using water to replace organic solvents: switchable water · 3/28/2013 · “salting-out”...
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Using Water to Replace Organic Solvents:
Switchable Water
Download the presentation ONE WEEK after webinar:
http://acswebinars.org/switchable-water
ACS WEBINARS™ March 28, 2013
Co-Produced with the ACS Green Chemistry Institute
Dr. Philip Jessop
Queen’s University
Dr. Joseph Fortunak
Howard University
10
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Switchable Water
Philip G. Jessop
Queen’s University and GreenCentre Canada
Kingston, Ontario, Canada 11
If the adoption of greener solvents over the next 20-30
years will reduce environmental damage from human
activities, then the adoption of what class of solvents will be
responsible for the greatest reduction in environmental
damage?
1. Ionic liquids
2. Water (including liquid, superheated, supercritical, on-water)
3. CO2 (liquid, supercritical, etc.)
4. Conventional organic solvents (including bio-derived organic
solvents)
5. Switchable or “smart” solvents
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SURVEY
If the adoption of greener solvents over the next 20-30 years will reduce
environmental damage from human activities, then the adoption of what
class of solvents will be responsible for the greatest reduction in
environmental damage?
1. Bioderived solvents (glycerol, 2-methylTHF, valerolactone, etc.)
2. CO2 (liquid, supercritical, etc.)
3. Conventional organic solvents (carefully selected)
4. Ionic liquids
5. Switchable or “smart” solvents
6. Solvent-free conditions
7. Water (including liquid, superheated, supercritical, on-water)
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IS WATER A GREEN SOLVENT?
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SALTY WATER
salty
water
Useful for:
collapsing emulsions
collapsing suspensions
“salting out” organic contaminants
. . . . .
. . .
. . . . .
. . .
BUT:
can’t be easily de-salinated
can’t be re-used
can’t be discarded
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SWITCHABLE WATER
(aqueous solutions of switchable ionic strength)
non-salty
water
salty
water
ChemSusChem (2010) 3, 467
Green Chem (2012) 14, 832
- CO2
CO2
B [BHnn+][O2COH]n - CO2
CO2
low ionic strength high ionic strength
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APPLICATIONS OF SWITCHABLE WATER
Salting-out organic contaminants/products
Extractions of water-soluble compounds
Settling of suspensions
Breaking of emulsions
Breaking of foams
Desalination of seawater by forward osmosis
Dewatering of wastewater by forward osmosis
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“SALTING-OUT” ORGANICS FROM WATER
THF +
water +
additive
THF
water +
additive
- CO2
CO2
B [BHnn+][O2COH]n - CO2
CO2
5:5:1
87% expelled
99.6% retained
ChemSusChem (2010) 3, 467
Green Chem (2012) 14, 832
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“SALTING-OUT” ORGANICS FROM WATER
THF +
water +
additive
THF
water +
additive
- CO2
CO2
B [BHnn+][O2COH]n - CO2
CO2
ChemSusChem (2010) 3, 467
Green Chem (2012) 14, 832
4N ≥ 3N > 2N >> 1N
4C > 3C, 5C > 2C, 6C
III˚ > I˚, II˚
APPLICATION #1: EXTRACTIONS
20
Extract with“nonsalty” switchable water
product & switchable
water
Add CO2
“salty” switchable
water
product
product
“salty” switchable
water
- CO2
“nonsalty” switchable
water
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APPLICATION #2: HOW TO MAKE CLAY SETTLE?
Chemicals to Cause Settling
Ca2+ salts
Polyacrylamide
22
limit of instrument
KAOLINITE SETTLING
AFPMMA
120,000
Green Chem (2012) 14, 3053
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APPLICATION #3: CONTROLLING CONVENTIONAL SURFACTANTS
23
Most surfactants are NOT CO2-switchable
emulsion of 1-octanol in
water stabilized by SDS
Chem Eur J (2013) in press
24
APPLICATION #4: SWITCHABLE VISCOSITY
low viscosity
1.2 cP
high viscosity
26,000 cP
Chem Commun (2013) 49, 2655
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Salt Water
Semi-Permeable
FO Membrane
+ + + ++
+
++
++ + +
--
-
--
-
-
- - -
Water Flow
-
-
CO2
APPLICATION #5: FORWARD OSMOSIS
CO2
Semi-Permeable
FO Membrane
Water Flow
Salt Water
+ + + ++
+
++
++ + +
--
-
--
-
-
- - -
-
-
APPLICATION #5: FORWARD OSMOSIS
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-
-
CO2
Semi-Permeable
FO Membrane
+ + + ++
+
++
++ + +
--
-
--
-
-
- - -
-
-
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APPLICATION #5: FORWARD OSMOSIS
-
-
air
Semi-Permeable
FO Membrane
APPLICATION #5: FORWARD OSMOSIS
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Amine Removal
Gas Volatilization
Liquid Decantation
Solid (polymer) Precipitation or RO
Amine Removal method
Gas Volatilization
Liquid Decantation
Solid (polymer) Precipitation or RO
Amine Removal
Gas Volatilization
Liquid Decantation
Solid (polymer) Precipitation or RO
Feed Solution (1 L) Draw solution
volume increase*
3% NaCl
(seawater) 380 mL
15% NaCl
(“frack” water) 91 mL
*starting at 100 mL
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CONCLUDING THOUGHTS
“Switchable water” allows us to use CO2 as
a trigger to control:
1. viscosity
2. osmotic pressure
3. surface tension
4. solubility of organics in water
5. emulsion & suspension stability
Which of these is potentially most useful?
for a review of CO2-switchable materials, see: Energy & Env. Sci., (2012) 5, 7240
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CONCLUDING THOUGHTS
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4/1/2013
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Using Water to Replace Organic Solvents:
Switchable Water
Download the presentation ONE WEEK after webinar:
http://acswebinars.org/switchable-water
ACS WEBINARS™ March 28, 2013
Co-Produced with the ACS Green Chemistry Institute
Dr. Philip Jessop
Queen’s University
Dr. Joseph Fortunak
Howard University
31
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Upcoming ACS Webinars™ www.acswebinars.org
Thursday, April 4, 2013
From Lab Hoods to Front Lines:
Chemists at U.S. Customs and Border Protection
Chris Mocella, U.S. Customs and Border Protection
Patricia Simpson, Director of Academic Advising, University of Illinois
Thursday, April 18, 2013
From Academia to Entrepreneurship
Barbara Bry, COO, Blackbird Ventures
Dr. Yu Mike Chi, CTO, Cognionics, Inc.
Dr. Magda Marquet, Founder and Co-Chair, Althea Technologies
Contact ACS Webinars™ at [email protected] 33
$175M
ACS National Meeting New Orleans- LIVE from the comfort of your own home! (Day 1)
34 RSVP now at http://acswebinars.org/new-orleans-live
http://www.acswebinars.org/mailto:[email protected]
-
4/1/2013
18
ACS National Meeting New Orleans - LIVE from the comfort of your own home! (Day 2)
35 RSVP now at RSVP now at http://acswebinars.org/new-orleans-live
36
Coins for Cleaner Water
In partnership with Procter & Gamble (P&G),
ACS is raising money to provide clean, safe
drinking water to individuals in developing
countries around the world. Please join us in
this effort.
How your donation makes a difference!
• $1.00 gives a child clean water for 50 days.
• $7.50 gives a child clean water for a year.
• $30.00 gives a family clean water for a year.
Please visit www.acs.org/cleanerwater for more information on how you can contribute.
http://www.acs.org/cleanerwater
-
4/1/2013
19
Acknowledgement:
This presentation was co-produced by the
ACS Green Chemistry Institute.
For more information please visit http://bit.ly/AcsGCI
37
If you enjoyed this ACS Webinar today…
please support the program!
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Find the many benefits of ACS membership!
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this presentation are those of the presenter
and do not necessarily reflect the views or
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