Mathieu Flamini – Levulinic Acid King
by Andrew Crawshaw
There have been a number of reports recently in the Press that our Mathieu is doing extremely well for himself outside the world of football.
In 2008 he founded a company, GF Biochemicals, in Italy with a friend Pasquale Granata. This has been kept very quiet until this week when they have gone public and announced that they are producing Levulinic Acid on an industrial scale. Indeed they claim this to be a world first and a potential “game changer” in a $20bn a year industry. Here is a link to the company website for those of you who want to look in far more detail.
Levulinic Acid (C5H8O3) in itself isn’t new, it has been produced since 1870 and has significant potential as an industrial chemical and as a partial replacement for oil. Some uses are as resins and coatings, solvents, pharmaceutical, personal care, detergents, fuel additives, plasticizer, textile, animal feed and antifreeze.
It is said to have a number of significant advantages over existing chemicals being non-toxic and far more bio-degradable. What is new is the claim from GF Biochemicals that in July this year they started to produce it on an industrial scale directly from biomass (essentially most sorts of plants including waste from other processes – currently they list grass, wheat straw, wood and cellulose).
Levulinic Acid is recognised by the US Department of Energy as one of the top bio-based platform chemicals of the future. It is a versatile building block for other chemicals and other materials derived directly from biomass.
The company is based in Caserta in Italy and currently has about 80 employees with a further 320 or do dependent jobs, so that in itself isn’t insignificant. They have a very large research and development team who along with commercial staff are based in the Netherlands, and have worked closely with the University of Pisa (one of Italy’s best universities) and the Polytechnic University of Milan.
Their projections are for production to be 4,500 Tonnes in 2016 rising to 10,000 in 2017 and 50,000T in 2019 as they expand production worldwide. Clearly an important product looking into the future. By 2020 the company projections are for an annual market of somewhere in the region of 1,500,000 Tonnes so clearly vast scope for expansion beyond current aims.
Matthieu says that he has invested a lot of money in the company. Whilst nothing in life is certain, except for death and taxes [and transfer rumours – Tony], I would guess that whatever his investment is it is likely to repay him back on a ratio of somewhere between 100 and 1,000 to one (always assuming that the process works as it is claimed to). Nice one Son!
More anniversaries
- 17 November 1993: Ian Wright scored four goals for England in a World Cup match v San Marino.
- 17 November 2004: George Curtis died. He went to Southampton in 1947 and gained the nickname “Twinkletoes”, and then moved to Valenciennes in France in August 1952. He later followed up his wartime Indian connections by coaching the Indian Olympic squad of 1948 before moving to be Chelmsford City’s player-coach, later coaching Sunderland, Brighton, Cambridge University, Hastings, Stevenage Town, Hull City, San Diego Toros, and Rosenborg in Norway, the Norwegian national team and finally in Qatar.
The Untold Books
- Woolwich Arsenal: The club that changed football – Arsenal’s early years
- Making the Arsenal – how the modern Arsenal was born in 1910
- The Crowd at Woolwich Arsenal
Clever move from Mathieu. At the moment the oilers came knocking on the door of football he started a new company that would make us less dependable on the oil from the oilers and thus make the oilers less rich. 😉
Mathieu for president!!!
A potentially risky investment that seems to have worked out very well indeed. He could easily have lost his money but now seems to have backed a big-time winner. Most importantly he has a company actually making something and now providing incomes for 400 or so people. A great example for other young footballers who usually have more money than sense.
Being biodegradable is both good and bad. It is bad, in that outside applications typically need to protect the material from the environment.
Being an acid, it is not surprising to see it contains a COOH group at one end. The carbon has a double bond to one oxygen, and the remaining bond for the carbon is to a hydroxyl group (and the hydrogen itself can free itself, leaving behind a charged COO- group. The “extra” electron becomes delocalised by the central carbon and terminal oxygens, making the structure more stable.
If 2 COOH groups are in proximity, a person can remove a single molecule of water (H2O), with the bonding now having an oxygen connecting the two carbon backbones. I believe this is called an ether linkage, and the reaction is called a condensation reaction. Many polymers react via this kind of reaction, and typically bonding is done under pressure to minimize the formation of steam bubbles in the polymer from the released water molecules.
As an energy source, the C5H8 part needs 7 oxygen molecules (14 oxygen atoms) to be fully consumed. The molecule already has 3 oxygen atoms, hence another 11 are required for full oxidation.
To the best of my knowledge, the generic formula for cellulose is some huge chain of 6 carbon sugars (hexoses, C6H12O6). Levulinic acid is a 5 carbon compound, how do you make it from cellulose? Well, the answer is you coproduce a 1 carbon compound. In this situation, that one carbon compound is the simplest of the carboxylic acids: formic acid (HCOOH). The formic acid is of general usefulness, and there are other processes making it today.
Levulinic acid is not yet of global importance, but it was mentioned by the US DOE about 10 years ago as a possible platform molecule of interest. From what I have read, the only manufacturers today number two, both in Italy. Other universities and researchers are working on it. If at some point, manufacturers get big enough, companies like BASF will come knocking and try to buy the company.
Top Value Added Chemicals from Biomass
http://www.nrel.gov/docs/fy04osti/35523.pdf
2004
On the page labelled 45 in that document, is a map of possible derivatives of levulinic acid. There are 3 derivatives which contain the oxirane (epoxide) group that I know a little bit, and that is just a single oxirane. Most of the epoxies I have looked at are polyfunctional, with 2, 3 or 4 oxirane groups per molecule. There are a couple of acrylic derivates, and another which apparently could be used as a replacement for bisphenol A in polycarbonate (lexan) production. I don’t know enough organic chemistry to tell you why this compound couldn’t be (easily) used as a replacement for Bis-A in other processes (such as making epoxies, ordinary epoxy is the DiGlycidal Ether of Bisphenol A).
And I would guess all this chemistry is even worse than the math I occasionally expectorate.
But congratulations to Flamini for getting into this.
Gord – I’m impressed! Way beyond my A level chemistry…
As for Mathieu – still early days and plenty can yet go wrong. According to the original article, I think, they have registered a lot of patents. Let’s hope they stick.
Off Topic, I see we have Clattenburg at the weekend. First time for quite a while. Unfortunately, it implies he will be less likely to have our Man City game. We really, really need to avoid Atkinson, Dean and Taylor for that one. Maybe Michael Oliver?
Here are all the appointments
Saturday 21 November 2015
K.O. _MATCHES _ _ _ _ REFEREE _ _ _ _ ASST. REF. 1 _ _ASST. REF. 2 _ _4TH OFFICIAL
15:00 Chelsea _Norwich _ _ Craig Pawson _ _ S Child _ _ R West _ _ R East
15:00 Everton _Aston Villa Michael Oliver _ S Burt _ _ _G Beswick _N Swarbrick
17:30 Man City _Liverpool _Jonathan Moss _ _S Bennett _ E Smart _ _K Friend
15:00 Newcastle _Leicester Mike Jones _ _ _ D Cann _ _ _A Nunn _ _ M Atkinson
15:00 Southampton _Stoke _ Lee Mason _ _ _ _S Ledger _ _A Halliday S Martin
15:00 Swansea _Bournemouth Andre Marriner _ M Mullarkey J Brooks _ P Bankes
12:45 Watford _Man Utd _ _ Robert Madley _ _M McDonough M Perry _ _A Taylor
15:00 West Brom _Arsenal _ Mark Clattenburg S Beck _ _ _J Collin _ S Attwell
Sunday 22 November 2015
K.O. _MATCHES _ _ _ _ REFEREE _ _ _ _ ASST. REF. 1 _ _ASST. REF. 2 _ _4TH OFFICIAL
16:00 Spurs _West Ham _ _ _Anthony Taylor _ S Long _ _ _A Garratt _R East
Pete
While I know a little organic chemistry, it is really not enough.
Ideally, levulinic acid would become a commodity chemical. I don’t like patents in general, I think they become even more of a nuisance for commodity products. All patents are currently guaranteed to do, is to make some lawyers rich.
I think it much better to give the knowledge to society (public domain) and just become famous.
Gord – Part of me agrees with you. But I can’t see Flamini and his mate, as an example, investing millions in the development of their new process if they didn’t have protection…
As for the refs, see that Dean isn’t officiating. Moss has got the other big game – seems to be going places.. notwithstanding the allegations against him!
The big chemical companies (like BASF) could start making levulinic acid by the processes developed by GF Biochemicals, and there is little Flamini could do about it. They cannot afford to sue them. Public opinion might have some influence. But in general, any protection Flamini has is ephemeral.
The New York (USA) Post had a longer article on Flamini and GF Biochemicals.
In terms of fuel, I don’t know what direction they would head using levulinic acid as a starting point. I did mention that the compound is partly oxygenated (21%). There are gasoline additives which are oxygenated. But one reason why ethanol is probably not going to replace gasoline is because it is partially oxygenated.
A while ago, Canada’s military was looking into stealth snowmobiles. I volunteered a 50 or so page report on this from a materials point of view (I got a thank you from DND). But, I was looking at using DiMethyl Ether (CH3-O-CH3) as the fuel in a Diesel cycle engine. DME will work in a Diesel cycle, the biggest problem is that it has little or no lubricity. But, that ether linkage separating the two methyl groups makes it almost impossible for the engine to produce soot. Volvo has been looking into this as a fuel I believe. It is vagely like propane, in that it boils at one atmosphere at a little below 0C. It takes little pressure to have it as a liquid fuel at room temperature. It also doesn’t have the flow problems of diesel fuel at low temperatures.
I wish Flamini all the best with this.
Here’s wishing good luck to Mathieu.
I only wish he had done this in 2008 so that he didn’t have to move to AC Milan for the money when we needed him the most!