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Name of Student : SIOW WEI JIAN, SAMUEL
Matric No. : 1003488B
Care Group : A10D4
Name of Company : Institute of Materials Research and Engineering
Company Supervisor : Dr CHO CHING MUI
TP Liaison Officer : Dr WUANG SHY CHYI
Diploma in Chemical Engineering
AY 2012/2013
Project Title
Synthesis of donor-acceptor monomers for conjugated
electrochromic polymers
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Table of ContentsExp no. Title Page no.
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Date: 25/04/12
Title: Introduction to column chromatography.
Objectives: The purpose of column chromatography is to separate complexmixture of compounds.
Apparatus ChemicalsColumn, 1Conical Flask, 20Thin Layer Chromatography plates1L, One Necked, Round Bottom Flask,1Beaker, 3
Unknown Chemical MixtureSilica GelDichloromethane
Procedures
1. A column was filled up with 250g of silica gel via continuous stirring withdichloromethane/hexane (50:50) v/v batch wise.
2. A filter paper was added to the top of the silica packing.3. The chemical mixture was loaded into the column via a dropper, drop
wise. Ensuring the silica packing remained undisturbed.4. The column was left to run for 9hrs with continuous addition of solvent.5. Fractions of eluent were collected in multiple, 50ml conical flask.6. Using thin layer chromatography, fractions of similar purity were
combined in a 1L, one necked, round bottom flask and concentrated onthe rotary evaporator.
Observations
Step 6: A colorless solution was formed.
Results
One product was collected
Discussion
Column chromatography is an important chemical laboratory technique fororganic synthesis. Many techniques like using a rotary evaporator and using adeuterium lamp to identify eluting products are important to take note in futureexperiments.
Conclusion/Recommendations
In future experiments, apparatus should be wash and place in the oven
overnight. A reservoir could also be used to reduce repetition instead of refillingeluent.
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Experiment 1 Batch 1
Date: 24/4/12
Title: Synthesis of 3,4-Dibromo-2,5- diformylthiophene.
Objectives: The purpose of this experiment is to synthesize 3,4-Dibromo-2,5-
diformylthiophene.
Theoretical
(1) (2) (3) (4)Mole Ratio 1 2 2.25 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1 0.32 0.637 0.745No.of moles(mmol)
2.50 5.00 5.63 2.50
Volume (ml) - 3.125 0.625 -Concentration - 1.6M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 12ml
Volume of 6M, Hydrochloric acid: 6.25ml
Apparatus Chemicals25ml, three neck, round bottom flask,1
Magnetic Stir Bar, 1Rubber Septum, 2Bubbler, 1Argon inlet flowDry ice/Acetone BathIce/ Water BathVacuum Oven
TetrabromothiopheneTetrahydrofuran
Butyl LithiumN-formylpiperidineHydrochloric Acid
Actual
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(1) (2) (3) (4)
Mole Ratio 1 2 2.25 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1.009 - 0.642 -No.of moles(mmol)
2.52 5.04 5.67 2.52
Volume (ml) - 3.6 0.630 -Concentration - 1.4M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 12ml
Volume of 6M, Hydrochloric acid: 6.25ml
Procedures
1) A oven dried, 25ml, three necked, round bottom flask equipped withmagnetic stir bar, two rubber septum, with an argon inlet and placed on ahot plate was setup.
2) 1.009g of Tetrabromothiophene and 12ml of tetrahydrofuran was addedto the setup.
3) The set up was then cooled to -80oc with a dry ice/acetone bath.4) 3.6ml of 1.4M butyl lithium was added via a syringe dropwise, taking
15mins.5) The solution was stirred for another 30mins.6) 0.630ml of Dry N-formylpiperidine was added to the mixture quickly.7) The solution was left to warm to ambient temperature overnight.8) The solution was cooled to 0oc using an ice/water bath.9) 6.25ml of 6M HCl was added to the mixture
Note: Experiment was terminated after step 9; no precipitate was formed.
Observations
Step 7: The solution turned brown.
Step 9: The solution remained brown with a layer of oil on the surface.
Results
Experiment was not completed. No precipitate form.
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Discussion
At step 9, a small volume of yellow precipitate should form as an indication thatthe 3,4-dibromo-2,5-diformylthiophene is formed. However, in this experiment,no precipitate was observed. A possible explanation is the oxidation of
butyllithium in air. Using the appropriate amount of butyllithium in this
reaction is crucial in the structure of product form. In this case, the amount wassubstantially lesser than expected. No precipitate was even form in excess of HCland removal of solvent on the rotary evaporator.
Conclusion/ Recommendation
In the next experiment, the stopper should be tightly sealed and a larger argoninlet is recommended. Butyllithium volume added should be precise.
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Date: 30/4/12
Title: Simple Distillation of Dichloromethane
Objective:
To obtain dry dichloromethane using simple distillation. Practice setting up of apparatus in the fume hood
Apparatus Chemicals
Filter Funnel
Retort Stand
Hot Plate
1L One-necked, Round Bottom FlaskMagnetic Stir Bar
Spatula
Ice
Silicone oil
4 Molecular Sieve
Calcium hydrideDichloromethane
Procedures
1) A 1L one-necked round bottom flask, equipped with a magnetic stir bar,condenser and a water cooler pump was filled with 700ml ofdichloromethane
2) spatulas of calcium hydride were added into the boiling flask3) The solution was heated to 39.6C4) The compound was left to distill for 5 hrs5) The first few drops of the distillate were disposed6) The distillate was collected in 250ml round bottom flask
Note: The hot plate conditions were set at 460rpm and temperature set point of39.6 degrees Celsius.
Observations
The solution was colorless throughout the experiment.
Results
Dry dichloromethane was collected.
Discussion
Time taken to distill was very long.
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Conclusion/ recommendations
The round bottom flask can be wrapped with an insulating material to preventheat loss to the surroundings. An indicator could also be added to the mixture toidentify its collection timing.
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Experiment 1 Batch 2
Date: 8/5/12
Title: Synthesis of 3,4-Dibromo-2,5- diformylthiophene.
Objectives: The purpose of this experiment is to synthesize 3,4-Dibromo-2,5-
diformylthiophene.
Theoretical
(1) (2) (3) (4)Mole Ratio 1 2 2.25 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1 0.32 0.637 0.745No.of moles(mmol)
2.50 5.00 5.63 2.50
Volume (ml) - 3.125 0.625 -Concentration - 1.6M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 12ml
Volume of 6M, Hydrochloric acid: 6.25ml
Apparatus Chemicals50ml, three neck, round bottom flask,1
Magnetic Stir Bar, 1Rubber Septum, 2Bubbler, 1Nitrogen inlet flowDry ice/Acetone BathIce/ Water BathVacuum Oven
TetrabromothiopheneTetrahydrofuran
Butyl LithiumN-formylpiperidineHydrochloric Acid
Actual
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(1) (2) (3) (4)
Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 0.9999 - 0.637 -No.of moles(mmol)
2.50 5.50 6.05 2.50
Volume (ml) - 6.11 0.698 -Concentration - 0.9M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 20ml
Volume of 6M, Hydrochloric acid: 16ml
Procedures
1) A oven dried, 50ml, three necked, round bottom flask equipped withmagnetic stir bar, two rubber septum, with an nitrogen inlet and placedon a hot plate was setup.
2) 0.9999g of Tetrabromothiophene and 20ml of tetrahydrofuran was addedto the setup.
3) The set up was then cooled to -80oc with a dry ice/acetone bath.4) The system was left to purge for 1 hr with N2 gas5) 6.11ml of 0.9M butyl lithium was added via a syringe dropwise, taking
15mins.6) The solution was stirred for another 30mins at -77 oc.7) 0.7ml of Dry N-formylpiperidine was added to the mixture quickly.8) The solution was left to warm to ambient temperature overnight.9) The solution was cooled to 0oc using an ice/water bath.10)16ml of 6M HCl was added to the mixture11)The solution was left to stir for 45mins at 0oc.12)The solid was the filtered under vacuum on a Buchner funnel.13)The residue was left to dry overnight in a vacuum oven.
Note: Residue collected was insignificantly small; experiment is void.
Observations
Step 7: The solution turned yellow/brown.
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Step 9: A yellow precipitate was formed.
Results
Small insignificant amounts were present.
Discussion
In comparison to the first batch, solids form at step 10 was more significant.However, only a small amount of solid is present after suction filtration on theBuchner funnel, this could be due to the larger mole ration used (1:2.2). thepurging time foe the system was also lengthen.
Conclusion/ Recommendations
A longer reaction time can be given between Butyl Lithium andTetrabromothiophene.
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Experiment 1 Batch 3
Date: 10/5/12
Title: Synthesis of 3,4-Dibromo-2,5- diformylthiophene.
Objectives: The purpose of this experiment is to synthesize 3,4-Dibromo-2,5-
diformylthiophene.
Theoretical
(1) (2) (3) (4)Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1 0.32 0.686 0.735No.of moles(mmol)
2.50 5.51 6.06 2.50
Volume (ml) - 3.125 0.673 -Concentration - 1.6M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 12ml
Volume of 6M, Hydrochloric acid: 6.25ml
Apparatus Chemicals50ml, three neck, round bottom flask,1
Magnetic Stir Bar, 1Rubber Septum, 2Bubbler, 1Nitrogen inlet flowDry ice/Acetone BathIce/ Water BathVacuum Oven
TetrabromothiopheneTetrahydrofuran
Butyl LithiumN-formylpiperidineHydrochloric Acid
Actual
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(1) (2) (3) (4)
Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1.001 - 0.686 0.1686No.of moles(mmol)
2.50 5.51 6.06 2.50
Volume (ml) - 6.11 0.698 -Concentration - 0.9M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 20ml
Volume of 6M, Hydrochloric acid: 19ml
Procedures
1) A oven dried, 50ml, three necked, round bottom flask equipped withmagnetic stir bar, two rubber septum, with a nitrogen inlet and placed ona hot plate was setup.
2) 1.001g of Tetrabromothiophene and 20ml of tetrahydrofuran was addedto the setup.
3) The set up was then cooled to -78oc with a dry ice/acetone bath.4) The system was left to purge for 3 hrs with N2 gas5) 6.11ml of 0.9M butyl lithium was added via a syringe drop wise, taking
15mins.6) The solution was stirred for another 1hr at -78 oc.7) 0.7ml of Dry N-formylpiperidine was added to the mixture quickly.8) The solution was left to warm to ambient temperature overnight.9) The solution was cooled to 0oc using an ice/water bath.10)19ml of 6M HCl was added to the mixture11)The solution was left to stir for 45mins at 0oc.12)The solid was the filtered under vacuum on a Buchner funnel.13)The residue was left to dry overnight in a vacuum oven.
Observations
Step 8: The solution turned from colorless to yellow.
Step 10: A yellow precipitate was formed together with a layer of oil on thesurface.
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Step 13: A crude brown solid was formed.
Results
Mass of vial + cap: 22.1015g
Mass of vial + cap + solids: 22.2714g
Mass of solid: 0.1686g
Percentage Yield: 0.1686/0.735*100% = 22.9%
Discussion
In this experiment, there is a slight variation to the 2nd batch. The time allowedfor Butyl Lithium to react was increased from 30minutes to 1 hour. There is alsoa larger precipitate produced upon the addition of hydrochloric acid. However,
the solid collected did not prove to be substantial, this could be due to thedecomposition of Butyl Lithium.
Conclusion/ Recommendations
The reaction is considered complete. However, several improvements like alonger reaction time and the transfer methods of chemical can be reconsidered.
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Date: 15/5/12
Title: Determining the Concentration of Butyl Lithium using titration
Purpose: Butyl Lithium is a highly reactive compound, it decomposes easily. Titration is
required to determine the concentration of butyl lithium.
Apparatus Chemicals25ml, three necked, Round Bottom Flask, 1Magnetic Stir Bar, 1Rubber Septum, 2Argon InletBubbler
Biphenyl-4-methanolUnknown concentration Butyl LithiumTetrahydrofuran
Procedures
1. A 25ml, three necked round bottom flask, equipped with a magnetic stir bar, tworubber septum, stop cocked with an argon inlet was placed on a hot plate.
2. 0.184g (1mol) of biphenyl-4-methanol and 6ml of dried tetrahydrofuran wasadded to the setup.
3. The system was left to purge for 30 minutes4. The unknown concentration of Butyl Lithium was added drop wise via a syringe
till the solution change to purple/blue.
Observations
Step 2: A cloudy solution was formed.
Step 4: The solution turned to purple/blue.
Results
Volume of Butyl Lithium used to titrate: 1.25ml
Concentration of Butyl Lithium: 0.81M
DiscussionButyl Lithium is a very highly reactive compound. This titration is only aestimation of the current concentration of Butyl Lithium. The color change topurple/blue is only substantial if it last for more than a minute.
Conclusion/ Recommendations
A longer purging time is recommended to increase the accuracy of the titration.A syringe with lesser systematic error could be used.
Calculations1 mole of Bi-phenyl-4-methanol reacts with 1 mole of Butyl Lithium
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Concentration of Butyl Lithium= (1.25ml/mol)-1=0.81M
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Experiment 1 Batch 4
Date: 15/5/12
Title: Synthesis of 3,4-Dibromo-2,5- diformylthiophene.
Objectives: The purpose of this experiment is to synthesize 3,4-Dibromo-2,5-
diformylthiophene.
Theoretical
(1) (2) (3) (4)Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 2 - 1.3704 1.4897No.of moles(mmol)
5.00 11.01 12.11 5.00
Volume (ml) - 13.58 0.673 -Concentration - 0.9M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 25ml
Volume of 6M, Hydrochloric acid: 12.5ml
Apparatus Chemicals100ml, three neck, round bottom flask,1
Magnetic Stir Bar, 1Rubber Septum, 2Bubbler, 1Nitrogen inlet flowDry ice/Acetone BathIce/ Water BathVacuum Oven
TetrabromothiopheneTetrahydrofuran
Butyl LithiumN-formylpiperidineHydrochloric Acid
Actual
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(1) (2) (3) (4)
Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 2.0001 - 1.3704 No yieldNo.of moles(mmol)
5.00 11.01 12.11 5.00
Volume (ml) - 13.5 1.4 -Concentration - 0.81M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 35ml
Volume of 6M, Hydrochloric acid: 40ml
Procedures
1) A 100ml, three necked, round bottom flask equipped with magnetic stirbar, two rubber septum, with an argon inlet and placed on a hot plate wassetup.
2) 2.0001g of Tetrabromothiophene and 35ml of tetrahydrofuran was addedto the setup.
3) The set up was then cooled to -77oc with a dry ice/acetone bath.4) The system was left to purge for 30mins with Argon gas5) 13.5ml of 0.81M butyl lithium was added via a syringe drop wise, taking
20mins.6) The solution was stirred for another 2hours at -78 oc.7) 1.4ml of Dry N-formylpiperidine was added to the mixture quickly.8) The solution was left to warm to ambient temperature overnight.9) The solution was cooled to 0oc using an ice/water bath.10)40ml of 6M HCl was added to the mixture
Note: Experiment stopped at step 10; no precipitate formed
Observations
Step 7: The solution turned from colorless to yellow.
Step 8: The solution turned from yellow to reddish brown.Step 10: A layer of oil was present on the surface of the liquid. No particulateswere present.
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Results
Experiment was not completed. No precipitate form
Discussion
At step 8, the solution turned reddish brown. This is different from all the
previous experiments; this could be because the solution may not have reacted,when the butyl lithium was added. No particulates were present in step 10showing that majority of the starting materials were unreacted/underreacted.
Conclusion/ Recommendations
Butyl lithium could be added in a longer duration of time and left to react for alonger period of time.
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Experiment 1 Batch 5
Date: 16/5/12
Title: Synthesis of 3,4-Dibromo-2,5- diformylthiophene.
Objectives: The purpose of this experiment is to synthesize 3,4-Dibromo-2,5-
diformylthiophene.
Theoretical
(1) (2) (3) (4)Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 2 - 1.3704 1.4897No.of moles(mmol)
5.00 11.01 12.11 5.00
Volume (ml) - 13.58 0.673 -Concentration - 0.9M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 25ml
Volume of 6M, Hydrochloric acid: 12.5ml
Apparatus Chemicals100ml, three neck, round bottom flask,1
Magnetic Stir Bar, 1Rubber Septum, 2Bubbler, 1Nitrogen inlet flowDry ice/Acetone BathIce/ Water BathVacuum Oven
TetrabromothiopheneTetrahydrofuran
Butyl LithiumN-formylpiperidineHydrochloric Acid
Actual
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(1) (2) (3) (4)
Mole Ratio 1 2.2 2.42 1M.W (g/gmol) 399.72 64.06 113.16 297.93Mass (g) 1.9998 - 1.3704 0.1637No.of moles(mmol)
5.00 11.01 12.11 5.00
Volume (ml) - 13.58 1.4 -Concentration - 0.81M - -
Density - - 1.019g/cm3 -
Volume of Tetrahydrofuran: 38ml
Volume of 6M, Hydrochloric acid: 40ml
Procedures
1) A 100ml, three necked, round bottom flask equipped with magnetic stirbar, two rubber septum, with an argon inlet and placed on a hot plate wassetup.
2) 1.9998g of Tetrabromothiophene and 38ml of tetrahydrofuran was addedto the setup.
3) The set up was then cooled to -78oc with a dry ice/acetone bath.4) The system was left to purge for 2 hours with Argon gas5) 13.5ml of 0.81M butyl lithium was added via a syringe drop wise, taking
20mins.6) The solution was stirred for another 2hours at -78 oc.7) 1.4ml of Dry N-formylpiperidine was added to the mixture quickly.8) The solution was left to warm to ambient temperature overnight.9) The solution was cooled to 0oc using an ice/water bath.10)40ml of 6M HCl was added to the mixture11) The solution was left to stir for 45mins at 0oc.12)The solid was the filtered under vacuum on a Buchner funnel using
suction filtration.
13)The residue was left to dry overnight in a vacuum ovenNote: The solid was left to dry for 5 days in vacuum oven.
Observations
Step 7: The solution turned from colorless to yellow.
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Step 10: A yellow precipitate was formed and a layer of oil was present on thesurface.
Step 13: A crude brown solid was formed.
Results
Mass of vial + cap: 21.9936g
Mass of vial + cap + solids: 22.1573g
Mass of solid: 0.1637g
Percentage Yield: 0.1637/1.4897*100% = 10.99%
Discussion
Conclusion/ Recommendations
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