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CAS number(s): 4719-04-4
Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a formaldehyde condensate product that is used as an antimicrobial agent in metal working fluids. Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a low to moderate hazard material and risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low to moderate
1,3,5-Triazine-1,3,5(2H,4H,6H)-Triethanol, Kalpur te, 1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine, Miliden X-2, Grotan BK, N,N'N' -Tris(beta-hydroxyethyl)hexahydro-1,3,5-triazine, Hexahydro 1,3,5-(2-hydroxyethyl)-s-triazine, Onyxide 200, Hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine, Triazine-1,3,5(2H,4H,6H)-triethanol, Hexahydro-1,3,5-tris(2-Hydroxyethyl)triazine, Tris(2-hydroxyethyl)hexahydrox-s-triazine, Hexahydro-1,3,5-triazine-1,3,5-triethanol, Trishydroxyethyl-s-hexahydrotriazine; 1,3,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine; 1,3,5-triazine-1,3,5(2h,4h,6h)-triethanol; HEXAHYDRO-1,3,5-TRIS(2-HYDROXYETHYL)-TRIAZINE; HEXAHYDRO-1,3,5-TRIS(HYDROXYETHYL)-S-TRIAZINE; HEXAHYDRO-1,3,5-TRIS(HYDROXYETHYL)TRIAZINE; 2,2’,2’’-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol; Triethanol = Hexahydro - 1,3,5, - Tri - Hydroxyethyl - S-Triazine; s-Triazine-1,3,5-triethanol; 1,3,5-TRI-(2-HYDROXYETHYL)-HEXAHYDRO-1,3,5-TRIAZINE; 2,2',2''-(1,3,5-Triazinane-1,3,5-triyl)triethanol; 2,2',2''-(1,3,5-Triazinane-1,3,5-triyl); triethanol; HEXAHYDRO-1,3,5; 1,3,5-Tris(2-hydroxyethyl)-1,3,5-triazacyclohexane; Hexahydro-1,3,5-tri(2-hydroxyethyl)-s-triazine; N,N',N''-Tris(2-hydroxyethyl)hexahydro-s-triazine; N,N',N''-Tris(β-hydroxyethyl)hexahydro-s-triazine; s-triazine-1,3,5(2h,4h,6h)-triethanol; 1,3,5-tris-(2-Hydroxyethyl)hexahydro triazine; Trizin; Triadine10; 1,3,5-Tris(2-hydroxyethyl) hexahydro-s-triazine ;Hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine; Hexahydrotriazine; N,N,N-TRIS(HYDROXYETHYL)-HEXAHYDRO-TRIAZINE; HEXAHYDRO-1,3,5-TRIS(HYDROXYETHYL)TRIAZIN; 2,2′,2′′-(Hexahydro-1,3,5-triazin-1,3,5-triyl)triethanol; Triazine-1,3,5(2H,4H,6H)-triethanol, s-: (Onyxide 200)); 2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol 1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine; 1,3,5-Triazine-1,3,5(2H,4H,6H)-tris(ethanol); 2,2',2''-[1,3,5-Triazine-1,3,5(2H,4H,6H)-triyl]triethanol; Hexahydro-1,3,5-triazine-1,3,5-triethanol; Hexahydro-s-triazine-1,3,5-trisethanol; Tris-(b-hydroxyethyl)-hexahydrotriazin, 1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine, 2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol; Hexahydro-1,3,5-tris-(2-hydroxyethyl)-1,3,5-triazine; 1,3,5-Triazine-1,3,5(2H,4H,6H)-triethanol; s-Triazine-1,3,5-triethanol; Hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine; Hexahydro-1,3,5-tris(hydroxyethyl)triazine; 1,3,5-Tris(hydroxy-ethyl)s-hexahydrotriazine; 1,3,5-Tris(2-hydroxyethyl)hexahydro-s-triazine; tris(N-hydroxyethyl) hexahydrotriazine; 1,3,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine; s-Triazine-1,3,5(2H,4H,6H)-triethanol; 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol; 2,2',2''-(Hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol; Tris-hydroxyethyl-hexahydro-S-triazine; Hexahydro-1,5-tris(hydroxyethyl)triazine; s-Triazine-1,5(2H,4H,6H)-triethanol; Hexahydro-1,5-tris(2-hydroxyethyl)triazine; 1,3,5-tris-hydroxyethyl perhydro-s-triazine; 1,5-Tris(2-hydroxyethyl)hexahydro-s-triazine; Hexahydro-1,3,5-triazine-1,3,5-triethanol; Hexahydro-1,3,5-tris(2-hydroxyethyl)triazine; 1,3,5-tris(2-Hydroxyethyl)perhydro-s-triazine; 1,5-Triazine-1,3,5(2H,4H,6H)-triethanol; Hexahydro-1,5-tris(2-hydroxyethyl)-s-triazine; 1,3,5-Tris(2-hydroxyethyl)perhydro-s-tria-zine; Hexahydro-1,5-tris(2-hydroxypropyl)-s-triazine; 1,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine; 1,3,5-tris-(2-hydroxyethyl)-1,3,5-hexahydrotriazine; Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine, 74% solution in water
N,N',N"‐Tris(β‐hydroxyethyl)‐hexahydro‐1,3,5‐triazine (THT) is present in numerous products with very different names (Bacillat 35, Bakzid 80, Dehygant LFM and M 45, Mergal KM 200, Grotan BK, Glokill 77, Forcide 78, etc.) [3] and also the product called Grotan BK, with which almost all the data described in this review were obtained (see footnote on first page), appears in the literature as "Grotan Konz. BK" or "conc. BK" or even just "Grotan". THT is generally added to metal‐working fluids (grinding emulsions, etc.) in a final concentration of 0.15 − 0.2 %. There is no data available about breakdown products – especially at high temperatures – or reactions with other components of the emulsions.
General Statement Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a light-yellow liquid. It is a formaldehyde condensate product that is used as an antimicrobial agent in metal working fluids. Ashland both purchases and produces this chemical. Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a low to moderate hazard material and the risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low to moderate. Exposure controls in the workplace serve to prevent adverse health effects to workers. This material is not directly sold to consumers and has no known intended use in consumer products. Therefore, consumer exposure and subsequent risk associated with such exposure is unlikely.
Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a formaldehyde condensate product that is used as an antimicrobial agent in metal working fluids. Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a low to moderate hazard material and risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low to moderate"
Although triazines are aromatic compounds, their resonance energy is much lower than in benzene. Electrophilic aromatic substitution is difficult but nucleophilic aromatic substitution easier than typical chlorinated benzenes. 2,4,6-Trichloro-1,3,5-triazine is easily hydrolyzed to cyanuric acid by heating with water. 2,4,6-Tris(phenoxy)-1,3,5-triazine results when the trichloride is treated with phenol. With amines, one or more chloride is displaced. The remaining chlorides are reactive, and this theme is the basis of the large field of reactive dyes.
Cyanuric chloride assists in the amidation of carboxylic acids.
The 1,2,4-triazines can react with electron-rich dienophiles in an inverse electron demand Diels-Alder reaction. This forms a bicyclic intermediate which normally then extrudes a molecule of nitrogen gas to form an aromatic ring again. In this way the 1,2,4-triazines can be reacted with alkynes to form pyridine rings. An alternative to using an alkyne is to use norbornadiene which can be thought of as a masked alkyne.
In 2007, a method for synthesizing highly porous triazine-based polymers was discovered, and found to be useful (in conjunction with palladium) for the selective reduction of phenols
A series of 1,2,4-triazine derivatives known as bis-triazinyl bipyridines (BTPs) have been considered as possible extractants for use in the advanced nuclear reprocessing. BTPs are molecules containing a pyridine ring bonded to two 1,2,4-triazin-3-yl groups.
Triazine-based ligands have been used to bind three dinuclear arene ruthenium (or osmium) compounds to form metallaprisms.
The more common 1,3,5-isomers are prepared by trimerization of nitrile and cyanide compounds, although more specialized methods are known.
The 1,2,3- and 1,2,4-Triazines are more specialized methods. The former family of triazines can be synthesized by thermal rearrangement of 2-azidocyclopropenes. Also mainly of specialized interest, the 1,2,4-isomer is prepared from condensation of 1,2-dicarbonyl compounds with amidrazones. A classical synthesis is also the Bamberger triazine synthesis.
A well known triazine is melamine (2,4,6-triamino-1,3,5-triazine). With three amino substituents, melamine is a precursor to commercial resins. Guanamines are closely related to melamine, except with one amino substituent replaced by an organic group. This difference is exploited in the use of guanamines to modify the crosslinking density in melamine resins. Some commercially important guanamines are benzoguanamine and acetoguanamine.
Another important triazine is cyanuric chloride (2,4,6-trichloro-1,3,5-triazine). Chlorine-substituted triazines are components of reactive dyes. These compounds react through a chlorine group with hydroxyl groups present in cellulose fibres in nucleophilic substitution, the other triazine positions contain chromophores. Triazine compounds are often used as the basis for various herbicides.
Triazines also have wide use in the oil and gas and petroleum processing industries as a non-regenerating sulfide removal agent; they are applied to fluid streams to remove hydrogen sulfide gas and mercaptan species, which can decrease the quality of the processed hydrocarbon and be harmful to pipeline and facility infrastructure if not removed
1,3,5-triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.
[1,3,5]-Triazine derivatives have traditionally found applications in analytical chemistry as complexation agents, in electrochemistry as multi-step redox systems and as pesticide or herbicide components in agriculture. In the last years, there has been a growing interest in these compounds that have been used, for example, as templates in multidimensional crystal engineering involving metal complexes for producing nanometre sized oligonuclear coordination compounds, as scaffold in combinatorial chemistry and even as new building blocks in peptidomimetics. The continuous demand to develop synthetic methods for the selective preparation of compounds, under mild conditions and by using non-toxic and not expensive reagents, has prompted the researchers to investigate the use of [1,3,5]-triazine derivatives, such as cyanuric chloride and trichloroisocyanuric acid in organic synthetic applications. For this reason cyanuric chloride, and its derived reagents, are used as dehydrating agents in organic synthesis, as coupling agents in the synthesis of peptides, in the preparation of esters, amides, alkyl chlorides, acyl azides, in the selective protection of hydroxyl groups and so on.
From this point of view, this reagent appears as a cheap reactive for many group transformations. 1,3,5-Triazine derivatives are versatile reagents even in the oxidation reactions, such as in Swern type process, and in other important oxidation procedures. In this context, another [1,3,5]-triazine derivative such as trichloroisocyanuric acid, which can be conveniently used even in halogenation reactions, can perform efficient oxidations of alcohols. [1,3,5]-Triazine compounds have been employed both as reagents and intermediates in the synthesis of heterocycles and even as “combinatorial core” for the design of new therapeutics.
Symmetrical 1,3,5-triazines are prepared by trimerization of certain nitriles such as cyanogen chloride or cyanimide. Benzoguanamine (with one phenyl and 2 amino substituents) is synthesised from benzonitrile and dicyandiamide. In the Pinner triazine synthesis (named after Adolf Pinner)[3] the reactants are an alkyl or aryl amidine and phosgene. Insertion of an N-H moiety into a hydrazide by a copper carbenoid, followed by treatment with ammonium chloride also gives the triazine core.
Triazine chemistry has many applications from industrial usage, such as melamine resins, to academic interests in dendritic structures which may one day come to fruition as pharmaceutically applicable molecules. Organic synthesis, using the 1,3,5- triazine derivative 2,4,6-trichlorotriazine, cyanuric chloride, for practical applications was investigated. By utilizing the selective reactivity of cyanuric chloride, a plethora of targets from small molecules to large dendrimers may be synthesized. Triazine chemistry was adapted to an educational application for the development of an undergraduate laboratory to synthesize simazine, a widely used herbicide. The laboratory was designed to foster a sense of the applications of chemistry in the world and its effect on the environment and society. The modification of chitosan for herbicide remediation has been accomplished using triazine chemistry, as well. Treatment of chitosan iteratively with cyanuric chloride followed by piperazine produces dendritic grafts from these flakes. Dendrons of generation one through three were synthesized on chitosan backbones of low, medium, and high molecular weights. The piperazine derivatives were shown to sequester more than 99% of atrazine from an aqueous 100 ppb solution in a 24 h period. Drug delivery applications of triazine-based dendrimers were investigated. Pegylated G3 dendrimers with molecular weights of 18 and 34 kDa with 9% and 17% iodine content by weight, respectively, were synthesized as potential macromolecular contrast agents. The development of macromolecular contrast agents is of great interest to counteract the drawbacks associated with currently used, small molecule contrast media, including toxicity, extravasation into the extracellular space, and rapid clearance from the bloodstream. Dendrimers are well suited for use as macromolecular media due to the unique properties of these molecules, including monodispersity and multivalency.
As a reagent in organic synthesis, s-triazine is used as the equivalent of hydrogen cyanide (HCN). Being a solid (vs a gas for HCN), triazine is sometimes easier to handle in the laboratory. One application is in the Gattermann reaction, used to attach the formyl group to aromatic substrates
Triazine Biocide can be dissolved in deionized water and standard hard water (3mmol Ca ion/l) in any proportion, soluble in water alcohol and propylene glycol.
Triazine biocide uses hexahydro-1,3,5-tris (hydroxyethyl) himetriazine as the main active ingredient. It is a broad-spectrum, high-efficiency, low-toxic antiseptic and mildew fungicide.
Triazine can act alone or in combination with other active ingredients. Triazin can be used alone or in combination with other fungicides. It is mainly used in oil industry, paper industry, metal processing industry (cutting fluid, grinding fluid, rolling fluid), coating industry and electroplating industry
Application range:
Papermaking Industry:
Instructions: It can be used in the mixing tank, the slurry pool, the high overflow box, the thickener and the white pool in front of the pulp machine. It can reduce fiber degradation and increase paper strength. Depending on the process, continuous drip or impact dosing can be used.
Oil Field Industry:
Instructions: It can be used for anti-corrosion sterilization of drilling mud, completion fluid, fracturing fluid, cementing agent and fluid loss additive. Depending on the process, continuous drip or impact dosing can be used.
Preservation of industrial technology products:
Such as metalworking fluids, metal surface treatments in the electroplating industry, binders, industrial additives, polymer dispersants and lubricants.
Features:
1. high efficiency, broad spectrum, with the dual role of inhibition and sterilization.
2. The compatibility is good, it does not affect the physical properties such as the color and strength of the paper, and it has no corrosion to the equipment.
3. Triazine is effective in a large pH range and can maintain long-term stable activity.
4. The amount of addition is small, the effect is fast, and the bactericidal power is strong.
5. environmentally friendly “green product”
Chemical Identity
Name: Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine
Brand Names: Not applicable
Chemical name (IUPAC): 2,2',2''-(1,3,5-triazinane-1,3,5-triyl)triethanol
EC number: 225-208-0
Molecular formula: C9H21N3O
Uses and Applications
Hexahydro-1,3,5-tris-(-2-hydroxyethyl)-s-triazine is a product that is used for the formulation of antimicrobial products for use in metalworking cutting fluids, gas/oil drilling muds/packer fluids and industrial adhesives.Grotan BK is a triazine derivative contained in cutting fluids. It is a formaldehyde releaser. Hexahydro-l,3,5-tris-(2-hydroxyethyl)triazin is used in organic synthesis; as a bactericide in cooling fluids and various cosmetic products; formaldehyde liberator.
Reactivity Profile
Hexahydro-1,3,5-tris(hydroxyethyl)-s-triazine is an amine and an alcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
All other petroleum and coal products manufacturing
Fabricated metal product manufacturing
Oil and gas drilling, extraction, and support activities
Paper manufacturing
Petrochemical manufacturing
Petroleum lubricating oil and grease manufacturing
Petroleum refineries
Plastic material and resin manufacturing
Triazine is the six-membered heterocyclic ring containing three nitrogens, which replace the carbon-hydrogen unit in the benzene ring. Based on nitrogen position present in the ring system, it is categorized in three isomeric forms, i.e., 1, 2, 3-triazine (vicinal triazine), 1, 2, 4-triazine (asymmetrical triazine or isotriazine) and 1, 3, 5-triazine (symmetrical or s-triazine or cyanidine). Triazines have a weakly basic property. Their isomers have much weaker resonance energy than benzene structure, so nucleophilic substitution reactions are more preferred than electrophilic substitution reactions. Triazine isomers and their derivatives are known to play important roles possessing various activities in medicinal and agricultural fields such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal, antimalarial and antimicrobial agents.
Any of several related compounds or a mixture thereof. A liquid or solid dissolved in a liquid carrier; the carrier is water emulsifiable (Farm Chemicals Handbook p. C145, 1995). Toxic by inhalation, skin absorption and/or ingestion. The primary hazard is the flammability of the carrier. Obtain the technical name of the material from the shipping paper and contact CHEMTREC, 800-424-9300 for specific response information.
Liquid, poisonous appears as a colorless to tan crystalline solid dissolved in a water-emulsifiable organic carrier. Carrier may burn though may be difficult to ignite. Toxic by inhalation, skin absorption or ingestion.
Triazine pesticide, solid, poisonous appears as a colorless to tan solid formulated as a wettable powder. Toxic by inhalation, skin absorption or ingestion.
HEXAHYDRO-1,3,5-TRIS(HYDROXYETHYL)-5-TRIAZINE is an amine and an alcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to <100 000 tonnes per annum.
This substance is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Biocidal Uses
This substance is being reviewed for use as a biocide in the EEA and/or Switzerland, for: product preservation, preservation for liquid systems, controlling slimes, preservation for working / cutting fluids.
Formulation or re-packing
This substance is used in the following products: pH regulators and water treatment products.
Release to the environment of this substance can occur from industrial use: formulation of mixtures and of substances in closed systems with minimal release.
Uses at industrial sites
This substance is used in the following products: oil and gas exploration or production products, pH regulators and water treatment products and fuels.
This substance is used in the following areas: mining and formulation of mixtures and/or re-packaging.
This substance is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: of substances in closed systems with minimal release, as processing aid, manufacturing of the substance, in processing aids at industrial sites and formulation of mixtures.
Manufacture
Release to the environment of this substance can occur from industrial use: manufacturing of the substance, of substances in closed systems with minimal release, in processing aids at industrial sites and as processing aid.
IUPAC Names
1,3,5-Triazine-1,3,5(2H,4H,6H)-triethanol
1,3,5-triazine-1,3,5(2H,4H,6H)-triethanol
1,3,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine
1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine
1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine 2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2"-(1,3,5-triazinane-1,3,5-triyl)triethanol
2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2"-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol;
2,2',2''-(1,3,5-triazinane-1,3,5-triyl)triethanol
2,2',2''-(HEXAHYDRO-1,3,5-TRIAZINE-1,3,5-TRIYL)TRIETHANOL
2,2',2''-(Hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2''-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2''-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2,2',2''-(hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol (IUC4 D SN 432) / 2,2',2''-(1,3,5-triazinane-1,3,5-triyl)triethanol / HHT
2,2',2''-(Hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol; 1,3,5-tris(2-hydroxyethyl)hexahydro-1,3,5-triazine
2,2,2"-(Hexahydro-1,3,5-triazine-1,3,5-triyl)triethanol
2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethan-1-ol
2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol
2-[4,6-bis(2-hydroxyethyl)-1,3,5-triazinan-2-yl]ethanol
S-TRIAZINE-1,3,5(2H,4H,6H)-TRIETHANOL
Triadine 10
Trade Names
1,3,5-Triazine-1,3,5(2H,4H,6H)-triethanol (9CI)
1,3,5-Tris(2-hydroxyethyl)hexahydro-1,3,5-triazine
1,3,5-Tris(2-hydroxyethyl)hexahydro-s-triazine
1,3,5-Tris-(2-hydroxyethyl)-1,3,5-hexahydrotriazine (chemical name)
Grotan
Hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine
Hexahydrotriazine
Hexahydrotriazine (common name)
