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6 :
Momin Saeed Shah
For Course : Pol mer Laborator
CHM6401)
MSc Pol mer & Pol mer Composite Science &
Engineering
2010/2011
Date : 6th Dec. 2010

The Universit of Sheffield

Department of Chemistr c

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£ florenol is oxidized to £ fluorenone using pol mer bound chromium
)oxide reagent.

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Pol mer bound reagents have originate extensive use in organic s nthesis during the past
few ears. n short the reagent is bound to the structure of the pol mer where it reacts with
the substrate, in solution.The product being still in solution is easil separated from the solid
pol mer with its bound
reacted) reagent. deall s nthesis should involve a rec clable
pol mer and cheap reagent, should result in a cr stalline product and should be
successfulon semi micro scale. Obviousl not all of these ideal can be met in practice , but
nevertheless , pol mer bound reagents often offer facile s nthesis.

AM6ERLYSTΠA26  is a strong basic , anionic, macro reticular pol meric resin based
on crosslinked st rene divin lbenzene copol mer containing quaternar ammonium groups,
formulated especiall for aqueous media.

Strongl basic anion exchange resin used to remove transition metal complexes in this case
Chromium
)Oxide and mercaptans from h drocarbons, remove acids from non polar solvents,
and deacidif ing phenol acetone solutions. ts porous structure makes it a good pol meric catal st
in non aqueous and aqueous media; it has no pH limitations. Strongl basic, macroreticular resin
with quaternar ammonium functionalit used to catal ze aldol condensation useful in aqueous and
nonaqueous media to remove anionic transition metal complexes, mercaptans, and acids from
h drocarbons and other nonpolar solvents.

Materials & Methods

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c.Spatula ,Hot Plate , rubber pipes , rotar evaporator , Safet Equipments i.e Lab
coat , safet glasses , rubber gloves
anti corrosive),capillar tubes.melting point equipment
, FTR Spectrometer.

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Amberl st A 26 OH , Chromium
)Oxide , £ fluorenol , propanone , hexane , ethanol ,

distilled water ,TLC strips ,

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Setup a suitable Fume cupboard with a good Prepare a pol mer bound CrO 3 
use a magnetic stirrer to stir a mixture of 10g  of Amberl st A 26 resin
or 5g of
dr resin) in 20cm 3 of saturated aqueous CrO 3 for half hour at room temperature.
Collect the pol mer b vacuum filteration than wash it with 100cm 3 of propanone.
Dr the pol mer either b leaving it to dr in the 6uchner funnel under suction for
half hour or b allowing it to air dr overnight. The ield of the pol mer was about
5 g of dr oxidizing pol mer.The oxidizing pol mer is now read to use.
On the other side for the oxidation of £ fluoronol, add 1 gm of £ fluoronol with 5 g
of the prepared oxidizing pol merand 35cm 3 of toluene in a quickfit conical flask
and heat under reflux with magnetic stirring for an hour. The technique of thin
la er chromatograph
TLC) is used simultaneousl to observe the progress of
the sample. 6 taking the sample of the solution ever 15 mins. The TLC is done
on a fluorescent silica gel , eluated with propanone:hexane
1:3) and visualize
using U. light. When it is observed that reaction is complete remove the pol mer
b filteration. Remove the solvent b using rotar evaporator.Now recr stallize
the resdue from ethanol/water.Observe the %age ield and melting point of pure
dr £ fluorenone.Run a sample of the product in FTR and obtain the spectra of
the product also run for the starting material spect ra.

Results :

Theoreticall

Œ c 
cŒc
c c
cc
cccccccccc

cO
c H cO

6alanced ratio 1:1

1 g of £ fluorenol
182 g), 1/182 =0.0054£ moles should give 0.0054£ moles of £

fluorenone
180 g ) therefore 0.0054£x180 = 0.£882 g

Theoretical ield is 0.£882 g

Actual ield
 



So % ield = 0.22 / 0.£882 x 100

=  !"
Melting Point :

Melting point in Literature is : 83.5ºC

Actual Melting Point : o #

FTR Spectra :

See attached R Spectra in Appendix

The R spectra of starting material shows the stretch C OH
which should be between
3200cm 1 to 3550 cm 1)[1] at 3284 cm 1 .Which shows the presence of OH group attached to
the structure of £ fluorenol.The Aromatic C=C and C H between 1700 1500[1] and 860 680
[1]
respectivel are ver intense due to the dual benze ne ring presence.

The R spectra of the product £ Fluorenone has no visible peak between 3200 to 3550 i.e
C OH peak missing with means no presence of h drox l group in the product sample.
simultaneousl the ketonic C=O stretch at
which should be between 1780 and 1650) [1]
1711 is clearl visible which shows the presence of the Ketonic RCOR group in the
structure of the product. Rest all other peaks are similar as no furher drastic change in the
spectrum.These R Spectra dentities claims that the produc t is £ flourenone.
Discussion :

+ H Cl
H 3O H 2O
HOCl O +

H
H OH H O H

Cl
O
+ H H
H 3O

H O
O
Cl
H H

H 3O +

+ H 3O +
+ Cl

The green Oxidaton using household bleach

the mechanism results in the exchange of a Cl + with a H+ on ox gen, followed b

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subsequent elimination of HCl to form the ketone. Sodium h pochlorite is the
mainingredient in bleach. t must first be converted to h pochlorous acid in order to
oxidize the alcohol. HOCl is a source of a positive Cl, which has 2 fewer electrons
than a chloride anion.

Conclusion :
References :

http://www.chem.ucla.edu/~webspectra/irtable.html

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