Experimental Chemistry Lab Course

CHEM 100
Experiment 6

Basit Yameen (PhD)

Associate Professor
Department of Chemistry and Chemical Engineering
SBASSE, LUMS

1
 Experiment 6: Polymers as foundation of life, current modern world, and future technological
evolution: A hands on experience of Nylon synthesis and characterization – A case of interfacial
polymerization

Polymers are large molecules consisting of a long chain or chains of atoms covalently bonded together (Natural and Synthetic).
Monomers are the small molecules used to synthesize the larger polymeric chain.
Spider web/silk

Oak logs and grass have in common the natural

polymer cellulose. The monomer is glucose.
Hemoglobin

Cellulose (polysaccharide
or polycarbohydrate )

Deoxyribonucleic acid (DNA) is a polynucleotide

Proteins are polypeptides

Wood, wool, cotton, starch, natural rubber, skin, and hair are natural polymers. Natural polymers exhibit a stunning variety of properties. They give
strength to an oak tree, delicacy to a spider’s web, and flexibility to a blade of grass. 2
 (Repeat Unit)
Polypeptide
Proteins are polypeptides.
(Bio)macromolecules

3
Synthetic Polymers
Polymers are large molecules consisting of a long chain or chains of atoms covalently bonded together.
Monomers are the small molecules used to synthesize the larger polymeric chain.

Synthetic polymers

Polyethylene Polypropylene Polyvinylchloride Polystyrene

Thermoplastic polymer

Polyester
Polyethylene terephthalate (PET) Polyamide (Nylon 6,6) Polyurethane

Thermoset polymers

4
 Synthetic polymers

Polymers Addition polymers

Polyethylene Polypropylene Polyvinylchloride Polystyrene

Addition / Chain Growth

Polymerization

Monomers

Ethylene Propylene Vinylchloride

Styrene

Polymers Condensation polymers

Polyester
Polyethylene terephthalate (PET) Polyamide (Nylon 6,6) Polyurethane
Condensation / Step Growth
-H2O -H2O Polymerization

Monomers

Terephthalic acid Ethylene glycol 1,4-Phenylene diisocyanate Ethylene glycol

Hexane-1,6-diamine Adipic acid
5
 Some Applications of Polymers

Targeted Drug Delivery Systems Drug eluting stent

polylactide (PLA) Polycaprolactone (PCL)

Lithium polymer batteries Fuel cell technologies Printable solar cells Flexible electronics Water filtration – membranes and cartridges

6
 Polymerization
Synthetic polymers

Polymers Addition polymers

Polyethylene Polypropylene Polyvinylchloride Polystyrene

Addition / Chain Growth Polymerization

Monomers

Ethylene Propylene Vinylchloride

Styrene Condensation / Step Growth Polymerization

Polymers Condensation polymers

Polyester
Polyethylene terephthalate (PET) Polyamide (Nylon 6,6) Polyurethane

-H2O -H2O

Monomers

Terephthalic acid Ethylene glycol 1,4-Phenylene diisocyanate Ethylene glycol

Hexane-1,6-diamine Adipic acid
7
Interfacial Polymerization
Collapsed polymer film

Polyamide (Nylon 6,6) Hexane solution of adipoyl chloride

Polymer film forming at the interface

-HCl Water solution of hexane-1,6-diamine
and NaOH

1,6-Hexanediamine Adipoyl Chloride

+ NaOH
Water (phase) d: 0.997 g/mL Hexane (phase) d: 0.661 g/mL
8
Interfacial Polymerization

Description of Process

1. Polymerization of two reactants is carried out at the interface between two liquid phases, each containing
one of the reactants. Polyamidation is performed at room temperature by placing an organic solution of the
acid chloride on top of an aqueous phase containing the diamine.
2. The reactants diffuse to and undergo polymerization at the interface.
3. The polymer product precipitates and is continuously withdrawn in the form of a continuous film or
filament if it has sufficient mechanical strength.
4. Mechanically weak polymers that cannot be removed impede the transport of reactants to the reaction site
and the polymerization rate decreases with time.
5. An inorganic base must be present in the aqueous phase to neutralize the by-product hydrogen chloride
(HCl). If it were not neutralized the hydrogen chloride would tie up the diamine as its unreactive amine
hydrochloride salt leading to greatly lowered reaction rates.

9
Interfacial Polymerization

Procedure
1. Prepare a solution of 0.56 M NaOH (from a 2M solution).
2. Dissolve 0.36 g (3.06 mmoles) of 1,6-hexanediamine in the previously prepared 5.7 mL
of 0.56 M aqueous NaOH solution.
3. Dissolve 0.5 mL of adipoyl chloride (density 1.25 g/mL, 3.41 mmoles) in 5.7 mL of
hexane.
4. Carefully add the hexane solution of adipoly chloride on top of the aqueous diamine
solution. Do NOT shake, swirl, or stir the two-phase mixture. The polymerization will
occur at the interface between the two immiscible layers.
5. Take a pair of forceps or a tong, and carefully pull out the nylon from the boundary
between the two phases.
6. Pull this up and wrap this nylon strand on a glass rod or a spatula.
7. Wash and dry the obtained nylon and record its FTIR spectrum.

11
 Expected results
IR Spectrum

Stretching Bending
vibrations vibration

N-H
stretching
vibration
Symmetric stretch
~2850 cm-1

Asymmetric stretch
~2930 cm-1

11
12
CHEM 100 – Experimental Chemistry

13
 CHEM 100 Team - Instructors

Dr. Basit Yameen Dr. Habib ur Rehman

Associate Professor Associate Professor
PhD: Max Planck Institute for PhD: Institute for New Materials,
Polymer Research, Germany Germany

Experiments 1, 4, 5, & 6 Experiments 2 & 3

Department of Chemistry & Chemical Engineering

14
CHEM 100/101 Team – Permanent Staff and Student TAs

Syed Zajif Hussain

Amina Asghar Hamayal Shahzad Muhammad Zain
Senior Scientific Officer
Lab Instructor Lab Instructor Lab Instructor
 CHEM 100/101 Team – Permanent Staff and Student TAs

Kiran Khaqan Adeeba Parveen Zainab Jawad Khan Badar Uz Zaman Rimsha Shafiq Amina Bhatti Arooba Rahat Esha Saeed Daim Sajid
BS Chemistry BS Chemistry BS Chemistry MS Chemistry BS Chemistry MS Chemistry MS Chemistry BS Chemisrty BS Chemistry

Nida Fatima Hannia Khalid Abdul Waseh Irfan Ullah Sheeza Fatima Fatima Moor Rida Arshad Abu Sufyan Faseeh Akbar
BS Chemistry MS Chemistry BS Chem Engg PhD Chemistry BS Chemistry MS Chemistry MS Chemistry MS Chemistry PhD Chemistry

Qurat ul Ain Maryam Naseer

MS Chemistry MS Chemistry
 Placements

Kiran Khaqan
BS Chemistry Esha Saeed Muhammad Zain
BS Chemisrty MS Chemistry

Hannia Khalid
MS Chemistry Fatima Moor
MS Chemistry
 Chemistry - PLACEMENTS after completing PhDs

Dr. Rimsha Mehmood Dr. Ahmed Yousaf Dr. Sikandar Abbas Dr. Warda Ejaz

Dr. Syed Ali Moeed Dr. Fiaz Ahmed Dr. Hamza Javed
Dr. Muhammad Affawn
2022 placement 2022 placement
18
 Chemistry - PLACEMENTS after completing PhDs

Software
company

Dr. Waqas Rasheed Dr. Abdul Malik Dr. Ghzanfar Ali

Dr. Assad Ullah Khan

Zain Yousaf Dr. Hassan Javed

Dr. Mohammad Ahmed Safeer Alvi
19
Chemical Engineering - PLACEMENTS
Chemical Engineering - PLACEMENTS
Innovations Through Chemicals, Materials and Transformations!

Panadol
(Paracetamol)

22
Innovations Through Chemicals, Materials and Transformations!

Gordon Moore
BS Chemistry
PhD Chemistry
Co-founder

23
 The Paradigm Shift

From
“atoms and molecules”
to
“everything that involves atoms and molecules”

24
“What is it that chemists do, anyway?”

“ Let me sketch a conversation I have had on various occasions—in

one form or another—at dinner parties and on airplanes.
The person next to me says, “What do you do?”
I answer “I am a Chemist”
S/he responds: “Chemistry was the one course in high school I
flunked.
What is it that chemists do, anyway?”

I have tried two types of answers.

One is: “Well, we make drugs. Like statins. Very useful. They are
inhibitors of a protein called HMGA-CoA reductase, and they help
to control cholesterol biosynthesis and limit cardiovascular
disease.” (This answer usually ends the conversation.)
The second is: “We change the way you live Prof. George Whitesides
and die.”
”
https://chemistry.harvard.edu/people/george-
whitesides
The second works better.
25
Wish you all the best and success!