Award Categories and Winners:
Business Award: Dow AgroSciences and PPG Industries
Academic Award: Dr. Philip Savage (University of Michigan) and Dr. Yinlun Huang (Wayne State University)
Education Award: Grand Valley State University – Chemistry Department
Public Award: Ecology Center
Student Award: Nathan Craft (Grand Valley State University)
Spinetoram: Enhancing a Natural Product for Insect Control
Spinetoram is the active ingredient in a series of insecticides formulated by Dow AgroSciences, a subsidiary of The Dow Chemical Company (“Dow”). Spinetoram is a mixture of chemically modified spinosyns J and L. Spinetoram (XDE-175) results from a goal to create a new spinosyn insecticide that is more effective than spinosad but maintains spinosad’s low toxicity to mammals and other non-target organisms, short environmental persistence, and minimal effects on beneficial arthropods.
The research effort to discover and develop spinetoram was conducted at many locations in the United States and in other countries around the world. However, one critical aspect of the project, the research required to develop an efficient manufacturing process, was conducted entirely in Michigan.
Because of its high level of efficacy against insect pests, low toxicity, and low environmental impact, spinetoram has direct benefits for Michigan farmers. Agriculture and related activities are a significant part of Michigan’s economy, accounting for almost 20% of economic value and 24% of the workforce. Spinetoram products (Delegate™ WG and Radiant™ SC) are registered for use to control many important insect pests on a wide range of crops, including apples, blueberries, grapes, peaches, strawberries, cherries, asparagus, beans, carrots, celery, sweet corn, cucumbers, onions, peppers, potatoes, squash, and tomatoes. These crops account for 78% ($2.6 billion) of the total value of crops produced in Michigan in 2007. An additional benefit that spinetoram provides to Michigan’s economy is the production of spinosyns J and L, the starting materials for spinetoram. All spinetoram sold in the U.S. and around the world is derived from these starting materials – produced only in Dow AgroSciences’ Harbor Beach fermentation production facility.
- Press release from Dow Chemical on winning the Business Award for the 2009 Michigan Green Chemistry Governor’s Award Program (October 1, 2009)
Chitosan Enhanced Paint Detackifier GREEN LOGICTM
Ray Schappert, PhD (Director, EMS & Growth Initiatives)
Mike Albu (Research Associate)
Dave Boehmer (Director,Marketing and Technology)
John Boehmer (Manager, Technical Services)
Nang Bui (Product Manager)
GREEN LOGIC™ is a liquid, chitosan-containing, paint denaturant technology that provides an alternative to traditionalmelamine-formaldehyde (a suspect carcinogen) or acrylic acid based chemistries. The unique feature of the GREEN LOGIC™ technology is that it is derived from crab, lobster and shrimp shells that are a waste product of food production. The GREEN LOGIC™ technology has performed as well as and better in some cases than traditional products used in this area while providing significant cost savings and carbon footprint reduction advantages to customers.
Paint denaturants, also referred to as “paint detackifiers,” are added to the water curtain circulating in down draft, water washed paint spray booths to render over sprayed paint non-sticky. In traditional automotive OEM wet paint spraying operations, only 50-80% of the paint is transferred to the vehicle, with the remaining 20-50%being deposited in the air booth stream that is later purified in the circulating water curtain.
The chemicals added to the water curtain detackify, coagulate and flocculate this over sprayed portion of paint allowing it to be later removed from the water in either a continuous or batch process. The currently available melamine-formaldehyde based detackifiers necessarily contain small amounts of residual free formaldehyde, a suspect carcinogen. Further, the acrylic acid based group of paint denaturants are originally derived from ethylene and/or propylene produced during the petroleum cracking process and therefore rely on non-renewable, petroleum-based feed stocks. The pricing of these acrylic acid-based products is therefore subject to the demands of the petroleum market.
All research, development, education, advocacy, and implementation (including sales and marketing) of the GREEN LOGIC™ technology is through PPG Industries, Inc., Troy, Michigan.
- Press release from PPG Industries on winning the Business Award for the 2009 Michigan Green Chemistry Governor’s Award Program (September 25, 2009)
- PPG Industries was also awarded the 2008 Automotive News PACE Award for the GREEN LOGICtm paint detackifier. (PACE Award: Premier Automotive Suppliers’ Contribution to Excellence) Award)
Dr. Phillip E. Savage, PHD, PE (University of Michigan)
Terephthalic Acid Synthesis in High-Temperature Liquid Water at High Concentrations
Phillip E. Savage, PhD, PE (Arthur F. Thurnau Professor, Chemical Engineering Department, University of Michigan)
Dr. Jennifer M. Dunn
Dr. Mitsumasa Osada
This technology replaces a flammable organic solvent with water. It also eliminates the production of methyl bromide pollution (about 25,000 lb/yr/plant) from terephthalic acid synthesis and the need to synthesize about 1 billion lb/yr of acetic acid as make up solvent. Thus, the environmental impacts associated with methyl bromide emissions and the manufacture of this acetic acid can be avoided. The potential global impact of a water-based process for making terephthalic acid is enormous. The investigators also developed and analyzed conceptual chemical process designs for this new reaction medium to show quantitatively that it is competitive on the bases of economics, energy consumption, and environmental impacts. The research also developed processing strategies so that high concentrations, such as those needed for a commercial process, could be used with these greener reaction conditions. Discovering how to get high terephthalic acid yields at high concentrations required extensive and sustained chemical research along with innovative strategies for feeding oxygen to the reactor. The University of Michigan has filed a provisional patent application for this technology and the discoveries have been published in several different peer reviewed chemical journals.
The research has discovered reaction conditions and a reactor strategy for the synthesis of terephthalic acid in high yields and nearly 100% selectivity from catalyzed partial oxidation of p-xylene at high concentrations in high-temperature liquid water. Using water as an alternative medium for this reaction provides many benefits relative to acetic acid, the solvent used commercially. First of all, acetic acid is a flammable solvent whereas water is not. Furthermore, using water would eliminate emissions of the pollutant methyl bromide, which forms in the current process via reactions between acetic acid and the bromide catalysts employed. According to EPA’s Toxics Release Inventory, a single terephthalic acid plant can release about 25,000 lb/yr. Another benefit of using water is a simpler process. A final benefit is solvent stability. When water serves as the reaction medium, there are no oxidative solvent losses. Therefore, the raw material and energy consumption and pollutant emissions associated with producing 109 lb/yr make-up acetic acid would vanish.
- Read more about Dr. Savage and his research in his profile developed as part of the Michigan Educator Profiles series.
Integrated Hazardous Chemical-Metal Near-Zero Discharge Technology for Green and Profitable Design and Operation of Electroplating Processes
Dr. Yinlun Huang, PhD (Professor and Charles H. Gershenson Distinguished Faculty Fellow; Director,Graduate Program; Director, Laboratory for Multiscale Complex Systems Science and Engineering, Department of Chemical Engineering and Materials Science; Co-Director, Sustainable Engineering Graduate Certificate Program, College of Engineering, Wayne State University)
National Science Foundation (Financial)
Environmental Protection Agency (Financial)
American Electroplaters and Surface Finishers Society (Financial)
Michigan Department of Environmental Quality (Financial)
K.C. Jones Plating Company (Financial/Technical)
According to American Electroplaters and Surface Finishers Society, Michigan has approximately 300 small electroplating plants. The plants consume huge amounts of hazardous/toxic chemicals daily for surface treatment and metal deposition on parts. The waste streams from production lines usually contain over 100 regulated chemical, metal, and other contaminants. Today, how to minimize the use of hazardous/toxic chemicals and their loss to the environment, to reduce production cost, and to ensure product quality are the most challenging issues for all the Michigan platers.
Over the past decade, Huang has led his research group to conduct comprehensive studies on hazardous-substance-focused source reduction in the electroplating industry, with a promise of profit generation through technology implementation. The Integrated Hazardous Chemical-Metal Near-Zero Discharge (CheMetNZD) Technology developed by Huang is an integration of two key technologies: (i) the hazardous chemical solvent/acid near-zero discharge technology through designing and operating a Stage-wised Chemical Allocation Network (SCAN), and (ii) the hazardous plating solution near-zero discharge technology through designing and operating a Reversed Electroplating Solution Recover System (RESORS).
The technology was successfully implemented in K.C. Jones Plating Company in 2007, with significant environmental and economic benefits. These include the reductions of hazardous chemical consumption by 8%~100% (depending on the chemicals), the hazardous substances entering to the environment by 83%~92%, and the rinse water by 40%, the plating solution consumption by 20%~45%(depending on the chemicals and metals). The ratio of the annualized profit from the technology to the total annualized cost for using the technology reached 16.8 to 1.
Green Chemistry Integration in the University Curriculum
Chemistry Department, Grand Valley State University:
Dr. Dalila G. Kovacs (Associate Professor of Organic Chemistry)
Dr. Min Qi (Professor of Environmental Chemistry)
Dr. Andrew Lantz (Assistant Professor of Analytical Chemistry)
Dr. Cory DiCarlo (Assistant Professor Analytical Chemistry)
The work addresses the problem of content and methodology in green chemistry education in Michigan. Two green chemistry courses, a green chemistry certification and a strong environmental program place the Chemistry Department at Grand Valley State University (GVSU) at the forefront of green chemistry education in Michigan. As organizers of the 1st Michigan Green Chemistry Education Network conference and the publishers of MIGreen newsletter, we are building the scaffold for a constructive and productive collaboration among institutions, state-wide, to the direct benefit of our students and the quality of future workforce in Michigan. The interest in including Green Chemistry in the GVSU curriculum materialized initially in “Green Chemistry” a special topic class, highly evaluated by the students, resulting in a solid foundation for the new “Green Chemistry & Industrial processes,” a subject permanently introduced in the curriculum. An introductory course, “Pollution Prevention, Green Chemistry and Green Engineering,” was designed via a service contract with Michigan Department of Environmental Quality.
GVSU offers a Bachelor of Science degree with an emphasis in Environmental Chemistry. This tradition, experienced faculty, and available equipment, converged extremely well with the new Green Chemistry courses and led to the inception of a ‘Certification in green chemistry’ program currently under University Curriculum revision, a modality to prepare our graduates for integration into the workforce and to provide them with a competitive edge for the job market. To fill the communication gap among Michigan educators and to share our experience, we organized a network conference, an event that brought together faculty, administrators, businesses and government representatives. The first issue of MIGreen, a newsletter connecting all interest parties in green chemistry education was delivered, it will continue monthly, fostering idea exchange and cooperative projects.
- Offered by the Chemistry Department at Grand Valley State University:
- Certificate in Green Chemistry
- CHM 111 Introduction to Green Chemistry
Advocating for Green Chemistry Policy for Michigan
Mike Garfield (Director)
Tracey Easthope (Environmental Health Director)
Michigan Network for Children’s Environmental Health and member groups
Since 2006, the Ecology Center (the Center) has sought to advance the practice and teaching of Green Chemistry in Michigan by advocating for policy change, educating and mobilizing citizens, participating in multistakeholder initiatives, and building a base of support for Green Chemistry activities among environmental, health professional and health-effected organizations, elected representatives, government agencies, business leaders, educators, private foundations, public institutions and others. The overall goal of the Ecology Center’s Green Chemistry effort is to protect public and environmental health while supporting sustainable economic development. In all our efforts,we are focused on accelerating the timeline for this transformation. Our focus is in five areas:
• Advance efforts state-wide to support industry efforts to design out hazards through the redesign of chemicals, products and processes, synthesis of new safer materials, and through the substitution of safer chemicals and processes
• Advance efforts state-wide to incorporate Green Chemistry into all levels of science education
• Install Green Chemistry as a cornerstone of the State’s economic development strategy and “green” the state’s economic development strategy
• Educate the public and opinion leaders about Green Chemistry and raise the profile of Green Chemistry in Michigan
• Explore a Green Chemistry Institute, technology transfer center or other permanent infrastructure to aid Michigan business and educators in advancing Green Chemistry
To move these objectives forward, the Center has advocated and been an active ambassador for Green Chemistry to business, the public, to academia with the end result of increasing demand and the adoption of Green Chemistry policies, innovations as well as raising awareness to the general public through numerous media and communication tools.
Cyclic Polyols in Transfer Hydrogenation
Cyclic polyols and cyclohexene derivatives were investigated as possible hydrogen donors in transfer hydrogenation reactions. Hydrogenation is a fundamental chemical reaction and a core technology in chemical synthesis, utilizing hydrogen gas or other sources of hydrogen. Frequently applied in industrial settings, hydrogenation is used to obtain a variety of products, from super commodities to specialty chemicals. Our goal was to investigate the effectiveness of various compounds as hydrogen donors and explore the capabilities of functional groups other than alkenes to influence the hydrogen donation abilities of a given structure.
The significance of this project is based on the growing demand for efficient methods of asymmetric transfer hydrogenation and potential hydrogen donors useful in large scale applications. Worldwide the market for fine chemicals sold as single enantiomers was $6.63 billion in 2000 and grew 13.2% annually to over $16 billion in 2007. This strong growth is fueled by the drug industry, followed by agricultural chemicals, chemicals for electronics, flavors and fragrances. Worldwide sales of single enantiomer drugs head past $123 billion. The potential application of our experiments would be significant in that if successful, companies in
Michigan could apply this greener hydrogenation process in their synthesis of specific drugs and other specialty chemicals.