Tetra-methylammonium bromide (Loba Chemie, 98%), 1-methylimidazole (C4H6N2) (Alfa Aesar, 99.0%), 1,2-dimethylimidazole (Sigma Aldrich, 98%), Bromoethane (C2H5Br) (99.0%), n-Butyl Bromide (C4H9Br) (96.0%), n-Hexyl Bromide (C6H13Br) (99.0%), Octyl Bromide (C8H17Br) (98.5%) of Himedia brand were used. Ethyl Acetate (99.5%), Acetonitrile (99.5%), Dichloromethane (99.5%) were purchased from Loba Chemie and Silver Nitrate from Fisher Scientific brands were used. 1-ethyl-3-methylimidazolium bromide [Emim][Br], 1-ethyl-2,3-dimethylimidazolium bromide [Edmim][Br], 1-butyl-3-methylimidazolium bromide [Bmim][Br], 1-hexyl-3-methylimidazolium bromide [Hmim][Br] and 1-octyl-3-methylimidazolium bromide [Omim][Br] were prepared by modifying the previously reported methods (Ghosh and Mudring, 2016 (link); Kumar et al., 2017 (link)). Synthesis procedure of the above mentioned ionic liquids (ILs) in detail is followed as:
1 2 dimethylimidazole
Manufactured by Merck Group
Sourced in Germany
1,2-dimethylimidazole is a chemical compound used as a laboratory reagent. It is a colorless, crystalline solid with a melting point of 123-126°C. The compound is soluble in organic solvents.
Automatically generated - may contain errors
Lab products found in correlation
Lauric acid, by Merck Group (2 mentions)
Methanol, by Merck Group (2 mentions)
Silver nitrate, by Thermo Fisher Scientific (1 mentions)
Bromoethane, by Merck Group (1 mentions)
Acetonitrile, by Loba Chemie (1 mentions)
Dichloromethane, by Loba Chemie (1 mentions)
Ethyl acetate, by Loba Chemie (1 mentions)
1 methylimidazole, by Thermo Fisher Scientific (1 mentions)
Polylactic acid pla, by NatureWorks (1 mentions)
Diethyl ether, by Biosolve (1 mentions)
1 bromohexadecane, by Merck Group (1 mentions)
Acetonitrile, by Biosolve (1 mentions)
Ethanol, by Biosolve (1 mentions)
Sodium sulphate, by Merck Group (1 mentions)
Ethylene carbonate, by Merck Group (1 mentions)
Dibutyltin oxide, by Merck Group (1 mentions)
Trimethylolpropane triglycidyl ether, by Merck Group (1 mentions)
2 aminoethanol, by Merck Group (1 mentions)
Amine terminated ether, by Merck Group (1 mentions)
Ethanol etoh, by Avantor (1 mentions)
14 protocols using 1 2 dimethylimidazole
1
Synthesis of Imidazolium-based Ionic Liquids
2
ENR-PLA Biocomposite Reinforcement
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The subject of the study, epoxidized natural rubber (ENR) (Epoxyprene ENR-50; 50 mol% epoxidation), was obtained from Kumpulan Guthrie Berhad (Kuala Lumpur, Malaysia). Poly(lactic acid) (PLA) was provided by Nature Works (Minnetonka, Minnesota, USA). Cellulose fibers (CF) employed in this research were the Arbocel UFC100 Ultrafine Cellulose for Paper and Board Coating (UFC100) from J. Rettenmaier & Soehne (Rosenberg, Germany). It was in powder form (density: 1.3 g/cm3, average fiber length: 6–12 µm, pH: 5.0–7.5). Flax fibers (FF) employed in this research were supplied by Łukasiewicz Research Network—Institute of Biopolymers and Chemical Fibers (Lodz, Poland). Fibers were comminuted and composed of lignin, hemicellulose, and cellulose in an unknown ratio. Montmorillonite (MMT) modified nanoclay was purchased from Sigma–Aldrich (Darmstadt, Germany). It contained 25–30 wt% of octadecylamine grafted onto the surface. MMT particle size was approximately 20 µm. Lauric acid (97% purity), 1,2-dimethylimidazole (highest available purity), obtained from Sigma–Aldrich (Darmstadt, Germany), and elastin hydrolysate, purchased from Proteina (Lodz, Poland), were used as a crosslinking system.
3
Synthesis of Cationic Surfactant C16H33-[1,2-dimethyl-3-imidazolium]
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In total,
0.013 mol of 1-bromohexadecane (Sigma-Aldrich, 98.0%) and 0.016 mol
of 1,2-dimethylimidazole (Sigma-Aldrich, 97.0%) were dissolved in
a 50 mL mixture of ethanol (Biosolve, 99.9%) and acetonitrile (Biosolve,
99.9%) (1:5 molar ratio) and heated at 70 °C for 16 h under nitrogen
atmosphere. After evaporation of the solvents and addition of diethyl
ether (Biosolve, 99.5%), a white powder precipitated out of solution.
This solid product was filtered and dried in a vacuum oven at 50 °C
for 12 h. The purity of the organic surfactant C16H33-[1,2-dimethyl-3-imidazolium] was analyzed by 1H, 13C, gHSQC, and gCOSY NMR after dissolution in CDCl3 (Figures S1–S4 ). The product
yield was 75%.
0.013 mol of 1-bromohexadecane (Sigma-Aldrich, 98.0%) and 0.016 mol
of 1,2-dimethylimidazole (Sigma-Aldrich, 97.0%) were dissolved in
a 50 mL mixture of ethanol (Biosolve, 99.9%) and acetonitrile (Biosolve,
99.9%) (1:5 molar ratio) and heated at 70 °C for 16 h under nitrogen
atmosphere. After evaporation of the solvents and addition of diethyl
ether (Biosolve, 99.5%), a white powder precipitated out of solution.
This solid product was filtered and dried in a vacuum oven at 50 °C
for 12 h. The purity of the organic surfactant C16H33-[1,2-dimethyl-3-imidazolium] was analyzed by 1H, 13C, gHSQC, and gCOSY NMR after dissolution in CDCl3 (
yield was 75%.
4
Nanocomposite Synthesis via Zinc Acetate
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First, 0.7 g of nanoparticles that were synthesized in the previous step were added drop by drop to the zinc acetate solution (Sigma-Aldrich Corporation, MO). Then, it was stirred magnetically in 10 ml of methanol for 20 min, after the complete suspension, 0.5 gr of 1,2 dimethyl imidazole (Sigma-Aldrich Corporation, MO) was added drop by drop to the suspension. After stirring for 15 min, the synthesized nanocomposites were washed several times with methanol and PBS (Sigma-Aldrich Corporation, MO). Then, dried in an oven at 100 °C for 12 h and collected for characterization.
5
Synthesis of Polyurethane Coatings from Vanillin and Ethylene Carbonate
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Vanillin (VL) (99%), ethylene carbonate (EC) (98%), potassium carbonate (K2CO3, 99%), sodium sulphate (Na2SO4), dibutyltin oxide (DBTO) (>98%), 2‐aminoethanol (>99%), trimethylolpropane tris [poly (propylene glycol), amine terminated] ether (Jefm) (average Mn of 440 g mol−1), trimethylolpropane triglycidyl ether (TMPTGE), 1,2‐dimethylimidazole, and dibutyltin dilaurate (DBTDL) (>95%) were purchased from Sigma‐Aldrich. N,N‐dimethylformamide (DMF, ACS, Reag. Ph. Eur.), ethyl acetate (EtOAc, ACS, Reag. Ph. Eur.), and ethanol (EtOH) were purchased from VWR Chemicals. All chemicals and reagents were used as received.
6
Synthesis of Organometallic Complexes
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Potassium tetrachloroplatinate, K2PtCl4 (98%, Sigma Aldrich, Saint Louis, MO, USA), potassium hexachloroplatinate, K2PtCl6 (98%, Sigma Aldrich), bis(triphenylphosphine)platinum chloride, Pt(PPh3)2Cl2 (98%, Sigma Aldrich), tetrakis(triphenylphosphine)platinum(0), Pt(PPh3)4 (98%, Sigma Aldrich), tris(triphenylphosphine)rhodium (I) chloride, [RhCl(PPh3)3] also known as Wilkinson’s catalyst (98%, Sigma Aldrich), Karstedt catalyst—platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (2.2% solution in xylene, Sigma Aldrich), pyridine (Sigma Aldrich), 2-methylimidazole (Sigma Aldrich), 1,2-dimethylimidazole (Sigma Aldrich), tributyltetradecylphosphonium chloride [P44414][Cl] (IoLiTec—Ionic Liquids Technologies GmbH, Helibronn, Germany), 1-butyl-2,3-dimethylimidazolium chloride [BMMIM][Cl] (IoLiTec), triethylsulfonium bis(trifluoromethylsulfonyl)imide [S222][NTf2] (4 ) (IoLiTec), bis(trifluoromethylsulfonyl)imide lithium salt, LiNTf2 (IoLiTec) were used as received.
7
Anhydrous FeCl3-Mediated Methylation
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Anhydrous FeCl3 (99.9%, Aldrich), 1,2-dimethylimidazole (98%, Sigma-Aldrich), acetonitrile (HPLC grade, Vetec), methyl iodide (98%, Acros) and other chemicals were purchased from commercial sources and used without any further purification. All manipulations were performed in air atmosphere, except otherwise stated in the text.
8
Synthesis and Characterization of Imidazolium-based Ionic Liquids
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All solutions and samples were
prepared by using deionized water with a resistivity of 18.2 Ω
cm–1 from a Millipore Milli-Q water purification
system (Millipore). Gluten from wheat was purchase from Sigma-Aldrich.
1,2-Dimethyl imidazole (98%), 1-fuloro pentane, methanol (99%), propanol
(99%), pentanol (99%), heptanol (98%), nonanol (98%), and dodecanol
(98%) were purchased from ACOS; dichloromethane (99%) was purchased
from Tedia (98% purity); acetonitrile (99%), ether (99%), fetal bovine
serum (FBS), Gluten from wheat, methanesulfonic acid (99), methane
sulfonic chloride (99%), thionyl chloride (98%), silver nitride (95%),
silver dihydrogen phosphate (99%), and silver bisulfate (99%) were
purchased from Sigma-Aldrich; antigliadin mouse IgG 2F (1 mg/mL) was
purchased from Antaimmu; antigliadin human IgA 3B7 (1 mg/mL) and a
gliadin solution (1 mg/mL) were purchased from Leadgene; HRP was present
in the MagicLink HRP antibody conjugation kit; 3,3′,5,5′-tetramethylbenzidine
(TMB) and hydrogen peroxide (H2O2) reagent were
purchased from TCI; and the Wheat/Gluten (Gliadin) ELISA kit was purchased
from Crystal Chem (AOAC no. 011804). DEMD and XTT reagents were purchased
from Thermo Fisher.
IL synthesis is given in theSupporting Information, and the product yield
is given inTable S1 .
prepared by using deionized water with a resistivity of 18.2 Ω
cm–1 from a Millipore Milli-Q water purification
system (Millipore). Gluten from wheat was purchase from Sigma-Aldrich.
1,2-Dimethyl imidazole (98%), 1-fuloro pentane, methanol (99%), propanol
(99%), pentanol (99%), heptanol (98%), nonanol (98%), and dodecanol
(98%) were purchased from ACOS; dichloromethane (99%) was purchased
from Tedia (98% purity); acetonitrile (99%), ether (99%), fetal bovine
serum (FBS), Gluten from wheat, methanesulfonic acid (99), methane
sulfonic chloride (99%), thionyl chloride (98%), silver nitride (95%),
silver dihydrogen phosphate (99%), and silver bisulfate (99%) were
purchased from Sigma-Aldrich; antigliadin mouse IgG 2F (1 mg/mL) was
purchased from Antaimmu; antigliadin human IgA 3B7 (1 mg/mL) and a
gliadin solution (1 mg/mL) were purchased from Leadgene; HRP was present
in the MagicLink HRP antibody conjugation kit; 3,3′,5,5′-tetramethylbenzidine
(TMB) and hydrogen peroxide (H2O2) reagent were
purchased from TCI; and the Wheat/Gluten (Gliadin) ELISA kit was purchased
from Crystal Chem (AOAC no. 011804). DEMD and XTT reagents were purchased
from Thermo Fisher.
IL synthesis is given in the
is given in
9
Synthesis and Characterization of ILs
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Materials TMOP and TEOP have been synthesized using phosphorus(V) oxychloride (99% purity, Sigma Aldrich) and respective alcohol triethylene glycol monomethyl ether (95% purity, Sigma Aldrich) and di(ethylene glycol) ethyl ether (99% purity, Sigma Aldrich). 1-Methylpyrrolidine (98% purity, Sigma Aldrich) 1,2dimethylimidazole (99% purity, Sigma Aldrich), 1-methylimidazole (98% purity, Sigma Aldrich), sodium sulfate (99% purity, Sigma Aldrich), ethyl acetate (99.5% purity, Sigma Aldrich) and hexane (99% purity, Sigma Aldrich) were used without further purification. All the synthesized ILs were kept in a vacuum oven at 90 1C for at least 3 days until the water content was less than 100 ppm (Table S4, ESI †), as determined by the Karl-Fischer titration using a 917 coulometer (Metrohm) placed inside a glovebox with water and oxygen contents less than 1 ppm. Multi-walled carbon nanotubes (Sigma Aldrich, 95% carbon, O.D.  L 6-9 nm  5 mm), activated charcoal (Sigma Aldrich, 100 mesh size), polyvinyl alcohol (Merck, M W 72 000) and glass microfiber filters (Whatman s ) were used as received.
10
Mutagenicity Assay Chemical Reagents
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Acetoin ≥95%, dimethyl carbonate 99%, p-toluenesulphonic acid monohydrate 98.5%, 4-methoxyacetophenone 99%, anhydrous anisole 99.7%, acetic anhydride ≥99%, anhydrous acetonitrile 99.8%, anhydrous cyclohexane 99.5%, anhydrous diethyl ether ≥99%, anhydrous propylene carbonate 99.7%, iron(iii ) chloride 97%, anhydrous ethyl acetate 99.8%, anhydrous magnesium sulphate 99.5%, Nile red ≥98%, 4-nitroaniline ≥99%, 4-nitroanisole analytical standard, 4-nitrophenol spectrophotometric grade, 1,2-dimethylimidazole 98%, 1-bromodecane 98%, methanol 99.9%, dichloromethane 99.8%, acetone 99.9%, chloroform-d (CDCl3, 99.8% D), chloroform 99.9%, dimethyl sulfoxide 99.9% were purchased from Sigma-Aldrich. Ames MPF 98/100 kits, 2-nitrofluorene and 4-nitroquinoline-N-oxide were purchased from Xenometrix. TA98 and TA100 were stored at −70 °C. QUANTOFIX® Peroxide 100 was purchased from Macherey-Nagel. N,N-Diethyl-4-nitroaniline was purchased from VWR.
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