&EPA
United States
Environmental
Protection
Agency
Presidential
Green Chemistry Challenge
Awards Program:
Summary of 2014 Award
Entries and Recipients
An electronic version of this document is available at:
http://www.epa.gov/greenchemistry
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of
Contents
Introduction [[[1
Awards [[[3
Academic Award. ........................................... 3
Small Business Award. 4
Greener Synthetic Pathways Award 5
Greener Reaction Conditions Award 6
Designing Greener Chemicals Award 7
Entries from Academia ............................................9
Entries from Small Businesses ..................................... 15
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Introduction
Each year chemists, engineers, and other scientists from across the United States nominate
their technologies for a Presidential Green Chemistry Challenge Award. This prestigious award
highlights and honors innovative green chemistry technologies, including cleaner processes; safer
raw materials; and safer, better products. These awards recognize and promote the environmental
and economic benefits of developing and using novel green chemistry.
The U.S. Environmental Protection Agency (EPA) celebrates this year's innovative, award-
winning technologies selected from among scores of high-quality nominations. Each nomination
must represent one or more recently developed chemistry technologies that prevent pollution
through source reduction. Nominated technologies are also meant to succeed in the marketplace:
each is expected to illustrate the technical feasibility marketability and profitability of green
chemistry.
Throughout the 19 years of the awards program, EPA has received 1,606 nominations and
presented awards to 98 winners. By recognizing groundbreaking scientific solutions to real-world
environmental problems, the Presidential Green Chemistry Challenge has significantly reduced
the hazards associated with designing, manufacturing, and using chemicals.
Each year our 98 winning technologies are together responsible for:
• Reducing the use or generation of 826 million pounds of hazardous chemicals
• Saving 21 billion gallons of water
• Eliminating 7.8 billion pounds of carbon dioxide releases to air
And adding the benefits from the nominated technologies would greatly increase the program's
total benefits.
This booklet summarizes entries submitted for the 2014 awrards that fell within the scope of
the program. An independent panel of technical experts convened by the American Chemical
Society Green Chemistry Institute'*' judged the entries for the 2014 awrards. Judging criteria
included health and environmental benefits, scientific innovation, and industrial applicability.
Five of the nominated technologies were selected as winners and were nationally recognized on
October 16, 2014, at an awards ceremony in Washington, D.C.
Further information about the Presidential Green Chemistry Challenge Awards and EPA's
Green Chemistry Program is available at www.epa.gov/greenchemistry.
Note: The abstracts in this document were submitted in nominations for the 2014 Presidential Green Chemistry Challenge Awards.
They were copied directly from the nominations and have only been edited for stylistic consistency. They are not written or officially
endorsed by the Agency. These abstracts represent only a fraction of the information provided in the nominations from which they
were copied; judging was conducted on all information in the nominations. Claims made in these abstracts have not been verified
by EPA. Mention of trade names, products, or services does not convey official EPA approval, endorsement, or recommendation.
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Aerobic Oxidation Methods for Pharmaceutical Synthesis
Innovation and Benefits
Oxidation reactions are widely used in the production of organic chemicals, but they often
form wasteful byproducts. Professor Stahl has developed catalytic methods that replace
hazardous chemicals with oxygen from air as an environmentally benign oxidant. The
methods operate under mild conditions, can be performed safely on a large scale, and are
highly selective, even with complex building blocks for pharmaceuticals, potentially saving
time and money and reducing hazardous waste.
Molecular oxygen (O'i) is the least expensive and most environmentally benign chemical
oxidant available, but it is rarely used because of safety concerns and poor reaction selectivity.
Rather than using oxygen, industrial chemists typically choose between using more toxic oxidizing
agents or employing alternative synthetic routes that avoid oxidation altogether, even if the routes
are less efficient.
Professor Stahl and his group specialize in the development and investigation of catalytic
aerobic oxidation reactions, and they recently developed several practical and synthetically useful
aerobic alcohol oxidation methods. In 2011, post-doctoral researcher Dr. Jessica Hoover showed
that a coppcr(I) salt and TEMPO (2,2,6,6-tctramcthylpipcridinyl-N-oxyl) mediate selective
oxidation of primary alcohols to aldehydes at room temperature with ambient air as the oxidant.
The method is compatible with both activated and unactivated alcohols, tolerates heterocycles
and diverse oxygen-, nitrogen-, and sulfur-containing functional groups, and enables selective
oxidation of primary alcohols within the molecules containing unprotected secondary alcohols.
Mechanistic studies of these reactions led to the subsequent discovery of a new catalyst system by
graduate student Janelle Steves that exhibits broader scope and efficiently oxidizes both primary
and secondary alcohols. The simplicity of these catalyst systems and lack of stoichiometric
reagents other than oxygen greatly simplifies product isolation and reduces waste. Chlorinated
solvents, which are commonly needed with other classes of oxidation reactions, are not required.
Professor Stahl has partnered with Professor Thatcher Root (Dept. of Chemical and Biological
Engineering, University ofWisconsin-Madison) and scientists at several pharmaceutical companies
(Drs. Matthew Yatcs, Martin Johnson, Joseph Martinclli at Eli Lilly; Dr. Christopher Welch at
Merck; Dr. Joel Hawkins at Pfizer) to explore strategies for safe and scalable implementation of
aerobic oxidation reactions for pharmaceutical synthesis. One approach involves a continuous-
flow process, which has been used to achieve aerobic oxidation of alcohols to aldehydes in near-
quantitative yields with reactor residence times as low as five minutes.
The development of practical, safe, and scalable oxidation methods of this type provides a
foundation for widespread adoption of oxidations using molecular oxygen by pharmaceutical,
fine, and specialty chemical manufacturers.
Professor
S. Stahl,
Department
of Chemical
and Biological
Engineering,
Uni¥ersity of
Wisconsin-Madison
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Amyris
Farnesane: a Breakthrough Renewable Hydrocarbon for
Use as Diesel and Jet Fuel
Innovation and Benefits
Renewable fuels are needed to help achieve global sustainability. Amyris took a step toward
this goal by engineering yeast to make a chemical called farnesene instead of ethanol.
Farnesene is a building block hydrocarbon that can be converted into a renewable, drop-in
replacement for petroleum dicscl without certain drawbacks of first-generation biofuels. Use
of Amyris's renewable diesel may produce 82 percent less greenhouse gas emissions than use
of petroleum diesel.
Transportation is second only to generating electricity as a source of greenhouse gas (GHG)
emissions in the United States, Gasoline consumption by automobiles is responsible for more
than half of all greenhouse gas emissions from transportation, while other uses, such as diesel fuel
for trucks, trains, or maritime use and jet fuel for aircraft, account for the remainder. Increases
in fuel prices have led many countries, including the United States and Brazil, to begin modern
large-scale production of biofuels. Locally-produced biofuels have the potential to be a significant
contributor to global sustainability, including providing local employment, ensuring access to
energy resources, and reducing GHG emissions.
First generation biofuels, notably ethanol and biodiesel (i.e., fatty add methyl esters), suffer
from limitations, such as limits on how much can be blended with gasoline or poor cold-weather
performance. To address the known shortcomings of first generation biofuels, Amyris developed
an advanced renewable fuel compatible with the existing vehicle and distribution infrastructure
that is now used in heavy-duty diesel engines and commercial aircraft.
Amyris used state-of-the-art strain engineering to make yeast that converts sugars into the
hydrocarbon farnesene rather than ethanol. Farnesene can then be hydrogenated to farnesane,
a renewable drop-in replacement for petroleum diesel and a blend-stock for jet fuel. A recent
lifccycle analysis estimated an 82 percent reduction in GHG emissions for farnesane, compared
with the EPA baseline fossil diesel—including indirect effects. Farnesane can also have land-use
benefits for heavy-duty transportation: a hectare of land growing soybeans to produce traditional
biodiesel generates enough fuel for a bus to travel about 600 miles. If the same land is instead used
to grow sugarcane to make ethanol, a bus adapted to run on ethanol could travel about 4,000
miles. However, if the sugarcane is used to produce farnesane, the unmodified diesel vehicle can
travel about 5,500 miles. Breakthroughs in converting lignocellulosic biomass to fermentable
sugars will further increase this benefit.
Amyris has demonstrated industrial-scale production using its proprietary yeast strains to
ferment sugars into renewable fuels that meet petroleum fuel specifications. Its renewable diesel,
which has been approved by EPA for blends up to 35 percent, contains no sulfur or particulates,
has a higher cetane number than diesel, and has improved low-temperature performance. More
recently, in June 2014, ASTM revised its standard for jet fuel to include the use of renewable
farnesane as a blending component in jet fuels for commercial aviation.
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Tailored Oils Produced from Microalgal Fermentation
Innovation and Benefits
Vegetable oils derived from plants can replace petroleum as building blocks for many indus-
trial chemicals, Solazyme has engineered microalgae to produce oils tailored to customers'
needs that can mimic or enhance properties of traditional vegetable oils. These micro-algae-
derived oils are consistent regardless of season, geographic origin, and feedstock source.
For thousands of years, civilization has used approximately 12 natural triglyceride vegetable
oils, including palm, soy, peanut, corn, olive, sunflower, and coconut, for food, energy, and
as building blocks to make a wide variety of chemicals. However, those oils may not have the
ideal composition for any particular use. Vegetable oils are isolated from their source, refined,
fractionated, distilled, and often chemically modified. Achieving the desired compositions from
plant oils is often energy intensive, expensive, can be wasteful, and, in some cases, requires use of
hazardous chemicals.
While some companies have turned to traditional biotechnology organisms, such as E. coli
and Saccromyces, to engineer to produce triglyceride oils, Solazyme recognized that the pathways
that make oil in canola, soybean, palm, and coconut first evolved in microalgae. Solazyme took
advantage of the inherent oil-producing ability of microalgae and developed a process to make oils
via fermentation.
Solazyme's technology combines the innate oil-producing machinery of algae with genetic
engineering to express the unparalleled diversity of oil production genes. Consequently, Solazyme
has the potential to produce a nearly unlimited variety of differentiated triglyceride oils while
dramatically reducing the time required to produce these oils. Solazyme has screened tens of
thousands of microalgae to identify the unique oils they produce with a broad array of chemical
and physical properties. In several commercial applications, Solazyme demonstrated that their oils
and lubricants reduce volatile organic compound (VOC) emissions and waste compared to use of
regular vegetable oils. Solazyme's oils are currently being tested and sold commercially for use in a
broad array of applications, including food, fuel, home and personal care, and industrial products.
Oils produced at Solazyme's joint venture facility in Brazil are expected to have a lower carbon
and water footprint than many current triglyceride oils and have a far lower environmental impact
than the petroleum-based products they replace.
Inc.
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QD ¥ision. Inc.
Greener Quantum Dot Synthesis for Energy Efficient
Display and Lighting Products
Innovation and Benefits
QD Vision makes higher-quality quantum dots—nanoscale LED components—using an
innovative greener process. These quantum dots make possible cost-effective full-spectrum
color in flat-screen displays and solid-state lighting. Historically, making quantum dots
involved hazardous chemicals and low yields, QD Vision's process has increased efficiency,
uses less hazardous building blocks, and eliminates nearly 40,000 gallons of highly toxic
solvent each year.
Most white light sources include a primary light source and a "downshifting" phosphor which
converts some or all of the primary light into the desired white light spectrum. In a typical
fluorescent bulb, electrified mercury gas produces the primary light in the ultraviolet (UV) range,
and phosphors (the whitish powder on the inside of the bulb) convert that UV light into white
light. Similarly, today's light emitting diodes (LEDs) produce a blue primary light, and phosphors
convert some of that light to make it appear whiter to the human eye. However, these LED
phosphors emit light in a broad band and result in a tradeoff between color quality and efficiency.
As a result, display manufacturers must either make displays that cannot show the full range of
colors found in nature, or greatly reduce the product's efficiency. Lower efficiency means that
more LEDs are required to achieve the same brightness, and hence cost more to make and need
more energy to run.
Semiconductor nanocrystal quantum dot technology offers high-quality color to the solid-
state lighting (LED light bulbs) and liquid-crystal display (TVs, mobile devices) markets
with high system efficiency. While developing these energy-saving materials, QD Vision also
developed a much greener synthesis. QD Vision estimates that they avoid using 150,000 liters
(40,000 gallons) of highly toxic solvent per year and avoid 100 kilograms of cadmium waste in
production in the United States. QD Vision achieved these improvements by replacing alkyl
phosphine- and alkyl phosphine oxide solvents with long-chain hydrocarbons, reducing both
the hazard and amount of solvent used. They also replaced highly hazardous organo-cadmium
and organo-zinc building blocks with less hazardous precursors. Finally, they improved their
purification by switching from centrifugation to filtration saving time and energy, and reducing
waste. QD Vision has implemented all of these changes while simultaneously improving material
performance. As such, QD Vision quantum dots were the first to be implemented in mainstream
commercial devices, including ten different models of Sony TVs in 2013.
Using QD Vision Color IQ™ components in 20 million TVs (equivalent to roughly 10
percent market penetration) is projected to save 600,000,000 kilowatt-hours (kWh) of electricity
per year worldwide—enough electricity to power 50,000 average homes in the United States.
Although QD Vision quantum dots do still use cadmium, the amount of cadmium used in
a device is less than the amount of cadmium emissions prevented through reduced electricity
production, resulting in a net decrease in cadmium waste.
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RE-HEALING^ Foam Concentrates-Effective Halogen-
Free Firefighting
The
Company
Innovation and Benefits
Fluorinated surfactants are critical components of firefighting foams, but they are persistent
chemicals and have the potential for environmental impacts. In developing RE-HEAL1NGIM
Foams (RF), the Solberg Company has replaced fluorinated surfactants in its firefighting
foam concentrates with a blend of non-fluorinated surfactants and sugars. The new foam
works well with far less environmental impact.
Firefighting foams suppress combustion by smothering burning fuels and cooling fires. For
years, these foams have used long-chain fluorinated surfactants as the "active ingredient". In 2006,
EPA established a voluntary stewardship program to reduce uses of long-chained fluorosurfactants
because they are persistent, bioaccumulative, and toxic. As a result, foam formulators switched
from long- to short-chain fluorosurfactants. However, almost 40 percent more fluorosurfactant is
required to meet the Underwriter Laboratories (UL) 162 firefighting foam performance standard
when using short-chain rather than long-chain fluorosurfactants. While less bioaccumulative and
less toxic, short-chained fluorosurfactants are still persistent, and, given the greater amounts used,
greater quantities of these short-chained fluorochemicals chemicals are expected to be released to
the environment.
Rather than simply switching to the short-chain fluorosurfactant, the Solberg Company
developed a line of halogen-free foam concentrates. After several years of research and testing on
fires, Solberg developed products that are equal, and in many cases superior, to their fluorinated
counterparts. Solberg's foams have achieved full regulatory compliance with existing fire protection
standards, while eliminating persistent chemicals. In particular, RE-HEALING™ Foam (RF) is
a very effective firefighting foam concentrate for flame knockdown, fire control, extinguishment,
and burnback resistance. Control, extinguishing time, and burnback resistance are paramount to
the safety of firefighters everywhere, and RF has excellent performance in each.
RE-HEALING1M Foam concentrates are a blend of hydrocarbon surfactant(s), water, solvent,
sugars, a preservative, and a corrosion inhibitor. Concentrates are formulated to be used as 1
percent, 3 percent, or 6 percent products to fight "Class B" hydrocarbon fuel fires. The presence
of complex carbohydrates gives the foam significantly more capacity to absorb heat than fluorine-
containing foam. This improves the extinguishing property of RF and adds to the burnback
capacity. The renewable hydrocarbons used in RF concentrates are the same products used in the
health care industry. The use of these blends results in a product that has very favorable hygiene
and environmental properties (including 93 percent degradation in 28 days, and complete
degradation by day 42). The RF concentrates are also easy to retrofit into existing foam systems as
a replacement to existing fluorosurfactant foams.
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Green Biological Production of Short and Medium Chain
Esters
Increasing global demand and reliance on petroleum-derived chemicals will necessitate
alternative sources for chemicals and all the products made possible by them. Currently, 99
percent of chemicals are derived from petroleum and natural gas. The ester classes of small
molecules are used for fragrances and cosmetics due to their fruity and floral aromas but are also
heavily used in paints, coatings, and solvents. In 2012, the global market for flavors and fragrances
was $16 billion. Small esters are commonly produced by acid-catalyzed esterification synthesis
of an organic acid and alcohol substrate that are usually sourced from petroleum under harsh
conditions. Synthetic biology and metabolic engineering enables the renewable production of
fuels and chemicals from microorganisms by constructing unique metabolic pathways. Professor
Atsumi and his team developed a new strategy for ester production that is cleaner and more
sustainable. The alcohol O-acyltransferase (ATF) class of enzyme utilizes acyl-CoA units for ester
formation, which takes advantage of the stored energy in the thioester bond of the acyl-CoA
molecule. The release of free CoA upon esterification with an alcohol provides the free energy to
facilitate ester formation under green conditions. Thus, Professor Atsumi and his team engineered
the industrial production host, Escherichia coli, to produce various esters under green conditions
(water and ambient temperatures) and from a renewable carbon source (glucose). They achieved
high-yield and titer production of isobutyl acetate, which demonstrates the commercial potential
of this platform. Ultimately, Professor Atsumi and his team demonstrated production of 13
different ester compounds using the strategy. This renewable technology can potentially replace
petroleum-derived ester synthesis, greatly reducing carbon emissions and the associated health
hazards.
The Scalable Production ofEdge-Functionalized Few
Layer Graphene Oxide
Edgc-functionalizcd few layer graphcnc oxide (EFGO) can be rapidly prepared in large
quantities by mechanochemical means. Grinding graphite with urea hydrogen peroxide adduct
produces a highly delaminated product with an oxygen content of 5-20 percentage by weight.
The only byproducts of this synthesis are water and urea. This process does not require toxic
reagents and It produces byproducts generally considered safe. The edge-functionali/ed graphene
produced by this method is hydrophilic and easily suspended in water, allowing for convenient
processing of films and epoxy composites. It can also be electrodeposited to form uniformly
smooth coatings. This material is electrically conductive and free from manganese impurities
that often plague graphite oxides prepared by Hummcrs'-typc methods. Analyses show that the
graphite is fully oxidized to —COOH groups along the edges of individual graphene sheets. This
approach offers a scalable, environmentally benign route to large quantities of EFGO.
Professor
Atsymi,
Department
of Chemistry,
University of
California-Dawis
Professor Richard
Technology Center,
The Uni¥ersity of
Central Florida
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A. Dumesic,
Department
of Chemical
and Biological
Engineering,
Uniwersity of
Wisconsin-Madison
Garg,
of Chemistry
Biochemistry,
University of
California-Los
Angeles
Enzyme-Free Biomass Depolymerization Using GVL
The need for renewable alternatives to petroleum-based resources has never been greater.
Reliance on fossil fuel extraction currently poses environmental, economic, and political threats
worldwide, Biomass-derived fuels and chemicals provide a renewable alternative to products
traditionally generated from fossil fuels and yet previous efforts to transform cellulose-containing
biomass into fuels and other products have often relied on expensive, energy-intensive, and
sometimes toxic chemical protocols. Developing environmentally sustainable and economically
viable biofuels and bio-based products thus depends on developing greener and more streamlined
ways of breaking down cellulose into sugar.
Researchers at the University of Wisconsin-Madison have shown that y-valerolactone — a small
molecule solvent that can be renewably sourccd from biomass — promotes efficient and selective
thermal breakdown of cellulose in the presence of dilute aqueous acid. The researchers have
successfully performed laboratory-scale production of soluble carbohydrates from corn stover,
hardwood, and softwood at high yields (70 to 90 percent) in a solvent mixture of biomass-derived
y-valerolactone (GVL), water, and dilute acid (0.05 weight percent HbSO/j). A key advantage
to this process is that it replaces enzymes and significant quantities of acid with a green solvent
easily producible from biomass itself. GVL can also be easily separated by adding small amounts
of liquid carbon dioxide.
An initial economic assessment indicates that this technology could produce ethanol, and
perhaps other biofuels, at a cost savings of roughly 10 percent when compared with current state-
of-the-art technologies. Through Wisconsin Alumni Research Foundation's Accelerator Program,
University of Wisconsin researchers are now constructing a high-efficiency biomass reactor
that will use GVL to produce concentrated streams of sugars and intact lignin solids for use by
scientific collaborators optimizing the conversion into valuable chemicals and fuels. With the use
of this technology, it turns out that the secret to success in creating plant-based fuels wras within
the plants themselves.
Catalytic Cross-Couplings Using a Sustainable Metal
Green Solvents
The nominated technology involves one of the most important classes of organic reactions
used in modern research: transition metal-catalyzed cross-coupling reactions. These reactions are
amongst the most effective and widely used means of constructing carbon—carbon (C—C) and
carbon—heteroatom (C—X) bonds. The importance of cross-coupling methodology is underscored
by the 2010 Nobel Prize given "for palladium-catalyzed cross-couplings in organic synthesis."
Arguably, the most widely used and reliable coupling methodology is the Suzuki—Miyaura
coupling to forge C-C bonds. These couplings have transformed the landscape of drug discovery
and development.
Given the importance of the Suzuki—Miyaura coupling, the development of "greener" variants
has been a topic of great interest. The American Chemical Society's Green Chemistry Institute's
Pharmaceutical Roundtable has highlighted the limitations associated with these couplings and,
more recently, has incentivized academic research in this area by making it the focus of their
2012 grant cycle. Since 2008, the Garg laboratory at the University of California-Los Angeles
has pursued the development of ''greener" and more sustainable Suzuki—Miyaura couplings for
use in academic and industrial applications. The key green chemistry challenges targeted include:
(a) developing Suzuki—Miyaura couplings that do not require the use of the precious metal
palladium, (b) discovering conditions that proceed in green solvents, rather than less attractive
solvents (source reduction), and (c) uncovering a unified set of reaction conditions to enable the
Suzuki—Miyaura coupling of an unprecedented range of substrates.
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By targeting the aforementioned challenges systematically, the Garg laboratory has developed
Suzuki—Miyaura couplings that use inexpensive nickel-catalysis, proceed in "greener" solvents
such as alcohols, and are tolerant of a vast range of substrates, including heterocycles, in addition
to a variety of electrophiles (e.g., halides and pseudohalides). These studies have led to discoveries
in fundamental chemical reactivity and new tools for cross-coupling chemistry. Finally, these
efforts have fueled educational initiatives in green chemistry where undergraduate students have
performed '"green" Suzuki—Miyaura couplings in an instructional laboratory.
Green Approaches of Nanocomposite Material Synthesis
for Energy Storage, Environmental Surveillance and
Sustainable Food Systems
Graphene sheets have high specific surface area, large electrical conductivity, and robust
mechanical strength. It is readily produced in tons. Current economical and effective production of
graphene in mass from graphene oxide (GO) requires reducing reagents such as hydrazine, alkaline,
ethylenediamine, NaBH/{, and urea, which are toxic, corrosive, or even explosive. The process
with reducing reagents and stabilizers to improve reduced GO dispersion are time-consuming
and usually undesirable due to their damage on electronic properties. Graphene nanocomposites
with metal nanoparticles can have synergistic effects for use in different applications such as
energy storage, biosensors, and optical electronics. However, the synthesis of these nanoparticles
from their salt precursor solutions also needs hazardous reducing reagents. Therefore, a large-
scale greener and more effective synthetic route of graphene and graphene nanocomposites is
an unmet need. A facile, controllable, and cheap electrochemical approach was used to perform
rapid and green synthesis of graphene and graphene-based nanocomposite materials for energy
storage, environmental surveillance, and sustainable food systems. Compared to reduction by
constant potential or current, a repetitive cathodic potential cycling reduction was designed,
which can completely remove unfavorable electrochemically unstable oxygenated groups and.
generate a two-dimensional, defect-free homogeneous graphene film with excellent stability and
electronic properties. The synthesis can be successfully conducted on different flat and rough
substrates such as indium tin oxide glass, glassy carbon, and graphitic carbon. Applications of
graphene and graphene nanocomposites from this green route without generating any hazardous
wastes are exhibited as supercapacitor, oxygen reduction reaction, and biosensing in food and
environmental samples. By using a patented replaceable technology for the developed solid-state
electrodes, wastes such as alumina slurry and water from electrode washing can be avoided.
Ultrasound Induced, Copper Mediated Homo-Coupling
Using Polymer Supported Aryltrifluoroborates
The homocoupling of aryl compounds is an important reaction used in the formation of
fundamental building blocks for numerous industrial and pharmaceutical materials. Unfortunately,
many of the widely used homocoupling reactions require expensive catalysts or use harsh reaction
conditions with large quantities of metal while producing only modest product yields. In an
attempt to improve the negative aspects of these reactions, researchers have employed a variety
of tactics including the use of different metals, ultrasound or microwave energy sources, various
solvent systems, and different ligands, all with varying degrees of success. There are a number of
reports that indicate successful synthesis of biaryl compounds using polymer supports. Benefits
of the modification include successful reactions run in water and under atmospheric conditions
with good product yields. Regrettably, these reactions are not atom efficient, and require extensive
preparation of the polyethylene glycol, with harsh chemicals and environmentally toxic solvents,
before it can be used in the reaction. Since Dowex is commercially available, the Kabalka group
attempted a homocoupling reaction similar to the reported polyethylene glycol methods.
Gunasekaran,
of
Engineering,
University of
Wisconsin-Madison
Jiang Yang,
LignoCarbon
Mfysolino,
Uniwersity of
Tennessee-Knoxwille
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Professor Satomi
Niwayama,
of
Chemistry
Biochemistry,
Tech University
Professor Jeffrey
Pyun
of
Chemistry &
Biochemistry,
University of
Arizona
Palladium(II) acetate was chosen as the survey metal, following the reported methods. Initial
survey reactions using heat and stirring indicated only minimal product yield (seven percent)
after 72 hours. It was decided to carry out the reaction using an ultrasound energy source, which
provided a significantly improved yield of 92 percent while decreasing reaction time to six hours.
To develop a more environmentally friendly reaction, the copper acetate replaced the palladium
salt, and the aqueous tetrahydrofuran solvent was changed to aqueous ethanol. Product yields
remained excellent at 96 percent. The reaction is green, atom efficient, and, in later reactions,
showrn to be scalable as compared to currently used industry reactions.
Highly Efficient and Practical Monohydrolysis of
Symmetric Diesters
Water is the least expensive solvent and among the most environmentally friendly solvents.
Among various synthetic conversions, desymmetrization of symmetric compounds is one of the
most atom-economical and cost-effective reactions, because the starting symmetric compounds
are typically obtained easily on a large scale from inexpensive sources, or are commercially available
inexpensively. Therefore, water-mediated desymmetrization of symmetric organic compounds is
of tremendous synthetic value, and makes a significant contribution to creating greener reaction
conditions.
Dr. Niwayama pioneered water-mediated desymmetrization. In particular, she has been
developing monohydrolysis of symmetric diesters as the wrater-mediated desymmetrization
reaction. Half-esters, which arc produced by such monohydrolysis of symmetric diesters, are
versatile building blocks in organic synthesis applied to synthesis of polymers and dendrimers
with applications to industrial products of commercial value. Unfortunately, since the two ester
groups in symmetric diesters are equivalent, the statistically expected yield of half-esters would
be a maximum of only 50 percent. Classical saponification usually affords complex mixtures of
dicarboxylic acids, half-esters, and the starting diesters, which are difficult to separate, yielding a
large amount of undesirable dirty waste. Ring-opening reactions of cyclic acid anhydrides require
hazardous organic solvents. However, Dr. Niwrayama discovered a highly efficient and practical
ester monohydrolysis of symmetric diesters. In this reaction, an aqueous base such as NaOH or
KOH is added to a symmetric diester suspended in water at 0°C, With this simple reaction, pure
half-esters are obtained in high to near-quantitative yields without production of dirty waste and
without use of hazardous organic solvents. This reaction, wrhich is anticipated to significantly
contribute to green chemistry, has been licensed by three companies, and several half-esters
produced by this reaction have been commercialized.
Utilization of Elemental Sulfur as a New Chemical
Feedstock for Polymeric Materials
The nominated, technology focuses on the development of new polymerization methods to
convert elemental sulfur into useful polymeric materials. Anew generation of sulfur-based plastics
has resulted from these new synthetic advances, where these materials have been demonstrated to
possess useful electrochemical and optical properties. The surfeit of elemental sulfur (Sg) generated
from petroleum refining has created an incredibly abundant and inexpensive supply of sulfur.
However, there remain only limited uses for elemental sulfur toward the production of other
chemicals (e.g., sulfuric acid), and there is a paucity of synthetic chemical methods to modify, or
directly convert elemental sulfur into useful polymers and alternative materials. This challenge
arises from the incompatibility and limited miscibility of sulfur with the majority of chemical
reagents and solvents. To obviate these fundamental synthetic challenges, the team of Pyun and
Glass has developed a new concept of using molten liquid sulfur as an unconventional solvent and
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reagent tor chemical reactions used to prepare gold nanopardcle nanocomposites and high content
sulfur polymers. To convert sulfur into a chemically stable and useful plastic, Pyun and Glass' team
has developed a new polymerization method termed inverse vulcanization that tor the first time
uses molten liquid sulfur as the reaction medium and comonomer for the synthesis of sulfur-rich
copolymers. They demonstrated that these sulfur-based plastics possess unique electrochemical
and optical properties, which enabled their application in devices for enhanced lithium-sulfur
batteries and infrared thermal imaging. These collective findings point to the creation of a new
field of sustainable sulfur chemistry for advanced materials with significant environmental and
technological benefit through the use of excess sulfur. This work has generated five publications
and one patent application.
Bacteriopb age-Based Bacterial Identification and Antibiotic
Resistance Test
Antibiotic-resistant bacterial infections arc a serious and growing global health problem.
Conventional antibiotic resistance determination techniques typically require laborious and time-
intensive culture-based assays, which take up to 96 hours and expend an inordinate amount
of disposable plastics and bacterial growth media. In contrast, the Colorado School of Mines
(CSM) bacteriophage amplification platform enables rapid simultaneously identification and
antibiotic resistance determination without the need for extensive culturing, minimizes the use
of disposable plastics, and reduces overall environmental impact. More importantly, with respect
to its impact on human health diagnostics, these attributes result in more user-friendly tests with
significantly reduced testing times of less than five hours. First described, developed, and patented
by the Advanced Biodetection Technologies Laboratory (ABTL) at CSM, the intellectual property
covering this technology was licensed by MicroPhage in 2002 for commercial development.
MicroPhage advanced the technology through the Food and Drug Administration (FDA) 510(k)
approval process, but then filed for bankruptcy in 2012 and returned all licensed technology
and intellectual property to CSM. During that time and continuing to the present, the ABTL
has advanced the technology through several key breakthroughs that allow even more sensitive
and rapid bacterial detection with a focus on green chemistry practices while maintaining the
technology's minimal environmental footprint.
Phages are viruses that infect targeted bacteria in a species-specific fashion. The phage
amplification process can generate as much as a 5-log signal amplification versus detection
of bacteria alone. In addition, because of the reliance of phages on a viable bacterial host,
simultaneous drug resistance determination is achieved through parallel, multiplexed phagc
amplification reactions with and without the addition of any given antibiotic. The CSM
approach has miniaturized the process to a milliliter level and has incorporated modern green
chemistry technologies for detection of progeny phage on a dual track lateral flow immunoassay
strip, which is analogous and read like a typical home pregnancy test. A positive result from the
first drug-free reaction indicates the presence of target bacteria. A positive result from the second,
drug-containing reaction shows that the target bacteria were antibiotic resistant. The phage
amplification platform was the first FDA-approved in vitro diagnostic for direct identification
of bacteria and determination of antibiotic resistance or susceptibility. The CSM rapid bacterial
identification and antibiotic resistance determination test embodies the tenants of green chemistry
by benefiting human health with advanced diagnostic capacity using natural phage products and
greener reagents, and by significantly reducing environmental waste and power consumption.
Professor Kent
J. ¥oorhees,
Department
of Chemistry,
Colorado of
Mines
13
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E.
Wy man,
of Chemical
Environmental
Engineering,
University of
California-Riverside
Professor Yi-Heng
Percival Zhang,
of
Engineering,
¥irginia Tech
UCR Co-Solv Technology Achieves Unprecedented
Yields of Fuel Precursors from Lignocellulosic Biomass
Professor Wyman and his team has developed an integrated biomass pretreatment and
conversion strategy, named "Co-Solv," to promote the production of fuel precursors furfural and
5-hydroxymethylfurfural (5-HMF) directly from lignocellulosic biomass as a future platform
for sustainable biofuel production. These fuel precursors have been considered by the U.S.
Department of Energy as top platform chemicals for the production of renewable chemicals and
liquid transportation fuels if they can be obtained at high yields and at low cost from lignocellulosic
biomass. As biomass feedstocks costing $60/dry ton are equivalent in energy cost to petroleum at
about $20/barrel, they are distinctive in being the only sustainable resource sufficiently inexpensive
and abundant to make a large impact on liquid fuel use. Green processes that can economically
convert low-cost biomass into compatible transportation fuels that have enormous benefits for
addressing global climate change, national energy security, economic growth and employment,
trade deficits, and global competitiveness issues. Co-Solv is a highly tunable and scalable process
to simultaneously solubilizc lignocellulosic biomass and catalytically convert hydrolyzcd sugars
into fuel precursors. In one arrangement, Co-Solv technology employs a one-pot monophasic
reaction combining a renewable solvent with non-corrosive solid acid catalysts to produce the
highest overall yields furfural (>90 percent) and 5-HMF (>45 percent) directly from biomass. Co-
Solv is greener and more effective than other competing strategies such as biphasic reactions, ionic
liquid systems, and other co-solvent systems because it is low-boiling, relatively non-toxic, and
can be renewably produced from furfural as a final product to supplement a continuous reaction
strategy. Professor Wyman and his team has also successfully compared these results with current
industrial methods to show an impressive product yield advantage, which could result in low-cost,
largescale production. Lignin removal is also extensive, achieving ~-90 percent delignification of
hard woods to maximize the utility of all major fractions of lignocellulose reducing solid waste
products.
High-Yield and High-Purity Hydrogen Production
from Carbohydrates via Synthetic Enzymatic Pathways
Hydrogen is one of the most important chemical intermediates produced from fossil fuels and
will become one of the best transportation fuels and energy storage compounds in the future. The
production of carbon-neutral hydrogen from renewable resources and the storage of high-density
hydrogen are the two greatest challenges for the hydrogen economy. Carbohydrates, including
cellulose, hemicellulose, starch, and sucrose, are the most abundant renewable bioresources. They
are produced through plant photosynthesis. Professor Zhang has designed non-natural synthetic
enzymatic pathways that can release all of the hydrogen from a variety of carbohydrates and water
under mild reaction conditions (e.g., 30-60°C, atmospheric pressure, and aqueous solution),
that is, the production of 12 H2 per hexosc and 10 H2 per pentose. These synthetic enzymatic
pathways are comprised of more than 10 enzymes from different sources, such as archaea, bacteria,
animals and plants, as well as coenzymes, including biomimetic analogs. Furthermore, Professor
Zhang suggested the use of carbohydrates as a high-density hydrogen carrier with a gravimetric
density of up to 14.8 H2 mass percent, far higher than the Department of Energy's hydrogen
storage goals. To decrease its production costs, Professor Zhang has developed a number of ultra-
stable enzymes with total turnover numbers of up to 1,000,000,000 mole of product per mole of
enzyme and succeeded in changing the coenzyme preference of redox enzymes to low-cost and
ultra-stable biomimetic coenzymes from costly and unstable natural ones. Also, Professor Zhang
has increased its production rates by 800 times, 75 times the best algal biohydrogen production
rate. Current carbohydrate-to-hydrogen rates are fast enough for small-size distributed hydrogen
generator systems that utilize local biomass resources. This work was done in collaboration with
Professor Mike Adams of the University of Georgia, Drs. Jonathan Mielenz and Barbara Evans at
the Oak Ridge National Laboratory, and Dr. Joseph Rollin at Cell Free Bioinnovations Inc.
14
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Pathed®/PathShield™ Antimicrobial Filter Media for the
Control of Bacteria in Stormwater and Industrial Process
Waters
A S Filtration™, LLC developed Pathex'*1 Antimicrobial Filter Media (PathShield™ is an Alternate
Brand Name) tor the reduction and control of coliform bacteria in Stormwater, industrial waste
water, rccirculating cooling towers, heat transfer systems (evaporative condensers, hydrostatic
sterilizers and retorts, brewery and other pasteurizers, and warmers), industrial fresh water
systems, service water and auxiliary systems, and municipal waste water treatment. Commercial
applications demonstrate 20 percent water savings, enhanced temperature exchange capacity
by reducing biofilm resulting in energy savings up to 40 percent, and significant decreases in
traditional chemical biocide use by at least 75 percent.
Our technology confirms the 1970s theory that the unique surface bond of an organosilicon
quaternary ammonium chloride compound to siliceous materials, without release of chemical,
offers a new approach to water treatment. Efficacy is achieved at high loading rates up to 20
gpm/ft2without releasing, discharging, or leaching any antimicrobial agents, chemicals, or heavy
metals. Pa thexw/PathShield™ kills coliform bacteria as the organisms physically move over the
hostile surface of filter media granules. The antimicrobial filter media is stable, non-toxic, not
consumed, requires no power source for efficacy, non-corrosive, and not affected by temperature
changes. There are no harmful disinfection byproducts such as total trihalomcthancs, haloacctic
acids, bromate, or chlorite formed by using Pathex'B7PathShield™ filter media for treating water.
Independent laboratory testing and field demonstrations support the significant health
and environmental benefits achieved through the use of Pathex®/PathShield™ filter media.
Laboratory challenges achieved up to log 4 reductions in E. coli, total aerobic bacteria, Legionella
pneumophila, sulfate reducing bacteria, and iron fixing bacteria. Stormwater field demonstrations
further support high efficacy against E. coli, enterococci, and total coliform bacteria. Long-term
suppression of total aerobic bacteria and total coliform bacteria in industrial cooling towers using
PathShield™ within a high efficiency side-stream filter has been documented.
A Greener, Safer and More Energy Efficient Antifreeze
Ethylene glycol, the main ingredient in antifreeze, smells and tastes sweet, attracting both
children and pets to consume it. Ethylene glycol should not be confused with propylene glycol,
a common food additive. Drinking ethylene glycol antifreeze will cause heart and breathing
difficulties, kidney failure, brain damage, and even death. The major cause of toxidty is not the
ethylene glycol antifreeze itself but its metabolites. The American Association of Poison Control
Centers reported that there were 5,784 poisonings due to ethylene glycol antifreeze in 2012.
There were 431 reported cases of children under the age of 5 years old and some of these cases
were fatal.
ACTA's product improves the heat transfer capability of propylene glycol and is 58 percent
better than ethylene glycol antifreeze in a circulating cooling system. Therefore, heat transfer
performance and cost should no longer be reasons to use the potential lethal ethylene glycol
antifreeze.
ACTA's additive to propylene glycol antifreeze can reduce dependence on foreign oil and
reduce greenhouse gas emissions because of improved energy efficiency. ACTA's product covers a
greener and non-toxic chemical.
A S Filtration™, LLC
ACTA Technology
Inc.
15
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lay LLC
Copperhead
Chemical Company
Inc.
GreenLife
Development
Consumer Viable and Environmentally Friendly Solvent
Replacements Developed From Food Grade Compounds
The BODYGUARD is a new, water-based and environmentally friendly, multi-surface
treating emulsion developed to replace solvents, dcgrcasing agents, and cleaning agents that
use chlorofluorocarbons, specifically iiiethylchloroform, CFC-13, and HCFC-225- The
BODYGUARD uses cavitation, capillary attraction, and encapsulation to protect and clean
surfaces from bonding materials such as epoxies, frozen loads, wet soils, clays, wet concrete, ice,
asphalt, and biofouling. The patented formula controls surfaces and creates a bridge across the
millions of micropores on surfaces that allow bonding.
In 2013, Bay State Tech, LLC completed its 12-month field testing of the BODYGUARD
and secured manufacturing of the product. In 2014, Bay State Tech, LLC began responding
to procurement opportunities from different municipalities across the United States. The
BODYGUARD is a USDA certified Bio-Preferred product and tested to be 96 percent bio-
based. The technology is a combination of water with food grade additives including a boron
compound, a gelling compound, and an inorganic alkali compound.
Novel, Effective, Safe Delivery System for Antimicrobial
Agents Derived from Sustainable Vegetable Monoglycerides
Biopolys;
;an~ is a novel
16
antimicrobial composition derived from coconut oil. The patented
manufacturingprocess is a relatively low temperature, single vessel reaction wherein monoglycerides
are heated in the presence of a polyhydric alcohol and an alkaline catalyst. The result of processing
is a liquid crystal mixture of glycerol and propylene glycol esters and salts thereof with drastically
improved solubility, stability and efficacy. Biopolysan* is composed of generally recognized as safe
(GRAS) food-grade ingredients. The active ingredient, glyceryl laurate, is derived from coconut
oil, a renewable source. There is no waste stream and no harmful byproducts are produced by the
process. Biopolysan'* has applications in numerous industrial and medical settings including as a
preservative and other anti-microbial applications.
Commercialization of Biopolysan* as a multifunctional ingredient for use in various
formulations began in 2012. The benefits to the formulator are many, and include green
preservation, greener chemistry, emolliency, improved penetration and skin feel as well as cost
savings and simplification of the manufacturing process when Biopolysan* replaces a plurality
of ingredients in some products. Current products on the market formulated with Biopolysan'8'
include both animal and human products. Once Biopolysan'*1 120 (Copperhead's standard
Biopolysan® formulation) receives its F1FRA registration, commercialization of Biopolysan'*
as a preservative is expected to replace a portion of the annual 40,000 metric ton traditional
preservative market.
Naturama—Oil Surfactant, Green Degreaser, and Cleaner
Naturama is a naturally-derived, plant-based feedstock that is a water soluble solution utilized
in an array of industries to remove grease and clean surfaces, without leaving the harmful
environmental impact evidenced in other comparable products. The benefits of Naturama are
extensive. It is 100 percent biodegradable, non-enzyme-based, non-toxic, and non-ionic. It is
hypo-allergenic, non-caustic, and non-flammable.
Other industries' products contain toluene, tetrachloroethylene, hexane, heptanes, and other
toxic chemicals that pose extreme fire hazards as well as both short- and long-term health hazards.
Additionally, the cost of these competitor products extend beyond the product to regulatory
compliance, training, protective gear, environmental controls, waste management services, and
employee cost. With Naturama, the oil molecules quickly degrade through a much expedited
photosynthesis process ranging from minutes to a few weeks.
-------
The primary industrial applications targeted for Naturama are automotive and food service.
Specifically, dcgrcasing and cleaning of automotive parts and cleaning facilities. Significant
opportunities have been identified in manufacturing, drilling, marine, and even household
applications.
When compared to other toxic products, Naturama saves a tremendous amount of energy
because it does not require a heat source when used. Being non-toxic, employee safety is not
compromised, and no special storage is required. The volume of material needed is reduced
to very small quantities. The waste of participate matter, after filtration, is the only hazardous
material to be disposed of, reducing the waste stream. Naturama is not hazardous in its initial
component, nor in its life cycle after filtration. Naturama can be used completely during its life as
a cleaner/degreaser in various applications and industries.
Cooling Tower Water Conservation & Chemical
Treatment Elimination
Properly engineered electrolytic extraction of calcium carbonate from recirculating cooling
water has successfully controlled deposit formation on heat exchange and other surfaces in
practical systems such as industrial and HVAC cooling tower systems. Electrolysis of ionic-rich
water produces exploitable in situ chemistry requiring no external chemical reagent other than
electricity. A Green Machine consists of a series of steel tubes that are made the cathodic element
of an electrolytic cell where water is reduced to form molecular hydrogen and hydroxide ion,
and calcium carbonate is subsequently made to accumulate. Centered in each tube typically is
a titanium rod coated with a mixture of ruthenium and iridium oxides, which make the anode
of the electrolytic cell. The common name for an anode of this type is "dimensionally stable
anode," or DSA. It is the coating of the anode that is critical in driving the oxidation of water to
produce molecular oxygen, hydrogen ion, and higher oxygen species such as hydroxyl free radical
and ozone. DSA technology allows for the efficient splitting of water at a low practical voltage
potential above that theoretically required, the difference being termed "overpotential." DSAs
have been responsible for past Green Machine success. Supplementing DSAs with anodes coated
with boron-doped, ultrananocrystalline diamond (BD-UNCD) now allows not only control over
troublesome calcium carbonate deposition, but more efficient in situ chlorine formation and
degradation of organic contaminants. Microbiological control in cooling water is significantly
more efficient.
High Performance Solvent-Free Coating Technology
Corrosion is a tremendous problem and cost to society, with a staggering annual cost of $400
billion in the United States. Many primers and paints used to coat metal surfaces for corrosion
resistance and decoration pose environmental hazards from cradle to grave. Conventional epoxy-
based coatings commonly contain corrosive components, hazardous air pollutants (HAPs), volatile
organic compounds (VOCs), and other solvents, and often contain chromium compounds.
Urethane-based paints contain isocyanates and often contain HAPs, VOCs, and other solvents.
Because isocyanates are strong irritants to mucous membranes, they can sensitize exposed
individuals, in some cases causing severe asthma attacks. The hexavalent form of chromium is
carcinogenic, particularly for lung cancer.
Light Curable Coatings has developed pollution-free coating technology for high performance
protection of industrial and aerospace surfaces, including corrosion resistance, solvent resistance,
and weathering resistance. Light Curable Coatings technology also provides the advantages
of efficiency and economy, with fast cure under an ultraviolet (UV) light and with improved
properties with much less material usage than conventional materials. The green chemistry of
Light Curable Coatings does away with chromium compounds, isocyanates, and other HAPs,
H-O-H
Technology, Inc.
Light Cyrable
Coatings
17
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Newlight
Technologies, LLC
Sirrys, Inc.
solvents, and VOCs completely, producing high-performance, corrosion-resistant, solvent-free
technology without using any toxic chemicals. Field application and fast UV cure of Light
Curable Coatings technology has been demonstrated with good performance on large structures
at temperatures as low as 34°F. Customer studies show savings of over 90 percent in the time
required for painting operations for maintenance activities and factory processes.
Light Curable Coatings technology is a green alternative to current systems that contain toxic
components, and provides a significant positive societal impact in terms of a better quality of life
for industrial workers and for citizens through safer workplaces and a cleaner environment.
AirCarbon: Carbon-Negative Plastic Made from
Greenhouse Gas
Newlight Technologies has developed a carbon sequestration technology that uses air and
greenhouse gas emissions to produce a plastic material called AirCarbon. AirCarbon has been
independently verified byTrucost and NSF Sustainability as a carbon-negative material, and is
being used to directly replace oil-based plastics in a wide range of market segments. Based on
Newlight's high yield biocatalyst breakthrough, AirCarbon can be produced for significantly less
than the cost to produce oil-based plastics, representing a market-driven solution to reducing
greenhouse gas emissions.
Founded in 2003 out of Princeton University and Northwestern University, the founding
principle of Newlight was that climate change can be solved if carbon emissions are used as a
resource to produce products that out-compete oil-based products on price and performance.
After nearly a decade of research, Newlight achieved a breakthrough in the company's greenhouse
gas conversion technology that increased the yield of the process by over nine times relative to
previous efforts, a breakthrough that fundamentally shifted the economics of greenhouse gas
sequestration. Today, Newlight is able to use that technology to harness carbon emissions as a
resource to produce plastics for significantly less than the cost to produce plastics from oil.
In 2012, nine years after the company's founding, Newlight began selling AirCarbon for the
first time, and by the end of 2012, had generated executed letters of intent to purchase AirCarbon
in excess of 12.5 million pounds. In August 2013, Newlight scaled up the AirCarbon production
technology to commercial scale, using air and carbon emissions from an agricultural operation to
manufacture AirCarbon thermoplastic. In November 2013, Newlight launched the world's first
carbon-negative furniture made with AirCarbon to market. Today, Newlight is working with
over 25 partners in nine market segments to use AirCarbon to replace oil-based plastics.
Disruptive 1,1-DisubstitutedAlkene (1,1-DA)
Green Chemistry Platform, Step Change in
Manufacturing: Breakthrough High Performance,
Energy Efficient, Sustainable Green Polymer
Platform to Transform Industrial Manufacturing
Sirrus advances manufacturing technology through chemistry relating to the synthesis,
stabilization, activation and formulation of a unique and reactive class of monomers commonly
known as 1,1-DAs. These monomers, their derivatives and resulting polymer platforms provide
the foundation for meeting customers' needs through game-changing technology.
18
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Specifically, Sirrus is advancing chemistry relating to the isolation, stabilization, activation,
and formulation of 1,1-DAs. These monomers, their derivatives, and resulting polymers provide
fast cure speeds at ambient temperatures to significantly reduce cycle times, increase throughput,
reduce energy costs, and enable new material selection in a broad range of customer and consumer
applications, including auto, electronics, packaging, and hygiene.
Moreover, Sirrus' technology enables improved features such as increased temperature, water,
environmental, and solvent resistance in downstream products. Sirrus' green chemistry platform
reduces pollution at its source by minimizing and eliminating the hazards of chemical feedstocks,
reagents, solvents, and products.
1,1-DAs are molecules that embody a platform with a wide variety of substituents or side-
chains. The overall chemistry and behavior of 1,1-DAs are analogous to cyanoacrylates (super
glue); e.g., both cure anionically. However, 1,1-DAs possess superior environmental resistance
for enhanced product application compared to traditional cyanoacrylates. This chemistry also
suggests potential synthesis of monomers specifically designed for a given functionality; e.g.,
adhesives, inks, sealants, stains, coatings, etc. Similar compounds have been investigated since
1886 without notable synthetic improvement. Limited in-depth understanding of system
stabilization and inherent monomer reactivity precluded chemists from obtaining sufficient
yields needed for commercialization. Sirrus' platform provides variability and derivitized resin
development that translate to appealing features and benefits; e.g., high speed and zero-energy
polymerization, tailored solvent and thermal resistance, and increased product life.
CIRKIL Biopesticide
Pesticides are critical to society, increasing agricultural output, managing disease, and
enhancing human comfort. Despite these benefits, Conventional Chemical Pesticides (CCPs)
are under increasing scrutiny. For years, CCP producers have created small-molecule pesticides,
delivering efficacy primarily through toxicity. Regrettably, these pesticides can be toxic to target
and non-target pests, humans, and other animals. Insects also develop resistance to CPPS and
CPPs typically biodegrade slowly becoming persistent in the environment. Put simply, CPPs are
important but indiscriminately toxic, are easily "outsmarted" by the target insect, and persist in
the environment. The conventional approach to deal with these challenges has been to ''double-
down" and create more synthetic pesticides.
Terramera has a significantly different approach. Rather than creating novel molecules,
the company has created a novel, patent pending formulation technology that stabilizes and
potentiates the natural efficacy of plant bioactives. Terramera has shown that plant biochemicals
are effectively delivered into the insect's organism as a result of this technology, enabling
development of plant-based biopestiddes that perform as well or better than CCPs.
Terramera has successfully commercialized a bio-pesticide targeting bed bugs with this
technology potentiating cold pressed neem oil to deliver superior efficacy to CCPs, in a minimally
toxic formula. Terramera is extending this technology into agriculture developing novel products
using botanical bioactives to treat insects, plant parasites, and fungi with field trials in progress.
By substituting with Terramerra, a single large strawberry grower in California could annually
displace 540,000 pounds of methyl bromide/chloropicrin, a CCP being phased out in the United
States.
Terramera Inc.
19
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SAFEN: A Low Cost Nematicide and Fungicide That
is Generally Regarded as Safe by the FDA, Which
Biodegrades into Two Naturally Occurring Substances,
with No Lasting Detrimental Effects to Air, Soil, and
Water
The nominated technology is for the production and use of SAFEN, a green chemical nematicide
and fungicide that is environmentally friendly to air, soil, and water. The Montreal convention
emphasized the need for pesticides which were environmentally friendly and eliminated the use of
methyl bromide, an ozone depleting agent commonly used worldwide, SAFEN represents a green
alternative to methyl bromide. SAFEN's components are made from low cost raw materials. Its
primary component ethyl formate is made from cthanol, a renewable resource. SAFEN's simple
molecules biodegrade into naturally occurring substances after effective use. SAFEN was applied
to plots of up to 4 hectares with the capability of surface spraying or drip feeding to enable studies
of complexities associated with different field operations. The analytical services of University
of California-Davis, the University of Guanajauto, and Cinvestav were essential to the study
together with attendant advice and field operations.
The eVOLV™ System, a Clean, Sustainable Solution to
Electronic Waste
The eVOLV system was created to help solve the global issue of electronic waste (e-waste).
While laws in developed nations have been pushing to regulate or eliminate dirty, harmful e-cycling
practices and scrap piling, underdeveloped nations are seeing their lands being used as dumping
sites. These sites host opportunities for people, including children, to use dangerous open burning
techniques and toxic chemicals to extract metals tor resale. While these conditions are deplorable,
the piles themselves arc growing and arc polluting the soil and groundwater.
A United Nations report states that e-waste will grow by one-third by the year 2017 to total
about 65.5 million metric tons. According to the report, the United States produced 9.4 million
metric tons in 2012—the most of any country. In all, e-waste is the fastest-growing municipal
waste stream in the world.
The eVOLV process is the first of its kind to safely reclaim base and precious metals at a large
scale with a 98 percent recovery rate and virtually zero waste. The system consists of three process
tools and a series of chemistries. It operates at or near room temperature and uses very little
energy. It processes printed wiring boards, cell phones, and integrated circuits, or computer chips.
Traditional shredding or grinding of boards, which leads to the loss of precious metals and/or the
formation of dangerous contaminants, is eliminated. The chemistries are engineered for selectivity
to dissolve different metals for easy recovery. Each chemistry was designed using the 12 Principles
of Green Chemistry and is less toxic than common orange juice. In addition, each chemistry — and
all process water — can be infinitely reused, generating no waste. All metals recovered are at a purity
of 98 percent or better and can be re-inserted into manufacturing processes.
Acid-Amine
Technologies, Inc.
(AAT)
Advanced
Technology
Inc.
(ATMI), an
Company
21
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AkzoNobel
Functional
Chemicals, LLC
Archroma
Improved Performance and HSE Profile of a Novel
Stimulation Fluid for Oil and Natural Gas Wells
Well stimulation is a process to improve oil or gas well productivity as the well's output
naturally declines. Stimulation typically involves the injection of hydrochloric acid (HC1) or
hydrofluoric acid (HF) based fluids at high pressure into the well. These corrosive acids dissolve
portions of the rock near the well bore and allow more oil or gas to freely flow. "While stimulation
can significantly improve the productivity of a well, safely handling these corrosive acids is a
significant challenge — e.g., HF is a contact poison. Additionally, additives needed to mitigate
the corrosive impact of HC1 further aggravate the safe handling and environmental impact
due to these additives' poor ecotoxicological profiles. Wells at high temperature and pressure
require a greater number and concentration of these additives, further emphasizing the need for
both safe handling and ecotoxicological profiles of the treatments. As wells trend toward off-
shore with higher temperatures and pressures, there are greater health, safety and environmental
considerations and safer stimulation fluids are desired.
Recent lab studies and field applications with a new stimulation fluid based on the chelating
agent GLutamic Diacetic Acid (GLDA) has shown that GLDA can improve oil and gas flow in
carbonate and sandstone petroleum reservoirs. Even at high temperature and pressure, additives
are not needed with GLDA to prevent corrosion of carbon steel or chrome-based well pipes.
Contrary to conventional stimulation fluids used in the industry, GLDA is a biodegradable,
non-toxic and non-hazardous chemical. GLDA was recently recognized by EPAs Design for the
Environment (DfE) program as a safer chemical ingredient and is certified as 58 percent bio-
based by the USD As Bio-Preferred Procurement Program. The successful application of GLDA
in four high temperature gas wells in the Gulf of Mexico resulted in a doubling of production
using this safe and environmentally friendly stimulation fluid based on GLDA.
Earthcolors Technology
Nowadays, all raw materials currently used for the production of textile dyestuff at commercial
scale are derived from petroleum via a complex process of oil extraction, refining, and synthesis.
Archroma is using a key raw material derived from biomass to produce soluble dyestuffs that are
capable of dyeing cellulosic fibers such as cotton, viscose, paper, and Tencel with high strength
and color fastness properties. For this purpose, the term ''biomass" is defined as the residual
product obtained from the usual human crop activities in agricultural and forestry sectors.
Archroma R&D has been working for the past five years on the technology resulting in
two patents: EP 2 527 407 (WO 2012163498) & EP2546310 (WO 2013007358) (patent
pending). Abundant, globally available, and renewable, the different agriculture crop waste is
directly used as raw material and 100 percent transformed to final dyestuffs. A range of six dyes
have been developed at this stage: two dyes are synthetized using 100 percent biomass wrhile the
other four dyes are 90 percent biomass +10 percent petrol due to the limitation of color range
when using 100 percent biomass. The first bulk batches wrere produced in 2013, and the full
range will be available at the end of May 2014. The recent implementation of these dyes showed
equal performance to the conventional dyes using standard and the best available wet processing
techniques.
There are two main benefits for the new technology:
•The massive reduction of the use of aromatic toxic compounds and of the generation of
CO2 in comparison with present known procedures of the petroleum aromatic chemistry. The
technology also eliminates the high environmental risks of oil extraction and further processing;
and
•The use of waste from another industry (circular economy).
22
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1000 Performance Additive: A Sus-
tainable, Pine-Based Additive to Enable High Re-Use of
Reclaimed Asphalt Pavement
In January 2014, Arizona Chemical Co mpany,LLC commercially launched the SYLVAROAD™
RP 1000 performance additive for asphalt pavement. Arizona Chemical produces this new, bio-
based additive from pine trees using a green production process. This product enables Arizona
Chemical's customers in the paving industry to incorporate significantly higher percentages of
reclaimed asphalt pavement in their hot mix asphalt, thus preventing waste and reducing the use
of virgin materials such as aggregate and binder while still maintaining the specified performance
of the pavement. Enabling higher aged pavement recycling not only saves virgin raw materials,
but also makes economic sense due to reduced raw material costs. Arizona Chemical's technology
upgrades a byproduct from the paper pulping industry into a value-added specialty chemical for
improving infrastructure in the United States.
Boegel Surface Activation Technology Suite
The Boegel Surface Activation Technology Suite is an environmentally friendly alternative
to hazardous surface preparation methods for metallic structures. Invented by a team of Boeing
chemists, the process is based on sol-gel condensation polymerization and utilizes tailored molecules
which link metals to resins by covalently bonding with both surfaces and resins in order to create
a strong, durable chemical bond between critical layers. The Boegel Suite includes a number
of related sol-gel formulations that can be used on aluminum, titanium, stainless steel, nickel,
tungsten, and many other alloys. It has been leveraged for painting, bonding, and sealing surface
preparations across the Boeing Enterprise, including commercial, military, and space vehicles.
Hazardous materials that Boegel successfully replaces include acidic and hexavalent chromium —
containing conversion coatings such as Alodine, Phosphate Fluoride, Pasajel 105 and 107, and
Chromic Acid Anodizing. In addition to ridding Boeing manufacturing processes of many major
environmental concerns, Boegel has also simplified work and increased efficiencies in numerous
paint operations, increased performance and durability, reduced chemical inventories, and has
become a key enabling technology for metal bonding and sealing, with improved adhesion and
durability performance.
Cylinderized Phosphine as Safer, More Environmentally
Friendly Alternatives to Traditional Stored Product
Fumigants
Cytec Industries Inc. has developed and commercialized technology for the stored product
fumigation market. Traditional fumigants such as methyl bromide and metallic phosphides have
significant safety and environmental shortcomings in their use, application, and disposal. Methyl
bromide is an ozone depleting chemical and is partially being phased out under the Montreal
Protocol. Metallic phosphide suffers from worker safety and environmental issues created by
the residues. Cytec's cylinderized phosphine products, ECCbFUME (a non-flammable blend of
two percent phosphine and 98 percent CC»2) and VAPORPH^OS* (phosphine fumigant), offer
inherently safer alternatives as they involve less worker exposure and do not significantly impact
the environment. The use of Cytec's cylinderized products for fumigations in 24 hours allows
for greatly expanded use of these products as drop-in replacements for methyl bromide and they
are now being used commercially in a number of 24-hour applications across the United States.
To date, this technology has resulted in an annual global waste reduction of 900,000 pounds of
solid chemical residue and 600,000 aluminum flasks. In addition, this technology has annually
eliminated 620,000 pounds of methyl bromide use and 1,500,000 pounds of metallic phosphide
use globally.
Chemical
Company, LLC
The
Company; Boeing
Research &
Technology
Cytec
Inc.
23
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The Chemical
Company
Structural
Adhesives Improve Automotive Fuel Efficiency and
Emissions
Environmental impact is a central consideration in vehicle development. Since the Kyoto
Protocol, more countries and industries have committed to reducing their greenhouse gas
footprint. In parallel, fuel economy regulations are becoming more stringent and increasing
attention is being paid to vehicle safety. With strong growth in vehicle production projected in
the coming years and a shift of vehicle ownership and road congestion towards emerging markets,
these sustainability aspects are commanding ever increasing attention globally. Reducing vehicle
weight by incorporating lightweight materials has become a key route to improving fuel economy
and reducing greenhouse gas emissions. Automakers today face the additional challenge of
producing lightweight vehicles that also meet consumer expectations and government standards
for safety, comfort, and performance. One of the key requirements for successfully implementing
lightweight materials in vehicles is the selection of effective joining technologies, especially
for dissimilar, lightweight substrates such as high strength steel, aluminum, magnesium, and
composites. BETAMATE"" and BETAFORCE™ structural adhesives enable joining of lightweight
and dissimilar materials, where traditional joining techniques such as welding and riveting have
limited applicability. These structural adhesives also increase load bearing capability, static and
dynamic stiffness, driving and handling characteristics, and optimized ride, leading to improved
safety and crash behavior, longer vehicle life span, and improved durability.
As a result, BETAMATE"" and BETAFORCE™ structural adhesives represent a breakthrough
solution addressing energy and climate change, as well as safety and health — two pressing world
challenges. For example, structural adhesives have enabled 10 kg weight savings per vehicle, which
translates to an estimated 1.8MM gallons of fuel saved and 16.3 MM kg CO2 avoidance for a
typical 100,000 vehicle build program over the five year life of program.
The Dow Chemical
Company
Dow Polymeric Flame Retardant
Polystyrene (PS) foam is widely used as insulation in the building and construction market,
thus it must meet rigorous building code and fire safety performance standards. The Dow
Polymeric Flame Retardant is an innovative technology that is essential for the preservation
of the PS foam insulation industry, which annually produces foam that avoids service lifetime
totals of 1.7 gigatons of CO? equivalent greenhouse gases. With impending global regulation
and restriction of hexabromocyclododccane (HBCD), the incumbent flame rctardant, the PS
foam industry needed an alternative flame retardant that could provide a significantly improved
environmental, health, and safety (EH&S) profile while cost-effectively matching HBCD's fire
safety performance and foam properties and processing performance. The Dow Polymeric Flame
Retardant was scientifically engineered to achieve this set of requirements by using a combination
of chemistry, polymer science, process technology, application know-how, and EH&S expertise.
Success was achieved by designing a flame retardant polymer, which is inherently more sustainable
than small molecule flame retardants, with a controlled stability to survive under foam processing
conditions and specific chemistry designed to release the active flame retardant agent under fire
conditions. The Dow Polymeric Flame Retardant has met the challenge, leading the global PS
foam industry to select it as the new standard flame retardant. This breakthrough technology is
enabling the industry to meet increasingly stringent building and construction energy efficiency
codes while continuing to meet fire safety performance standards.
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FORMASHIELD!MFormaldehyde Abatement Technology
The Dow Chemical
Company
FORMASHIELD™ is a breakthrough polymeric binder technology that abates gaseous
formaldehyde from the surrounding ambient environment. FORMASHIELD™ Binders
incorporate novel technology that imparts smart functionality to interior architectural paints. The
wall of homes and buildings painted with architectural paints incorporating FORMASHIELD'"
are well positioned to abate a carcinogenic pollutant like formaldehyde thereby improving indoor
air quality for occupants.
According to the United States Green Building Council, buildings in the United States
consume 36 percent of the total energy usage and generate 30 percent of all waste. The green
movement is motivated by the desire to conserve energy usage and reduce natural resources
utilized by this market. Consequently, main building codes used in the United States have
made energy codes the priority which increases ''occupant risk of exposures to indoor generated
contaminants." It is believed that this trend of reducing ventilation and sealing buildings has led
to indoor air containing 2-5 times the levels of many outdoor pollutants.
FORMASHIELD™ Binder Technology seeks to address the growing concern over the most
carcinogenic pollutants by enabling an indoor house paint to ameliorate the health and wellness
of occupants in buildings. Additionally, FORMASHIELD™ Polymers help facilitate a more
robust paint film with improved performance properties. This is achieved by means of reactive
cross-linking technology that enhances adhesion and overall paint durability while further
improving the sustainability profile. Commercial paints containing FORMASHIELD'" Binders
are now sold in the United States and are expanding the credibility of green movement products.
It is expected that FORMASHIELD'™ Technology will become a standard feature in common
commercial paints in the United States whereby formaldehyde reductions provide improved
health and wellness benefits for residents in homes and offices.
SOLDERON™BP Lead-free Solder Plating Chemistry
SOLDERON BP products eliminate lead in advanced semiconductor packaging applications,
such as solder bumping and pillar capping. SOLDERON BP tin-silver plating chemistries provide
electrical and mechanical connections that are equivalent to industry-standard lead-based solder.
Bumping is an advanced wafer level process technology where solder "bumps" or "balls" are
formed during wafer processing. These bumps, formed before the wafer is diced into individual
integrated circuits, will ultimately electrically and mechanically connect the die and the substrate
together into a single package. Solder bumps are deposited using electroplating, and the process
must produce very uniform bumps in terms of size and composition. Electronics manufacturers
use them to join semiconductors together, to a substrate, or directly to a circuit board in flip chip
or controlled collapse chip connection (C4) packaging.
Solder is a critical element in electronics and must provide connections that are durable and
reliable. Tin-lead is an ideal solder because it is malleable and has a low melting point. It has
been used for decades and much of the electronics infrastructure was designed around it. Tin
is combined with lead to provide greater tensile and shear strength and higher conductivity.
The combination resulted in an ideal balance of electrical and thermal conductivity and cost.
Regulations limiting lead have been enacted due to its high toxicity, especially when electronics
reach end of life and are deposited in landfills or recycled.
Materials suppliers have spent most of a decade searching for a lead-free chemistry to
match the reliability of tin-lead solders and tin-silver has emerged as the most viable solution.
Technology is what differentiates Dow's SOLDERON BP tin-silver — patented additives that
provide manufacturers with superior performance and low cost of ownership, which will drive
wider adoption of lead-free solders in electronics.
The Dow Chemical
Company
25
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The Chemical
Company
Solutions
Sustainable Microbial Control Treatments for Hydraulic
Fracturing
The sustainability of hydraulic fracturing operations is of vital concern to the United
States. Chemistry is a critical factor in the success of hydraulic fracturing, enabling technology
breakthroughs and allowing energy producers to maximize well performance and hydrocarbon
quality. To successfully advance sustainable hydraulic fracturing, enabling chemistries must be
designed to not only improve performance, but also improve the safety and environmental impact
of the fracturing operation.
The use of microbial control agents is critical for sustainable operations, ensuring the
minimization of biogenic hydrogen sulfide and acid production. Hydrogen sulfide causes
corrosion, hydrocarbon souring, and, most critically, is a human exposure health concern.
Therefore, effective microbial control is required to ensure worker and public safety, asset integrity,
and to preserve the quality of hydrocarbons, resulting in reductions in overall drilling, re-work,
and re-fracturing.
The safety and environmental impact of chemicals used in hydraulic fracturing, including
microbial control agents, are often of critical concern to the industry and public. To date, attempts
to introduce chemistries or technologies perceived as less harmful have not proven to be effective.
Therefore, the Dow Chemical Company purposely and systematically designed and developed
a microbial control program that enables the advancement of sustainable hydraulic fracturing
operations. This program is based on innovative, sustainable chemistry to dramatically reduce
the environmental impact of current technologies, ensure worker safety, and improve overall
effectiveness of microbial control. The new patent-pending treatment, utilizing glutaraldehyde
and 4,4-dimethyloxazolidine in synergistic combination, provides enhanced microbial control at
lower dosage with excellent biodegradability and low environmental toxicity to offer advanced
treatment of fractured reservoirs. Proven performance in lab and field testing has been validated
through rapid commercial adoption of this chemistry. The implementation of this technology
enables improved asset integrity and improved quality of hydrocarbon production, thus reducing
the overall environmental footprint of hydraulic fracturing.
G-Cleariw Line of Green Cleaning Products Designed to
Clean Hydrocarbons Safely and Effectively
In all industries that deal with cleaning hydrocarbons, maintaining profitability while ensuring
safety of people and the environment are top priorities. Increasing regulations, media attention,
public perspective, fears of climate change, and water and energy conservation are only adding
to the importance of staying ahead of the curve on how companies approach production and
maintenance.
G-Clean*'1 combines domestically sourced renewable feedstocks with proprietary technologies
molded around the multiple green ideologies including biodegradable, recyclable, renewable, and
environmentally safe as well as being commercially viable. G-Clean* offers companies effective
and environmentally safe cleaning products that substantially lower their carbon footprint but
ultimately offers companies a lower cost of cleanups or an increase in revenues (sometimes both).
Each of the products in the G-Clean* product line is based on proprietary colloidal chemistry
processes at the nanoscalc. Food grade ingredients, such as soy, corn, grain, potatoes, and trees arc
processed to form a particle called a micelle. Micelles work to breakdown long chain hydrocarbon
bonds in fats, oils, and grease and hold them in suspension when mixed with water. Ultimately,
the wash off is completely biodegraded by bacteria resident in the crude oil.
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G-Clean'RI, developed by Inventek, all have "zero" ratings according to National Fire Protection
Association: zero reactivity, zero flammability, zero health hazard, and no special hazards. These
100 percent biodegradable and non-toxic products can be used instead of solvents and other
hazardous materials like dicscl that are commonplace when cleaning oil. G-Clean® cleaners in
their organic form are sate for the skin, the air, water, animals, and ground.
According to studies done in the oilfields of E&B Natural Resources and other oil companies,
G-Clean'8' has proven to reduce water needed to clean a typical storage tank by over 50 percent.
Therefore, waste disposal is also reduced substantially. G-Clean'*' is listed on the EPA National
Contingency Plan list and was highlighted as being successful in the BP Deepwater Horizon
cleanup. Other industry validations have come from the Oil & Gas Awards, the Louisiana Gulf
Coast Oil Exposition ''spotlight on new technology award," as well as winning a "Pollution
Prevention" awrard from Kern County (California) Green Awards.
Eastman Omnia MSolvent — Changing the Chemistry of
Clean, New, Safe, Highly Effective Solvent for Cleaning
Applications
To enable development of cleaners that are safer for humans and the environment, cleaning
product formulators need safer ingredients. It is rare, however, for a solvent used in cleaning
products to be sate for people, the environment, and surfaces being cleaned - and still enable
efficient cleaning and compliance with air quality requirements. With this in mind, Eastman
developed a solvent offering an exceptional combination of safety, performance, and value
throughout the industry - from formulators to cleaning staff to customers.
With thousands of molecules under consideration, Eastman narrowed the solvent universe
using computer modeling based on human health and environmental safety criteria and specific
physical/chemical properties to predict good performance. The minimum safety criteria for
candidates were based on EPA's DfE Solvent Screen.
The final candidate, Eastman Omnia™ solvent, has an excellent safety profile, as evidenced
by meeting DfE's Solvent Screen criteria, listing in GreenBlue's CleanGredients'K database with
no restrictions, and inclusion in DfE's Safer Chemical Ingredients List with highest rating.
Performance testing demonstrates Omnia's excellent cleaning ability: neutral-pH formulations
with Omnia™' were highly effective at cleaning and outperformed competitive alternatives.
Prior to making Omnia'™ commercially available, Eastman satisfied requirements for TSCA
Inventory listing and began its first commercial manufacture of Omniav in October 2013.
Shortly thereafter, the first sales of Eastman Omnia1™ solvent were made.
Omnia'™ has a unique chemistry that offers an exceptional combination of performance, safety,
and value. Effective in a variety of light- and heavy-duty cleaners formulated at neutral pH,
Omnia™ works on a wide range of soils—from greasy dirt and tar to soap scum. The combination
of powerful cleaning and excellent safety profile makes it an excellent choice for formulators
challenged to comply with increasingly stringent safety, regulatory, and market demands. Eastman
Omnia™ solvent is changing the chemistry of clean.
Environmentally Preferable Biocide for Water Treatment in
Hydraulic Fracturing
In the past years, unconventional oil and natural gas production has steadily increased in the
United States. Driven by the development of new technologies such as horizontal drilling and
hydraulic fracturing, shale gas has led to major increases in reserves of oil and natural gas. During
hydraulic fracturing, wrater and chemicals are injected, at high pressure, into the geologic formation
Eastman Chemical
Company
Ecolab
27
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Ecolab
Genentech, Inc.
to increase the fractures in the rock layers and allow hydrocarbons to flow. Because large
quantities of water are used during this process, the need tor water treatment and reuse has
become critical. Water treatment prevents the introduction of microorganisms in the formation,
which can result in problems such as reservoir souring, biofouling and microbiologically induced
corrosion. Additionally, facilitating the reuse of produced water through cleaning reduces the
constant demand for fresh water. Based upon these concerns, Ecolab has developed an improved
formulation of the oxidizing biocide peracetic acid (PAA). This chemistry shows superior
results when compared to other conventional biocides (e.g., glutaraldehyde, chlorine dioxide),
including faster and persistent microbial kill, water cleanup properties, solids dropout, and less
corrosion. Importantly, PAA had no adverse effects on other chemistries present in the hydraulic
fracturing fluids, such as friction reducers and scale inhibitors. Ecolab's peracetic acid biocide is an
environmentally preferable chemistry as it breaks down into innocuous components, water and
acetic acid (e.g., vinegar).
A concern associated with hydraulic fracturing is impacts on surface water quality. Ecolab's
EC6734A percetic acid biocide enables the reuse of produced water brine, reducing fresh water
draw. Use of this biocide facilitates safe, cost-effective, onsite water disposal by minimizing
emissions, and reduces plugging by controlling biological growth and thus maintaining hydraulic
conductivity. These benefits contribute significantly to better quality and management of surface
waters.
Environmentally Responsible Spore Control Program
through Effective Cleaning and Sanitizing of Heat Exchange
Dairy Process Equipment
Explosive population growth, massive growth of technology, and accelerating change is
occurring globally. For example; between I960 and 2010, global population has increased two-
fold, the economy seven-fold, food consumption three-fold, water use three-fold, and fossil fuel
use four-fold. Food is one resource lost throughout the supply chain. The recent FAO (Food and
Agricultural organization of the UN) study reports that roughly one third of food produced for
human consumption is lost. This waste is compounded by lost resources (e.g., water and energy)
associated with food production.
In this context, production methods such as Ecolab's novel spore control program that minimize
water and energy requirements while producing safe high quality food that is free of spoilage-
inducing contaminants is an important step forward. To meet current and future demands, food
must be able to be efficiently processed without waste while leveraging renewable energy and
working with a minimum amount of water that can be reused or recycled.
The Ecolab spore control program combines technologies described in two separate patents
to solve a very difficult food and beverage manufacturing problem. This novel cleaning and
sanitizing process employs environmentally responsible biocides that decompose to organic
acids and water after reaction and dilution. Given this positive environmental profile, it is even
more surprising that this product effectively kills themophilic spores, which are among the most
resistant living organisms. Commercialization of these patented technologies enhances food
security by enabling products suitable for direct human consumption, increasing the value of the
product, and bolstering the economic sustainability of producers in the United States.
Targeted Chemotherapy for Solid Tumor Cancer Treatment
Kadcyla® (INN: trastuzumab emtansine) is an antibody drug conjugate approved by the
FDA tor treatment for HER2-positive metastatic breast cancer patients who have received prior
treatment with Herceptin® and a taxane chemotherapy. Antibody drug conjugates combine the
targeting capabilities of antibodies with the potency of chemotherapy. Kadcyla®', specifically, links
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trastuzumab, a monoclonal antibody that binds to HER2-positive cancer cells, via a stable
linker to DM1, an antimicrotubule agent that blocks cell growth by stopping cell division. In
clinical studies, patients treated with Kadcyla* lived nearly six months longer and lived over
3 months longer without their cancer getting worse compared to the standard treatment. In
addition, fewer patients who received this medication experienced severe (>grade 3) adverse
events. Environmental studies have shown that Kadcyla* is readily degradable (84 percent in
28 days). In wastewater treatment facilities, the antibody portion of the conjugate is readily
degraded leaving the linker-DMl (MCC-DMl) portion of the molecule. Ready and inherent
biodegradation tests have shown that MCC-DMl is not toxic to activated sludge bacteria nor
does it bioaccumulate, thus Kadcyla®' does not pose a pharmaceutical in the environment risk.
Kadcyla'8' has been shown to be less toxic to patients than the standard treatment (as defined
by the number of adverse events experienced) because it delivers the chemotherapeutic agent
directly to the cancer cells. Additionally, Kadcyla® is biodegradable and does not bioaccumulate.
Antibody-drug conjugate technology generally has the potential to reduce the amount of
toxic agents used in the clinic as these therapeutics provide a targeted alternative to systemic
chemotherapy dosing.
Low Global Warming and Energy Efficient Polyurethane
Foam Insulation Blowing Agent
Solstice® Liquid Blowing Agent (LBA) (l-chloro-3,3,3-trifluoropropene) has a Global
Warming Potential (GWP) that is 1,000 times lower than the hydrofluorocarbons (HFCs) it is
designed to replace, is non-flammable, non-toxic, non-ozone depleting, and classified by EPA as
VOC exempt. Honeywell's extensive testing proves that Solstice® LBA is more environmentally
friendly, safer, more energy efficient, and more cost-effective to implement compared to existing
blowing agents such as cyclopentane and HFCs.
Solstice® LBA is being adopted globally in appliances, transport, and construction. It is currently
being used in the United States, European Union, Japan, China, Korea, and India. Whirlpool
started producing refrigerators with Solstice® LBA in 2013- Widespread use of Solstice^'LBA
to replace HFCs in polyurethanc foam applications in the United States alone will result in a
reduction of more than 18M tonnes per year of CO2-equivalent; globally this number would
exceed 67M tonnes according to a Honeywell internal analysis. This new product will not only
help reduce global warming, but it will spur economic growth and job creation in the United
States. The first plant will start production in Louisiana in May 2014, and Honeywell is currently
working on a second, world-scale plant in the United States.
An Innovative Catalytic Intramolecular Asymmetric
Reductive Amination of a Dialkyl Ketone Enables a
Highly Efficient, Green Synthesis ofSuvorexant (MK-4305)
A highly efficient and environmentally responsible synthesis of suvorexant has been discovered
and demonstrated. Suvorexant is a new treatment for insomnia which is currently under review in
a number of countries. The first scalable route to the molecule was based on a classical resolution,
and used to prepare material for early drug development. Although this approach could have
been the basis of a viable manufacturing process, it did not meet Merck's high green chemistry
goals and hence Merck researchers decided to totally revise the synthesis. A highly selective and
previously unprecedented catalytic intramolecular reductive amination reaction of a dialkyl
ketone with an alkyl amine was discovered and used to introduce the challenging stereocenter.
Detailed kinetic studies led to understanding of the reaction mechanism and hence optimization
of catalyst loading, yield, and enantiomeric excess. The fundamental knowledge gained from this
work greatly expands the utility of the reductive amination, a ubiquitous transformation in fine
chemical production, and can be applied to the large scale synthesis of other chiral molecules.
Honeywell
International
& Co., Inc.
29
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Company
Chemicals, a
Division of
d West va co
Corporation
In addition, the entire synthesis of suvorcxant was scrutinized with respect to amount and type
of solvents and reagents used, number of operations and isolations, and process robustness. This
allowed the complete removal of the undesirable solvent dichloromethane and led to a 56 percent
reduction in the amount of waste produced by the process. The technology discovered, developed
and implemented by Merck for the manufacture of suvorexant is an excellent example of scientific
innovation resulting in significant benefits to the environment.
Bt Technology, Transforming Insect Control
Insect pest infestation of crop species have limited food production for centuries. Until the
1990s, chemical insecticides were the most advanced tools for insect control. However, they created
significant challenges, including undesirable environmental consequences, toxic effects against
non-target organisms, and often required repeated applications. The vision of biotechnology as a
solution for these challenges became a reality in the mid-1990s.
Biotechnology means pesticide manufacturing and chemical pesticide applications are needed
less frequently. Unlike traditional pesticide manufacturing, some Bacillus thuringiensis (Bt - a
ubiquitous soil microbe) bacteria contain genes expressing proteins that naturally control insect
pest species. Monsanto used biotechnology to take advantage of the characteristics of these toxins
— Cry (crystal) proteins — combining this knowledge with plant molecular genetics to create
plants that express specific toxins to control crop plant pests by producing the crystal protein
through naturally occurring biological mechanisms within the plants. In addition to reducing the
use of pesticides, the specificity of Cry proteins ensures only target organisms are affected, and
avoids pesticide exposure of humans, animals, and non-target beneficial insects.
5? technology continues to be applied across many plant varieties, increasing yields and reducing
the need for chemical pesticides. All Bt traits in commercial use have been created through the use
ofMonsanto's patented synthetic Bt gene technology, and many of Monsanto's traits developed
using this technology have been licensed to and sold by numerous seed companies. In 2013, three
quarters of all corn and cotton grown in the United States included one or more Bt traits.
Farmers planting insect-resistant crops experience improved safety and health because of
reduced pesticide use, and spending less time applying insecticides. This reduced number of
applications mean fewer containers, less fuel and decreased aerial spraying, and reduced costs per
acre farmed, all benefiting the environment while increasing yields and enhancing farmers' lives.
Evotherm(& Warm Mix Asphalt Technology
Traditional hot mix asphalt paving is a significant source of greenhouse gas emissions. MWV
Specialty Chemicals, a division of MeadWestvaco Corporation, developed Evotherm warm mix
asphalt technology. Evotherm is a unique, bio-based surfactant that enhances the ability of asphalt
mix to be produced at temperatures 60°- 90°F lower than conventional hot mix asphalt. This
reduction in temperature enables plant energy savings of 55 percent, resulting in lower carbon
dioxide (CO?) and nitrogen oxide (NOX) emissions. Since Evotherm was introduced to the
marketplace in 2005, over 50 million tons have been used on United States roadways, creating a
savings of 27 million gallons fuel and 605 million pounds of CO?. The lower temperature asphalt
mix also creates a safer and more pleasant work environment by reducing the temperature of the
mix at the paving site to limit vapor and thermal worker exposure.
Evotherm technology, derived from renewable tall oil fatty acids and distilled tall oil, was
developed by MWV Specialty Chemicals in Charleston, South Carolina as a part of the Innovation
Strategy to support the transportation industry. The technology also allows for increased utilization
of recycled materials. As states seek to maximize transportation funding dollars, utilizing recycled
materials provides economical, high-performance roadways. Evotherm improves the workability
recycled materials, allowing for up to 75 percent more recycled content.
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Amended Silicates^ HgX
Amended Silicates® HgX (AS-HgX) is a non-carbon mercury capture reagent that removes
mercury from coal-fired power plant flue gas, enabling utilities to comply with the EPA's soon-to-
be-implemented Mercury & Air Toxic Standards (MATS). This mineral-based product removes
mercury via a chemical reaction, providing economic and environmental advantages unavailable
with carbon-based products. AS-HgX is currently being used in 14 coal-fired power generation
units.
AS-HgX consists of a bentonite substrate that is amended with a metal sulfide that acts as the
reagent to capture mercury from coal-fire flue gas. A chemical reaction forms mercuric sulfide
on the reaction sites of particle surfaces in flue gas. Mercuric sulfide is the most stable form of
mercury, occurring naturally as the mineral metacinnabar. Mercuric sulfide is extremely insoluble
and does not leach into the environment.
Prior to the availability of Amended Silicates, coal-fired power plants had little choice but to
use carbon-based products (Powdered Activated Carbon — PAC) to remove mercury. However,
PAC contaminates fly ash (a byproduct of burning coal), necessitating landfill burial of millions
of tons of fly ash annually. AS-HgX does not contaminate fly ash thus preserving its resale value
to concrete manufacturers, eliminating landfill disposal, and avoiding an estimated one million
tons annually of CC>2 emissions related to Portland cement production.
AS-HgX removes mercury three times more efficiently than PAC products. Extensive testing
demonstrated that compared to PAC products, AS-HgX provides a 25-50 percent cost savings,
reduced operating expenses and consistent MATS compliance. AS-HgX is non-flammable,
noncorrosive, and compatible with a power plant's existing injection equipment with few or no
modifications.
The carbon footprint for producing AS-HgX is about 90 percent less than that created by PAC
production (a potential reduction in CC*2 emissions of 175,000 metric tons per year if just 10
percent of the market used AS-HgX instead of PAC).
Polyethylene Terephthalate (PET) Derived Polymers for
Coatings
PET is a polymer with a polyester backbone. This class of compounds relies upon a reversible
reaction: the substitution at saturated carbonyl. This reaction is usually accomplished through
elimination of a leaving group that is in most cases water or methanol for industrial production.
This esterification in appropriate conditions can be reversed to go back to the starting raw
material, with different methods existing to do so. For this green chemistry technology, glycolysis
was chosen to reverse the esterification. Using an appropriate polyfunctional glycol, the polymer
is broken down to lower molecular weight portions and, with appropriate stoichiometric
conditions, is possible to leave a hydroxyl active functionality at the end. Those lower molecular
weight fractions can further react with other acids or anhydrides to obtain a new polymer in
which they represent part of the backbone mixing up physical-chemical properties with those of
other raw material. In a process invented by PPG Industries, the final polymer is produced using
the PET as starting raw material with a simple and compact process.
The polymer produced can have multiple characteristics depending on the raw materials and
process chosen. A number of different polymers can be obtained from this process including:
polyester resins, alkyd resins; polyester or alkyd acrylated resins; and urethanc polymers. Many of
these polymers are suitable for use in various coatings chemistries. Currently, the most significant
use of this technology is in the production of a 2K polyurethane primer for use in automotive
refinish coatings. The 2K polyurethane is produced by reaction of a hydroxyl functionalized
polymer with a polyisocyanate to obtain a cross-linked film. While PPG is using the recycled-
PET based polymer in a 2K polyurethane primer paint, there are many other potential uses of this
technology within the coatings industry.
Nowinda
Corporation
Industries, Inc.
31
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The Procter &
Company
and DuPont
Company
Company
Cold-Water Enzyme: Reducing the Environmental
Footprint of Residential Laundry through Low
Temperature Cleaning
Each day, Americans do 123 million loads of laundry. They have become accustomed to a
certain level of cleaning and ease in performing this essential everyday activity. And when it
comes to stain removal, most choose to set their dials to warm or hot to ensure a quality clean.
The research teams at DuPont have invented an entirely new enzyme which allows consumers to
wash their clothes at significantly lower temperatures with dramatically improved performance.
The enzyme helps reduce energy use by 50 percent with each load.
This superior enzyme technology, cold water protease, is available now in Tide Coldwater Clean.
Both companies felt passionate about pursuing because success meant significant environmental
benefits due to the sheer scale of use. Current laundry washing creates 40 million metric tons of
emissions of carbon dioxide. If the loads were cleaned instead in cold water, the energy savings
would reduce those emissions by 80 percent. In other words, that is the equivalent of taking
6.3 million cars from the road, based on annual United States emissions. Use of this cold-water
protease has equivalent performance and stability compared to the traditional technology used.
DuPont's Genencor scientists applied novel protein engineering methods to invent an optimal
protease enzyme that at 60°F matches the cleaning performance of the previous incumbent
generation product at 90°F. Joint commercialization of this breakthrough technology means it
has the potential to become the number one selling engineered enzyme in the world — greening
one of the most common household chores on a macro scale.
STEPOSOl^ MET-lOU: A Bio-Derived, Nonionic
Surfactant Solution for Solvent Replacement: Source
Reduction and Inherently Lower Health Hazards in Hard
Surface Cleaning and Adhesive/Paint Removal
Highly toxic solvents and corrosive formulations represent a health hazard and environmental
concern. There have been, for example, 14 recorded deaths since the year 2000 attributed to
paint strippers formulated with methylene chloride, a suspected human carcinogen. Additionally,
N-mcthyl pyrrolidone raises concerns regarding reproductive hazards. Stepan Company has
recently introduced STEPOSOL8' MET-lOU, an efficient, effective, and low toxicity solution
to these problems. This surfactant, developed through a joint effort with Elevance Renewable
Sciences (ERS), realizes commercialization of ERS' novel bio-derived, unsaturated short-chain
methyl ester to achieve the same level of adhesive and paint removal performance in 5 percent
aqueous formulations as 100 percent solvent-based materials. The unsaturated ester raw material
is produced from renewable feedstocks via Nobel-prize winning metathesis technology that
generates 50 percent less greenhouse gases.
The performance of this groundbreaking surfactant stands in stark contrast to previously
available green solvent options. The cleaning power of a solvent is often measured through its
Kauri Butanol value. In external labs, STEPOSOL® MET-10U scored > 1,000 on this scale while
d-limonene, a weaker green alternative solvent, rated a 67. STEPOSOL® MET-lOU is 75 percent
renewable, non-VOC (boiling point = 297°C), non-flammable, less toxic, readily biodegradable,
effective in aqueous solution at more neutral pH than current formulations, and cost-effective
in use. The performance of STEPOSOL*' MET-lOU is attributable to its metathesis-enabled
double bond, its derivatization as an amide, and its wide ranging formulation compatibility.
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STEPOSOL® MET-10U is the first of a new generation of bio-derived, high-performance
chemicals that Stepan Company and joint development partner ERS have brought to both
commercial and consumer markets as an alternative to less sustainable and more hazardous
chemicals. In this manner, Stepan is providing superior performance while also delivering source
reduction and inherently lower hazards to workers, consumers, and the environment.
A Novel High Efficiency Process for the Manufacture of
Highly Reactive Polyisobutylene (PIB) Using a Fixed Bed
Solid State Catalyst Reactor System
Polyisobutylene (PIB) is an isobutylene polymer containing one double bond per polymer
molecule. In high-reactive PIB, the double bond is at or near the end of the polymer chain
making product more reactive. When the double bond is located at internal positions, PIB is less
reactive, creating low-reactive PIB.
Traditional processes to make high-reactive PIB use a liquid polymerization catalyst. The
catalyst is continually fed to the reactor and mixed with isobutylene monomer. The liquid catalyst
is toxic, hazardous, and requires special handling systems and procedures to avoid exposure
and vapor release. As the reaction mixture leaves the reactor, the catalyst must be immediately
neutralized and separated. The separation process involves washing the neutralized catalyst
complex from the reaction mixture with copious amounts of water to remove all catalyst residues.
Trace amounts are corrosive to subsequent processing steps and detrimental to product quality
and stability. Neutralized catalyst cannot be recycled. This process substantially increases plant
capital investment, increases operating costs, and generates approximately as much wastewater
as product.
Soltcx's new process is based on a novel solid catalyst composition using a fixed bed reactor
system. A solid catalyst, in the form of a bead or other convenient geometrical shapes and sizes,
is packed into a tubular reactor to form a stationary, completely contained bed. Isobutylene
monomer is fed to the reactor at a controlled rate and passes over the solid catalyst allowing
polymerization reaction to occur. The polymer mixture exits the reactor at the same controlled
rate. This reactor effluent contains no catalyst residues, therefore no subsequent catalyst separation
or water wash is required.
The Soltex process, using this solid catalyst composition, produces high yields of high purity
product through a simplified, highly efficient operation with substantially reduced capital
investment, low operating and catalyst costs, and no waste generation.
Green Detergents for Industrial Laundries
Since 2005, Washing Systems made the commitment to develop washing chemistry for
industrial laundries across the United States that would enable customers to improve their
environmental profile and financial well-being. This endeavor began in 2007, through the
company's voluntary phase out of nonylphenol ethoxylates (NPEs) in laundry detergents, a known
endocrine disrupter and toxic chemical. Through diligently incorporating strict success criteria,
consisting of formulating a more environmentally friendly detergent capable of reaching the same
quality, chemical usage, and cost for the customer, Washing Systems efficaciously eliminated
NPEs from the laundry formulations. In addition, the new formulations (industrial and two
linen detergents) were developed without the addition of other harmful chemical of concern.
From the projects inception, Washing Systems customers have reduced over 21.6 million pounds
(an average of 3.6 million pounds/year) of NPEs discharged into the environment.
Synthetic Oils
Lybricants of
Inc.
LLC
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Inc.
In order to fully align with Washing Systems new corporate commitment, the three new detergents
were submitted for DfE recognition and approved in 2008. As part of this new partnership with
DfE, Washing System continued to evaluate alternate chemistry to create the best products and
further reduce the environmental impact for all customers. This initiative and desire has led to the
development of another Dffi-recognized detergent in 2009, Pinnacle Liquid Detergent, and two
additional products in 2013 (Spectrum and Supreme).
i An Application of Hybrid Multispectral Analysis:
Real-Time Wastewater Chlorine Pacing Control
Hybrid Multispectral Analysis (HMA) is a unique combination of advanced optical, photonic,
and statistical technologies applied to the challenge of providing synchronized high frequency
data for complex water matrixes. Such information is required for real-time treatment process
control. HMA allows plants to continuously adjust treatment based on current and on-line
historical data to eliminate over and under treatment, provide real-time water security, and enable
closer compliance with and more effective enforcement of environmental laws.
HMA utilizes a single optical probe to conduct over 3-3 million in situ measurements per day,
collecting direct molecular data on absorption, reflectance, and fluorescence. Molecular data is
used to virtually instantaneously quantify critical water quality parameters such as biochemical
oxygen demand (BOD), chloramine, chemical oxygen demand (COD), E. coli, fluorescent
dissolved organic matter (FDOM), NH3, NO:3, specific UVabsorbance (SUVA), trihalomethanes
(THMs), total Kjcldahl nitrogen (TKN), total organic carbon (TOC), total free chlorine
(HOC1+OC1-), pH, total suspended solids (TSS), mixed liquor suspended solids (MLSS), and
turbidity; ranging from ppb to over 10,000 ppm. Approximately every two minutes, parameter
values and/or control signals are broadcast for real time control of processes that determine the
chemical load or energy consumption of a plant and quality of water it discharges, such as chlorine
injection, UVlamp settings, aeration blower speeds, or nutrient injectors; or to stop pumps when
water security parameters are violated.
Green aspects of HMA are that it eliminates reagents, eliminates sample preparation and
storage, minimizes treatment guard bands used to compensate for delays in conventional data,
and requires only 72 watts to operate. HMA is sold under the trade name LiquID™, where
over 65 LiquID"" stations shipped to date have proven useful in the fields of municipal water,
wastewater treatment, water reuse, and industrial process control. The HMA methodology was
developed through support in part by EPA, Office of Naval Research, Oregon State University,
and Oregon Nanoscience and Microtcchnologics Institute.
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are
A S LLC
Pathex1'IPathShield™ Antimicrobial Filter Media for the Control of Bacteria in
Stormwater and Industrial Process Waters 15
Inc. (AAT)
SAFEN: A Low Cost Nematicide and Fungicide That is Generally Regarded as Safe by the
FDA, Which Biodegrades into Two Naturally Occurring Substances, with No Lasting
Detrimental Effects to Air, Soil, and Water 21
AGFA Inc.
A Greener, Safer and More Energy Efficient Antifreeze 15
Inc. (ATM1), an
Company
The eVOLV""' System, a Clean, Sustainable Solution to Electronic Waste 21
LLC
Improved Performance and HSE Profile of a Novel Stimulation Fluid for Oil and Natural
Gas Wells 22
*Amyris
Farnesane: a Breakthrough Renewable Hydrocarbon for Use as Diesel and Jet Fuel. . .... 4
Earthcolors Technology 22
LLC
SYLVAROAD™RP 1000 Performance Additive: A Sustainable, Pine-Based Additive to
Enable High Re-Use of Reclaimed Asphalt Pavement. .......................... 23
Atsumi, of of
California-Dawis
Green Biological Production of Short and Medium Chain Esters ................... 9
Bay LLC
Consumer Viable and Environmentally Friendly Solvent Replacements Developed From
Food Grade Compounds 16
The of
The Scalable Production of Edge-Functionalized Few Layer Graphene Oxide.......... 9
35
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The &
Boegel Surface Activation Technology Suite. ................................. 23
& Technology; The
Boegel Surface Activation Technology Suite 23
of of J.
Voorhees
Bacteriophage-Based Bacterial Identification and Antibiotic Resistance Test.......... 13
Inc.
Novel, Effective, Safe Delivery System for Antimicrobial Agents Derived from Sustainable
Vegetable Monoglycerides 16
Inc.
Cylinderized Phosphine as Safer, More Environmentally Friendly Alternatives to Traditional
Stored Product Fumigants 23
The
BETAMATE™ and BETA FORCE'"1 Structural Adhesives Improve Automotive Fuel
Efficiency and Emissions 24
The
Dow Polymeric Flame Retardant......................................... 24
The
FORMASHIELD™ Formaldehyde Abatement Technology....................... 25
The
SOLDERON'" BP Lead-Free Solder Plating Chemistry 25
The
Sustainable Microbial Control Treatments for Hydraulic Fracturing ............... 26
A.f of
of
Enzyme-Free Biomass Depolymerization Using GVL 10
The &
Cold-Water Enzyme: Reducing the Environmental Footprint of Residential Laundry
through Low Temperature Cleaning 32
G-Clean® Line of Green Cleaning Products Designed to Clean
Hydrocarbons Safely and Effectively....................................... 26
36
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Eastman Omnia™ Solvent- Changing the Chemistry of Clean. New, Safe, Highly Effective
Solvent for Cleaning Applications 27
Ecolab
Environmentally Preferable Biocidefor Water Treatment in Hydraulic Fracturing. . .... 27
Ecolab
Environmentally Responsible Spore Control Program through Effective Cleaning and
Sanitizing of Heat Exchange Dairy Process Equipment 28
of
of California-Los
Catalytic Cross-Couplings Using a Sustainable Metal and Green Solvents. ........... 10
Inc.
Targeted Chemotherapy for Solid Tumor Cancer Treatment 28
Jeffrey Pyun, of Chemistry &
of
Utilization of Elemental Sulfur as a New Chemical Feedstock for Polymeric Materials . . 12
Naturama—Oil Surfactant, Green Degreaser, and Cleaner. ..................... 16
of
of Yang,
LignoCarbon
Green Approaches of Nanocomposite Material Synthesis for Energy Storage, Environmental
Surveillance and Sustainable Food Systems / /
H-O-H Inc.
Cooling Tower Water Conservation & Chemical Treatment Elimination ............ 17
Low Global Warming and Energy Efficient Polyurethane Foam Insulation
Blowing Agent[[[ 29
High Performance Solvent-Free Coating Technology ........................... 17
LignoCarbon, Yang; of
of
Madison
Green Approaches of Nanocomposite Material Synthesis for Energy Storage, Environmental
Surveillance and Sustainable Food Systems 11
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& Co., Inc.
An Innovative Catalytic Intramolecular Asymmetric Reductive Amination of a Dialkyl
Ketone Enables a Highly Efficient, Green Synthesis ofSuvorexant (MK-4305) 29
Bt Technology, Transforming Insect Control ................................. 30
Musolino, Bryan, University of Tennessee-Knoxville
Ultrasound Induced, Copper Mediated Homo-Coupling Using Polymer Supported
Aryltrifluoroborates 11
a of
Corporation
Evotherm® Warm Mix Asphalt Technology 30
LLC
AirCarbon: Carbon-Negative Plastic Made from Greenhouse Gas 18
of
Highly Efficient and Practical Monohydrolysis of Symmetric Diesters 12
Amended Silicates® HgX 31
PPG Inc.
Polyethylene Terephthalate (PET) Derived Polymers for Coatings. ................. 31
The &
Cold- Water Enzyme: Reducing the Environmental Footprint of Residential Laundry
through Low Temperature Cleaning 32
Pyun, of
& of
Utilization of Elemental Sulfur as a New Chemical Feedstock for Polymeric Materials . . 12
Vision, Inc.
Greener Qiiantum Dot Synthesis for Energy Efficient Display and Lighting Products 6
Inc.
Disruptive 1,1-DisubstitutedAlkene (1,1-DA) Green Chemistry Platform, Step Change in
Manufacturing: Breakthrough High Performance, Energy Efficient, Sustainable and Green
Polymer Platform to Transform Industrial Manufacturing 18
38
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Inc.
Tailored Oils Produced from Microalgal Fermentation .......................... 5
*The
RE-HEALING™ Foam Concentrates—Effective Halogen-Free Firefighting 7
*Stahl, S.f of
of
Aerobic Oxidation Methods for Pharmaceutical Synthesis 3
STEPOSOL® MET-10U: A Bio-Derived Nonionic Surfactant Solution for Solvent
Replacement: Source Reduction and Inherently Lower Health Hazards in Hard Surface
Cleaning and Adhesive/Paint Removal. 32
of
A Novel High Efficiency Process for the Manufacture of Highly Reactive Polyisobutydene
Using a Fixed Bed Solid State Catalyst Reactor System 33
Inc.
CIRKIL Biopesticide. ................................................. 19
of
Highly Efficient and Practical Mono hydro lysis of Symmetric Diesters ............... 12
Uniwersity of Arizona, of Chemistry & Biochemistry,
Utilization of Elemental Sulfur as a New Chemical Feedstock for Polymeric Materials . .12
of California-Dawis, of
Green Biological Production of Short and Medium Chain Esters 9
of California-Los of
Catalytic Cross-Couplings Using a Sustainable Metal and Green Solvents. ........... 10
Uniwersity of California-liwerside, of
E.
f/C7? Co-Solv Technology Achieves Unprecedented Yields of Fuel Precursors from
Lignocellulosic Biomass............................................... .14
The Uniwersity of
Scalable Production of Edge-Functionalized Few Layer Graphene Oxide 9
39
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of
Ultrasound Induced, Copper Mediated Homo-Coupling Using Polymer Supported
Aryltrifluoroborates. .................................................. 11
*Uni¥ersity of of
S.
Aerobic Oxidation Methods for Pharmaceutical Synthesis ....................... .3
University of Wisconsin-Madison, of
Yang,
LignoCarbon
Green Approaches of Nanocomposite Material Synthesis for Energy Storage, Environmental
Surveillance and Sustainable Food Systems. ................................. 11
of of
A.
Enzyme-Free Biomass Depolymerization Using GVL 10
Virginia Tech, of
Yi-Heng
High-Yield and High-Purity Hydrogen Production from Carbohydrates via Synthetic
Enzymatic Pathways 14
J.f of of
Mines
Bacteriophage-Based Bacterial Identification and Antibiotic Resistance Test 13
LLC
Green Detergents for Industrial Laundries ................................. .33
Wyman, Charles E.f of Chemical Enwironmental
of
UCR Co-Solv Technology Achieves Unprecedented Yields of Fuel Precursors from
Lignocellulosic Biomass............................................... .14
Yang, Jiang,
of of
Madison
Green Approaches of Nanocomposite Material Synthesis for Energy Storage, Environmental
Surveillance and Sustainable Food Systems. ................................ .11
ZAPS Inc.
An Application of Hybrid Multispectral Analysis: Real-Time Wastewater Chlorine Pacing
Control 34
40
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Yi-Heng of
Virginia
High-Yield and High-Purity Hydrogen Production from Carbohydrates via Synthetic
Enzymatic Pathways 14
39
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Printed on 100% recycled/recyclable paper with a minimum 50% post-consumer waste.
&EPA
Office of Pollution
Prevention and
Toxics (7406M)
744F15002
October 2015
www.epa.gov
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