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Maleic anhydride

Manufactured by Merck Group
Sourced in United States, Germany, Spain, India, Sweden, United Kingdom

Maleic anhydride is a chemical compound used as a raw material in the production of various industrial and consumer products. It is a colorless, crystalline solid with a distinctive odor. Maleic anhydride serves as a building block in the synthesis of a wide range of chemicals, including resins, plasticizers, and agricultural products. Its core function is to provide a starting material for these diverse applications, without specific interpretation or extrapolation on its intended use.

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110 protocols using maleic anhydride

1

Maleic Anhydride Protein Modification

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Anhydride-modified proteins were produced as previously described [48 (link),49 (link)]. Briefly, bovine serum albumin (BSA) or human serum albumin (HSA) was dissolved in 0.1 M phosphate buffer (pH 8.6) to obtain a final concentration of 20 mg/mL. Maleic anhydride (Aldrich®, Rockville MD, USA, Cat#M188-25G-A) was dissolved in DMSO to obtain a final concentration of 1 M. Subsequently, the protein solutions were mixed with Maleic anhydride to a final concentration of 60 mM by the addition of five equivalent aliquots at 20 min intervals. After each addition, pH was adjusted to 9.0 using 5 M NaOH. The mixtures were incubated at 25 °C for an additional 2.5 h and then dialyzed against PBS overnight with constant gentle stirring. Protein concentrations were determined via Bradford assay.
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2

Synthesis of Bicyclic Compounds

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(-)-Menthol, (-)-borneol, S-(+)-3-octanol, S-(-)-2-methylbutanol-1, the 2nd generation Grubbs catalysts, dicyclopentadiene, 1,2,4-trichlorbenzene, maleic anhydride, Et3N, SOCl2, and cis-5-norbornene-endo-2,3-dicarboxylic anhydride (endo-NDA) were purchased from commercial suppliers (Sigma-Aldrich, ABCR GmbH, and TCI) and used as received unless otherwise noted. Methylene chloride and 1,2-dichloroethane were distilled over CaH2 under argon atmosphere and stored over molecular sieves (4 Å). Toluene was distilled in argon atmosphere and stored over molecular sieves (4 Å). ((1R,2S,5R)-6,6-Dimethylbicyclo[3.1.1]heptan-2-yl)methanol (pinanol) was prepared according to the procedure described earlier [36 (link)].
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3

Synthesis of PEO-Grafted Polycaprolactone

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ε-Caprolactone (ε-CL, TCI, Japan) was dried over CaH2 and distilled under reduced pressure prior to use. Methoxy poly(ethylene oxide) (MeO-PEO, Aldrich, Germany, Mn = 550, 2000 and 5000 g mol−1) were dried by azeotropic distillation with toluene. Maleic anhydride (Aldrich, Germany) was recrystallized from toluene and dried in vacuum for 24 h. Methylene chloride was dried by refluxing over CaH2 followed by distillation. Toluene was dried by refluxing over sodium-benzophenone complex. Stannous octoate [Sn(Oct)2, Aldrich, Germany], pentaerythritol (Aldrich, Germany), 4-dimethylaminopyridine (Across Organics, USA), trimethylamine (Daijung, Korea) were used without further purification. The solvents – dichloromethane (DCM), chloroform, acetonitrile (ACN), tetrahydrofuran (THF), dimethylformamide (DMF) – all HPLC grade, were used as received.
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4

Synthesis of o-Nitrophenylmaleimide

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The synthesis of o-nitrophenylmaleimide was carried out following the methodology [1 ]. 1.008 g (10.282 mmol) of maleic anhydride (Aldrich Chemical Co., 98% purity), was dissolved in 25 mL of anhydrous diethyl ether (Merck, 99.98% purity). Then, 1.400 g (10.148 mmol) of o-nitroaniline (Merck, purity 99.8%) was added to 10 mL of anhydrous diethyl ether, and the solutions were mixed with stirring at room temperature for 2 h. The solvent was allowed to evaporate for 24 h, and after several washes with anhydrous diethyl ether, 1.692 g (yield 76.5%) of a yellow solid was obtained. The melting point was determined to be 127 ± 1 °C, using a BI. Barnstead 9100 electrothermal model.
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5

Synthesis of Multifunctional Hydrogels

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Acrylamide (AM), β-cyclodextrin (β-CD), maleic anhydride (MAH), N,N-dimethylformamide (DMF), chloroform (CHCl3), acetone, 2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS), ethylene glycol, N, N’-methylenebisAcrylamide (MBAA), ammonium persulfate (APS), N,N,N’,N’-tetramethylenediamine (TMEDA), cadmium chloride (CdCl2-2.5H2O), N-acetyl-L-cysteine (NAC), tellurium powder (Te) and sodium borohydride (NaBH4) were purchased from Sigma-Aldrich and used as received. Carbamide, zinc citrate dehydrate, sodium citrate dihydrate were purchased from Sinopharm Chemical Reagent Co. (Shanghai, China); Fe3O4 nanoparticles (20 nm) were purchased from Aladdin-reagent (Shanghai, China). Deionized water was used in all of the experiments.
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6

Biopolymer-based Drug Delivery System

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Poly(d,l-lactic-co-glycolic acid (PLGA: 50/50, Mw: 33,000 Da) was purchased from Birmingham Polymers, Inc. (Birmingham, AL, USA). Poly(vinyl alcohol) (PVA, 87–89% hydrolyzed, Mw: 85,000–124,000 Da), Dex, dimethyl sulfoxide (DMSO), maleic anhydride, fluorescein (FI), IR-783, 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methyl-morpholinium chloride (DMTMM), sodium azide, propargyl amine, copper sulfate, ascorbic acid, and pyridine were bought from Sigma-Aldrich (St. Louis, MO, USA). Ethyl acetate, acetonitrile (ACN), toluene, and ether were used as received from Samchun (Gyeonggi, Korea). Dimethylformamide (DMF) were acquired from Junsei Chemical Co. (Chuo-ku, Tokyo), whereas methyltetrazine-PEG4-amine (TET) and trans-cyclooctene-amine (TCO) were from Click Chemistry Tools (Scottsdale, AZ, USA). Pluronic F-127 was used as received from BASF SE (BASF, Ludwigshafen, Germany). All other chemicals were of analytical grade and used without further purification. HA (1.0 MDa) was used as received from Humedix (Gyeonggi, Korea).
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7

Biomaterial Mesh Functionalization Study

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A polypropylene mesh, Gynemesh® PS (Ethicon, Somerville, NJ) was used. Maleic anhydride, chondroitin sulfate B, chitosan (low molecular weight, deacetylation degree 85%) were purchased from Sigma Aldrich (St. Louis, MO).
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8

Purification and Preparation of Reagents

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Tetrahydrofuran (THF, Labscan) was purified by distillation from sodium benzophenone ketyl under nitrogen prior to use. Maleic anhydride, sodium acetate, sodium carbonate, glutathione (GSH), guanidine hydrochloride (GuHCl), bovine β-lactoglobulin, yeast (Saccharomyces cerevisiae) enolase, bovine ubiquitin, NMM, tunicamycin and other reagents were purchased from Sigma-Aldrich and used as received. Human peroxiredoxin 3 was expressed and purified as described previously57 (link), and maintained in buffer with reducing agent tris(2-carboxyethyl)phosphine. Peroxiredoxin 3 was freshly desalted to remove reducing agents before use with a PD-10 column (GE Healthcare). Renilla luciferase vector was used from the Qiagen Cignal Heat Shock Response Reporter (luc) Kit. Luciferase activity was measure using Dual-Luciferase Reporter Assay System (Promega), as per the manufacturers protocol. The Httex1 fusion constructs were prepared as described previously58 (link). All constructs were sequenced for verification.
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9

Functionalized β-Cyclodextrin Magnetic Nanoparticles

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β–CD
(≥97% purity), maleic anhydride, iron oxide (Fe3O4) nanoparticles (97% purity), and acetone were purchased
from Sigma-Aldrich, India. N,N-Dimethylformamide
(DMF) was purchased from Qualigens, Bombay, India. MB, MG, and R6G
were obtained from Fisher Scientific, Navi Mumbai, Laboratory Sulab
Reagent, Baroda, and Loba Chemie Laboratory Reagents and Fine Chemicals,
Mumbai, India. Analytical grade reagents were used as received. The
solutions of dye were prepared using de-ionized water.
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10

Heterophasic PP Composites with Micro- and Nano-fillers

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In this study, ISPLEN® PB 170 G2M (supplied by Repsol–Chemicals, Madrid, Spain) was used. It is a PP heterophasic copolymer with density of 905 kg/m3 and MFR of 12 g/10 min.
Micro-fillers added to PP were talc, calcium carbonate, and silica; a lamellar phyllosilicate was used as nano-filler. Talc HTP1 grade (mean diameter: 1.9 µm) was supplied by IMI Fabi Spa (Valmalenco, Italy). Calcium carbonate OMYACARB® 1T-AV grade (mean diameter: 2 µm) was supplied by OMYA (Oftringen, Switzerland). Silica particles (diameter in the range 10–20 µm to 0.5–2 µm) were obtained from the rice husk supplied by S.P. Spa through a process of calcination of the husk itself. The lamellar phyllosilicate Cloisite® 20 was a bentonite modified with bis(hydrogenated tallow alkyl)dimethyl salt and supplied by BYK (Wesel, Deutschland). To enhance the dispersion of the nano-filler within the matrix, it was added to a compatibilizer, i.e., PP grafted with maleic anhydride (0.6 wt%), supplied by Sigma-Aldrich (Darmstadt, Deutschland).
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