Using Water to Replace Organic Solvents: Switchable Water

4/1/2013

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ACS WEBINARS™ March 28, 2013 Using Water to Replace Organic Solvents: Switchable Water

Dr. Joseph Fortunak Howard University

Dr. Philip Jessop Queen’s University

Download the presentation ONE WEEK after webinar: http://acswebinars.org/switchable-water Co-Produced with the ACS Green Chemistry Institute

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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:

BUT:

collapsing emulsions

can’t be easily de-salinated

collapsing suspensions

can’t be re-used

“salting out” organic contaminants

can’t be discarded 15

SWITCHABLE WATER (aqueous solutions of switchable ionic strength)

CO2 non-salty water

- CO2

salty water

CO2 [BHnn+][O2COH]n

B - CO2 low ionic strength

ChemSusChem (2010) 3, 467 Green Chem (2012) 14, 832

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

CO2 THF

5:5:1

THF + water + additive

- CO2

water + additive

87% expelled 99.6% retained

CO2 B

[BHnn+][O2COH]n - CO2


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“SALTING-OUT” ORGANICS FROM WATER

CO2 THF THF + water + additive

- CO2

water + additive

CO2 [BHnn+][O2COH]n

B - CO2

4C > 3C, 5C > 2C, 6C III˚ > I˚, II˚

4N ≥ 3N > 2N >> 1N

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APPLICATION #1: EXTRACTIONS

Extract with “nonsalty” switchable water

Add CO2

product

“salty” switchable water

product & switchable water

- CO2

“nonsalty” switchable water

“salty” switchable water

product

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APPLICATION #2: HOW TO MAKE CLAY SETTLE?

Chemicals to Cause Settling Ca2+ salts Polyacrylamide

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KAOLINITE SETTLING

AFPMMA 120,000

limit of instrument

Green Chem (2012) 14, 3053

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APPLICATION #3: CONTROLLING CONVENTIONAL SURFACTANTS Most surfactants are NOT CO2-switchable

emulsion of 1-octanol in water stabilized by SDS

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Chem Eur J (2013) in press

APPLICATION #4: SWITCHABLE VISCOSITY

low viscosity 1.2 cP

Chem Commun (2013) 49, 2655

high viscosity 26,000 cP

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APPLICATION #5: FORWARD OSMOSIS

CO2

Semi-Permeable FO Membrane +

Salt Water

+

-

-

+

-

+

+ -

+

-

-

+ +

-

+ -

-

+

+

-

+

-

-

Water Flow 25


CO2


Salt Water

-

-

+

+

+ -

+

+

-

-

-

+

-

+

-

Water Flow

+ -

+

-

+

-

+

-

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CO2


+

+

+ -

+

-

+

-

-

-

+

-

+

-

+ -

+

-

+

-

+

-

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APPLICATION #5: FORWARD OSMOSIS Amine

Removal

Gas Gas

Volatilization Volatilization

Liquid Liquid

Decantation Decantation

Solid (polymer) (polymer) Solid

PrecipitationororRO RO Precipitation

Amine

Removal method

air

Semi-Permeable FO Membrane

Amine

Removal Draw solution

Gas

Volatilization

Feed Solution (1 L) 3% NaCl

(seawater) Liquid 15% NaCl

Solid (polymer) (“frack” water)

-

volume increase* 380 mL

-

Decantation

91 mL Precipitation or RO *starting at 100 mL 28

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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 29

CONCLUDING THOUGHTS

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Dr. Joseph Fortunak Howard University

Dr. Philip Jessop Queen’s University

Download the presentation ONE WEEK after webinar: http://acswebinars.org/switchable-water Co-Produced with the ACS Green Chemistry Institute

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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 $175M

Barbara Bry, COO, Blackbird Ventures Dr. Yu Mike Chi, CTO, Cognionics, Inc. Dr. Magda Marquet, Founder and Co-Chair, Althea Technologies


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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.

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Acknowledgement: This presentation was co-produced by the ACS Green Chemistry Institute.

For more information please visit http://bit.ly/AcsGCI 37

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Using Water to Replace Organic Solvents: Switchable Water

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