TECHNOLOGY LICENSING OPPORTUNITY: GreenFuran Direct Allylation

A mild, biomass-friendly route to allylated furans

Manufacturers who depend on alkyl and allylic furans can now reach these valuable ingredients through a single, low-waste step that trades cryogenic equipment, hazardous reagents and costly precious metals for gentle heating and cheap, recyclable catalysts. The GreenFuran Direct Allylation method developed by Los Alamos National Laboratory feeds on renewable, biomass-derived alcohols, produces only water as a byproduct and lifts away the catalyst by simple filtration, so operators gain a cleaner process, an easier cleanup and lower input costs at the same time. Crucially, the reaction succeeds on substituted and even multiply substituted furans that older approaches simply could not convert, opening a wider palette of products from one dependable platform.

The Challenge

The established ways to make alkyl furans — chiefly ortho-lithiation, Friedel-Crafts alkylation or transition-metal-catalyzed C-H functionalization — each carry serious burdens when moved beyond the bench. Ortho-lithiation demands cryogenic temperatures and pyrophoric organolithium reagents that ignite on contact with air, while Friedel-Crafts routes consume stoichiometric quantities of Lewis acids that generate large volumes of waste and complicate cleanup and metal-catalyzed methods rely on expensive metals and ligands and inaccessible starting materials.

Problems Solved

GreenFuran Direct Allylation answers each of those burdens with a single dehydrative reaction that couples furans and allylic alcohols directly, eliminating the separate prefunctionalization step and its associated waste while yielding only water as the byproduct. The process runs under mild conditions, needing just ambient conditions or gentle heating up to 60 degrees Celsius, and it uses simple, inexpensive and environmentally benign catalysts including aluminosilicates and metal phosphates. The solid catalyst separates cleanly by filtration or decanting, removing the difficult workup common to older routes, and the allylic alcohols themselves can be drawn from renewable feedstocks. Most importantly, the method extends reliably to substituted and polysubstituted furans bearing alkyl, aryl and fused-aryl groups as well as esters, aldehydes and ketones, reaching the very targets earlier methods could not.

Advantages

•          Mild, safer operation that avoids cryogenic cooling and hazardous, air-sensitive reagents

•          Inexpensive, environmentally friendly catalysts that can be removed and recovered by simple filtration

•          Renewable, biomass-derived starting materials such as prenol, geraniol and phytol

•          Only water is produced as a byproduct, cutting waste and easing cleanup

•          One fewer synthetic step, because no separate preparation of the alcohol is needed

•          Broad reach across simple and complex furans that older methods could not convert

Market Applications

•          Food and Beverage (flavoring agents and additives)

•          Personal Care and Cosmetics (fragrance and cosmetic ingredients)

•          Chemicals (surfactants for industrial and consumer formulations)

•          Agriculture and Pest Control (insecticide ingredients)

 

TRL 3

U.S. Patent pending

LA-UR-26-27238

LANL Tech Partnerships: Unlock the Innovative Potential

Los Alamos National Laboratory offers a wide range of cutting-edge technologies and capabilities that may provide your company with a competitive edge in the market and unlock the innovative potential that can enhance, refine, and revolutionize your products.

LANL’s licensing program focuses on moving inventions developed by our researchers to commercial innovations. Patented and patent pending inventions and copyrighted software are available to existing and start-up companies through exclusive and non-exclusive licensing agreements. For specific discussions, please contact licensing@lanl.gov.

Note: This is not a call for external services for the development of this technology.

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