Fraunhofer Institute for Interfacial Engineering and Biotechnology IGBFraunhofer IGB in Straubing converts monoterpenes into new fine and bulk chemicals for a wide range of applications in the chemical industry. In addition to sustainability aspects, the aim is also to introduce new properties through the chemical structures provided or existing in nature.
Monoterpene Derivatives for the Chemical Industry
Monoterpenes: a versatile class of substances from nature's chemical building block set
Use of renewable raw materials for sustainable chemistry
Replacing petrochemical feedstocks in the chemical industry with renewable resources is a suitable strategy for increasing the sustainability of chemical products. However, not all potential raw material sources are being sufficiently exploited yet; industrial waste streams in particular offer untapped potential. The monoterpene substance class is particularly important in this context.
Raw materials with potential: terpene-containing residues in the pulp, juice, and MDF industries
Monoterpenes are secondary metabolites that occur in plants, fungi, and microorganisms. They are available in relevant quantities as by-products of the pulp and juice industries or in the manufacture of HDF boards.
Fraunhofer IGB is exploiting the potential of natural monoterpenes and investigating synthesis routes for their conversion into new fine and bulk chemicals for a wide range of applications in the chemical industry.
Monoterpenes are secondary metabolites found in plants, fungi, or microorganisms.
Our solution: Monoterpene platform for the production of fine and bulk chemicals
Fraunhofer IGB in Straubing converts monoterpenes into new fine and bulk chemicals for a wide range of applications in the chemical industry. In addition to sustainability aspects, the aim is also to introduce new properties through the chemical structures provided or existing in nature.
Monoterpenes: good functionalizability and a wide range of applications
Chemically, monoterpenes are easily accessible for chemical functionalization due to their double bonds. Terpenes can thus be converted into alcohols, amines, esters, thiols, and much more through further reactions.
The potential application areas are diverse and include polyesters, polycarbonates, polyamides, and resins & coatings. Additives such as plasticizers or nucleating agents can also be produced on the basis of monoterpenes. Monoterpenes and their derivatives are also used in cosmetics and as fragrances.
Synthesis according to the principles of green chemistry and sustainability
The BioCat branch of Fraunhofer IGB in Straubing is working on the development of a monoterpene platform that will provide sustainable products for the plastics industry and beyond. The principles of green chemistry, the EU's sustainability goals, and the approach of the European SSbD (Safe and Sustainable by Design) concept are taken into account in the synthesis design from the outset. A deep understanding of structure-property relationships enables targeted adaptation to the respective requirements of the products.
Applications of our monoterpene platform
Polyamides and caramides
Monoterpene-based polyamides and caramides
Due to their structure, which can be described as substituted cyclohexene, many monoterpenes are suitable as precursors for lactams. Lactams are typical monomers for polyamides. Camphor, α-pinene, limonene, and 3-carene have already been converted into polyamides. Typically, the synthesis of lactams proceeds in four stages: epoxidation, Meinwald rearrangement, oxime synthesis, and Beckmann rearrangement.
Synthesis of caranlactams
Caramide: bio-based polyamide from caranlactam
Based on 3-carene, 3S-caranlactam and 3R-caranlactam are two 100 percent bio-based, isomeric lactams that differ significantly in their properties in their polymer form – caramide – and thus potentially cover a wide range of applications. The thermal properties of caramide are particularly noteworthy, with a glass transition temperature (Tg ) of up to 120°C and a melting point (Tm ) of up to 280°C.
In addition, the crystallinity can be adjusted as required by combining 3S- and 3R-caranlactam or combining it with commercial lactams such as capro- and laurinlactam. Compared to commercial biopolyamides, which are composed of amines and acids, (caran)lactams can be converted into so-called cast polyamides. These are characterized by a particularly high molecular weight, excellent mechanical properties, and a crystallinity of over 50 percent.
Fraunhofer collaboration projects: SUBI2MA and VITAL
Caramides are being developed in collaboration with partners from industry and other Fraunhofer institutes. Since the first synthesis of caranlactam monomers at Fraunhofer IGB more than ten years ago, major steps have been taken together in the development of a commercial product. Particularly noteworthy are the Fraunhofer flagship project SUBI2MA (Fraunhofer IAP, IGB, ICT, ITWM, IWM, LBF) and the EU project VITAL (Fraunhofer IAP, IGB, ICT).
First-ever scale-up of monoterpene-based lactam monomer production to an industrial scale
The lactam monomers can be produced in a safe and scalable process on a kilogram scale. This process has already been successfully implemented at a contract manufacturer. Purification is achieved by simple crystallization. Caranlactam is the only monoterpene-based lactam to date that has been produced in industrial dimemsions.
Monomer caranlactam after scaling up to kilogram scale with a contract manufacturer
Caranlactam monomer before purification
Caranlactam monomer after purification (purification carried out at Fraunhofer CBP)
Polymerization and further development for a wide range of applications
Polymerization is carried out by anionic or hydrolytic polymerization. Caramide can then be further processed into filaments, foams, or sheets.
Demonstration of various applications: Further processing of caramides into cast polyamide sheets (Fraunhofer IGB),
fibers (monofilaments, Fraunhofer IAP),
and foams (Fraunhofer ICT).
(Meth-)acrylates
Monoterpene-based (meth)acrylates
(Meth)acrylates based on monoterpenes have been known for a long time, but only one representative, isobornyl(meth)acrylate IBO(M)A, is commercially available to date. IBOMA is used in a wide variety of applications such as UV lacquers & coatings, UV adhesives, technical acrylic resins, and 3D printing resins.
At Fraunhofer IGB in Straubing, a new class of monoterpene-based methacrylates and acrylates has been developed which, thanks to their adjustable monomer structure, can be used in a wide range of applications with a high formulation content.
We can specifically adjust the following properties, among others:
- Thermal properties (Tg)
- Polarity
- Viscosity
- Number and type of functional groups
The new monomers are synthesized using inexpensive, sustainable, and established methods and can be easily integrated into existing formulations and co-polymerized. The technology, which is currently being patented, will be presented in detail here once the patent has been granted.
Range of services and collaboration
Our services at a glance
- Functionalization of terpenes according to customer requirements, even beyond the world of plastics
- As fragrances for cosmetics, cleaning agents, etc.
- Provision of sample quantities
- Literature studies
- Established network for synthesis, scaling, polymerization, testing, digitization, LCA, and much more for terpene-based substances
Collaboration
Please contact us if you want to switch your raw materials to renewable resources and use industrially available biogenic residues! In an initial no-obligation meeting, we will show you the possibilities of our monoterpene platform and its diverse applications. We will be happy to first examine the feasibility of your or our joint idea and provide you with a tailor-made offer.
Video: Bio-based high-performance plastics from terpenes at the K trade fair
Video available in German.
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