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synopsis

INSTITUTE OF CHEMICAL TECHNOLOGY (University under Section -3 of the UGC Act 1956)

Maharashtra Govt’s Elite Status and Centre of Excellence Matunga, Mumbai – 400019

A SYNOPSIS OF THE THESIS TO BE SUBMITTED TO

THE INSTITUTE OF CHEMICAL TECHNOLOGY/UNIVERSITY OF MUMBAI

FOR THE DEGREE OF

DOCTOR OF PHILOSOPHY (SCIENCE) IN

CHEMISTRY

TITLE OF THESIS : Synthetic Reactions & Applications of Chemically Recycled Products from Polyester Waste

NAME OF CANDIDATE : Mr. Rikhil Vinodkumar Shah

NAME AND DESIGNATION : Prof. S. R. Shukla OF RESEARCH GUIDE Professor of Technology of Dyeing & Printing PLACE OF RESEARCH WORK : Dept. of Fibres & Textile Processing Technology Institute of Chemical Technology, Matunga, Mumbai-400019 DATE OF ADMISSION : 15th December, 2009 REGISTRATION NUMBER AND DATE : 11Chy4052, 21/09/2010 DATE OF SUBMISSION OF : 6th May, 2013

SYNOPSIS SIGNATURE OF RESEARCH GUIDE SIGNATURE OF CANDIDATE

(Prof. S. R. Shukla) (Rikhil V. Shah)

©Rikhil Shah, Institute of Chemical Technology (ICT), Mumbai, India

Introduction:

Ever since the first industrial scale production of synthetic polymers took place in

the 1940s, their production, consumption and waste generation rate of the plastic solid

waste has considerably increased.

Poly (ethylene terephthalate) (PET) is one of the versatile engineering plastics

showing excellent thermal and mechanical properties. It is non-toxic, semi-crystalline,

thermoplastic polyester with high strength and crystal clear transparency. Although its

main application is in the apparel sector, large quantities are also consumed in the

manufacture of X-ray films and food packaging, especially in production of soft-drink

bottles. The post-consumer PET product waste does not create a direct hazard; however,

its substantial volume fraction in solid waste streams coupled with its high resistance to

the atmospheric and biological degradation is the main threat to the environment.1 Since

it is not appropriate to dispose off waste PET on land-fill sites, alternative methods of

recycling, including physical and chemical ones, have been developed.

Chemical recycling appears to be the only alternative that is sustainable.2 PET

possesses ester groups, which can be cleaved by some reagents, such as water

(hydrolysis), 3, 4 alcohols (alcoholysis), 1, 3 glycols (glycolysis), 5, 6 and amines

(aminolysis). 7, 8 Great attention has been paid to chemical recycling of PET waste

leading to recovery of the monomeric products that can be further used in the synthesis of

chemicals or intermediates of interest. 9

In the present work, PET soft drink bottle waste was depolymerized using

different routes and the products obtained were subjected to various chemical reactions to

get useful chemicals.


The work done is summarized as follows:

1. Phase transfer catalyzed alkaline hydrolysis of PET Waste

Reaction parameters: PET Waste (1mol); Aq. NaOH (3 mol); TBAB (3% w/w); Time (3h);

Temp (80°C).

Poly(ethylene terephthalate) (PET) waste bottle flakes were hydrolyzed under

atmospheric pressure by aqueous solution of NaOH at temperature below 80°C using

phase transfer catalyst (PTC). Hydrolysis of PET bottle waste was carried out having

particle size >6mm using tetra butyl ammonium bromide (TBAB) as PTC and non polar

solvents like 1,4-dioxane, xylene, etc. have been used to accelerate the rate of reaction.

One of the monomers terephthalic acid (TPA) has been produced with excellent yield (88

%) using PTC in alkaline hydrolysis of PET waste. The reaction conditions were mild as

compared to those reported in the literature.

a. Aminolysis of PET Waste

b. Using N-(2-aminoethyl) ethanolamine3

O

O O

O CH2

H2C

PET Waste

n

H2N

HN

OH O

NH

HN

HO

O

HN

NH

OHCatalystRef lux

BHAETA

Reaction parameters: PET Waste (1mol); AEEA (4 mol); Catalyst (0.5% w/w); Time (4h)


The aminolysis of PET bottle waste was successfully carried out under atmospheric

pressure in the excess of N-(2-Aminoethyl) ethanolamine (AEEA). The aminolysis with

1:4 PET: amine ratio, 0.5% w/w sodium acetate catalyst under reflux for 5 h gave pure

bis (-(2-hydroxyethyl amino) ethyl) terephthalamide (BHAETA) with about 72 % yield.

It has application as chain extender in polyurethane industry.

c. Using propanol amines

Reaction parameters: PET Waste (1mol); Amine (5 mol); Catalyst (0.5% w/w); Time (5h)

Aminolytic depolymerization of post consumer poly (ethylene terephthalate) (PET)

bottle waste with 2-amino-2-methyl-1-propanol, 1-amino-2-propanol and 3-amino-1-

propanol under atmospheric condition was investigated in the presence of sodium acetate

O

O

O

O

n

PET Waste

O

NH

OH

O

HNHO

O

NH

OH

O

HN

OH

O

NH

OH

O

HN

HO

BHPTA BHIPTA BHAMPTA

HONH2 HO

NH2

HO NH2

3-amino-1-propanol 1-amino-2-propanol2-amino-2-methyl-1-propanol


as catalyst. The virtual products obtained in pure form were respectively bis (1-hydroxy-

2-methylpropan-2-yl) terephthalamide (BHMPTA), bis (2- hydroxypropyl)

terephthalamide (BHIPTA) and bis-(3-hydroxy propyl) terephthalamide (BHPTA). The

products BHIPTA (82%) and BHPTA (80%) were obtained in pure forms with good

yields with reaction time of 5 h.

d. Application of microwave irradiation for aminolytic depolymerization

Microwave heating was studied for aminolytic depolymerization of PET waste using

1-amino-2-propanol and 3-amino-1-propanol. The same optimized reaction parameters of

conventional heating were used by varying time of reaction up to 9 min. Decrease in the

time of reaction from 5 h to 7 min was achieved on using microwave irradiation as a

heating source with yields comparable to the conventional method.

e. Synthesis of bis-oxazoline and bis-oxazine

Bis-oxazolines and bis-oxazines have been used as chain extenders and cross-linkers in

polymers. BHIPTA and BHPTA were subjected to cyclization at ambient temperature

condition to obtain respectively 1,4-bis (5-methyl-4,5-dihydrooxazol-2-yl) benzene

(PBIOXA) and 1, 4-bis (5, 6-dihydro-4H-1, 3-oxazin-2-yl) benzene (PBOXA). Thus it is

possible to synthesize useful chemicals from PET waste


O

O

O

O

n

PET Waste

O

NH

OH

O

HNHO

O

NH

OH

O

HN

OH

BHPTA BHIPTA

HONH2HO NH2

3-amino-1-propanol 1-amino-2-propanol

N

O O

N N

O O

N

PBOXAPBIOXA

SOCl2 SOCl2

Reaction parameters: BHPTA (1mol); SOCl2 (4 mol); Time (16 h); Temp (27°C)

2. Synthesis of heterocyclic derivatives from PET waste and evaluation of their

antibacterial activity

The literature shows that compounds bearing 1,3,4-oxadiazole/thiadiazole and 1,2,4-

triazole derivatives possess wide variety of biological activitiy. The present study deals

with the prearation of terephthalic dihydrazide (TPHD) from PET waste via aminolysis

using hydrazine hydrate. The TPHD was further subjected to chemical reactions to obtain

various heterocycles. All synthesized compounds were characterized and evaluated for

the anti bacterial activity. Activity of each compound was compared with ciprofloxacin


and sulphametoxazol and found to show moderate activity as compared to these

standards.

O

O

HN NH2

NHH2N

Ar

N

C

X

O

HN

NH

X

NH

Ar

O

NH

HN

X

NH

Ar

NN

X X

NN

NH

NH

ArAr

NN

N N

NN

HXXH

Ar Ar

TPHD

Conc.H2SO4 2N NaOH

Ethanol/ 3 h

2(a-d) 3(a-d)

3. Acidic ionic liquid catalyzed synthesis of 2-oxazolines from β-hydroxyamides

2-oxazolines are widely found in natural products with a different range of biological

activities in catalysis and as synthetic intermediates. Also bis-oxazolines and different

chiral oxazolines have been widely used as auxillaries and ligands in asymmetric

synthesis. We have developed novel acidic ionic liquid and used for synthesis of 2-

oxazolines from β-hydroxyamides. The products were obtained in good yields for variety


of substrates. Efficient reaction protocol was developed and ionic liquid was recyclable

up to 3 cycles.

R NH

O

R N

O[SO3H-pBIM][HSO4]

90 oC

1a-i, R = Ar' 3a-i, R = Ar'

OH

Reaction parameters: β-hydroxy amide (2 mmol); IL (1 ml); Time (3h); Temp (90°C)

4. Phosphine free copper oxide catalyzed sonogashira coupling reaction

I H+CuO/ Ethanol amine

90οC

AryIodide Phenyl Acetylene Coupling productWithout any additivephoshane free

Reaction parameters: Aryl Iodide (1.2 mmol); Phenyl Acetylene (1 mmol); CuO (15% w/w);

Ethanol Amine (2 ml); Time (5h); Temp (90°C)

A new, efficient and inexpensive system has been developed to catalyze sonogashira

cross coupling reaction between aryl iodides and terminal alkynes. We have employed

CuO as catalyst using ethanolamine as ligand, base and solvent. The reaction conditions

were mild as compared to those reported in literature and products obtained were in good

to excellent yields.


References:

1. Karayannidis, G. P. ; Achilias, D. S. Macromol Mater Eng 2007, 292, 128.

2. Karayannidis, G. P. ; Achilias, D. S. Water, Air and Soil pollution :Focus 2004, 4, 385

3. Paszun, D.; Spychaj, T. Ind Eng Chem Res 1997, 36, 1373.

4. Kosmidis, V. A.; Achilias, D. S.; Karayannidis, G. P. Macromol Mater Eng 2001, 286,

640.

5. Shukla, S. R.; Kulkarni, K. S. J Appl Polym Sci 2002, 85, 1765.

6. Shukla, S. R.; Harad, A. M. J Appl Polym Sci 2005, 97, 513.

7. Shukla, S. R.; Harad, A. M. Polym Degrad Stab 2006, 91, 1850.

8. Soni, R. K.; Dutt, K.; Jain, A.; Soam, S.; Singh S. J Appl Polym Sci 2009, 113, 1090.

9. Shukla, S. R.; Palekar, V. P.; Pingale, N. D. Color Tech 2010, 126, 55.


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