Reaction Of Cyanuric Chloride Research Articles

SYNTHESIS OF A NOVEL SILICONE- AND TRIAZINE-BASED COPOLYMER WITH FURFURYL SIDE GROUPS

S-triazine derivatives are known to have great potential in diversifying the structural design of polymer materials due to the stepwise reaction of cyanuric chloride, particularly in optoelectronic applications. In addition, the hydrogen bonds formed by the triazine ring are known to play an important role in molecular arrangement, providing triazine-based polymer materials with excellent mechanical properties. In the present work, a triazine-furan precursor will be combined with polydimethylsiloxane (PDMS) and polyoxypropylenediamine to create a novel polymer that bears furfuryl side groups. This polymer has great potential to be used for self-healing applications due to the reversibility of triazine π-π stacking and hydrogen bonding as well as the ability of the furfuryl group to form dynamic covalent bonds. Thin-layer chromatography (TLC) and gel permeation chromatography (GPC) was used to investigate the reaction conditions (GPC). The research of this reaction revealed that the best conditions for the synthesis of this copolymer were at a temperature of 110 oC for 24 hours and determined an average molecular weight (Mn) of around 19800 (g/mol). Fourier-transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) are used to determine the structure of the synthesized compounds. Besides that, from the 1H-NMR spectrum NMR was found that feeding molar of 21.32/1/19.50 for TF, PDMS, and Jeffamine, respectively.

Demulsification of stable seawater/Arabian heavy crude oil emulsions using star-like tricationic pyridinium ionic liquids

Green oil-field chemicals based on ionic liquids (ILs) are highly recommended as demulsifiers for heavy crude oil emulsions due to their low vapor pressure, high thermal and chemical stability against degradation in harsh processing conditions. Novel multifunctional tricationic pyridinium ionic liquids (TCPyILs) were synthesized by the reaction of cyanuric chloride with tetraethylene glycol followed by its linking with quaternized aminopyridinium bromide using Bis(chloroethyl) ether as a linker. The chemical structures, surface and interfacial activities and thermal stabilities of the prepared pyridinium ILs were investigated. The amphiphilicity, surface and interfacial activity of the prepared TCPyILs recommended their application as chemical additives in petroleum industry. To the best of our knowledge, it is the first time to apply TCPyILs as demulsifiers for W/O emulsions with high stability and low droplet size (around 2 μm). Comparing with traditional monocationic pyridinium ILs, the prepared TCPyILs had higher efficiencies to demulsify W/O emulsions with different Vol %. The effects of alkyl chain lengths, demulsifier doses and RSN values on the demulsification activities were studied. The results indicated that TCPyILs with nonyl and tetradecyl alkyl chains had better and higher demulsification efficiency comparing with those containing hexadecyl alkyl chains. The demulsification efficiencies of TNPy and TTPy ILs for W/O (50/50, 30/70 and 10/90 vol%) reached 100% even at low concentrations.

Novel Annulation of Cyanuric Chloride with 2‐Aminobenzamides: A New Approach to 2‐Amino‐3‐substituted Quinazolin‐4(3H)‐ones

AbstractA simple and efficient method for preparation of 2‐amino‐ 3‐substituted quinazolin‐4(3H)‐ones by reaction of cyanuric chloride with 2‐amino N‐substituted benzamides in acetonitrile‐water (2 : 1) using sodium bicarbonate as a mild base is described. Using this metal‐free method, a variety of 2‐amino‐3‐substituted quinazolin‐4(3H)‐ones were obtained in good to excellent yields. Here, both organic and inorganic bases were found to promote this reaction and the best results were observed with sodium bicarbonate. This study is the first observation of cyanuric chloride to act as a source for creation of amine functionality in 2‐amino‐3‐substituted quinazolin‐4(3H)‐ones.

Synthesis, Characterization of sym-2,4,6-trisubstituted-s-Triazine Derivatives and Their Effects on Flame Retardancy of Polypropylene Composites

Polypropylene (PP) is flammable material, which brings latent danger to the environment and human society. Therefore, developing new environmentally friendly and effective flame-retardant is one of the most important ways to improve the flame retardancy of PP and improve safety during its lifetime. Herein, we describe the synthesis of five sym-2,4,6-trisubstituted-s-triazine derivatives, namely, N2,N4,N6-triphenyl-1,3,5-triazine-2,4,6-triamine (TAT), N2,N4,N6-tris(4-bromophenyl)-1,3,5-triazine-2,4,6-triamine (TBAT), N2,N4,N6-tris(4-chlorophenyl)-1,3,5-triazine-2,4,6-triamine (TCAT), 4,4′,4″-((1,3,5-triazine-2,4,6-triyl) tris(azanediyl)) triphenol (THAT), and N2,N4,N6-tris(4-methoxyphenyl)-1,3,5-triazine-2,4,6-triamine (TMAT), from the reaction of cyanuric chloride and p-substituted aniline employing conventional heating or microwave irradiation. The prepared compounds characterized by different techniques, such as Fourier-transform infrared (FTIR), Ultra-Violet and Visible (UV-Vis), Nuclear Magnetic Resonance spectroscopy (1H-NMR and 13C-NMR), Thermogravimetric Analysis (TGA), and differential scanning calorimetry (DSC). The effect of substituent on the aniline moiety has great impact on its thermal stability, as observed from the TGA and DSC data. Based on the TGA and DSC results, three triazine derivatives TAT, TBAT, and TMAT were used as charring agents in the presence of different proportions of ammonium polyphosphate (APP) to form an intumescent flame-retardant (IFR) system, to improve the flame retardancy of PP. The flammability property of PP was investigated by a vertical burning test (UL94). The results of UL94 revealed that the TXAT/APP (IFR) system influence the PP and could improve the flame retardancy of PP. Best results were obtained with the mass ratio of APP and TXAT 2:1. When the IFR loading was 25 wt%, it displayed great influence and passed V-0 with TMAT, and V-1 with both TAT and TBAT in the UL94 test.

Hydrophilic triazine-based dendron for copper and lead adsorption in aqueous systems: Performance and mechanism

In this study, a triazine-based dendron produced by the reaction of cyanuric chloride and diamine was synthesized successfully and applied in the adsorption of copper and lead ions in aqueous systems. The effects of pH, contact time, adsorbent dosage, solution temperature, initial concentration, coexisting substances and desorption were systematically performed in the case of adsorption operations. The adsorption of the both heavy metal ions followed the pseudo-second-order kinetic model best, with the equilibrium adsorption time at 120 min. The adsorption isotherms were well-described by the Langmuir model and the calculated maximum adsorption capacity of Cu2+ and Pb2+ was 103.68 and 133.47 mg g−1 at 25 °C, respectively. Based on the Dubinin-Radushkevich (D-R) isotherm model and calculation of adsorption free energy, the sorption processes for Cu2+ and Pb2+ were both chemisorption. Desorption and reuse experiments demonstrated that without significant loss in its original performance that could be reused in five cycles. The high density of terminal hydroxyl groups on the dendron was believed to participate in the chemical sorption process of Cu2+ and Pb2+ due to electrostatic attraction and surface complexation in the binding process. These results suggested the triazine-based dendron can be used as an efficient adsorbent for metal ions removal from wastewater.

Synthesis and characterization of new nitrogen‐ and oxygen‐rich cyclohexanone–formaldehyde resin for fast Cd(II) adsorption in aqueous solution

AbstractA new structure of cyclohexanone–formaldehyde resin (CFR) was synthesized via in situ condensation reaction of 2,4,6‐tris(p‐formylphenoxy)‐1,3,5‐triazine (TFPA) with CFR. TFPA was prepared by the reaction of cyanuric chloride and p‐hydroxybenzaldehyde and its structure was confirmed using spectroscopic methods and elemental analysis. The structural, thermal and morphological properties of the nitrogen‐ and oxygen‐rich CFR were studied using Fourier transform infrared spectroscopy, X‐ray diffraction, thermogravimetric analysis and field emission scanning electron microscopy. After characterization, the resin was used as an adsorbent for Cd(II) due to the high level of nitrogen and oxygen in its structure. The effects of various parameters such as pH, concentration and time on the adsorption process were studied. The maximum adsorption capacity of cadmium at pH 8 in 5 min was 83.61 mg L−1. The adsorption isotherm was applied to the Langmuir, Freundlich, Temkin and Dubinin–Radushkevich models. Comparing the correlation coefficient (R2), the Langmuir model was fitted well. Pseudo‐first‐order, pseudo‐second‐order, Elivich and intra‐particle diffusion models of adsorption kinetics were explored. The pseudo‐second‐order model can better explain the adsorption kinetics that shows adsorption being dependent on the number of active sites of the adsorbent. © 2019 Society of Chemical Industry

Study of the Friedel-Crafts Reaction of Cyanuric Chloride with Low-Boiling Aromatic Ring

Study of the Friedel-Crafts Reaction of Cyanuric Chloride with Low-Boiling Aromatic Ring

Investigation of novel monopodal and dipodal oxy-Schiff base triazine from cyanuric chloride: Structural and antimicrobial studies

ABSTRACTDuring the last few years, the potential of s-triazine derivatives in agrochemical and medicinal properties have been subjected to investigation. s-Triazine derivatives have received great attention due to their significant antimicrobial, antibacterial, antifungal, anti-HIV, anticancer, and a wide array of other biological activities. The present study reported a method for achieving Dipodal systems formed by reaction 2,4,6-trichloro-1,3,5-triazine and 4-hydroxybenzaldehyde, 2-aminophenol. Herein, we reported the synthesis of a dialdehyde and its Schiff base as a new template. The reaction of cyanuric chloride with 1 equiv. methanol and 2 equiv. of p-hydroxybenzaldehyde gave the desired dialdehyde. The dialdehyde was then reacted with 2-aminophenolto afford the corresponding multidirectional oxy-Schiff base triazines. The structures of the compounds were identified by FT-IR,1H-NMR and elemental analysis. Their antimicrobial activities were performed by using the broth microdilution method in DMSO: Phosphate Buffered Saline (PBS) against eight bacteria strain and one yeast strain. The results of the test were compared with gentamicin. It has been determined that 2,4-Bis(2-hydroxyphenylimino-4'-formylphenoxy)-6-methoxy-1,3,5-triazine (3) (2DP2AF) and 2-(2-hydroxyphenylimino-4'-formylphenoxy)-4-(4'-formylphenoxy)-6-methoxy-1,3,5-triazine (2) (1DP2AF) have significant antibacterial and antifungal activity against Enterococcus faecalis and Candida albicans and these effects were close to the control antibiotic used. Ent. faecalis was the most sensitive strain against both two tested chemicals. It was determined that our chemicals have similar antifungal capacity when compared to gentamicin.

Synthesis of a porphyrinic polymer for highly efficient oxidation of arylalkanes in water

A highly stable covalent-porphyrinic framework Mn-CPF-1 was synthesized by reaction of cyanuric chloride and tetraphenylamine porphyrin (TAPP) and subsequent metallation. Mn-CPF-1 exhibits remarkable catalytic activity and stability on catalytic oxidation of arylalkanes in water under mild conditions, which is much superior to the homogeneous analog Mn-tetraphenylporphyrin (Mn-TPP) under identical conditions.

Donor-π-acceptor, triazine-linked porphyrin dyads as sensitizers for dye-sensitized solar cells

Two porphyrin dyads with the donor-π-acceptor molecular architecture, namely ( ZnP )-[triazine-gly]-( H 2 PCOOH ) and ( ZnP )-[triazine-Npip]-( H 2 PCOOH ), which consist of a zinc-metalated porphyrin unit and a free-base porphyrin unit covalently linked at their peripheries to a central triazine group, substituted either by a glycine in the former or a N-piperidine group in the latter, have been synthesized via consecutive amination substitution reactions of cyanuric chloride. The UV-vis absorption spectra and cyclic-voltammetry measurements of the two dyads, as well as theoretical calculations based on Density Functional Theory, suggest that they have suitable frontier orbital energy levels for use as sensitizers in dye-sensitized solar cells. Dye-sensitized solar cells based on ( ZnP )-[triazine-gly]-( H 2 PCOOH ) and ( ZnP )-[triazine-Npip]-( H 2 PCOOH ) have been fabricated, and they were found to exhibit power conversion efficiency values of 5.44 and 4.15%, respectively. Photovoltaic measurements (J–V curves) and incident photon to current conversion efficiency spectra of the two solar cells suggest that the higher power conversion efficiency value of the former solar cell is a result of its enhanced short circuit current, open circuit voltage, and fill factor values, as well as higher dye loading. This is ascribed to the existence of two carboxylic acid anchoring groups in ( ZnP )-[triazine-gly]-( H 2 PCOOH ), compared to one carboxylic acid group in ( ZnP )-[triazine-Npip]-( H 2 PCOOH ), which leads to a more effective binding onto the TiO 2 photoanode. Electrochemical impedance spectra show evidence that the ( ZnP )-[triazine-gly]-( H 2 PCOOH ) based solar cell exhibits a longer electron lifetime and more effective suppression of charge recombination reactions between the injected electrons and electrolyte.

Synthesis, fastness properties, color assessment and antimicrobial activity of some azo reactive dyes having pyrazole moiety

Some new azo dye derivatives having pyrazole and trichlorotriazine moieties were synthesized and were evaluated as reactive dyes for the exhaust dyeing of cotton fiber. The title dyes 5a–c were synthesized from reactions of diazonium salts of 3-substituted-1-phenyl-5-aminopyrazoles 2a–c with 6-amino-7-hydroxy-2-naphthalenesulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid and/or cyanuric chloride. Other reactive dyes 7a–f were synthesized from reaction of cyanuric chloride and 4-arylazo-3-substituted-1-phenyl-5-aminopyrazoles 6a–f. The synthesized dyes were applied to cotton fiber and their color fastness to light, washing, perspiration, and rubbing were also measured. The dyes showed good to moderate affinity to cotton fiber. The biological screening showed that most of the tested compounds display promising antimicrobial activities against the tested microorganisms.

ChemInform Abstract: Metal‐Free Regioselective C—C Bond Cleavage in 1,3,5‐Triazine Derivatives of β‐Diketones.

AbstractThe reaction of cyanuric chloride (I) with 3 equivalents of ketones (II) in the presence of 3 equivalents of KOH affords adducts (IV), which are converted into deacylated derivatives (III) by treatment with aqueous HCl solution in MeOH.

Synthesis, characterization, and antimicrobial evaluation of novel trichalcones containing core s-triazine moiety

A series of ten new trichalcones containing core s-triazine moiety were synthesized. The intermediate 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine was synthesized by the reaction of cyanuric chloride with sodium salt of p-hydroxy benzaldehyde using phase-transfer catalyst. Thus, the prepared 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine has been subsequently treated with various acetophenones to afford title compound in excellent yields. The structures of intermediate and newly synthesized trichalcones were confirmed by physical and spectral analysis. All the trichalcones were evaluated for antibacterial and antifungal activities. Selected trichalcones showed good to excellent antibacterial and antifungal activities with reference to the well-established standards.

Synthesis of a novel triazine flame retardant containing sulfur and its application to cotton fabrics

A novel triazine flame retardant (FR) has been successfully synthesized by the reaction of cyanuric chloride with sodium sulfanilate followed by diethanol amine. Its structure has been fully characterized by IR and 1H NMR spectroscopy. The effects of reaction solvent, acid-binding agent, reaction temperature, and molar ratio of starting materials on the yield of FR were investigated in detail. Experiments showed that when the molar ratio of intermediate I to diethanol amine is 1 to 1.2 in the presence of sodium carbonate as acid-binding agent in acetone-water at 45 °C, the yield of the obtained FR reaches 81.4%. Thermogravimetry (TG) test indicated that the FR has good thermostability and char-forming ability. In addition, the flame retardancy and thermal behavior of the cotton fabrics treated with FR were studied by limiting oxygen index (LOI), vertical flammability test, and thermogravimetry (TG) to evaluate the flameretardant performance of the target FR. These results demonstrated that the flame retardancy and thermal stability of the cotton fabrics treated with FR were clearly improved.

Synthesis of novel dopamine derived multidirectional ligands from cyanuric chloride: structural and antimicrobial studies.

Two monopodal (2,4-dichloro-6-(3-hydroxytyramine)-1,3,5-triazine) and tripodal (2,4,6-(3-hydroxytyramine)-1,3,5-triazine) s-triazine derivatives were prepared through the reaction of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) and 3-hydroxytyramine hydrochloride (dopamine hydrochloride). The structures of the compounds were identified by FT-IR, 1H NMR, 13C NMR, thermal analysis and elemental analysis. Their antimicrobial activities were carried out using the broth microdilution method in dimethyl sulfoxide (DMSO): Phosphate Buffered Saline (PBS) against eight bacteria and one yeast. The results of the test were compared with ampicillin. It was determined that CCDOP1, CCDOP3 and DOP have significant antibacterial and antifungal activity. These three chemicals revealed strong antibacterial activity against the E. coli and S. aureus strains used in the study. S. aureus was the most sensitive strain against dopamine hydrochloride and E. coli was the most sensitive bacteria against CCDOP1.

N-Triazinyl Derivatives of 1- and 9-aminoanthracene: Synthesis and Photo-Physical Properties

New N-triazinyl derivatives were synthesized by reaction of cyanuric chloride with 1- and 9-aminoanthracenes and subsequent nucleophilic substitution of chlorine atoms on triazinyl ring with methoxy and/or phenylamino groups. The compounds were characterized by (1)H and (13)C NMR and mass spectra. The influence of the chemical structure and solvent polarity on the UV/Vis absorption and fluorescence spectra and fluorescence quantum yields were investigated. Semi-empirical computations revealed highly polar CT states in singlet excited state manifold connected with charge-transfer from the hydrocarbon moiety to the triazinyl ring. The relationships between the CT-to-emitting state energy gap, solvent polarity and fluorescence quantum yield were discussed.

Synthesis and Properties of the Composite DSD Acid-Triazine Structure Containing Long-Chain Quaternary Ammonium Fluorescent Brighteners

The cetyl \ octadecyl dimethyl tertiary amine（percentage composition 7:3）is a very common and inexpensive chemical raw material in the chemical market. In this paper, a series of the new chemical composite DSD acid-triazine structure containing long chain quaternary ammonium salt fluorescent brighteners (FBs) were synthesized through a three-step condensation reaction of cyanuric chloride, DSD acid, cetyl \ octadecyl dimethyl tertiary amine and amino compound. The obtained compounds were characterized by the analysis of the IR spectrum, UV spectrum and fluorescence excitation and emission spectrum, and whiteness were tested through dyeing filter paper. The results show that compounds 7a-j have the obvious UV absorption, fluorescence emission and dyeing properties, with a wider absorption, emission wavelength range and enhancing fluorescence quantum yield, achieving the synergetic enhancement effect by compounding.

New highly conductive organic–inorganic hybrid electrolytes based on star-branched silica based architectures

A new type of organic–inorganic hybrid electrolyte has been developed by a sol–gel process through the reaction of cyanuric chloride with poly(oxyalkylene) diamine and 3-isocyanatepropyltriethoxysilane, followed by co-condensation of 2-[methoxy(polyethyleneoxy)propyl]trimethoxysilane. A maximum ionic conductivity of 1.0 × 10−4 Scm−1 at 30 °C has been achieved with the solid hybrid electrolyte. The results of solid-state NMR not only confirm the structural framework of the hybrids, but also provide a microscopic view of the effects of salt concentrations on the dynamic behavior of the polymer chains. The hybrid materials are blended with PVdF-HFP to form the blend hybrid membrane, followed by plasticization with various electrolyte solvents, with the purpose of increasing ionic conductivity. The plasticized blend hybrid electrolyte exhibits a maximum room temperature ionic conductivity of 8.8 × 10−3 Scm−1. Such a high ionic conductivity allows it as a potential candidate for applications in lithium ion batteries.

A Mild and Efficient Route to 2-Azetidinones Using the Cyanuric Chloride-DMF Complex

Efficient conversion of Schiff bases and carboxylic acids to β-lactams can be carried out at room temperature in CH2Cl2, using a cyanuric chloride-N,N-dimethyl formamide complex. The complex is easily prepared by reaction of cyanuric chloride and DMF, an inexpensive reagent, at room temperature. Optimization of conditions and comparison of yield with cyanuric chloride were performed.

First structurally characterized triazinyl palladium complexes via oxidative addition of cyanuric chloride derivatives

The reaction of cyanuric chloride and two disubstituted derivatives with [Pd(PPh 3) 4] is described, leading to the trans-triazinyl complexes [(PPh 3) 2Pd(C 3N 3R 2)Cl] 2a–c (R = Ph ( a), t-Bu ( b), Cl ( c)) in good to excellent yield via oxidative addition. The complexes were fully characterized including X-ray structure determination.