Update in metathesis technology commercialisation

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Last month, the death of Professor Robert Grubbs, a 2005 Nobel Prize winner in Chemistry and instrumental in the development of metathesis catalysts, took me back all the way in 2008 during the formation of Elevance Renewable Sciences, one of the few start-up companies I’ve interviewed and started covering when I started the blog in 2007.

Metathesis opened up opportunities to produce many new molecules including those that were developed by Elevance using plant oils. The company was officially launched as a joint venture of agribusiness firm Cargill and technology company Materia which was founded by Professor Grubbs to commercialise metathesis-based materials for practical, commercial applications, initially in sporting goods.

Using Materia’s catalysts, Elevance entered a joint venture with Singapore-based agribusiness firm Wilmar in 2010 to manufacture high-performance specialty chemicals with a 180 ktpa biorefinery in Gresik, Indonesia. So what happened with Elevance since then? Throughout the years that I’ve covered the company, it has launched several products and collaborated with companies such as Chemtura (now owned by Lanxess), Biesterfeld Spezialchemie, Arkema, Stepan, Clariant, P&G, Stahl, Versalis, Azelis, etc.

In 2016, the company decided to abandon its plans to expand production in the USA after selling its Natchez, Mississippi, facility to World Energy for an undisclosed sum. Elevance purchased the Natchez biodiesel facility in 2011 with the purpose of retrofitting the facility for its second metathesis-based biorefinery with a 280 ktpa capacity for an investment value of $225 million. To get additional revenues from the facility, World Energy has been producing BQ9000 certified biodiesel from the Natchez plant under contract with Elevance since 2013. Elevance has already made upwards of $30 million investment improving the Natchez site, as well as successfully producing glycerine. In December 2015, Elevance gave World Energy the option to purchase the facility. The site currently has the capacity to produce 72m gal/year of biodiesel and 7.2m lbs.year of crude glycerine. World Energy is still producing glycerine with up to 95% purity, and fatty acids with up to 50% purity at the site.

Back to Elevance, the company became very quiet since late 2019. In early 2020, the company was reportedly undergoing massive restructuring and sold its 25% stake in Genting Integrated Biorefinery (GIB) Sdn Bhd for $17.3m in cash to Malaysia-based Genting Plantations Bhd.  Elevance ceased being a shareholder of GIB but has remained a licensor for the metathesis technology that GIB planned to use in its existing 200 ktpa biodiesel plant in Lahad Datu, which was expected to be converted into a metathesis-based biorefinery. Genting Plantations now fully owns GIB and has the flexibility to pursue building a metathesis plant in the future using palm oil feedstock. So far, there is no update on whether Genting Plantations will proceed with building the metathesis-based biorefinery in Lahad Datu. It is believed that the company is looking for stakeholders and government incentives to finance the project.

In June 2020, Elevance sold its 50% stake in the Gresik biorefinery making Wilmar the sole owner of the 180 ktpa metathesis plant. All production, operation and sales coming from the Gresik biorefinery are now managed by Wilmar through its subsidiary PT Aria Persada Indonesia, while Elevance probably just deals with patent licensing and maybe a little bit of R&D. There had been no news or company presentations that the blog heard from Elevance since the pandemic started.

In the meantime in Europe, another metathesis-based biorefinery is being planned. I wrote a special report for Tecnon OrbiChem’s Biomaterials section in December last year about VERBIO AG and its plans to enter the ethenolysis market. The ethenolysis process reportedly affords a simpler product slate with two core products as compared to the butane system that produces four that include multifunctional esters, bio-based alpha and internal olefins, and a premium mixture of oleochemicals.

VERBIO AG announced in September 2021 an ethenolysis project near Leipzig, Germany that will produce several short-chain olefins and esters using rapeseed methyl ester feedstock. I wrote all the nitty-gritty details of the project but one important thing to point out here is that VERBIO also owns XiMo, which will provide the metathesis catalyst for the project. XiMo was founded in 2010 for the research, development, industrial use, production and commercialisation of Schrock-type Mo/W-based olefin metathesis catalysts and was acquired by VERBIO in 2018.

Elevance and XiMo had some collaboration history together. In 2011, Elevance and XiMo started working on a molybdenum/tungsten-catalysed metathesis of natural oil esters and olefins, particularly ethylene. The Gresik biorefinery is based on ruthenium metathesis catalysts licensed from Materia using natural oils and butene feedstock.  One of the reported. advantages for using a molybdenum catalyst is that it can produce more C10+ linear alpha olefins (LAO) distributions and less linear internal olefins (LIO) in the mix. Another advantage for using the molybdenum catalyst is the ability to use ethylene instead of butene. Intermediate olefins are generally used in the production of detergent alcohols as well as polyalphaolefins (PAOs) used in Group IV synthetic lubricants and oilfield chemicals.

In 2016, XiMo and Elevance were both collaborating with Italy-based Versalis for the possibility of a metathesis-based production at Versalis’ Porto Marghera facility using 1-butene. The blog is not sure whether this planned project will be resurrected in the near future.

XiMo, by the way, is currently building a commercial metathesis catalyst plant in Budapest, Hungary, simultaneously with the construction of the ethenolysis plant in Germany.   According to Verbio AG, the aggregate investment costs of both facilities are in the range of EUR300 million which are expected to be completed by the end of 2023.

So what happened to the other metathesis catalyst developer, Materia?

In 2018, Belgium-based Umicore acquired Materia’s exclusive metathesis catalyst intellectual property portfolio and since then has been selling these catalysts to customers (including Wilmar’s Gresik facility). Materia has since then focused solely on its Proxima® resins business which leverages the Grubbs Catalyst® technology to produce high-performance thermoset resins.

In December last year, ExxonMobil acquired Materia and its extensive portfolio of patents and intellectual property, its headquarters, research and technology centre in Pasadena, California and its manufacturing facility in Huntsville, Texas. ExxonMobil intends to operate the business under the Materia company name as a wholly-owned subsidiary.

ExxonMobil and Materia have been collaborating since 2017 to research further uses for Proxima® resins under a joint development agreement, including wind blade and anti-corrosion coatings. The technology could enable the manufacture of longer and more durable wind turbine blades for more efficient renewable energy generation. ExxonMobil anticipates expanding the scope of applications for Proxima®, including parts for electric vehicles and sustainable construction projects.

For those who like to learn more about metathesis technology (technically anyway), here’s an interesting video that could be helpful. Lastly, the blog is sending its condolences to the family, friends and colleagues of Professor Grubbs.

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