Levulinic acid (LA) can be produced cost effectively and in high yield from renewable feedstocks in a new industrial process. The technology is being demonstrated on a 1 ton/day scale at a facility in South Glens Falls, New York. Low cost LA can be used as a platform chemical for the production of a wide range of value-added products. This research has demonstrated that LA can be converted to methyltetrahydrofuran (MTHF), a solvent and fuel extender. MTHF is produced in >80% molar yield via a single stage catalytic hydrogenation process. A new preparation of δ-aminolevulinic acid (DALA), a broad spectrum herbicide, from LA has also been developed. Each step in this new process proceeds in high (>80%) yield and affords DALA (as the hydrochloride salt) in >90% purity, giving a process that could be commercially viable. LA is also being investigated as a starting material for the production of diphenolic acid (DPA), a direct replacement for bisphenol A.

Production of levulinic acid and use as a platform chemical for derived products

The limitation of fossil resources and the global efforts to reduce anthropogenic carbon dioxide emissions demand innovative strategies for the sustainable production of fuels and chemicals from renewable raw materials. Carbohydrates derived from lignocellulosic biomass comprise the largest fraction of terrestrial biomass feedstocks. Their conversion into valuable products can be envisaged by subsequent selective transformations of a set of platform molecules (new building blocks) that constitute the key intermediates for molecular diversity. The industrial implementation of such advanced biorefinery concepts faces a number of ecological, economic, and logistical challenges. On the most fundamental level, it is essential to develop novel synthetic methods and catalytic processes for the selective deand refunctionalization of biogenic substrates to yield a broad range of versatile chemical structures. Ultimately, this could allow the design of the optimum reaction pathway starting from the desired product structure, in analogy to a retrosynthetic analysis in traditional organic synthesis. Whereas much effort currently focuses on production processes for platform molecules, their true potential for further conversion remains largely unexplored. Scheme 1 exemplifies how a diverse range of highly attractive products and building blocks could be derived from levulinic acid (LA), which is accessible from wood-based feedstocks, and itaconic acid (IA), which can be obtained from green biomass. In particular, the cyclic ester g-valerolactone (GVL) has been proposed as one of the key components in a biomass-derived economy. Biogenic diols are interesting building blocks for biodegradable polyesters and other polymeric materials, as demonstrated by the commercialization of Sorona, a polyester which is made from glycerolderived 1,3-propanediol. Among the cyclic ethers, 2-methyltetrahydrofuran (2-MTHF) is advocated as an alternative solvent in the pharmaceutical industry and is also considered a fuel component. 3, 9] Hydrogenation routes involving heterogeneous catalysts to produce GVL, 2-MTHF, or 3-MTHF have been proposed. Organometallic catalysts based on ruthenium phosphine systems were reported to allow the conversion of succinic acid into g-butyrolactone and LA into GVL. 14] In Scheme 1. Analysis of reaction pathways for a variety of chemical structures formed from levulinic acid (LA) and itaconic acid (IA) as platform chemicals in a cellulose-based supply chain.

Selective and flexible transformation of biomass-derived platform chemicals by a multifunctional catalytic system

A Cu-catalyst derived from hydrotalcite precursor was highly selective for the hydrogenation of biomass-derived furfural and levulinic acid. 90% yield of furfuryl alcohol and 51% yield of 2-methylfuran were achieved selectively in the hydrogenation of furfural. 91% yield of γ-valerolactone was achieved in the hydrogenation of levulinic acid.

http://www.chtf.stuba.sk/~szolcsanyi/education/files/Chemia%20heterocyklickych%20zlucenin/Prednaska%207/Doplnkove%20studijne%20materialy/Hydroxymethylfurfural/Reduction%20of%20biomass-derived%20furfural%20and%20levulinic%20acid3.pdf

A noble-metal free Cu-catalyst derived from hydrotalcite for highly efficient hydrogenation of biomass-derived furfural and levulinic acid

https://hal.archives-ouvertes.fr/hal-01169277/document

T.W. Rudolph

Papers

NOx, NMHC and CO emissions from biomass derived gasoline extenders