Progress 07/01/21 to 01/31/24
Outputs
Target Audience:This SBIR PhI reached industrial and academic audiences with interest in bio-based polyols. Commercial sectors included apparel, automotive, and consumer goods. Industrial sectors include polyurethane manufacturers, Spandex manufacturers, poly tetramethylene ether glycol manufacturers, and poly trimethylene ether glycol manufacturers. Academics included Iowa State University, SUNY College of Environmental Science and Forestry, the University of Maine, and the University of Wisconsin. Changes/Problems:The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass. An attractive, alternative path to achieving this goal arose during our PhI effort. We began with a focus on competing with the incumbent polyol, poly tetramethylene ether glycol (PTMEG) by making polyols from levoglucosan (LGA). PTMEG is primarily made from petroleum with a carbon intense process. LGA polyols are exclusively made from lignocellulosic biomass. We learned that industrial users seek a drop-in replacement for PTMEG, which LGA polyols are not. LGA polyol customers would face switching costsassociated with process and product redesign. These costs limit the addressable market because they add to the total cost of the LGA polyol. Customer discovery further taught us that cost competitive, non-food, biobased PTMEG is in demand. Cost is the main obstacle in meeting this industrial need. In Ph II we will demonstrate a cost competitive route from hemicellulose to biobased PTMEG. We will develop thermochemical technology that reduces the cost and environmental impact of hemicellulose extraction and conversion to tetrahydrofuran (THF). In Ph I we demonstrated a catalyst to polymerize THF to PTMEG that can significantly reduce cost and reduce chemical waste compared to the incumbent polymerization process. The change from LGA polyols to biorenewable PTMEG aligns our research with the needs of polyurethane and Spandex manufacturers, who are the primary polyol users. Farmers produce lignocellulosic feedstock for biobased PTMEG. These residues are presently sold as animal feed additives for low value. Woody agricultural residue contains hemicellulose plus cellulose and lignin. Only hemicellulose is useful for the PTMEG process, and after the hemicellulose is extracted, the feed is more digestible for ruminants. The digestible feed will be sold for a higher price, and the farmer will gain revenue for the extracted hemicellulose. Designing biobased PTMEG production to benefit the farmer and seamlessly integrating into existing material flows further lowers PTMEG cost. ? What opportunities for training and professional development has the project provided?This SBIR PhI has provided the opportunity to professionally develop the project scientists in the field of non-food, bio-based, industrial chemicals. How have the results been disseminated to communities of interest?In the course of market understanding, and scientific research we have discussed our work with future customers and academics. Almond grower hulling and shelling coops have written letters of support for our Ph II proposal. The core inventions will not be disclosed until patent protection is secured. What do you plan to do during the next reporting period to accomplish the goals?
Nothing Reported
Impacts
What was accomplished under these goals?
This project promotes the use of non-food biobased polyols by developing improved technologies for hemicelluloses extraction, hemicelluloses thermochemical conversion to tetrahydrofuran (THF), and polymerization of THF to polytetramethylene ether glycol (PTMEG.) These technologies will enable domestic, biobased PTMEG that is cost competitive with incumbent fossil fuel derived PTMEG. Farmers will benefit from increased revenue derived from lignocellulosic waste, consumers will benefit from lower carbon intensity products without sacrifice in price or performance. During the second half of the 20th century, biobased PTMEG was manufactured in the US from corn cobs and oat hulls. Today, lower cost fossil fuel based PTMEG has replaced biobased PTMEG. The technical opportunity exists to make biobased PTMEG cost competitive by improving the production processes: xylan extraction, catalytic conversion to THF, and polymerization to PTMEG. Streamlining this value chain will allow the low carbon intensity of biobased PTMEG to disrupt the $4B global PTMEG market, and to reduce CO2 emissions by millions of tons/year. Clean almond shells are currently sold as crude fiber for animal feed. A portion of this flow will be extracted for hemicelluloses and returned as digestible fiber. Operating costs are reduced because biomass collection costs are borne by the almonds, extraction operations can scale from a fraction to the full flow of shells, and the entire biomass is valorized with existing customers and infrastructure. The improved process will produce two streams from the almond shell input: 1) an aqueous solution of >5 wt% hemicelluloses, with >80% xylan yield, and 2) a digestible residual with moisture <12%, pH >5.0, and furan content <0.5 wt%. The extraction equipment can be co-located at the almond shelling facility. There is an opportunity to reduce capital and operating costs by developing a novel catalyst that eliminates unit operations and waste streams. The incumbent THF polymerization technology uses acetic anhydride initiators, acetic acid chain transfer agents, and methanol for transesterification. These inputs and their products must all be removed from the final PTMEG. In Phase I we demonstrated a recyclable, homogenous catalyst that eliminates all these inputs. The incumbent technology has additional unit operations for methanolysis and narrowing that our catalyst does not.
Publications
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Progress 07/01/23 to 08/31/23
Outputs
Target Audience:
Nothing Reported
Changes/Problems:The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass. An attractive, alternative path to achieving this goal arose during our PhI effort. We began with a focus on competing with the incumbent polyol, poly tetramethylene ether glycol (PTMEG) by making polyols from levoglucosan (LGA). PTMEG is primarily made from petroleum with a carbon intense process. LGA polyols are exclusively made from lignocellulosic biomass. We learned that industrial users seek a drop-in replacement for PTMEG, which LGA polyols are not. LGA polyol customers would face switching costsassociated with process and product redesign. These costs limit the addressable market because they add to the total cost of the LGA polyol. Customer discovery further taught us that cost competitive, non-food, biobased PTMEG is in demand. Cost is the main obstacle in meeting this industrial need. In Ph II we will demonstrate a cost competitive route from hemicellulose to biobased PTMEG. We will develop thermochemical technology that reduces the cost and environmental impact of hemicellulose extraction and conversion to tetrahydrofuran (THF). In Ph I we demonstrated a catalyst to polymerize THF to PTMEG that can significantly reduce cost and reduce chemical waste compared to the incumbent polymerization process. The change from LGA polyols to biorenewable PTMEG aligns our research with the needs of polyurethane and Spandex manufacturers, who are the primary polyol users. Farmers produce lignocellulosic feedstock for biobased PTMEG. These residues are presently sold as animal feed additives for low value. Woody agricultural residue contains hemicellulose plus cellulose and lignin. Only hemicellulose is useful for the PTMEG process, and after the hemicellulose is extracted, the feed is more digestible for ruminants. The digestible feed will be sold for a higher price, and the farmer will gain revenue for the extracted hemicellulose. Designing biobased PTMEG production to benefit the farmer and seamlessly integrating into existing material flows further lowers PTMEG cost. ? What opportunities for training and professional development has the project provided?This SBIR PhI has provided the opportunity to professionally develop the project scientists in the field of non-food, bio-based, industrial chemicals. How have the results been disseminated to communities of interest?In the course of market understanding, and scientific research we have discussed our work with future customers and academics. Almond grower hulling and shelling coops have written letters of support for our Ph II proposal. The core inventions will not be disclosed until patent protection is secured. ? What do you plan to do during the next reporting period to accomplish the goals?
Nothing Reported
Impacts
What was accomplished under these goals?
This project promotes the use of non-food biobased polyols by developing improved technologies for hemicelluloses extraction, hemicelluloses thermochemical conversion to tetrahydrofuran (THF), and polymerization of THF to polytetramethylene ether glycol (PTMEG.) These technologies will enable domestic, biobased PTMEG that is cost competitive with incumbent fossil fuel derived PTMEG. Farmers will benefit from increased revenue derived from lignocellulosic waste, consumers will benefit from lower carbon intensity products without sacrifice in price or performance. During the second half of the 20th century, biobased PTMEG was manufactured in the US from corn cobs and oat hulls. Today, lower cost fossil fuel based PTMEG has replaced biobased PTMEG. The technical opportunity exists to make biobased PTMEG cost competitive by improving the production processes: xylan extraction, catalytic conversion to THF, and polymerization to PTMEG. Streamlining this value chain will allow the low carbon intensity of biobased PTMEG to disrupt the $4B global PTMEG market, and to reduce CO2 emissions by millions of tons/year. Clean almond shells are currently sold as crude fiber for animal feed. A portion of this flow will be extracted for hemicelluloses and returned as digestible fiber. Operating costs are reduced because biomass collection costs are borne by the almonds, extraction operations can scale from a fraction to the full flow of shells, and the entire biomass is valorized with existing customers and infrastructure. The improved process will produce two streams from the almond shell input: 1) an aqueous solution of >5 wt% hemicelluloses, with >80% xylan yield, and 2) a digestible residual with moisture <12%, pH >5.0, and furan content <0.5 wt%. The extraction equipment can be co-located at the almond shelling facility. There is an opportunity to reduce capital and operating costs by developing a novel catalyst that eliminates unit operations and waste streams. The incumbent THF polymerization technology uses acetic anhydride initiators, acetic acid chain transfer agents, and methanol for transesterification. These inputs and their products must all be removed from the final PTMEG. In Phase I we demonstrated a recyclable, homogenous catalyst that eliminates all these inputs. The incumbent technology hasadditional unit operations for methanolysis and narrowing that our catalyst does not. ?
Publications
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Progress 07/01/21 to 08/31/23
Outputs
Target Audience:This SBIR PhI reached industrial and academic audiences with interest in bio-based polyols. Commercial sectors included apparel, automotive, and consumer goods. Industrial sectors include polyurethane manufacturers, Spandex manufacturers, poly tetramethylene ether glycol manufacturers, and poly trimethylene ether glycol manufacturers. Academics included Iowa State University, SUNY College of Environmental Science and Forestry, the University of Maine, and the University of Wisconsin. Changes/Problems:The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass. An attractive, alternative path to achieving this goal arose during our PhI effort. We began with a focus on competing with the incumbent polyol, poly tetramethylene ether glycol (PTMEG) by making polyols from levoglucosan (LGA). PTMEG is primarily made from petroleum with a carbon intense process. LGA polyols are exclusively made from lignocellulosic biomass. We learned that industrial users seek a drop-in replacement for PTMEG, which LGA polyols are not. LGA polyol customers would face switching costsassociated with process and product redesign. These costs limit the addressable market because they add to the total cost of the LGA polyol. Customer discovery further taught us that cost competitive, non-food, biobased PTMEG is in demand. Cost is the main obstacle in meeting this industrial need. In Ph II we will demonstrate a cost competitive route from hemicellulose to biobased PTMEG. We will develop thermochemical technology that reduces the cost and environmental impact of hemicellulose extraction and conversion to tetrahydrofuran (THF). In Ph I we demonstrated a catalyst to polymerize THF to PTMEG that can significantly reduce cost and reduce chemical waste compared to the incumbent polymerization process. The change from LGA polyols to biorenewable PTMEG aligns our research with the needs of polyurethane and Spandex manufacturers, who are the primary polyol users. Farmers produce lignocellulosic feedstock for biobased PTMEG. These residues are presently sold as animal feed additives for low value. Woody agricultural residue contains hemicellulose plus cellulose and lignin. Only hemicellulose is useful for the PTMEG process, and after the hemicellulose is extracted, the feed is more digestible for ruminants. The digestible feed will be sold for a higher price, and the farmer will gain revenue for the extracted hemicellulose. Designing biobased PTMEG production to benefit the farmer and seamlessly integrating into existing material flows further lowers PTMEG cost. ? What opportunities for training and professional development has the project provided?This SBIR PhI has provided the opportunity to professionally develop the project scientists in the field of non-food, bio-based, industrial chemicals. How have the results been disseminated to communities of interest?In the course of market understanding, and scientific research we have discussed our work with future customers and academics. Almond grower hulling and shelling coops have written letters of support for our Ph II proposal. The core inventions will not be disclosed until patent protection is secured. What do you plan to do during the next reporting period to accomplish the goals?
Nothing Reported
Impacts
What was accomplished under these goals?
This project promotes the use of non-food biobased polyols by developing improved technologies for hemicelluloses extraction, hemicelluloses thermochemical conversion to tetrahydrofuran (THF), and polymerization of THF to polytetramethylene ether glycol (PTMEG.) These technologies will enable domestic, biobased PTMEG that is cost competitive with incumbent fossil fuel derived PTMEG. Farmers will benefit from increased revenue derived from lignocellulosic waste, consumers will benefit from lower carbon intensity products without sacrifice in price or performance. During the second half of the 20th century, biobased PTMEG was manufactured in the US from corn cobs and oat hulls. Today, lower cost fossil fuel based PTMEG has replaced biobased PTMEG. The technical opportunity exists to make biobased PTMEG cost competitive by improving the production processes: xylan extraction, catalytic conversion to THF, and polymerization to PTMEG. Streamlining this value chain will allow the low carbon intensity of biobased PTMEG to disrupt the $4B global PTMEG market, and to reduce CO2 emissions by millions of tons/year. Clean almond shells are currently sold as crude fiber for animal feed. A portion of this flow will be extracted for hemicelluloses and returned as digestible fiber. Operating costs are reduced because biomass collection costs are borne by the almonds, extraction operations can scale from a fraction to the full flow of shells, and the entire biomass is valorized with existing customers and infrastructure. The improved process will produce two streams from the almond shell input: 1) an aqueous solution of >5 wt% hemicelluloses, with >80% xylan yield, and 2) a digestible residual with moisture <12%, pH >5.0, and furan content <0.5 wt%. The extraction equipment can be co-located at the almond shelling facility. There is an opportunity to reduce capital and operating costs by developing a novel catalyst that eliminates unit operations and waste streams. The incumbent THF polymerization technology uses acetic anhydride initiators, acetic acid chain transfer agents, and methanol for transesterification. These inputs and their products must all be removed from the final PTMEG. In Phase I we demonstrated a recyclable, homogenous catalyst that eliminates all these inputs. The incumbent technology has additional unit operations for methanolysis and narrowing that our catalyst does not.
Publications
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Progress 07/01/22 to 06/30/23
Outputs
Target Audience:This SBIR PhI reached industrial and academic audiences with interest in bio-based polyols. Commercial sectors included apparel, automotive, and consumer goods. Industrial sectors include polyurethane manufacturers, Spandex manufacturers, poly tetramethylene ether glycolmanufacturers, and poly trimethylene ether glycol manufacturers.Academics included Iowa State University, SUNY College of Environmental Science and Forestry, the University of Maine, and the University of Wisconsin. Changes/Problems:The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass. An attractive, alternative path to achieving this goal arose during our PhI effort. We began with a focus on competing with the incumbent polyol, poly tetramethylene ether glycol (PTMEG) by making polyols from levoglucosan (LGA). PTMEG is primarily made from petroleum with a carbon intense process. LGA polyols are exclusively made from lignocellulosic biomass. We learned that industrial users seek a drop-in replacement for PTMEG, which LGA polyols are not. LGA polyol customers would face switching costs associated with process and product redesign. These costs limit the addressable market because they add to the total cost of the LGA polyol. Customer discovery further taught us that cost competitive, non-food, biobased PTMEG is in demand. Cost is the main obstacle in meeting this industrial need. In Ph II we will demonstrate a cost competitive route from hemicellulose to biobased PTMEG. We will develop thermochemical technology that reduces the cost and environmental impact of hemicellulose extraction and conversion to tetrahydrofuran (THF). In Ph I we demonstrated a catalyst to polymerize THF to PTMEG that can significantly reduce cost and reduce chemical waste compared to the incumbent polymerization process. The change from LGA polyols to biorenewable PTMEG aligns our research with the needs of polyurethane and Spandex manufacturers, who are the primary polyol users. Farmers produce lignocellulosic feedstock for biobased PTMEG. These residues are presently sold as animal feed additives for low value. Woody agricultural residue contains hemicellulose plus cellulose and lignin. Only hemicellulose is useful for the PTMEG process, and after the hemicellulose is extracted, the feed is more digestible for ruminants. The digestible feed will be sold for a higher price, and the farmer will gain revenue for the extracted hemicellulose. Designing biobased PTMEG production to benefit the farmer and seamlessly integrating into existing material flows further lowers PTMEG cost. What opportunities for training and professional development has the project provided?This SBIR PhI has provided the opportunity to professionally develop the project scientists in the field of non-food, bio-based, industrial chemicals. How have the results been disseminated to communities of interest?In the course of market understanding, and scientific research we have discussed our work with future customers and academics. Almond grower hulling and shelling coops have written letters of support for our Ph II proposal. The core inventions will not be disclosed until patent protection is secured. What do you plan to do during the next reporting period to accomplish the goals?This report is the final report for Ph I. We have written a Ph II proposal to continue the work.
Impacts
What was accomplished under these goals?
This project promotes the use of non-food biobased polyols by developing improved technologies for hemicelluloses extraction, hemicelluloses thermochemical conversion to tetrahydrofuran (THF), and polymerization of THF to polytetramethylene ether glycol (PTMEG.) These technologies will enable domestic, biobased PTMEG that is cost competitive with incumbent fossil fuel derived PTMEG. Farmers will benefit from increased revenue derived from lignocellulosic waste, consumers will benefit from lower carbon intensity products without sacrifice in price or performance. During the second half of the 20th century, biobased PTMEG was manufactured in the US from corn cobs and oat hulls. Today, lower cost fossil fuel based PTMEG has replaced biobased PTMEG. The technical opportunity exists to make biobased PTMEG cost competitive by improving the production processes: xylan extraction, catalytic conversion to THF, and polymerization to PTMEG. Streamlining this value chain will allow the low carbon intensity of biobased PTMEG to disrupt the $4B global PTMEG market, and to reduce CO2 emissions by millions of tons/year. Clean almond shells are currently sold as crude fiber for animal feed. A portion of this flow will be extracted for hemicelluloses and returned as digestible fiber. Operating costs are reduced because biomass collection costs are borne by the almonds, extraction operations can scale from a fraction to the full flow of shells, and the entire biomass is valorized with existing customers and infrastructure. The improved process will produce two streams from the almond shell input: 1) an aqueous solution of >5 wt% hemicelluloses, with >80% xylan yield, and 2) a digestible residual with moisture <12%, pH >5.0, and furan content <0.5 wt%. The extraction equipment can be co-located at the almond shelling facility. There is an opportunity to reduce capital and operating costs by developing a novel catalyst that eliminates unit operations and waste streams. The incumbent THF polymerization technology uses acetic anhydride initiators, acetic acid chain transfer agents, and methanol for transesterification. These inputs and their products must all be removed from the final PTMEG. In Phase I we demonstrated a recyclable, homogenous catalyst that eliminates all these inputs. The incumbent technology has additional unit operations for methanolysis and narrowing that our catalyst does not.
Publications
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Progress 07/01/21 to 06/30/22
Outputs
Target Audience:This SBIR PhI reached industrial and academic audiences with interest in bio-based polyols. Industrial sectors included apparel, automotive, and consumer goods. Academics included Iowa State University, SUNY College of Environmental Science and Forestry, the University of Maine, and the University of Wisconsin. Changes/Problems:The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass. An attractive, alternative path to achieving this goal arose during our PhI effort. We began with a focus on competing with the incumbent polyol, poly tetramethylene ether glycol (PTMEG) by making polyols from levoglucosan (LGA). We then learned that industrial users seek a drop-in replacement for PTMEG, which LGA polyols are not. LGA polyol customers will face switching costs associated with process and product redesign. These costs limit the addressable market because they add to the total cost of the LGA polyol. Customer discovery further taught us that cost competitive, non-food, biobased PTMEG is in demand. Cost is the main obstacle in meeting this industrial need. In parallel with our NIFA SBIR we are developing thermoplastics based on LGA with National Science Foundation funding. The cost of biobased PTMEG can be significantly reduced by coproducing PTMEG and LGA thermoplastics as they are respectively made from hemicelluloses and cellulose. An alternative path to providing industrial polyols from woody biomass has emerged during PhI. This path uses LGA for thermoplastics rather than for industrial polyols. LGA thermoplastics enables cost effective, biobased PTMEG to be made in a biorefinery that is integrated for production of both PTMEG from hemicelluloses and thermoplastics from LGA. The second reporting period will evaluate both LGA polyols and PTMEG coproduced with LGA thermoplastics as paths toward providing industrial polyols from woody biomass. What opportunities for training and professional development has the project provided?This SBIR PhI has provided the opportunity to professionally develop the directors in the fieldof non-food, bio-based, industrial chemicals. How have the results been disseminated to communities of interest?In the course of market understanding, and scientific research we have discussed our work with future customers and academics. The core inventions will not be disclosed until patent protection is secured. What do you plan to do during the next reporting period to accomplish the goals?We are currently comparing two bio-basedpolyols- one synthesized from cellulose and the other from hemicellulose - to replacefossil fuel basedpolyols with woody biomass based polyols.
Impacts
What was accomplished under these goals?
The PhI specific tasks of synthesizing poly(2,3)glucose expoxide monomers from levoglucosan (LGA) and polymerization of these monomers have been accomplished. The task of characterizing these oligomers is in progress. Through customer discovery we learned about the unmet market need for competitively priced, biobased polyols that are chemically identical to the polyols currently used, i.e. renewable drop-in replacements. Polyols are used at large, industrial scale to make polyurethane (PUR). Industry presently makes PUR comprising up to 70 wt%of a specific polyol, poly tetramethylene ether glycol (PTMEG). PTMEG is largely made from fossil fuel derived acetylene via the Reppe process. Industries that make consumer facing PUR products are eager to purchase cost competitive, non-food, biobased PTMEG. The polyols from LGA developed in this SBIR would compete with PTMEG, but apart from the terminal hydroxyls, LGA polyols and PTMEGare chemically different. LGA based polyols are not drop-in replacements for PTMEG, so market adoption will involve process adaptation and product redesign. Woody biomass based PTMEG was made in the United States in the mid 20th century, but lower cost fossil fuel based PTMEG then displaced the renewable technology. The bio-based PTMEG and fossil fuel based PTMEG are chemically identical; they are drop-in replacements for each other . During PhI we came to understand the unmet need for cost competitive, non-food, bio-based PTMEG. Additionally we won National Science Foundation funding to develop LGA based thermoplastics. Biobased PTMEG and thermoplastics can be produced in an integrated biorefinery from woody biomass. Coproduction enables cost savings and scalability. Accomplishments during our PhI effort have brought forward both 1) LGA based polyols as a competitor to PTMEG and 2) non-food, biobased PTMEG made cost competitive through feedstock processing synergies with thermoplastics made from LGA. We are currently comparing these two routes to replacefossil fuel basedpolyols with woody biomass based polyols. The overarching goal of our NIFA SBIR is to provide industrial polyols from woody biomass.
Publications
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