A mild and practical oxidation process of thiophene derivatives in continuous-flow has been developed. The oxidant phase consists of mCPBA and acetonitrile, which formed an immiscible liquid-liquid segmented flow with the fuel phase. In the oxidation of thiophenes, high yields of sulfone could be realized with only 10 min of residence time in the microreactor. The oxidant phase can be separated with the fuel phase with a continuous membrane separator, rendering it a clean and potentially scalable method to facilitate fuel refining.
This is a preview of subscription content, access via your institution.
Buy single article
Instant access to the full article PDF.
Tax calculation will be finalised during checkout.
Fox EB, Liu Z-W, Liu Z-T (2013) Ultraclean fuels production and utilization for the twenty-first century: advances toward sustainable transportation fuels. Energy Fuel 27:6335–6338
Ho TC (2004) Deep HDS of diesel fuel: chemistry and catalysis. Catal Today 98:3–18
Röthlisberger A, Prins R (2005) Intermediates in the hydrodesulfurization of 4,6-dimethyl-dibenzothiophene over Pd/γ-Al2O3. J Catal 235:229–240
Ishihara A, Wang D, Dumeignil F, Amano H, Qian EW, Kabe T (2005) Oxidative desulfurization and denitrogenation of a light gas oil using an oxidation/adsorption continuous flow process. Appl Catal A Gen 279:279–287
Desai LV, Malik HA, Sanford MS (2006) Oxone as an inexpensive, safe, and environmentally benign oxidant for C−H bond oxygenation. Org Lett 8:1141–1144
Cravotto G, Garella D, Carnaroglio D, Gaudino EC, Rosati O (2012) Solvent-free chemoselective oxidation of thioethers and thiophenes by mechanical milling. Chem Commun 48:11632–11634
Yu B, Liu A-H, He L-N, Li B, Diao Z-F, Li Y-N (2012) Catalyst-free approach for solvent-dependent selective oxidation of organic sulfides with oxone. Green Chem 14:957–962
Jereb M (2012) Highly atom-economic, catalyst- and solvent-free oxidation of sulfides into sulfones using 30% aqueous H2O2. Green Chem 14:3047–3052
Duarte TAG, Pires SMG, Santos ICMS, Simões MMQ, Neves MGPMS, Cavaleiro AMV, Cavaleiro JAS (2016) A Mn(iii) polyoxotungstate in the oxidation of organosulfur compounds by H2O2 at room temperature: an environmentally safe catalytic approach. Catal Sci Technol 6:3271–3278
Timko MT, Wang JA, Burgess J, Kracke P, Gonzalez L, Jaye C, Fischer DA (2016) Roles of surface chemistry and structural defects of activated carbons in the oxidative desulfurization of benzothiophenes. Fuel 163:223–231
Camurlu P, Durak T, Balan A, Toppare L (2011) Electronic and optical properties of dibenzothiophen-S,S-dioxide and EDOT based conducting polymers. Synth Met 161:1898–1905
Tang N, Jiang Z, Li C (2015) Oxidation of refractory sulfur-containing compounds with molecular oxygen catalyzed by vanadoperiodate. Green Chem 17:817–820
Kamata K, Sugahara K, Kato Y, Muratsugu S, Kumagai Y, Oba F, Hara M (2018) Heterogeneously catalyzed aerobic oxidation of sulfides with a BaRuO3 nanoperovskite. ACS Appl Mater Interfaces 10:23792–23801
Akwi FM, Watts P (2018) Continuous flow chemistry: where are we now? Recent applications, challenges and limitations. Chem Commun 54:13894–13928
Gemoets HPL, Su Y, Shang M, Hessel V, Luque R, Noël T (2016) Liquid phase oxidation chemistry in continuous-flow microreactors. Chem Soc Rev 45:83–117
Colomer JP, Traverssi M, Oksdath-Mansilla G (2020) Oxidation of organosulfur compounds promoted by continuous-flow chemistry. J Flow Chem 10:123–138
Rahimi M, Shahhosseini S, Movahedirad S (2017) Continuous-flow ultrasound assisted oxidative desulfurization (UAOD) process: an efficient diesel treatment by injection of the aqueous phase. Ultrason Sonochem 39:611–622
Laudadio G, Straathof NJW, Lanting MD, Knoops B, Hessel V, Noël T (2017) An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor. Green Chem 19:4061–4066
Noguchi T, Hirai Y, Kirihara M (2008) Highly selective 30% hydrogen peroxideoxidation of sulfides to sulfoxides using micromixing. Chem Commun 26:3040–3042
Piscopo CG, Voellinger L, Schwarzer M, Polyzoidis A, Bošković D, Loebbecke S (2019) Continuous flow desulfurization of a model fuel catalysed by titanium functionalized UiO-66. ChemistrySelect 4:2806–2809
Ogunlaja AS, Walmsley RS, du Sautoy C, Torto N, Tshentu ZR (2013) Development of a continuous flow system for the oxidative desulfurization of refractory organosulfur compounds in hydrotreated diesel. Energy Fuel 27:7714–7723
This work was supported in part by the National Natural Science Foundation of China (grant 21872068) and the Fundamental Research Funds for the Central Universities (grant 0205-14380182).
Conflict of interest
The authors declare no conflict of interest.
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic supplementary material
About this article
Cite this article
Wang, S., Patehebieke, Y., Zhou, Z. et al. Catalyst-free biphasic oxidation of Thiophenes in continuous-flow. J Flow Chem 10, 597–603 (2020). https://doi.org/10.1007/s41981-020-00102-9
- Continuous-flow oxidation
- Liquid fuel
- Biphasic oxidation