IFT: Bio-renewable Chemicals Technology

Levulinic Acid from Furfuryl Alcohol in THF Solvent Systems

Furfuryl alcohol was hydrolysed to levulinic acid with yields >70%. (ACS Catalysis)

American and Brazilian Researchers observed a reduction of the furfuryl alcohol polymerization reactions, when using a zeolite to hydrolyse furfuryl alcohol in THF (a furfural by-product) , thus increasing the yields over 70%.

Two extracts from their report explain the importance of their work:

Levulinic acid can be produced from the cellulose fraction (C6 sugars) of lignocellulosic biomass in high yields through a series of acid-catalyzed reactions, passing through the platform molecule hydroxymethylfurfural, as displayed in Scheme 1, however, the use of cellulose for the production of chemicals competes with the well-established bioethanol process. Hemicellulose (C5 sugars) can also be used to target the production of levulinic acid, as shown in Scheme 1.
Notably, the conversion furfuryl alcohol to levulinic acid is of fundamental importance because it is one of the few reactions that integrate glucose and xylose reaction pathways, associating xylose with the well-developed chemistry of cellulose-derived compounds.

Scheme 1 – Levulinic Acid Production Pathways from Biomass (ACS Catalysis)

Source: pubs.acs.org

DalinYebo‘s insight:

International Furan Technology (ift.co.za) provides knowhow on the design and construction of bio-based chemical plants using feedstock such as sugarcane or sweet sorghum bagasse.
The µ-BioRefinery (micro-biorefinery.com) is a design-platform for the processing of sweet sorghum and/or sugarcane into bio-based chemicals, such as furfural, butanol and could be easily adapted to Levulinic Acid production.

Levulinic Acid from Furfuryl Alcohol in THF Solvent Systems was originally published on DalinYebo.com: Bioeconomy Consultants : Innovative Minds

...

Source: https://dalinyebo.wordpress.com/2015/05/24/levulinic-acid-from-furfuryl-alcohol-in-thf-solvent-systems-2/

Furfural Derivatives And 170-Year-Old Champagne

SHIPWRECKED FIZZ: In 2010, divers found a cache of 170-year-old champagne in the Baltic Sea. (Credit: Visit Åland)

Analysis of furfural derivatives in the shipwrecked bubbly reveals secrets of 19th-century French wine making. The ancient and perfectly preserved champagne, which was taken from a shipwreck off the coast of Finland, revealed an array of curious facts about past wine-making practices. Chemical analysis of the vintage sparkling wine revealed particularly high levels of sugar and salt compared with modern-day champagne, as well as the presence of unexpected metals, likely used in 19th-century wine preservation and storage (Proc. Natl. Acad. Sci. USA 2015, DOI: 10.1073/pnas.1500783112).

Continue …...

Source: https://dalinyebo.wordpress.com/2015/04/21/furfural-derivatives-and-170-year-old-champagne/

A Truly Biobased TPA For PET

Biobased terephthalic acid (TPA) for polyethylene terephthalate (PET)

Although beverage companies like Coca-Cola Ltd. have adopted biobased-PET since 2009, they use petroleum based TPA and therefore the PET's percentage biomass carbon content is a mere 20%. In a February 2015 publication [1], researchers propose a viable synthetic route, shown in Figure 1 (below), for the preparation of biobased TPA from furfural alone, which is produced industrially from inedible cellulosic biomass.

Fig 1 - Furfural to TPA [1]

The researchers now aim to reduce the number of process steps to two and increase the overall yields.

Furfural is an ideal biomass resource, as it is traditionally produced from cellulosic and waste biomass such as corncob, corn stock, and rice hull. Furthermore, it is extremely abundant, with a global output of 500,000–1,000,000 tonnes/year.

Market:

PTA is expected to grow at a Compound Annual Growth Rate (CAGR) of 5.3% from 2011, reaching 66 million tons in 2020, with Asia-Pacific expected to account for around 82% of its demand. [2]

Also See:

Polyester From Furfural (November 2014)

Furfural as feedstock for PET alternatives (December 2013)

Important chemicals for the production of biomass-based monomers (Nov 2013)

Renewable platform chemical and building block (October 2013)

Moving the field of furfural and its by-products into the limelight it deserves

Reference:

[1] Synthesis and Verification of Biobased Terephthalic Acid from Furfural

[2] CBI Research: China and India to Lead Global Purified Terephthalic Acid Demand Growth by 2020 (accessed: 19 April 2015)

Bioeconomy Consultants: Connecting-The-Dots™

Since 2001, DalinYebo provides knowhow:

To convert biomass to value added products that are used in industries such as steel, wood, pharmaceutical, automotive, agricultural chemicals, industrial chemicals, etc.

For the agri (biomass) processing, sugar, pulp&paper, etc. industries, we provide knowhow and technology to convert (residual) biomass to chemicals and energy.

For owners of biomass we offer technology and market access, creating investment opportunities in the cleantech space.

The essential technical challenge facing us, and the world in general, is the complete beneficiation of cellulosic material. We strive to provide viable and practical solution. Contact us to discuss the economic potential of your biomass.

PET
Polyesters
Byproducts...

Source: http://www.dalinyebo.com/item/1216-a-truly-biobased-tpa-for-pet

Polyester From Furfural

Aiming for a small slice of the ±50million tpa (polyester) market.

Polyester is a synthetic polymer made of purified terephthalic acid (PTA). Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters [1]. The synthesis of furfural to FDCA is a two step reaction, via furoic acid [2]. It is very old chemistry that goes back to 1930s. Most recently commercial developments of FDCA is based on 5-Hydroxymethylfurfural (5-HMF) as precursor.

Growth: 2014 to 2020 forecast for FDCA is in the order of a CAGR of 367.0% [3, 4]

Market reports[4] forecast FDCA consumption by 2020 to be close to 500,000 tpa and that its market share should be in the following segments:

Grandview Research (Industry Analysis: FDCA-Industry)

Although there are uses for FDCA in market sectors such as PET, polyamides, polycarbonates, plasticisers and polyester polyols, the production of PET from FDCA is expected to have highest potential by 2020. This market segment is forecast to account for over 60% of global FDCA consumption.

Market:

By 2020, the FDCA Market volume is expected to reach about 500,000 tpa. [4]

Why FDCA from Furfural?

The current (semi-)commercial production of FDCA is made via 5-HMF, which is an unstable molecule and requires expensive catalysts for its synthesis. In addition, its commercial viability depends on large-scale production and is reliant on the food industry to supply sugars and/or starches.

Furfural is made on small-scale production units (biorefineries) that are close to the biomass suppliers or attached to a sugar mill (or pulp mill).

Furfural production does not interfere with food-production.

Furfural production contributes to food-security, as its beneficiaries are the farmers, whose crop "wastes" are used to generate additional revenue for them.

Furfural biorefineries have a high socio-economic impact: They require low capital investments and are suitable to be owned and operated by small enterprises or co-operatives and therefore have a direct impact on their local economies (inc. creation of green, rural jobs).

Editor's note: The Furfural-to-FDCA research goes back to the early 20th century. Since the 1970s, new catalysts, new process technology, etc. have been developed in the hydrocarbon-based chemical industry, which could also be applied in the bio-renewable chemicals space. The background IP for Furfural-to-FDCA is freely available and given the low-cost/energy efficient furfural production that is commercially available from International Furan Technology, there should be no reason to meet the targeted US$1,000 per tonne of FDCA.

Also See:

Furfural as feedstock for PET alternatives (December 2013)

Important chemicals for the production of biomass-based monomers (Nov 2013)

Renewable platform chemical and building block (October 2013)

Bioplastics: 500% growth = 500% more green chemicals (September 2013)

Furoic acid, is the oldest know furan derivative

Moving the field of furfural and its by-products into the limelight it deserves

References:

[1] Wikipedia: 2,5-Furandicarboxylic acid

[2] Map to Furfural By-products

[3] Bioplastics News: Great Future of Furanics Chemistry

[4] Grandview Market Research: Industry-analysis: FDCA-Industry

[5] B. Kamm, M. Kamm. M. Schmidt, T. Hirth and M. Schulze, Biorefineries – Industrial Processes and Products, ed. B. Kamm, P.R. Gruber and M. Kamm, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2006, vol. 2, ch. 3, pp. 97-149.