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TITLE
DEDICATION
CERTIFICATE
DECLARATION
ACKNOWLEDGEMENT
CONTENTS
I. INTRODUCTION AND OBJECTIVES
INTRODUCTION
OBJECTIVES OF THE PRESENT WORK
II. BENZIL-BENZILIC ACID REARRANGEMENT IN CROSSLINKED MACROMOLECULAR SYSTEMS
RESULTS AND DISCUSSION
1. (a) Divinylbenzene-Crosslinked Polystyrene
(b) Tetraethyleneglycol Diacrylate-Cross-linked Polystyrene
2. Chloromethylation of Polystyrene
3. Synthesis of Polymeric Aldehydes
4. Preparation and Characterization of Polymeric Analogues of α-Hydroxy Ketones
(a) Intrapolymeric Benzoin Condensation
Fig.II.1. IR spectram of polymeric benzoin
Fig.II.2. c13CP/MAS spectrum of polymeric benzoin
(b) Crossed Benzoin Condensation Between Pol.ymeric Aldehyde (4a or 4b) and Substituted Benzaldehydes
(c) Effect of Crosslinking on Polymeric Benzoin Condensation
(d) Effect of Hyperentropic Factor on Intrapolymeric Benzoin Condensation
Fig. II.3. Effect of hyperentropic factor on intrapolymeric benzoin condensation
5. Synthesis of Polymeric Diketones
Fig.II.4. IR spectrum of polymeric benzil analogue
Fig.II.5. C13 CP/MAS NMR spectrum of polymeric benzil
6. Benzil-Benzilic Acid Rearrangement in Crosslinked Polystyrene Networks
Fig.II.6. IR spectrum of polymeric benzilic acid
Fig.II.7. C13 CP/MAS NMR spectrum of polymeric benzilic acid
(a) Effect of Substituents
(b) Effect of the Nature of Crosslinking
(c) Effect of the Degree of Crosslinking
(d) Effect of Solvation
Fig. II.8. Effect of solvation on the extent of benzil-benzilic acid rearrangement in DVB crosslinked polystyrene matrix
Fig. II.9- Effect of solvation on the extent of benzil-benzilic acid rearrangement in TTEGDA- crosslinked polystyrene matrix
7. Kinetics of Benzil-Benzilic Acid Rearrangement in Polymeric Matrices
8. Investigation of Salt Effect
Fig. II.10- Salt effect on benzil-benzilic acid rearrangement in polymeric matrices
9. Molecular Rearrangements in Macromolecular Solutions
(a) Synthesis of Polybenzoin
Fig.II.11. Proton NMR spectrum of polybenzoin
(b) Synthesis of Polybenzil
(c) Synthesis of Benzilic Acid (10) from Polybenzil: Benzil-Benzilic Acid Rearrangement
Fig.II.12. Proton NMR spectrum of polybenzoil
Fig.II.13. Proton NMR spectrum of polybenzilic acid
III. MOLECULAR REARRANGEMENT IN MACROMOLECULAR CAVITIES
RESULTS AND DISCUSSION
1. Benzil-Benzilic Acid Rearrangement in Soluble Macromolecular Cavities
(a) Benzil-Benzilic Acid Rearrangement in PEG-400 and PEG-6000 Media
Fig. III.1. Concentration of PEG Vs rate constant
Fig. III.2. Concentration of PEG Vs rate constant
(b) Model Reaction I: Hydrolysis of Ethyl Acetate in PEG-6000 Medium
Fig. III.3- Kinetics of the hydrolysis of ethyl acetatein PEG-6000 medium
(c) Model Reaction II: Saponification of ester in PEG-6000 Medium
2. Encapsulation of 1, 2-Diketo Systems in the Cavities of Crosslinked Polymeric Networks and its Rearrangement to α-Hydroxy Acids
(a) Encapsulation of Benzil Molecules in the Cavities of DVB- Crosslinked Polystyrene Networks
Fig.III.4. IR spectra of: I-PS-DVB copolymer, II-benzil encapsulated PS DVB co-polymer
Fig. III.5. Scanning electron micrographs of PS-DVB resin
Fig. III.6. Scanning electron micrograph of benzil-encapsulated PS-DVB resin
(b) Encapsulation of α -Diketone in the Cavities of BDDMA-Crosslinked Polystyrene
Fig.III.7. IR spectra of -PS-BDDMA resin, II - benzil encapsulated PS-BDDMA resin
Fig. III.8. Scanning electron micrograph of PS-BDDMA resin
Fig. III.9. Scanning electron micrograph of benzil encapsulated PS-BDDMA resin
(c) Encapsulation of α-Diketones in the Cavities of EGDMA-Crosslinked Polystyrene
Fig.III.10. IR spectra of I - PS-EGDMA resin, II - benzil encapsulated PS-EGDMA resin
(d) Benzil-Benzilic Acid Rearrangement in the cavities of DVB- Crosslinked Polystyrene Networks
Fig. III.11. IR spectrum of benzilic acid encapsulated PS-DVB resin
Fig. III.12. Scanning electron micrograph of benzilic acid- encapsulated PS-DVB resin
(e) Benzil-Benzilic Acid Rearrangement in the cavities of BDDMA- Crosslinked Polystyrene Matrix
(f) Benzil-Benzilic Acid Rearrangement in the cavities of EGDMA- Crosslinked Polystyrene Matrix
IV. HOFMANN REARRANGEMENT IN CROSSLINKED POLYMERIC MATRICES
RESULTS AND DISCUSSION
1. Preparation of Polymeric Amide from DVB-Crosslinked Polystyrene
2. Synthesis of Polymeric Amine from Polymeric Amide by Hofmann Rearrangement
3. Rearrangement / Hydrolysis: Effect of Temperature
Fig. IV.1. IR spectra of: I -polymeric amide II -polymeric amine
Fig. IV.2. Rearrangement Vs hydrolysis
4. Synthesis of Crosslinked Polyacrylamide Resins
(a) Synthesis of DVB-Crosslinked Polyacrylamide
(b) TTEGDA-Crosslinked Polyacrylamide
(c) Preparation of NNMBA-Crosslinked Polyacrylamide
5. Hofmann Rearrangement in Crosslinked Polyacrylamide Matrices
(a) Hofmann Rearrangement in DVB- Crosslinked Polyacrylamide Matrices
(b) Hofmann Rearrangement in TTEGDA- Crosslinked Polyacrylamide Matrix
(c) Hoffman Rearrangement in NNMBA- Crosslinked Polyacrylamide Matrix
V. EXPERIMENTAL
1. General
2. Synthesis of Styrene-DVB Copolymer: General Procedure
3. Synthesis of Styrene-TTEGDA Copolymer: General Procedure
4. Chloromethylation of Styrene-Based Copolymers: General Procedure
5. Estimation of Chlorine in Chloromethyl Polystyrene
6. Preparation of Polymer-Bound Benzaldehyde
7. Determination of -CHO Capacity
8. Synthesis of Polymeric Benzoin
(a) Intrapolymeric Benzoin Condensation: General Procedure
(b) Crossed Benzoin Condensation: General Procedure
9. Determination of Hydroxyl Capacity of Benzoin
10. Synthesis of Polymeric Benzil
11. Benzil-Benzilic Acid Rearrangement in Crosslinked Polymeric Matrices: General Procedure
12. Estimation of Carboxyl Value of Benzilic Acid
13. Investigation of the Effect of Solvents on Polymer-Analogous Benzil-Benzilic Acid Rearrangement
14. Synthesis of Polybenzoin from Terephthalaldehyde
15. Synthesis of Polybenzil from Polybenzoin
16. Synthesis of α -Hydroxy Acid from Polybenzil: Benzil-Benzilic Acid Rearrangement
17. Benzil-Benzilic Acid Rearrangement in PEG400 Medium: General Procedure
18. Benzil-Benzilic Acid Rearrangement in PEG6000 Medium: General Procedure
19. Preparation of Benzil Encapsulated Styrene-Divinylbenzene Copolymers: General Procedure
20. Preparation of Benzil-Encapsulated Styrene-BDDMA Copolymers: General Procedure
21. Preparation of Benzil-Encapsulated Styrene-EGDMA Copolymers: General Procedure
22. Benzil-Benzilic Acid Rearrangement in the Cavities of Styrene-Based Copolymers
23. Preparation of Polymeric Benzoic Acid
24. Preparation of Polymeric Benzoyl Chloride
25. Preparation of Polymeric Benzamide
26. Hofmann Rearrangement in Crosslinked Polymeric Matrices: Preparation of Polymeric Amine
27. Temperature Dependence of Polymer-Analogous Hofmann Rearrangement: General Procedure
28. Determination of Amino Capacity of the Amino Resin: General Procedure
29. Estimation of Carboxyl Capacity of the Rearrangement Product
30. Preparation of Polyacrylamides Crosslinked with DVB: General Procedure
31. Preparation of Polyacrylamides Crosslinked with TTEGDA: General Procedure
32. Preparation of Polyacrylamides Crosslinked with NNMBA: General Procedure
33. Hofmann Rearrangement of Polyacrylamides into Polymeric Amines
VI. CONCLUSION AND OUTLOOK
REFERENCES