"Substituted furfuryl alcohols are extraordinarily versatile starting materials in synthesis. They are precursors to furanoxonium ion intermediates which are implicated in the Piancatelli reaction (leading to 2-cyclopentenones) and in the synthesis of novel dihydrofuran-based exo enol ether/cyclic ketal natural products."...
Bio (plant)-based chemicals are the unexpected beneficiaries of the North American shale gas boom .. Sugars, glycerin and other plant-derived feedstocks are emerging as economically competitive starting materials for a range of commodity chemicals, in part, because of tight supplies of conventional feedstocks such as propylene, isobutylene, butadiene and isoprene.
Bio-renewables can replace petro-chemicals. Some 65 years ago (!!), furfural was destined to be the feedstock for Nylon (see "Historic Background": dalinyebo.com/furfural-market).
Selectively cleaving the CO bond outside the furan ring of furfural is crucial for converting this important biomass-derived molecule to value-added fuels such as 2-methylfuran. In this work, a combination of density functional theory (DFT) calculations, surface science studies, and reactor evaluation identified molybdenum carbide (Mo2C) as a highly selective deoxygenation catalyst for converting furfural to 2-methylfuran. ..
2-Methylfuran is a flammable, water-insoluble liquid with a chocolate odor, found naturally in Myrtle and Dutch Lavender used as a FEMA GRAS flavoring substance, with the potential for use in alternative fuels (wikipedia.org).
It is also used as a basis for the synthesis of many pharmaceutical, agricultural and industrial chemicals (dalinyebo.com/platformchemical)
A pioneering study has proposed a new integrated method for producing aviation fuels from woody feedstock by considering all downstream processing stages and carrying out a detailed economic analysis. Lignocellulose, a raw material in biomass, can be converted to biofuels and is often considered a long-term alternative to the diminishing supply of fossil fuels. The conversion process involves biomass pretreatment, hydrolysis of constituent carbohydrates and catalytic conversion of platform chemicals. Proposed strategies to convert lignocellulose to aviation fuels have underused components, preventing their commercialisation.
Furfural production should be an integrated unit-process of every lignocellulosic biorefinery (see Paid4Pretreatment™), as it offers the best use of the C5-molecule for the conversion into fuels (example: C10 and C11 branched alkanes, with low freezing points, are synthesized through the aldol condensation of furfural and methyl isobutyl ketone).
One-pot selective conversion of highly concentrated furfural to 1,5-pentanediol (1,5-PeD) was carried out over Rh-added Ir-ReOx/SiO2 catalysts through two-step reaction temperatures."...
Reduced to one production step: This most probably opens another avenue for competitive production of 1,5-pentanediol (PDO, or pentane-1,5-diol), which sells at ±US$9,000/t (http://en.wikipedia.org/wiki/1,5-Pentanediol). The conventional pathway to PDO from furfural was via multi-step hydrogenation (via THFA/Methyl-THF).
Pentane-1,5-diol is a valuable intermediate for the chemical industry. It finds applications in a variety of polymeric systems and is also used in the synthesis of specialty chemicals such as thermoplastic polyurethanes and polyester resins. Its most important uses include plasticizers, pharmaceuticals, crop protection agents, cosmetics as well as and inks and coatings. One of the benefits of Pentane-1,5-diol (PDO) is that it was found to be safe and more effective than several other diols with respect to pharmaceutical and cosmetic properties (www.basf.com).
Center for Catalytic Science and Technology (CCST): The renewable production of chemicals and fuels from biomass is inherently difficult due to competing side reactions. CCST has demonstrated the selective production of phthalic anhydride, a chemical used for the manufacture of plasticizers, unsaturated polyesters, and resins in the millions of tonnes per year, from biomass ..
Malaysia is keen on valorizing its significant volume of palm tree biomass into biobased chemicals and bioplastics. Malaysia reportedly produces around 80 million tons/year of biomass waste.
We think that furfural and its many by-products could be the first (and easy) step in conditioning the biomass for the production of other bio-renewable chemicals and polymers. See dalinyebo.com/palm-residues
El bagazo es la biomasa para producir electricidad de más importancia en América Latina hasta ahora. Ejemplo en Honduras.
dalinyebo.com/bagasse adds value to bagasse prior to it being burnt. For smaller mills, micro-BioRefinery.com offers a smart and innovative approach for a combined heat and power solution that's on 'steroids'
Abstract: Upgrading of furan and small oxygenates obtained from the decomposition of cellulosic materials via formation of carbon-carbon bonds is critical to effective conversion of biomass to liquid transportation fuels. Simulation-driven molecular level understanding of carbon-carbon bond formation is required to design efficient catalysts and processes. Accurate quantum chemical methods are utilized here to predict the reaction energetics for conversion of furan (C4H4O) to C5-C8 ethers and the transformation of furfural (C5H6O2) to C13-C26 alkanes. ...
Hydrolysis meets Pyrolysis!
Interesting Furan Chemistry: Vapour phase catalysis for upgrading of furans/furfurals to longer chain hydrocarbons. (also see www.dalinyebo.com/tag/biofuels).
Biochemical conversion of biomass involves use of bacteria, microorganisms and enzymes to breakdown biomass into gaseous or liquid fuels, such as biogas or bioethanol. The most popular biochemical technologies are anaerobic digestion (or biomethanation) and fermentation. Anaerobic digestion is ...
Why not be smarter?
(A) The biomass pretreatment does not have to be a cost (see dalinyebo.com/Paid4PreTreatmet).
(Z) In our humble opinion, it is a waste to 'destroy' about ±60% of the pentoses in the process of fermenting them to ethanol (see dalinyebo.com/Cellulosic-Plus).
Self-assembled nanoparticulates of porous sulfonated carbonaceous TiO2 material that contain Brønsted and Lewis acidic sites were prepared by a one-pot synthesis method. ... The carbonaceous heterogeneous catalyst (Glu-TsOH-Ti) with a Brønsted-to-Lewis acid density ratio of 1.2 and more accessible acid sites was effective to produce 5-hydroxymethylfurfural and furfural from biomass-derived mono- and disaccharides and xylose in a biphasic solvent that comprised water and biorenewable methyltetrahydrofuran....
HMF can be converted to 2,5-dimethylfuran (DMF), which is a liquid biofuel with a greater energy content bioethanol. Oxidation of HMF gives 2,5-furandicarboxylic acid, which has been proposed as a replacement for terephthalic acid in the production of polyesters. It can also be converted to gamma-valerolactone, 2,5-furandicarboxylic acid or 2,5-bis(hydroxymethyl)furan. (wikipedia.org).
Furfural and 5-hydroxymethylfurfural (HMF) are the degradation products of lignocellulose during pretreatment operations and significantly inhibit the consequent enzymatic hydrolysis and fermentation processes. The biodetoxification fungus Amorphotheca resinae ZN1 had demonstrated its excellent capacity on degrading lignocellulose derived inhibitors and helped the fermentation processes to achieve high yield of ethanol and biochemicals ...
Provided the furfuryl/HMF alcohols can be recovered economically, this process may add another pathway to furfural chemistry.
1,2-pentanediol is a key ingredient for the cosmetic industry and an intermediate for agricultural applications and other specialty markets. Additional production facilities will come on stream in the fourth quarter of 2014 at the Memphis site of Pennakem, LLC.
1,2-Pentanediol (Eco certified pentylene glycol) is synthesised from furfural via furfuryl alcohol. Biobased 1,2-Penanediol helps the cosmetics industry to offer its consumers products that are made environmental friendly (and in this case: made from corncobs or sugarcane bagasse).
The Palm Oil industry generates large quantity of wastes whose disposal is a challenging task. In the Palm Oil mill, fresh fruit bunches are sterilized after which the oil fruits can be removed from the branches. The empty fruit bunches (are left as residues, and the fruits are pressed in … ...
It does not have to be like that!
It seems that there are no obvious off-the-shelf solutions, but there are pathways to turn 'waste' into revenue. For close to 15 years, we have been developing technologies to convert agricultural residues into bio-renewable chemicals and energy and have also evaluated selected biomass from the palm oil industry. Our approach is only one step towards the solution, but an important step, as in essence we "condition" the biomass to make further processing easier and in doing so, we make money from extracting a high value chemical, which we are able to trade into global niche markets.
Here's the link to our proposal: dalinyebo.com/palm-residues
Next breakthrough: carbon fiber from Biomass. En route to a totally sustainable airplane! The Energy Department of the U.S.(DOE) recently announced up to $12 million in funding to advance the production of cost-competitive, high-performance carbon fiber material from renewable non-food-based feedstocks such as agricultural and forestry residues.
We suggest that some of the furfural by-products should be considered. There are a variety of avenues that lead to e.g. thermoset-resin-biofibre composites or high-temperature polymers.
The Furfural Refining process is a solvent extraction process used to remove undesirable components of low lubricating oil quality naturally present in crude oil distillate and residual stocks. The unit produces paraffinic or naphthenic raffinates suitable for further processing into lube base stocks.
This process has been used for over 60 years in more than 100 refineries worldwide to produce high-quality lubricating oils characterized by high viscosity index, good thermal and oxidation stability, light color, and excellent additive response. The process selectively removes aromatics and compounds containing heteroatoms (e.g., oxygen, nitrogen, sulfur, and metals). The by-product extracts, being high in aromatic content, can be used for carbon black feedstocks, rubber extender oils, and other non-lube applications where this feature is desirable.
This process is one of oldest and largest users of furfural.
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