FDME and PTF – Emerging stars on the bioplastics horizon

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Since Archer Daniels Midland Company (ADM) and DuPont Industrial Biosciences (DuPont) unveiled its breakthrough process to produce 2,5-furan dicarboxylic acid dimethyl ester (FDME, Furan Dicarboxylic Methyl Ester) on January 19th 2016 (see press release), I have been looking for an opportunity to prepare a post on this molecule and its impact on the bioplastics field. Last week, the Bioplastics Division of the Plastics Industry Association (PLASTICS) announced ADM and DuPont as the winners of the 2017 Innovation in Bioplastics Award recognizing the contribution of this new process to expand the bioplastics landscape (see announcement). Thus, I think that it is the right time to know more about this new biobased platform.

FDME: background and new process

Advances on furanics are gaining momentum. The production of 5-hydroxymethylfurfural (5-HMF) and 2,5-furandicarboxylic acid (FDCA) at commercial scale is still about to take off (see post on FDCA biorefineries) and a new molecule already emerges in the horizon. The problems related to the production and the manipulation of FDCA (for instance, its poor solubility in common organic solvents or its tendency to decompose at temperatures greater than about 180°C to furoic acid) have caused some chemical companies seek alternatives. Its transformation into FDME can be a solution. Current acid catalyzed esterification takes too long so it is not cost effective for high-volume production of the esters. Other alternatives for esterification of FDCA require its activation as a diacyl chloride, which makes the process not sustainable or economical.

According to the information released by ADM and DuPont, the new FDME-producing technology is more sustainable and results in higher yields and lower energy and capital expenditures than those traditional conversion methods. However, they do not explain the details of the new route. If we look up in a recent patent of ADM, an interesting clue can be found: the company proposes the reaction of FDCA with alcohols in a CO2 atmosphere in the substantial absence of any other acid catalyst to obtain furan dicarboxylates (WO 2014099438 A2, publication date: 26/06/2014).

FDME is a biobased chemical building block with the potential to replace petroleum-based materials in a number of sectors including packaging, adhesives, coatings, elastomers and plastics.

Figure 1. FDME molecular model

PTF: a promising biopolymer

One of the first polymers under development utilizing FDME is polytrimethylene furandicarboxylate (PTF):
Monomers
FDME and 1,3-propanediol (PDO)
Characteristics
- 100% renewable (when also using renewable PDO)1.
- Recyclable.
- Excellent gas barrier properties.
Applications
Bottles and other beverage packages.
Note 1: DuPont already produces proprietary bio-PDO.

Current status of the technology

ADM and DuPont are taking the initial step in the process of bringing FDME to market by moving forward on the scale-up phase of the project. The two companies are building an integrated 60 ton/y demonstration plant in Decatur (Illinois, USA) that will be online later this year.

The facility will provide potential customers with sufficient product quantities for testing and research as well as the required basic data for a planned commercial-scale plant.

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