microwave, assisted solvent-free synthesis of …infokara.com/gallery/51-jan-3502.pdf · microwave,...

MICROWAVE, ASSISTED SOLVENT-FREE

SYNTHESIS OF FLUORESCEIN AND ANTI-

MICROBIAL ACTIVITIES

R.RAMESH 1*, D.TAMILSELVAN3, G.M.RATHIKA2

2Selvam college of Technology Namakkal -637 003. Tamil Nadu, India.

1&3PG & Research Department of Chemistry, AVS College of Arts & Science, Salem - 636 106.

Tamil Nadu, India

*Corresponding Author Email Id: [email protected]

ABSTRACT

In the present investigation a green chemistry approach is employed, for the microwave , assisted

solvent free synthesis of fluorescein organic compound, the fluorescein were characterized by UV-

Visible, FT-IR and XRD. The fluorescein was screened for anti-microbial activity against

Pseudomonas aeruginosa – negative bacteria and Candida albicans as fungal strain. The results

exposed that the synthesis of fluorescein organic compound good anti –bacterial activity and anti-

fungal activity using various Concentration for tested microorganisms. It similarly concluded that

Microwave, assisted solvent free synthesis of fluorescein, Can be explored to find out the bio-activity

Organic Compound that may help as leads in the development of active drugs.

1. INTRODUCTION

The first application microwaves irradiation in chemical synthesis was published in 1986.1

the organic synthesis is one of the major role of research in chemistry, from plastics to

medication it participates in the improvement of everyone life. Over the past few decades,

many significant advances in practical aspects of organic chemistry have included novel

synthetic strategies and methods as well as advent of a vast array of analytical techniques. In

these environmentally conscious days, the developments in the technology are directed

towards environmentally sound and cleaner procedures2.

Microwaves are a form of electromagnetic energy, like light waves are radio waves and

occupy a part of electromagnetic spectrum of power or energy. Microwaves are very short

waves of electromagnetic energy that travel at the speed of light (186, 282 miles/sec) 3.

INFOKARA RESEARCH

Volume 9 Issue 1 2020 481

ISSN NO: 1021-9056

http://infokara.com/

mailto:[email protected]

Every microwave oven contains a magnetron, a tube in which electrons are affected by

magnetic and electric fields in such a way as to reduce micro wavelength radiation at a about

2450 Mega Hertz(MHz) or 2.45 Giga Herts (GHz). All wave energy changes polarity from

positive to negative with each cycle of the wave. In microwaves, these polarity changes

happen millions of times every second.

Microwave has been used to speed up chemical reactions in the laboratories, which led

scientists to investigate the mechanism of microwave dielectric heating and to identify the

advantages of the technique for chemical synthesis4. During recent years, microwaves have

been extensively used for carrying out chemical reactions and have become a useful non-

conventional energy source for performing organic synthesis. This is supported by a great no

of publications in recent years, particularly in 2003, related to the applications of microwaves

as a consequence of a great availability of dedicated and reliable microwave instrumentation.

In the electromagnetic spectrum the microwave radiation region is located between Infrared

radiation and microwaves. Telecommunication and microwave radar equipment occupy many

of the band frequencies in this region. In order to avoid interference with these systems, the

household and industrial microwave ovens operate at a fixed frequency of 2.45 GHz. The

energy of the quantum involved can be calculated by the Planck’s law C=hv and is found to

be 0.3 cal mol-1. In the case of the microwave assisted reactions using (organic) solvents, the

reactants are dissolved in the solvent, which often couples effectively with microwaves and

thus acts as the energy transfer medium. When microwave irradiation is off, classical thermal

chemistry takes over, losing the full advantage of microwave irradiation, which is used to

reach TB faster. Microwave enhancement of chemical reactions will only take place during

the applications of microwave energy. This source of energy will directly activate the

molecules in a chemical reaction, and therefore it is not desirable to suppress its application.

INFOKARA RESEARCH


ISSN NO: 1021-9056


EMS ensures that a high, Constant level of microwave energy is applied, resulting in the

significantly greater yields and cleaner chemistries5.

2. APPLICATION OF MICROVAVE

2.1. Preparation of catalyst under microwave irradiation6

Synthesis of a high per menace NaA zeolite YBa2Cu3O7-X membrane was prepared from an

aluminate and silicate sodium with molar ratio of 5SiO2: Al2O3: 50Na2O: 1000H2O in a

modified domestic microwave oven operating at 2450 MHz in 15 min. it was observed that

the per menace of the zeolite membrane synthesized by the microwave heating is 4 times

higher than that of the zeolite membrane synthesized by conventional heating.

2.2. Application of Microwave technology for Nanotechnology7

Today nanotechnology is being applied in the fields of synthesis of single-site catalyst,

antimicrobial Nano composites, fire retardant materials, novel electro-optical devices sensors,

ultra soft magnets and also in the area of drug delivery systems.

2.3. Analytical Chemistry8

The application of microwave irradiation is immense in the field of analytical chemistry.

Microwave irradiations are routinely used for sample digestion and solvent extraction

techniques. They have also been put to use for gravimetric, moisture determination and to

find out enthalpy of vaporization of solvents.

2.4. Microwave irradiation in waste Management9

Microwave heating is playing an important role in treatment of domestic and hazardous

industrial and nuclear waste. Microwave heating can be advantageously used for waste

management in areas where human exposure can cause health problems. The microwave and

INFOKARA RESEARCH


ISSN NO: 1021-9056


high frequency technology needed for handling such type of hazardous waste is ready to use.

A process for carbonization of organic waste for manufacturing of activated carbon using

microwave heating has been patented by Kasai et al10.Activted carbon can be manufactured

from organic wastes such as used paper, wood, waste plastic etc.in high carbonization

efficiency using microwave heating. The method and apparatus for continuous and batch

process is developed for waste treatment by Roszel. In the process waste such as automobile

shedder waste, medical waste, ores, sludge etc. are treated by microwave energy in anaerobic

atmosphere.

2.5. Microwave and green Chemistry 11

Microwave is a convenient way towards the goal of green/sustainable chemistry, and is

strongly recommended to use in organic preparations. The examples cited above are

impressive and provide a good insight into the field of microwave assisted organic synthesis.

The benefits of microwave-assisted organic synthesis are increasingly making the technique

more established worldwide. In order to achieve further development in this field, novel

instruments which give rise to reproducible performance and that constitute a minimal hazard

should be used instead of the domestic microwave ovens12.

Filtrate dilute hydrochloric acid (35ml) was added and precipitated was filtered, washed with

cold water and recrystallized from methanol.

2.6. MELTING POINT

Fluorescein

The pinch of substance (Fluorescein) has been taken in the capillary tube and placed in

melting point apparatus. The temperature of the substance is observed until it gets changing

from solid phase to liquid phase. The temperature is noted at 3140C. This temperature was

INFOKARA RESEARCH


ISSN NO: 1021-9056


confirmed by comparing to the reported melting temperature value in the range of 3130C-

3150C

Table 1.Representation melting point of synthesized organic compound

S.NO

Name of the

compound

Observed value (0C)

Reported value

(0C)

1.

Fluorescein

314 (0C)

313-315 (0C)

2.1. Fluorescein

Silicon dioxide coated in glass plate. Small amount of sample dissolved in methanol now one

drop of benzophenone oxide solution and solvent and reactant now the glass plate dip in

Ethylaceate: Chloroform (1:9) solution bath. After 10 minutes 3 different color noted in three

different distance calculated Rf value (0.43).

Table 2.Rrepresentation Rf of synthesized organic compound

S.NO

Name of the

compound

Mobile Phase

Rf value

1.

Fluorescein

Ethylacetate:Chloroform(1:9)

0.43

INFOKARA RESEARCH


ISSN NO: 1021-9056


3. EXPERIMENTAL METHODS

3.1. Synthesis of Organic Compounds

Fluorescein

A mixture of phthalic anhydrite (7.5 g: 0.05M) and resorcinol (11 g: 0.1 M) were taken in a

100ml conical flask. After covering with funnel, the mixture was irradiated with microwave

60% (540 W) intensity for 180 sec. A beaker containing water was placed in the oven next to

reaction vessel to serve as a “heating sink”. Then reaction mixture was cooled and stirred for

15 minutes. The separated product was filtered, dried and recrystallized from ethanol.

4. RESULT AND DISCUSSION

4.1. UV-Vis spectra of the compound Fluorescein

The UV-Visible spectra of Fluorescein were Determine the fundamental electron transitions

present in functional groups. The spectra of Fluorescein show four bands such as 213.15nm,

289.75nm, 298.45 nm, and 740.40 nm respectively. The bands are represented by Fluorescein contains

alkenes groups. such as 212.50 nm, 330.65 nm and 742.85 nm respectively. The bands are represented by

Phthalimide contains alkenes groups.

INFOKARA RESEARCH


ISSN NO: 1021-9056


Fig 1. UV-Vis spectra of the compound Fluorescein

4.2. FT-IR spectrum of the compound Fluorescein

The compound fluorescein is prepared by microwave oven method. The percentage yield of

the product is 84.5%. The measured melting point value is 314oC. The value is agreed with

the standard value (313-315) and the Rf value is 0.43.

The FT-IR spectra of Fluorescein are show in Fig 3 and its absorption frequencies are given

in Table 2. The absorption bands at 3200-3600cm-1 are assigned to υ O-H stretching of

alcohols. The appearance of a band at 2500-3100 cm-1 indicates the presence of υ O-H stretching of

carboxylic acid. The peaks 1500-2000 cm-1 indicates the presence of υ C-O stretching of alcohol.

The peaks 500-1000 cm-1 indicates the presence of υ C-H Bend of alkenes.

INFOKARA RESEARCH


ISSN NO: 1021-9056


Fig 2. FT-IR spectra of Organic Compound Fluorescein

4.3. X-Ray Diffraction Analysis (XRD)

The X-Ray Diffraction Analysis of Microwave – Assisted Solvent Fluorescein are shown in

Fig 3. The XRD analysis was selected for the diffraction angle range θ. The results obtained

that, X-Ray diffraction spectra of Microwave – Assisted Solvent Fluorescein, indicate four

strong peaks appeared at 13.0148o, 17.1002o, 23.3786o, and 25.2914o.

Fig 3. X-Ray Diffraction Analysis (XRD) Organic Compound Fluorescein

SJC-7-C20H12O5-

Name Description

4000 4003500 3000 2500 2000 1500 1000 500

100

0

10

20

30

40

50

60

70

80

90

cm-1

%T

1763.32cm-1

904.81cm-1

1 2 5 5 . 4 3 c m - 1

1848.44cm-1

710.40cm-1

1597.58cm-18 3 8 . 1 8 c m - 11103.83cm-1

1464.93cm-1

1168.84cm-11 3 5 6 . 9 9 c m - 1

799.81cm-1

1338.73cm-1

529.40cm-13092.74cm-1

3064.53cm-1

640.55cm-1

1517.25cm-12639.14cm-1

2687.55cm-1

3600.25cm-1 2528.86cm-1

3571.34cm-1

2347.63cm-1

1003.69cm-1

3366.87cm-1 2012.87cm-1

2165.16cm-1

2267.80cm-1

2093.64cm-1

3886.95cm-1

INFOKARA RESEARCH


ISSN NO: 1021-9056


Antibacterial activity of Microwave-Assisted Solvent

The Fluorescein were using different concentration as 25µl, 50µl, 75µl and 100µl, The

Fluorescein were a zone of inhibition bacteria like 8,12, 15 and 20 µm respectively. The

antibacterial activity of Fluorescein against using a standard drug Ciprofloxacin. The

Fluorescein compared to the standard drug in the zone of inhibition minimum inhibition

activity. So that the Fluorescein were may be useful for antibacterial activity. From the

positive control zone of inhibition 22µl and Fluorescein 20µl. Shown less antibacterial activity

against Pseudomonas aeruginosa.

Fig 4. The Antibacterial activity of Organic Compound Fluorescein against Pseudomonas aeruginosa

Table: 3 Antibacterial Activity of Organic Compound Fluorescein

S.NO

Sample

Control

Zone of Inhibition ( mm)

25µl 50µl 75µl 100µl

1.

Fluorescein

22

8

12

15

20

INFOKARA RESEARCH


ISSN NO: 1021-9056


Fig 5. The Antibacterial activity of Organic Compound against Pseudomonas aeruginosa

Antifungal Activity of Microwave-Assisted Solvent

The Fluorescein were using different concentration as 25µl, 50µl, 75µl and 100µl, The

Fluorescein were a zone of inhibition fungal like 5,12, 17 and 20 µm respectively. The

antibacterial activity of Fluorescein against using a standard drug fluconazole The Fluorescein

compared to the standard drug in the zone of inhibition minimum inhibition activity. So that

the Fluorescein were may be useful for antifungal activity. From the positive control zone of

inhibition 22µl and Fluorescein 20µl.Shown less antifungal activity against Candida albicans.

Fig 6. The Antifungal activity of Organic Compound against Candida albicans

Table: 4 Antifungal Activity of Organic Compound Fluorescein

S.NO

Sample

Control

Zone of Inhibition ( mm)


1. Fluorescein 22 5 12 17 20

0

5

10

15

20

25


Zon

e o

f In

hib

itio

n in

mm

Concentration

Fluorescein With Pseudomonas aeruginosa

25µl

50µl

75µl

100µl

INFOKARA RESEARCH


ISSN NO: 1021-9056


Fig 7. The Antifungal activity of Organic Compound against Candida albicans

5. CONCLUSIONS

The Compound Fluorescein has been synthesized. The structure of the compounds is

determined by physical constant, Rf Value and UV-Visible spectra, FT-IR and XRD. The

tentative structure of the compounds.The fluorescein was screened for anti-microbial activity

against Pseudomonas aeruginosa – negative bacteria and Candida albicans as fungal strain. The

results exposed that the synthesis of fluorescein organic compound good anti –bacterial activity and

anti-fungal activity using various Concentration for tested microorganisms. It similarly concluded

that Microwave, assisted solvent free synthesis of fluorescein, Can be explored to find out the bio-

activity Organic Compound that may help as leads in the development of active drugs.

0

5

10

15

20

25


Zon

e o

f In

hib

itio

n in

mm

Concentration

Fluoresein With Candida albicans

25µl

50µl

75µl

100µl

INFOKARA RESEARCH


ISSN NO: 1021-9056


REFERENCES

1. KR Desai, Green Chemistry Microwave synthesis, First Edition, Himalaya

Publication House, India 2005.

2. A Hoz de la; A Dfaz; A Moreno; Chem. Soc. Re; 34; 164-178, 2005

3. DMP Mingos; AG Whittaker; RV Van; C Malik; D. Hubbard Spektrum

Akademischer Verlag Co-Publication, New York and Heidelberg, 479, 1997.

4. AK Bose; MS Manhas; BK Banik; EW Robb; Res.Chem. Intermed; 20; 1-11, 1994

5. MN Gedye; FE Smith; KC Westaway; Can J; Chem, 66, 17, 1998

6. RN Gedye; E Smith; K Westaway; H Ali Baldisera; L Laberge; J Rousell;

Tetrahedron Lett; 27; 279, 1986

7. JP Tiernwy; P Lindstrom; Microwave-assisted Organic Synthesis, Eds., Blackwell,

Oxford 2005.

8. P Lindstrom; J Tierney; B Wathey; J Westman; Tetrahedron; 57;

9225-9283, 2001

9. JA Seijas; MP Vazquez-Tato; MM Martinez; GN Corredoria; J. Chem. Res. (S);

420-425, 1999

10. Z Dahmani; M Rahmouni; R Brugidou; JP Bazureau; J Hamelin; Tetrahedron Lett;

39; 8453-8456, 1998

11. D Scharn; H Wenschuh; U Reineke; J Schneider-Mergener; L. Germeroth; J. Comb.

Chem.; 2; 361-369, 2000

12. D Bogda; J Pielichowski, A Borona, Synlett, 873-874, 1996.

INFOKARA RESEARCH


ISSN NO: 1021-9056


microwave, assisted solvent-free synthesis of …infokara.com/gallery/51-jan-3502.pdf · microwave,...

Documents