The present invention describes a procedure for the synthesis of p-cymene from monoterpenes or mixtures thereof, using dimethyl sulfoxide as an oxidizing agent and solvent, in the presence of a molybdenum catalyst. This sustainable and economically competitive route for the synthesis of p-cymene from renewable sources derived from biomass represents a viable alternative to the currently employed procedures. This procedure offers advantages in terms of selectivity, low toxicity, availability of raw materials, and ease of purification.
New and innovative aspects
The invention proposes a new method for the synthesis of p-cymene from monoterpenes or their mixtures derived from biomass, using dimethyl sulfoxide as an oxidizing agent and a dioxomolybdenum(VI) catalyst. This innovative approach overcomes the issues associated with previous techniques, such as the generation of isomeric mixtures, sensitivity to sulfur commonly present in some starting materials, and the use of toxic products. Additionally, the procedure is more efficient, safe, and sustainable, providing a promising alternative for the production of pure and high-quality p-cymene.
Main advantages of its use
- Obtaining pure p-cymene: The method allows for the synthesis of isomerically pure p-cymene through a simple distillation process.
- Use of biomass-derived monoterpenes: Renewable and low-cost starting materials are employed, such as crude gum turpentine and citrus oil generated as waste or byproducts in the paper and citrus juice industries.
- Low-toxicity oxidizing agent: Dimethyl sulfoxide is used as the oxidizing agent, which is biodegradable and easily removable from the reaction medium.
- Sulfur-resistant catalyst: The catalyst used is resistant to the presence of sulfur or its derivatives in the crude gum turpentine starting material.
- Mild reaction conditions: The synthesis is carried out at atmospheric pressure and a moderate temperature of 150 °C.
- Economic and safety considerations: The method is economical, easy to operate, and does not require toxic chemicals or an inert atmosphere in the reactions.
Specifications
- Starting material: Monoterpenes or mixtures thereof derived from biomass.
- Oxidizing agent: Dimethyl sulfoxide (DMSO) is used as a stoichiometric oxidizing agent and solvent in the reaction.
- Catalyst: A dioxomolybdenum(VI) catalyst is employed, specifically bis-(dimethylformamide)diclorodioxomolybdenum(VI), MoO2Cl2(dmf)2, in amounts of 3-5 mol%.
- Reaction conditions: The reaction is carried out at atmospheric pressure, at a temperature of 150 °C, and for a reaction time of 24 hours.
- Product purification: The obtained p-cymene is purified through extraction with different solvents and fractional distillation.
Applications
P-Cymene synthesis method described by scientists from the University of Burgos presents an economically sustainable alternative to the current method, which relies on toluene derived from non-renewable petrochemical resources.
The synthesized p-cymene has various applications in industries such as perfumery, pharmaceuticals, herbicides, dyes, polymers, and high-value chemicals. The new methodology provides a more efficient way, utilizing industrial waste and/or renewable resources derived from biomass, to obtain pure p-cymene. This benefits these industries in terms of product quality, cost reduction, and sustainability.
Intellectual property status
Protected by patent P202330367
Current development status
Prototype available for demonstration.
Desired business relationship
Trade Agreement, License Agreement, Technical cooperation: further development, Technical Cooperation: testing of new applications; Technical Cooperation: adaptation to specific needs.
Intellectual property status
The aim of the Technology Transfer Office (TTO) of the Universidad de Burgos is to promote Innovative technology through the research results transfer and the connections between the University and the new needs and requirements of society - we are the link between the University and the Industry.
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