DuPont Industrial Biosciences, ADM find “breakthrough process” for a “long-sought molecule”

January 19, 2016 |

DuPontADM-smIn Delaware, DuPont Industrial Biosciences and Archer Daniels Midland announced a new breakthrough process in producing FDME from fructose, with “the potential to expand the materials landscape in the 21st century with exciting and truly novel, high-performance renewable materials”, the companies said in a joint release.

You’ll love it. You’ll need it. You’ll want it. You’ve never heard of it. You have no idea what molecule we are talking about.

FDME? Sounds more like the Federal Division of Mortgage Enforcement? That’s OK.

In our 30 Hottest Molecules industry poll earlier this year, down the list but picking up material support, readers recognized furan dicarboxylic acid (FDCA), one of the 12 building blocks identified by the U.S. Department of Energy that can be converted into a number of high-value, bio-based chemicals or materials that can deliver high performance in a number of applications.

One of its derivatives? That’s FDME, or furan dicarboxylic methyl ester.

Things you can make from FDME

The technology has applications in packaging, textiles, engineering plastics and many other industries.

One of the first polymers under development utilizing FDME is polytrimethylene furandicarboxylate (PTF), a novel polyester also made from DuPont’s proprietary Bio-PDO™ (1,3-propanediol). PTF is a 100-percent renewable and recyclable polymer that, when used to make bottles and other beverage packages, substantially improves gas-barrier properties compared to other polyesters. This makes PTF a great choice for customers in the beverage packaging industry looking to improve the shelf life of their products.

Shelf Life. Beverage Industry. Like out of the lyrics of “Love and Marriage,” you can’t have one without the other.

You can read about some of DuPont’s intellectual property in making PTF from FDME, here.

Other applications

They go on and on and on. As ADM observed in a recent patent app:

“FDCA has been discussed as a biobased, renewable substitute for terephthalic acid, in the production of such multi-megaton polyester polymers as ethylene terephthalate or butylene terephthalate. FDCA esters have also recently been evaluated for replacing phthalate plasticizers for PVC.”

Think polyamides, too. Specifically. Poly(meta phenylene 2,5-furancarboxylamide), which has DuPont reporting pathways to, from FDCA. That’s here.

Why a big deal?

A route to polymers that can not only compete with the massively produced and used PET (i.e “the clear plastic bottle stuff”), but can even exceed it on a performance basis?

As was said in Vince Vaughn’s and Jon Favrea’s breathrough movie Swingers: That’s so money.

Or, as DuPont phrased it a few years back, with a few more five-dollar words:

“Gas barrier properties are one of the key requirements for polymers used in packaging applications to protect the contents and provide desired shelf-life. The prevention of oxygen permeation, for example inhibits oxidation and microbial growth, whereas prevention of water vapor permeation retains liquid content.

Many polymers have emerged for these applications such as poly(ethylene terephthalate) (PET), polyethylene (PE), polyvinyl alcohol) (PvOH), ethylene vinyl alcohol polymer (EvOH), poly(acrylonitrile) (PAN), poly(ethylene naphthalene) (PEN), polyamide derived from adipic acid and m- xylenediamine (MXD6) and poly(vinylidene chloride) (PVdC), and may include additives to enhance barrier properties.

However, most of these polymers suffer from various drawbacks. For example, high density polyethylene (HDPE) and low density polyethylene (LDPE) has fair water vapor barrier, but poor oxygen barrier. EvOH exhibits good oxygen barrier at low humidity levels but fails at high levels of humidity. PET has relatively high tensile strength but is limited by low gas barrier properties.”

Hence, there is a need for a new polymer with improved oxygen, carbon dioxide, and moisture barrier properties.  That’s what PTF is all about. And producing it renewably with a more affordable route than PDO? Big deal.

How are they getting it done?

Both companies are keeping quiet about the exact process.

Interestingly, ADM filed a patent app in 2014:

Agricultural raw materials such as starch, cellulose, sucrose or inulin are inexpensive starting materials for the manufacture of hexoses, such as glucose and fructose. Dehydrating these hexoses produces 2-hydroxymethyl-5-furfuraldehyde, also known as hydroxymethylfurfural (HMF), among other products such as levulinic acid and formic acid. HMF and its related 2,5-disubstituted furanic derivatives have been viewed as having great potential for use in the field of intermediate chemicals from regrowing resources.

More particularly, due to its various functionalities, it has been proposed that HMF could be utilized to produce a wide range of products such as polymers, solvents, surfactants, pharmaceuticals, and plant protection agents, and HMF has been reported to have antibacterial and anticorrosive properties. HMF is also a key component, as either a starting material or intermediate, in the synthesis of a wide variety of compounds, such as furfuryl dialcohols, dialdehydes, esters, ethers, halides and carboxylic acids.

A notable example of a compound that can be prepared from HMF is 2,5-furandicarboxylic acid, or FDCA, which can be prepared from HMF, ether or ester derivatives of HMF through an oxidation process, see, for example, U.S. Pat. No. 7,317,116 and US 2009/0156841 to Sanborn et al. 

Here’s what the stakeholders say

First, “The new FDME technology is a more efficient and simple process than traditional conversion approaches and results in higher yields, lower energy usage and lower capital expenditures.” Though we’re not exactly what that is. But let that pass.

ADM adds this. “This molecule is a game-changing platform technology. It will enable cost-efficient production of a variety of 100 percent renewable, high-performance chemicals and polymers with applications across a broad range of industries,” said Simon Herriot, global business director for biomaterials at DuPont. “ADM is an agribusiness powerhouse with strong technology development capabilities. They are the ideal partner with which to develop this new, renewable supply chain for FDME.”

“We are excited about the potential FDME has to help our customers reach new markets and develop better-performing products, all made from sustainable, bio-based starting materials,” said Kevin Moore, president, renewable chemicals at ADM. “With their strong leadership in the biomaterials industry, DuPont is a great partner that can help us bring this product to market for our customers.”

The scale-up

Yep, we’re still at pilot on this one. But not for long. ADM and DuPont say they 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 planning to build an integrated 60 ton-per-year demonstration plant in Decatur, Ill., which will provide potential customers with sufficient product quantities for testing and research.

And, it’s a route to the 100% renewable clear plastic bottle, which we feature it seems around once a day at The Digest. Most recently, um, yesterday, with news that Suntory is the mystery partner backing Anellotech’s new paths to renewable paraxylene from waste biomass.

Mysteries yet to be resolved

There’s FDME and there’s FDME. Which is to say, there are a bunch of isomers in there. Such as 2,4 FDME and 2,5 FDME among other isomers — we may have to wait on more detail as to what exactly is being produced here. It’s been secret enough that’s there’s virtually no record in the patent catalogue. Most of what we’ve seen in this area has been IP developed by Braskem.

The Bottom Line

A breakthrough as a claim, for sure. ADM’s and DuPont’s track record in scaling up molecules is strong. And, it’s an interesting pair of partners. And could ADM use a big new chemical for fructose, with limitations foreseen on the growth opportunities for high-fructose corn syrup? That’s more than a “yes” or even a “you bet”, that’s a “God bless us all, every one”.

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