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5 protocols using epichlorohydrin

1

Epoxy Resin Synthesis and Carbon Fiber Composites

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Terephthalaldehyde and tetrabutylammonium tribromide were purchased from Sigma–Aldrich (USA). Jeffamine D-230 (n ∼2.5) amine curing agent was purchased from New Seoul Chemical (Korea). Epoxy resin (YD115) was purchased from Kukdo Chemical (China). Epichlorohydrin was purchased from Tokyo Chemical Industry (Japan). Sodium hydroxide (50% solution) was purchased from Samchun Chemicals (Korea). Carbon fiber (T300) was purchased from Toray. Unless otherwise stated, all reagents were purchased from commercial suppliers and used as-received.
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2

Synthesis of 1-(Oxiran-2-ylmethyl)piperidine

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1-(Oxiran-2-ylmethyl)piperidine was synthesized using piperidine (Sigma-Aldrich, Inc., St. Louis, MO, USA) and epichlorohydrin (Tokyo Chemical Industry Co., Ltd., Tokyo, Japan) and the following procedure. An aqueous solution (3 mL) of 1000 mmol of epichlorohydrin was added to cooled piperidine (1000 mmol), and the mixture was stirred for 1 h at 273 K, followed by further agitation at 293 K for 30 min. Then, 30% NaOH aq was added to the mixture with stirring for 3 h. After the reaction was complete, the product was extracted with diethyl ether and rinsed with ultrapure water several times. The combined organics were dried over MgSO4. The solvent was evaporated, and the resulting light yellow crude product was purified with a Kugelrohr distillation apparatus. The colorless final product was confirmed by 1H NMR, 13C NMR, and mass spectrometry. 1H NMR (400 MHz, DMSO-d6) δH 1.36 (m, 2H, J = 5.7 Hz), 1.49 (m, 4H, J = 5.7 Hz), 2.15 (dd, 1H, J = 13.2 Hz, 6.4 Hz), 2.34–2.41 (m, 5H), 2.53 (dd, 1H, J = 13.6 Hz, 4.0 Hz), 2.67 (t, 1H, J = 5.2 Hz), 2.97 (m, 1H, J = 3.3 Hz). 13C-NMR (100 MHz, DMSO-d6) δC 23.9 (s), 25.5 (s), 44.2 (s), 49.8 (s), 54.4 (s), 61.1 (s). High-resolution mass spectrometry (HRMS) (electron ionization (EI)), m/z: calcd for C8H15NO 141.1154 [M]+; found 141.1156.
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3

Purification and Characterization of Organic Compounds

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12-hydroxystearic acid (purity > 80.0%), hexane (purity > 96.0%), heptane (purity > 99.0%), octane (purity > 95.0%), nonane (purity > 98.0%), decane (purity > 99.0%), cyclohexene (purity > 99.0%), and acetone (purity > 99.5%) were purchased from Kanto Chemical Co., Inc., Japan. o-xylene (purity > 98.0%), m-xylene (purity > 99.0%), p-xylene (purity > 99.0%), styrene (purity > 99.0%), α-methyl styrene (purity > 99.0%), n-butylbenzene (purity > 99.0%), di-isononyl adipate (mixture of branched-chain isomers), d-limonene (purity > 95.0%), hexachloroacetone (purity > 98.0%), methyl chloroformate (purity > 96.0%), ethyl chloroformate (purity > 98.0%), fluorobenzene (purity > 99.0%), epichlorohydrin (purity > 99.0%), methylene dichloride (purity > 99.0%), 2-methylfuran (purity > 98.0%), and γ-butyrolactone (purity > 95.0%) were purchased from Tokyo Chemical Industry Co., Ltd., Tokyo, Japan. The ultra-pure water was prepared using a Direct-Q Water Purification System supplied by EDM Millipore Corporation, and the resistivity was confirmed to be 18.2 MΩ cm. All chemicals were used as received.
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4

Cellulose-Based Adsorbent Characterization

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The cellulose was derived from Osaki cotton balls from Osaki Medical Co., Ltd. (Nagoya, Japan) in this study. The sodium dodecyl sulfate (SDS) and epichlorohydrin were sourced from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan), and the dodecyl dimethyl tertiary amine was from FIJIFILM Wako Chemical Co., Ltd. (Osaka, Japan). All reagents used were of analytical grade. During the whole working process, water (>18.2 MΩ) treated by an ultra-pure water system (RFU 424TA, Advantech Aquarius, Irvine, CA, USA) was used. In addition, a water bath incubator (BT100, Yamato Kagaku Co., Ltd., Tokyo, Japan), a vacuum drying oven (DP33, Yamato Kagaku Co., Ltd., Tokyo, Japan), and a pH meter (HORIBA F-72, Tokyo, Japan) were used in this work.
Furthermore, a scanning electron microscopy and energy dispersive spectrometry (SEM-EDS, JEOL, Akishima, Tokyo, Japan: JCM-6000 with JED-2300), ion sputtering (JFC-1100E, JEOL, Akishima, Tokyo, Japan), Fourier transform infrared spectroscopy (FT-IR4200, Jasco, Hachioji, Tokyo, Japan) nuclear magnetic resonance (NMR, AVANCE III HD400, Bruker, Billerica, MA, USA), Zeta-potential measurement with electrophoretic light scattering (ELS, Otsuka, Tokyo, Japan: ELSZ-2000ZS), and differential refractometry (RID-6A, SHIMADZU, Kyoto, Japan) were employed in this work.
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5

Synthesis of Poly(Amino Acid) Derivatives

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n-Butylamine and β-benzyl-L-aspartate-N-carboxyanhydride (BLA-NCA) were obtained from NOF Corporation (Tokyo, Japan). Ethylene oxide was obtained from 3M Japan Co., Ltd. (Tokyo, Japan). Tetrahydrofuran (THF) (super dehydrated, purity >99.5%) and Toluene (super dehydrated, purity >99.5+%) were purchased from Kanto Chemical, Co., Inc. (Tokyo, Japan). Ethanol, diethyl ether, N,N-dimethylformamide (DMF) and piperidine (purity >98.0%) were purchased from Fujifilm Wako Pure Chemical, Co., Inc. (Tokyo, Japan). 1,1,3,3-Tetramethylguanidine (purity >99.0%), 2-methoxyEthanol (purity >99.0%) epichlorohydrin (purity >99.0%), triisobutylaluminum, N,N-dimethylformamide (purity >99.5%), 4-dimethylaminopyridine (purity >99.0%), 1-(3-dimethylaminopropyl)-3-ethylcordiimide hydrochloride (purity >98.0%), N-[(9H-fluoren-9-ylmethoxy)carbonyl]glycine (purity >98.0%), N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-leucine (purity >98.0%) and N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-tyrosine (purity >95.0%) were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Sodium hydroxide, hydrochloric acid and HEPES buffer were purchased from Sigma-Aldrich (St. Louis, MO, U.S.A). Fetal bovine serum (FBS), Dulbecco’s Modified Eagle’s Medium and Penicillin-Streptomycin were obtained from Thermo Fisher Scientific (Waltham, MA, U.S.A).
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