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14 protocols using pyridine

1

Synthesis of Gold Nanoparticles with PVP

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Polyvinylpyrrolidone (PVP) with a molecular weight of 40,000 g/mol were purchased from Sigma-Aldrich (St. Louis, MO, USA), as well as gold(III) chloride trihydrate, sodium citrate, (3-aminopropyl)triethoxysilane (APTES) and sodium silicate. Pyridine, sodium borohydride, hydrochloric acid, N,N-dimethylformamide (DMF) and methanol were purchased from Kanto Chemical Co. Most of the chemicals are in high grade (>99.5%), while sodium silicate solution and sodium borohydride were at the grade of 27% and 98%, respectively. High quality 70% HClO4 (Suprapur grade) for electrochemical measurement was purchased from Merck. All chemicals were used without further purification. Aqueous solutions were prepared with ultrapure water produced by the MilliQ system (Merck Millipore, Burlington, MA, USA, 18.2 MΩcm, TOC < 4 ppb).
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2

Synthesis and Characterization of Metal Phthalocyanines

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As shown in Fig. 1, MPcs contain Li2Pc, FePc, CoPc, CuPc (β-form), ZnPc, and SnPc. These MPc samples were purchased from Tokyo Chemical Industry Co., Ltd. and were used without further purification. Since MPcs have a conjugated double bond system, these species tend to stack with each other by way of π–π interaction.

Chemical structure of a metal phthalocyanine and abbreviations referring to various similar species.

Fig. 1
PEG (average molecular weight 20,000) and PVP (average molecular weight 40,000) were purchased from Kishida Chemical Co., Ltd. PVA (average molecular weight 24,000 and degree of saponification 98.5 mol%) was donated from Kuraray Co., Ltd. Notably, PVA can be dissolved in water at a temperature higher than 95 °C.
Pyridine (Tb = 116 °C), DMSO (Tb = 189 °C), DMF (Tb = 153 °C), and DMA (Tb = 166 °C (754 mmHg)) were purchased in JIS special grade (purity ≥99%) from Kanto Chemical Co., Inc. and used without further purification.
Ion-exchanged water was purchased from Kishida Chemical Co., Ltd. and used without further purification.
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3

Extraction and Modification of Pinus radiata Bark Polyphenols

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P. radiata bark was collected from the lumberyard of Unid Co., Ltd. (Gunsan, Korea), and the scales and inner barks were removed using a cutter knife. The refined bark was crushed and then pulverized into a powder of 1 mm or less using a high-speed mill. This bark powder was placed in a zipper bag and kept in a refrigerator until further use.
Sodium hydroxide (NaOH, 93%, Duksan Pure Chemicals, Ansan, Korea) was used for the preparation of polyphenol-rich AEs from the bark, and propylene oxide (PO, 99.5%, Daejung Chemical & Metals, Shiheung, Korea) was used for the hydroxypropylation of bark AEs. Concentrated HCl (35.0%, Duksan Pure Chemicals, Ansan, Korea) was used for acidification after hydroxypropylation. Acetic anhydride (93.0%, Duksan Pure Chemicals, Ansan, Korea) and pyridine (99.5%, Kanto Chemical, Tokyo, Japan) were used for acetylation. The deuterated solvent used was CD3OD (Eurisotop, Saint-Aubin, France). For the determination of hydroxyl value, a standard solution of 0.5 N KOH was prepared, and a standard solution of 0.5 N HCl was purchased from Daejung Chemical & Metals (Shiheung, Korea). A polyether polyol, polyethylene glycol #400 (PEG #400, Yakuri Pure Chemicals Co., Ltd., Kyoto, Japan), and a polyester polyol, SP320G (Seho Tech, Iksan, Korea), were used for the solubility tests of hydroxypropylated alkaline extracts (HAEs).
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4

Synthesis and Characterization of Fluorescent Probes

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All chemicals were purchased from commercial suppliers and used without further purification. Molecular sieves were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan) and predried at 300 °C for 2 h in a muffle furnace and then dried in a flask at 300 °C for 2 h in vacuo prior to use. Drierite was purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan) and predried at 230 °C for 2 h in a muffle furnace and then exposed to high vacuum. Dry solvents for reaction media (CH2Cl2, toluene, THF, MeCN, DMF, MeOH and pyridine) were purchased from Kanto Chemical Co. Inc. (Tokyo, Japan) and used without purification. Zn nano powder (<50 nm particle size) were purchased from Sigma-Aldrich. ATTO594 N-succinimidyl ester was purchased from ATTO-Tec.
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5

Synthesis of Aromatic Diamines for Polymeric Materials

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4-Aminocinnamic acid, pentafluoropropionic anhydride, triphenyl phosphite, 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 2,2-bis(4-aminophenyl)hexafluoropropane, 4,4′-diaminobenzophenone, and 4,4′-diaminodiphenyl sulfone were purchased from Tokyo Chemical Industry Co., LTD, Tokyo, Japan. Trifluoroacetic anhydride, triethylamine, and N,N-dimethylacetamide were purchased from FUJIFILM Wako Pure Chemical Corporation. Dichloromethane, methanol, ethanol, pyridine, N,N-dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP) were purchased from Kanto Chemical Co., Inc, Tokyo, Japan. All chemicals were directly used as purchased. 4,4′-Diamino-α-truxillic acid and 4,4′-diamino-α-truxillic acid dimethyl ester were synthesized based on previous research [4 (link),5 (link),10 (link)].
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6

Synthesis of Aspartame Precursor

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l-Aspartyl-l-phenylalanine methyl ester was supplied by Ajinomoto Co., Inc. Triphenyl phosphite (P(OPh)3), l-phenylalanine (Phe), succinic acid, ethylene diamine and p-phenylenediamine were purchased from Tokyo Chemical Industry Co., Ltd. 5% Palladium on activated carbon (Pd/C) and N-methylpyrrolidone (NMP) were purchased from FUJIFILM Wako Pure Chemical Corporation. Dimethyl sulfoxide (DMSO), sulfuric acid, nitric acid, pyridine, ethanol, tetrahydrofuran, ethyl acetate, acetone and toluene were purchased from Kanto Chemical Co., Inc. All the chemicals were directly used as purchased.
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7

Fluorescent Labeling of Rubrene Sulfonate

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RS (1 g) was dissolved in 50 mL of dimethyl sulfoxide with a few drops of pyridine (Kanto Chemical, Tokyo, Japan). Fluorescein isothiocyanate (20 mg; TCI, Tokyo, Japan) was added, followed by the addition of dibutyltin dilaurate (200 mg; Kanto Chemical, Tokyo, Japan), and the mixture was heated for 2 h at 95 °C. To remove the free dye, FITC-RS was dialyzed using a size 20 (MWCO: 14,000) dialysis membrane (FujiFilm, Tokyo, Japan) with water and then dried.
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8

Dry Solvent Preparation for Organic Synthesis

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All chemicals were purchased from commercial suppliers and were used as received, unless otherwise noted. The molecular sieves were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan) and were pre-dried at 300 °C for 2 h in a muffle furnace followed by drying in a flask at 250 °C for 2 h under vacuum, prior to use. The dry solvents used for the reaction media (CH2Cl2, toluene, THF, MeCN, DMF, and pyridine) were purchased from Kanto Chemical Co. Inc. (Tokyo, Japan) and were used as received. Other reaction media solvents were dried over molecular sieves and used without purification.
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9

Synthesis of Binder Polymer CP-2

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Example 2

Into a three-neck flask provided with a condenser and a stirrer, 6.97 g of 1,6-hexanediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 53.9 g of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Inc.) were put, and by being stirred at room temperature under a nitrogen flow to obtain a uniform solution. Next, 9.49 g of pyridine (manufactured by Kanto Chemical Co., Inc.) and 7.33 g of 4-dimethylaminopyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the reaction solution, followed by dissolving. Next, 22.03 g of 4,4′-oxybis(benzenesulfonylchloride) (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the flask, followed by stirring at room temperature for 1 hour, then, the temperature was raised to 60° C., and the resulting solution was allowed to react for 10 hours. The reaction solution was added dropwise to a mixed solution of 0.5 L of pure water and 0.5 L of methanol, and as a result, a polymer was precipitated. This was collected by filtration, washed, and dried, whereby 25.5 g of a binder polymer (CP-2) having a weight-average molecular weight of 52,000 was obtained. It was confirmed from the NMR spectrum, the IR spectrum, and GPC (polystyrene conversion) that the obtained product was the target substance.

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10

Synthesis of Binder Polymer for Electrochemical Devices

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Example 2

Into a three-neck flask provided with a condenser and a stirrer, 6.97 g of 1,6-hexanediamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 53.9 g of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Inc.) were put, and by being stirred at room temperature under a nitrogen flow, the solution became homogeneous. Next, 9.49 g of pyridine (manufactured by Kanto Chemical Co., Inc.) and 7.33 g of 4-dimethylaminopyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the reaction solution, followed by dissolving. Next, 22.03 g of 4.4′-oxybis(b enzenesulfonylchloride) (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to the flask, followed by stirring at room temperature for 1 hour, then, the temperature was raised to 60° C., and the resulting solution was allowed to react for 10 hours. The reaction solution was added dropwise to a mixed solution of 0.5 L of pure water and 0.5 L of methanol, and as a result, a polymer was precipitated. This was collected by filtration, washed, and dried, whereby 25.5 g of a binder polymer (CP-2) having an average molecular weight of 52,000 was obtained. It was confirmed from the NMR spectrum, the IR spectrum, and GPC (polystyrene conversion) that the obtained product was the target substance.

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