Green Sustainable Process for Chemical and Environmental Engineering and Science: Sonochemical Organic Synthesis

Cover
GREEN SUSTAINABLE
PROCESS FOR
CHEMICAL AND
ENVIRONMENTAL
ENGINEERING AND
SCIENCE
Sonochemical Organic
Synthesis
Copyright
Contributors
Ultrasound-assisted organic synthesis
	Introduction
	Extrinsic variables affecting ultrasound irradiation
		Influence of solvent
		Influence of power
		Influence of frequency
		Influence of duty cycle
		Influence of temperature
	Origins of the chemical effects in sonochemistry
	Reactor design and configuration
		Ultrasonic cleaning bath
		``Cup-horn´´ sonicator
		Direct immersion ultrasonic horn
	Classification of US-assisted organic synthesis
		Homogeneous
			Aqueous
			Nonaqueous
		Heterogeneous
			Metal-organic frameworks
			Phase-transfer catalysis
			Heterogeneous catalysis
		Enzymatic catalysis
	Kinetics of sonochemical reactions
		Phase-transfer catalyzed reactions
		Homogeneously or heterogeneously catalyzed reactions
		Enzyme catalyzed reactions
	Industrial applications of US-assisted organic reactions
		Heterocyclic compounds
			Synthesis of pyrazoline derivatives
			Synthesis of 2-imidazolines
			Synthesis of vitamins
		Condensation reactions
			Synthesis of β-hydroxyl ketones
			Synthesis of ketoximes
			Synthesis of 4-oxo-2-thioxohexahydropyrimidines
		Substitution reactions
			Reaction of carboxylic acids to Merrifield resin
			Synthesis of functionalized arylacetylenes
		Reduction reactions
			Synthesis of fluorinated alkanes and cycloalkanes
			Hydrogenation of ketones
		Addition reactions
			Synthesis of mandelic acid
		Photochemical reactions
			Synthesis and photochemistry of 1-iodocyclohexene
		Protection/deprotection
			Protection of alcohols
		Coupling reactions
			Synthesis of propargylamines
			Synthesis of Z and E stilbenes
		Oxidation reactions
			Oxidation of alkylarenes to the corresponding acids
		Polymerization reactions
			Synthesis siloxane monomers
		Alkylation and acylation reactions
			Synthesis of N-alkoxyphthalimides
	Conclusion and future aspects
	References
Sonochemical protocol for catalyst-free organic synthesis
	Introduction
	Acoustic cavitation
	Equipment requirement for sonochemical reactions in laboratory
		The ultrasonic cleaning bathtub
		Ultrasonic horn system
	Application of ultrasound in catalyst-free organic synthesis
		Catalyst-free sonochemical synthesis of heterocyclic organic scaffolds
			Synthesis of pyrazole-based heterocycles
			Synthesis of quinoline-based heterocycles
			Synthesis of pyrimidine-based heterocycles
			Synthesis of spiro-based heterocycles
			Synthesis of bioactive organic compounds bearing nitrile functionality
			Synthesis of rhodanines
			Synthesis of 4H-3,1-benzoxazin-4-ones
			Synthesis of quinazolines-based heterocycles
			Synthesis of pyrido[2,3-c] coumarins
			Synthesis of octahydroxanthenes
			Synthesis of pseudopeptides containing rhodanine
			Synthesis of derivatives of quinoxaline
			Synthesis of 2H-indazolo[2,1-b]phthalazine-triones
			Synthesis of 1-(2-fluorophenyl)-1,4-dihydropyridines
		Applications of ultrasound in catalyst-free synthesis of molecules other than heterocycles
			Synthesis of α-amino phosphonates
			Synthesis of ferrocenyl containing carbonyl compounds
			Synthesis of propanamides
			Synthesis of dithiocarbamates
			Synthesis of thiourea
			Synthesis of ketene imines
			Synthesis of series of formamidines
			Synthesis of N-benzyl-N-(4-chlorophenyl)cyanamide
			Synthesis of α-sulfamidophosphonate
	Conclusion
	References
Sonochemical protocol for stereoselective organic synthesis
	Introduction
	Stereoselective organic synthesis under ultrasonication
	Conclusion
	References
Sonochemical protocol for alkylation reactions
	Introduction
	Alkylation reaction
	Alkylation reaction under sonication
		C-Alkylation reaction
		O-Alkylation reaction
		N-Alkylation reaction
		S-Alkylation reaction
	Conclusions
	References
Sonochemical protocol for solvent-free organic synthesis
	Introduction
		Ultrasound classification and its applications
		Sonochemistry and its merits
		Origin of the sonochemical effect
		Sonochemical device
		Ultrasound-assisted solvent-free organic synthesis
		Aim and scope of this review
	Ultrasound-promoted catalyst-free organic synthesis under solvent-free conditions
		Synthesis of N,N-dialkyl- and N,N-diaryl-1,4-diazabutadienes
		Diastereoselective sequential one-pot double aza-Michael preparation of pyrrolidines
		Three-component one-pot prepartion of α-sulfamidophosphonate derivatives
		One-pot creation of α-aminophosphonate frameworks
		Preparation of N,N-diarylfunctionalized formamidines
		Synthesis of substituted pyrazolone derivatives
		Development of 1,4-dihydropyridine scaffolds
		Preparation of 8-aryl-7,8-dihydro-[1,3]-dioxolo[4,5-g]quinolin-6 (5H)-ones
		t-Butoxycarbonyl-mediated protection of aromatic and aliphatic amine derivatives
		N-Formylation of aromatic amine derivatives
		Protecting alcohol moieties through formation of silyl ethers
	Ultrasound-assisted catalytic organic synthesis under solvent-free conditions
		Amino grafted zeolite-catalyzed synthesis of trans-chalcones
		Acid-clay-catalyzed synthesis of synthesis of trans-chalcones
		Zirconyl chloride-catalyzed preparation of 3,4-dihydro-2(1H)-quinolinones
		Sodium bisulfite-catalyzed preparation of pyrano[2,3-c]pyrazole derivatives
		Dendrimer-PWAn nanoparticles-catalyzed synthesis of multi-substituted imidazoles
		Nano SiO2-catalyzed synthesis of 3,3-(methylene)bis(coumarins)
		MgFe2O4 nano-catalyzed synthesis of coumarins
		Poly(4-vinylpyridinium) perchlorate-catalyzed synthesis of coumarins
		P2O5-SiO2-catalyzed formation of 1-substituted 1H-1,2,3,4-tetrazoles
		o-Phthalimide-N-sulfonic acid-catalyzed formation of alkenyl-2,2-butylidene-1,3-dioxane-4,6-dione derivatives
		p-Toluenesulfonic acid (PTSA)-catalyzed preparation of β-indolylketones
		Gallium(III) triflate-catalyzed [4+2+1] formation of 3,4-difunctionalized-1,5-benzodiazepines
		Magnesium oxide-catalyzed synthesis of α-oxycarbanilinophosphonates
		Antimony(III) chloride-catalyzed synthesis of dihydropyrimidinones
		Potassium thiocyanate/iodine-catalyzed formation of (Z)-β-iodo vinylthiocyanate derivatives
		Monopotassium phosphate-catalyzed preparation of α-hydroxyphosphonate derivatives
		Sodium hexanesulfonate-catalyzed formation of α-aminophosphonates
		Sulfur/morpholine-catalyzed synthesis of 2-aminothiophenes
	Conclusion
	References
Sonochemical protocol for biocatalysis
	Introduction
		Biocatalysis
		Ultrasonication
	Sono-biomechanics of enzymatic reactions
		Biomechanics of enzymes in ultrasound
		Cavitational bubble dynamics
	Ultrasound-assisted enzyme-catalyzed reactions
		Free enzyme catalysis
		Immobilized enzyme catalysis
		Whole-cell biocatalysis
	Factors affecting ultrasound-assisted enzyme-catalyzed reactions
		Influence of frequency
		Influence of intensity/power
		Influence of pH and temperature
		Influence of duty cycle
	Effect of reactors on enzyme-catalyzed reactions in sonication
		Ultrasonic horn
		Ultrasonic bath
		Ultrasound-assisted packed bed reactor (PBR)
		Scale-up
	Kinetics and thermodynamics of sono-enzymatic synthesis
		Effect of ultrasound on kinetics parameters
		Effect of ultrasound on thermodynamic parameters
	An ideal sonochemical protocol for biocatalysis
		Selection of reactor vessel
		The medium
		Mapping
		Bath type
		Placement of reactor
		Enzyme form
		Temperature control
		Monitoring enzyme activity concerning time
	Conclusion and future prospects
	References
Sonochemical protocol for coupling reactions
	Introduction and background
	Sonochemical coupling reactions
		Sonochemical protocol in CC coupling reactions
			Reductive coupling to carbonyl (>CO) functionality under ultrasonic irradiation
			Sonochemical CC coupling in the presence of Li species
			Sonochemical CC coupling in the presence of Pd species
				Sonochemical Heck coupling
				Sonochemical Suzuki coupling
				Sonochemical Sonogashira coupling
				Sonochemical Stille coupling
			Sonochemical CC coupling in the presence of metal species other than Pd
		Sonochemical protocol in CN coupling reactions
		Sonochemical protocol in CSn coupling reactions
	Concluding remark
	References
Sonochemical protocol for protection and deprotection of functional groups in organic synthesis
	Introduction
	Different energy source for chemical reaction
	Mechanisms for the generation of energy in sonication
	Brief discussion on protection and deprotection of functional groups
		Protecting groups for hydroxy
		Protecting groups for aldehydes and ketones
		Protecting groups carboxylic acids/amines
	Ultrasound-promoted protection and deprotection of hydroxy group (OH) in carbohydrates
		Acetylation and ketal protection
		Deprotection of acetate, trityl, and benzylidene functionalities
		Migration of functional groups
		Ultrasound-assisted selective deprotection of terminal acetonides
		Sugar O-tosyl groups deprotection from purine nucleosides
	Ultrasound-promoted protection and deprotection of hydroxy group (OH) in noncarbohydrates
		Ultrasound mediated catalyst-free protection of alcohols
		O-Silylation of homoallyloxyalcohols
		Deprotection of silyl ether
		Acetylation
		PMB/MOM protection
		Deprotection of DMT (dimethoxytrityl)
		Cleavage of phenol protected functionality
	Deprotection of carbonyl protecting groups
		Removal of acetals and ketals
		Deprotection of aldehyde by deoximation of oximes
		Rapid oxidative cleavage of oximes
		Silica sulfuric acid-catalyzed deprotection of oximes
		Chemoselective 1,1-diacetate protection
		Deprotection of 1,1-diacetates
	Protection and deprotection of amine group
		Ultrasound and heterogeneous catalyst promoted acylation of amines
		N-Boc protection of amines
		N-Fmoc protection of amines
		Ultrasound-assisted amine protection as β-enamino esters
		N-Acylation of sulfonamides
		Deprotection of substituted phenyl sulfonyl carbamates
		Deprotection of propargyloxycarbonyl (POC) [65, 66]
	Carboxylic acid group protection/deprotection
		Esterification of COOH in amino acids
		Ester hydrolysis in the presence of sonication
	Summary
	References
Sonochemical protocols for Grignard reactions
	Introduction
	Grignard sonochemistry
		Ultrasound-assisted preparation of Grignard reagents
		Reactions of Grignard reagents under ultrasound irradiation
			Reaction of Grignard reagents with aldehydes
			Reaction of Grignard reagents with ketones
			Reaction of Grignard reagents with acetals
			Reaction of Grignard reagents with esters
	Concluding remarks
	References
Sonochemical approach for the synthesis of organo-modified layered double hydroxides and their applications
	Introduction
	A summary on the ultrasonic approach
		Transducers configuration
		Mechanism
	Synthesis of organo-modified/LDHs and their nanocomposites with prospect applications
		Carbon derivative/LDH structures
		Drug/LDH structures
		Polymer/LDH structures
		Other organics/LDH structures
	Comparison of ultrasonication with other techniques
	Some disadvantages of sonochemistry
	Other applications of ultrasound
	Conclusions
	References
Sonochemical protocol for the organo-synthesis of TiO2 and its hybrids: Properties and applications
	Introduction
	Effect of ultrasonic power in the organic synthesis of TiO2 and their applications
	Effect of ultrasonic power in the organo-modification of TiO2 and their applications
		Silane coupling agents
		Dicarboxylic acid
		Polymers
		Other modifiers
	Sonochemical synthesis of polymeric hybrids based on TiO2 and their applications
		Remediation industry
		Packaging industry
		Other NCs and their applications
	Preparation of carbon nanomaterials/TiO2 hybrids using ultrasonication
		Graphene or graphene oxide/TiO2 hybrids
		Carbon nanotubes (CNTs)/TiO2 hybrids
	Conclusions and future prospects
	References
Sonochemical protocol of polymer synthesis
	Emulsion polymerization
		Ultrasound-assisted mini-emulsion polymerization system
		Ultrasonic initiation of aliphatic alcohols polymerization
		Liquid carbon dioxide systems
		Indirect ultrasound-assisted emulsion polymerization
		Ultrasound-assisted emulsion polymerization to produce hydrogel polymer
		Ultrasound-assisted emulsion copolymerization of butyl acrylate/vinyl acetate
		Ultrasound-assisted graft copolymerization of acrylic acid/poly(vinylidene fluoride)
		Ultrasonic-assisted emulsion polymerization of polyaniline/nanostructure TiO2 nanocomposites
		Ultrasound-assisted emulsion polymerization ZnO/poly(butyl methacrylate) nanocomposites
		Ultrasound-assisted emulsion polymerization of the poly (styrene-co-methyl methacrylate)/montmorillonite nanocomposite
		Ultrasound-assisted mini-emulsion production of polypyrrole-ZnO (PPy/ZnO)
	Bulk and suspension polymerization
		Ultrasound-assisted bulk polymerization of styrene
		Ultrasound-assisted bulk polymerization to fabrication of hydrogel macromolecules
		Ultrasound-assisted suspension polymerization of styrene
		Ultrasound-assisted suspension polymerization of 2-hydroxyethylmethacrylate/ethylene glycol dimethacrylate copolymer
	Solution polymerization
		Ultrasound-assisted polymerization of acrylic hydrogels
		Ultrasound-assisted copolymerization of polyacrylamide/nano-fibrillated cellulose and acrylic acid/poly (vinylidene  ...
		Ultrasound-assisted polymerization of poly (N-isopropylacrylamide-co-2-hydroxyethyl methacrylate)
	Phase-transfer catalysis polymerization
		Ultrasound-assisted polymerization of butyl acrylate using crown ethers as PTC
		Ultrasonic-assisted free radical polymerization of ethyl methacrylate using PTC
		Ultrasound-assisted radical polymerization of acrylonitrile using PTC
		Ultrasound-assisted radical polymerization of acrylonitrile using PTC
	Reversible addition-fragmentation chain transfer
		Ultrasound-assisted graft modification of silica gel by RAFT polymerization
		Ultrasound-assisted RAFT polymerization-induced self-assembly (Sono-RAFT-PISA)
		Ultrasound-assisted Sono-RAFT polymerization in organic solvents
	Atom transfer radical polymerization
		Ultrasound-assisted polymerization of acrylate by (ATRP) method
		Ultrasound-assisted polymerization of acrylate by (ATRP) method
	Ring-opening polymerization
	Conclusion
	References
Sonochemical methods and their leading properties for chemical synthesis
	Introduction
	Ultrasound operation and bubble formation
	Effectiveness and parameters of the sonochemical process
	Intensives and frequencies of sonochemical irritations
	Duration of stirring
	Heterogeneous and homogenous features of reactions under ultrasonic conditions
	Conversion of biomass to biofuels under ultrasonic conditions
	Features of sonochemical reactors and devices used for sonochemical synthesis
	Conclusions
	References
Index
Back Cover