Presentation of Benzoic Acid From Benzamide

SYNTHESIS OF BENZOIC ACID FROM
BENZAMIDE
NAME : FAZAL RAHIM SHAH

DEPARTMENT : CHEMISTRY
SEAT NO : EH2009019
CONTENTS
.
INTRODUCTIO
N
APPLICATION
PLAN OF
WORK
CONCLUSION
FUTURE PLAN
MOST
PUBLICATION
INTRODUCTION
What is Benzoic acid ?
Benzoic acid C7H602 is a colorless crystalline solid and a simple aromatic carboxylic acid
The name is derived from gum benzoin , which was for a long time its only known source .
Benzoic acid occurs naturally in many plants and it serves as an
intermediate in the biosynthesis many secondary metabolites
IMPORTANTANCE :
Benzoic acid is most commonly found in industrial setting to
Manufacture a wide variety of product such as perfumes
, dyes, topical medications , and insect repellents .
Benzoic acid salt ( sodium benzoate is commonly used as a
Ph adjustor and preservation in food preventing the
Growth of microbes to keep food safe .
CHEMISTRY OF BENZOIC ACIDBenzoic C7H6O2 or
Acid C6H5COOH
 The structure of a C6H5COOH molecule is illustrated below. Formula
This molecule consists of a benzene ring to which Molecular
122.12
a carboxyl functional group is linked. The molecule consists of 7 Weight/
g/mol
Molar Mass
carbon atoms, 6 hydrogen atoms, and 2 oxygen atoms.
 It is soluble in water, and the solubility at 25oC and 100oC 1.27
Density g/cm3 at
is 3.44 g/L and 56.31 g/L respectively. 15oC
 It is soluble in benzene, carbon tetrachloride, acetone, and
Boiling
alcohols. 523K
Point
 The acid dissociation constant (pKa) Melting
395 K
of benzoic acid corresponds to 4.2 Point
 Its reactions can occur at the carboxyl group or even at the aromatic ring.
METHOD OF SYNTHESIS
THERE ARE SEVERAL METHODS TO SYNTHESIZE BENZOIC ACID SOME METHODS ARE
REACTIONS ( ORTHO , PARA POSITION )
 Electron-donating substituents increase the electron density of the aromatic ring,
activating it, and increasing the rate of electrophilic substitutions.
 Electron-withdrawing groups decreased electron density, deactivating the aromatic ring,
and reduced the rate of electrophilic substitution. In a similar fashion, substituents have
an effect on the acidity of benzoic acids.
 Deactivating substituents, such a nitro group (-NO2), in the ortho or meta position
remove electron density from the aromatic ring, and also from the carboxylate anion.
This stabilizes the negative charge of the conjugate base,
increasing the acidity of the carboxylic acid.
 The opposite effect occurs with electron donating substituents.
The conjugate base of benzoic acid is destabilized by electron-donating
substituents in the meta or ortho position making the carboxylic acid less acidic.
such as an amino substituent which still causes the benzoic acid to be less acidic.
ORTHO EFFECT
 Almost all ortho-substituents increase the acid strength of a benzoic acid
regardless of whether they are electron-donating or electron-withdrawing.
This is called the ortho-effect and its cause is not completely understood.
It is theorized to be a combination of both steric and electronic factors.
There are exceptions of the ortho-effect,
EXAMPLE :
The following molecule, p-cyanobenzoic acid, has a pKa of 3.55.
Does the cyano substituent activate or deactivate the aromatic ring
towards electrophilic aromatic substitution?
The pKa of benzoic acid is 4.2 which means it is a weaker acid than
p-cyanobenzoic acid. This this means that the cyano substituent is
deactivating the ring.
APPLICATIONS
Biological :
 This compound is used in ointments that prevent or treat fungal skin diseases.
 Benzoic acid inhibits the growth of mold, yeast and some bacteria.
 The undissociated form on benzoic acid is the most effective antimicrobial agent.
 pK of 4.2; optimum pH range is from 2.5 to 4.0.
Chemicals :
 It is also a precursor to benzoyl chloride.
 The primary use of benzoic acid is in the industrial production
of the aromatic compound phenol, this process known as oxidative decarboxylation
 Benzoic acid occurs naturally in many types of plums, prunes and some spices.
 It is used as benzoic acid or as benzoate
TEXTILE :
 Benzoic acid is used across a range of applications in various end-use industries
due to easy availability of pure quality alkyd resins and their low development costs
 It is also used as a rubber polymerization activator and retardant
PLAN OF WORK
PRINCIPLE :benzamide C6H5CONH2 may be hydrolyzed by aqueous acid alkali ,

yielding benzoic acid.
PLAN OF WORK
MECHANISM :
PLAN OF WORK
PROCEDURE :
 Weight out 1g of benzamide place it in a conical flask and
added10% NaOH 12ml , 10 ml of water also added in conical
flask .
 Fit the flask with cork carrying a glass rubbing and boil the mixture
for about 20- 30 minutes Test the gas evolved at the head
of the glass tubing when the mixture is begin to boil .
 Allow the mixture to cool and add excess HCl( conc) with dropper
along with a wall, swirling continuously until a copious ppt is
obtained
PLAN OF WORK
OBSERVATION & CALCULATIONS :
Molar mass of benzamide 121g/mol
Molar mass of benzoic acid 122g/mol
Mass of filter paper 1.1g
Weight of ppt 0.7g
Theoretical value of benzoic acid 1.00g
Practical value of benzoic acid (%yield ) 70%
RESULTS:
 The practical yield of benzoic acid is 0.7g .
 The theoretical yield of benzoic acid is 1.00g.
 The percentage yield of benzoic acid is 70%.
CONCLUSION
Benzamide is hydrolyzed to sodium benzoate by boiling with a sodium hydroxide solution.
Sodium benzoate on acidification gives benzoic acid.
C6H5CONH2 + NaOH → C6H5COONa + HCl → C6H5COOH + NaCl
To prepare benzoic acid start with 3 grams of benzamide and mix it with 2 grams of sodium hydroxide
dissolved in about 18 mL of water in a round bottom flask. The flask is fitted with a Liebig’s condenser.
The flask is heated on a wire gauze and the contents gently refluxed for about 50 minutes.
Ammonia is evolved and the sodium salt of benzoic acid is formed in the solution.
The flask is then cooled and the contents acidified with concentrated hydrochloric acid after
transferring to a beaker.
The precipitated benzoic acid is filtered using a Buchner funnel and the yield noted. About 1 gram can be
recrystallized from hot water and the melting point can be determined to confirm the prepared compound.
MOST RECENT PUBLICATION
Comparative evaluation of hydrophilic bases for improved delivery of Benzoic acid and Salicylic
acid in antimicrobial ointment;
Abstract :
Background :Benzoic acid (BA) and salicylic acid (SA) combined are used as choice topical treatment
for fungal and bacterial infections but their delivery is affected by ointment vehicle, among other factors.
With aim to achieve improved release and antimicrobial activity in ointment formulation of these
medicaments through selection of more efficient vehicle(s), this study comparatively evaluated prospective
alternatives to the compendium-specified base for delivery potential and relevant physical properties.
Results: BA was released in relatively larger quantity and demonstrated greater antimicrobial activity than
SA in most bases. The released quantities of each medicament correlated directly with concentration and
antimicrobial activities. The rates and extents of drug release followed a similar trend in different vehicles
namely, HO > HS > NS ≥ EO > LA ≈ LH. Water number of base, ointment preparation method, viscosity,
or heat-tolerance showed no influence on drug releaseor antimicrobial activity.
Continue …..
Conclusion: HO and HS are better vehicles for delivery of BA and SA in ointment than EO
which is the prototypical base
It was published on African Journal of Clinical and Experimental Microbiology

By: A.O. Oyedele and E.O. Akinkunmi
FUTURE PLAN
Benzoic acid is the most common compound in the world , in the market overview ,
the value of benzoic acid in 2017Was around USD 868 million .
According to the US Chemical industry in 2023 benzoic acid value is USD around
1,219 million , because of the main reason for his high growth rate expectation is use
the benzoic acid in a variety Industries … as per market overview I wish to synthesis
benzoic acid from different compound at low price and sale in the market…and also
I will be very happy if I work for Pakistan chemical industry .
REFERENCE
• https://www.msdsonline.com/
• https://byjus.com/
• https://academic.oup.com/journals
• https://www.ishs.org/ishs-article/938_32

Presentation of Benzoic Acid From Benzamide

Uploaded by

Copyright:

Available Formats

Presentation of Benzoic Acid From Benzamide

Uploaded by

Document Information

Original Description:

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Presentation of Benzoic Acid From Benzamide

Uploaded by

Copyright:

Available Formats

SYNTHESIS OF BENZOIC ACID FROM

NAME : FAZAL RAHIM SHAH

PRINCIPLE :benzamide C6H5CONH2 may be hydrolyzed by aqueous acid alkali ,

which is the prototypical base

It was published on African Journal of Clinical and Experimental Microbiology

You might also like