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Green Solvents and Ionic Liquids:
 Formulating for the Sustainable Future



                                  Stanley S. Seelig, President/Owner
                                 Anthony O’Lenick, Managing Dir/Owner
                                       Waterless Cleaning LLC




       The 101st American Oil Chemist’s Society Annual & Expo   May 18, 2010
Green Solvents and Ionic Liquids

Waterless Cleaning LLC is
100 % owned by Stan Seelig and Tony O’Lenick, with combined 60 years of
industrial/consumer experience in cleaning/personal care

Mission Statement
To provide green/sustainable cleaning formulations using “green” solvents and
ionic liquid co-solvents for the replacement of wasteful, water-based
formulations and practices

Company Vision
1. To license green and sustainable solvent-based cleaning formulations to
   industry.
2. To sell specialty ionic liquids that provide multiple benefits for a lower overall
   cost into cleaning/other markets.


                                                                             May 18, 2010
Green Solvents and Ionic Liquids

What are “Green” Solvents ?
(for our applications)
• Not halogenated, non-flammable (< 100 0C), non-hazardous, non-toxic

• Low /no VOC

• BP < 200 0C

• Biodegradable, stable, recyclable

• Low water solubility (< 5 wt% in solvent)


Best choices are solvents derived from bio-diesel, plant, natural products

                                                                 May 18, 2010
Green Solvents and Ionic Liquids

Choosing the Right Green Solvent(s)
Considerations
• Low pricing (< $ 1.50/lb)
• World-wide availability, high volume potential
• Safe for people /environment
• Low /no VOC
• Compatibilities (w/equipment /materials to be cleaned)
• Equipment design
• Examples – dibasic esters, lactates, soy-based, Si-based, others

                                                               May 18, 2010
Green Solvents and Ionic Liquids

What are Ionic Liquids (ILS) ?
Our ILs are:
• Combinations of cations(+) and anions(-)

• Liquids (viscous) at room temperature (RTILs)

• Cross between “Green” solvents and surfactants

• Hydrophobic, non-halogenated, no unusual cyclic structures,
  conductive, simple

• Less expensive (ours < $1/gm, others > $100/gm)

                                                                May 18, 2010
Green Solvents and Ionic Liquids

Applications for Ionic Liquids
• Solvents for pharmaceutical manufacturing

• Lubricants

• Extending the life of a lithium battery

• Dispersants in paints

• Solar energy (heat transfer and storage medium)

• Electrochemical applications


• Cleaning and drying
                                                    May 18, 2010
Green Solvents and Ionic Liquids

Primary Project
To develop a revolutionary change in the cleaning of fabrics by
combining dry cleaning concepts and water-based laundry systems into
a green and sustainable laundry system for institutional, industrial,
commercial, and consumer laundry operations (without using water)

This is a Disruptive Technology !




                                                              May 18, 2010
Green Solvents and Ionic Liquids

Laundry Cleaning Today
Follows the Energy Star program by minimizing:
• Water usages
• Energy consumption
• Chemical usage
• Overall costs

But, we still dump billions of gallons of water down the drain every
day (containing more detergent than contamination ) !

Is this a Sustainable Process ?



                                                             May 18, 2010
Green Solvents and Ionic Liquids

Is water, the Next Oil ?
• 3% of the Earth has drinkable water

• 1% of the 3% is accessible (rest is tied up in glaciers)

• 20% of the 1% is found in the Great Lakes Region (USA)

Ethical Challenge: We need to minimize our use of drinking water for
non-essential applications (i.e., laundry, dishwasher, toilets, watering
lawns, washing cars, etc). Our waste water streams are running on
maximum.



                                                                  May 18, 2010
Green Solvents and Ionic Liquids

Laundry Cleaning Tomorrow
Moving towards Waterless (Dry) Cleaning

• Cold water cleaning w/minimal water and energy

• Cleaning w/ozone (O3 injected water reduces heat), 2003

• Self cleaning laundry (coating repels water and dirt), 2004

• Cleaning w/polymer beads (90% water reduction), 2009

• Cleaning w/green solvents and ionic liquids (no free water), 2011

Equipment patents exist already for consumer solvent cleaning!

                                                                May 18, 2010
Green Solvents and Ionic Liquids

Current Vision for Laundry Cleaning
• Target: Institutional markets now (hotels, hospitals, nursing homes,
  schools, military, prisons, etc.)
• Support from Customer Relationships (detergent manu)
• Form Strategic Alliances with “green” solvent manu
• Form Partnerships with equipment manufacturers

• (Anticipated) Cleaning Solvent Composition
    –   Green Solvent                                            > 90%
    –   Water                                                    < 5%
    –   Ionic liquid co-solvent(s)                               < 1%
    –   Other additives (brighteners, fragrances, surfactants)   < 4%
                                                                         May 18, 2010
Green Solvents and Ionic Liquids

Current Vision for Laundry Cleaning
• “Green” solvent + detergent package (ILs) will clean ~20-40 loads of
   laundry (based on density limits) with rinsing

• Cleaning solvent would be filtered/recovered; waste residue sent for
   disposal (after accumulation)

• Rinse solvent becomes cleaning solvent

• Add fresh (or recycled) solvent to rinse tank



                                                               May 18, 2010
Green Solvents and Ionic Liquids

Current Vision for Laundry Cleaning
(Institutional model)                               2 -add detergent,                 Fresh/
                        3                                                             recycled
                                                    then clothes
                                                                                      solvent
                        1
                                                                                  5 +
                                                                                  spin
                                                                    4             dryer
                                          B



         Cleaning                                                        Rinse
 A       Solvent                                                        Solvent             C

                                       Distillate
     After x washings



                        Distillation    Waste       Recycled                       May 18, 2010
                                                     solvent
Green Solvents and Ionic Liquids

Actual Cost Comparisons at Local Marriott
Water-based system (special thanks to Diversey, Inc)
        Current System            Cost          Usage            Cost/Month

        Water Cost:           $ 0.00075          147,000          $110.25
                                $/Liter          L/Month

        Energy Cost:          $         0.15      3200            $480.00
        (natural gas)             $/M3          M3/Month

        Chemical Cost:              -               -            $ 500.00

        Total Cost                                                $1,090.25

        (multiple machines)   Water usage Load Processed/month
        10:1 ratio             147,000            14,700         $ 0.07417
                               L/Month              Kg            Cost/Kg
                                                                  Laundry
                                   525            52.5             280.00
                                  L/load         Kg/load         Loads/month

                                                                               May 18, 2010
Green Solvents and Ionic Liquids

Theoretical Cost Comparisons at Local Marriott
Solvent density assumed 1.0


Solvent System                                                                   Usage Solvent   Solvent


$ 1.00/lb                          Kg/1st load   Assumptions                     Kg/month        Cost/1st Month


Solvent usage                          525                                          147,000      $ 323,564.20

per load                                         No solvent recovery

                                                 (100% solvent loss)

Solvent usage                          525       99% solvent recovery                147.00      $         323.56   plus Energy (E) to run still

per load                                         or 0.525Kg loss                                                    Solvent recovery is based on drag out by the

                                                 for every load of laundry                                          laundry load wt which is 99% per load

Solvent usage                          525       81.8% solvent recovery              133.84      $         294.60   plus E/20 to run still
                                                                                                                                                            X
per 20 loads                                     or 9.56Kg loss                                                     Solvent recovery after 20 loads is 99 %

                                                 for every 20 loads of laundry                                      where x= 20 or 81.8% of the laundry load

Solvent usage                          525       66.9% solvent recovery              121.66      $         267.79   plus E/40 to run still
                                                                                                                                                       X
per 40 loads                                     or 17.38Kg loss                                                    Solvent recovery after 40 loads is 99 %

                                                 for every 40 loads of laundry                                      where x= 40 or 66.9% of the laundry load

Solvent loss based on 1% of laundry weight

With solvent recovery, you begin next month with a full solvent charge

Initial charge cost:             $ 1,155.59




                                                                                                                                                                May 18, 2010
Green Solvents and Ionic Liquids

Theoretical Cost Comparisons at Local Marriott
       Proposed Solvent System      Cost              Usage                Cost/Month


       Solvent Cost:                2.20              133.84           $     294.60
           (used)                  $/Liter          L/Month per 20 loads


       Energy Cost:              $ 0.15                800                  $120.00

         (no drying)                $/M3            M3/Month          assumed 25%


    Chemical Cost:                   assumed same                      $     500.00



    Initial Solvent Cost         1st month                                 $1,155.59
                                                                                                vs
    Total Monthly Cost           2nd month                                 $ 914.60         $1,090.25
                                                                                           (for water)


                                                                                        May 18, 2010
Green Solvents and Ionic Liquids

Solvent Cleaning Benefits (1)
• Energy Efficient – Energy to heat solvent < water; spin drying of
   solvent>water; IL repels the solvent; no dryer expected!

• Water Efficient – no water is used; solvent will clean 20-40 loads
   depending on contamination and density

• Cleaning Efficiency – recycling solvent means less added chemicals;
   fabrics will look/smell as if cleaned using water

• Environmentally safer – solvents are low/non-VOCs, non-hazardous,
   biodegradable, non-toxic
                                                               May 18, 2010
Green Solvents and Ionic Liquids

Solvent Cleaning Benefits (2)
• Softening and Cleaning – ILs add softening, anti-static, cleaning,
  anti-bacterial(?), fragrance retention properties

• Recyclability – solvent used 20-40 times with clean rinses

• Reclaimability – used solvents are recovered for future use

• Equal/Better Overall Cleaning Performance – contaminants are
  (1) filtered off and (2) part of distillation residues

• Closed-Loop Process


                                                                May 18, 2010
Green Solvents and Ionic Liquids


Waterless Cleaning must
• Work with Potential Customers in institutional laundry

• Form a Strategic Alliance with key solvent manufacturers

• Form Partnerships with laundry equipment manufacturers

• Find Investors (angels, venture capitalists, banks, SBIR grants)

• Hire key personnel




                                                               May 18, 2010
Green Solvents and Ionic Liquids

Acknowledgements

Whirlpool            Ecolab
Rhodia               Dow Chemical
(Johnson) Diversey   Invista




                                    May 18, 2010

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Green Solvents And Ionic Liquids

  • 1. Green Solvents and Ionic Liquids: Formulating for the Sustainable Future Stanley S. Seelig, President/Owner Anthony O’Lenick, Managing Dir/Owner Waterless Cleaning LLC The 101st American Oil Chemist’s Society Annual & Expo May 18, 2010
  • 2. Green Solvents and Ionic Liquids Waterless Cleaning LLC is 100 % owned by Stan Seelig and Tony O’Lenick, with combined 60 years of industrial/consumer experience in cleaning/personal care Mission Statement To provide green/sustainable cleaning formulations using “green” solvents and ionic liquid co-solvents for the replacement of wasteful, water-based formulations and practices Company Vision 1. To license green and sustainable solvent-based cleaning formulations to industry. 2. To sell specialty ionic liquids that provide multiple benefits for a lower overall cost into cleaning/other markets. May 18, 2010
  • 3. Green Solvents and Ionic Liquids What are “Green” Solvents ? (for our applications) • Not halogenated, non-flammable (< 100 0C), non-hazardous, non-toxic • Low /no VOC • BP < 200 0C • Biodegradable, stable, recyclable • Low water solubility (< 5 wt% in solvent) Best choices are solvents derived from bio-diesel, plant, natural products May 18, 2010
  • 4. Green Solvents and Ionic Liquids Choosing the Right Green Solvent(s) Considerations • Low pricing (< $ 1.50/lb) • World-wide availability, high volume potential • Safe for people /environment • Low /no VOC • Compatibilities (w/equipment /materials to be cleaned) • Equipment design • Examples – dibasic esters, lactates, soy-based, Si-based, others May 18, 2010
  • 5. Green Solvents and Ionic Liquids What are Ionic Liquids (ILS) ? Our ILs are: • Combinations of cations(+) and anions(-) • Liquids (viscous) at room temperature (RTILs) • Cross between “Green” solvents and surfactants • Hydrophobic, non-halogenated, no unusual cyclic structures, conductive, simple • Less expensive (ours < $1/gm, others > $100/gm) May 18, 2010
  • 6. Green Solvents and Ionic Liquids Applications for Ionic Liquids • Solvents for pharmaceutical manufacturing • Lubricants • Extending the life of a lithium battery • Dispersants in paints • Solar energy (heat transfer and storage medium) • Electrochemical applications • Cleaning and drying May 18, 2010
  • 7. Green Solvents and Ionic Liquids Primary Project To develop a revolutionary change in the cleaning of fabrics by combining dry cleaning concepts and water-based laundry systems into a green and sustainable laundry system for institutional, industrial, commercial, and consumer laundry operations (without using water) This is a Disruptive Technology ! May 18, 2010
  • 8. Green Solvents and Ionic Liquids Laundry Cleaning Today Follows the Energy Star program by minimizing: • Water usages • Energy consumption • Chemical usage • Overall costs But, we still dump billions of gallons of water down the drain every day (containing more detergent than contamination ) ! Is this a Sustainable Process ? May 18, 2010
  • 9. Green Solvents and Ionic Liquids Is water, the Next Oil ? • 3% of the Earth has drinkable water • 1% of the 3% is accessible (rest is tied up in glaciers) • 20% of the 1% is found in the Great Lakes Region (USA) Ethical Challenge: We need to minimize our use of drinking water for non-essential applications (i.e., laundry, dishwasher, toilets, watering lawns, washing cars, etc). Our waste water streams are running on maximum. May 18, 2010
  • 10. Green Solvents and Ionic Liquids Laundry Cleaning Tomorrow Moving towards Waterless (Dry) Cleaning • Cold water cleaning w/minimal water and energy • Cleaning w/ozone (O3 injected water reduces heat), 2003 • Self cleaning laundry (coating repels water and dirt), 2004 • Cleaning w/polymer beads (90% water reduction), 2009 • Cleaning w/green solvents and ionic liquids (no free water), 2011 Equipment patents exist already for consumer solvent cleaning! May 18, 2010
  • 11. Green Solvents and Ionic Liquids Current Vision for Laundry Cleaning • Target: Institutional markets now (hotels, hospitals, nursing homes, schools, military, prisons, etc.) • Support from Customer Relationships (detergent manu) • Form Strategic Alliances with “green” solvent manu • Form Partnerships with equipment manufacturers • (Anticipated) Cleaning Solvent Composition – Green Solvent > 90% – Water < 5% – Ionic liquid co-solvent(s) < 1% – Other additives (brighteners, fragrances, surfactants) < 4% May 18, 2010
  • 12. Green Solvents and Ionic Liquids Current Vision for Laundry Cleaning • “Green” solvent + detergent package (ILs) will clean ~20-40 loads of laundry (based on density limits) with rinsing • Cleaning solvent would be filtered/recovered; waste residue sent for disposal (after accumulation) • Rinse solvent becomes cleaning solvent • Add fresh (or recycled) solvent to rinse tank May 18, 2010
  • 13. Green Solvents and Ionic Liquids Current Vision for Laundry Cleaning (Institutional model) 2 -add detergent, Fresh/ 3 recycled then clothes solvent 1 5 + spin 4 dryer B Cleaning Rinse A Solvent Solvent C Distillate After x washings Distillation Waste Recycled May 18, 2010 solvent
  • 14. Green Solvents and Ionic Liquids Actual Cost Comparisons at Local Marriott Water-based system (special thanks to Diversey, Inc) Current System Cost Usage Cost/Month Water Cost: $ 0.00075 147,000 $110.25 $/Liter L/Month Energy Cost: $ 0.15 3200 $480.00 (natural gas) $/M3 M3/Month Chemical Cost: - - $ 500.00 Total Cost $1,090.25 (multiple machines) Water usage Load Processed/month 10:1 ratio 147,000 14,700 $ 0.07417 L/Month Kg Cost/Kg Laundry 525 52.5 280.00 L/load Kg/load Loads/month May 18, 2010
  • 15. Green Solvents and Ionic Liquids Theoretical Cost Comparisons at Local Marriott Solvent density assumed 1.0 Solvent System Usage Solvent Solvent $ 1.00/lb Kg/1st load Assumptions Kg/month Cost/1st Month Solvent usage 525 147,000 $ 323,564.20 per load No solvent recovery (100% solvent loss) Solvent usage 525 99% solvent recovery 147.00 $ 323.56 plus Energy (E) to run still per load or 0.525Kg loss Solvent recovery is based on drag out by the for every load of laundry laundry load wt which is 99% per load Solvent usage 525 81.8% solvent recovery 133.84 $ 294.60 plus E/20 to run still X per 20 loads or 9.56Kg loss Solvent recovery after 20 loads is 99 % for every 20 loads of laundry where x= 20 or 81.8% of the laundry load Solvent usage 525 66.9% solvent recovery 121.66 $ 267.79 plus E/40 to run still X per 40 loads or 17.38Kg loss Solvent recovery after 40 loads is 99 % for every 40 loads of laundry where x= 40 or 66.9% of the laundry load Solvent loss based on 1% of laundry weight With solvent recovery, you begin next month with a full solvent charge Initial charge cost: $ 1,155.59 May 18, 2010
  • 16. Green Solvents and Ionic Liquids Theoretical Cost Comparisons at Local Marriott Proposed Solvent System Cost Usage Cost/Month Solvent Cost: 2.20 133.84 $ 294.60 (used) $/Liter L/Month per 20 loads Energy Cost: $ 0.15 800 $120.00 (no drying) $/M3 M3/Month assumed 25% Chemical Cost: assumed same $ 500.00 Initial Solvent Cost 1st month $1,155.59 vs Total Monthly Cost 2nd month $ 914.60 $1,090.25 (for water) May 18, 2010
  • 17. Green Solvents and Ionic Liquids Solvent Cleaning Benefits (1) • Energy Efficient – Energy to heat solvent < water; spin drying of solvent>water; IL repels the solvent; no dryer expected! • Water Efficient – no water is used; solvent will clean 20-40 loads depending on contamination and density • Cleaning Efficiency – recycling solvent means less added chemicals; fabrics will look/smell as if cleaned using water • Environmentally safer – solvents are low/non-VOCs, non-hazardous, biodegradable, non-toxic May 18, 2010
  • 18. Green Solvents and Ionic Liquids Solvent Cleaning Benefits (2) • Softening and Cleaning – ILs add softening, anti-static, cleaning, anti-bacterial(?), fragrance retention properties • Recyclability – solvent used 20-40 times with clean rinses • Reclaimability – used solvents are recovered for future use • Equal/Better Overall Cleaning Performance – contaminants are (1) filtered off and (2) part of distillation residues • Closed-Loop Process May 18, 2010
  • 19. Green Solvents and Ionic Liquids Waterless Cleaning must • Work with Potential Customers in institutional laundry • Form a Strategic Alliance with key solvent manufacturers • Form Partnerships with laundry equipment manufacturers • Find Investors (angels, venture capitalists, banks, SBIR grants) • Hire key personnel May 18, 2010
  • 20. Green Solvents and Ionic Liquids Acknowledgements Whirlpool Ecolab Rhodia Dow Chemical (Johnson) Diversey Invista May 18, 2010