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8 protocols using anhydrous 1 4 dioxane

1

Synthesis of Triformylphloroglucinol Precursor

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The trialdehyde precursor, 1,3,5-triformylphloroglucinol (Tp), was synthesized by following a previously reported procedure. 12 The materials, 4-bromo-3-methylaniline (97%), 4-bromo-2,5-dimethylaniline (99%), palladium(II) acetate (99.9%), and anhydrous 1,4-dioxane (99.8%), were purchased from Merck. Caesium carbonate (99%) was purchased from Alfa Aesar. All reagents were used as received without further purification.
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2

Adsorption of Zn(II) from Aqueous Solutions

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Anhydrous 1,4-dioxane, active carbon (particle size <100 µm), iminodiacetic acid, NaOH, HCl, H 2 SO 4 , HNO 3 , Mn(NO 3 ) 2 , K 2 SO 4 , NaCl, CH 3 COOH, CH 3 COONa, NaH 2 PO 4 , Na 2 HPO 4 , Pb(NO 3 ) 2 , FeSO 4 , CuSO 4 , Co(NO 3 ) 2 , NiSO 4 , Zn(NO 3 ) 2 , Hg(NO 3 ) 2 , Al (NO 3 ) 3 , AgNO 3 , Mg(NO 3 ) 2 , Ca(NO 3 ) 2 , Ba(NO 3 ) 2 , and ethanol were products of Merck (Darmstadt, Germany).
All the reagents were of analytical grade and used without any further purification.
The stock solution (1000 mg/L) of Zn(II) was prepared by dissolving an appropriate amounts of Zn(NO 3 ) 2 , in deionized water. To adjust the pH of the solution, 10 mL of 0.01 M acetic acid-acetate buffer (pH 3-6.5) or 0.01 M phosphate buffer (pH 6.5-9) was used wherever suitable.
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3

Synthesis and Characterization of Doxorubicin-Loaded Polymeric Nanoparticles

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Poly(ethylene glycol) (PEG) methyl ether, molecular weight [MW] 5,000 Da), L-lactide (3,6-dimethyl-1,4-dioxite-2,5-dione), stannous octoate (Sn[Oct]2, Tin[II]2-ethylhexanoate), 4-(dimethylamino)pyridine (DMAP), pyren, succinic anhydride, pyridine, triethylamine (TEA), N-hydroxysuccinicimide (NHS), N,N′-dicyclohexylcarbodiimide (DCC), anhydrous 1,4-dioxane, N,N-dimethylformamide (DMF), D2O-d6, and CDCl3 were purchased from Sigma-Aldrich (St Louis, MO, USA). Triphosgene and branched PEI (MW 10,000 Da) were purchased from Alfa Aesar® Johnson Matthey Korea (Seoul, South Korea). Dichloromethane (DCM), methanol (MeOH), ethanol (EtOH), and toluene were purchased from Honeywell Burdick & Jackson® (Muskegon, MI, USA). Dox⋅HCl was purchased from Borung Co. (Seoul, South Korea). All other chemicals used were of analytical grade. For cell culture, human breast cancer MCF7 cells and cervical cancer KB cells were obtained from the Korean Cell Line Bank (KCLB, Seoul, South Korea). RPMI 1640 medium, fetal bovine serum (FBS), penicillin, and streptomycin were purchased from Welgene (Seoul, South Korea). Cell Counting Kit-8 (CCK-8) was obtained from Dojindo Molecular Technologies (Tokyo, Japan). P(Asp) was prepared as previously reported.20 The MW of P(Asp) was ~4,000 Da (degree of polymerization =35).
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4

Synthesis and Characterization of PEG-PLL-PLA Nanoparticles

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Methoxy polyethylene glycol amine (mPEG-NH2, molecular weight [MW] 5,000), N6-Carbobenzyloxy-l-lysine, 3,6-dimethyl-1,4-dioxite-2,5-dione, DMA, stannous octoate (Tin[II]2-ethylhexanoate), 4-(dimethylamino)pyridine (DMAP), succinic anhydride, pyridine, triethylamine (TEA), N-hydroxysuccinimide (NHS), N,N′-dicyclohexylcarbodiimide (DCC), 9,10-dimethylanthracene, trifluoroacetic acid (TFA), 33% HBr in acetic acid, anhydrous 1,4-dioxane, dimethyl sulfoxide (DMSO)-d6, and anhydrous dimethylformamide (DMF) were purchased from Sigma-Aldrich (St Louis, MO, USA). Triphosgene was purchased from Alfa Aesar® Johnson Matthey Korea (Seoul, South Korea). Dichloromethane and toluene were purchased from Honeywell Burdick & Jackson® (Muskegon, MI, USA). Chlorin e6 (Ce6) was purchased from Frontier Scientific Inc. (Logan, UT, USA). All other chemicals used were of analytical grade. For cell culture, human cervical cancer KB cells were obtained from the Korean Cell Line Bank (KCLB, Seoul, South Korea). RPMI 1640 medium, fetal bovine serum (FBS), penicillin, and streptomycin were purchased from Welgene (Seoul, South Korea). Cell Counting Kit-8 (CCK-8) was obtained from Dojindo Molecular Technologies (Tokyo, Japan). PEG-PLL-PLA triblock copolyelectrolyte was prepared as described previously.17 (link)
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5

Fructose Conversion to Biofuels via Microwave-Assisted Catalysis

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The procedure described by Bispo et al.29 (link) was followed. Specifically, 44 wt% fructose solution was prepared by dissolving 4.4 g of fructose in 5.6 g of Milli-Q® water. For each reaction, solid catalyst, 300 mg of fructose solution and 900 mg of a methyl-isobutyl ketone–butanol (MIBK : BuOH) 70 : 30 solution were weighed into a 2 mL microwave vial reactor. The reaction was carried out in a Biotage® Initiator+ microwave apparatus. After the reaction, the crude was filtered to recover the catalyst. Then, 10 mL H2O and 10 mL of MIBK : BuOH 70 : 30 solution were added to the reaction medium. Then, aliquot of the reaction was monitored in a LC-2030C Plus high-performance liquid chromatography (HPLC) system. For solvent testing, MIBK:BuOH solution was substituted by alternative solvents: MeOH, 1,4-dioxane, DMSO and acetone. d-(−)-Fructose (≥99%), 4-methyl-2-pentanone HPLC grade (≥99%), 1-butanol HPLC grade (≥99.7%), methanol HPLC grade (99.99%) and anhydrous 1,4-dioxane (99.8%) were purchased from Sigma-Aldrich.
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6

Synthesis and Characterization of Novel Fluorescent Probes

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3-Diethylaminophenol, 1,6-dihydroxynaphthalene,
5-(diethylamino)-2-nitrosophenol, tert-butyl (3-bromopropyl)carbamate,
propargyl bromide, and pentafluorophenol were purchased from Tokyo
Chemical Industry (TCI) and used as received. Anhydrous triethylamine,
anhydrous 1,4-dioxane, 4-cyano-4-(phenylcarbonothioylthio)pentanoic
acid, and lauroyl peroxide were purchased from Sigma-Aldrich and used
without purification. Acryloyl chloride and n-dodecylamine
were purchased from abcr Gute Chemie. Jeffamine@M-1000 polyetheramine
was purchased from Huntsman. Azobisisobutyronitrile (AIBN) was purchased
from Sigma-Aldrich and recrystallized from methanol. Dulbecco’s
modified Eagle’s medium (DMEM) and fetal bovine serum (FBS)
were purchased from Thermo Fisher Scientific. Other solvents were
purchased from Biosolve except the deuterated solvents, which were
purchased from Cambridge Isotopes Laboratories. 2-Hydroxy Nile red,55 (link) Nile red-alkyne,56 (link) BTA-NH2, and BTA-N3 were prepared following
literature procedures.27 (link)
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7

Biodegradable Polyurethane Foam Synthesis

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Reactant materials, including polycaprolactone (PCL) triol (PCL, Mn = 900), poly-caprolactone-block-polytetrahydrofuran-block-polycaprolactone copolymer (PCTC, Mw = 2000, equal polymerization degree for each block), hexamethylene diisocynate (HDI), 1,4-butanediol (BD), dibutyltin dilaurate (DBTDL), and sodium chloride (NaCl) as a porogen were purchased from Sigma–Aldrich. PCL triol, PCTC, and BD were vacuum dried at 75 °C for 2 h prior to use. HDI was dried using a 4Å molecular sieve and then vacuum distilled. NaCl particles were sieved to 100~250 μm in size. Anhydrous 1,4-dioxane, absolute ethanol, and isopropanol were purchased from Sigma–Aldrich and used as received. Deionized (DI) water was used throughout the experiment.
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8

Crystallization Yield Calculation Protocol

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Phenazine (98%, Sigma), Caffeine (99%, Sigma), Isonicotinamide (99%, Sigma), Niflumic acid (99%, Sigma) and 4-Hydroxybenzoic acid (99%, Sigma) were used as received. The insulator solvent was chosen to be anhydrous 1,4-dioxane (99.8%, Sigma). All chemicals were used without further purification.
The yield (y) of recovery was calculated based on the equation below:
(1)
Here m (mg) is the mass of crystals A (either CAF or PHE) collected from either of the electrodes; ct (mg/ml solvent) is the overall concentration of A in the mixed suspension; c * (mg/ml solvent) is the solubility of A in the mixture solution at the temperature the crystals were collected; V (ml) is the volume of solvent.
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