MERITS OF MICROWAVE ASSISTED REACTIONS
DEMERITS OF MICROWAVE ASSISTED REACTIONS
MECHANISM OF MICROWAVE HEATING
EFFECTS OF SOLVENTS IN MICROWAVE ASSISTED SYNTHESIS
MICROWAVE VERSUS CONVENTIONAL SYNTHESIS
MICROWAVE INSTRUMENTATION
VARIOUS TYPES OF MICROWAVE ASSISTED ORGANIC REACTIONS
APPLICATIONS OF MICROWAVE ASSISTED REACTIONS
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A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
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When there are two functional groups of unequal reactivity within a molecule, the more reactive group can be made to react alone, but it may not be possible to react the less reactive functional group selectively.
A group the use of which makes possible to react a less reactive functional group selectively in presence of a more reactive group is known as protecting group.
A protecting group blocks the reactivity of a functional group by converting it into a different group which is inert to the conditions of some reaction(s) that is to be carried out as part of a synthetic route
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Microwave assisted reactions
1. MICROWAVE ASSISTED
REACTIONS
A Green Chemistry Approach
Prepared by- Mohamad Haider
Department of Pharmaceutical Chemistry
Roll no. – 04/MPH/DIPSAR/19
2. CONTENTS
INTRODUCTION
MERITS OF MICROWAVE ASSISTED REACTIONS
DEMERITS OF MICROWAVE ASSISTED REACTIONS
MECHANISM OF MICROWAVE HEATING
EFFECTS OF SOLVENTS IN MICROWAVE ASSISTED SYNTHESIS
MICROWAVE VERSUS CONVENTIONAL SYNTHESIS
MICROWAVE INSTRUMENTATION
VARIOUS TYPES OF MICROWAVE ASSISTED ORGANIC REACTIONS
APPLICATIONS OF MICROWAVE ASSISTED REACTIONS
REFERENCES
3. INTRODUCTION
MICROWAVE
• A microwave is a form of electromagnetic energy that falls at the lower frequency of the
electromagnetic spectrum in the range of 300 to 300,000 MHz.
• Within this region of electromagnetic energy only molecular rotation is affected not the
molecular structure. However for their use in laboratory reactions, a frequency of 2.45
GHz is preferred because it has the right penetration depth for laboratory reaction
conditions.
4. MICROWAVE ASSISTED REACTIONS
• Microwave irradiation has gained popularity in the past decade as a powerful tool
for rapid and efficient synthesis of a variety of compounds because of selective
absorption of microwave energy by molecules.
• This phenomenon is dependent on the ability of a specific material to absorb
microwave energy and convert it into heat. Microwave passes through material
and causes oscillation of molecule which produces heat.
• Microwave heating produces heat in the entire material in the same rate and at the
same time at a high speed and at a high rate of reaction.
• Microwave heating is the best process due to the microwave couple directly with
the molecule that are present in the reaction mixture, leading to fast rise in
temperature, faster reaction and cleaner chemistry.
• The microwave chemistry is also called as Green Chemistry because it does not
produce any hazardous material like gas, fumes, heating etc.
5. MERITS OF MICROWAVE ASSISTED
REACTIONS
Faster reaction
Better yield and higher purity
Energy saving
Uniform and selective heating
Green synthesis
Possibility of convenient solvent superheating
Excellent parameter control
Access to automated setups and parallel synthesis
Possibility of stirring
Continuous power output
6. DEMERITS OF MICROWAVE ASSISTED
REACTIONS
Sudden increase in temperature may led to distortion of molecules
Very vigorous and which may be hazardous
Microwave reactors are expensive and delectated
Heat force control is difficult
Water evaporation
Closed container is dangerous because it could be burst
7. MECHANISM OF MICROWAVE HEATING
All the materials are not susceptible to microwave heating as response of various
materials to microwave radiation is diverse. Microwave absorbing materials (e.g.
water) are of utmost important for microwave chemistry and three main different
mechanisms are involved for their heating namely:
• Dipolar polarization
• Conduction mechanism
• Interfacial polarization.
8. DIPOLAR POLARIZATION
For a substance to be able to generate heat when irradiated with microwaves it must
be a dipole, i.e. its molecular structure must be partly negatively and partly positively
charged. Since the microwave field is oscillating, the dipoles in the field align to the
oscillating field. This alignment causes rotation, which results in friction and ultimately
in heat energy.
IONIC CONDUCTION
During ionic conduction, dissolved (completely) charged particles (usually ions)
oscillate back and forth under the influence of microwave irradiation. This oscillation
causes collisions of the charged particles with neighboring molecules or atoms, which
are ultimately responsible for creating heat energy.
INTERFACIAL POLARIZATION
The interfacial polarization method can be considered as a combination of both the
conduction and dipolar polarization mechanisms. It is important for heating systems
that comprise a conducting material dispersed in a non-conducting material.
9. EFFECTS OF SOLVENTS IN
MICROWAVE ASSISTED SYNTHESIS
Every solvent and reagent will absorb microwave energy differently. They each have
a different degree of polarity within the molecule, and therefore, will be affected
either more or less by the changing microwave field.
A solvent that is more polar will affect more and vice versa. However polarity of the
solvent is not the only factor. Most organic solvents can be broken into three
different categories: low, medium, or high absorber, as shown:
10. MICROWAVE VERSUS CONVENTIONAL
SYNTHESIS
Conventional synthesis usually involves the use of a furnace or oil bath which heats
the walls of the reactors by convection or conduction. The core of the sample takes
much longer to achieve the target temperature. This is a slow and inefficient method
for transferring energy into the reacting system.
On the other hand in microwave assisted synthesis microwave penetrates inside the
material and heat is generated through direct microwave-material interaction.
11. Microwave-assisted synthesis has several advantages over conventional
reactions in that the microwave allows for:
• An increase in reaction rate
• Rapid reaction optimization
• Rapid analogue synthesis
• Uses both less energy and solvent
• It enables difficult compound synthesis.
A few reactions which were carried out using microwave heating compared with
conventional heating are:
12. MICROWAVE INSTRUMENTATION
Two types of microwave reactors can be used in the Laboratory:
• Multimode Microwave Reactors
• Single mode Microwave Reactors.
13. VARIOUS TYPES OF MICROWAVE
ASSISTED ORGANIC REACTIONS
MICROWAVE ASSISTED REACTIONS USING SOLVENTS:
1. Hydrolysis
• Hydrolysis of benzyl chloride with water in microwave oven gives 97 % yield of benzyl
alcohol in 3 min. The usual hydrolysis in normal way takes about 35 min.
2. Esterification
• A mixture of benzoic acid and n- propanol on heating in a microwave oven for 6 min
in conc. Sulfuric acid gives propylbenzoate.
14. 3. Oxidation
• Oxidation of toluene with KMnO4 under normal conditions takes 10-12 hr.
compared to reaction in microwave conditions, which takes only 5 min.
4. Decarboxylation
• Conventional decarboxylation of carboxylic acids involve refluxing in quinoline in
presence of copper chromate and the yields are low. However, in the presence of
microwaves decarboxylation takes place in much shorter time.
15. 5. Cycloaddition
• Cycloaducts were prepared by reaction between an amine and a substituted amide
in toluene. This reaction was carried out under microwave irradiation at 120 W at
75 °C for 1 h. The yield was 70–80 % .
6. N-Acylations
• N-Acylations were carried out using secondary amines and isocyanate in
dichloromethane under microwave irradiation (8–10 min), yielding the product in
94% yield.
16. MICROWAVE ASSISTED REACTIONS UNDER SOLVENT-FREE CONDITIONS
1. Aromatic Nucleophilic Substitutions
• Formation of Substituted Triazines are carried out using sodium phenoxide and
1,3,5-trichlorotriazine under microwave irradiation (6 min). The products, 1,3,5-
triarlyoxytriazines are obtained in 85–90% yields.
2. Deacetylation
• Conventional process takes long time and the yields are low. Use of microwave
irradiation reduces the time of deacetylation and the yields are good.
17. MICROWAVE ASSISTED REACTIONS USING SOLID LIQUID PHASE
1. O-Alkylation
• Preparations of ethers were carried out from β-naphthol using benzyl bromide and
1-butyl-3- methyl-imidazolium tetrafluoroborate under microwave irradiation (6-12
min) the products were isolated in 75-90% yields.
2. N-Alkylations
• N-Alkylations under microwave irradiation carried out in the synthesis of N-alkyl
phthalimides using phthalimide, alkyl halides, potassium carbonate and TBAB;
giving products in 45–98% yields.
18. 3. Oxidations
• Oxidation of secondary alcohols to acetone derivatives was carried out using PCC,
tetrabutylammonium bromide and dichloromethane under microwave irradiation
(6–8min), products were isolated in 70–99% yields.
4. Knoevenagel Condensation
• Knoevenagel condensation is applied in the synthesis of unsaturated acids. It was
carried out between carbonyl compounds and active methylene compounds, such
as malonic acid in water forming unsaturated acids in excellent yield and purity
under microwave irradiation.
19. MICROWAVE ASSISTED REACTIONS ON MINERAL SUPPORTS IN DRY
MEDIA
1. N-Alkylation
• N-Alkylation were carried out between piperidines and chloroalkanes in the
presence of silica as the solid support under microwave irradiation (6-10 min). N-
Alkyl products were isolated in 79- 99% yields.
2. S-Alkylation
• S-Alkylation was carrying out by the reaction between mercaptobenzene and alkyl
halides using potassium carbonate and alumina under microwave irradiation (4-10
min). Products were isolated in 70-89 % yields.
20. APPLICATIONS OF MICROWAVE
ASSISTED REACTIONS
SOME NAME REACTIONS
1. Heck reaction
• It is most important C-C bond forming reaction.
2. Suzuki reaction
• It is defined as palladium catalyzed cross coupling of aryl halide with boronic acids.
21. 3. Negishi and Kumada reaction
• It is the coupling of Grignard reagents with alkyl, vinyl or aryl halides under Ni/Pd
catalysis.
4. Multicomponent reactions
5. Ullmann condensation reaction
22. OTHER APPLICATIONS
1. Application of Microwave in material Chemistry
• The use of microwave for synthesis of inorganic solid is very efficient technique in
material chemistry. It has been used in preparation of ceramics.
2. Preparation of catalyst under microwave irradiation
• Synthesis of a high permeance NaA zeolite was prepared from an aluminate and
silicate sodium in a modified domestic microwave oven.
3. Application of Microwave in polymer synthesis
• The synthesis of polyacrylamide was studied under microwave irradiation. PAM is
used as a flocculating agent in waste water treatment .
4. Analytical Chemistry
• Microwave irradiations are routinely used for sample digestion, solvent extraction,
gravimetric and moisture determination techniques.
5. Microwave irradiation in waste management
• Microwave heating can be advantageously used for waste management in areas
where human exposure can cause health problems.
23. REFERENCES
Surati, M.A., Jauhari, S. & Desai, K.R. 2012, 'A brief review: Microwave assisted
organic reaction', Scholars Research Library, vol. 4, no. 1, pp. 645-661.
Grewal, A.S., Kumar, K., Redhu, S. & Bhardwaj, S. 2013, 'MICROWAVE
ASSISTED SYNTHESIS: A GREEN CHEMISTRY APPROACH', International
Research Journal of Pharmaceutical and Applied Sciences (IRJPAS), vol. 3, no. 5,
pp. 278-285.
Ahluwalia, V.K. & Kidwai, M. 2004. New trends in Green Chemistry : Microwave
Induced Green Synthesis. Anamaya Publishers, New Delhi. 263 pp.
https://shodhganga.inflibnet.ac.in/bitstream/10603/3197/8/08_chapter%201.pdf