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Synthesis of ionic liquid to
break oil-water emulsions
By
Hunny Kukdeja (17bch026)
Vikram Kataria (17bch058)
Contents
• Intro
• Properties
• RTILs
• Cons of ionic liquid
• Pros of ionic liquid
• Application of ionic liquid
• Emulsions
• Uses of emulsions
• Methods of emulsion breaking
• Experiments
• References
Ionic liquids
• Ionic liquids (ILs) are the
organic or may be
inorganic salts, generally
consisting of an organic
cations and a polyatomic
organic or inorganic
anions, that are in the
form of liquid phase
below 100°C.
Science of ionic liquid
• An ionic liquid is a salt in which the
ions are poorly coordinated, which
results in these solvents being
liquid below 100°C, or even at
room temperature (room
temperature ionic liquids, RTIL's).
At least one ion has a delocalized
charge and one component is
organic, which prevents the
formation of a stable crystal
lattice.
Glimpse on properties
Properties, such as melting point, viscosity, and
solubility of starting materials and other solvents, are
determined by the substituents on the organic
component and by the counterion. Many ionic liquids
have even been developed for specific synthetic
problems. For this reason, ionic liquids have been
termed "designer solvents".
RTILs
• One of the first RTILs was a mixture of
[emim]Cl with AlCl3 forming a series
of equilibria between [emim][AlCl4],
[emim][Al2Cl7], and [emim][Al3Cl10].
This RTIL is not water stable. The
discovery of water-insoluble RTILs
such as [bmim][PF6] allowed the
development of new work-up
methods, including the separation of
water-soluble by products by simple
extraction.
Pros of ionic liquid
• Absence of volatility
• Much lower toxicity as compared to lower boiling point solvents
• They can make safer microwave synthesis
• The dipole characteristics of ionic liquids translate into rapid
excitation by microwaves, and consequently faster reactions.
Cons of ionic liquid
• Ionic liquids have the potential to be green alternatives to
conventional organic solvents currently utilised by the
pharmaceutical industry. However, several factors still have
to be addressed before this new technology is
unconditionally welcomed by the pharmaceutical industry.
Issues encompassing cost, stability, toxicity, ease of
processing of pharmaceutical intermediate(s), and
advantages over conventional solvents
Applications of Ionic liquid
• Chemical processing in chemical reactions and separation processes
• Metal processing: ionic liquids in metal deposition processes
• Separation processing
• Polymer processing: dissolving and processing cellulose fibres,
antistatic polymer additives
• Electrolytes in electronic devices
• Functional fluids: hydraulic fluid and lubricants
Emulsions
• Emulsions are biphasic liquid systems consisting of two immiscible
liquid phases. These phases are present in such as way that one phase
is dispersed in the other continuous phase.
• . Examples of emulsions include mayonnaise, milk, lotions, etc.
• Types of Emulsions
1) Oil in water
2) Water in oil
• The type of emulsion depends upon the properties of the dispersed
phase and continuous phase.
1) Oil in water
• Oil phase is dispersed in a continuous aqueous phase.
2) Water in oil
• Aqueous phase is the dispersed phase and the oil phase is the
continuous phase.
Uses of emulsions
• They are used for drug delivery in medicine, cleaning of oil and greasy
surfaces, storage of substances, etc.
• The routes of medication administration by which emulsions are
given include by oral, parenteral and even few topical preparations
(creams).
• They are a bit advanced in terms of their stability and making.
• One liquid phase is evenly spread in the other liquid phase.
• The one which is a large proportion is called the external phase while
the one which is in lower proportions is called internal phase.
• The internal phase and external phase liquids are insoluble.
Methods of emulsion breaking
• Thermal methods
• Heating reduces the oil viscosity and increases the water-settling rates. Increased
temperatures also result in the destabilization of the rigid films because of reduced
interfacial viscosity. Furthermore, the coalescence frequency of water droplets is
increased because of the higher thermal energy of the droplets. See Heating oil
emulsions for more information. Heat accelerates emulsion breaking; however, it very
rarely resolves the emulsion problem alone. Increasing the temperature has some
negative effects.
• It costs money to heat the emulsion stream.
• Heating can result in the loss of light ends from the crude oil, reducing its API gravity
and the treated oil volume.
• Increasing the temperature leads to an increased tendency toward some forms of scale
deposition and an increased potential for corrosion in treating vessels.
•Mechanical methods
•There is a wide variety of mechanical equipment
available for breaking oilfield emulsions
including:
•Desalters
•Settling tanks
• Chemical methods
• The most common method of emulsion treatment is adding
demulsifiers. These chemicals are designed to neutralize the
stabilizing effect of emulsifying agents. Demulsifiers are surface-active
compounds that, when added to the emulsion, migrate to the
oil/water interface, rupture or weaken the rigid film, and enhance
water droplet coalescence.
• Demulsifier chemicals contain the following components:
• Solvents
• Surface-active ingredients
• Flocculants
Why Ionic liquids?
• Application of the Ionic Liquids in chemical processes has increased
significantly and is used as replacement of the volatile organic
solvents due to following properties
1) Non-toxic
2) Thermally stable
3) Non-flammable
4) Good solvent for both organic and inorganic compounds
Experiments
Emulsion preparation:
 Aim : 20% v/v water in oil emulsion
 Apparatus : 250ml glass beaker, Thermometer, RPM machine with
heating mantle, Magnetic stirrer
 Chemicals used : Castor oil, water
Procedure
Add 100 ml oil in beaker
Heat oil at 45-50°c and 1500 RPM
Dropwise add water in oil to form 20%
v/v emulsion
Ionic liquid preparation procedure
Powder (wash with
20 ml hexane and
dry)
Heating
mixture at
80°c for 30
min
12 mmol of
alkyl
bromide
10 mmol of
trimethyl
Process
• To prepare ionic liquid , we took
• 0.5 mole of butyl bromide in round bottom flask with 2 necks
• 0.5 mole of triethylamine in burrete
• The flask was placed on a magnetic machine with stirrer and was maintained at 50
degree
• Then triethylamine amine was added drop wise in the flask and stirring was constantly
provided
• This mixture was kept for stirring for about 2 hours
• Approx 50 ml mixture was formed
• Then we took 15 ml mixture and added 4 ml Toluene and heated mixture at 85 degree
• Then these ionic. Liquid was mixed with 5 ml emulsion and heated at 70 degree and
some amount of water was seperated
Pics of experiments
References
• 1.IUPAC (1997). (The "Gold Book")
Compendium of Chemical Terminology
. Oxford: Blackwell Scientific Publications. Archived from the original on 2012-03-10.
• 2.Slomkowski, Stanislaw; Alemán, José V.; Gilbert, Robert G.; Hess, Michael; Horie, Kazuyuki; Jones, Richard G.; Kubisa, Przemyslaw; Meisel, Ingrid; Mormann, Werner; Penczek, Stanisław; Stepto,
Robert F. T. (2011). "Terminology of polymers and polymerization processes in dispersed systems (IUPAC Recommendations 2011)". Pure and Applied Chemistry. 83 (12): 2229–2259.
• 3. https://sci-hub.tw/https://www.sciencedirect.com/science/article/pii/S0016236118308299
• 4. https://sci-hub.tw/https://pubs.acs.org/doi/abs/10.1021/ef100232f
5. https://sci-hub.tw/https://www.researchgate.net/publication/330873697_Demulsification_of_water-in-oil_emulsions_using_ionic_liquids_Effects_of_counterion_and_water_type
• 6.https://r.search.yahoo.com/_ylt=Awrxgvk2CqNe1RoAlWfnHgx.;_ylu=X3oDMTByYmpmZjA4BGNvbG8Dc2czBHBvcwMzBHZ0aWQDBHNlYwNzcg--
/RV=2/RE=1587772087/RO=10/RU=https%3a%2f%2fwww.sigmaaldrich.com%2ftechnical-documents%2farticles%2fchemfiles%2fionic-liquids0.html/RK=2/RS=q979sKo3fOQtA6mWK5YhEb.cSOQ-
• 7.https://r.search.yahoo.com/_ylt=Awrxgvk2CqNe1RoAjmfnHgx.;_ylu=X3oDMTByaW0wdmlxBGNvbG8Dc2czBHBvcwMyBHZ0aWQDBHNlYwNzcg--
/RV=2/RE=1587772087/RO=10/RU=https%3a%2f%2fwww.sciencedirect.com%2ftopics%2fchemistry%2fionic-liquid/RK=2/RS=6CTXeCQMK5oCYPaEs1rbIYBX3OY-
• 8. https://www.sciencedirect.com/science/article/abs/pii/S0167732217335171
• 9. https://www.sciencedirect.com/science/article/abs/pii/S0167732219363615
• 10. https://www.sciencedirect.com/science/article/abs/pii/S016773221834039X
• 11. R. López-Fonseca, I. Duque-Ingunza, B. de Rivas, L. Flores-Giraldo, I. Gutiérrez-Ortiz, Chem. Eng. J. 168 (2011) 312.
• 12. A. Al-Sabagh, F. Yehia, G. Eshaq, A. Rabie, A. ElMetwally, Egypt. j. petrol. 25 (2016) 53. [3] M.-J. Li, Y.-H. Huang, A.-Q. Ju, T.-S. Yu, M.-Q. Ge, Chin. Chem. Lett. 25 (2014) 1550. [4] F. Welle,
Resour. Conserv. Recy. 55 (2011) 865.
• 13. T.P. Vilela, (2014).
• 14. L.N.T. Ho, D.M. Ngo, J. Cho, H.M. Jung, Polym. Degrad. Stab. 155 (2018) 15.
• 15. G. Polat, B. Birol, M.N. Sarıdede, Int. J Mjn. Met. Mater. 21 (2014) 748.

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basics of ionic liquids and emulsions

  • 1. Synthesis of ionic liquid to break oil-water emulsions By Hunny Kukdeja (17bch026) Vikram Kataria (17bch058)
  • 2. Contents • Intro • Properties • RTILs • Cons of ionic liquid • Pros of ionic liquid • Application of ionic liquid • Emulsions • Uses of emulsions • Methods of emulsion breaking • Experiments • References
  • 3. Ionic liquids • Ionic liquids (ILs) are the organic or may be inorganic salts, generally consisting of an organic cations and a polyatomic organic or inorganic anions, that are in the form of liquid phase below 100°C.
  • 4. Science of ionic liquid • An ionic liquid is a salt in which the ions are poorly coordinated, which results in these solvents being liquid below 100°C, or even at room temperature (room temperature ionic liquids, RTIL's). At least one ion has a delocalized charge and one component is organic, which prevents the formation of a stable crystal lattice.
  • 5. Glimpse on properties Properties, such as melting point, viscosity, and solubility of starting materials and other solvents, are determined by the substituents on the organic component and by the counterion. Many ionic liquids have even been developed for specific synthetic problems. For this reason, ionic liquids have been termed "designer solvents".
  • 6. RTILs • One of the first RTILs was a mixture of [emim]Cl with AlCl3 forming a series of equilibria between [emim][AlCl4], [emim][Al2Cl7], and [emim][Al3Cl10]. This RTIL is not water stable. The discovery of water-insoluble RTILs such as [bmim][PF6] allowed the development of new work-up methods, including the separation of water-soluble by products by simple extraction.
  • 7. Pros of ionic liquid • Absence of volatility • Much lower toxicity as compared to lower boiling point solvents • They can make safer microwave synthesis • The dipole characteristics of ionic liquids translate into rapid excitation by microwaves, and consequently faster reactions.
  • 8. Cons of ionic liquid • Ionic liquids have the potential to be green alternatives to conventional organic solvents currently utilised by the pharmaceutical industry. However, several factors still have to be addressed before this new technology is unconditionally welcomed by the pharmaceutical industry. Issues encompassing cost, stability, toxicity, ease of processing of pharmaceutical intermediate(s), and advantages over conventional solvents
  • 9. Applications of Ionic liquid • Chemical processing in chemical reactions and separation processes • Metal processing: ionic liquids in metal deposition processes • Separation processing • Polymer processing: dissolving and processing cellulose fibres, antistatic polymer additives • Electrolytes in electronic devices • Functional fluids: hydraulic fluid and lubricants
  • 10. Emulsions • Emulsions are biphasic liquid systems consisting of two immiscible liquid phases. These phases are present in such as way that one phase is dispersed in the other continuous phase. • . Examples of emulsions include mayonnaise, milk, lotions, etc. • Types of Emulsions 1) Oil in water 2) Water in oil
  • 11. • The type of emulsion depends upon the properties of the dispersed phase and continuous phase. 1) Oil in water • Oil phase is dispersed in a continuous aqueous phase. 2) Water in oil • Aqueous phase is the dispersed phase and the oil phase is the continuous phase.
  • 12. Uses of emulsions • They are used for drug delivery in medicine, cleaning of oil and greasy surfaces, storage of substances, etc. • The routes of medication administration by which emulsions are given include by oral, parenteral and even few topical preparations (creams). • They are a bit advanced in terms of their stability and making. • One liquid phase is evenly spread in the other liquid phase. • The one which is a large proportion is called the external phase while the one which is in lower proportions is called internal phase. • The internal phase and external phase liquids are insoluble.
  • 13. Methods of emulsion breaking • Thermal methods • Heating reduces the oil viscosity and increases the water-settling rates. Increased temperatures also result in the destabilization of the rigid films because of reduced interfacial viscosity. Furthermore, the coalescence frequency of water droplets is increased because of the higher thermal energy of the droplets. See Heating oil emulsions for more information. Heat accelerates emulsion breaking; however, it very rarely resolves the emulsion problem alone. Increasing the temperature has some negative effects. • It costs money to heat the emulsion stream. • Heating can result in the loss of light ends from the crude oil, reducing its API gravity and the treated oil volume. • Increasing the temperature leads to an increased tendency toward some forms of scale deposition and an increased potential for corrosion in treating vessels.
  • 14. •Mechanical methods •There is a wide variety of mechanical equipment available for breaking oilfield emulsions including: •Desalters •Settling tanks
  • 15. • Chemical methods • The most common method of emulsion treatment is adding demulsifiers. These chemicals are designed to neutralize the stabilizing effect of emulsifying agents. Demulsifiers are surface-active compounds that, when added to the emulsion, migrate to the oil/water interface, rupture or weaken the rigid film, and enhance water droplet coalescence. • Demulsifier chemicals contain the following components: • Solvents • Surface-active ingredients • Flocculants
  • 16. Why Ionic liquids? • Application of the Ionic Liquids in chemical processes has increased significantly and is used as replacement of the volatile organic solvents due to following properties 1) Non-toxic 2) Thermally stable 3) Non-flammable 4) Good solvent for both organic and inorganic compounds
  • 17. Experiments Emulsion preparation:  Aim : 20% v/v water in oil emulsion  Apparatus : 250ml glass beaker, Thermometer, RPM machine with heating mantle, Magnetic stirrer  Chemicals used : Castor oil, water
  • 18. Procedure Add 100 ml oil in beaker Heat oil at 45-50°c and 1500 RPM Dropwise add water in oil to form 20% v/v emulsion
  • 19. Ionic liquid preparation procedure Powder (wash with 20 ml hexane and dry) Heating mixture at 80°c for 30 min 12 mmol of alkyl bromide 10 mmol of trimethyl
  • 20. Process • To prepare ionic liquid , we took • 0.5 mole of butyl bromide in round bottom flask with 2 necks • 0.5 mole of triethylamine in burrete • The flask was placed on a magnetic machine with stirrer and was maintained at 50 degree • Then triethylamine amine was added drop wise in the flask and stirring was constantly provided • This mixture was kept for stirring for about 2 hours • Approx 50 ml mixture was formed • Then we took 15 ml mixture and added 4 ml Toluene and heated mixture at 85 degree • Then these ionic. Liquid was mixed with 5 ml emulsion and heated at 70 degree and some amount of water was seperated
  • 22. References • 1.IUPAC (1997). (The "Gold Book") Compendium of Chemical Terminology . Oxford: Blackwell Scientific Publications. Archived from the original on 2012-03-10. • 2.Slomkowski, Stanislaw; Alemán, José V.; Gilbert, Robert G.; Hess, Michael; Horie, Kazuyuki; Jones, Richard G.; Kubisa, Przemyslaw; Meisel, Ingrid; Mormann, Werner; Penczek, Stanisław; Stepto, Robert F. T. (2011). "Terminology of polymers and polymerization processes in dispersed systems (IUPAC Recommendations 2011)". Pure and Applied Chemistry. 83 (12): 2229–2259. • 3. https://sci-hub.tw/https://www.sciencedirect.com/science/article/pii/S0016236118308299 • 4. https://sci-hub.tw/https://pubs.acs.org/doi/abs/10.1021/ef100232f 5. https://sci-hub.tw/https://www.researchgate.net/publication/330873697_Demulsification_of_water-in-oil_emulsions_using_ionic_liquids_Effects_of_counterion_and_water_type • 6.https://r.search.yahoo.com/_ylt=Awrxgvk2CqNe1RoAlWfnHgx.;_ylu=X3oDMTByYmpmZjA4BGNvbG8Dc2czBHBvcwMzBHZ0aWQDBHNlYwNzcg-- /RV=2/RE=1587772087/RO=10/RU=https%3a%2f%2fwww.sigmaaldrich.com%2ftechnical-documents%2farticles%2fchemfiles%2fionic-liquids0.html/RK=2/RS=q979sKo3fOQtA6mWK5YhEb.cSOQ- • 7.https://r.search.yahoo.com/_ylt=Awrxgvk2CqNe1RoAjmfnHgx.;_ylu=X3oDMTByaW0wdmlxBGNvbG8Dc2czBHBvcwMyBHZ0aWQDBHNlYwNzcg-- /RV=2/RE=1587772087/RO=10/RU=https%3a%2f%2fwww.sciencedirect.com%2ftopics%2fchemistry%2fionic-liquid/RK=2/RS=6CTXeCQMK5oCYPaEs1rbIYBX3OY- • 8. https://www.sciencedirect.com/science/article/abs/pii/S0167732217335171 • 9. https://www.sciencedirect.com/science/article/abs/pii/S0167732219363615 • 10. https://www.sciencedirect.com/science/article/abs/pii/S016773221834039X • 11. R. López-Fonseca, I. Duque-Ingunza, B. de Rivas, L. Flores-Giraldo, I. Gutiérrez-Ortiz, Chem. Eng. J. 168 (2011) 312. • 12. A. Al-Sabagh, F. Yehia, G. Eshaq, A. Rabie, A. ElMetwally, Egypt. j. petrol. 25 (2016) 53. [3] M.-J. Li, Y.-H. Huang, A.-Q. Ju, T.-S. Yu, M.-Q. Ge, Chin. Chem. Lett. 25 (2014) 1550. [4] F. Welle, Resour. Conserv. Recy. 55 (2011) 865. • 13. T.P. Vilela, (2014). • 14. L.N.T. Ho, D.M. Ngo, J. Cho, H.M. Jung, Polym. Degrad. Stab. 155 (2018) 15. • 15. G. Polat, B. Birol, M.N. Sarıdede, Int. J Mjn. Met. Mater. 21 (2014) 748.