Innovations

TECHNOLOGY COMMERCIALIZATION

Biomass-Derived Isoprene in High Yield

A new process uses a novel catalyst to synthesize isoprene in high yields. Isoprene is made by contacting 3-methyltetrahydrofuran (MTHF) with a heterogeneous acid catalyst (other than alumina, or Al2O3). This catalytic process dehydrates MTHF to isoprene via several combinations of temperatures, pressures, and space velocities (reactant volumetric flow rate per volume of catalyst) and achieves conversion rates of MTHF to isoprene of up to 100%.

Inventors: Paul Dauenhauer, Kechun Zhang

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Environmentally Friendly Thermoset from Sugar

A process has been developed for synthesizing two new dimethacrylate monomers from glucose and mannose. The materials produced by the sugar-derived dilactones undergo degradation in basic conditions while remaining stable in neutral and acidic environments. The dimethacrylates are derived from sugars, making them renewable and comparable to petroleum-based sources. The monomers reported are sugar-derived dimethacrylates, and provide a pathway to create sustainable materials for use in coatings, thermosets, adhesives and particle-based drug delivery.

Inventors: Marc HillmyerTheresa Reineke

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Isosorbide Based Block Polymers

An isosorbide-based methacrylate monomer has been synthesized and polymerized to produce block polymers. This new isosorbide derivative, acetylated methacrylic isosorbide (AMI), is easily synthesized from commercially available starting materials in just two steps. The AMI monomer can further be polymerized to form block copolymers.

Inventors: Marc HillmyerTheresa Reineke

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Biobased Polymer Synthesis from Sugar

A method of creating a scalable block copolymer from a new branched lactone monomer has been developed. The new lactone monomer is generated from direct fermentation of sugar.  The biobased monomer, when copolymerized with lactide, has many utilities and its mechanical properties (e.g. stretchiness, strength) can be tuned depending on the application requirements. Sugar (glucose) is one of nature’s simplest and most common organic compounds, and the resultant polymers from this new process are biodegradable, affordable, and available for mass-production. Applications of these polymers are disposable materials, thermoplastics, and sustainable plastic components.

Inventors: Frank BatesMarc Hillmyer, Kechun Zhang

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Olefin Synthesis from Biomass

A catalytic process allows commodity olefins to be synthesized from the carboxylic acids of biomass. This bio-based feedstock approach is a desirable method for generating olefins that can be used to make plastics and other chemicals. The process, which involves the decarbonylation of carboxylic acids from biomass, creates olefins such as styrene, acrylates, acrylonitrile and octene in moderate to good yield. Furthermore, by adding a tandem Heck-type coupling reaction, the process can also generate stilbenes, which are desired bioactive targets.

Inventors: Marc HillmyerWilliam Tolman

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Biological Pathways Produce Isobutyric Acid Using Renewable Resources

Biological pathways that produce isobutyric acid from sugar-based feedstocks have been developed using fungal and bacterial enzymes. These biological pathways are more environmentally friendly and direct than chemical synthesis. Note: This technology for producing isobutyric acid has been exclusively licensed to Ascenix Biotechnologies.

Inventor: Kechun Zhang

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Biosynthetic Pathway to 1,4-Butanediol and other C4-C5 Chemicals

To reduce the costs of making valuable C4-C5 renewable chemicals, a biosynthetic pathway has been developed to generate C4-C5 chemicals, such as succinate, amino acids and 1,4-butanediol. This new pathway from sugars involves only five fermentation steps, as compared to the current pathway, which requires 23 steps. The new process uses engineered microbes and a simple pathway that produces less contaminating byproducts and higher yields (50% higher theoretical yield). This new approach makes the production of cost-effective renewable bioplastics, polyesters and spandex a possibility.

Inventor: Kechun Zhang

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Stereocomplexation of Poly(propylene succinate) for the Synthesis of a Biorenewable Semicrystalline Polyesters

This invention describes a new aliphatic polyester stereocomplex formed from the mixture of racemic, isotactic, regioregular chains of poly(propylene succinate). The resulting material has a characteristic melting point approaching that of low density polyethylene.

Inventors: Geoffrey Coates

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Biodegradable Polylactic Acid Plastic is Strengthened with Co-polymer

A process developed at the University of Minnesota can strengthen polylactic acid using less added material (as little as 1 wt% of non-polyactic acid material as opposed to 2-3 wt% for commercial additives) by creating a co-polymer. This added strength expands the potential polylatic acid applications to replacement of high impact polystyrene and packaging.

Inventor: Marc Hillmyer

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Toughened Polylactic Acid

Brittle thermoplastics such as polylactide/polylactic acid (PLA) can be significantly toughened with amphiphilic block copolymers.

Inventors: Frank Bates, Lorraine Francis  View Technology

Porous Cyclodextrin Polymer for Rapid Removal of Organic Contaminants in Water Purification

The invention provides alternative broad-spectrum sorbents for water
purification and other applications with superior adsorption kinetics.

Inventor: William Dichtel

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Bio-Derived Methyl Butanediol and Methyl-Substituted Polyesters

A new process synthesizes multifunctional alcohols from bio-derived carboxylic acids.

Inventors: Kechun Zhang, Paul Dauenhauer

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START-UP COMPANIES

The following companies were founded by CSP researchers based CSP research innovations.

CycloPure

“CycloPure has developed the first ever porous cycodextrin polymers with selective adsorption against unwanted compounds. We rapidly remove selective pollutants present in low concentration, sustainably and cost-effectively. CycloPure provides pioneering adsorption technologies to protect human health and the environment. ” — CycloPure

Founder: William Dichtel

CycloPure Website

Valerian Materials

“Valerian Materials will lead the way in renewable, degradable, and recyclable polymers. The biomass derived materials have applications as resilient foams and elastomers as well as tough plastics and thermosets. The principal technology relies on efficient and economical fermentation of sugar to give small molecules that can be catalytically converted to polymers in high yields at low temperatures with controlled molar mass. The versatility of the polymer platform is a key aspect and allows for broad penetration in a wide variety of industries. ” — Valerian Materials

Cofounders: Kechun ZhangFrank Bates, Marc Hillmyer

Valerian Materials Website

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