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Validation of an industrial process to manufacture isosorbide bis(methyl carbonate) at pilot level

Periodic Reporting for period 2 - VIPRISCAR (Validation of an industrial process to manufacture isosorbide bis(methyl carbonate) at pilot level)

Reporting period: 2019-12-01 to 2021-05-31

The VIPRISCAR Project is addressing new solutions to relevant problems that affect modern societies because of the scarcity of fossil resources and the negative health and environmental impacts related to them. VIPRISCAR has developed new monomers and polymers from lignocellulosic biomass that partially replace their petroleum-derived homologs in a safer, and environmentally more benign approach.

The Project works with Isosorbide, a commercial primary bio-based monomer obtained from glucose by dehydration of D-sorbitol. More precisely VIPRISCAR has created a new scalable process to an isosorbide derivative: isosorbide bis-methyl carbonate (IBMC) is a promising candidate to replace petroleum-derived toxic bisphenol-A in polycarbonates production, or to avoid di-isocyanates in the production of new non-isocyanate polyurethanes (NIPUs).

VIPRISCAR has successfully achieved the principal objective initially marked which was to validate a highly efficient IBMC production process in an industrially relevant environment (TRL 5), able to be up scaled and to be produced, under suitable market conditions. Other objectives proposed were also successfully achieved as showing proof of principle methods and prototypes to launch IBMC in high-volume market sectors as industrial coatings and adhesives, although more R&D activity is needed to achieve the required characteristics.

This impacts in the society because IBMC is a green alternative to the synthesis monomers that can replace other petro-derived equivalents but do not contain toxic substances as phosgene, diphosgene, or DPC in their composition. The use of IBMC in different polymers manufacture will impact giving substantial advantages related to the security and environmental benefits of the production processes and improvements in the safety and biodegradability of the final products.
As a general overview, the work performed, and the principal results achieved have been:

1. A robust process for manufacturing IBMC with a purity ranging from 90 to > 99 wt% has been developed. Different qualities of isosorbide can be used from high acidic isosorbide to neutral one.

2.An IBMC purification procedure has been developed to achieve IBMC purity ≥ 99% based on non-energetically intensive technologies as nanofiltration and lixiviation.

3.An optimal pilot process for IBMC production has been developed with a targeted cumulative production of ≥100-kg IBMC, moving the TRL of VIPRISCAR from 4 to 5.

4.At least 186-kg IBMC has been produced and harvested for long-term storage from a varying spectrum of pilot runs performed in the pilot reactor. The results obtained include the full protocol of IBMC production, the constituents of the harvested IBMC, as well as discussion on drying and storage considerations of the product. This result validates the achievement of the principal objective marked in the VIPRISCAR project.

5.The profitability of the process has been optimized achieving a recovery of unreacted DMC in this pilot process of 85% of the original reactant employed.

6.A full-scale industrial plant has been simulated that indicates the investment required for future cooperation with investors. (3 scenarios of IBMC consumption have been considered for a more precise evaluation).

7.IBMC-based hydroxyl-functional oligocarbonates from polycondensation reactions of IBMC with different diols, catalysts and solvents has been synthesized.

8.NIPUs have been synthesized by reaction of IBMC with diamines, in the presence of various catalysts and solvents and using different polymerization processes (bulk polymerization, interfacial polymerization and miniemulsion polymerization).

9.The polyols obtained present low molecular weights for their use in the application of adhesive formulation and in the production of catheter, but the products show promising characteristics and good quality to be used in coating applications.

10.VIPRISCAR has developed the conceptual design and basic engineering for the IBMC production process, including all mass and energy balances and basic equipment utilized. These technological results are complemented with the toxicological evaluation of IBMC. All the tests required by REACH regulation for the toxicological evaluation has been carried out concluding that IBMC did not produce any negative result.

11. An exploitation plan has been carried out considering three scenarios and the results have been disseminated and communicated in various congresses and scientific publications, as well as the production of a video. All this information is accessible through the project website https://vipriscar.eu/
The results obtained in the VIPRISCAR project go beyond the state of the art since they deal with different technological and safety aspects that were never previously considered.

• VIPRISCAR deals with the principal handicap of the production cost of the new biobased monomer by developing a very robust IBMC production process that can consider different isosorbide qualities that can compete in the market with different prices. This implies technological advantages that permit the consideration of IBMC as a commodity intermediate of constant supply for a variety of polymerization processes. Depending on the isosorbide acidity two production processes based on heterogeneous catalysts, or homogeneous nitrogenated bases have been developed. IBMC of purity higher than 90% is always obtained whatever the isosorbide acidity, being adequate for any polymerization application.

• The operational conditions employed for the synthesis of IBMC at the pilot-scale (TRL 5) and the plant design have been optimized to minimize costs. 3 future industrial IBMC production scenarios based on real experimental data have been evaluated to quantify the success possibilities of the IBMC production implementation at an industrial scale. The results obtained are favourable for a future DEMO scale-up of the technology developed in the VIPRISCAR project.

• The incorporation of IBMC in polycarbonates and NIPUs production has originated several innovative synthesis routes, in particular, new coatings with relevant bio-based content and favourable properties have been developed. For the first time, IBMC based PUDs have been developed (TRL 3) to be used as raw materials for new IBMC-derived waterborne proof-of-principle coatings with the carbonate functionality and the rigid two-ring structure from isosorbide within the macromolecular network.

• Amino-terminated NIPUs are a completely novel class of epoxy hardeners that have been designed and synthesized also for coating applications. These hardeners had shown good potential to be used in coating formulations, resulting in good appearance, stain resistance, and adhesion.

• Amino-terminated NIPUs prepolymers have been developed in dispersed media for incorporation into acrylic pressure-sensitive adhesives formulations as stable hybrid systems with promising properties but it is needed more R&D activity to achieve the required characteristics.
IBMC coating
IBMC
IBMC obtained at pilot scale
IBMC obtained at lab scale