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​Email:       kondor@kemia.at

                kaldi@kemia.at
Address:   Hietzinger Hauptstraße 50
                1130 Vienna, Austria
Phone:      +43 (1) 877 0553

                © 2013 - 2018 by Kemia Handels- und Projektierungs GesmbH

TOMS = TRIGLYCERIDES OF MODIFIED STRUCTURE 

Scarcity of precious vegetable oils (triglycerides, TG’s) calls for their most efficient utilization. Also, the „food vs. fuel” debate will haunt us for a long time to come. Hence we are offering a healthy compromise with our „TOMS”, i.e. Triglycerides of Modified Structure, a patented novel biofuel and pertaining process (“TOMS1”), also affording at the same time novel renewable building blocks for the bioplastics, biolubricant, biohydraulics, etc. industries (“TOMS2”), thereby multiplying raw material sourcing with greatly expanded variability for the oleochemical industries.

 

Biofuel aspects:

 

In California (2013) an initiative was taken this spring to boost biofuel research and production as alternatives to conventional biodiesel (FAME), on account of the latter's numerous disadvantages (usage of fossil-derived methanol, generation of large volumes of sewage, loss of cca 10 - 12% of precious feedstock oils for fuel purposes in the form of glycerol, etc.), see here:

 

http://www.greencarcongress.com/2013/03/arbadf-20130324.html#more

 

This requirement has recently been reiterated:

 

http://www.greencarcongress.com/2013/10/20131016-kesan.html#more

 

Our patented TOMS stand-alone petrodiesel replacer is already here, with freshly granted patents in the EU, US, Japan, China, Russia, Indonesia, Malaysia, Australia, etc., possessing numerous merits over FAME, derived likewise from triglyceride oils, and manufactured in a glycerol-free process, yielding 1.15 - 1.20 units of fuel (that is 15 - 20% extra mass) out of one unit of feedstock oil. See our PTC/HU 2008/000013 international application.

 

Chemistry:

 

We have worked out a process for attaining a novel kind of petrodiesel replacer, that is for a 100% green renewable biofuel, produced via a "glycerol-less" methodology (thus putting an end to the “glycerol-glut”). We react oils (TG's) not with alcohols (methanol/ethanol) as conventional biodiesel manufacturers do, but with an ester (alkyl-carboxylates, e.g. methyl or ethyl acetate), that is we interesterify two esters (TG's being triesters of glycerol), but only partially, that is we exchange some of the original long chains of oils (with C16 - C24 carbon numbers, that are responsible for high viscosities of such oils) for short ones (in this present case for C2 acetyl). Thus we arrive at a two-component fuel mixture, component 1 being a modified triglyceride (mTG, or "TOMS", that is Triglycerides Of Modified Structure", a "mixed" triglyceride, containing both short and long side-chains), with reduced molecular mass and lowered viscosity accordingly (these two properties going hand in hand), and component 2 being methyl (or ethyl) esters of displaced fatty acids, that is conventional biodiesel (FAME/FAEE). This is our reaction sequence (in case we effect a 33 1/3% chain exchange):

 

                                                   

 

 

 

 

 

 

 

 

 

 

TOMS1 Merits:

 

So every atom of feedstock oils is turned into fuel, with no glycerol byproduct, as the glycerol backbone has been retained, moreover on account of incorporation of the ethyl acetate moieties into the fuel, from one unit of feedstock oil we get 15 – 20 % more fuel. 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

That is we have no wastes, our fuel having superior fuel properties over conventional biodiesel (FAME), e.g. our solidification point with palmoil feedstock being 3°C (as against 15°C for palm oil based FAME), our iodine number  being always necessarily lower than that of the corresponding FAME, on account of „dilution of double bonds” with the incorporation of ethyl acetate moieties, our oxidation stability being 11.6 hours (as against < 6 hours with FAME), our specific gravity being 0.915 (FAME: 0.88), making our volumetric energy density practically the same as that of petrodiesel (specific gravity here being 0.83), etc. And on account of retention of the glycerol backbone, our internal oxygen content is 30% higher than that of FAME, resulting in superb emission profiles as against petrodiesel, used as control fuel in our engine and emission tests, performed in an accredited laboratory.

 

 

 

                

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

                                      "Smoke emission diagram"

 

 

So fuel properties of TOMS render this renewable fuel applicable in diesel engines in unblended form as well (as TOMS100, a stand-alone biofuel), also in stationary applications, that is generating "green electricity" .

 

With the granting of our patents, our 1 and 3/4 years of priority over two Chevron patents, pertaining to the same fuels and manufacturing process, has been acknowledged (US 8,324,413 and 8,361,172).

 

Also, Hycagen Ltd of Cambridge (UK) has conducted expertiments on gensets (electricity generation) with the same chemical structures as our TOMS fuel ("Hycadiesel"), affording excellent results for off-road applications, see here:

 

http://www.realwire.com/releases/New-bio-fuel-shows-excellent-potential-for-stationary-power-applications

 

 

TOMS2 potentials:

 

Via separating our two components, that is modified triglycerides (mTG’s, partially containing short acyl groups besides original long ones) and (m)ethyl esters of fatty acids (FAME/FAEE), the mTG’s serve a number of purposes, e.g. yielding lowered calorie fats for dietary purposes/supplements (approved in the EU, USA, Brazil, see under "Salatrim", "Benefat", "Acetofat", etc.), novel building blocks (precursors) for novel bio-polymers, bio-lubricants, bio-hydraulic fluids, etc., that is they are applicable as high value added, most versatile products, tailored/designed to fit a given function, thereby highly diversifying our product portfolio and greatly extending product potentials. Now, it must be evident to everyone, that in case we provide novel triglycerides as novel feedstocks (biomonomers/derivatized biomonomers), dozens and dozens of new bioplastics (biopolymers) could be synthesised, with novel and unexpected properties, immensely diversifying feedstock availability and thus product portfolio as well, thus opening up a new avenue into the realm of material sciences. Also, novel biohydraulic fluids, biolubricants, non-ionic emulsifiers, could be synthesised with our highly variable modified triglycerides, etc.

 

In all such cases side-product being conventional biodiesel (FAME, FAEE), producable at much lower costs than by ordinary biodiesel manufacturers, the high-priced mTG co-products well offsetting the former’s manufacturing costs, thus rendering it really competitive with petrodiesel.

 

Again, to verify our strivings, here is a link on the work of Michigan State University researchers, who are targeting genetic modification of oil-bearing plants to produce just those structures that we are protecting in our patents ("acetylated glycerides"):

 

http://research.msu.edu/stories/research-promises-healthier-vegetable-oil-%E2%80%93-and-tractor-fuel-harvest-it

 

Side chain potentials:

 

Not only triglyceride-based bioplastic monomers but biopolyamide precursors are also capable of being produced via our methodology, combining those with well known and industrially practiced reactions.

 

Just one example. As is well known, castor oil is a precious feedstock for various polyamide precursors, in the recent drive to replace petrochemical derived counterparts. E.g. out of its appr. 90% ricinoleic acid composition, PA 9,9, PA 10,10 PA 11,11 and PA12,12 monomers can be produced. Based on our proprietary process and using our interesterification methodology, however this time not partially, but totally interesterifying e.g. castor oil with ethyl acetate, we get a mixture of triacetin (a widely used emulsifier, food additive with E number E1518, an anti-knock agent in gasoline, a solvent in flavourings, etc.), plus ethyl esters of ricinoleic acid, and also in minor volumes ethyl esters of stearic, palmitoleic and oleic acids, these latter utilized in many areas (cosmetics and food industries, etc.). After separating constituents of the mixture, and using conventional, industrially practiced conversion technologies, out of ricinoleic ethyl ester we get the following PA precursors:

 

azelaic acid,

sebacic acid,

undecanedioic acid,

dodecanedioic acid

 

It is to be noted, that via our routes we get a bifunctional precursor as well (half ester of dibasic acids, that is EtOOC-[CH2]n-COOH), this affording us the possibility to synthesise the omega-amino derivative as well (the amino group and the carboxylic acid group being on the same monomer, that is H2N-[CH2]n-COOH), accordingly not only types nylon AABB, but also nylon AB species can be produced in a most versatile manner.

 

Also, many intermediate products could find applications as bio-lubricants (e.g. lithium salt of 12-hydroxy-stearic acid, as a high performance, widely accepted lube-grease), bio-hydraulic fluids, etc., so the ever changing market forces could be well managed owing to our flexibility with respect to the broad portfolio of products.

 

Side products of the above PA monomer manufacturing processes are mainly C6, C7, C8 acids, capable of being transformed to omega-amino derivatives (e.g. 6-amino-caproic acid as PA6 monomer), etc., all these substances well known and routinely applied as industrial chemical raw materials.

 

Through combining our monomers, much demanded hybrid PA species may be synthesised (PA6,10), all of these upon bio-base.

Many of the above indicated reactions require optimization, verification and further R&D work, all this calling for involvement of teams of professionals. Such activity will necessarily result in creating all sorts of IP’s, affording in certain cases monopolistic manufacturing and market positions.

 

Summarizing all the above one must be assured, that from our new building blocks one is BOUND to get novel end products. And if you/we carefully design together these structures, success is BOUND to knock at your door. And this pertains to all fields where our mTG`s are to be utilized as new precursors for a variety of target products.

 

A

B

C

A; FAME

B; G-phase

C; TOMS, no glycerol, but + 15 - 20 % extra fuel mass