Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Abstract

The upgrading of biomass‐derived compounds has arisen in recent years as a very promising research field in both academia and industry. In this sense, a lot of new processes and products have been developed, often involving levulinic acid as a starting material or intermediate. In the last few years, though, other scaffolds have been receiving growing attention, especially, angelica lactones. Considering these facts and the emergent applications of said molecules, in this review we will discuss their preparation and applications; the use of these frameworks as starting materials in organic synthesis to produce potential bioactive compounds will be covered, as will their use as a foundation to highly regarded compounds such as liquid alkanes with prospective use as fuels and polymers.

A Facile Direct Route to N‐(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen

“…The formation of GVL ( Figures 1B and S3), which can be obtained from ALs by hydrogenation with HCOOH, [19] suggests that ALs could be the intermediates leading to the N-heterocycles MDPY and MPD. To explore this possibility, a-AL was thermally treated with H 2 NCHO in water or neat conditions, where-by 44 %a nd < 6% MPD yields together with MDPY in roughly 8% and < 1% yields,r espectively,w ere obtained after heating at 160 8Cf or 1h.T hese differences can be attributedt ot he reversibility of the reaction between LA and ALs, [16] with the presence of water shiftingt he equilibrium to the LA side.…”

Highly Efficient Synthesis of Alkyl Levulinates from α-Angelica Lactone, Catalyzed with Lewis Acidic Trifloaluminate Ionic Liquids Supported on Carbon Nanotubes

“…The proposed mechanism for the conversion of -AL to LAEs. 11 In this work, for the first time, the highly selective and stable catalyst for the -AL-to-LAEs route based on Lewis acidic triflometallate ionic liquids is presented. The catalyst was used under homogenous conditions as well as heterogeneous, as an active phase in the form of film supported on the solid carrier.…”

Lewis‐Pair‐Mediated Selective Dimerization and Polymerization of Lignocellulose‐Based β‐Angelica Lactone into Biofuel and Acrylic Bioplastic

“…[2,3] Considering that polymeric materials and transportation fuels currently account for approximately 50 %o ft otal fossil feedstock consumed annually, [4] the development of catalysis that can effectively convert biomass-based platform chemicals into bio-based polymers [5] or precursors for biofuels [6] has been extensively studied (i.e.bio-refinery). However,the selective production of abio-based polymer and aprecursor for biofuel from one feedstock by one versatile and robust catalytic system, which would be highly desirable,h as remained an unmet challenge.Angelica lactones (ALs), [7] including a-, b-, and gisomeric forms (Scheme 1A), have attracted growing attention recently as they are the key downstream chemicals of levulinic acid, which is available in atotal yield of more than 80 %f rom lignocellulose,a nd was classified recently by the US Department of Energy as one of top 10 biomass-derived compounds best suited to replace petroleum-derived chemicals. [5c, 8] Moreover,v arious value-added chemicals [9] and precursors for biofuels [10] can be produced from ALs,t hus establishing ALs as potential platform chemicals.Asanotable…”

“…Angelica lactones (ALs), [7] including a-, b-, and gisomeric forms (Scheme 1A), have attracted growing attention recently as they are the key downstream chemicals of levulinic acid, which is available in atotal yield of more than 80 %f rom lignocellulose,a nd was classified recently by the US Department of Energy as one of top 10 biomass-derived compounds best suited to replace petroleum-derived chemicals. [5c, 8] Moreover,v arious value-added chemicals [9] and precursors for biofuels [10] can be produced from ALs,t hus establishing ALs as potential platform chemicals.Asanotable…”