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Mikkola, Jyri-Pekka
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Publications (10 of 245) Show all publications
Khokarale, S. G. & Mikkola, J.-P. (2019). Efficient and catalyst free synthesis of acrylic plastic precursors: methyl propionate and methyl methacrylate synthesis through reversible CO2 capture. Green Chemistry
Open this publication in new window or tab >>Efficient and catalyst free synthesis of acrylic plastic precursors: methyl propionate and methyl methacrylate synthesis through reversible CO2 capture
2019 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270Article in journal (Refereed) Epub ahead of print
Abstract [en]

Methyl propionate (MP) and methyl methacrylate (MMA) are considered as industrially important precursors upon large-scale acrylic plastic production. The existing industrial synthetic protocols of these precursors utilize expensive catalysts accompanied with toxic and explosive gases such as carbon monoxide, ethylene and hydrogen. Herein, we for the first time report highly selective, catalyst-free and room temperature synthesis of MP and MMA precursors through organic superbase involved reversible CO2 capture approach. In short, initially equimolar mixture of organic superbase 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and methanol were reversibly reacted with molecular CO2 and the obtained switchable ionic liquid, [DBUH][MeCO3] further reacted with an equivalent amount of propionic anhydride or methacrylic anhydride to form MP or MMA, respectively. These reactions were accomplished in different solvents such as DMSO and methanol whereupon, in case of methanol, separation of reaction products occurs from in-situ formed DBU derivatives such as [DBU][propionate] or [DBU][methacrylate]. In case of both MP and MMA synthesis, after use of methanol as a solvent, good recovery of alcoholic solution of esters were achieved where 85% and 92% yields of MP and MMA were obtained, respectively.The molecular DBU was recovered using NaCl saturated alkaline solution. Further, the recovered MMA with methanol was polymerised to poly-MMA using a benzoyl peroxide induced free radical polymerisation process. The synthesis and separation of MP or MMA as well as recovery of DBU was monitored by NMR analysis. Hence, unlike DMSO, methanol not only performed as a regent in CO2 capture and as a solvent media in MP, MMA and poly-MMA synthesis but also assisted in the recovery of DBU from the reaction mixture. Most importantly, here we represented a more efficient, safer and single solvent based alternative synthetic approach for the synthesis of acrylic plastic precursors MP or MMA compared to existing industrial methods. Also, no toxic or expensive catalysts were required.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-157484 (URN)10.1039/C9GC00413K (DOI)
Available from: 2019-03-22 Created: 2019-03-22 Last updated: 2019-04-02
Shukla, S. K., Khokarale, S. G., Bui, T. Q. & Mikkola, J.-P. (2019). Ionic Liquids: Potential Materials for Carbon Dioxide Capture and Utilization. Frontiers in Materials, 6, Article ID 42.
Open this publication in new window or tab >>Ionic Liquids: Potential Materials for Carbon Dioxide Capture and Utilization
2019 (English)In: Frontiers in Materials, ISSN 2296-8016, Vol. 6, article id 42Article, review/survey (Refereed) Published
Abstract [en]

The nonvolatility, structure-tunability and high CO2 uptake capacity render ionic liquids (ILs) the most exciting materials for the carbon dioxide (CO2) capture and fixation to value-added chemicals. The aim of this mini-review is to give a brief idea about the development of the potential ILs for CO2 capture, the mechanism involved in the CO2 binding and the application of ILs in the conversion of CO2 to useful chemicals. The mechanisms and nature of interactions in between IL-CO2 have been discussed in terms of the nature of cation, anion, presence of functional group and the extent of interaction between the components of ILs. The fixation of CO2 to linear and cyclic carbonates and electroreduction of CO2 to carbon-rich fuels in ILs has been accounted in detail. At the end, future challenges in terms of commercializing the ILs for CO2 capture and utilization technology are discussed.

Place, publisher, year, edition, pages
Frontiers Media S.A., 2019
National Category
Other Chemistry Topics
Identifiers
urn:nbn:se:umu:diva-157480 (URN)10.3389/fmats.2019.00042 (DOI)000462456000001 ()
Available from: 2019-03-22 Created: 2019-03-22 Last updated: 2019-04-12Bibliographically approved
Samikannu, R., Shukla, S. K., Samikannu, A. & Mikkola, J.-P. (2019). Lutidinium-Based Ionic Liquids for Efficient Dissolution of Cellulose. New Journal of Chemistry, 43(5), 2299-2306
Open this publication in new window or tab >>Lutidinium-Based Ionic Liquids for Efficient Dissolution of Cellulose
2019 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 43, no 5, p. 2299-2306Article in journal (Refereed) Published
Abstract [en]

Herein, we have studied the potential of lutidinium-based ILs (1-allyl-3,5-dimethylpyridinium chloride [3,5-ADMPy]Cl and 1-allyl-3,4-dimethylpyridinium chloride [3,4-ADMPy]Cl) in the dissolution of cellulose, and their structures were confirmed by 1H and 13C NMR spectra, respectively. [3,5-ADMPy]Cl exhibited the highest capacity in cellulose dissolution. In fact, it dissolved 20 wt% of cellulose within 12 min and 26 wt% of cellulose in 35 min at 118 °C. The crystallinity and morphology of native and regenerated cellulose were characterised by X-ray diffraction (XRD), scanning electron microscopy (SEM) and CP/MAS 13C NMR spectroscopy. These techniques clearly suggest that the crystallinity of cellulose is reduced upon treatment in lutidinium-based ILs. The thermogravimetric analysis (TGA) showed that regenerated cellulose had thermal stability close to that of native cellulose.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019
Keywords
Cellulose dissolution, Ionic Liquids, X-ray diffraction, Cross polymerization/magic angle spinning C NMR, Thermogravimetric analysis, viscosity, scanning electron microscopy
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:umu:diva-154779 (URN)10.1039/C8NJ04698K (DOI)000459581000027 ()
Available from: 2019-01-02 Created: 2019-01-02 Last updated: 2019-03-27Bibliographically approved
Nuri, A., Mansoori, Y., Bezaatpour, A., Shchukarev, A. & Mikkola, J.-P. (2019). Magnetic Mesoporous SBA-15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction. ChemistrySelect, 4(5), 1820-1829
Open this publication in new window or tab >>Magnetic Mesoporous SBA-15 Functionalized with a NHC Pd(II) Complex: An Efficient and Recoverable Nanocatalyst for Hiyama Reaction
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2019 (English)In: ChemistrySelect, ISSN 2365-6549, Vol. 4, no 5, p. 1820-1829Article in journal (Refereed) Published
Abstract [en]

Magnetite nanoparticles (MNPs) were covered by a silica shell and then embedded into mesoporous silica (SBA‐15). Magnetic mesoporous silica (Fe3O4@SiO2‐SBA) was then reacted with 3‐chloropropyltriethoxysilane (CPTS), sodium salt of imidazole and 2‐bromopyridine to give Fe3O4@SiO2‐SBA functionalized with 3‐(pyridin‐2‐yl)‐1H‐imidazol‐3‐ium‐propyl (PIP) as a supported pincer ligand for Pd(II). The functionalized magnetic mesoporous silica were then treated with t‐BuOK at −80 °C in THF and then reacted with [PdCl2(SMe2)2] to give supported Pd(II)‐carbene complex containing C,N‐bidentate ligand. The chloride ions were then exchanged by bromide ions using a NaBr solution of diethylether/acetone mixture. The prepared catalyst was characterized with, FT‐IR, thermo gravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), Brunauer–Emmett–Teller surface area measurement (SBET), energy dispersive X‐ray analysis (EDX) and wide angle X‐ray diffraction spectroscopy (XRD). The prepared magnetic catalyst was effectively used in the coupling reaction of triethoxyphenylsilane with aryl halides (Hiyama reaction) in the presence of a base. The reaction parameters such as solvents, amount of catalyst, base and temperature were optimized. The catalyst was then magnetically decanted, washed, and reused several times.

Keywords
Carbene-pyridine Pd(II) complex, Heterogeneous catalyst, Hiyama reaction, Magnetic mesoporous nanoparticles
National Category
Materials Chemistry Physical Chemistry
Identifiers
urn:nbn:se:umu:diva-156875 (URN)10.1002/slct.201803798 (DOI)000458164500037 ()
Available from: 2019-03-11 Created: 2019-03-11 Last updated: 2019-03-11Bibliographically approved
Shukla, S. K. & Mikkola, J.-P. (2019). Unusual temperature-promoted carbon dioxide capture in deep-eutectic solvents: the synergistic interactions. Chemical Communications, 55, 3939-3942
Open this publication in new window or tab >>Unusual temperature-promoted carbon dioxide capture in deep-eutectic solvents: the synergistic interactions
2019 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 55, p. 3939-3942Article in journal (Refereed) Published
Abstract [en]

A series of novel ethylenediamine(EDA)-based deep-eutectic solvents (DESs) gave rise to unexpectedly large carbon dioxide (CO2) capturing capacity at higher temperatures owing to the “synergetic interaction” between the donor and acceptor moieties.

Place, publisher, year, edition, pages
Cambridge: Royal Society of Chemistry, 2019
National Category
Inorganic Chemistry
Identifiers
urn:nbn:se:umu:diva-157020 (URN)10.1039/C9CC00831D (DOI)
Available from: 2019-03-06 Created: 2019-03-06 Last updated: 2019-04-01Bibliographically approved
Saeid, S., Tolvanen, P., Kumar, N., Eränen, K., Peltonen, J., Peurla, M., . . . Salmi, T. (2018). Advanced oxidation process for the removal of ibuprofen from aqueous solution: a non-catalytic and catalytic ozonation study in a semi-batch reactor. Applied Catalysis B: Environmental, 230, 77-90
Open this publication in new window or tab >>Advanced oxidation process for the removal of ibuprofen from aqueous solution: a non-catalytic and catalytic ozonation study in a semi-batch reactor
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2018 (English)In: Applied Catalysis B: Environmental, ISSN 0926-3373, E-ISSN 1873-3883, Vol. 230, p. 77-90Article in journal (Refereed) Published
Abstract [en]

The Concern on the availability of clean and safe fresh water and the quality of recycled wastewater are important issues, which require a suitable technology to restore the water quality. Pharmaceuticals in waste water are not easily degraded by conventional water treatment technology. Advanced oxidation processes have been applied to eliminate traces of these compounds from aquatic environments. This study was focused on the degradation of ibuprofen (IBU) in aqueous solutions by catalytic and non-catalytic ozonation. Preliminary experiments were conducted to optimize the ozone concentration in water and to investigate other operation parameters. The operation parameters were: temperature, stirring rate, gas flow rate, pH, and use of Spinchem stirrer to reach higher concentrations of dissolved ozone. In general, the initial concentration of IBU was 10 mg/L, and about 93% of IBU was degraded after 4 h of ozonation under optimal conditions. Additional experiments were carried out to investigate the benefit of applying a solid catalyst. H-Beta and Fe-H-Beta type catalysts were immobilized in the Spinchem rotating bed device. The catalytic experiments illustrated a significant improvement in the degradation rate of IBU. The catalysts were characterized by nitrogen adsorption- desorption, scanning electron microscopy, transmission electron microscopy, X-ray powder diffraction and FTIR.

Place, publisher, year, edition, pages
Amsterdam: Elsevier, 2018
Keywords
Ibuprofen, Ozone, Advanced oxidation processes (AOPs), Heterogeneous catalyst
National Category
Analytical Chemistry
Identifiers
urn:nbn:se:umu:diva-145680 (URN)10.1016/j.apcatb.2018.02.021 (DOI)000429500100009 ()
Available from: 2018-03-14 Created: 2018-03-14 Last updated: 2018-06-09Bibliographically approved
Konwar, L. J., Samikannu, A., Mäki-Arvela, P. & Mikkola, J.-P. (2018). Efficient C-C coupling of bio-based furanics and carbonyl compounds to liquid hydrocarbon precursors over lignosulfonate derived acidic carbocatalysts. Catalysis Science & Technology, 8(9), 2449-2459
Open this publication in new window or tab >>Efficient C-C coupling of bio-based furanics and carbonyl compounds to liquid hydrocarbon precursors over lignosulfonate derived acidic carbocatalysts
2018 (English)In: Catalysis Science & Technology, ISSN 2044-4753, E-ISSN 2044-4761, Vol. 8, no 9, p. 2449-2459Article in journal (Refereed) Published
Abstract [en]

This paper demonstrates the catalytic potential of novel Na-lignosulfonate (LS) derived meso/macroporous solid protonic acids upon C–C coupling of bio-based furanics and carbonyl compounds. The materials demonstrated catalytic activity for solventless hydroxyalkylation/alkylation (HAA) of 2-methylfuran with furfural, acetone, butanal, cyclohexanone, levulinic acid and α-angelica lactone under mild reaction conditions (50–60 °C) producing branched-chain C12–C16 hydrocarbon precursors in yields approaching 96%. Moreover, the carbon materials exhibiting high total acidity (6–6.4 mmol g−1) outperformed sulfonic acid resins (Amberlyst®70, Amberlite®IR120 and LS resin), zeolites and liquid acids (p-toluenesulfonic acid, acetic acid and phenol). In fact, the most active carbocatalyst (60LS40PS350H+) exhibited the same turnover frequency as p-toluenesulfonic acid (186 h−1) upon furfural conversion but with an improved HAA product yield (up to 88%) and reusability, maintaining 98% of its original activity up to seven reaction cycles. The observed catalytic activity and operational stability of the LS derived acidic carbocatalysts were attributed to the strongly Brønsted acidic –SO3H groups covalently incorporated into their structural carbon framework and the promotional effects of hydrophilic surface functional groups (–COOH and –OH) favoring adsorption of oxygenated reactant molecules.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-146304 (URN)10.1039/C7CY02601C (DOI)000433163900021 ()
Available from: 2018-04-04 Created: 2018-04-04 Last updated: 2018-06-20Bibliographically approved
Aguilera, A. F., Tolvanen, P., Heredia, S., Muñoz, M. G., Samson, T., Oger, A., . . . Salmi, T. (2018). Epoxidation of fatty acids and vegetable oils assisted by microwaves catalyzed by a cation exchange resin. Industrial & Engineering Chemistry Research, 57(11), 3876-3886
Open this publication in new window or tab >>Epoxidation of fatty acids and vegetable oils assisted by microwaves catalyzed by a cation exchange resin
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2018 (English)In: Industrial & Engineering Chemistry Research, ISSN 0888-5885, E-ISSN 1520-5045, Vol. 57, no 11, p. 3876-3886Article in journal (Refereed) Published
Abstract [en]

Epoxidation of oleic acid and cottonseed oil was conducted in a semibatch reactor with in-situ-formed percarboxylic acid (peracetic acid or perpropionic acid), using hydrogen peroxide as an oxidizing agent and carboxylic acid (acetic acid or propionic acid) as oxygen carriers. Amberlite IR-120 was implemented as the catalyst. The system was comprised of a loop reactor, where the mixture was pumped through a single-mode cavity in which microwave irradiation was introduced. A heat exchanger was integrated into the system to replace microwave heating, to compare the results obtained via microwave heating versus conventional heating. The catalyst loading effect was studied, as well as the influence of microwave irradiation and the implementation of the SpinChem rotating bed reactor (RBR), in hopes of decreasing the influence of the internal mass transfer. The application of microwave irradiation results in an improvement of the reaction yield in the absence of a catalyst.

Place, publisher, year, edition, pages
Washington: American Chemical Society (ACS), 2018
Keywords
soybean oil, reaction system, reactor system, peracetic acid, oleic acid, seed oil, kinetics, polyols
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-145683 (URN)10.1021/acs.iecr.7b05293 (DOI)000428356100008 ()
Available from: 2018-03-14 Created: 2018-03-14 Last updated: 2018-06-09Bibliographically approved
Khokarale, S. G. & Mikkola, J.-P. (2018). Hydrogen sulfide gas capture by organic superbase 1,8-diazabicyclo-[5.4.0]-undec-7-ene through salt formation: salt synthesis, characterization and application for CO2 capture. RSC Advances, 8(33), 18531-18541
Open this publication in new window or tab >>Hydrogen sulfide gas capture by organic superbase 1,8-diazabicyclo-[5.4.0]-undec-7-ene through salt formation: salt synthesis, characterization and application for CO2 capture
2018 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 8, no 33, p. 18531-18541Article in journal (Refereed) Published
Abstract [en]

Hydrogen sulfide (H2S) is a toxic and environment polluting gas like other acid gases and hence its capture and sequestration is equally important before release into the atmosphere. In this regard, solvent-based processes involving aqueous tertiary amine systems were extensively studied and used. Herein, in line with an analogous pathway, we report capture of H2S gas in the form of its salt with an organic superbase such as 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and the obtained salt was thoroughly studied. Spectroscopic analyses such as NMR and FTIR analyses confirmed that the H2S molecule formed an ionic solid adduct with DBU through protonation of its sp2-hybridized N atom. The stability of formed [DBUH][SH] salt in aqueous solution as well as under thermal treatment was also studied and monitored by NMR and thermogravimetric analysis (TGA), respectively. In aqueous medium, compared to DBU, the [DBUH][SH] salt exhibited long term stability without decomposition whereas under thermal treatment both DBU and its salt with H2S turned out to be thermally unstable where salt showed a volatile nature like a sublimized solid. Dissolution feasibility of [DBUH][SH] salt was also compared with DBU in polar as well as non-polar solvents and even though the [DBUH][SH] salt had an ionic nature, like DBU, it was also found soluble in various polar and non-polar solvents. Considering the stability of [DBUH][SH] salt in aqueous medium, its aqueous solution was further explored as a solvent media for CO2 capture where the influence of process parameters such as the influence of concentration of water in the solvent and CO2 flow rate was studied. Most importantly, here we demonstrated the synthesis of [DBUH][SH] salt for easy capture of H2S gas following reaction with DBU under ambient reaction conditions.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018
National Category
Physical Chemistry
Identifiers
urn:nbn:se:umu:diva-147956 (URN)10.1039/C8RA02993H (DOI)000433428300042000433428300042 ()
Funder
Swedish Research Council, 2016-04090Bio4EnergyThe Kempe FoundationsKnut and Alice Wallenberg Foundation
Available from: 2018-05-23 Created: 2018-05-23 Last updated: 2018-11-06Bibliographically approved
Verziu, M., Tirsoaga, A., Cojocaru, B., Bucur, C., Tudora, B., Richel, A., . . . Mikkola, J. P. (2018). Hydrogenolysis of lignin over Ru-based catalysts: the role of the ruthenium in a lignin fragmentation process. Molecular Catalysis, 450, 65-76
Open this publication in new window or tab >>Hydrogenolysis of lignin over Ru-based catalysts: the role of the ruthenium in a lignin fragmentation process
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2018 (English)In: Molecular Catalysis, ISSN 2468-8231, Vol. 450, p. 65-76Article in journal (Refereed) Published
Abstract [en]

The catalytic performances of two different classes of catalysts containing nickel or/and ruthenium as the active sites were studied in the depolymerisation of lignin isolated from Miscanthus×giganteus. The catalysts were prepared either by coprecipitation (ie, (RuNiMgAlO)x, (RuNiAlO)x, (NiAlO)x, (NiMgAlO)x) or by wet impregnation (ie, Ru/Al2O3) and characterized by nitrogen physisorption (BET), XRD, XPS, NH3-TPD, Raman and H2-TPR techniques. The experimental results indicate that the presence of ruthenium led to dimers as dominant products.

Place, publisher, year, edition, pages
Elsevier, 2018
Keywords
lignin, hydrogenolysis, heterogeneous catalysts, Ru-based catalysts
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-146057 (URN)10.1016/j.mcat.2018.03.004 (DOI)000431158400008 ()
Available from: 2018-03-28 Created: 2018-03-28 Last updated: 2018-06-09Bibliographically approved
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