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Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Buckman International, Inc.
Enzymes Reduce the Energy and Wood Fiber Required
to Manufacture High-Quality Paper and Paperboard
2012 Presidential Green Chemistry Challenge Designing Greener
Chemicals Award
Center For Green Chemistry
and Green Engineering at Yale
Buckman International, Inc.
Summary:
Traditionally, making strong paper required costly wood pulp, energy-intensive
treatment, or chemical additives. But that may change. Buckman's Maximyze®
enzymes modify the cellulose in wood to increase the number of "fibrils" that bind
the wood fibers to each other, thus making paper with improved strength and
quality—without additional chemicals or energy. Buckman's process also allows
papermaking with less wood fiber and higher percentages of recycled paper,
enabling a single plant to save $1 million per year.
Center For Green Chemistry
and Green Engineering at Yale
Paper consumption, worldwide
• Paper use increases year after year and
has quadrupled over the past 50 years!
• 2014 – global paper production hit 400
million tons per year (the same year that
atmospheric CO2 levels exceeded 400
parts per million)
• China, USA and Japan: 51%
• China (106 million tons)
• USA (71 million tons)
• Japan (27 million tons),
• Europe: 23% (92 million tons)
• Africa: 2% (8 million tons/year)
• Oceania and Latin America: 8%
Paper consumption per capita by region
Source: State of the Global Paper
Industry, Environmental Paper Network
Center For Green Chemistry
and Green Engineering at Yale
Paper making
• Cellulose fibers are the basic structural material of paper
• Properties of a sheet of paper like strength and weight depend on bonding between
cellulose fibers
• Existing Technology:
• Papermakers can improve paper strength by:
Adding different wood pulps (costly)
Increasing mechanical treatment (requires significant energy expenditure)
Using various chemical additives (many derived from non-renewable resources)
• Buckman technology: utilizes enzymes (cellulases) to strengthen fibers in paper
making and recycling
Center For Green Chemistry
and Green Engineering at Yale
Cellulases
• In nature, cellulases are enzymes that catalyze the hydrolysis of
cellulose to degrade and recycle this organic compound (all
together these enzymes completely recycle cellulose)
• Endoclucanases break internal bonds to disrupt the crystalline
structure of cellulose and expose individual chains
• Exocellulases separate pieces of two to four sugar monomers from
the exposed chains
• Cellobiases (b-glucosidases) hydrolyze those fragments into glucose
• Cellulases in nature hydrolyze and recycle cellulose (the most
common organic compound on earth)
• In paper manufacturing, the goal is to modify cellulose fiber,
not destroy it
• Requires the selection and proper application of specific enzymes
from this group to develop the desired results
Cellulose
Image: Wikimedia Commons
Center For Green Chemistry
and Green Engineering at Yale
Mazimyze® technology for paper production and
recycling
•Approach: Select enzymes within the cellulase group
to modify cellulose fibers in order to improve paper
quality and support greener manufacturing practices.
•Maximyze® technology consists of specific enzymes
that improve inter-fiber bonding in cellulose, resulting
in many benefits:
• A reduction in the amount of wood pulp needed to produce the
paper or paperboard
• An improvement in the quality of the paper or paperboard
• An increase in production rates
• A reduction in energy requirements in manufacture
• An increase in the amount of recycled paper that can be used in
the product
Fibers before and after the
treatment with Maximyze®
Center For Green Chemistry
and Green Engineering at Yale
Greener Benefits
• Reduces the amount of cellulose fiber required: fewer trees needed, improving the strength of the
paper
• Reduces the resources required for shipping: Lighter weight paper
• Allows for the increased use of recovered paper (recycled paper): Improves strength of paper from
recycled fibers, allowing for increase in use of recycled fibers
• Reduces the energy requirements: Less refining of the paper is required
• Requires less steam to dry the paper: Improves water removal in the drying process
• Increases the proportion of hardwood fiber: Softwood fibers are typically required to maintain the
strength needed in paper; these fibers have higher costs
• Reduces volumes in landfills: Lighter weight paper, less material, improves recycling
• Replaces or reduces the use of current chemical products: Glyoxalated polyacrylamides (g-PAM)
and polyacrylamide copolymers are used to improved paper strength; these are not needed with
Maximyze®
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Professor Bruce Lipshutz, University of California,
Santa Barbara
Towards Ending our Dependence on Organic Solvents
2011 Presidential Green Chemistry Challenge Academic Award
Center For Green Chemistry
and Green Engineering at Yale
Professor Bruce Lipshutz, University of California Santa Barbara
Towards Ending Our Dependence on Organic Solvents
Most chemical manufacturing processes rely
on organic solvents, which tend to be volatile,
toxic, and flammable. Chemical manufacturers
use billions of pounds of organic solvents each
year, much of which becomes waste. Water
itself cannot replace organic solvents as the
medium for chemical reactions because many
chemicals do not dissolve and do not react in
water.
Professor Lipshutz has designed a safe
surfactant that forms tiny droplets in water.
Organic chemicals dissolve in these droplets
and react efficiently, allowing water to replace
organic solvents.
reactions take
place here
Images curtesy of Professor Bruce Lipshutz
Center For Green Chemistry
and Green Engineering at Yale
Professor Bruce Lipshutz, University of California Santa
Barbara Towards Ending Our Dependence on Organic Solvents
New Nanomicelles as “Nanoreactors” in Water
Benign by design “designer” surfactants
(available from Aldrich)
Images curtesy of Professor Bruce Lipshutz
Center For Green Chemistry
and Green Engineering at Yale
Professor Bruce Lipshutz, University of California Santa
Barbara Towards Ending Our Dependence on Organic Solvents
Applications of nanomicellar technology
chemistry in water at RT
Images curtesy of Professor Bruce Lipshutz
Center For Green Chemistry
and Green Engineering at Yale
What is a micelle?
Micelle
Hydrophilic
Hydrophobic
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
SiGNa Chemistry, Inc.
2008 Presidential Green Chemistry Challenge Small Business Award
Center For Green Chemistry
and Green Engineering at Yale
SiGNa Chemistry
• Alkali metals and their anhydrides
• Extremely reactive
• Hazardous to use and store
• Uses
• Reducing agents
• Catalysts
• Greener Solution:
• Silica or alumina encapsulated alkali metals (M-SG)
• M-SG reagents are room-temperature stable free-flowing powders that retain
the chemical reactivity of the parent metal, decreasing the danger and
associated cost of using reactive metals.
Center For Green Chemistry
and Green Engineering at Yale
SiGNa Chemistry:
• Alkali metals are absorbed into silica gel to yield loose black powders (M-SG) that are strong reducing agents.
All react nearly quantitatively with water to form hydrogen.
• Types of M-SG
• Air sensitive powders
• Moisture sensitive but not sensitive to dry air.
• Air and moisture ‘stable’ (can be handled in ambient air with only slow degradation by
atmospheric moisture)
• These materials eliminate many hazards associated with pure alkali metals by providing easily handled
reducing agents and hydrogen sources.
• Applications:
• Reduction of esters to alcohols
• Can be used to desulfurize various compounds,
• Reductive protonation of aromatics,
• Dechlorination of alkyl and aryl halides
Center For Green Chemistry
and Green Engineering at Yale
Applications of M-SG
• Reduction of carboxylic acids to alcohols
• M-SG mediated deprotection of protected secondary amines
• Reductive protonation of aromatics
Desulfonation Detosylation
Center For Green Chemistry
and Green Engineering at Yale
Safety demo Na metal vs Na-SG
17
Water Test - Na Metal_500mg Water Test - Stage I Na-SG_1.5g
The catalysts react with water to produce hydrogen in large quantities
The SiGNa chemistry compounds/materials have potential use in fuel cells and
environmental remediation of toxic chemicals.
http://www.signachem.com/resources/
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Archer Daniels Midland and Novozymes,
NovaLipidTM:
2005 Presidential Green Chemistry Challenge Greener Synthetic Pathways
Award
Center For Green Chemistry
and Green Engineering at Yale
ADM and Novozymes
2005 Greener Synthetic Pathways Award
• U.S. FDA requires mandatory labeling of trans fats on nutritional fact panels
(effective January 1, 2006)
• U.S. FDA urging for the reduction of the consumption of trans fats
• Partially hydrogenated vegetable oils is the most common source for trans
fatty acids
Center For Green Chemistry
and Green Engineering at Yale
Why trans fatty acids?
HO
O
trans
HO
O
cis
The presence of the double bonds is responsible for the liquid
properties of native vegetable oil. Because the cis double
bonds are “kinked”, they disrupt the physical interactions
between fatty acid molecules, preventing them from packing
together tightly to form crystals. This disruption keeps the
fatty acid molecules from associating with each other,
resulting in a liquid structure.
If the double bonds are removed by adding hydrogen
(hydrogenation), the kinks are removed, allowing the fatty acid
molecules to more easily associate with each other. The result
is crystallization (solid fat) at room temperature. Most trans
fatty acids are produced through an industrial process that
added hydrogen to vegetable oils to produce partially
hydrogenated vegetable oil.
Center For Green Chemistry
and Green Engineering at Yale
Interesterification (IE) to remove trans fatty acids
R = fully or partially hydrogenated fatty acid
chains (with cis and/or trans bonds)
Traditional processes:
• Alkaline chemical catalyst: sodium
methoxide
• Catalyst generates soaps or salts that
are not easily separated (extra waste
stream generated in washing of the oils)
• Side reactions occur, darkening the oil
and requiring bleaching of the oils to
remove color (spent bleaching clay is an
additional waste stream)
Center For Green Chemistry
and Green Engineering at Yale
Enzymatic Interesterification (IE)
(ADM and Novozyme PGCCA)
R = fully or partially hydrogenated fatty acid
chains (with cis and/or trans bonds)
Enzymatic process:
• Enzyme catalyst (typically not stable
and high cost)
• ADM and Novozyme stabilized the
enzyme to reduce costs and
increase stability
• No use of chemical catalyst and acid
neutralizer
• No generation of by-products (soaps or
salts)
• No generation of waste water
• No generation of solid waste On the market: NovalipidTM - Zero and reduced-trans oils and
shortening products, produced using the enzymatic IE process
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Pfizer, Inc.: Re-design of Sertraline
(ZOLOFT®)
2002 Presidential Green Chemistry Challenge Award
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Product: Sertraline hydrochloride is an inhibitor of synaptosomal serotinin uptake,
used as a pharmaceutical agent for the treatment of depression as well as
dependency and other anxiety related disorders. (ZOLOFT®)
Pfizer won a Presidential Green Chemistry Challenge Award in 2002 for the re-
design of their manufacturing process using the 12 principles of green chemistry.
Center For Green Chemistry
and Green Engineering at Yale
First Commercial
Route to
Sertraline:
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic
Process Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process
Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process
Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
Center For Green Chemistry
and Green Engineering at Yale
• Eliminated use of 140 metric tons/year of
titanium tetrachloride
• Avoided generation of 440 metric tons/year of
solid titanium dioxide waste
• Eliminated generation of over 40 metric
tons/year of trans isomer
• Avoided generation of 150 metric tons/year of
35% HCl waste
• Eliminated need for 100 metric tons/year of 50%
NaOH
• Some aqueous washes
• Dramatically reduced the number and volume of
solvents used
Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Dow Chemical Company:
Designing an Environmentally Safe Marine
Antifoulant
1996 Presidential Green Chemistry Challenge Award
Center For Green Chemistry
and Green Engineering at Yale
Marine fouling
Fouling, the unwanted growth
of plants and animals on a
ship's surface, costs the
shipping industry
approximately $3 billion a year.
A significant portion of this
cost is the increased fuel
consumption needed to
overcome hydrodynamic drag.
Increased fuel consumption
also contributes to pollution,
global warming, and acid rain.
Image: https://libreshot.com/container-ship-freighter/
Center For Green Chemistry
and Green Engineering at Yale
Dow Chemical Company: Designing an
Environmentally Safe Marine Antifoulant
Antifoulants are generally dispersed in the paint as it is applied to the
hull. Organotin compounds have traditionally been used, particularly
tributyltin oxide (TBTO). TBTO works by gradually leaching from the
hull killing the fouling organisms in the surrounding area.
TBTO and other organotin antifoulants have long half-lives in the
environment (half-life of TBTO in seawater is > 6 months). They also
bioconcentrate in marine organisms (the concentration of TBTO in
marine organisms to be 104 times greater than in the surrounding
water).
Organotin compounds are chronically toxic to marine life and can
enter food chain. They are bioaccumulative.
Tributyltin oxide (TBTO)
Center For Green Chemistry
and Green Engineering at Yale
Dow Chemical Company: Designing an
Environmentally Safe Marine Antifoulant
Sea-Nine® 211
http://www.rohmhaas.com/seanine/index.html
Rohm and Haas (now Dow Chemical)
Presidential Green Chemistry Challenge Award,
1996
The active ingredient in Sea-Nine® 211, 4,5-
dichloro-2-n-octyl-4-isothiazolin-3-one
(DCOI), is a member of the isothiazolone family
of antifoulants.
4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOI)
Center For Green Chemistry
and Green Engineering at Yale
International Marine Organization:
What makes a good anti-foulant?
1. Broad spectrum activity
2. Low mammalian toxicity
3. Low water solubility
4. No bioaccumulation in the
food chain
5. Not persistent in the
environment
6. Compatible with paint raw
materials
7. Favorable price/performance
http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf,
Image: https://libreshot.com/container-ship-freighter/
Center For Green Chemistry
and Green Engineering at Yale
International Marine Organization:
What makes a good anti-foulant?
 Broad spectrum activity
• Low mammalian toxicity – toxic to humans
 Low water solubility
• No bioaccumulation in the food chain -
bioaccumulative
• Not persistent in the environment - (1/2 life
in water > 6 months)
 Compatible with paint raw materials
 Favorable price/performance
http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf
 Broad spectrum activity
 Low mammalian toxicity – low acute toxicity
 Low water solubility
 No bioaccumulation in the food chain – not
bioaccumulative
 Not persistent in the environment – (1/2 life in
water < 1 hour)
 Compatible with paint raw materials
 Favorable price/performance
Center For Green Chemistry
and Green Engineering at Yale
Dow Chemical Company: Designing an
Environmentally Safe Marine Antifoulant
• TBTO banned worldwide by the International Marine Organization = use was
phased out by 2008
• European Union: Identified TBTO as a severe marine pollutant and SVHC
(Substance of Very High Concern)
Center For Green Chemistry
and Green Engineering at Yale
Dow Chemical Company: Designing an
Environmentally Safe Marine Antifoulant
Sea-Nine® 211 works by maintaining a hostile growing
environment for marine organisms. When organisms attach
to the hull (treated with DCOI), proteins at the point of
attachment with the hull react with the DCOI. This reaction
with the DCOI prevents the use of these proteins for other
metabolic processes. The organism thus detaches itself and
searches for a more hospitable surface on which to grow.
Only organisms attached to hull of ship are exposed to toxic
levels of DCOI.
Readily biodegrades once leached from ship (half-life is less
than one hour in sea water).
http://msdssearch.dow.com/PublishedLiteratureDO
WCOM/dh_08a4/0901b803808a4d1e.pdf?filepath=
microbial/pdfs/noreg/253-
02760.pdf&fromPage=GetDoc
4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOI)
Center For Green Chemistry
and Green Engineering at Yale
Center For Green Chemistry
and Green Engineering atYale
Real-World Cases in Green Chemistry:
A class exercise
Center For Green Chemistry
and Green Engineering at Yale
Real-World Cases in Green Chemistry
• Students select a Presidential Green Chemistry Challenge Award winner of
interest
• Summarize the “traditional” chemistry, or problem that the award addresses
• Summarize the greener chemistry
• Including the economic and environmental (and human health) benefit
• Create a PowerPoint presentation, report, or poster presentation and present it
back to the class!
Center For Green Chemistry
and Green Engineering at Yale
Summary
• Presidential Green Chemistry Challenge Awards: Case studies for understanding
real-world examples of Green Chemistry technologies
• PGCCA case studies are examples of greener technologies that also have
economic benefits, and work just as good (or better) than traditional
counterparts
• Environmental and human health benefits, economic benefits, and performance benefits are
3 main aspects of green chemistry technologies
• Use the PGCCA’s as examples to learn more about applied Green Chemistry!

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  • 1. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Buckman International, Inc. Enzymes Reduce the Energy and Wood Fiber Required to Manufacture High-Quality Paper and Paperboard 2012 Presidential Green Chemistry Challenge Designing Greener Chemicals Award
  • 2. Center For Green Chemistry and Green Engineering at Yale Buckman International, Inc. Summary: Traditionally, making strong paper required costly wood pulp, energy-intensive treatment, or chemical additives. But that may change. Buckman's Maximyze® enzymes modify the cellulose in wood to increase the number of "fibrils" that bind the wood fibers to each other, thus making paper with improved strength and quality—without additional chemicals or energy. Buckman's process also allows papermaking with less wood fiber and higher percentages of recycled paper, enabling a single plant to save $1 million per year.
  • 3. Center For Green Chemistry and Green Engineering at Yale Paper consumption, worldwide • Paper use increases year after year and has quadrupled over the past 50 years! • 2014 – global paper production hit 400 million tons per year (the same year that atmospheric CO2 levels exceeded 400 parts per million) • China, USA and Japan: 51% • China (106 million tons) • USA (71 million tons) • Japan (27 million tons), • Europe: 23% (92 million tons) • Africa: 2% (8 million tons/year) • Oceania and Latin America: 8% Paper consumption per capita by region Source: State of the Global Paper Industry, Environmental Paper Network
  • 4. Center For Green Chemistry and Green Engineering at Yale Paper making • Cellulose fibers are the basic structural material of paper • Properties of a sheet of paper like strength and weight depend on bonding between cellulose fibers • Existing Technology: • Papermakers can improve paper strength by: Adding different wood pulps (costly) Increasing mechanical treatment (requires significant energy expenditure) Using various chemical additives (many derived from non-renewable resources) • Buckman technology: utilizes enzymes (cellulases) to strengthen fibers in paper making and recycling
  • 5. Center For Green Chemistry and Green Engineering at Yale Cellulases • In nature, cellulases are enzymes that catalyze the hydrolysis of cellulose to degrade and recycle this organic compound (all together these enzymes completely recycle cellulose) • Endoclucanases break internal bonds to disrupt the crystalline structure of cellulose and expose individual chains • Exocellulases separate pieces of two to four sugar monomers from the exposed chains • Cellobiases (b-glucosidases) hydrolyze those fragments into glucose • Cellulases in nature hydrolyze and recycle cellulose (the most common organic compound on earth) • In paper manufacturing, the goal is to modify cellulose fiber, not destroy it • Requires the selection and proper application of specific enzymes from this group to develop the desired results Cellulose Image: Wikimedia Commons
  • 6. Center For Green Chemistry and Green Engineering at Yale Mazimyze® technology for paper production and recycling •Approach: Select enzymes within the cellulase group to modify cellulose fibers in order to improve paper quality and support greener manufacturing practices. •Maximyze® technology consists of specific enzymes that improve inter-fiber bonding in cellulose, resulting in many benefits: • A reduction in the amount of wood pulp needed to produce the paper or paperboard • An improvement in the quality of the paper or paperboard • An increase in production rates • A reduction in energy requirements in manufacture • An increase in the amount of recycled paper that can be used in the product Fibers before and after the treatment with Maximyze®
  • 7. Center For Green Chemistry and Green Engineering at Yale Greener Benefits • Reduces the amount of cellulose fiber required: fewer trees needed, improving the strength of the paper • Reduces the resources required for shipping: Lighter weight paper • Allows for the increased use of recovered paper (recycled paper): Improves strength of paper from recycled fibers, allowing for increase in use of recycled fibers • Reduces the energy requirements: Less refining of the paper is required • Requires less steam to dry the paper: Improves water removal in the drying process • Increases the proportion of hardwood fiber: Softwood fibers are typically required to maintain the strength needed in paper; these fibers have higher costs • Reduces volumes in landfills: Lighter weight paper, less material, improves recycling • Replaces or reduces the use of current chemical products: Glyoxalated polyacrylamides (g-PAM) and polyacrylamide copolymers are used to improved paper strength; these are not needed with Maximyze®
  • 8. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Professor Bruce Lipshutz, University of California, Santa Barbara Towards Ending our Dependence on Organic Solvents 2011 Presidential Green Chemistry Challenge Academic Award
  • 9. Center For Green Chemistry and Green Engineering at Yale Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents Most chemical manufacturing processes rely on organic solvents, which tend to be volatile, toxic, and flammable. Chemical manufacturers use billions of pounds of organic solvents each year, much of which becomes waste. Water itself cannot replace organic solvents as the medium for chemical reactions because many chemicals do not dissolve and do not react in water. Professor Lipshutz has designed a safe surfactant that forms tiny droplets in water. Organic chemicals dissolve in these droplets and react efficiently, allowing water to replace organic solvents. reactions take place here Images curtesy of Professor Bruce Lipshutz
  • 10. Center For Green Chemistry and Green Engineering at Yale Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents New Nanomicelles as “Nanoreactors” in Water Benign by design “designer” surfactants (available from Aldrich) Images curtesy of Professor Bruce Lipshutz
  • 11. Center For Green Chemistry and Green Engineering at Yale Professor Bruce Lipshutz, University of California Santa Barbara Towards Ending Our Dependence on Organic Solvents Applications of nanomicellar technology chemistry in water at RT Images curtesy of Professor Bruce Lipshutz
  • 12. Center For Green Chemistry and Green Engineering at Yale What is a micelle? Micelle Hydrophilic Hydrophobic
  • 13. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale SiGNa Chemistry, Inc. 2008 Presidential Green Chemistry Challenge Small Business Award
  • 14. Center For Green Chemistry and Green Engineering at Yale SiGNa Chemistry • Alkali metals and their anhydrides • Extremely reactive • Hazardous to use and store • Uses • Reducing agents • Catalysts • Greener Solution: • Silica or alumina encapsulated alkali metals (M-SG) • M-SG reagents are room-temperature stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.
  • 15. Center For Green Chemistry and Green Engineering at Yale SiGNa Chemistry: • Alkali metals are absorbed into silica gel to yield loose black powders (M-SG) that are strong reducing agents. All react nearly quantitatively with water to form hydrogen. • Types of M-SG • Air sensitive powders • Moisture sensitive but not sensitive to dry air. • Air and moisture ‘stable’ (can be handled in ambient air with only slow degradation by atmospheric moisture) • These materials eliminate many hazards associated with pure alkali metals by providing easily handled reducing agents and hydrogen sources. • Applications: • Reduction of esters to alcohols • Can be used to desulfurize various compounds, • Reductive protonation of aromatics, • Dechlorination of alkyl and aryl halides
  • 16. Center For Green Chemistry and Green Engineering at Yale Applications of M-SG • Reduction of carboxylic acids to alcohols • M-SG mediated deprotection of protected secondary amines • Reductive protonation of aromatics Desulfonation Detosylation
  • 17. Center For Green Chemistry and Green Engineering at Yale Safety demo Na metal vs Na-SG 17 Water Test - Na Metal_500mg Water Test - Stage I Na-SG_1.5g The catalysts react with water to produce hydrogen in large quantities The SiGNa chemistry compounds/materials have potential use in fuel cells and environmental remediation of toxic chemicals. http://www.signachem.com/resources/
  • 18. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Archer Daniels Midland and Novozymes, NovaLipidTM: 2005 Presidential Green Chemistry Challenge Greener Synthetic Pathways Award
  • 19. Center For Green Chemistry and Green Engineering at Yale ADM and Novozymes 2005 Greener Synthetic Pathways Award • U.S. FDA requires mandatory labeling of trans fats on nutritional fact panels (effective January 1, 2006) • U.S. FDA urging for the reduction of the consumption of trans fats • Partially hydrogenated vegetable oils is the most common source for trans fatty acids
  • 20. Center For Green Chemistry and Green Engineering at Yale Why trans fatty acids? HO O trans HO O cis The presence of the double bonds is responsible for the liquid properties of native vegetable oil. Because the cis double bonds are “kinked”, they disrupt the physical interactions between fatty acid molecules, preventing them from packing together tightly to form crystals. This disruption keeps the fatty acid molecules from associating with each other, resulting in a liquid structure. If the double bonds are removed by adding hydrogen (hydrogenation), the kinks are removed, allowing the fatty acid molecules to more easily associate with each other. The result is crystallization (solid fat) at room temperature. Most trans fatty acids are produced through an industrial process that added hydrogen to vegetable oils to produce partially hydrogenated vegetable oil.
  • 21. Center For Green Chemistry and Green Engineering at Yale Interesterification (IE) to remove trans fatty acids R = fully or partially hydrogenated fatty acid chains (with cis and/or trans bonds) Traditional processes: • Alkaline chemical catalyst: sodium methoxide • Catalyst generates soaps or salts that are not easily separated (extra waste stream generated in washing of the oils) • Side reactions occur, darkening the oil and requiring bleaching of the oils to remove color (spent bleaching clay is an additional waste stream)
  • 22. Center For Green Chemistry and Green Engineering at Yale Enzymatic Interesterification (IE) (ADM and Novozyme PGCCA) R = fully or partially hydrogenated fatty acid chains (with cis and/or trans bonds) Enzymatic process: • Enzyme catalyst (typically not stable and high cost) • ADM and Novozyme stabilized the enzyme to reduce costs and increase stability • No use of chemical catalyst and acid neutralizer • No generation of by-products (soaps or salts) • No generation of waste water • No generation of solid waste On the market: NovalipidTM - Zero and reduced-trans oils and shortening products, produced using the enzymatic IE process
  • 23. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) 2002 Presidential Green Chemistry Challenge Award
  • 24. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Product: Sertraline hydrochloride is an inhibitor of synaptosomal serotinin uptake, used as a pharmaceutical agent for the treatment of depression as well as dependency and other anxiety related disorders. (ZOLOFT®) Pfizer won a Presidential Green Chemistry Challenge Award in 2002 for the re- design of their manufacturing process using the 12 principles of green chemistry.
  • 25. Center For Green Chemistry and Green Engineering at Yale First Commercial Route to Sertraline: Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 26. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 27. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 28. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 29. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 30. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 31. Center For Green Chemistry and Green Engineering at Yale Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  • 32. Center For Green Chemistry and Green Engineering at Yale • Eliminated use of 140 metric tons/year of titanium tetrachloride • Avoided generation of 440 metric tons/year of solid titanium dioxide waste • Eliminated generation of over 40 metric tons/year of trans isomer • Avoided generation of 150 metric tons/year of 35% HCl waste • Eliminated need for 100 metric tons/year of 50% NaOH • Some aqueous washes • Dramatically reduced the number and volume of solvents used Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Pfizer, Inc.: Re-design of Sertraline (ZOLOFT®)
  • 33. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Dow Chemical Company: Designing an Environmentally Safe Marine Antifoulant 1996 Presidential Green Chemistry Challenge Award
  • 34. Center For Green Chemistry and Green Engineering at Yale Marine fouling Fouling, the unwanted growth of plants and animals on a ship's surface, costs the shipping industry approximately $3 billion a year. A significant portion of this cost is the increased fuel consumption needed to overcome hydrodynamic drag. Increased fuel consumption also contributes to pollution, global warming, and acid rain. Image: https://libreshot.com/container-ship-freighter/
  • 35. Center For Green Chemistry and Green Engineering at Yale Dow Chemical Company: Designing an Environmentally Safe Marine Antifoulant Antifoulants are generally dispersed in the paint as it is applied to the hull. Organotin compounds have traditionally been used, particularly tributyltin oxide (TBTO). TBTO works by gradually leaching from the hull killing the fouling organisms in the surrounding area. TBTO and other organotin antifoulants have long half-lives in the environment (half-life of TBTO in seawater is > 6 months). They also bioconcentrate in marine organisms (the concentration of TBTO in marine organisms to be 104 times greater than in the surrounding water). Organotin compounds are chronically toxic to marine life and can enter food chain. They are bioaccumulative. Tributyltin oxide (TBTO)
  • 36. Center For Green Chemistry and Green Engineering at Yale Dow Chemical Company: Designing an Environmentally Safe Marine Antifoulant Sea-Nine® 211 http://www.rohmhaas.com/seanine/index.html Rohm and Haas (now Dow Chemical) Presidential Green Chemistry Challenge Award, 1996 The active ingredient in Sea-Nine® 211, 4,5- dichloro-2-n-octyl-4-isothiazolin-3-one (DCOI), is a member of the isothiazolone family of antifoulants. 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOI)
  • 37. Center For Green Chemistry and Green Engineering at Yale International Marine Organization: What makes a good anti-foulant? 1. Broad spectrum activity 2. Low mammalian toxicity 3. Low water solubility 4. No bioaccumulation in the food chain 5. Not persistent in the environment 6. Compatible with paint raw materials 7. Favorable price/performance http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf, Image: https://libreshot.com/container-ship-freighter/
  • 38. Center For Green Chemistry and Green Engineering at Yale International Marine Organization: What makes a good anti-foulant?  Broad spectrum activity • Low mammalian toxicity – toxic to humans  Low water solubility • No bioaccumulation in the food chain - bioaccumulative • Not persistent in the environment - (1/2 life in water > 6 months)  Compatible with paint raw materials  Favorable price/performance http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf  Broad spectrum activity  Low mammalian toxicity – low acute toxicity  Low water solubility  No bioaccumulation in the food chain – not bioaccumulative  Not persistent in the environment – (1/2 life in water < 1 hour)  Compatible with paint raw materials  Favorable price/performance
  • 39. Center For Green Chemistry and Green Engineering at Yale Dow Chemical Company: Designing an Environmentally Safe Marine Antifoulant • TBTO banned worldwide by the International Marine Organization = use was phased out by 2008 • European Union: Identified TBTO as a severe marine pollutant and SVHC (Substance of Very High Concern)
  • 40. Center For Green Chemistry and Green Engineering at Yale Dow Chemical Company: Designing an Environmentally Safe Marine Antifoulant Sea-Nine® 211 works by maintaining a hostile growing environment for marine organisms. When organisms attach to the hull (treated with DCOI), proteins at the point of attachment with the hull react with the DCOI. This reaction with the DCOI prevents the use of these proteins for other metabolic processes. The organism thus detaches itself and searches for a more hospitable surface on which to grow. Only organisms attached to hull of ship are exposed to toxic levels of DCOI. Readily biodegrades once leached from ship (half-life is less than one hour in sea water). http://msdssearch.dow.com/PublishedLiteratureDO WCOM/dh_08a4/0901b803808a4d1e.pdf?filepath= microbial/pdfs/noreg/253- 02760.pdf&fromPage=GetDoc 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (DCOI)
  • 41. Center For Green Chemistry and Green Engineering at Yale Center For Green Chemistry and Green Engineering atYale Real-World Cases in Green Chemistry: A class exercise
  • 42. Center For Green Chemistry and Green Engineering at Yale Real-World Cases in Green Chemistry • Students select a Presidential Green Chemistry Challenge Award winner of interest • Summarize the “traditional” chemistry, or problem that the award addresses • Summarize the greener chemistry • Including the economic and environmental (and human health) benefit • Create a PowerPoint presentation, report, or poster presentation and present it back to the class!
  • 43. Center For Green Chemistry and Green Engineering at Yale Summary • Presidential Green Chemistry Challenge Awards: Case studies for understanding real-world examples of Green Chemistry technologies • PGCCA case studies are examples of greener technologies that also have economic benefits, and work just as good (or better) than traditional counterparts • Environmental and human health benefits, economic benefits, and performance benefits are 3 main aspects of green chemistry technologies • Use the PGCCA’s as examples to learn more about applied Green Chemistry!

Editor's Notes

  1. Readings: Pulp & Paper International, November 2012: https://www.buckman.com/wp-content/uploads/2018/04/PPI-2012-Greener-Pckg.pdf Buckman Maximyze enzyme video: https://www.youtube.com/watch?v=42H7SsCX7zI June 18, 2012: Buckman Wins Presidential Green Chemistry Challenge Award article: https://www.buckman.com/news/buckman-wins-presidential-green-chemistry-challenge-award/
  2. Full summary and description of award winning technology can be found here: https://www.epa.gov/greenchemistry/presidential-green-chemistry-challenge-2012-designing-greener-chemicals-award
  3. Source: State of the Global Paper Industry, Environmental Paper Network, http://environmentalpaper.org/wp-content/uploads/2018/04/StateOfTheGlobalPaperIndustry2018_FullReport-Final-1.pdf If you look at a per capita basis on these numbers: Exploration of per capita consumption figures reveals a more nuanced story. The global average is 55 kg per person per year. North American consumption is four times that (215 kg) while the African average is just 7 kg. China’s average per capita consumption is just higher than the global average at 76 kg. Eastern European levels are similar to China’s (77 kg) with the Western European average being almost double that (147 kg). Seven of the ten countries with the largest per capita consumption are in Europe. Paper consumption is at unsustainable levels and globally it is steadily increasing, particularly in Asia, while remaining at unequal levels of access in some parts of the world, particularly Africa. Increasing production in response to new market demand is driving development of new virgin-fibre pulp mills, especially in Asia, Africa and South America. Expansion is resulting in numerous social conflicts in many nations including Brazil, Indonesia, Canada, India, Chile and Mozambique. The industry has substantial climate change impacts and critical opportunities for reducing greenhouse gas emissions through better land management and fibre choices need to be seized, urgently. Corporate social responsibility commitments and purchasing policies have continued to proliferate and have helped to drive some specific social and environmental improvements ‘on-the-ground,’ but execution, transparency and progress on many voluntary commitments is lagging.
  4. Wikimedia Commons image file: http://commons.wikimedia.org/wiki/File:Cellulose_strand.jpg
  5. Image from: https://www.buckman.com/innovation/maximyze-for-packaging/ And, from the Presidential Green Chemistry Challenge Award Nomination package. YouTube video of technology: https://www.youtube.com/watch?time_continue=2&v=42H7SsCX7zI
  6. From: Presidential Green Chemistry Challenge Award Application Benefits - Here is a summary of benefits of this technology in real-world applications (details follow in specific case studies given later in this document).  - First, improving the strength of a paper product allows reducing the amount of cellulose fiber required to attain the required specifications. The basis weight of the paper can be reduced, so less fiber (i.e. fewer trees) is required to create the same product. In addition to the environmental benefit, the primary cost for manufacture of a paper product is the fiber raw material; so this provides a significant economic benefit to the manufacturer.  - Another economic and environmental benefit relates to transport of the end paper product: a lighter weight paper or board translates into reduced resources required for shipping.  - One problem with recycled paper is that there is a loss of strength when paper is made from recycled fiber. The enzymatic action of Maximyze products improves the strength of paper made from recycled fibers, and allows a papermaker to use more recovered paper.  - Next, less refining is required. Refining is a mechanical treatment unique to paper making. This is an energy-intensive process that collapses the fiber and modifies its surface to improve inter-fiber bonding. In Maximyze applications, modifying fibers by enzymatic treatment allows significant reduction in energy requirements for refining, up to complete elimination.  - The combination of enzyme action and reduced refining results in fewer fiber fragments and fines, which improves water removal in the papermaking process so less steam is required to dry the paper on the paper machine.  Often addition of softwood fiber is required to maintain the strength needed in paper. Maximyze allows an increase in the proportion of hardwood fiber. To the papermaker this reduces cost (softwood fibers have a higher cost). We can regard the use of hardwoods for pulp to have fewer deleterious environmental effects. For example, Eucalyptus plantations supply cellulose fiber much more quickly, requiring less forest land compared to softwoods.  - Most paper is recycled, but the use of lighter-weight paper might have an effect of reducing volumes in landfills.  - This focus area involves designing and implementing chemical products that are less hazardous than the products or technologies they replace. Maximyze can replace or reduce the use of current chemical products used for improving paper strength. These include synthetic chemicals like glyoxalated polyacrylamides (g-PAM) and polyacrylamide copolymers which require the use of more toxic materials sourced at least in part from petroleum-based raw materials. Related to this is the incredible efficiency of enzymes. One enzyme can catalyze as many as 40 million conversions in a second, so a very small amount of Maximyze is required. Table 1 compares the enzymatic technology with conventional g-PAM chemistry, showing that the amount of additive required with the enzyme is a small fraction of the g-PAM required. 
  7. For additional information and readings: Lipshutz, B., Current Opinion in Green and Sustainable Chemistry, 2018, 11: 1-8 Lipshutz, B., J. Org. Chem., 2017, 82, 2806-2816 Lipshutz, B., ACS Sustainable Chem. Eng., 2016, 4, 5838 - 5849
  8. More resources and readings, along with videos on SiGNa technologies can be found here: http://www.signachem.com/resources/?fwp_languages=english&fwp_categories=videos
  9. Watch the video demonstrations of sodium metal versus the SiGNa chemistry – each of the pictures are hyperlinked to the videos above, available through the SiGNa Chemistry website.
  10. Most of the carbon-carbon bonds in fats are single bonds, which allow the carbons to freely rotate, making the attached groups chemically identical. However, the number of unsaturated bonds (double bonds) may vary from one to many in the hydrocarbon part of the fatty acid. Since double bonds do not allow free rotation between the attached carbons, any attached chemical groups are fixed in their respective positions. There are two possible orientations for groups attached to the carbons in a double bond. If they are on the same side of the double bond (close together), they are in the cis conformation. The opposite of the cis conformation is the trans conformation, where the residues at ends of the double bond are farther apart. Double bonds in natural vegetable oils and in animal fats are mostly in the cis conformation; however, a few exceptions are known where the trans conformation is present. The presence of the double bonds is responsible for the liquid properties of native vegetable oil. Because the cis double bonds are “kinked”, they disrupt the physical interactions between fatty acid molecules, preventing them from packing together tightly to form crystals. This disruption keeps the fatty acid molecules from associating with each other, resulting in a liquid structure. If the double bonds are removed by adding hydrogen (hydrogenation), the kinks are removed, allowing the fatty acid molecules to more easily associate with each other. The result is crystallization (solid fat) at room temperature. The presence of the double bonds is responsible for the liquid properties of native vegetable oil. Because the cis double bonds are “kinked”, they disrupt the physical interactions between fatty acid molecules, preventing them from packing together tightly to form crystals. This disruption keeps the fatty acid molecules from associating with each other, resulting in a liquid structure. If the double bonds are removed by adding hydrogen (hydrogenation), the kinks are removed, allowing the fatty acid molecules to more easily associate with each other. The result is crystallization (solid fat) at room temperature. Most trans fatty acids are produced through an industrial process that added hydrogen to vegetable oils to produce partially hydrogenated vegetable oil. https://www.mayoclinic.org/diseases-conditions/high-blood-cholesterol/in-depth/trans-fat/art-20046114 - for info about trans fats and health effects
  11. Additional information – see the full nomination package from ADM and Novozyme
  12. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Sertraline (Pfizer) is the active ingredient in Zoloft, the most widely prescribed antidepressant drug. The development and manufacture of Zoloft began with the “discovery” of how the Sertraline structure could be made in the laboratory. The first commercial manufacturing route for making Sertraline involved the use of hazardous chemicals such as toluene, hexane and tetrahydrofuran. This route involved the use of 140 metric tons of titanium tetrachloride, which resulted in the formation of 440 metric tons of solid titanium dioxide waste per year. 150 metric tons/year of 35% hydrochloric acid waste was generated and there was a need for 100 metric tons/year of 50% sodium hydroxide.   Scientists at Pfizer, Inc. re-designed the production process of Sertraline using the twelve principles of green chemistry and were able to completely eliminate the requirement for titanium tetrachloride, resulting in the elimination of the aqueous titanium dioxide waste stream. The re-design of the process also allowed for the elimination of the use of hexane, toluene and tetrahydrofuran. The new process produces 26 Liters of solvent waste per kilogram of product (Sertraline), compared to the first commercial route of 98 Liters per kilogram. It should be noted that the product, Zoloft, remains the same high purity and activity. Therefore, despite the change in process, the product is just as good.
  13. This is the first commercial route to Sertraline – for this example we will focus on the last 4 steps and compare to the Current Commercial Route to Sertraline. The first commercial synthesis of sertraline hydrochlorde involves a condensation reaction of the tetralone (2) with excess of monomethylamine, which is catalyzed by titanium tetrachloride to form the imine (3). The reduction of 3 produces the racemic syn- and anti-diastereomers of the amine. The desired syn-amine is then selectively crystallized and resolved to produce 4 as the D-(-)-mandelic acid salt.   Drawbacks: Uses undesirable reagents and/or produces hazardous byproducts. Control and safe handling of these reagents, including the removal of their byproducts, result in time-consuming operations that affect the efficiency of the commercial process. Titanium tetrachloride: safety concerns (extreme reactivity with water) By-products produced: titanium dioxide and monomethylamine hydrochloride) Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388
  14. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Talking points: Use of TiCl4 in step 2 produces lots of TiO2 waste Step 2: toluene, hexanes, THF … the best solvents? TiCl4 is used to take out water, what other ways can you remove the water?
  15. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Talking points: Step 3, catalyst not too selective
  16. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Talking points: How many molecules are isolated? Each time a molecule is isolated, what needs to happen (crystallization, purification, exposure to workers, etc.)
  17. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 New Commercial Route to Sertraline Talking points: Step 2 eliminated use of TiCl4 (nasty stuff & get rid of TiO2 waste) Step 2 & 3, better solvent used
  18. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Talking points: Step 3, more selective catalyst, better ratio of cis/trans Step 2 & 3, better solvent used
  19. Taber, G.P., Pfisterer, D.M., and Colberg, J., Organic Process Research & Development, 2004, 8, 385-388 Talking points: How many molecules are isolated? 3 vs. 5 in scheme 2 The New Commercial Synthesis: Improvements: Improved safety (eliminate use of TiCl4), improved productivity (eliminating need to filter byproducts – which can be time consuming due to small particle size obtained from two byproducts)   Process: Ethanol used for solvent for telescoping of two steps (not isolating) to increase conversion (99%) significantly and also reduce formation of byproducts. Switch to ethanol for solvent, relying on the low-solubility of 3 in alkanol solvents to drive the reaction to equilibrium to the final product. Conversion from 3 to 6 improved significantly by finding a more selective catalyst (through a design of experiments approach) (Pd/CaCO3, 1% w/w to 2) for the cis isomer. The catalyst not only improved the cis/trans ratio, but also resulted in lower levels of contaminating mono and deschloro impurities.
  20. Additional resources: Michael Cann’s educational modules: http://www.scranton.edu/faculty/cannm/green-chemistry/english/environmental.shtml
  21. Photo from: https://libreshot.com/container-ship-freighter/ - free download
  22. Fouling, the unwanted growth of plants and animals on a ship's surface, costs the shipping industry approximately $3 billion a year. A significant portion of this cost is the increased fuel consumption needed to overcome hydrodynamic drag. Increased fuel consumption also contributes to pollution, global warming, and acid rain. The main compounds used worldwide to control fouling are the organotin antifoulants, such as tributyltin oxide (TBTO). They are effective at preventing fouling, but have widespread environmental problems due to their persistence in the environment and the toxic effects they cause, including acute toxicity, bioaccumulation, decreased reproductive viability, and increased shell thickness in shellfish. These harmful effects led to an EPA special review of organotin antifoulants and to the Organotin Antifoulant Paint Control Act of 1988. This act mandated restrictions on the use of tin in the United States and charged the EPA and the U.S. Navy with conducting research on alternatives to organotins. Based on the need for new antifoulants, Rohm and Haas Company began to search for an environmentally safe alternative to organotin compounds. The ideal antifoulant would prevent fouling from a wide variety of marine organisms without causing harm to non-target organisms. Compounds from the 3-isothiazolone class were chosen as likely candidates and over 140 were screened for antifouling activity in laboratory and field tests. The 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (Sea-Nine™ antifoulant) was chosen as the candidate for commercial development. Extensive environmental testing was done comparing Sea-Nine™ antifoulant to TBTO, the current industry standard. Sea-Nine™ antifoulant degraded extremely rapidly with a half life of one day in seawater and one hour in sediment. TBTO, on the other hand, degraded much more slowly, with a half life in seawater of nine days and six to nine months in sediment. Tin bioaccumulated, with bioaccumulation factors as high as 10,000 X, while Sea-Nine™ antifoulant's bioaccumulation was essentially zero. Both TBTO and Sea-Nine™ were acutely toxic to marine organisms, but TBTO had widespread chronic toxicity, while Sea-Nine™ antifoulant showed no chronic toxicity. Thus the maximum allowable environmental concentration (MAEC) for Sea-Nine™ antifoulant was 0.63 parts per billion (ppb) while the MAEC for TBTO was 0.002 ppb. Sea-Nine™ antifoulant has been sold world-wide and hundreds of ships have been painted with coatings containing it. Rohm and Haas Company obtained EPA registration for the use of Sea-Nine™ antifoulant, the first new antifoulant registration in over a decade
  23. Fouling, the unwanted growth of plants and animals on a ship's surface, costs the shipping industry approximately $3 billion a year. A significant portion of this cost is the increased fuel consumption needed to overcome hydrodynamic drag. Increased fuel consumption also contributes to pollution, global warming, and acid rain. The main compounds used worldwide to control fouling are the organotin antifoulants, such as tributyltin oxide (TBTO). They are effective at preventing fouling, but have widespread environmental problems due to their persistence in the environment and the toxic effects they cause, including acute toxicity, bioaccumulation, decreased reproductive viability, and increased shell thickness in shellfish. These harmful effects led to an EPA special review of organotin antifoulants and to the Organotin Antifoulant Paint Control Act of 1988. This act mandated restrictions on the use of tin in the United States and charged the EPA and the U.S. Navy with conducting research on alternatives to organotins. Based on the need for new antifoulants, Rohm and Haas Company began to search for an environmentally safe alternative to organotin compounds. The ideal antifoulant would prevent fouling from a wide variety of marine organisms without causing harm to non-target organisms. Compounds from the 3-isothiazolone class were chosen as likely candidates and over 140 were screened for antifouling activity in laboratory and field tests. The 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (Sea-Nine™ antifoulant) was chosen as the candidate for commercial development. Extensive environmental testing was done comparing Sea-Nine™ antifoulant to TBTO, the current industry standard. Sea-Nine™ antifoulant degraded extremely rapidly with a half life of one day in seawater and one hour in sediment. TBTO, on the other hand, degraded much more slowly, with a half life in seawater of nine days and six to nine months in sediment. Tin bioaccumulated, with bioaccumulation factors as high as 10,000 X, while Sea-Nine™ antifoulant's bioaccumulation was essentially zero. Both TBTO and Sea-Nine™ were acutely toxic to marine organisms, but TBTO had widespread chronic toxicity, while Sea-Nine™ antifoulant showed no chronic toxicity. Thus the maximum allowable environmental concentration (MAEC) for Sea-Nine™ antifoulant was 0.63 parts per billion (ppb) while the MAEC for TBTO was 0.002 ppb. Sea-Nine™ antifoulant has been sold world-wide and hundreds of ships have been painted with coatings containing it. Rohm and Haas Company obtained EPA registration for the use of Sea-Nine™ antifoulant, the first new antifoulant registration in over a decade
  24. SVHC = substance of very high concern Links for more info: International Marine Organization: http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf Photo from: https://libreshot.com/container-ship-freighter/ - free download
  25. SVHC = substance of very high concern Links for more info: International Marine Organiztaion: http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf
  26. SVHC = substance of very high concern Links for more info: International Marine Organiztaion: http://www.imo.org/en/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf
  27. Fouling, the unwanted growth of plants and animals on a ship's surface, costs the shipping industry approximately $3 billion a year. A significant portion of this cost is the increased fuel consumption needed to overcome hydrodynamic drag. Increased fuel consumption also contributes to pollution, global warming, and acid rain. The main compounds used worldwide to control fouling are the organotin antifoulants, such as tributyltin oxide (TBTO). They are effective at preventing fouling, but have widespread environmental problems due to their persistence in the environment and the toxic effects they cause, including acute toxicity, bioaccumulation, decreased reproductive viability, and increased shell thickness in shellfish. These harmful effects led to an EPA special review of organotin antifoulants and to the Organotin Antifoulant Paint Control Act of 1988. This act mandated restrictions on the use of tin in the United States and charged the EPA and the U.S. Navy with conducting research on alternatives to organotins. Based on the need for new antifoulants, Rohm and Haas Company began to search for an environmentally safe alternative to organotin compounds. The ideal antifoulant would prevent fouling from a wide variety of marine organisms without causing harm to non-target organisms. Compounds from the 3-isothiazolone class were chosen as likely candidates and over 140 were screened for antifouling activity in laboratory and field tests. The 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (Sea-Nine™ antifoulant) was chosen as the candidate for commercial development. Extensive environmental testing was done comparing Sea-Nine™ antifoulant to TBTO, the current industry standard. Sea-Nine™ antifoulant degraded extremely rapidly with a half life of one day in seawater and one hour in sediment. TBTO, on the other hand, degraded much more slowly, with a half life in seawater of nine days and six to nine months in sediment. Tin bioaccumulated, with bioaccumulation factors as high as 10,000 X, while Sea-Nine™ antifoulant's bioaccumulation was essentially zero. Both TBTO and Sea-Nine™ were acutely toxic to marine organisms, but TBTO had widespread chronic toxicity, while Sea-Nine™ antifoulant showed no chronic toxicity. Thus the maximum allowable environmental concentration (MAEC) for Sea-Nine™ antifoulant was 0.63 parts per billion (ppb) while the MAEC for TBTO was 0.002 ppb. Sea-Nine™ antifoulant has been sold world-wide and hundreds of ships have been painted with coatings containing it. Rohm and Haas Company obtained EPA registration for the use of Sea-Nine™ antifoulant, the first new antifoulant registration in over a decade
  28. See the MS Word exercise named “RWCGC Exercise” And, use the 8 PGCCA nomination packages that are supplied