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Mikkola, Jyri-Pekka
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Publications (10 of 252) Show all publications
Mohammadi, M., Shafiei, M., Abdolmaleki, A., Karimi, K., Mikkola, J.-P. & Larsson, C. (2019). A morpholinium ionic liquid for rice straw pretreatment to enhance ethanol production. Industrial crops and products (Print), 139, Article ID 111494.
Open this publication in new window or tab >>A morpholinium ionic liquid for rice straw pretreatment to enhance ethanol production
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2019 (English)In: Industrial crops and products (Print), ISSN 0926-6690, E-ISSN 1872-633X, Vol. 139, article id 111494Article in journal (Refereed) Published
Abstract [en]

Rice straw was successfully pretreated with a novel and inexpensive morpholinium ionic liquid, 1-H-3-methylmorpholinium chloride ([HMMorph][Cl]). The influence of water (30, 40, 50% w/w) and dimethyl sulfoxide (DMSO) (10, 30% w/w), as co-solvents, pretreatment time (2, 3, 5 h), temperature (90, 105, 120 °C), solid loading (5, 6.7, 10% w/w), and straw particle size (<0.177, 0.177–0.841 mm, and 0.841–2 mm) were investigated for maximum ethanol production. The best results were obtained in 50% water, at 120 °C and 5% (w/w) solid loading for 5 h from 0.177 – 0.841 mm straw particles. The hydrolysis yield was increased from 33.2% to 70.1%, while ethanol production yield was improved from 21.9% to 64% of the theoretical maximum. The performance of the IL was comparable to 1-ethyl-3-methylimidazolium acetate. Simple synthesis process and dilute solution required for the pretreatment with [HMMorph][Cl] offers cost reductions in the use of ILs in biofuel production.

Place, publisher, year, edition, pages
Elsevier, 2019
Keywords
Ethanol, Hydrolysis, Morpholinium ionic liquid, Rice straw
National Category
Bioenergy
Identifiers
urn:nbn:se:umu:diva-161787 (URN)10.1016/j.indcrop.2019.111494 (DOI)2-s2.0-85067492224 (Scopus ID)
Projects
Bio4Energy
Available from: 2019-08-05 Created: 2019-08-05 Last updated: 2019-08-29Bibliographically approved
Jogi, R., Mäki-Arvela, P., Virtanen, P., Kumar, N., Hemming, J., Smeds, A., . . . Mikkola, J.-P. (2019). Biocrude production through hydro‐liquefaction of wood biomass in supercritical ethanol using iron silica and iron Beta zeolite catalysts. Journal of chemical technology and biotechnology (1986)
Open this publication in new window or tab >>Biocrude production through hydro‐liquefaction of wood biomass in supercritical ethanol using iron silica and iron Beta zeolite catalysts
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2019 (English)In: Journal of chemical technology and biotechnology (1986), ISSN 0268-2575, E-ISSN 1097-4660Article in journal (Refereed) Epub ahead of print
Abstract [en]

BACKGROUND: In the production of biofuels from lignocellulosic material, biocrude plays a key role. The present work deals with the biocrude production through hydrothermal liquefaction (HTL) of birch wood in supercritical ethanol over 5 wt. % Fe‐H‐Beta‐150 (SiO2 to Al2O3 ratio of 150) or 5 wt. % Fe‐SiO2 catalyst.

RESULTS: The liquid and solid products were characterized with various analytical techniques such as GC‐MS, GC‐FID, SEC, ICP‐MS, p‐XRD, SEM, and solid‐state 13C MAS NMR respectively. The results revealed that 5 wt. % Fe‐H‐Beta‐150, a strongly Brønsted acidic catalyst, enhanced the biocrude formation when compared with a non‐acidic 5 wt. % Fe‐SiO2 catalyst. Hemicellulose and lignin degradation occurred resulting in formation of mainly sugars, acids‐esters and phenolic compounds in liquid phase. The gaseous atmosphere of hydrogen also enhanced the degradation of biomass. The biocrude yield from birch was 25 wt. % over 5 wt. % Fe‐H‐Beta‐150. The Brønsted acidic catalyst gave higher dissolution efficiency and its clear catalytic effect was observed in comparison to non‐acidic 5 wt. % Fe‐SiO2. The degradation level of lignin in presence of 5 wt. % Fe‐H‐Beta‐150 was high 68 wt. % aromatic products were formed, while only 38 wt. % was obtained with 5 wt. % Fe‐SiO2.

CONCLUSIONS: Hydrogen atmosphere enhances the fractionation of birch wood when compared to argon atmosphere. 5 wt. % Fe‐H‐Beta‐150 catalyst enhanced very strongly the degradation of hemicellulose and lignin in biomass to sugars and acid‐esters as well as phenolic compounds, respectively compared to the non‐acidic 5 wt. % Fe‐SiO2 catalyst.

Place, publisher, year, edition, pages
John Wiley & Sons, Ltd, 2019
Keywords
hydrothermal liquefaction (HTL), birch, supercritical ethanol, hydrogen atmosphere, iron supported zeolite
National Category
Chemical Process Engineering Organic Chemistry Polymer Chemistry
Identifiers
urn:nbn:se:umu:diva-162429 (URN)10.1002/jctb.6181 (DOI)
Projects
Bio4Energy
Available from: 2019-08-20 Created: 2019-08-20 Last updated: 2019-08-29
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, 21, 2138-2147
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 1463-9270, Vol. 21, p. 2138-2147Article in journal (Refereed) Published
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)000465398000029 ()
Projects
Bio4Energy
Available from: 2019-03-22 Created: 2019-03-22 Last updated: 2019-08-29Bibliographically approved
Mohammadi, M., Shafiei, M., Karimi, K., Abdolmaleki, A., Mikkola, J.-P. & Larsson, C. (2019). Improvement of ethanol production from birch and spruce pretreated with 1-H-3-methylmorpholinium chloride. Electronic Journal of Biotechnology, 41, 95-99
Open this publication in new window or tab >>Improvement of ethanol production from birch and spruce pretreated with 1-H-3-methylmorpholinium chloride
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2019 (English)In: Electronic Journal of Biotechnology, ISSN 0717-3458, E-ISSN 0717-3458, Vol. 41, p. 95-99Article in journal (Refereed) Published
Abstract [en]

Background: Pretreatment is the critically important step for the production of ethanol from lignocelluloses. In this study, hardwood birch (Betula pendula) and softwood spruce (Norway spruce) woods were pretreated with a newly synthesized morpholinium ionic liquid, 1-H-3-methylmorpholinium chloride ([HMMorph][Cl]), followed by enzymatic hydrolysis and fermentation to ethanol.

Results: [HMMorph][Cl] was synthesized using inexpensive raw materials, i.e., hydrochloric acid and N-methyl morpholine, following a simple process. The influence of pretreatment time (2, 3, 5, and 8 h) and temperature (120 and 140°C) in terms of hydrolysis efficiency was investigated. Glucose yields from enzymatic hydrolysis were improved from 13.7% to 45.7% and 12.9% to 51.8% after pretreatment of birch and spruce woods, respectively, under optimum pretreatment conditions (i.e., at 140°C for 3 h) as compared to those from pristine woods. Moreover, the yields of ethanol production from birch and spruce were increased to 34.8% and 44.2%, respectively, while the yields were negligible for untreated woods.

Conclusions: This study demonstrated the ability of [HMMorph][Cl] as an inexpensive agent to pretreat both softwood and hardwood.

Place, publisher, year, edition, pages
Elsevier, 2019
Keywords
Betula, Biofuels, Cellulase, Cellulose, Ethanol, Hydrolysis, Ionic liquid, Lignin, Lignocellulose, Morpholinium ionic liquid, Pretreatment
National Category
Chemical Process Engineering
Identifiers
urn:nbn:se:umu:diva-162903 (URN)10.1016/j.ejbt.2019.07.004 (DOI)
Projects
Bio4Energy
Available from: 2019-08-30 Created: 2019-08-30 Last updated: 2019-09-05Bibliographically approved
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 ()
Projects
Bio4Energy
Available from: 2019-01-02 Created: 2019-01-02 Last updated: 2019-08-29Bibliographically 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 ()
Projects
Bio4Energy
Available from: 2019-03-11 Created: 2019-03-11 Last updated: 2019-08-30Bibliographically approved
Nuri, A., Vucetic, N., Smatt, J.-H., Mansoori, Y., Mikkola, J.-P. & Murzin, D. Y. (2019). Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction. Catalysis Letters, 149(7), 1941-1951
Open this publication in new window or tab >>Pd Supported IRMOF-3: Heterogeneous, Efficient and Reusable Catalyst for Heck Reaction
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2019 (English)In: Catalysis Letters, ISSN 1011-372X, E-ISSN 1572-879X, Vol. 149, no 7, p. 1941-1951Article in journal (Refereed) Published
Abstract [en]

IRMOF-3 with a high surface area prepared by a hydrothermal method was used for deposition of Pd(OAc)(2) on IRMOF-3 particles. The final catalyst was characterized with FT-IR, nitrogen physisorption, thermogravimetry, scanning electron microscopy, transmission electron microscopy combined with energy dispersive X-ray analysis, wide angle X-ray diffraction spectroscopy and X-ray photoelectron spectroscopy. The prepared porous catalyst was effectively used in the Heck coupling reaction in the presence of an organic base. The reaction parameters such as the type of base, amounts of catalyst and solvents, temperature were optimized. The catalyst was then easily separated, washed, and reused 4 times without significant losses of catalytic activity. [GRAPHICS] .

Place, publisher, year, edition, pages
Springer, 2019
Keywords
Metal-organic-frameworks, IRMOF-3-Pd, Heck reaction
National Category
Physical Chemistry
Identifiers
urn:nbn:se:umu:diva-159835 (URN)10.1007/s10562-019-02756-0 (DOI)000468172400020 ()
Projects
Bio4Energy
Available from: 2019-06-11 Created: 2019-06-11 Last updated: 2019-08-30Bibliographically approved
Vucetic, N., Virtanen, P., Nuri, A., Mattsson, I., Aho, A., Mikkola, J.-P. & Salmi, T. (2019). Preparation and characterization of a new bis-layered supported ionic liquid catalyst (SILCA) with an unprecedented activity in the Heck reaction. Journal of Catalysis, 371, 35-46
Open this publication in new window or tab >>Preparation and characterization of a new bis-layered supported ionic liquid catalyst (SILCA) with an unprecedented activity in the Heck reaction
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2019 (English)In: Journal of Catalysis, ISSN 0021-9517, E-ISSN 1090-2694, Vol. 371, p. 35-46Article in journal (Refereed) Published
Abstract [en]

A new bis-layered supported ionic liquid catalyst (SILCA) loaded with palladium was designed and successfully applied for the Heck reaction of iodobenzene and methyl acrylate. The silica modified catalyst consisting of the first ionic liquid layer - covalently anchored imidazolium bromide - on which the second layer, made of pyridine-carboxylic acid balanced with tetramethylguanidinium cation was attached, resulted in a catalyst with high activity. High turnover frequencies of 22,000 h(-1) were achieved in reactions with a low palladium loading as 0.009 mol %. Lower TOFs, indicating on palladium dimerization was detected when higher amounts were used. The TMG cation had a purpose to recapture and stabilize the Pd nanoparticles thus followed a release and catch mechanism. In order to get a full understanding of the catalyst structure and behaviour, the catalyst was characterized by means of nitrogen physisorption, thermal gravimetric analysis, infrared spectroscopy, scanning electron and transmission electron microscopes, solid-state NMR, X-ray photoelectron spectroscopy and inductively coupled plasma spectroscopy. The catalyst preserved good activity in five cycles.

Place, publisher, year, edition, pages
Elsevier, 2019
Keywords
Heck reaction, Supported ionic liquid catalyst, Palladium, Turn-over frequency, Catalyst characterization
National Category
Physical Chemistry
Identifiers
urn:nbn:se:umu:diva-159414 (URN)10.1016/j.jcat.2019.01.029 (DOI)000466251300005 ()
Projects
Bio4Energy
Available from: 2019-05-29 Created: 2019-05-29 Last updated: 2019-08-30Bibliographically approved
Mukesh, C., Khokarale, S. G., Virtanen, P. & Mikkola, J.-P. (2019). Rapid desorption of CO2 from deep eutectic solvents based on polyamines at lower temperatures: an alternative technology with industrial potential. Sustainable Energy & Fuels, 3(8), 2125-2134
Open this publication in new window or tab >>Rapid desorption of CO2 from deep eutectic solvents based on polyamines at lower temperatures: an alternative technology with industrial potential
2019 (English)In: Sustainable Energy & Fuels, ISSN 2398-4902, Vol. 3, no 8, p. 2125-2134Article in journal (Refereed) Published
Abstract [en]

Herein we developed a new family of polyamine-based deep eutectic solvents (DESs) dedicated to reduce the energy consumption, avoiding the formation of hazardous molecules, aiming at low solvent losses and robust desorption efficiency for carbon dioxide (CO 2) capture technology. The strategy developed for economical, thermally stable and low viscous absorbents for CO 2 capture by functionalized neoteric media of azolide anion and secondary amine is presented. The prepared anion functionalized ionic liquids (ILs) and the derived DESs with ethylene glycol (EG) have a low viscosity which promotes high uptake of CO 2 (17-22% w/w) at 298.15 K and 1 atm. The absorption capacity of DESs was determined by a gravimetric technique. 13 C NMR was used for examine the desorption efficiency (DE) of CO 2. It was found that rapid desorption of CO 2 in TEPA polyamine based DESs occurs compared to monoethanolamine at 80 °C. However, the desorption rate of CO 2 was observed to be higher at higher temperatures and, as a result, under nitrogen flow complete desorption of CO 2 took place at 100 and 110 °C after 30 and 20 minutes, respectively. Consequently, comparative regeneration of CO 2 was studied in the absence of nitrogen flow at different temperatures. Excellent reversible uptake of CO 2 was observed without significant loss of absorption capacity under four consecutive cycles at 100 °C. The chemisorption of CO 2 was verified by 13 C NMR, 2D-NMR and FT-IR spectroscopy. The solvent loss study demonstrated the low volatility of polyamines based DESs at 100 °C and 120 °C after 50 hrs. The proposed DESs are thermally stable, cheap and give rise to negligible amounts of hazardous degradation components. Further, they exhibit low solvent losses, low viscosities and rapid CO 2 desorption capability. Therefore they are promising candidates when aiming at improving amine based conventional CO 2 capture technology.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2019
National Category
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-161789 (URN)10.1039/C9SE00112C (DOI)000476912900021 ()2-s2.0-85069772826 (Scopus ID)
Projects
Bio4Energy
Available from: 2019-08-05 Created: 2019-08-05 Last updated: 2019-08-30Bibliographically approved
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