47

12. DISPOSAL CONSIDERATIONS

Waste Disposal Method Dispose of material in accordance with all federal, state, and local regulations.

Contaminated Packaging Dispose of in accordance with all federal, state and local regulations.

Chemical Name
Phenol - 108-95-2

Chemical Name RCRA - Halogenated RCRA - P Series RCRA - F Series RCRA - K Series RCRA - U Series
Organic Compounds Wastes Wastes Wastes Wastes
Phenol - 108-95-2 U188

Chemical Name California Hazardous Waste Status

Phenol Toxic; Corrosive
 13. REGULATORY INFORMATION

International Inventories
U.S. Federal Regulations
Clean Water Act
This product contains the following substances which are regulated pollutants pursuant to the Clean
Water Act (40 CFR 122.21 and 40 CFR 122.42).
Component CWA - Reportable CWA - Toxic Pollutants CWA - Priority Pollutants CWA - Hazardous
Quantities Substances
Phenol 1000 lb X X X
108-95-2 ( 95-100 )

This product contains the following substances which are listed hazardous air pollutants (HAPS) under
Section 112 of the Clean Air Act:.
Chemical Name CAS-No Weight % HAPS data VOC Chemicals Class 1 Ozone Class 2 Ozone
Depletors Depletors
Phenol 108-95-2 95-100 Present Group III

CERCLA

Chemical Name Hazardous Substances RQs Extremely Hazardous Substances RQs

Phenol 1000 lb 1000 lb

U.S. State Regulations

Chemical Name Massachusetts New Jersey Pennsylvania Illinois Rhode Island
Phenol X X X X X
 Chemical Name Carcinogen Status Exposure Limits
Phenol Mexico: TWA= 19 mg/m3
Mexico: TWA= 5 ppm
Mexico: STEL= 38 mg/m3
Mexico: STEL= 10 ppm

16. OTHER INFORMATION

Issuing Date 06/04/10

Revision Date
Revision Note No information available.

Disclaimer
The information provided on this MSDS is correct to the best of our knowledge, information and belief at the date of
its publication. The information given is designed only as a guide for safe handling, use, processing, storage,
transportation, disposal and release and is not to be considered as a warranty or quality specification. The
information relates only to the specific material designated and may not be valid for such material used in
combination with any othermaterial or in any process, unless specified in the text.
 MATERIAL SAFETY DATA SHEET

Phenyl Benzoate
1. PRODUCT AND COMPANY IDENTIFICATION

Product name : Phenyl benzoate

Product Number : 142719
Brand : Aldrich

Company : Sigma-
Aldrich 3050
Spruce
Street
SAINT LOUIS MO
63103USA
Telephone : +1 800-325-5832
Fax : +1 800-325-5052
Emergency Phone # : (314) 776-6555

2. COMPOSITION/INFORMATION ON INGREDIENTS

Synonyms : Benzoic acid phenyl ester

Formula : C13H10O2
Molecular Weight : 198.22 g/mol
3. HAZARDS IDENTIFICATION

Emergency
Overview
OSHA
Hazards
Harmful by ingestion., Irritant
HMIS Classification
Health Hazard: 2
Flammability: 0
Physical hazards: 0
NFPA Rating
Health Hazard: 2
Fire: 0
Reactivity Hazard: 0
Potential Health Effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes eye irritation.
Ingestion Harmful if swallowed.
5

4. FIRST AID MEASURES

General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.Move out of dangerous area.
If inhaled
If breathed in, move person into fresh air. If not breathing give artificial respiration Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

5. FIRE-FIGHTING MEASURES

Flammable properties
Flash point no data available
Ignition temperature no data available
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
 6. ACCIDENTAL RELEASE MEASURES

Personal precautions
Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.
Environmental precautions
Do not let product enter drains.
Methods for cleaning up
Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.

7. HANDLING AND STORAGE

Handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fireprotection.
Storage
Keep container tightly closed in a dry and well-ventilated place.

8. EXPOSURE CONTROLS/PERSONAL PROTECTION

Contains no substances with occupational exposure limit values.

Personal protective
equipmentRespiratory
protection
Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1
(EN 143) respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
5
 Hand protection
Handle with gloves.
Eye protection
Safety glasses with side-shields conforming to EN166
Skin and body protection
Choose body protection according to the amount and concentration of the dangerous substance at the
work place.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.

9. PHYSICAL AND CHEMICAL PROPERTIES

Appearance
Form crystalline
Colour white
Safety data
pH no data available
Melting point 68 - 70 °C (154 - 158 °F) - lit.
Boiling point 298 - 299 °C (568 - 570 °F) - lit.

Flash point no data

available Ignition temperature no
data available Lower explosion limit
no data available Upper explosion
limit no data available Water
solubility no data
available

10. STABILITY AND REACTIVITY

Storage stability
Stable under recommended storage conditions.
Materials to avoid
Strong oxidizing agents, Strong acids, Strong bases
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides

11. TOXICOLOGICAL INFORMATION

Acute toxicity
LD50 Oral - mouse - 1,225 mg/kg
Irritation and
corrosion no data
IARC: No component of this product present at levels greater than or equal to 0.1% is
identified as probable, possible or confirmed human carcinogen by IARC.
ACGIH: No component of this product present at levels greater than or equal to 0.1% is
identified as a carcinogen or potential carcinogen by ACGIH.
NTP: No component of this product present at levels greater than or equal to 0.1% is
identified as a known or anticipated carcinogen by NTP.
OSHA: No component of this product present at levels greater than or equal to 0.1% is
identified as a carcinogen or potential carcinogen by OSHA.

Signs and Symptoms of Exposure

To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Potential Health Effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes eye irritation.
Ingestion Harmful if swallowed.
Additional Information
RTECS: DH6299500

12. ECOLOGICAL INFORMATION

Elimination information (persistence and degradability)

no data available

Ecotoxicity effects
no data available
Further information on ecology
no data available

13. DISPOSAL CONSIDERATIONS

Product
Observe all federal, state, and local environmental regulations. Contact a licensed professional
waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

14. TRANSPORT INFORMATION

DOT (US)
Not dangerous goods

IMDG
Not dangerous goods

IATA
Not dangerous goods
OSHA Hazards
Harmful by ingestion., Irritant
DSL Status
This product contains the following components listed on the Canadian NDSL list. All other components
are on theCanadian DSL list.
CAS-
Phenyl benzoate No. 93-
SARA 302 Components 99-2
SARA 302: No chemicals in this material are subject to the reporting requirements of SARA Title III, Section 302.
SARA 313 Components
SARA 313: This material does not contain any chemical components with known CAS numbers that
exceed the threshold (De Minimis) reporting levels established by SARA Title III, Section 313.
SARA 311/312 Hazards
Acute Health Hazard
Massachusetts Right To Know Components
No components are subject to the Massachusetts Right to Know Act.
Pennsylvania Right To Know Components
CAS- Revision Date
Phenyl benzoate No. 93-
99-2
New Jersey Right To Know Components
Revision Date
CAS-
Phenyl benzoate
No. 93-
California Prop. 65 Components
99-2
This product does not contain any chemicals known to State of California to cause cancer,
birth, or any otherreproductive defects.

15. OTHER INFORMATION

Further information
Copyright 2009 Sigma-Aldrich Co. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and
shall be used only as a guide. The information in this document is based on the present state
of our knowledge and is applicable to the product with regard to appropriate safety
precautions. It does not represent any guarantee of the properties of the product. Sigma-
Aldrich Co., shall not be held liable for any damage resulting from handling or from contact
with the above product. See reverse side of invoice or packing slip for additional terms and
conditions of sale.
 EXPERIMENTAL WORK :

Reaction No.01
PURPOSE : Preparation of phenyl benzoate from phenyl

Material and method

●Chemicals: The Chemical used for these reactions are-

(1) Phenol
(2) Benzochloride
(3) Ethanol
(4) 10% Sodium Hydroxide
(5) Methanol

●Glassware:
(1) Conical flask
(2) pipette
(3) Volumetric flask
(4) Glass stirring rod
(5) separating funnel
(6) Suction pump
(7) Measuring cylinder
(8) Filter paper
(9) Rubber cork
(10) Spatula
(11) Fume hood
REACTION
General procedure for Phenyl Benzoate

1]. Take a 1.0 g of phenol and add a 15 mL of 10% sodium

hydroxide solution in 250 ml Erlenmeyer flask with a good rubber
cork and shake well at room temperature.
2]. In another conical flask take a mixture of a 0.93 ml of aniline
and 1.22 gm of benzaldehyde in another conical flask these is
the without extract solution.
3]. The reaction should be complete, and a solid product
obtained is filter off with suction pump on Buchner funnel,
breaking up any lumps occurs in a crude product on the filter
with a spatula, and then wash thoroughly with ice water.
4 Erlenmeyer flask rinse with cold water in 2 times to remove any
residual crystals which may be present in a crude product.
5].Phenyl benzoate as possible from the Buchner funnel to a
clean, dry 250 mL beaker and recrystallize it from methanol.
6].Weigh the recrystallized phenyl benzoate and calculate the
practical yield about 1.8 gm.
7]. Determine the melting point of the synthesized phenyl
benzoate.
8]. It’s obtained as colorless needles; melting point is 68–69oC.
REACTION
Mechanism
 TLC
(PRINCIPAL OF TLC)
A compound or combination is utilized to a beginning factor
simply above the bottom of TLC plate. The plate is then developed
in the growing chamber that has a shallow pool of solvent simply
under the degree at which the pattern used to be applied. The
solvent is. drawn up thru the particles on the plate via the capillary
action, and as the solvent moves over the combination every
compound will both continue to be with the stable section or
dissolve Thin layer chromatography makes use of a skinny glass
plate covered with both aluminium oxide or silica gel as the stable
phase. The cellular segment is a solvent chosen according to the
houses of the aspects in the mixture. The precept of TLC is the
distribution of a compound between a stable constant segment (the
skinny layer) utilized to a glass or plastic plate and a liquid cellular
section (eluting solvent) that is shifting over the strong phase. A
small quantity of in the solvent and cross up the plate. Whether the
compound strikes up the plate or stays behind rely on the bodily
homes of that person compound and for that reason rely on its
molecular structure, especially useful groups. The solubility rule
"Like Dissolves Like “is followed. The extra comparable the bodily
homes of the compound to the cell phase, the longer it will continue
to be in the cellular phase. The cell section will elevate the most
soluble compounds the furthest up the TLC plate. The compounds
that are much less soluble in the cell phase and have a greater
affinity to the particles on the TLC plate.
 STOICHIOMETRIC CALCULATION
Phenol Benzyl NaOH
1.07g/cm3 1.21 gm/Cm3
Molecular formula C6H6O C6H7N NaOH
Molecular weight 94.4 140.57 39.97

Molar Ratio 1 1 1
Quantity in gram 1 1.49 0.42
Volume in Cm3 0.93 1.23 0.19

Number of Moles 0.0106 0.0106 0.0106

As molar ratio of reaction is 1:1 hence no of moles of Aniline 0.0099 Moles.

(1) Number of Moles of Phenol =

= Weight in gm/ Molecular weight
=1/94.4
= 0.0106

(2) No. of moles of phenol = No. of moles of Benzoyl chloride== No. of moles of
NaOH
= 0.0106
Since molar ration is 1:1:1

(3) Volume of Phenol=

= Mass of phenol/ Density
= 1/1.07
= 0.93 Cm3

(4) Quantity in gm of benzoyl chloride=

= No. of moles x molecular weight
= 1.0106/140.52
= 1.4 g

(5) Volume of benzoyl chloride =

= Mass in gm/ density
=1.49/1.21
=1.23
 (6) Qunatity of gm of NaOH=
= No. of moles x molecular
=0.0106 x 39.92
=0.42

(7) Volume of NaOH=

= Mass of NaOH/ Density
=0.42/2.13
=0.19

TLC

Solvent system 70% Heptane +30%

Ethyl acetate
RF value 0.8

RF value = Distance travelled by solute/ Distance travelled by solvent

= 4.6/5.2
= 0.8
 CALCULATION

1].THEORETICAL YIELD
94 gm of Phenol= 198 gms of phenyl benzoate
1 g of phenol will form
= 1 x 198/ 94
= 2.106 gm

2].PERCENTAGE YIELD

Observed yield/ Theortical yield x100

=0.504/2.106 x 100
=26.78 %
 Observations

 Weight of supplied sample = 1g of phenol

 Weight of crude product = 0.780 g
 Weight of purified product = 0.564 g
 Melting point = 69°C
 EXPERIMENTAL WORK :

Reaction No.02
PURPOSE : Preparation of O-nirophenol from phenol

Material and method

●Chemicals: The Chemical used for these reactions are-

(1) Sulphuric acid
(2) Sodium Nitrate
(3) Phenol

●Glassware:
(1) Conical flask
(2) pipette
(3) Volumetric flask
(4) Glass stirring rod
(5) separating funnel
(6) Suction pump
(7) Measuring cylinder
(8) Filter paper
(9) Rubber cork
(10) Spatula
(11) Fume hood
REACTION
General procedure for O-Nitrophenol

1]. Cautiously add 250 g of concentrated sulphuric acid in thin

stream and with stirring to 400 ml of water contained in a 1 litre
three necked flask.
2]. Dissolve 150 g of sodium nitrate in the diluted acid .
3]. Cool in a bath of ice or ice water. Melt 94 g of phenol with 20
ml of water.
4 Add this dropwise from sepretary funnel to the vigorously
stirred mixture in a flask.
5].Maintain the temperature at about 20°C. Continue stirring for
further 2 hours after all the phenol has been added. Pour of the
mother-Liquor from the resinous mixture of nitro compounds.
6].Melt the residue with 500 ml of water. Shake and allow the
content of the flask to settle.
7].Pour of the washed liquor and repeat atleast 2-3 times to
ensure the complete the removal of any residual acid.
8]. Steam distil the mixture until no more nitrophenol pass over if
the later tends to solidify the condenser.
 Reaction

Mechanism
 TLC
(PRINCIPAL OF TLC)
A compound or combination is utilized to a beginning factor
simply above the bottom of TLC plate. The plate is then developed
in the growing chamber that has a shallow pool of solvent simply
under the degree at which the pattern used to be applied. The
solvent is. drawn up thru the particles on the plate via the capillary
action, and as the solvent moves over the combination every
compound will both continue to be with the stable section or
dissolve Thin layer chromatography makes use of a skinny glass
plate covered with both aluminium oxide or silica gel as the stable
phase. The cellular segment is a solvent chosen according to the
houses of the aspects in the mixture. The precept of TLC is the
distribution of a compound between a stable constant segment (the
skinny layer) utilized to a glass or plastic plate and a liquid cellular
section (eluting solvent) that is shifting over the strong phase. A
small quantity of in the solvent and cross up the plate. Whether the
compound strikes up the plate or stays behind rely on the bodily
homes of that person compound and for that reason rely on its
molecular structure, especially useful groups. The solubility rule
"Like Dissolves Like “is followed. The extra comparable the bodily
homes of the compound to the cell phase, the longer it will continue
to be in the cellular phase. The cell section will elevate the most
soluble compounds the furthest up the TLC plate. The compounds
that are much less soluble in the cell phase and have a greater
affinity to the particles on the TLC plate.
 STOICHIOMETRIC CALCULATION
Phenol HNO3
1.07g/cm3 1.5 g/cm3
Molecular formula C6H6O HNO3
Molecular weight 94.4 63.01
Molar Ratio 1 1
Quantity in gram 1 0.66
Volume in Cm3 0.93 0.43

Number of Moles 0.0106 0.0106

As molar ratio of reaction is 1:1 hence no of moles of Aniline 0.0099 Moles.

(1) Number of Moles of Phenol =

= Weight in gm/ Molecular weight
=1/94.4
= 0.0106

(2) No. of moles of phenol = No, of moles of HNO3

= 0.0106
Since molar ration is 1:1:1

(3) Volume of Phenol=

= Mass of phenol/ Density
= 1/1.07
= 0.93 Cm3

(4) Quantity in gm of HNO3=

= No. of moles x molecular weight
= 1.0106/63.01
= 0.66 g

(5) Volume of HNO3=

= Mass in gm/ density
=0.66/1.51
=0.43
CALCULATION

1].THEORETICAL YIELD
94 gm of Phenol= 139 gms of O-Nitrophenol
1 g of phenol will form
= 1 x 139/ 94
= 1.478 gm

2].PERCENTAGE YIELD

Observed yield/ Theortical yield x100

=0.548/1.478 x 100
=37.07 %
TLC

Solvent system 80% Heptane +20%

Ethyl acetate
RF value 0.6

RF value = Distance travelled by solute/ Distance travelled by solvent

= 3.2/4.8
= 0.6
 Observations

 Weight of supplied sample = 1g of phenol

 Weight of crude product = 0.656 g
 Weight of purified product = 0.548 g
 Melting point = 46°C
 Result

Reaction-01

Theoretical Practical Yield % Yield M.P

Yeild Crude Purified
2.106 0.786 0.564 26.78% 69°C
Reaction-02

Theoretical Practical Yield % Yield M.P

Yeild Crude Purified
1.478 0.656 0.548 37.07% 46°C
 Conclusion

The acetylation reaction is the most effective route for the

synthesis and characterization of the phenyl benzoate and O-
nitrophenol from phenol. The experiment was success in phenyl
benzoate and O-nitrophenol synthesis and was purified properly.
The solvent suitable for recrystallization of the desirable product
found in acetylation recation and Schottman-Bauman reaction
was performed in organic laboratory by the huge synthesis.This
study also clears the concept of Acetylation and Schottman-
Bauman reaction.
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