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Innovative procedure for the sustainable synthesis of p-cymene from renewable sources derived from biomass

Summary

Profile Type
  • Technology offer
POD Reference
TOES20230720010
Term of Validity
20 July 2023 - 19 July 2025
Company's Country
  • Spain
Type of partnership
  • Research and development cooperation agreement
  • Commercial agreement with technical assistance
Targeted Countries
  • All countries
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General information

Short Summary
The 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.

They are looking for commercial and research cooperation agreements.
Full Description
The research group has a well-proved expertise in the development of new procedures of quickly, efficiently, and sustainably methodologies. Additionally, during the last years, this group has stablished an important number of contracts with different companies related to organic chemistry.

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 sulphur 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 to produce pure and high-quality p-cymene.

• 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.

The research group is interested in contact with different partners. Commercial agreements are sought and partners for research cooperation agreements are welcome as well.
Advantages and Innovations
This procedure offers advantages in terms of selectivity, low toxicity, availability of raw materials, and ease of purification.

• 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.
• Sulphur-resistant catalyst: The catalyst used is resistant to the presence of sulphur 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.
Stage of Development
  • Available for demonstration
Sustainable Development Goals
  • Goal 12: Responsible Consumption and Production
IPR status
  • IPR applied but not yet granted

Partner Sought

Expected Role of a Partner
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. Their role will be, for instance, to use this technology to improve their procedures.

In addition, they are looking for a research groups and research institutions to collaborate to transfer and bring the technology to the next level and, additionally, apply for European funds.
Type and Size of Partner
  • SME 50 - 249
  • R&D Institution
  • Other
  • Big company
  • SME <=10
  • University
  • SME 11-49
Type of partnership
  • Research and development cooperation agreement
  • Commercial agreement with technical assistance

Dissemination

Technology keywords
  • 001001004 - Electronic engineering
  • 09001004 - Electrical Technology related to measurements
Market keywords
  • 03004002 - Components testing equipment
  • 08003001 - Machine tools, other metal working equipment (excl. numeric control)
  • 09003001 - Engineering services
Targeted countries
  • All countries