GFBiochemicals

Levulinic acid

Levulinic acid has been widely recognised as one of the top biobased platform chemicals of the future. It is a versatile building block with a clear value proposition in chemicals.

As the world moves from fossil to alternative feedstocks, levulinic acid can serve as an incredibly versatile building block for chemicals and materials derived directly from biomass.

Derivatives of levulinic acid can successfully address many performance-related issues attributed to petroleum-based chemicals and materials. GFBiochemicals is focused on commercialising levulinic acid derivatives through its joint venture business NXTLEVVEL Biochem BV.

Advantages

  • Versatility allowing a wide range of downstream transformations
  • Feedstock flexibility, high conversion yields, high productivity and concentrated process streams result in cost-competitive economics
  • Cost-competitive economics are key for fast and successful market introduction of functional derivatives, as well as substantial market growth in the coming years

Levulinic acid esters (LA-esters)

Levulinic acid esters are sold today as niche fruity flavour and fragrance ingredients. However, the increasing demand for green solvents has put levulinates on the mainstream agenda of the chemical industry. As petrochemical solvents are known to be harmful for humans and the environment, levulinic acid derivatives offer a safer and sustainable alternative.

Levulinic acid ketals (LA-ketals)

As plasticizers:

Levulinic acid-derived ketal plasticizers can replace major phthalate-based plasticizers which account for the majority of the world’s plasticizer market. Our plasticizers show excellent compatibility with hydrophilic biopolymers, like PLA, improving their flexibility and overall performance.

As polyol precursors:

Polyols based on levulinate ketals allow reduced isocyanate/catalyst content, no residual unsaturation and are highly compatible with other polyols. The ketal function allows fine tuning of the glass transition temperature to produce visco-elastic polyurethane foams.

Levulinic acid ketals (LA-ketals)

As solvents:

Levulinic acid esters and ketals are widely appreciated in many applications because of their broad solvency power, high coupling ability, low volatility, high safety profile, and biodegradability.

In the personal care industry, levulinate ketals can be used as formulation aids to dissolve a wide range of actives, thus expanding formulation flexibility and increasing concentration. By incorporating water into anhydrous systems they enable high water loading for moisturizing formulations. By expanding the solubility of ethanol they retaining clarity; By reducing the greasiness of natural formulations they enable the presentation of a dry, silky after-feel.

In other sectors such as industrial or home cleaning, levulinates deliver excellent degreasing/stain removal, are hugely efficient in removing paint, ink or adhesive and offer stable to concentrated formulations without clouding. Whilst for coatings, both the esters and ketals deliver exceptional performance as coalescents or co-solvents.

Our bio-based solvents offer price stability, stable supply and economic efficiency. They are a safe, environmentally responsible alternative to chlorinated solvents, glycol ethers, NMP, aromatic solvents and d-limonene.

FUTURE project

Gammavalerolactone (GVL)

Conversion of levulinic acid into GVL is proven with existing catalysts, resulting in high yields at reasonable operating conditions.

GVL has value advantages over traditional solvents because of its higher solvating power and lower vapor pressure.

GVL is an intermediate for monomers like adipic acid, caprolactam and specialty acrylates and for chemicals as like pyrrolidinone-isomers.

Methyltetrahydrofuran (MeTHF)

MeTHF can be produced from levulinic acid using hydrogenation technology and is a promising alternative solvent in the search for environmental friendly synthesis strategies.

Its physical and chemical properties, such as its low miscibility with water, boiling point, remarkable stability compared to other cyclic-based solvents such as THF, and others make it appealing for applications in syntheses involving organometallics, organocatalysis, and bio-transformations or for processing lignocellulosic materials.

It’s low miscibility with water, make of MeTHF an excellent solvent for extraction processes.

Methyl Butanediol (MeBDO)

Like GVL and MeTHF, MeBDO can be obtained from levulinic acid via hydrogenation reactions. Main application for MeBDO are specialty solvents for cometics and food flavors, as well as intermediate for polyesters and polyurethanes.

Future Development

Alpha-methylene-gammavalerolactone (alpha-mGVL)

Alpha-mGVL is a top-performing product as a glass transition temperature booster to increase functionality and performance of low-cost plastics. In Plexiglass, it improves hardness and scratch resistance. It has great potential in consumer electronics, like touchscreens.

Delta-amino levulinic acid (DALA)

Delta-amino levulinic acid (DALA) is a naturally-occurring chemical with a large variety of functions. It is used as a herbicide on lawns and certain grain crops. Increasingly strict environmental protection regulations indicate that the volumes of traditional pesticide chemicals will decrease significantly. DALA is a suitable replacement for traditional herbicides and pesticides. It is also used in pharmaceuticals for diagnosis and treatment of cancer (photodynamic therapy).

Diphenolic acid (DPA)

DPA is promising as a potential partial replacement for bisphenol A (BPA) in epoxy resins, by adding functionality such us improved cross-linking, covalently bonded plasticizers and so on.

WIDE VARIETY OF APPLICATIONS FOR LEVULINIC ACID AND IT’S DERIVATIVES

GFBiochemicals’ biobased levulinic acid and it’s derivatives offer a more sustainable solution for chemicals. It is made directly from biomass which allows for a whole new range of pricing compared to existing processes.

Personal care

Levulinic acid and its derivatives, like sodium levulinate, are used in organic and natural cosmetic compositions for perfuming, skin conditioning and pH-regulating purposes. They give inherent fresh odor, prevent wrinkles and stabilize formulations and emulsions.

Levulinate ketals can be used as formulation aids dissolving a wide range of actives, thus expanding the range of actives and increasing actives concentration; incorporating water into anhydrous systems, thus enabling high water loading for moisturizing formulations; expanding solubility of ethanol, while retaining clarity; and last, but not least, by complimenting to natural formulations to reduce greasiness, while offering a dry, silky after-feel.


Flavors and fragrances

In fragrances, levulinic acid has a creamy whiskey-like odour; in flavors, it is used in compositions to create caramel, butterscotch and maple flavors. In food applications, levulinic acid is used for multiple functions, for instance as pH regulator for formulation. The derivative levulinate ester is also a flavoring agent.

Levulinate ketals and esters solubilize fragrance ingredients and solids, compatibilize fragrances with soy waxes, reduce VOC content in fragrance solutions and act as phthalate-free fragrance fixatives.


Resins and coatings

Levulinic acid can be used for example in waterborne coatings to facitlitate the crosslinking process.

A derivative of levulinic acid, DPA can be used as a potential partial replacement for bisphenol A (BPA) in epoxy resins, by adding functionality such us improved cross-linking, covalently bonded plasticizers and so on.


Pharmaceuticals

Levulinic acid is used in anti-inflammatory medication (e.g. indomethacin), anti-allergy agents, mineral supplements (e.g. calcium levulinate) and transdermal patches.




Solvents

Levulinic acid esters and ketals, gammavalerolactone and MeTHF are derivatives of levulinic acid that are suitable solvents for a number of applications.

Ketals and ester levulinates are used in industries like metal cleaning, remanufacturing, industrial plants cleaning and Industrial & Institutional, levulinate ketals deliver excellent degreasing/stain removal, remove polymers (baked on epoxy, elastomers, etc.), are stable in concentrate formulations without clouding, while having a safe toxicology profile for workers, enabling reduced post waste treatment.

GVL has value advantages over traditional solvents because of its higher solvating power and lower vapor pressure.

MeTHF is appealing for applications in syntheses involving organometallics, organocatalysis, and bio-transformations or for processing lignocellulosic materials. It’s low miscibility with water, make of MeTHF an excellent solvent for extraction processes.


Polymers and plasticizers

Levulinic acid-derived ketal plasticizers can replace major phthalate-based plasticizers which account for the majority of the world’s plasticizer market. Demand is increasing for renewable, phthalate-free plasticizers as sustainability is driving manufacturers to consider alternatives to incumbent plasticizers, especially for biobased polymers and applications for children’s toys, as well as for products in contact with humans.


Agro-chemicals

Delta-amino levulinic acid (DALA) is a naturally-occurring chemical with a large variety of functions. It is used as a herbicide on lawns and certain grain crops. DALA is a suitable replacement for traditional herbicides and pesticides.

Moreover, our levulinic acid based solvents can be used as adjuvants to enhance the effectiveness of pesticides such as herbicides, insecticides, fungicides and other agents that control or eliminate unwanted pests. These products are easy to pour and spray, have low odor, are compatible with HDPE and their use does not require special equipment or procedures.