Imidazoline As a Volatile Corrosion Inhibitor for Mitigation of Top- and Bottom-of-the-Line CO2 Corrosion in Carbon Steel Pipelines.

A fatty acid imidazoline-based inhibitor was synthesized via a facile solvent-free synthesis method between tall oil fatty acid (TOFA) and diethylenetriamine (DETA) under atmospheric conditions with a short reaction time. The as-synthesized imidazoline (S-Imd) acted as an effective inhibitor for reducing or preventing corrosion of carbon steel pipelines at both bottom of the line (BOL) and top of the line (TOL) positions under simulated conditions of a gas pipeline in a CO2-saturated environment. The inhibition efficacy was examined by both weight loss and electrochemical measurements, such as the electrochemical impedance spectrum (EIS), potentiodynamic polarization (PDP), and linear polarization resistance (LPR). The results revealed that the S-Imd, 2-(8-heptadecenyl)-2-imidazoline-1-ethanamin, at 300 ppm exhibited a superior inhibition efficiency of up to 91.6 and 89.9% for BOL and TOL corrosion tests, respectively. The surface morphology of the carbon steel test specimens was also examined using scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDAX), and contact angle analysis. It was found that the as-synthesized S-Imd acted as a mixed-type inhibitor that exhibited a decreased surface roughness and oxide layer on carbon steel surfaces. However, the water contact angle was found to increase, implying enhanced hydrophobicity of the surface. Adsorption of the imidazoline molecules on carbon steel surfaces followed the Langmuir adsorption isotherm. The present work provides very promising results in the synthesis and utilization of the studied imidazoline as a volatile corrosion inhibitor (VCI), especially for carbon steel pipelines in petroleum industries.

Mn(OAc)3-Mediated One-Pot Condensation-Oxidative Annulation of 2-Alkynylanilines and 1,3-Ketoesters: Synthesis of 2-Substituted Quinolines.

A general protocol for oxidative annulation was developed for the preparation of 2-methyl-3,4-diacylquinolines directly from 2-alkynylanilines and 1,3-ketoesters. The reactions were mediated by Mn(OAc)3 in acetic acid at room temperature, which led to the desired quinoline products in one-pot in low to good overall yields on a wide range of substrates. The current method was convenient to conduct and proceeded under mild conditions in short reaction times.

Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[d][1,3]oxazines and Their Application in the Synthesis of 4H-Furo[3,2-b]indoles.

The combination of catalytic aqueous hydrochloric acid (HCl) and N-bromosuccinimide (NBS) generated electrophilic bromine monochloride (BrCl), which readily induced spiroannulation of 2-alkynolyl anilides (n = 1-3) to form gem-dibromospirocyclic benzo[d][1,3]oxazines in up to 92% yield. The reaction occurred under mild and metal-free conditions using EtOAc as a green solvent. The resulted spirocyclic products contained benzo[d][1,3]oxazine, which was useful both as a pharmacophore and synthetic precursor. In addition, the current protocol allowed to effortlessly introduce the sp3-gem-dibromide carbon adjacent to the sterically demanding spiroketal center. These spiroheterocycles (n = 1) were shown to be synthetically versatile and conveniently maneuvered. Base-promoted debrominative aromatization of these spirocycles unmasked rare and synthetically useful 2-aryl-3-bromofurans in mostly excellent yields. These 3-bromofurans were well-suited substrates for intramolecular Ullmann C-N bond coupling to construct difficult-to-prepare 4H-furo[3,2-b]indoles. Additionally, the current protocol was flexible and adaptable to preparing the gem-dichloride variants.

Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3.

1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination of TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only terminal alkynes were selectively converted to the corresponding vinyl triflates, while internal alkynes were not reacted. A broad range of substrates were successfully converted to the corresponding 1,1-disubstituted vinyl triflates in good to excellent yields even those with internal alkyne moieties present in the molecules.

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters.

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Bi(OTf)3-Catalyzed One-Step Catalytic Synthesis of N-Boc or N-Cbz Protected α-Branched Amines.

In this paper, N-Boc and N-Cbz protected α-branched amines are synthesized directly from commercially available aromatic/heteroaromatic compounds, aldehydes, and tert-butyl or benzyl carbamate bearing a variety of substituents. Bismuth(III) triflate is found to be a highly effective catalyst for this one-pot, three-component coupling reaction. In addition, the use of mild reaction conditions, low catalytic loading, easy removal of the N-protective group, and one-step synthesis under "open-flask" are advantages of the present procedure.