Reaction Of Cyanuric Chloride Research Articles

2-Alkyl-4,6-dialkylamino-1,3,5-triazines via Grignard Alkylation of Cyanuric Chloride: An Aged Reaction Revisited

Suitable one-pot reaction conditions are suggested to prepare, in good overall yields, some 2-(alk-1′-ynyl)- and 2-alkyl-4,6-dialkylamino-1,3,5-triazines via reaction of cyanuric chloride with Grignard reagents followed by amination.

Effect of Triazine Dithiols on the Polymer Plating of Magnesium Alloys

2- Substituted (R)-1,3,5- triazine-4,6-dithiols (triazine dithiols ) with different alkyl chain lengths as substituents were prepared by the reaction of cyanuric chloride, dialkylamines and NaSH. Triazine dithiols were found to polymerize electrochemically on magnesium alloy (AZ91) plates. This method for coating metals is called polymer plating In the polymer plating of triazine dithiols on magnesium alloy plates, an aqueous 1M-NaOH solution was selected for the formation of polymer films and the suppression of side reactions. To select the optimal conditions for the formation of polymer films and the suppression of side reactions, plating factors such as the electrolyte, temperature, concentration, potential and current density were investigated. The films formed were composed of a polymer film, Mg(OH)2 and MgO, and the chemical structure of the films is discussed. The contact angle of the polymer films increased with the length of the alkyl chain and became constant for a chain length of six carbons. Polymer films with a 98° contact angle had a top surface completely covered all by CH3 - groups and not by - CH2- The alkyl chains were oriented in the vertical direction and were closely packed. Among the five polymer films studied real impedance (Rp) was the largest at about 27,000 Ω cm -2 - for the polymer film with a (C6H13)2N- subustituent The icorr of this polymer film was 5x 10 -7 A cm -2 2 The outstanding corrosion resistance of polymer film with a (C6H13)2N-subustituent is thought to result from the alkyl chains in the film that were highly oriented and closely packed.

Liquid crystalline 1,3,5-triazines incorporating rod-like azobenzene sub-units

New liquid crystalline 1,3,5-triazines are presented that incorporate three mesogenic groups based on rod-like azobenzene moieties. The synthesis was carried out by reaction of cyanuric chloride with 4-alkoxy-4-aminoazobenzene derivatives. The mesomorphic behaviour was investigated by polarizing microscopy, differential scanning calorimetry and X-ray scattering. Besides a nematic and a SmA phase, the trisazomelamines form a higher ordered mesophase within a broad temperature range below the smectic A phase. With respect to the rod-like azobenzene sub-units, the low temperature phases display a smectic 'bilayer' structure. The molecules are antiparallel aligned within one layer. Furthermore, 1,3,5-triazines incorporating just two azobenzene groups are presented, these were prepared to investigate the influence of the number of rod-like sub-units linked to the triazine core on the mesomorphic properties.

New disc-shaped triarylamino-1,3,5-triazines with heteroaromatic central cores

Abstract New disc-shaped triarylamino-1,3,5-triazines were prepared by reaction of cyanuric chloride with two-fold alkoxy substituted anilines. Each of the triarylmelamines exhibits an enanti-otropic mesophase. X-ray investigations reveal the formation of columnar liquid crystalline structures with either a hexagonal or a rectangular lattice. The lattice parameters, as well as the intracolumnar ordering, depend on the length of the flexible lateral side chains. The new melamines form Langmuir monolayers at the air/water interface due to their amphiphilic nature. The monolayer organization is characterized by a side-on arrangement of the molecules. The polar central molecular parts lie flat on the water, whereas the lateral alkyl chains are oriented perpendicular to the water surface.

Multifunctional Zwitterion-Exchange Stationary Phase for HPLC

Abstract A zwitterion-exchange stationary phase (ZIXSP) was prepared for the separation of the mixture of organic bases, organic acids and amino acids by high performance liquid chromatography (HPLC). It was synthesized by the reaction of cyanuric chloride with sulfanilic acid and then bonded onto the silica gel on which the silane coupling agent was prebonded. The chromatographic behaviours of the prepared ZIXSP revealed that the capacity factors of each analyte varied with the pH value of the mobile phase. By applying the concept of acid-base equilibrium the correlation between the capacity factor on the ZIXSP and pH of the mobile phase could be explained reasonably. Based on our results, it is concluded that ZIXSP is a zwitterion exchanger that additionally provides π-π charge-transfer interaction and hydrophobic interaction functions.

Kinetic studies on the Reaction of Cyanuric Chloride with Amines

The individual steps in the reactions of cyanuric chloride with n-butyl amine in N-methyl pyrrolidone (NMP) and with morpholine in isopropanol (i-PrOH) were followed kinetically. The ratio of the exchange rates of the first, the second and the third chlorine atom was unexpectedly high in both cases. The reactions of n-butylamino dichlorotriazine with several amines were studied kinetically both in NMP and in i-PrOH. Linear free-energy relationships exist both between our values in NMP and in isopropanol and between our values and reaction rates of p-nitro fluorobenzene with the corresponding amines (in DMSO) determined by Suhr.

Synthesis of a New Trialdehyde Template for Molecular Imprinting

A recent approach in the area of molecular recognition involves template-assisted imprinting' of the surface of rigid polymers such as silica gel. Siloxy-Schiff bases of structurally rigid dialdehydes have been used as templates to introduce two appropriately spaced amino groups for substrate binding on the solid surface. The distance between the two amino groups is defined by the structure of the dialdehydes. Moderate selectivity has been reported in rebinding of the dialdehydes to the modified surface.2 Current objectives in this quest involve the development of multidentate template molecules to expand the repertoire of functional groups available a t the binding sites3 We report herein the synthesis of a trialdehyde and its Schiff bases as a new template for molecular imprinting of solid surfaces. The reaction of cyanuric chloride with 3 equiv of p hydroxybenzaldehyde in benzene gave the desired trialdehyde, TRIPOD (1) (Scheme 11, in a single step. Trialdehyde 1 was then reacted at room temperature with (aminopropy1)triethoxysilane (APTES) or p-(methoxydimethylsily1)aniline (MODSA)4 to afford the corresponding silane-TRIPODS, APTES TRIPOD (2), and MODSA TRIPOD 4 (Scheme 2), respectively. Model compounds PROPYL TRIPOD (3) and ANILINE TRIPOD (5) were also synthesized for future mechanistic studies of Schiff base formation. Acid hydrolysis of all the Schiff bases regenerated the intact TRIPOD. Molecular imprinting was carried out with silaneTRIPOD molecules 2 and 4 on silica gel to yield modified silicas 7 and 8, respectively. Porous silica gel, Fractosil 500, was refluxed in dry toluene for 2 days28 with an appropriate amount of the silane-TRIPODS to get a low substitution level on the silica and ensure site isolation (Scheme 3). Initial experiments with APTES TRIPOD (2) indicated that a partial degradation of 2 took place during the imprinting reaction. Refluxing of the model compound 3 in toluene for 2 days produced p-hydroxybenzaldehyde, suggesting that the degradation was caused by the partial hydrolysis of the Schiff base and subsequent attack on the ether linkage by the amine. On the other hand, MODSA TRIPOD (4) did not decompose, presumably due to the greater strength of the aromatic Schiff

Tris(Dialkylamino)-s-Triazines, Characterization and Thermal Properties

Several Tris(dialkylamino)-s-triazines were prepared by reaction of cyanuric chloride with the appropriate secondary amines. Some of their properties are reported.

Syntheses of 2,4,6-tris(di-tetrahydrofurfuroxy)phosphinyl-s-triazine and its derivatives as fire-retardants for cellulose

The synthesis of 2,4,6-tris(di-tetrahydrofurfuroxy)phosphinyl-s-triazine (2) was achieved by the reaction of cyanuric chloride with tris(tetrahydrofurfuryl)-phosphite (1) or with sodium bis(tetrahydrofurfuryl)phosphite (5). 2 on treatment with anhydrous ammonia yielded ammonium salt of 2,4-diamino-6-tetrahydro-furfuroxy-phosphinyl-s-striazine (3), which on methylolation yielded (4). The reaction of 2 and 4 with cellulose powder under different experimental conditions was carried out and they were found to exhibit promising fire-retardant properties.

Reaction of cyanuric chloride and its derivatives with polyamide fibres in non‐aqueous medium

AbstractPolyamide fibres (Nylon 6) were treated with cyanuric chloride in organic solvents (tetrachloroethylene and xylene) under different conditions. This treatment caused an increase in the fibre nitrogen content. The magnitude of the latter was dependent upon the cyanuric chloride concentration, the time and temperature of the treatment as well as the nature of solvent. For instance an extra nitrogen content of 0.08% was obtained at a cyanuric chloride concentration (based on wt. of fabric) of 25%. This contrasts with 0.46% at 100% concentration of cyanuric chloride. Similarly and extra nitrogen content of 0.08% was achieved at 50°C while at 121°C it amounted to 1.18%. However, the cyanuric chloride treated nuylon failed to link covalently to dyestuffs containing labile hydrogen, indicating no chemical reaction between polyamide 6 and cyanuric chloride. This chemical reaction could only be achieved by use of 2‐anilino‐4,6‐dichloro‐1,3,5‐triazine instead of cyanuric chloride. Similarly a disperse dye containing a chlorotriazine ring as the reactive group was found to react chemically with polyamide 6.

S-Triazines. 1. Reaction of cyanuric chloride with unsaturated nitrogen compounds

s-Triazines. 1. Reaction of cyanuric chloride with unsaturated nitrogen compounds

Derivatives Of ditraizinylamine and tritriazinylamine

Abstract2‐Arylamino‐4,6‐dichloro‐s‐triazine reacts with cyanuric chloride in the presence of alkali to yield N,N‐bis(4,6‐dichloro‐s‐triazin‐2‐yl)‐arylamine. In like manner, 2‐substituted o‐chloro‐, p‐chloro‐, o‐nitro‐ and p‐carbomethoxyphenylamino‐4,6‐dimethoxy‐s‐triazines react with cyanuric chloride to yield the corresponding 4,6‐dichloro‐s‐triazin‐2‐yl‐4′,6′‐dimethoxy‐s‐triazin‐2′‐ylaryl‐amine, while anilino‐, p‐toluidino, o‐ and p‐methoxyphenylamino and o‐carbomethoxyphenylamino derivatives did not.The reaction of cyanuric chloride with 2,4‐dichloro‐6‐ethylamino‐s‐triazine in the presence of alkali yields the condensation product of the ditriazinylamine type and the reaction of cyanuric chloride with ammonia yields N,N‐bis(4,6‐dichloro‐s‐triazin‐2‐yl)‐ or tris(4,6‐dichloro‐s‐triazin‐2‐yl)amine.

1,3,5-Triazines. Part XI. Reaction mechanisms and solvent effects in the reactions of cyanuric chloride with NN-diethylaniline and NN-diethyl-1-naphthylamine

The effect of a variety of aprotic solvents on the extent of the reaction and the composition of the products in the reactions between cyanuric chloride and NN-diethylaniline or NN-diethyl-1-naphthylamine has been investigated. Increasing polarity of the solvent increases the reaction rate and favours ‘nitrogen-’ at the expense of ‘carbon-substitution’. Under all conditions investigated the ratio of ‘carbon-’ to ‘nitrogen-substitution’ is greater for the naphthylamine than the aniline. The formation of a coloured 1 : 1 charge-transfer complex between the tertiary arylamine and cyanuric chloride is shown to be a necessary, but not sufficient, condition for ‘carbon-substitution’. The stability constants for the complexes with the above two amines as well as for the three NN-diethyltoluidines have been evaluated. The reaction mechanisms for ‘carbon-’ and ‘nitrogen-substitution’ are discussed.

The reaction of cyanuric chloride with methylenephosphoranes

The reaction of cyanuric chloride with methylenephosphoranes

1,3,5-Triazines. Part VIII. The reactions of cyanuric chloride with NN-dialkylnaphthylamines and O-alkyl naphthyl ethers

The reactions of cyanuric chloride with NN-dimethyl-, NN-diethyl-and NN-diethyl-2-methyl-1-naphthylamines have been investigated. Two types of products were obtained, N-alkyl-N-(1-naphthyl) aminodichloro-1,3,5-triazines and 4′-(NN-dialkylamino-1-naphthyl)dichloro-1,3,5-triazines. NN-Diethyl-2-naphthylamine under comparable conditions gave three products, N-ethyl-N-(2-naphthyl)aminodichloro-1,3,5-triazine, bis-(N-ethyl-N-2′-naphthylamino)chloro-1,3,5-triazine, and (2-NN-diethylamino-1-naphthyl)dichloro-1,3,5-triazine. This reaction has given the first, and so far only, example of the triazine electrophile entering an aromatic ring at any position other than para to the dialkylamino-group. This type of reaction which up to now has been confined to tertiary arylamines is now extended to O-alkyl naphthyl ethers. The latter require much higher temperatures for reaction, and give exclusively nuclear substituted products. The factors influencing the relative proportions of the compounds obtained are discussed. The determination of the structures by means of i.r., u.v., and 1H n.m.r. spectroscopy is described.

塩化シアヌルとシアン酸カリウムの反応

塩化シアヌルとシアン酸カリウムの反応

Polycondensats Linéaires Obtenus à Partir de Monomères Triaziniques

AbstractDichlorotriazinic monomers prepared by the reaction of cyanuric chloride with an amine or a Grignard reagent are polycondensed with bisphenols as well as with diamines. Linear polymers thus obtained an analyzed and identified and their physical constants have been determined. Particularly, their behaviour towards heat, solubility, molecular weight, cristallinity and IR absorption spectra have been examined.

The synthesis and characterization of some 2,1,6‐triaryl and alkylsulfonylhydrazido‐s‐triazines

Abstract2,4,6‐Trialkyl‐ and triarylsulfonylhydrazido‐s‐triazines (I) have been synthesized by the reaction of cyanuric chloride with a variety of sulfonylhydrazides in a hydrocarbon solvent. The subject compounds (I) were characterized by elemental analysis, molecular weight and spectroscopy.

The reaction of cyanuric chloride with gelatins and animal glues

The reaction of cyanuric chloride with gelatins and animal glues

1011. 1,3,5-Triazines. Part V. The reactions of cyanuric chloride with NN-dialkyl-anilines, -toluidines, and -xylidines

1011. 1,3,5-Triazines. Part V. The reactions of cyanuric chloride with NN-dialkyl-anilines, -toluidines, and -xylidines